Debug Information

Processing Details

• VTT File: 35e02f52.vtt
• Processing Time: September 11, 2025 at 12:51 PM
• Total Chunks: 1
• Transcript Length: 78,871 characters
• Caption Count: 792 captions

Prompts Used

Prompt 1: Context Setup

You are an expert data extractor tasked with analyzing a podcast transcript. 
I will provide you with part 1 of 1 from a podcast transcript. 
I will then ask you to extract different types of information from this content in subsequent messages. Please confirm you have received and understood the transcript content.

Transcript section:
[00:00:00.240 --> 00:00:03.440] This podcast is hosted by Transistor.fm.
[00:00:18.160 --> 00:00:21.520] Hello and welcome to Build Your SAS.
[00:00:21.520 --> 00:00:25.760] This is the behind-the-scenes story of building web apps in 2022.
[00:00:25.760 --> 00:00:38.400] I'm Justin Jackson from Transistor, and today on the program, I have Dave Zorob, who is the founder, co-founder of Chartable, which was recently acquired by Spotify.
[00:00:38.400 --> 00:00:46.800] Lots of great discussion in here, especially since Dave chose the venture capital route and Transistor chose the bootstrapped route.
[00:00:46.800 --> 00:00:58.880] And it's just interesting to contrast those two and to talk a little bit about, yeah, the Chartable exit, the acquisition with Spotify, and a bunch of other topics.
[00:00:58.880 --> 00:01:00.160] It's a really great episode.
[00:01:00.160 --> 00:01:01.280] I think you'll enjoy it.
[00:01:01.280 --> 00:01:02.880] Let's get into it.
[00:01:03.600 --> 00:01:09.120] Have you started going into the Spotify office or is the megaphone office remote?
[00:01:09.360 --> 00:01:10.640] I go in like once a week.
[00:01:10.640 --> 00:01:12.480] Yeah, so Spotify has worked from anywhere.
[00:01:12.720 --> 00:01:13.120] Okay.
[00:01:13.280 --> 00:01:19.040] So they've like, you know, during the pandemic, totally committed to this remote culture.
[00:01:19.040 --> 00:01:19.760] Got it.
[00:01:19.760 --> 00:01:22.560] My understanding is that it was actually pretty different prior to the pandemic.
[00:01:22.560 --> 00:01:23.920] I mean, I obviously wasn't there.
[00:01:23.920 --> 00:01:28.160] So, but you know, they have this absolutely gorgeous office.
[00:01:28.160 --> 00:01:28.560] I've been there.
[00:01:28.720 --> 00:01:29.600] Downtown Manhattan.
[00:01:29.760 --> 00:01:30.400] It's amazing.
[00:01:30.400 --> 00:01:30.720] Yeah.
[00:01:31.120 --> 00:01:31.600] The view.
[00:01:31.920 --> 00:01:33.040] It's really amazing.
[00:01:33.040 --> 00:01:35.360] Like the view of the water is.
[00:01:35.680 --> 00:01:37.280] I was like, it's crazy.
[00:01:37.280 --> 00:01:42.080] I remember they brought me up to, I mean, I'm a country kid.
[00:01:42.080 --> 00:01:45.520] I grew up in this little farm town in Alberta.
[00:01:45.520 --> 00:01:49.520] And I was meeting a few people there that day.
[00:01:49.520 --> 00:01:52.720] And I've only been, I had only been to New York once before that.
[00:01:52.720 --> 00:01:57.040] So I remember just going into that building and they're like, you're going to have to check in.
[00:01:57.040 --> 00:01:58.400] And so there's like security guards.
[00:01:58.480 --> 00:01:59.760] I had to check in there.
[00:02:00.040 --> 00:02:05.240] And then they bring me up to another place in the elevator.
[00:02:05.240 --> 00:02:08.680] And then it's like this massive waiting room.
[00:02:08.680 --> 00:02:09.880] And then they're like, oh, yeah.
[00:02:09.880 --> 00:02:10.920] And then they check on the computer.
[00:02:11.000 --> 00:02:13.480] They're like, oh, yeah, you're meeting with Bill.
[00:02:13.480 --> 00:02:15.480] And then you're meeting with, okay, yeah, sure.
[00:02:15.480 --> 00:02:17.080] And then they just tell you to wait.
[00:02:17.080 --> 00:02:22.760] And in my mind, I'm thinking, this waiting room is the office.
[00:02:22.760 --> 00:02:26.040] Like, this is it, you know?
[00:02:26.680 --> 00:02:32.920] And like, maybe there's some offices on this floor, like just like around the corner or whatever.
[00:02:32.920 --> 00:02:39.160] And then I think I met with Bill first and he's like, all right, well, let's hop on the elevator.
[00:02:39.160 --> 00:02:41.400] I'm like, wait, there's more floors?
[00:02:41.400 --> 00:02:42.360] There's more.
[00:02:42.680 --> 00:02:43.960] And he's like, oh, yeah.
[00:02:43.960 --> 00:02:46.120] And so we went up and wow.
[00:02:46.600 --> 00:02:49.080] Just, it's just mind-boggling to me.
[00:02:49.080 --> 00:02:54.680] The scale for you, is there a little bit of culture shock?
[00:02:54.680 --> 00:02:56.760] Because how big was Chartable before?
[00:02:57.080 --> 00:02:57.560] For sure.
[00:02:57.560 --> 00:02:58.440] Because Chartable is like a lot of people.
[00:02:58.520 --> 00:02:59.320] I love a few people.
[00:02:59.560 --> 00:02:59.960] Yeah.
[00:03:00.280 --> 00:03:00.920] Yeah.
[00:03:01.160 --> 00:03:13.080] So it's obviously, regardless of like, you know, I think, you know, just to be totally clear, like, part of why we ended up with Spotify is that we really felt like there was like so much alignment, both from a division perspective.
[00:03:13.080 --> 00:03:15.640] I know this sounds cheesy, but it's like actually about people too, right?
[00:03:15.640 --> 00:03:19.240] Like we were like, met a lot of people throughout the lifespan of our company.
[00:03:19.240 --> 00:03:19.560] Yeah.
[00:03:19.560 --> 00:03:24.200] Some of whom were serious about buying our company and some of whom weren't, some of whom were customers, partners, whatever.
[00:03:24.200 --> 00:03:24.520] Yeah.
[00:03:24.520 --> 00:03:26.440] And we're like, these people are great, right?
[00:03:26.440 --> 00:03:30.840] And so, like, you know, the, there's tons of alignment on all this stuff.
[00:03:30.840 --> 00:03:34.360] And it's still, you know, Spotify, I think now is like 8,000 people.
[00:03:34.360 --> 00:03:35.240] Wow.
[00:03:35.240 --> 00:03:39.480] So, you know, there's a little bit of a gap in terms of numbers.
[00:03:39.480 --> 00:03:39.880] Yeah.
[00:03:39.880 --> 00:03:41.240] Just like a little bit.
[00:03:41.400 --> 00:03:43.960] Like, you know, almost three orders of magnitude.
[00:03:43.960 --> 00:03:44.800] So, you know.
[00:03:44.360 --> 00:03:44.960] Yeah.
[00:03:44.680 --> 00:03:45.000] Yeah.
[00:03:46.000 --> 00:03:54.080] That, and not the going from a small team that's kind of focused on one thing.
[00:03:54.080 --> 00:04:03.200] And even like within podcasting, Chartable was focusing on this very narrow piece, right?
[00:04:03.520 --> 00:04:13.200] And now you're in a business that is in music, it's in producing content, it's in ads.
[00:04:13.200 --> 00:04:16.080] It's like that must be so.
[00:04:16.080 --> 00:04:19.600] And even within, because you're in the megaphone division, is that right?
[00:04:19.600 --> 00:04:20.320] Yes.
[00:04:20.320 --> 00:04:20.640] Yeah.
[00:04:20.640 --> 00:04:24.640] So even megaphones business must be quite multifaceted.
[00:04:24.640 --> 00:04:26.400] There's hosting, there's analytics.
[00:04:27.440 --> 00:04:30.080] It's so, it's really complex.
[00:04:30.080 --> 00:04:34.640] Obviously, it's like a huge part of Spotify and a huge part of the podcast industry.
[00:04:34.640 --> 00:04:41.440] So yeah, it's certainly, you know, we've only been there for about three months, a little over three months, and it's absolutely like a huge learning experience.
[00:04:41.440 --> 00:04:47.360] First, like, you know, understanding how stuff works at an organization this large.
[00:04:47.360 --> 00:04:47.680] Yeah.
[00:04:47.680 --> 00:04:48.000] Right.
[00:04:48.560 --> 00:04:52.320] Because the last time I worked at a big company was like 20 years ago, my first job out of college.
[00:04:52.320 --> 00:04:52.560] Right.
[00:04:52.560 --> 00:04:54.960] So like, who are you working for then?
[00:04:55.280 --> 00:04:57.760] I worked at Microsoft right out of school.
[00:04:57.760 --> 00:04:58.480] Wow.
[00:04:58.960 --> 00:04:59.840] In Seattle.
[00:04:59.840 --> 00:05:00.080] Yeah.
[00:05:00.080 --> 00:05:04.240] In Redmond on Office.
[00:05:04.240 --> 00:05:07.200] So that was 2003, right?
[00:05:07.200 --> 00:05:07.680] Yeah.
[00:05:07.840 --> 00:05:09.680] So almost 20 years ago.
[00:05:09.680 --> 00:05:21.120] And, you know, I didn't make it all that long there, although I had, you know, it was certainly an eye-opening experience for like a 21-year-old to like see how software gets made of that skill.
[00:05:21.120 --> 00:05:22.880] But here it's like, it's pretty different, right?
[00:05:22.880 --> 00:05:27.600] Did you work for smaller companies between that?
[00:05:27.600 --> 00:05:29.280] Like before Chartable?
[00:05:29.520 --> 00:05:39.640] I left Microsoft and started a record label in San Francisco with some friends and I was doing some like consulting and then kind of like fell into startups kind of by accident.
[00:05:39.640 --> 00:05:40.760] Like that's what was the recording.
[00:05:40.920 --> 00:05:42.280] What was the record label?
[00:05:42.840 --> 00:05:45.560] I think you told me this, but it was called Tell All Records.
[00:05:45.560 --> 00:05:47.480] Yeah, so it's like a really art music label.
[00:05:47.480 --> 00:05:54.280] We put out like super weird like experimental music, like sound collage, modern composition.
[00:05:54.280 --> 00:05:54.680] Okay.
[00:05:54.680 --> 00:05:55.640] That sort of thing.
[00:05:55.640 --> 00:05:56.440] We did okay.
[00:05:56.440 --> 00:06:01.800] I think our number one record, I mean, CDs we put out back when people bought those.
[00:06:02.280 --> 00:06:02.920] Yeah.
[00:06:02.920 --> 00:06:05.000] Not a bad time to have a record company.
[00:06:05.000 --> 00:06:05.320] Yeah.
[00:06:05.320 --> 00:06:07.720] I mean, we sold 1500 CDs of our top 10.
[00:06:08.120 --> 00:06:08.600] There you go.
[00:06:08.600 --> 00:06:09.400] That was pretty good.
[00:06:09.400 --> 00:06:10.040] Yeah.
[00:06:10.840 --> 00:06:11.400] Yeah.
[00:06:11.640 --> 00:06:12.840] You know, it was a different time.
[00:06:13.000 --> 00:06:15.640] I spent all my savings for Microsoft on this thing.
[00:06:16.120 --> 00:06:18.520] And then, yeah, I kind of stumbled into startups.
[00:06:18.600 --> 00:06:32.600] You know, I moved to San Francisco to be with, hang out with friends and to play music and ended up, you know, start a story in the air, even though it was like 2004 when I moved there and was kind of still like that hangover from dot-com 1.0.
[00:06:32.840 --> 00:06:36.920] And then I kind of like found my peeps, like found, you know, people who are building stuff.
[00:06:36.920 --> 00:06:41.320] And, you know, so I worked for this company called Hot or Knopps, like early dating site.
[00:06:41.320 --> 00:06:41.800] Yeah.
[00:06:42.040 --> 00:06:53.080] I worked for, I started a startup at my first company back in 2007, doing like Facebook apps and then iOS apps, like in the dating, social networking space.
[00:06:53.080 --> 00:06:53.720] Yeah.
[00:06:54.440 --> 00:06:56.120] I worked for AngelList for a long time.
[00:06:56.120 --> 00:07:00.120] So Angelist is like a startup investor network and chatboard.
[00:07:00.280 --> 00:07:02.360] That's how I think I first heard of you.
[00:07:02.360 --> 00:07:02.680] Yeah.
[00:07:02.680 --> 00:07:04.200] It was at AngelList.
[00:07:04.200 --> 00:07:04.520] Yeah.
[00:07:04.520 --> 00:07:09.800] So I've worked at a few different places, but Angelist at the time I joined was, I think, I was the seventh person or something.
[00:07:09.800 --> 00:07:10.120] Right.
[00:07:10.120 --> 00:07:11.000] So wow.
[00:07:11.000 --> 00:07:11.560] Okay.
[00:07:12.040 --> 00:07:15.120] I was also, you know, pretty much all small companies since.
[00:07:14.840 --> 00:07:22.000] And now, you know, we started Chartable back in 2018 after leaving AngelList and trying to figure out what to build.
[00:07:22.320 --> 00:07:25.280] And, you know, we started the podcast ourselves.
[00:07:25.280 --> 00:07:28.880] I think I told this story the last time I was here, but just for those tuning in.
[00:07:28.880 --> 00:07:29.520] Yeah, yeah.
[00:07:29.840 --> 00:07:32.560] You know, my co-vander Harish and I worked together at Angelist.
[00:07:32.640 --> 00:07:36.560] We started this, started together, you know, trying to figure out what to build.
[00:07:36.560 --> 00:07:41.520] We started a podcast summarizing Hacker News, like the Y Combinator newsboard, and it just kind of took off.
[00:07:41.520 --> 00:07:43.040] And we were like, what is this?
[00:07:43.040 --> 00:07:44.560] Like, why is anyone listening to us?
[00:07:44.560 --> 00:07:44.880] Yeah.
[00:07:44.880 --> 00:07:49.360] You know, and that's what led us down the wonderful rabbit hole that is podcasting.
[00:07:49.360 --> 00:07:53.360] So, so you and Harish found Chartable in 2018.
[00:07:53.360 --> 00:07:56.400] Actually, we got to go back a little bit because we're going to fit this in post, right?
[00:07:56.400 --> 00:07:58.720] We're going to make it totally chronological and make it all make sense.
[00:07:58.720 --> 00:08:00.080] No, no, no, no.
[00:08:00.080 --> 00:08:03.520] This will be a meandering conversation.
[00:08:04.240 --> 00:08:10.480] I might give Chris a few notes, but often I just let Chris our editor.
[00:08:10.480 --> 00:08:13.760] He just decides what he thinks is interesting.
[00:08:13.760 --> 00:08:13.920] Yes.
[00:08:14.000 --> 00:08:16.000] I also, hello, Chris.
[00:08:16.160 --> 00:08:20.080] We also hired Chris to edit the Chartable podcast back when we were doing the best.
[00:08:20.560 --> 00:08:21.600] Chris is awesome.
[00:08:21.600 --> 00:08:28.800] Chris always has these one-sided conversations where people are talking to him, but he cannot respond.
[00:08:29.120 --> 00:08:30.000] Yes.
[00:08:30.960 --> 00:08:32.160] He's like, oh, that's nice.
[00:08:32.160 --> 00:08:34.960] You know, he can't say anything.
[00:08:34.960 --> 00:08:39.920] So, were you a computer guy in the beginning, or were you just a computer guy?
[00:08:39.920 --> 00:08:40.720] Still am.
[00:08:40.720 --> 00:08:46.640] So, so, because you were like a creative music kind of, you were into other stuff.
[00:08:46.720 --> 00:08:49.600] Only thing I've ever done for work is programming, right?
[00:08:49.600 --> 00:08:53.120] So, like, when I was, I started doing it when I was like a really little kid.
[00:08:53.120 --> 00:08:58.000] I don't, like, you know, I have, I know the stories that my parents tell more than I remember it myself.
[00:08:58.000 --> 00:09:02.200] I do remember like our first computer's radio shack once I hooked up to the TV.
[00:09:02.200 --> 00:09:03.480] Was it a TRS-80?
[00:09:03.480 --> 00:09:04.200] A TRS.
[00:08:59.280 --> 00:09:04.680] Oh, nice.
[00:08:59.600 --> 00:09:05.400] Yeah.
[00:08:59.680 --> 00:09:15.000] So, well, it ran basic and, you know, we had a cassette deck that would load, like, I almost said apps, programs onto it.
[00:09:15.960 --> 00:09:26.840] The funny thing about those cassettes is I remember we had that on our VIC-20, but you had to type in so much code just to get them.
[00:09:26.840 --> 00:09:38.360] It was, yeah, it was like, and even that, that idea to me, even today, that a cassette could have data on it is just mind-boggling.
[00:09:38.360 --> 00:09:38.840] Yeah.
[00:09:38.840 --> 00:09:41.720] So it goes all the way, I mean, it's literally the only thing I've ever really done.
[00:09:41.720 --> 00:09:42.040] Yeah.
[00:09:42.040 --> 00:09:45.480] You know, I've always been a computer, an indoor kid, as they say.
[00:09:45.480 --> 00:09:45.960] Yeah.
[00:09:45.960 --> 00:09:52.520] And like, you know, I was coding when I was little, you know, went to school, you know, for computer science.
[00:09:52.520 --> 00:09:59.320] Like, I, I did like, when I was in middle school, I was writing like programming tutorials and putting them on the internet with my parents' home address.
[00:10:00.280 --> 00:10:00.840] Yeah.
[00:10:00.840 --> 00:10:20.520] And I think you can still find these with my parents' home address in the text files that were the tutorials, you know, saying like, hey, if you want to like write me a letter or like buy some like, I like published a CDR of all the programs that I like had collected for my website, which was pbasit.com.
[00:10:20.520 --> 00:10:21.320] Wow.
[00:10:21.320 --> 00:10:25.000] And yeah, this is like 1994 or something, you know, so like a while ago.
[00:10:25.000 --> 00:10:29.000] And now all those text files are just like on Usenet forever or something.
[00:10:29.000 --> 00:10:29.400] Yeah.
[00:10:29.400 --> 00:10:31.320] I mean, I think they're still around.
[00:10:32.200 --> 00:10:43.480] My good friend, who was, I guess, my best man when I got married, quoted from some of the tutorials during a speech.
[00:10:43.480 --> 00:10:43.960] That's the thing.
[00:10:44.200 --> 00:10:46.160] Talking about juicy bits of code I was sharing.
[00:10:46.320 --> 00:10:46.640] Wow.
[00:10:44.840 --> 00:10:48.400] But you were, and you were selling these.
[00:10:48.720 --> 00:10:50.320] So, were you, were you at?
[00:10:50.480 --> 00:10:53.040] Yeah, so I like wrote a bunch of tutorials and I would sell.
[00:10:53.360 --> 00:10:59.280] I sold like CDRs of like all the code that, you know, people would submit their programs to be featured on the website.
[00:10:59.280 --> 00:10:59.600] Yeah.
[00:10:59.600 --> 00:11:02.080] We had like a forum with a bunch of stuff that people wrote.
[00:11:02.080 --> 00:11:03.680] And so, yeah, I would sell these CDRs.
[00:11:03.680 --> 00:11:06.240] People would like send cash to my parents' house.
[00:11:06.240 --> 00:11:08.480] That's amazing.
[00:11:08.800 --> 00:11:09.120] Yeah.
[00:11:09.120 --> 00:11:09.760] Wow.
[00:11:10.080 --> 00:11:17.360] And like I was an early Amazon affiliate, you know, back in like 1994, 95.
[00:11:17.360 --> 00:11:24.160] Like you, you know, I think I made it like a, you know, for, I think I was like, you know, in my early teens, maybe preteens.
[00:11:24.160 --> 00:11:24.640] Yeah.
[00:11:24.640 --> 00:11:27.120] It was like decent money, like a few hundred bucks here and there.
[00:11:27.120 --> 00:11:28.400] I was like, this is incredible.
[00:11:28.720 --> 00:11:30.240] You know, that is incredible.
[00:11:30.480 --> 00:11:31.680] Money I've ever seen.
[00:11:31.680 --> 00:11:40.880] I wonder, do you think, like, is that an intuition you just always had that you wanted to make money that way?
[00:11:40.880 --> 00:11:42.080] I don't know about money.
[00:11:42.080 --> 00:11:55.280] You know, I always and still, like, I don't know how much of this is, you know, learned versus just the way my brain is built, but like, I get my, I get my dopamine hits from making stuff.
[00:11:55.280 --> 00:11:55.680] Yeah.
[00:11:55.680 --> 00:12:00.720] The thing I'm pretty good at making, I'm like, much better at making computer stuff than I am at making other stuff.
[00:12:00.720 --> 00:12:01.680] I love playing music.
[00:12:01.680 --> 00:12:02.000] Yes.
[00:12:02.160 --> 00:12:05.040] You know, I'm not the best musician in the world or anything.
[00:12:05.040 --> 00:12:05.360] Yeah.
[00:12:05.360 --> 00:12:09.040] I think I'm a much better programmer than I am a musician, or much rather like product designer.
[00:12:09.360 --> 00:12:11.520] I don't know about designer, but product maker than musician.
[00:12:11.920 --> 00:12:12.560] Yes.
[00:12:12.960 --> 00:12:19.680] So but what, what, where does the attraction towards the commerce side come from?
[00:12:19.680 --> 00:12:23.840] Because there's lots of musicians who are fine, who don't start a record label.
[00:12:23.840 --> 00:14:08.080] A record label is the capitalistic manifestation of music and so i mean it's certainly a money-losing venture so it was in some ways a non-profit not yes simply by choice but like um i don't know there's something about like wanting to put stuff in the world right and and like one you know you need to like you know in music at the time in particular it felt like a retro label was a way you know record labels that i would follow had like very particular brands of the style of music they would release they would support their artists with marketing and stuff and we wanted to do that right so like there were these like small indie labels that i would totally follow and look for every new release that came out and be like hey is this good not every single one would be good but um there was like there was a vibe associated with that and so i wanted to create that sort of vibe and put that stuff in the world are there records that you released that are on spotify um we the artists like own the masters right so i think some of our artists uh like my good friend liam singer who lives in upstate new york he still has music on spotify i think his earliest records that we put out are not on there yeah i don't know that he wants the world to be like hearing them right now you know um we worked with um this guy scott so who's an amazing record uh uh recording engineer and producer he has some ambient music that's still on spotify this woman who goes by noveler now she's like really big in the new york like avant-garde music scene i haven't taught her in like 20 years we put out this record that she made a friend um you know in 2004 or something right but like uh she's has a great music career right uh playing with uh like cool ensembles and stuff it's pretty cool that you you had that experience, and now, in some ways, you're full circle now you are you are uh working for Spotify, which is big in the music game.
[00:14:08.080 --> 00:14:10.240] Yeah, we're kind of yeah back in the game.
[00:14:10.240 --> 00:14:14.400] Yeah, and i did like, you know, I did college radio and was like the music director of my college radio station.
[00:14:14.400 --> 00:14:23.440] So, there is a lot of like kind of like consonants, like echoes here between kind of my past interests and current interests and future interests, right?
[00:14:23.440 --> 00:14:27.120] There's like music and audio and tech, right?
[00:14:27.120 --> 00:14:29.200] Computers, and they're all kind of coming together, man.
[00:14:29.200 --> 00:14:30.080] It's all meant to be.
[00:14:30.160 --> 00:14:31.680] It's all meant to be.
[00:14:32.000 --> 00:14:43.200] Do you think everybody has that intuition though to want to go to the entrepreneurship side of the you do or you don't?
[00:14:43.200 --> 00:14:43.600] I don't.
[00:14:43.600 --> 00:14:44.000] I don't.
[00:14:44.000 --> 00:14:44.480] What do you think?
[00:14:44.480 --> 00:14:50.320] Well, I'm in trouble on Twitter for this at this very moment, so that's why I'm asking you.
[00:14:50.320 --> 00:14:51.840] What's the trouble, man?
[00:14:52.480 --> 00:14:58.000] I mean, I'm just exploring some ideas, and often I explore them in public.
[00:14:58.000 --> 00:15:00.800] And I think I admire you for that.
[00:15:01.120 --> 00:15:15.120] I think one of the things that's interesting, it'd be good to get your take on it, but I, you know, it does seem that entrepreneurship is interesting, even compared to any of those other things you mentioned.
[00:15:15.120 --> 00:15:16.640] Music.
[00:15:17.920 --> 00:15:22.960] Actually, entrepreneurship is very much like those things in some ways.
[00:15:22.960 --> 00:15:25.840] So, anybody can pick up a guitar.
[00:15:25.840 --> 00:15:31.680] Anybody can, in these days, anybody can release music.
[00:15:31.920 --> 00:15:33.280] Anybody can start coding.
[00:15:33.280 --> 00:15:36.320] Anybody can release tutorials on the internet.
[00:15:36.800 --> 00:15:45.840] What's interesting about that compared to other things where there's a lot of gatekeepers is not gatekeepers.
[00:15:45.840 --> 00:16:02.520] It's what's interesting about entrepreneurship compared to other competitive pursuits like the UFC or the NBA is that I can't just wake up one day and say, I want to step into the ring with Conor McGregor, right?
[00:16:02.520 --> 00:16:03.480] I can't just do that.
[00:16:03.880 --> 00:16:07.960] I can't just one day just run on the I don't know who that is, but I assume that's a UFC person.
[00:16:07.960 --> 00:16:15.880] Yeah, the problem is I use this UFC metaphor, the example, and now everyone thinks I'm like into violent sports.
[00:16:15.880 --> 00:16:16.600] Are you a UFC?
[00:16:16.680 --> 00:16:17.240] Which I'm not.
[00:16:17.880 --> 00:16:18.920] I'm not at all.
[00:16:19.160 --> 00:16:21.640] But he's a famous person who's a big fighter.
[00:16:21.640 --> 00:16:22.280] He's a big fighter.
[00:16:22.280 --> 00:16:23.480] And you can't just go fight him.
[00:16:23.480 --> 00:16:23.800] That's right.
[00:16:23.800 --> 00:16:25.960] And, or you could, maybe.
[00:16:26.440 --> 00:16:29.080] Well, you could, but they wouldn't let you.
[00:16:29.080 --> 00:16:29.960] You know what I mean?
[00:16:29.960 --> 00:16:36.040] Like, I can't just run onto the court during an NBA game and say, okay, I'm a basketball player now.
[00:16:36.040 --> 00:16:50.520] And, you know, and but entrepreneurship and music and anybody who wants to be a public programmer person, anybody can put out their shingle and say, all right, I'm an entrepreneur.
[00:16:50.520 --> 00:16:51.800] All right, I'm a musician.
[00:16:52.040 --> 00:16:56.200] All right, I'm a programmer who shares stuff on the internet.
[00:16:56.200 --> 00:17:03.720] And what's interesting about that is we are still competing with people at the highest caliber.
[00:17:03.720 --> 00:17:12.520] So you're still competing with LeBron James, but you are just some person off the street.
[00:17:12.920 --> 00:17:14.200] Yeah, you're just a guy.
[00:17:14.200 --> 00:17:15.160] I'm in my garage.
[00:17:15.160 --> 00:17:15.320] Yeah.
[00:17:15.560 --> 00:17:16.600] Making websites, man.
[00:17:16.600 --> 00:17:17.240] Yeah.
[00:17:18.200 --> 00:17:45.920] And I find that fascinating, partly because one of the things when I talk about business, one of the things I kind of explore is I say, I think actually in business, you want to look at the survivors, the survivors, the people, like survivorship bias.
[00:17:45.920 --> 00:17:56.960] We actually want that in business because statistically, the pool of people who can just put out a shingle is infinite.
[00:17:56.960 --> 00:18:03.840] Anybody on their tax return can say, well, I'm a sole proprietor and I lost $20 this year.
[00:18:03.840 --> 00:18:22.000] And so if that's true, then we, whenever we're thinking about business and we're thinking about how to do business well, we almost have to exclude that group automatically and say, well, we can't really be thinking too.
[00:18:22.000 --> 00:18:23.360] So often, you know, I'll say.
[00:18:23.680 --> 00:18:30.320] Is this the controversial part where you're like trying to like kind of separate a certain kind of business from another kind of business or a certain kind of entrepreneur from others?
[00:18:30.320 --> 00:18:34.240] I think that's the part that people got sensitive about.
[00:18:34.240 --> 00:18:42.480] I can see how people might be sensitive, but I think it's true, if only because like, you know, people's motivations and like the desired outcomes are different.
[00:18:42.480 --> 00:18:44.400] It's like, are you even playing the same game?
[00:18:44.400 --> 00:18:44.880] Yeah.
[00:18:45.120 --> 00:18:49.360] So like, to go with the sport metaphor, it's like, are we playing the same sport?
[00:18:49.360 --> 00:19:00.560] Like, if, like, if you're playing like entrepreneurship volleyball and I'm playing entrepreneurship water polo, am I, you know, are we, should we really be judged by the same rules?
[00:19:00.560 --> 00:19:00.880] Yes.
[00:19:00.880 --> 00:19:01.360] Right.
[00:19:01.360 --> 00:19:15.280] And I think that that could apply to like somebody's side project that they're doing out of total passion, zero commercial desire versus, you know, bootstrap business whose goal is to be profitable or massively profitable.
[00:19:15.280 --> 00:19:15.600] Yeah.
[00:19:15.600 --> 00:19:19.920] Versus like a venture-batched startup whose like plan is to like lose tons of money for a while.
[00:19:19.920 --> 00:19:20.320] Yes.
[00:19:20.320 --> 00:19:20.720] Right.
[00:19:21.040 --> 00:19:21.360] Yeah.
[00:19:21.360 --> 00:19:22.040] Let's, okay.
[00:19:22.040 --> 00:19:22.240] Let's.
[00:19:22.400 --> 00:19:23.840] These are like very different games.
[00:19:23.840 --> 00:19:24.080] Yeah.
[00:19:24.080 --> 00:19:24.960] Let's let's talk.
[00:19:24.960 --> 00:19:26.800] Let's dig into this a little bit.
[00:19:26.800 --> 00:19:38.520] So for you, when you were starting Chartable, outside of your business objective or your even your philosophical objective, what was your personal objective?
[00:19:38.520 --> 00:19:40.520] Like why were you starting it?
[00:19:40.520 --> 00:19:45.880] Why were you making this bet and risking your time and your energy, et cetera?
[00:19:45.880 --> 00:19:48.280] What were you hoping to get out of it personally?
[00:19:48.600 --> 00:19:55.480] I think that if I'm really honest with myself, there's a lot of ego involved.
[00:19:55.480 --> 00:20:05.400] I have been trying to build startups for a long time and had never really gotten anywhere that I could point to and say, I'm super duper proud of that.
[00:20:05.400 --> 00:20:06.680] I did that myself.
[00:20:06.680 --> 00:20:10.760] You know, that said, like, that's certainly part of it and probably more than I want to admit.
[00:20:10.760 --> 00:20:17.080] Another part of it is that, like, I'm wired to get kicks from putting stuff on the internet, right?
[00:20:17.080 --> 00:20:19.160] And making stuff that people use.
[00:20:19.880 --> 00:20:36.760] When we've stumbled upon podcasting as like a potential industry to explore, I was just totally shocked that the kind of tools available to creators were, you know, I hate to say this word, but I'll use it, like, primitive compared to what's available for other media.
[00:20:36.760 --> 00:20:43.000] Like, you know, I mentioned earlier, I do, you know, I made mobile apps in the early days of the App Store.
[00:20:43.000 --> 00:20:55.160] And really quickly, these very sophisticated tools developed for creators to, you know, I don't know if we would have taught them creators at the time, but developers to make apps and to like, you know, figure out what's working and to grow them and all that stuff.
[00:20:55.160 --> 00:20:56.040] We were just kind of shocked.
[00:20:56.280 --> 00:20:58.200] Tools like App Annie.
[00:20:58.200 --> 00:21:04.840] Yeah, App Annie, Flurry, even the early monetization networks like Admob and stuff all had a big analytics component.
[00:21:04.840 --> 00:21:05.240] Yeah.
[00:21:05.240 --> 00:21:12.040] You know, because like you put this app out there and you had no idea what was happening other than like you would get download numbers from Apple once a day.
[00:21:12.040 --> 00:21:12.440] Yeah.
[00:21:12.440 --> 00:21:12.920] Right.
[00:21:12.920 --> 00:21:13.480] Yes.
[00:21:13.480 --> 00:21:17.040] So even worse than what podcasting was when we started.
[00:21:17.440 --> 00:21:17.840] Yes.
[00:21:17.840 --> 00:21:18.240] Yeah.
[00:21:18.560 --> 00:21:19.600] Exactly.
[00:21:14.920 --> 00:21:21.680] But you know, quickly it got super sophisticated.
[00:21:21.760 --> 00:21:26.800] And I think that that helped enable what is an absolutely massive app economy.
[00:21:26.800 --> 00:21:29.680] And we were hoping to do the same for audio, for podcasting.
[00:21:29.840 --> 00:21:30.400] Podcasting.
[00:21:30.400 --> 00:21:30.640] Right.
[00:21:30.640 --> 00:21:32.640] So I got, I like making stuff, right?
[00:21:32.640 --> 00:21:34.240] That's like, that's ultimately what it comes down to.
[00:21:34.320 --> 00:21:35.920] And I want to get more into that too.
[00:21:35.920 --> 00:21:47.040] But there's still, I gotta, I just want to sit here for a second because there's a I understand the draw to want to make stuff.
[00:21:47.040 --> 00:21:49.120] I understand that completely.
[00:21:49.120 --> 00:21:54.400] I also understand the attraction to what seems like an opportunity.
[00:21:54.400 --> 00:22:05.040] Hey, there's a wave out there that seems to be growing and I want to take my surfboard and I want to paddle out and I want to try to catch that wave because it looks like a good wave.
[00:22:05.680 --> 00:22:07.680] I can understand all of that.
[00:22:08.560 --> 00:22:21.120] But, you know, for me, I still had to discuss with my spouse, you know, hey, I'm about to embark on this journey and even pre-transistor.
[00:22:21.120 --> 00:22:22.400] Like, why are you doing this?
[00:22:22.400 --> 00:22:28.400] Why don't you just try to get another job at Microsoft and climb the ladder?
[00:22:28.400 --> 00:22:31.120] And that might be better.
[00:22:31.120 --> 00:22:33.680] So what was driving you personally?
[00:22:33.680 --> 00:22:35.760] Why even play this game?
[00:22:35.760 --> 00:22:38.640] Why make these bets in the first place?
[00:22:38.640 --> 00:22:40.800] I mean, I think ego is actually a pretty good answer.
[00:22:40.800 --> 00:22:41.680] That's part of it.
[00:22:41.680 --> 00:22:50.480] Yeah, I mean, ego is probably a big chunk of it, but also like, and this is, they're probably related, but like literally, what, what makes me happy, right?
[00:22:50.480 --> 00:23:00.600] What makes me happy is, and this has always been the case since I was putting like programming tutorials on the internet like, like you know, 30 years ago, right?
[00:22:59.440 --> 00:23:03.800] Making stuff that people use makes me happy, period.
[00:22:59.760 --> 00:23:08.120] Yeah, and you get to make a lot more stuff when you start a company.
[00:23:08.120 --> 00:23:21.720] You have a much tighter loop between, hey, I have this idea that might be good, and let's find out if it's good, versus like the kind of, you know, just by its nature, any larger company has more risk.
[00:23:21.720 --> 00:23:27.160] You know, like it's risky for them to do something new, and so it has to run through all the different departments and all that stuff.
[00:23:27.160 --> 00:23:27.800] Yeah.
[00:23:27.800 --> 00:23:41.160] I remember when I joined Microsoft, I was supposed to try to fix a bug with the spell checker that's like a shared component between like Outlook and Word and all the Office stuff.
[00:23:41.480 --> 00:23:50.680] And they were like, you have to go talk to so-and-so over in Word because he owns the dialogue box that contains the spell checker settings.
[00:23:50.920 --> 00:23:53.560] It's like this guy's like life's work, basically.
[00:23:53.560 --> 00:23:53.880] Right.
[00:23:53.880 --> 00:23:54.280] Yeah.
[00:23:54.280 --> 00:23:56.600] And I'm like, I don't know that I want to be that guy.
[00:23:56.600 --> 00:24:02.680] Like, I think that's a good thing to own that to make sure that that dialogue box, that settings panel is really good.
[00:24:02.680 --> 00:24:05.640] And I'm glad that somebody really wants to do that.
[00:24:05.640 --> 00:24:06.440] Right.
[00:24:06.920 --> 00:24:13.800] But for me, I wouldn't get enough kicks out of it to like refine the dialogue box for 20 years.
[00:24:13.800 --> 00:24:14.120] Yes.
[00:24:14.120 --> 00:24:14.520] Right.
[00:24:14.840 --> 00:24:23.080] But and then there's this other iteration on top of that, which is you start this record label, which is fun.
[00:24:23.080 --> 00:24:24.360] You control things.
[00:24:24.360 --> 00:24:25.800] You get to find the artist.
[00:24:25.800 --> 00:24:27.560] You get to do the marketing.
[00:24:27.560 --> 00:24:32.920] But there was part of that that was not satisfying because you say it didn't make very much money.
[00:24:32.920 --> 00:24:33.240] Yeah.
[00:24:33.240 --> 00:24:39.560] I mean, I spent all the saving money I saved up, uh, and um, we weren't able to do it anymore because we ran out of money.
[00:24:39.560 --> 00:24:40.120] Right.
[00:24:40.120 --> 00:24:42.760] You know, going back to the idea of the different paths, right?
[00:24:42.760 --> 00:24:51.200] Side project versus bootstrap versus like a venture, and these are not the only options, but there are a few of the many available options for making something on the internet.
[00:24:51.520 --> 00:24:55.600] It was not sustainable for something to just keep eating money, yeah.
[00:24:55.600 --> 00:24:58.400] And there's no way anyone was going to invest in our art label.
[00:24:58.400 --> 00:24:59.440] I didn't even think about it.
[00:24:59.440 --> 00:25:01.280] Yeah, yeah, yeah, yeah.
[00:25:01.280 --> 00:25:02.640] Uh, so like, what's the goal?
[00:25:02.640 --> 00:25:06.080] What's, you know, what you know, I was too young to have like really thought it through.
[00:25:06.080 --> 00:25:08.640] We just thought it would be something cool to do and something fun to work on with friends.
[00:25:08.640 --> 00:25:09.120] Yeah, right.
[00:25:09.120 --> 00:25:11.360] Well, I mean, I, and I've been, I've been there.
[00:25:11.680 --> 00:25:13.360] I know that feeling.
[00:25:13.360 --> 00:25:21.440] I think one thing I'm just, and I think this will, as we get into this kind of funded versus bootstrap conversation, it'll be interesting.
[00:25:21.440 --> 00:25:33.680] But the, again, the thing about business, if anybody can put out a shingle and then try it, which is great, I think what you quickly learn is that you're doing this for reasons.
[00:25:33.680 --> 00:25:34.960] I want to be creative.
[00:25:34.960 --> 00:25:36.640] I want to have freedom.
[00:25:36.640 --> 00:25:39.920] I want to have people use the things I make.
[00:25:39.920 --> 00:25:42.080] I want to, you know, all those things.
[00:25:42.400 --> 00:26:02.160] And it's very likely if I was independently wealthy, like if I was just a trust fund kid or something, maybe I wouldn't start businesses because maybe if I could just create things, I would be okay with it.
[00:26:02.160 --> 00:26:02.800] What do you think?
[00:26:02.800 --> 00:26:12.720] Do you think for you, if the economic incentive wasn't there, you would have been okay to just keep creating things if you knew you just had enough money?
[00:26:12.720 --> 00:26:13.600] It's hard to say, right?
[00:26:13.600 --> 00:26:15.600] Because I'm not a trust fund kid, you know?
[00:26:15.760 --> 00:26:19.600] And so, like, obviously, like, wanting to make money is part of it.
[00:26:19.560 --> 00:26:23.120] But, but like, money is definitely not my primary motivator.
[00:26:23.120 --> 00:26:23.840] It just isn't.
[00:26:23.840 --> 00:26:29.120] I could have, I would have made many different decisions all throughout my career, if you even want to call it that.
[00:26:29.160 --> 00:26:41.320] That uh, if money were my primary motivator, I've left great jobs a bunch of times because, like, uh, it wasn't, you know, I felt like I had something else to a different itch to scratch.
[00:26:41.320 --> 00:26:43.160] Yes, I guess we'll see.
[00:26:43.160 --> 00:26:46.760] I, I, you know, life is long, right?
[00:26:46.760 --> 00:26:51.960] Um, you know, this was an amazing outcome for me and for my team, but I'm not done yet, right?
[00:26:51.960 --> 00:26:53.720] And so, the motivations are different.
[00:26:53.720 --> 00:26:58.520] It's not the same as like literally thinking that this is like life or death.
[00:26:58.520 --> 00:27:03.000] Obviously, it wasn't life or death, it's just making a website on the internet and trying to sell it.
[00:27:03.000 --> 00:27:18.120] It felt so intense, especially the kind of the last year, year and a half of Chartable's independent existence, um, really trying to fulfill what I saw as its potential.
[00:27:18.120 --> 00:27:24.280] Yeah, uh, it felt like this like imperative, and a lot of that, you know, it's economic, right?
[00:27:24.600 --> 00:27:37.400] Um, but also just like deeply personal, you know, deeply, it's about my own baggage as a maker of things and as a person existing in the world that I felt like I really had to do this, yes, right?
[00:27:37.400 --> 00:27:39.960] Yeah, and do I feel like I still have to do it?
[00:27:39.960 --> 00:27:40.840] Yeah, I do.
[00:27:40.840 --> 00:27:43.160] Like, I'm broken in that way, right?
[00:27:43.160 --> 00:27:50.760] Like, that, uh, you know, if I were to be done, you know, I'm we have a long, a lot of work to do at Spotify.
[00:27:50.760 --> 00:27:59.720] Yeah, whenever that work is done, you know, I don't think I'm just gonna like go chill on a beach for five years, like I'm just gonna go do something else, go make something else, right?
[00:27:59.720 --> 00:28:20.000] I don't know that I could help that, yeah, you know, even if I like thought that it was like irrational, which I think it is irrational to do, um, I'm still going to probably do it because that's just that's how at this point, that feedback loop of wanting to make something and seeing it made and seeing people use it and trying to make it better and trying to sell it and trying to learn.
[00:28:21.040 --> 00:28:23.520] That's that's that's my that's my loop.
[00:28:23.520 --> 00:28:24.800] I'm addicted to it, right?
[00:28:24.800 --> 00:28:25.680] That's what I want to do.
[00:28:25.680 --> 00:28:44.080] And your comment about the timeline is so interesting because one of the things that was interesting when you and I met was we were on this path where our timelines were adjacent, and but we had we got to see the flux of that, right?
[00:28:44.080 --> 00:28:47.280] And of course, life is still playing out.
[00:28:47.280 --> 00:28:53.680] Uh, so I got to watch you make bets, and you got to watch John and I make bets.
[00:28:53.680 --> 00:29:02.720] And at different times, it felt like you know, like at the beginning, you had raised money, and so you and you and I talked about this.
[00:29:02.720 --> 00:29:09.200] It's very, it's kind of like at that point when you raise, I think you raised 1.3 initially, is that right?
[00:29:09.200 --> 00:29:12.240] Yeah, it's like uh, yeah, almost one and a half, not quite one and a half.
[00:29:12.240 --> 00:29:24.560] So you raised one and a half, and it was like you had chosen a path because at that point, you know, getting to 20k MRR wasn't like that wouldn't be good enough.
[00:29:24.560 --> 00:29:28.480] Like you had to keep, you had, you had a different path, correct?
[00:29:28.480 --> 00:29:39.840] Yeah, it was, there was a point, you know, we had thought that we were gonna like try to bootstrap it, bootstrap it, meaning like we didn't even know what we were building, bootstrap our company, right, when we quit our jobs at Angelist.
[00:29:39.840 --> 00:29:45.760] But when we fell down the podcast rabbit hole, we just thought, like, man, this opportunity is just so dang big.
[00:29:45.760 --> 00:29:50.480] And it would be foolish not to be more aggressive.
[00:29:50.800 --> 00:29:52.640] That was our thought at the time.
[00:29:52.640 --> 00:29:55.600] Now, I will say that's not the only path.
[00:29:55.600 --> 00:29:56.960] That's the path that we chose.
[00:29:57.040 --> 00:30:01.160] I'm incredibly impressed by what you and John have built.
[00:29:59.760 --> 00:30:12.200] And there's a lot of other folks building and podcasting that have been building their own way, whether that's a venture way or angel way or a self-funded way, whatever way it is, or as a side project, right?
[00:30:12.200 --> 00:30:12.760] Yeah.
[00:30:12.760 --> 00:30:15.000] You know, these are all totally valid paths.
[00:30:15.320 --> 00:30:16.840] We chose a particular path.
[00:30:16.840 --> 00:30:19.640] And once we chose, we had to commit, right?
[00:30:19.640 --> 00:30:21.400] There's no going back, right?
[00:30:22.120 --> 00:30:27.400] So that certainly changed what our company's journey looks like.
[00:30:27.400 --> 00:30:31.480] And in the end, we have an outcome that I think we can all be very happy with.
[00:30:31.480 --> 00:30:38.840] Was it the absolute world-changing $10 bazillion dollar outcome?
[00:30:38.840 --> 00:30:39.080] No.
[00:30:39.080 --> 00:30:45.640] But was it like a really important change for us and a great positive outcome for our team and our investors?
[00:30:45.640 --> 00:30:45.880] Yeah.
[00:30:45.880 --> 00:30:47.560] And that's great, you know?
[00:30:47.880 --> 00:30:48.840] And I'm really proud of that.
[00:30:48.840 --> 00:30:50.040] Yeah, well, and you should be.
[00:30:50.040 --> 00:31:00.840] I think that that's what I liked about talking to you is because it was like I could see, I mean, and there were times where I could see Dave's approaches is probably better.
[00:31:00.840 --> 00:31:11.400] Like at the beginning, when John and I were suffering and, you know, John's still working a full-time job, I had my own stuff going on, but I'm really putting all my time and energy into a transistor.
[00:31:11.400 --> 00:31:15.240] And so I had money stress and John had time stress.
[00:31:15.240 --> 00:31:20.840] Because now it's easy to like gloss over that in the past, but it's very likely the initial pain.
[00:31:20.840 --> 00:31:25.320] Well, the initial pain, it's very likely we might not have made it through that.
[00:31:25.640 --> 00:31:36.040] And I think when I've talked to other folks who have raised money, Adie Pinar is another one who he's saying he bootstrapped initially WooCommerce.
[00:31:36.040 --> 00:31:42.600] And then everything he's done since, he said, I'm never bootstrapping again because it's not fair to my family.
[00:31:43.560 --> 00:31:57.520] The idea that I would be running this thing on fumes and hoping to make it through this ring of fire unscathed is just, it's too much to ask.
[00:31:57.520 --> 00:32:02.640] There was a huge cost, you know, for me personally, for my, you know, my wife and my kids and stuff.
[00:32:02.640 --> 00:32:07.440] Like it was like, you know, to deny that I think would be, you know, dishonest, right?
[00:32:07.440 --> 00:32:08.480] It was absolutely a huge cost.
[00:32:08.480 --> 00:32:13.840] My wife, you know, you had mentioned talking to your response about before starting transistor that it's like a big change.
[00:32:13.840 --> 00:32:16.720] And we talked it through and we had some timelines.
[00:32:16.720 --> 00:32:19.600] And like, you know, given that we had a good outcome, it all makes sense.
[00:32:19.600 --> 00:32:22.320] In the retrospect, it was also a great idea, great way to go.
[00:32:22.320 --> 00:32:24.960] It absolutely could have gone a different way, right?
[00:32:24.960 --> 00:32:27.040] And it would have been, it would have felt very different.
[00:32:27.360 --> 00:32:36.560] And even, you know, especially at the end, like going through an MA process, it was very stressful.
[00:32:36.880 --> 00:32:39.200] And my kids noticed, right?
[00:32:39.200 --> 00:32:41.280] I have two, like a six-year-old and a three-year-old.
[00:32:41.360 --> 00:32:42.320] They absolutely noticed, right?
[00:32:42.320 --> 00:32:44.640] So I'm not, wasn't around very much, right?
[00:32:44.640 --> 00:32:46.320] I was here in the garage, right?
[00:32:46.720 --> 00:32:47.600] All the time.
[00:32:47.600 --> 00:32:56.640] You know, I'd wake up at like five, do some work, go in at 6:30 and get my older daughter ready for school, walk her to school, come back.
[00:32:56.640 --> 00:33:02.720] You know, it's just like, it was like, there's some weeks and months of like total grind, right?
[00:33:02.720 --> 00:33:04.080] But in retrospect, totally worth it.
[00:33:04.320 --> 00:33:13.840] Do you think raising money made the personal side, family side, less stressful because you were able to pay yourself a salary from the beginning?
[00:33:13.840 --> 00:33:15.600] Yeah, it definitely did.
[00:33:15.600 --> 00:33:20.800] I mean, we had a kind of built-in checkpoint.
[00:33:20.800 --> 00:33:24.640] I personally had one because we knew that we wanted to have a second child.
[00:33:24.640 --> 00:33:33.880] And either I would have to have something that was like, I would be okay with committing to bootstrapping and saying, okay, we're going to bootstrap this, and this is the plan.
[00:33:33.960 --> 00:33:40.440] And then I'll be making excess dollars a month within, you know, 18 months or whatever it is, or raise money or go get a job.
[00:33:40.440 --> 00:33:40.840] Yeah.
[00:33:40.840 --> 00:33:41.720] Those are my options.
[00:33:41.720 --> 00:33:42.120] Yeah.
[00:33:42.120 --> 00:33:42.440] Right.
[00:33:43.320 --> 00:33:46.760] And so that's probably influenced our decision making a little bit.
[00:33:47.320 --> 00:33:54.520] But once we were able to raise, like, yeah, like having health insurance, which, you know, you guys don't have to worry about in Canada.
[00:33:54.840 --> 00:33:56.520] Well, we have to worry about it for John.
[00:33:56.920 --> 00:33:57.720] And Jason.
[00:33:57.720 --> 00:33:59.720] We have John and Jason now.
[00:33:59.720 --> 00:34:03.640] And so Helen and I, Helen's in the UK, I'm in Canada.
[00:34:03.640 --> 00:34:05.560] And it's a lot easier.
[00:34:05.560 --> 00:34:06.120] You guys have it covered.
[00:34:06.280 --> 00:34:07.080] A lot easier.
[00:34:07.720 --> 00:34:11.720] Like all we have to worry about for Helen and I is dental and vision.
[00:34:11.720 --> 00:34:18.840] I was paying for Cobra out of pocket for my family, you know, from the time I left Angelus till we raised money.
[00:34:19.160 --> 00:34:22.360] And that was absolutely brutal, right?
[00:34:22.360 --> 00:34:24.280] It's like just totally insane.
[00:34:24.920 --> 00:34:33.720] And I imagine, you know, I imagine it has some impact on entrepreneurship in the US because like it's like thousands of dollars a month, you know, crazy.
[00:34:33.720 --> 00:34:37.000] Joe Biden, if you're listening to this, I mean, I'm sure he'd agree.
[00:34:37.000 --> 00:34:37.480] Yes.
[00:34:37.480 --> 00:34:39.080] But actually, actually, I'm sure he'd agree.
[00:34:39.080 --> 00:34:39.400] Yeah.
[00:34:39.400 --> 00:34:40.040] Is it doable?
[00:34:40.040 --> 00:34:40.600] But yeah.
[00:34:41.720 --> 00:35:01.240] To those on the other side of the house, if you're listening to this, I think that the greatest gift you could give entrepreneurship, free market economy like the United States, is health insurance because you want to give people some sort of safety net.
[00:35:01.240 --> 00:35:10.520] And I absolutely, even starting a business was definitely a massive risk, especially since I've had businesses fail.
[00:35:11.160 --> 00:35:23.920] But if I knew that, if I didn't know that I, if one of my kids got sick, I'd be able to go to the hospital and it wouldn't cost me $30,000 or $100,000 or whatever.
[00:35:23.920 --> 00:35:27.360] I don't think I would have started a business because it's too big of a risk.
[00:35:27.360 --> 00:35:30.400] Yeah, super, it is like a huge impediment.
[00:35:30.400 --> 00:35:37.760] And like for us, I basically was paying for like Cobra, which is a continuation of like your previous employer's health insurance.
[00:35:37.760 --> 00:35:39.280] And it was just crazy expensive.
[00:35:39.280 --> 00:35:41.360] And it was the only way I could make it work, right?
[00:35:41.360 --> 00:35:43.360] It's like there's really no other option.
[00:35:43.360 --> 00:35:54.080] And absolutely factored into, you know, my like very scary spreadsheet of impending doom of like whether I would have to like get a job or like give up, you know?
[00:35:54.880 --> 00:35:56.720] And it won't be the same next time, right?
[00:35:56.720 --> 00:36:10.960] Like, you know, we were fortunate enough to have a good enough outcome that if I were to do the irrational thing and to try down at some point in the very distant, hopefully very distant future, ask my wife, she hopes it's also very distant, you know, that it wouldn't be as much of a burden, right?
[00:36:11.520 --> 00:36:29.840] But it'd still be hard to, you know, it's still just like a massive cost and a scary thing, you know, with a family to think that like, well, just because like dad has a really weird brain and he really likes making things on the internet in this very particular way.
[00:36:29.840 --> 00:36:32.880] And so he's going to do this crazy thing and it's going to impact you.
[00:36:32.880 --> 00:36:34.320] Like, I don't know, that's pretty weird, man.
[00:36:34.320 --> 00:36:38.880] I don't even know that I'm, when I frame it that way, I'm like, wow, like, does that really the right thing to do?
[00:36:38.880 --> 00:36:39.360] I don't know.
[00:36:39.360 --> 00:36:39.840] Yeah.
[00:36:40.800 --> 00:37:09.080] I mean, it's so interesting to think about the in terms of a bat because one thing I was just thinking about while you were speaking is in some ways, you pre-acquisition and me right now, I think we do have a similar anxiety, which is most of my potential net worth is still locked up in this company.
[00:37:09.400 --> 00:37:22.600] And I think the benefit that profitable bootstrapped companies have is that if they are doing well, founders can take more money off the table each year just through distributions.
[00:37:22.920 --> 00:37:33.160] But like the way I describe it now is, especially since this, you know, whatever transistor is, it's, it's a, it's a, I think it's a success for a bootstrap company.
[00:37:33.160 --> 00:37:35.960] But it came to me in my 40s.
[00:37:35.960 --> 00:37:43.480] And so I say, I'm, I am poor in terms of net worth, but, but wealthy in terms of income, right?
[00:37:43.480 --> 00:38:00.680] So it's nice having a high income, but there's still this feeling of like, if this goes away, I still have that same anxiety of like I haven't taken enough off the table for this to be fine.
[00:38:00.680 --> 00:38:06.360] Now, every year that we keep going, that becomes less and less of a concern.
[00:38:06.360 --> 00:38:19.000] But the selling your company, you're basically pulling forward all you're pulling forward years and years of revenue in the future, and you're getting it now and you're able to put it away, right?
[00:38:19.000 --> 00:38:19.480] Yep.
[00:38:19.480 --> 00:38:19.960] Yep.
[00:38:19.960 --> 00:38:21.240] And it's trade-off, right?
[00:38:21.240 --> 00:38:25.560] I mean, you know, for us, it was absolutely the right thing to do.
[00:38:25.560 --> 00:38:42.040] And like, we really couldn't be happier about where we ended up and our timing, and feeling like we have the ability to like kind of go even kind of bigger with our vision for publisher tools, right?
[00:38:43.480 --> 00:38:45.440] As part of Spotify.
[00:38:44.600 --> 00:38:49.200] But yeah, you know, you want to talk to anxiety, man.
[00:38:49.360 --> 00:38:51.760] I mean, I was a mess, you know?
[00:38:52.400 --> 00:38:58.320] And that kind of existential dread is not there in the same way.
[00:38:58.320 --> 00:39:06.480] But now it's like, well, we did this thing, like we have to kind of make good on all of our promises to customers and all the things that we talked about.
[00:39:06.480 --> 00:39:08.240] Like we, we've, we have all these ideas.
[00:39:08.240 --> 00:39:11.040] We've been doing this for four plus years now.
[00:39:11.040 --> 00:39:14.800] I think our, I guess our four-year anniversary of Charlotte will be like next week or something.
[00:39:14.800 --> 00:39:15.440] Oh, nice.
[00:39:15.920 --> 00:39:17.840] And we have a lot of work to do.
[00:39:17.840 --> 00:39:22.160] And it's just, it's very different to get that work done in the larger environment.
[00:39:22.160 --> 00:39:25.040] There's like kind of, it's almost like there's more at stake.
[00:39:25.040 --> 00:39:26.800] It's not like there's more at stake for me.
[00:39:26.960 --> 00:39:33.440] Like personally, like if I screw up, then like my entire income is going to be destroyed and my family will be ruined.
[00:39:34.240 --> 00:39:40.640] But, you know, Spotify has really big ambitions for its podcast business.
[00:39:41.120 --> 00:39:44.080] And we're hoping to play a very large part of that.
[00:39:44.080 --> 00:39:45.760] And so we have to do that, right?
[00:39:45.760 --> 00:39:46.640] It's work.
[00:39:46.640 --> 00:39:47.760] It's work to be done.
[00:39:48.000 --> 00:39:51.440] And so I've kind of traded one kind of anxiety for another.
[00:39:51.440 --> 00:39:52.880] I'll absolutely take that trade.
[00:39:53.920 --> 00:39:59.280] And now my anxiety is, can we like make good on our promises, make good on the vision?
[00:39:59.280 --> 00:39:59.680] Yeah.
[00:39:59.680 --> 00:40:01.200] And, you know, so far so good.
[00:40:01.200 --> 00:40:03.040] It's still early days, right?
[00:40:03.760 --> 00:40:06.160] But it's definitely just trading.
[00:40:06.160 --> 00:40:09.600] And this is probably just another way that I'm wired is to worry about something.
[00:40:09.600 --> 00:40:09.840] Yeah.
[00:40:09.840 --> 00:40:12.320] Not worried about, okay, can we actually follow through?
[00:40:12.320 --> 00:40:12.560] Yeah.
[00:40:12.560 --> 00:40:13.040] Right.
[00:40:13.040 --> 00:40:13.600] Yeah.
[00:40:13.920 --> 00:40:16.560] Can you tell me a bit about that transition?
[00:40:16.560 --> 00:40:28.720] When I talked to John about an acquisition, his feeling is like, ah, neither of us has worked for a big company, but we've both worked for companies of 100, 200 people.
[00:40:28.720 --> 00:40:32.280] And we, we like this way more.
[00:40:29.600 --> 00:40:39.800] But every once in a while, I have a thought of like, maybe we could.
[00:40:40.120 --> 00:40:55.400] See, this is the fantasy, but I think maybe this is delusional, but maybe we could, John, maybe we could go to somewhere like Amazon or Spotify or Apple and really kick ass at that level.
[00:40:55.400 --> 00:40:57.960] That would be sort of interesting.
[00:40:59.480 --> 00:41:13.400] How was the transition for you and your team of being like you're this little unit that can execute at a certain level and you're scrappy and you're, you know, you're doing all the things?
[00:41:13.400 --> 00:41:18.200] Is that transition difficult going from small company to big company?
[00:41:18.200 --> 00:41:19.320] Do you feel more empowered?
[00:41:19.320 --> 00:41:25.720] Like, do you just feel like you've just got a bunch more gas in your tank and now, or they've given you like rocket boosters?
[00:41:25.720 --> 00:41:29.480] Like, what's the feeling inside of a bigger company?
[00:41:29.480 --> 00:41:30.920] Yeah, it's definitely a different feeling.
[00:41:30.920 --> 00:41:32.520] For me, I think there's trade-offs, right?
[00:41:32.520 --> 00:41:37.080] Like the total impacts we can have if we're able to execute.
[00:41:37.080 --> 00:41:39.960] I mean, we are able to execute because we're very capable.
[00:41:41.240 --> 00:41:49.080] But, you know, the impact we can have as part of Spotify is absolutely much larger.
[00:41:49.080 --> 00:41:59.320] Spotify has these crazy ambitions and they've been very public about how they want, how big they want their ad business to be and how important podcasting is to that bet.
[00:42:00.360 --> 00:42:12.920] And so, if you fast forward a few years, as like, you know, they execute on that, they, we execute on that plan, um, you know, the impact is just ginormous.
[00:42:12.920 --> 00:42:15.040] And what Chartable was this small company?
[00:42:14.680 --> 00:42:21.280] We were absolutely limited by our resources, we could only do what we could do with our budget and with our you know headcount.
[00:42:21.520 --> 00:42:25.120] And uh, we're absolutely getting you know, we have two new hires starting next week.
[00:42:25.120 --> 00:42:29.440] We have other open roles, like it's really exciting to like get a little bit of that rocket fuel, right?
[00:42:29.440 --> 00:42:32.960] Yeah, and the trade-off is that I'm not in charge anymore.
[00:42:33.120 --> 00:42:49.840] You know, there's a I am not the CEO of Spotify, yeah, and uh, you know, so like we're we're simultaneously like trying to like step on the jazz in terms of like what we can do as Chartable, but also figure out what it means to exist within this larger company.
[00:42:49.840 --> 00:42:54.240] And you know, we're one piece of like a very big puzzle, yeah, right.
[00:42:54.240 --> 00:43:01.840] Um, so there's there's kind of like there's there's pluses and minuses, there's like things that are harder, things that are easier.
[00:43:01.840 --> 00:43:09.680] Yeah, uh, the antisential dread being gone, that's quite valuable to me, yeah, yeah, honestly, better for my team, better for my family.
[00:43:09.680 --> 00:43:17.600] It's like I don't, you know, I don't have to like uh wake up every morning or in the middle of the night with that like sweat, right?
[00:43:17.600 --> 00:43:20.960] You're sleeping better, oh, yeah, oh, good.
[00:43:20.960 --> 00:43:27.280] Uh, because I, I mean, you know, uh, based on where I was at the end, um, my sleep was extremely poor, yeah.
[00:43:27.360 --> 00:43:30.960] And so, uh, any advice, any advice for sleep?
[00:43:31.280 --> 00:43:32.960] I don't know if you think you want it from me.
[00:43:32.960 --> 00:43:35.520] I mean, I sleep quite well right now.
[00:43:35.520 --> 00:43:37.280] I, as soon as transistor, good for you, man.
[00:43:37.520 --> 00:44:02.280] As soon as transistor was that's an interesting, I think it's one reason I'm so excited about this idea of you know, the market provides most of the momentum for a company, and riding the right wave is so important because the other things I tried, I was able to get to a place where, you know, this is making enough money for my family to live and it's great.
[00:43:59.840 --> 00:44:06.680] But what didn't go away was staying up all night, thinking about ideas.
[00:44:06.840 --> 00:44:08.200] What do I got to launch next?
[00:44:08.200 --> 00:44:09.480] What do I got to do next?
[00:44:09.800 --> 00:44:12.520] Once transistor was working, I slept way better.
[00:44:12.520 --> 00:44:16.520] I still sometimes wake up at four in the morning, but it's not with dread.
[00:44:16.520 --> 00:44:18.040] It's more like excitement.
[00:44:18.040 --> 00:44:20.680] It's like, oh, wow, I just get fired up.
[00:44:20.680 --> 00:44:26.360] I'm wondering if you have any advice for other companies that might get acquired in the future.
[00:44:26.360 --> 00:44:34.360] How could, what can they do now to prepare to make that due diligence time less of a nightmare?
[00:44:34.360 --> 00:44:36.200] Or is it just you just got to go through it?
[00:44:36.200 --> 00:44:37.720] It's just always going to be difficult.
[00:44:37.720 --> 00:44:39.000] You can definitely prepare.
[00:44:39.000 --> 00:44:43.240] You know, for me, I'm not a, I'm not a trained business person.
[00:44:43.240 --> 00:44:43.720] Yeah.
[00:44:44.040 --> 00:44:51.960] And so the financial side of it was something that I had to prepare kind of like during prep for the process and during the process.
[00:44:51.960 --> 00:44:55.160] So all that kind of like really boring stuff, to me, very boring.
[00:44:55.160 --> 00:44:55.720] Yeah.
[00:44:55.960 --> 00:45:08.120] Stuff like having a solid, you know, solid accounting, bookkeeping, revenue model, tax stuff, making sure all that stuff is super clean and ready to share.
[00:45:08.280 --> 00:45:09.880] It's really important, right?
[00:45:09.880 --> 00:45:10.280] Yeah.
[00:45:10.280 --> 00:45:17.640] I spent many hours on it when I would have rather been working on product kind of because I was like cramming it all into a very short time, right?
[00:45:17.640 --> 00:45:24.520] Not that we hadn't like, you know, had some books or whatever, but it wasn't, it didn't feel as important, you know, to me when I was like flying on my own.
[00:45:24.520 --> 00:45:25.640] So get a bookkeeper.
[00:45:25.640 --> 00:45:28.360] Get a really good bookkeeper and pay attention.
[00:45:28.360 --> 00:45:30.040] This is totally like way in the weeds.
[00:45:30.040 --> 00:45:35.080] But for example, what you count as like cost of goods sold versus RD expense.
[00:45:35.080 --> 00:45:36.040] That stuff matters, right?
[00:45:36.040 --> 00:45:39.640] When people are figuring out how you fit into their financial models.
[00:45:39.640 --> 00:45:42.600] What do you count as cost of goods sold with the SaaS business?
[00:45:42.840 --> 00:45:53.200] Like hosting, not all the hosting, like hosting for like, you know, the kind of paid portion of the site versus like the marketing site is marketing expense, right?
[00:45:53.920 --> 00:45:58.400] All these kinds of classifications, like your kind of financial partners might not necessarily know your business.
[00:45:58.400 --> 00:45:59.920] They don't know your business as well as you do.
[00:45:59.920 --> 00:46:00.240] Yeah.
[00:46:00.240 --> 00:46:00.560] Right.
[00:46:00.560 --> 00:46:06.400] So like knowing what to, what to put where, you know, some of it is like very much cut and dry.
[00:46:06.400 --> 00:46:09.840] This is what the IRS says, or this is what, you know, the government says.
[00:46:09.840 --> 00:46:12.320] But a lot of it is like, well, what does it mean for your business?
[00:46:12.320 --> 00:46:12.880] Right.
[00:46:13.440 --> 00:46:20.400] How do you use this particular piece of software or this other service to support your customers, right?
[00:46:20.400 --> 00:46:22.000] Or to acquire new customers.
[00:46:22.000 --> 00:46:27.760] And then like understanding the levers of the business, like how, you know, you seem to know a lot about SEO, for example, Justin.
[00:46:27.760 --> 00:46:28.800] You do a great job.
[00:46:28.800 --> 00:46:34.960] Understanding how, like, how you can model growth in the future and telling that story is a big piece.
[00:46:34.960 --> 00:46:44.080] And we certainly had our own models, but with the kind of level of rigor that potential acquirers might want to see is more than you would use internally.
[00:46:44.080 --> 00:46:44.480] Yeah.
[00:46:44.480 --> 00:46:44.800] Right.
[00:46:45.440 --> 00:46:51.280] Having something to guide a product roadmap is very different than having something to present to a finance team.
[00:46:51.280 --> 00:46:51.680] Yes.
[00:46:51.840 --> 00:46:53.200] Or to an investor, even.
[00:46:53.840 --> 00:46:55.360] You know, the level of rigor is different.
[00:46:55.920 --> 00:46:58.240] How did you make that process more equal?
[00:46:58.240 --> 00:47:01.040] Because Spotify is a massive organization.
[00:47:01.040 --> 00:47:02.640] You're a small little team.
[00:47:02.640 --> 00:47:06.960] Did you, you just had a lawyer on your side, some finance people on your side?
[00:47:06.960 --> 00:47:07.920] Yeah, we had a great team.
[00:47:07.920 --> 00:47:09.040] We had a great lawyer.
[00:47:09.040 --> 00:47:16.320] We hired an investment banker, this guy at Yale Yee, and who's great and who's been behind a lot of podcast deals.
[00:47:16.320 --> 00:47:16.880] Okay, interesting.
[00:47:16.880 --> 00:47:19.040] Who really helped us understand the process?
[00:47:19.040 --> 00:47:24.160] You know, we had all these different partners that supported us and they would come on the calls when needed.
[00:47:24.800 --> 00:47:27.840] But ultimately, if you're the CEO, it's mostly on you.
[00:47:27.840 --> 00:47:28.240] Yeah.
[00:47:28.240 --> 00:47:28.800] Right.
[00:47:29.120 --> 00:47:30.840] You're kind of driving the process.
[00:47:31.160 --> 00:47:40.360] It's definitely, it's kind of hard to speak about in the abstract, but there's plenty of good resources out there.
[00:47:40.760 --> 00:47:44.120] And, you know, for me, it was definitely something that I learned so much by doing.
[00:47:44.360 --> 00:47:47.720] I feel like I went to business school in like a really short time.
[00:47:47.720 --> 00:47:47.960] Yeah.
[00:47:47.960 --> 00:47:48.120] Yeah.
[00:47:48.920 --> 00:47:49.400] Right.
[00:47:49.400 --> 00:47:49.880] Yeah.
[00:47:49.880 --> 00:47:51.000] I can see that being stressed.
[00:47:51.560 --> 00:47:54.200] That is an understatement of a century for me.
[00:47:55.640 --> 00:47:57.480] So let's talk about podcasting.
[00:47:58.120 --> 00:48:02.280] First, I want to know what are you excited about doing with Chartable?
[00:48:02.280 --> 00:48:05.800] What's this next kind of phase look like?
[00:48:05.800 --> 00:48:11.080] And then second, let's talk about the podcast industry in general, where you think it's going.
[00:48:11.640 --> 00:48:14.920] You know, what are the next five, 10 years?
[00:48:14.920 --> 00:48:16.600] So let's start with Chartable.
[00:48:16.600 --> 00:48:19.560] What are you excited about building now with Chartable?
[00:48:19.560 --> 00:48:28.520] Yeah, the big things we're doing as part of Spotify is just doubling down on building tools for publishers, help them understand and grow audience.
[00:48:28.840 --> 00:48:32.680] And that's how we fit into the Spotify picture.
[00:48:32.680 --> 00:48:54.600] And so we're really excited about leveraging microphone data, leveraging Spotify data to give publishers a better understanding of what's happening with their shows, who's in their audience, and tools to, we have these smart links and smart promos like web to podcast attribution, podcast to podcast attribution that folks use for marketing their podcast every day.
[00:48:54.600 --> 00:48:58.680] We want to really make those just like unstoppable tools.
[00:49:00.280 --> 00:49:04.040] And we think that leveraging some of the Spotify data to do that will be great.
[00:49:04.040 --> 00:49:08.440] I don't know how much detail I can go into, but we're planning on improving them.
[00:49:08.440 --> 00:49:13.720] Will it continue to be agnostic in terms of also providing data from Apple?
[00:49:13.720 --> 00:49:14.760] And is that the plan?
[00:49:15.040 --> 00:49:26.160] I can't speak to what Apple is going to let us do or not do, but our plan is to keep the tool as agnostic as it can be and to offer it to all podcasters, even if you don't host on Microphone.
[00:49:26.880 --> 00:49:49.680] But you can imagine that Spotify has data for what happens on Spotify so that our insights into what happens within the Spotify world will be available to folks who publish their podcast to Spotify and we'll have extra tools for folks that the audience that happens on Spotify.
[00:49:50.000 --> 00:49:59.360] This opens up a whole new spectrum of possibility for you because Spotify has demographic data that you've never been able to access before, right?
[00:49:59.360 --> 00:50:08.000] So you've got what they're listening to, what country they're in, age, like there's a bunch of other.
[00:50:08.000 --> 00:50:08.640] Yep.
[00:50:08.640 --> 00:50:11.600] You must be really excited about that possibility.
[00:50:11.600 --> 00:50:12.800] We're really excited, right?
[00:50:12.800 --> 00:50:14.080] And it's certainly a process.
[00:50:14.080 --> 00:50:20.480] Like we want to make sure that we honor Charitables contractual commitments to our publishers about and to listeners about privacy.
[00:50:20.480 --> 00:50:26.160] And Spotify has like really strong privacy frameworks, like really intense processes, right?
[00:50:26.160 --> 00:50:27.760] So there's a lot to do.
[00:50:27.760 --> 00:50:37.680] I wouldn't say that we're done with it, but we've spent a lot of the first like chunk of our time within Spotify, kind of working through those legal processes to make sure that everything is in the clear.
[00:50:37.680 --> 00:50:39.440] But I'm so excited about it, right?
[00:50:39.440 --> 00:50:48.240] Because we're a data company and love putting, you know, giving podcasters data that'll help them grow their shows.
[00:50:48.240 --> 00:50:51.040] And we're getting close, man.
[00:50:51.280 --> 00:50:55.600] Can you tell me a quick, like, what's an example story of this?
[00:50:55.600 --> 00:51:04.600] Like, is it that I'm going to have a podcast and I'm going to want to know which show I should do a promo swap with?
[00:50:59.520 --> 00:51:10.360] And so you're going to be able to better identify the shows that I should do a promo swap with?
[00:51:10.360 --> 00:51:12.680] Like, you're going to surface that kind of information?
[00:51:12.680 --> 00:51:14.280] That's that's one potential story.
[00:51:14.280 --> 00:51:15.240] Like, I don't know.
[00:51:15.240 --> 00:51:21.800] Um, you know, in the short term, the goal is just to like make things kind of like quicker and easier for folks.
[00:51:21.800 --> 00:51:24.040] Like, for example, like, we were part of Megaphone.
[00:51:24.040 --> 00:51:27.080] We can make like a lot of chartable customers and Megaphone customers.
[00:51:27.080 --> 00:51:37.640] We can make the kind of like tight integration between Chartable and Megaphone that will just make people's day-to-day, like the marketing audience development people that have to live in Chartable and Megaphone make their lives really easy.
[00:51:37.640 --> 00:51:38.920] And that's what we're shipping in the short term.
[00:51:39.000 --> 00:51:39.240] Got it.
[00:51:39.240 --> 00:51:39.400] Right.
[00:51:39.480 --> 00:51:43.880] Just like kind of like improving the flows.
[00:51:43.880 --> 00:51:47.400] Like Chartable as an independent company, we have like so many steps to get anything done.
[00:51:47.400 --> 00:51:47.800] Yeah.
[00:51:47.800 --> 00:51:53.160] And, you know, for the folks that are within, you know, the kind of Spotify fold, we can make their day-to-day much better.
[00:51:53.160 --> 00:52:02.600] But yes, you can imagine in the longer term offering folks like, yeah, better ways to grow their audience and leveraging demographic data to do that.
[00:52:02.600 --> 00:52:03.160] Yeah.
[00:52:04.440 --> 00:52:09.480] And, you know, we have to like finish our processes before I can promise anything.
[00:52:09.480 --> 00:52:12.120] But yeah, your story is not far off.
[00:52:12.120 --> 00:52:16.680] Like ultimately, our job is to help people understand and grow.
[00:52:16.680 --> 00:52:17.000] Yeah.
[00:52:17.000 --> 00:52:17.160] Right.
[00:52:17.160 --> 00:52:19.960] And promo is just such a big part of growing a show.
[00:52:19.960 --> 00:52:20.520] Yeah.
[00:52:20.520 --> 00:52:25.640] And whether it's promo within your own network, which is like a huge use case, right?
[00:52:27.080 --> 00:52:30.200] Or promo across networks, across shows.
[00:52:30.200 --> 00:52:33.480] And it doesn't have, and it's not just like these gigantic networks that are doing this.
[00:52:33.480 --> 00:52:37.320] It's like even shows getting a modest number of downloads can benefit from promo, right?
[00:52:37.320 --> 00:52:39.240] So, and we want to make sure that we're serving those folks too.
[00:52:39.240 --> 00:52:39.880] Yeah.
[00:52:40.200 --> 00:52:48.560] What, uh, to end, what do you think are some things about the podcast industry that I'm missing?
[00:52:50.480 --> 00:52:57.840] What do you think I'm not seeing as indie bootstrapper Justin?
[00:52:57.840 --> 00:53:00.480] What am I not seeing that maybe I should be thinking about?
[00:53:00.480 --> 00:53:08.160] I don't know how much of your, I think there's a big international story about podcasting, which is not like a hidden secret or anything.
[00:53:08.320 --> 00:53:10.960] Chartable was very US-centric.
[00:53:11.600 --> 00:53:15.120] Spotify is a global company and has global ambitions, right?
[00:53:15.120 --> 00:53:31.920] And so it's cool to, you know, now that we have more resources and are part of this bigger team, to think about what does it mean to serve audiences and to serve publishers that are outside our very US-centric bubble.
[00:53:32.240 --> 00:53:36.800] And I think the growth story for international markets is just like amazing.
[00:53:36.800 --> 00:53:37.120] Yeah.
[00:53:37.120 --> 00:53:37.520] Right.
[00:53:37.520 --> 00:53:39.840] And there's all kinds of challenges to serve them, right?
[00:53:39.840 --> 00:53:41.040] There's language challenges.
[00:53:41.040 --> 00:53:42.640] There's like, is the ad market there?
[00:53:42.640 --> 00:53:44.480] Like, you know, all these different things, right?
[00:53:45.040 --> 00:53:58.160] But as far as something I'm really excited about, and that would have been super hard for us and maybe hard for you guys as a bootstrap company, like international, I think, absolute mega trend over the next like five to 10 years, right?
[00:53:58.160 --> 00:53:59.760] And we'll be interesting to see how it plays out.
[00:53:59.760 --> 00:54:04.800] Yeah, that's interesting because now you have this perspective with Spotify.
[00:54:04.800 --> 00:54:08.240] I always think about the shrouded ceiling.
[00:54:08.240 --> 00:54:15.200] Like we know the glass ceiling you can see above you, but the shrouded ceiling is like, there's just all this world of possibility that you don't even see.
[00:54:15.520 --> 00:54:25.760] And I think the exciting thing for you would be, again, you get to go into this company, you go, oh, well, we've got all this data and we've got all this experience.
[00:54:25.760 --> 00:54:28.000] And yeah, that's fascinating.
[00:54:28.000 --> 00:54:30.680] Well, Dave, I'm going to let you go.
[00:54:30.680 --> 00:54:31.240] Thanks so much.
[00:54:32.200 --> 00:54:33.480] I wish we could keep going.
[00:54:33.640 --> 00:54:34.600] I got to jump to you.
[00:54:29.840 --> 00:54:37.160] I want to just say thank you for having me on.
[00:54:37.320 --> 00:54:43.080] Congrats to you and John for all the amazing progress that you've made and the amazing things that you've built.
[00:54:43.080 --> 00:54:45.400] And looking forward to doing it again soon, man.
[00:54:45.400 --> 00:54:46.120] Well, congrats to you.
[00:54:46.360 --> 00:54:49.240] I'm really pleased for you and your team.
[00:54:49.480 --> 00:54:53.160] I just so glad that you were able to have that exit.
[00:54:53.160 --> 00:54:56.120] Couldn't have happened to nicer people in the industry.
[00:54:56.120 --> 00:54:56.760] So congrats.
[00:54:56.760 --> 00:54:57.720] It's very kind of you to say.
[00:54:57.720 --> 00:54:58.520] Thank you very much.
[00:54:58.520 --> 00:54:58.920] All right.
[00:54:58.920 --> 00:54:59.640] Thanks.
[00:54:59.640 --> 00:55:00.600] Talk to you later.
[00:55:00.600 --> 00:55:00.920] All right.
[00:55:00.920 --> 00:55:01.800] Thanks, Justin.
[00:55:01.800 --> 00:55:05.160] Thanks for listening and thanks to our Patreon supporters.
[00:55:05.160 --> 00:55:35.880] We have Jason Charnes, Mitchell Davis, Marcel Folle, Alex Payne, Bill Kondo, Anton Zorin, Harris Kenney, Oleg Kulig, Ethan Gunderson, Ward Sandler, Russell Brown, Noah Prale, Colin Gray, Austin Lovelace, Michael Sitver, Paul Jarvis, and Jack Ellis, Dan Buda, Darby Frey, Adam Duvander, Dave Junta, and Kyle Fox from getrewardful.com.
[00:55:35.880 --> 00:55:37.560] See you next time.
[00:55:54.680 --> 00:55:58.520] Podcast hosting is provided by transistor.fm.
[00:55:58.520 --> 00:56:09.800] They host our mp3 files, generate our RSS feed, provide us with analytics, and help us distribute the show to Spotify, Apple Podcasts, and more.
[00:56:09.800 --> 00:56:21.120] If you want to start your own podcast or you want to switch to Transistor, go to transistor.fm/slash Justin and get 15% off your first year.

Prompt 2: Key Takeaways

Now please extract the key takeaways from the transcript content I provided.

Extract the most important key takeaways from this part of the conversation. Use a single sentence statement (the key takeaway) rather than milquetoast descriptions like "the hosts discuss...". 

Limit the key takeaways to a maximum of 3. The key takeaways should be insightful and knowledge-additive. 

IMPORTANT: Return ONLY valid JSON, no explanations or markdown. Ensure:
- All strings are properly quoted and escaped
- No trailing commas
- All braces and brackets are balanced
Format: {"key_takeaways": ["takeaway 1", "takeaway 2"]}

Prompt 3: Segments

Now identify 2-4 distinct topical segments from this part of the conversation.

For each segment, identify:
- Descriptive title (3-6 words)  
- START timestamp when this topic begins (HH:MM:SS format)
- Double check that the timestamp is accurate - a timestamp will NEVER be greater than the total length of the audio
- Most important Key takeaway from that segment. Key takeaway must be specific and knowledge-additive.
- Brief summary of the discussion

IMPORTANT: The timestamp should mark when the topic/segment STARTS, not a range. Look for topic transitions and conversation shifts.

Return ONLY valid JSON. Ensure all strings are properly quoted, no trailing commas:
{
  "segments": [
    {
      "segment_title": "Topic Discussion", 
      "timestamp": "01:15:30",
      "key_takeaway": "main point from this segment",
      "segment_summary": "brief description of what was discussed"
    }
  ]
}

Timestamp format: HH:MM:SS (e.g., 00:05:30, 01:22:45) marking the START of each segment.

Prompt 4: Media Mentions

Now scan the transcript content I provided for ACTUAL mentions of specific media titles:

Find explicit mentions of:
- Books (with specific titles)
- Movies (with specific titles)  
- TV Shows (with specific titles)
- Music/Songs (with specific titles)

DO NOT include:
- Websites, URLs, or web services
- Other podcasts or podcast names

IMPORTANT: 
- Only include items explicitly mentioned by name. Do not invent titles.
- Valid categories are: "Book", "Movie", "TV Show", "Music"
- Include the exact phrase where each item was mentioned
- Find the nearest proximate timestamp where it appears in the conversation
- THE TIMESTAMP OF THE MEDIA MENTION IS IMPORTANT - DO NOT INVENT TIMESTAMPS AND DO NOT MISATTRIBUTE TIMESTAMPS
- Double check that the timestamp is accurate - a timestamp will NEVER be greater than the total length of the audio
- Timestamps are given as ranges, e.g. 01:13:42.520 --> 01:13:46.720. Use the EARLIER of the 2 timestamps in the range.

Return ONLY valid JSON. Ensure all strings are properly quoted and escaped, no trailing commas:
{
  "media_mentions": [
    {
      "title": "Exact Title as Mentioned",
      "category": "Book",
      "author_artist": "N/A",
      "context": "Brief context of why it was mentioned",
      "context_phrase": "The exact sentence or phrase where it was mentioned",
      "timestamp": "estimated time like 01:15:30"
    }
  ]
}

If no media is mentioned, return: {"media_mentions": []}

Full Transcript

[00:00:00.240 --> 00:00:03.440] This podcast is hosted by Transistor.fm.
[00:00:18.160 --> 00:00:21.520] Hello and welcome to Build Your SAS.
[00:00:21.520 --> 00:00:25.760] This is the behind-the-scenes story of building web apps in 2022.
[00:00:25.760 --> 00:00:38.400] I'm Justin Jackson from Transistor, and today on the program, I have Dave Zorob, who is the founder, co-founder of Chartable, which was recently acquired by Spotify.
[00:00:38.400 --> 00:00:46.800] Lots of great discussion in here, especially since Dave chose the venture capital route and Transistor chose the bootstrapped route.
[00:00:46.800 --> 00:00:58.880] And it's just interesting to contrast those two and to talk a little bit about, yeah, the Chartable exit, the acquisition with Spotify, and a bunch of other topics.
[00:00:58.880 --> 00:01:00.160] It's a really great episode.
[00:01:00.160 --> 00:01:01.280] I think you'll enjoy it.
[00:01:01.280 --> 00:01:02.880] Let's get into it.
[00:01:03.600 --> 00:01:09.120] Have you started going into the Spotify office or is the megaphone office remote?
[00:01:09.360 --> 00:01:10.640] I go in like once a week.
[00:01:10.640 --> 00:01:12.480] Yeah, so Spotify has worked from anywhere.
[00:01:12.720 --> 00:01:13.120] Okay.
[00:01:13.280 --> 00:01:19.040] So they've like, you know, during the pandemic, totally committed to this remote culture.
[00:01:19.040 --> 00:01:19.760] Got it.
[00:01:19.760 --> 00:01:22.560] My understanding is that it was actually pretty different prior to the pandemic.
[00:01:22.560 --> 00:01:23.920] I mean, I obviously wasn't there.
[00:01:23.920 --> 00:01:28.160] So, but you know, they have this absolutely gorgeous office.
[00:01:28.160 --> 00:01:28.560] I've been there.
[00:01:28.720 --> 00:01:29.600] Downtown Manhattan.
[00:01:29.760 --> 00:01:30.400] It's amazing.
[00:01:30.400 --> 00:01:30.720] Yeah.
[00:01:31.120 --> 00:01:31.600] The view.
[00:01:31.920 --> 00:01:33.040] It's really amazing.
[00:01:33.040 --> 00:01:35.360] Like the view of the water is.
[00:01:35.680 --> 00:01:37.280] I was like, it's crazy.
[00:01:37.280 --> 00:01:42.080] I remember they brought me up to, I mean, I'm a country kid.
[00:01:42.080 --> 00:01:45.520] I grew up in this little farm town in Alberta.
[00:01:45.520 --> 00:01:49.520] And I was meeting a few people there that day.
[00:01:49.520 --> 00:01:52.720] And I've only been, I had only been to New York once before that.
[00:01:52.720 --> 00:01:57.040] So I remember just going into that building and they're like, you're going to have to check in.
[00:01:57.040 --> 00:01:58.400] And so there's like security guards.
[00:01:58.480 --> 00:01:59.760] I had to check in there.
[00:02:00.040 --> 00:02:05.240] And then they bring me up to another place in the elevator.
[00:02:05.240 --> 00:02:08.680] And then it's like this massive waiting room.
[00:02:08.680 --> 00:02:09.880] And then they're like, oh, yeah.
[00:02:09.880 --> 00:02:10.920] And then they check on the computer.
[00:02:11.000 --> 00:02:13.480] They're like, oh, yeah, you're meeting with Bill.
[00:02:13.480 --> 00:02:15.480] And then you're meeting with, okay, yeah, sure.
[00:02:15.480 --> 00:02:17.080] And then they just tell you to wait.
[00:02:17.080 --> 00:02:22.760] And in my mind, I'm thinking, this waiting room is the office.
[00:02:22.760 --> 00:02:26.040] Like, this is it, you know?
[00:02:26.680 --> 00:02:32.920] And like, maybe there's some offices on this floor, like just like around the corner or whatever.
[00:02:32.920 --> 00:02:39.160] And then I think I met with Bill first and he's like, all right, well, let's hop on the elevator.
[00:02:39.160 --> 00:02:41.400] I'm like, wait, there's more floors?
[00:02:41.400 --> 00:02:42.360] There's more.
[00:02:42.680 --> 00:02:43.960] And he's like, oh, yeah.
[00:02:43.960 --> 00:02:46.120] And so we went up and wow.
[00:02:46.600 --> 00:02:49.080] Just, it's just mind-boggling to me.
[00:02:49.080 --> 00:02:54.680] The scale for you, is there a little bit of culture shock?
[00:02:54.680 --> 00:02:56.760] Because how big was Chartable before?
[00:02:57.080 --> 00:02:57.560] For sure.
[00:02:57.560 --> 00:02:58.440] Because Chartable is like a lot of people.
[00:02:58.520 --> 00:02:59.320] I love a few people.
[00:02:59.560 --> 00:02:59.960] Yeah.
[00:03:00.280 --> 00:03:00.920] Yeah.
[00:03:01.160 --> 00:03:13.080] So it's obviously, regardless of like, you know, I think, you know, just to be totally clear, like, part of why we ended up with Spotify is that we really felt like there was like so much alignment, both from a division perspective.
[00:03:13.080 --> 00:03:15.640] I know this sounds cheesy, but it's like actually about people too, right?
[00:03:15.640 --> 00:03:19.240] Like we were like, met a lot of people throughout the lifespan of our company.
[00:03:19.240 --> 00:03:19.560] Yeah.
[00:03:19.560 --> 00:03:24.200] Some of whom were serious about buying our company and some of whom weren't, some of whom were customers, partners, whatever.
[00:03:24.200 --> 00:03:24.520] Yeah.
[00:03:24.520 --> 00:03:26.440] And we're like, these people are great, right?
[00:03:26.440 --> 00:03:30.840] And so, like, you know, the, there's tons of alignment on all this stuff.
[00:03:30.840 --> 00:03:34.360] And it's still, you know, Spotify, I think now is like 8,000 people.
[00:03:34.360 --> 00:03:35.240] Wow.
[00:03:35.240 --> 00:03:39.480] So, you know, there's a little bit of a gap in terms of numbers.
[00:03:39.480 --> 00:03:39.880] Yeah.
[00:03:39.880 --> 00:03:41.240] Just like a little bit.
[00:03:41.400 --> 00:03:43.960] Like, you know, almost three orders of magnitude.
[00:03:43.960 --> 00:03:44.800] So, you know.
[00:03:44.360 --> 00:03:44.960] Yeah.
[00:03:44.680 --> 00:03:45.000] Yeah.
[00:03:46.000 --> 00:03:54.080] That, and not the going from a small team that's kind of focused on one thing.
[00:03:54.080 --> 00:04:03.200] And even like within podcasting, Chartable was focusing on this very narrow piece, right?
[00:04:03.520 --> 00:04:13.200] And now you're in a business that is in music, it's in producing content, it's in ads.
[00:04:13.200 --> 00:04:16.080] It's like that must be so.
[00:04:16.080 --> 00:04:19.600] And even within, because you're in the megaphone division, is that right?
[00:04:19.600 --> 00:04:20.320] Yes.
[00:04:20.320 --> 00:04:20.640] Yeah.
[00:04:20.640 --> 00:04:24.640] So even megaphones business must be quite multifaceted.
[00:04:24.640 --> 00:04:26.400] There's hosting, there's analytics.
[00:04:27.440 --> 00:04:30.080] It's so, it's really complex.
[00:04:30.080 --> 00:04:34.640] Obviously, it's like a huge part of Spotify and a huge part of the podcast industry.
[00:04:34.640 --> 00:04:41.440] So yeah, it's certainly, you know, we've only been there for about three months, a little over three months, and it's absolutely like a huge learning experience.
[00:04:41.440 --> 00:04:47.360] First, like, you know, understanding how stuff works at an organization this large.
[00:04:47.360 --> 00:04:47.680] Yeah.
[00:04:47.680 --> 00:04:48.000] Right.
[00:04:48.560 --> 00:04:52.320] Because the last time I worked at a big company was like 20 years ago, my first job out of college.
[00:04:52.320 --> 00:04:52.560] Right.
[00:04:52.560 --> 00:04:54.960] So like, who are you working for then?
[00:04:55.280 --> 00:04:57.760] I worked at Microsoft right out of school.
[00:04:57.760 --> 00:04:58.480] Wow.
[00:04:58.960 --> 00:04:59.840] In Seattle.
[00:04:59.840 --> 00:05:00.080] Yeah.
[00:05:00.080 --> 00:05:04.240] In Redmond on Office.
[00:05:04.240 --> 00:05:07.200] So that was 2003, right?
[00:05:07.200 --> 00:05:07.680] Yeah.
[00:05:07.840 --> 00:05:09.680] So almost 20 years ago.
[00:05:09.680 --> 00:05:21.120] And, you know, I didn't make it all that long there, although I had, you know, it was certainly an eye-opening experience for like a 21-year-old to like see how software gets made of that skill.
[00:05:21.120 --> 00:05:22.880] But here it's like, it's pretty different, right?
[00:05:22.880 --> 00:05:27.600] Did you work for smaller companies between that?
[00:05:27.600 --> 00:05:29.280] Like before Chartable?
[00:05:29.520 --> 00:05:39.640] I left Microsoft and started a record label in San Francisco with some friends and I was doing some like consulting and then kind of like fell into startups kind of by accident.
[00:05:39.640 --> 00:05:40.760] Like that's what was the recording.
[00:05:40.920 --> 00:05:42.280] What was the record label?
[00:05:42.840 --> 00:05:45.560] I think you told me this, but it was called Tell All Records.
[00:05:45.560 --> 00:05:47.480] Yeah, so it's like a really art music label.
[00:05:47.480 --> 00:05:54.280] We put out like super weird like experimental music, like sound collage, modern composition.
[00:05:54.280 --> 00:05:54.680] Okay.
[00:05:54.680 --> 00:05:55.640] That sort of thing.
[00:05:55.640 --> 00:05:56.440] We did okay.
[00:05:56.440 --> 00:06:01.800] I think our number one record, I mean, CDs we put out back when people bought those.
[00:06:02.280 --> 00:06:02.920] Yeah.
[00:06:02.920 --> 00:06:05.000] Not a bad time to have a record company.
[00:06:05.000 --> 00:06:05.320] Yeah.
[00:06:05.320 --> 00:06:07.720] I mean, we sold 1500 CDs of our top 10.
[00:06:08.120 --> 00:06:08.600] There you go.
[00:06:08.600 --> 00:06:09.400] That was pretty good.
[00:06:09.400 --> 00:06:10.040] Yeah.
[00:06:10.840 --> 00:06:11.400] Yeah.
[00:06:11.640 --> 00:06:12.840] You know, it was a different time.
[00:06:13.000 --> 00:06:15.640] I spent all my savings for Microsoft on this thing.
[00:06:16.120 --> 00:06:18.520] And then, yeah, I kind of stumbled into startups.
[00:06:18.600 --> 00:06:32.600] You know, I moved to San Francisco to be with, hang out with friends and to play music and ended up, you know, start a story in the air, even though it was like 2004 when I moved there and was kind of still like that hangover from dot-com 1.0.
[00:06:32.840 --> 00:06:36.920] And then I kind of like found my peeps, like found, you know, people who are building stuff.
[00:06:36.920 --> 00:06:41.320] And, you know, so I worked for this company called Hot or Knopps, like early dating site.
[00:06:41.320 --> 00:06:41.800] Yeah.
[00:06:42.040 --> 00:06:53.080] I worked for, I started a startup at my first company back in 2007, doing like Facebook apps and then iOS apps, like in the dating, social networking space.
[00:06:53.080 --> 00:06:53.720] Yeah.
[00:06:54.440 --> 00:06:56.120] I worked for AngelList for a long time.
[00:06:56.120 --> 00:07:00.120] So Angelist is like a startup investor network and chatboard.
[00:07:00.280 --> 00:07:02.360] That's how I think I first heard of you.
[00:07:02.360 --> 00:07:02.680] Yeah.
[00:07:02.680 --> 00:07:04.200] It was at AngelList.
[00:07:04.200 --> 00:07:04.520] Yeah.
[00:07:04.520 --> 00:07:09.800] So I've worked at a few different places, but Angelist at the time I joined was, I think, I was the seventh person or something.
[00:07:09.800 --> 00:07:10.120] Right.
[00:07:10.120 --> 00:07:11.000] So wow.
[00:07:11.000 --> 00:07:11.560] Okay.
[00:07:12.040 --> 00:07:15.120] I was also, you know, pretty much all small companies since.
[00:07:14.840 --> 00:07:22.000] And now, you know, we started Chartable back in 2018 after leaving AngelList and trying to figure out what to build.
[00:07:22.320 --> 00:07:25.280] And, you know, we started the podcast ourselves.
[00:07:25.280 --> 00:07:28.880] I think I told this story the last time I was here, but just for those tuning in.
[00:07:28.880 --> 00:07:29.520] Yeah, yeah.
[00:07:29.840 --> 00:07:32.560] You know, my co-vander Harish and I worked together at Angelist.
[00:07:32.640 --> 00:07:36.560] We started this, started together, you know, trying to figure out what to build.
[00:07:36.560 --> 00:07:41.520] We started a podcast summarizing Hacker News, like the Y Combinator newsboard, and it just kind of took off.
[00:07:41.520 --> 00:07:43.040] And we were like, what is this?
[00:07:43.040 --> 00:07:44.560] Like, why is anyone listening to us?
[00:07:44.560 --> 00:07:44.880] Yeah.
[00:07:44.880 --> 00:07:49.360] You know, and that's what led us down the wonderful rabbit hole that is podcasting.
[00:07:49.360 --> 00:07:53.360] So, so you and Harish found Chartable in 2018.
[00:07:53.360 --> 00:07:56.400] Actually, we got to go back a little bit because we're going to fit this in post, right?
[00:07:56.400 --> 00:07:58.720] We're going to make it totally chronological and make it all make sense.
[00:07:58.720 --> 00:08:00.080] No, no, no, no.
[00:08:00.080 --> 00:08:03.520] This will be a meandering conversation.
[00:08:04.240 --> 00:08:10.480] I might give Chris a few notes, but often I just let Chris our editor.
[00:08:10.480 --> 00:08:13.760] He just decides what he thinks is interesting.
[00:08:13.760 --> 00:08:13.920] Yes.
[00:08:14.000 --> 00:08:16.000] I also, hello, Chris.
[00:08:16.160 --> 00:08:20.080] We also hired Chris to edit the Chartable podcast back when we were doing the best.
[00:08:20.560 --> 00:08:21.600] Chris is awesome.
[00:08:21.600 --> 00:08:28.800] Chris always has these one-sided conversations where people are talking to him, but he cannot respond.
[00:08:29.120 --> 00:08:30.000] Yes.
[00:08:30.960 --> 00:08:32.160] He's like, oh, that's nice.
[00:08:32.160 --> 00:08:34.960] You know, he can't say anything.
[00:08:34.960 --> 00:08:39.920] So, were you a computer guy in the beginning, or were you just a computer guy?
[00:08:39.920 --> 00:08:40.720] Still am.
[00:08:40.720 --> 00:08:46.640] So, so, because you were like a creative music kind of, you were into other stuff.
[00:08:46.720 --> 00:08:49.600] Only thing I've ever done for work is programming, right?
[00:08:49.600 --> 00:08:53.120] So, like, when I was, I started doing it when I was like a really little kid.
[00:08:53.120 --> 00:08:58.000] I don't, like, you know, I have, I know the stories that my parents tell more than I remember it myself.
[00:08:58.000 --> 00:09:02.200] I do remember like our first computer's radio shack once I hooked up to the TV.
[00:09:02.200 --> 00:09:03.480] Was it a TRS-80?
[00:09:03.480 --> 00:09:04.200] A TRS.
[00:08:59.280 --> 00:09:04.680] Oh, nice.
[00:08:59.600 --> 00:09:05.400] Yeah.
[00:08:59.680 --> 00:09:15.000] So, well, it ran basic and, you know, we had a cassette deck that would load, like, I almost said apps, programs onto it.
[00:09:15.960 --> 00:09:26.840] The funny thing about those cassettes is I remember we had that on our VIC-20, but you had to type in so much code just to get them.
[00:09:26.840 --> 00:09:38.360] It was, yeah, it was like, and even that, that idea to me, even today, that a cassette could have data on it is just mind-boggling.
[00:09:38.360 --> 00:09:38.840] Yeah.
[00:09:38.840 --> 00:09:41.720] So it goes all the way, I mean, it's literally the only thing I've ever really done.
[00:09:41.720 --> 00:09:42.040] Yeah.
[00:09:42.040 --> 00:09:45.480] You know, I've always been a computer, an indoor kid, as they say.
[00:09:45.480 --> 00:09:45.960] Yeah.
[00:09:45.960 --> 00:09:52.520] And like, you know, I was coding when I was little, you know, went to school, you know, for computer science.
[00:09:52.520 --> 00:09:59.320] Like, I, I did like, when I was in middle school, I was writing like programming tutorials and putting them on the internet with my parents' home address.
[00:10:00.280 --> 00:10:00.840] Yeah.
[00:10:00.840 --> 00:10:20.520] And I think you can still find these with my parents' home address in the text files that were the tutorials, you know, saying like, hey, if you want to like write me a letter or like buy some like, I like published a CDR of all the programs that I like had collected for my website, which was pbasit.com.
[00:10:20.520 --> 00:10:21.320] Wow.
[00:10:21.320 --> 00:10:25.000] And yeah, this is like 1994 or something, you know, so like a while ago.
[00:10:25.000 --> 00:10:29.000] And now all those text files are just like on Usenet forever or something.
[00:10:29.000 --> 00:10:29.400] Yeah.
[00:10:29.400 --> 00:10:31.320] I mean, I think they're still around.
[00:10:32.200 --> 00:10:43.480] My good friend, who was, I guess, my best man when I got married, quoted from some of the tutorials during a speech.
[00:10:43.480 --> 00:10:43.960] That's the thing.
[00:10:44.200 --> 00:10:46.160] Talking about juicy bits of code I was sharing.
[00:10:46.320 --> 00:10:46.640] Wow.
[00:10:44.840 --> 00:10:48.400] But you were, and you were selling these.
[00:10:48.720 --> 00:10:50.320] So, were you, were you at?
[00:10:50.480 --> 00:10:53.040] Yeah, so I like wrote a bunch of tutorials and I would sell.
[00:10:53.360 --> 00:10:59.280] I sold like CDRs of like all the code that, you know, people would submit their programs to be featured on the website.
[00:10:59.280 --> 00:10:59.600] Yeah.
[00:10:59.600 --> 00:11:02.080] We had like a forum with a bunch of stuff that people wrote.
[00:11:02.080 --> 00:11:03.680] And so, yeah, I would sell these CDRs.
[00:11:03.680 --> 00:11:06.240] People would like send cash to my parents' house.
[00:11:06.240 --> 00:11:08.480] That's amazing.
[00:11:08.800 --> 00:11:09.120] Yeah.
[00:11:09.120 --> 00:11:09.760] Wow.
[00:11:10.080 --> 00:11:17.360] And like I was an early Amazon affiliate, you know, back in like 1994, 95.
[00:11:17.360 --> 00:11:24.160] Like you, you know, I think I made it like a, you know, for, I think I was like, you know, in my early teens, maybe preteens.
[00:11:24.160 --> 00:11:24.640] Yeah.
[00:11:24.640 --> 00:11:27.120] It was like decent money, like a few hundred bucks here and there.
[00:11:27.120 --> 00:11:28.400] I was like, this is incredible.
[00:11:28.720 --> 00:11:30.240] You know, that is incredible.
[00:11:30.480 --> 00:11:31.680] Money I've ever seen.
[00:11:31.680 --> 00:11:40.880] I wonder, do you think, like, is that an intuition you just always had that you wanted to make money that way?
[00:11:40.880 --> 00:11:42.080] I don't know about money.
[00:11:42.080 --> 00:11:55.280] You know, I always and still, like, I don't know how much of this is, you know, learned versus just the way my brain is built, but like, I get my, I get my dopamine hits from making stuff.
[00:11:55.280 --> 00:11:55.680] Yeah.
[00:11:55.680 --> 00:12:00.720] The thing I'm pretty good at making, I'm like, much better at making computer stuff than I am at making other stuff.
[00:12:00.720 --> 00:12:01.680] I love playing music.
[00:12:01.680 --> 00:12:02.000] Yes.
[00:12:02.160 --> 00:12:05.040] You know, I'm not the best musician in the world or anything.
[00:12:05.040 --> 00:12:05.360] Yeah.
[00:12:05.360 --> 00:12:09.040] I think I'm a much better programmer than I am a musician, or much rather like product designer.
[00:12:09.360 --> 00:12:11.520] I don't know about designer, but product maker than musician.
[00:12:11.920 --> 00:12:12.560] Yes.
[00:12:12.960 --> 00:12:19.680] So but what, what, where does the attraction towards the commerce side come from?
[00:12:19.680 --> 00:12:23.840] Because there's lots of musicians who are fine, who don't start a record label.
[00:12:23.840 --> 00:14:08.080] A record label is the capitalistic manifestation of music and so i mean it's certainly a money-losing venture so it was in some ways a non-profit not yes simply by choice but like um i don't know there's something about like wanting to put stuff in the world right and and like one you know you need to like you know in music at the time in particular it felt like a retro label was a way you know record labels that i would follow had like very particular brands of the style of music they would release they would support their artists with marketing and stuff and we wanted to do that right so like there were these like small indie labels that i would totally follow and look for every new release that came out and be like hey is this good not every single one would be good but um there was like there was a vibe associated with that and so i wanted to create that sort of vibe and put that stuff in the world are there records that you released that are on spotify um we the artists like own the masters right so i think some of our artists uh like my good friend liam singer who lives in upstate new york he still has music on spotify i think his earliest records that we put out are not on there yeah i don't know that he wants the world to be like hearing them right now you know um we worked with um this guy scott so who's an amazing record uh uh recording engineer and producer he has some ambient music that's still on spotify this woman who goes by noveler now she's like really big in the new york like avant-garde music scene i haven't taught her in like 20 years we put out this record that she made a friend um you know in 2004 or something right but like uh she's has a great music career right uh playing with uh like cool ensembles and stuff it's pretty cool that you you had that experience, and now, in some ways, you're full circle now you are you are uh working for Spotify, which is big in the music game.
[00:14:08.080 --> 00:14:10.240] Yeah, we're kind of yeah back in the game.
[00:14:10.240 --> 00:14:14.400] Yeah, and i did like, you know, I did college radio and was like the music director of my college radio station.
[00:14:14.400 --> 00:14:23.440] So, there is a lot of like kind of like consonants, like echoes here between kind of my past interests and current interests and future interests, right?
[00:14:23.440 --> 00:14:27.120] There's like music and audio and tech, right?
[00:14:27.120 --> 00:14:29.200] Computers, and they're all kind of coming together, man.
[00:14:29.200 --> 00:14:30.080] It's all meant to be.
[00:14:30.160 --> 00:14:31.680] It's all meant to be.
[00:14:32.000 --> 00:14:43.200] Do you think everybody has that intuition though to want to go to the entrepreneurship side of the you do or you don't?
[00:14:43.200 --> 00:14:43.600] I don't.
[00:14:43.600 --> 00:14:44.000] I don't.
[00:14:44.000 --> 00:14:44.480] What do you think?
[00:14:44.480 --> 00:14:50.320] Well, I'm in trouble on Twitter for this at this very moment, so that's why I'm asking you.
[00:14:50.320 --> 00:14:51.840] What's the trouble, man?
[00:14:52.480 --> 00:14:58.000] I mean, I'm just exploring some ideas, and often I explore them in public.
[00:14:58.000 --> 00:15:00.800] And I think I admire you for that.
[00:15:01.120 --> 00:15:15.120] I think one of the things that's interesting, it'd be good to get your take on it, but I, you know, it does seem that entrepreneurship is interesting, even compared to any of those other things you mentioned.
[00:15:15.120 --> 00:15:16.640] Music.
[00:15:17.920 --> 00:15:22.960] Actually, entrepreneurship is very much like those things in some ways.
[00:15:22.960 --> 00:15:25.840] So, anybody can pick up a guitar.
[00:15:25.840 --> 00:15:31.680] Anybody can, in these days, anybody can release music.
[00:15:31.920 --> 00:15:33.280] Anybody can start coding.
[00:15:33.280 --> 00:15:36.320] Anybody can release tutorials on the internet.
[00:15:36.800 --> 00:15:45.840] What's interesting about that compared to other things where there's a lot of gatekeepers is not gatekeepers.
[00:15:45.840 --> 00:16:02.520] It's what's interesting about entrepreneurship compared to other competitive pursuits like the UFC or the NBA is that I can't just wake up one day and say, I want to step into the ring with Conor McGregor, right?
[00:16:02.520 --> 00:16:03.480] I can't just do that.
[00:16:03.880 --> 00:16:07.960] I can't just one day just run on the I don't know who that is, but I assume that's a UFC person.
[00:16:07.960 --> 00:16:15.880] Yeah, the problem is I use this UFC metaphor, the example, and now everyone thinks I'm like into violent sports.
[00:16:15.880 --> 00:16:16.600] Are you a UFC?
[00:16:16.680 --> 00:16:17.240] Which I'm not.
[00:16:17.880 --> 00:16:18.920] I'm not at all.
[00:16:19.160 --> 00:16:21.640] But he's a famous person who's a big fighter.
[00:16:21.640 --> 00:16:22.280] He's a big fighter.
[00:16:22.280 --> 00:16:23.480] And you can't just go fight him.
[00:16:23.480 --> 00:16:23.800] That's right.
[00:16:23.800 --> 00:16:25.960] And, or you could, maybe.
[00:16:26.440 --> 00:16:29.080] Well, you could, but they wouldn't let you.
[00:16:29.080 --> 00:16:29.960] You know what I mean?
[00:16:29.960 --> 00:16:36.040] Like, I can't just run onto the court during an NBA game and say, okay, I'm a basketball player now.
[00:16:36.040 --> 00:16:50.520] And, you know, and but entrepreneurship and music and anybody who wants to be a public programmer person, anybody can put out their shingle and say, all right, I'm an entrepreneur.
[00:16:50.520 --> 00:16:51.800] All right, I'm a musician.
[00:16:52.040 --> 00:16:56.200] All right, I'm a programmer who shares stuff on the internet.
[00:16:56.200 --> 00:17:03.720] And what's interesting about that is we are still competing with people at the highest caliber.
[00:17:03.720 --> 00:17:12.520] So you're still competing with LeBron James, but you are just some person off the street.
[00:17:12.920 --> 00:17:14.200] Yeah, you're just a guy.
[00:17:14.200 --> 00:17:15.160] I'm in my garage.
[00:17:15.160 --> 00:17:15.320] Yeah.
[00:17:15.560 --> 00:17:16.600] Making websites, man.
[00:17:16.600 --> 00:17:17.240] Yeah.
[00:17:18.200 --> 00:17:45.920] And I find that fascinating, partly because one of the things when I talk about business, one of the things I kind of explore is I say, I think actually in business, you want to look at the survivors, the survivors, the people, like survivorship bias.
[00:17:45.920 --> 00:17:56.960] We actually want that in business because statistically, the pool of people who can just put out a shingle is infinite.
[00:17:56.960 --> 00:18:03.840] Anybody on their tax return can say, well, I'm a sole proprietor and I lost $20 this year.
[00:18:03.840 --> 00:18:22.000] And so if that's true, then we, whenever we're thinking about business and we're thinking about how to do business well, we almost have to exclude that group automatically and say, well, we can't really be thinking too.
[00:18:22.000 --> 00:18:23.360] So often, you know, I'll say.
[00:18:23.680 --> 00:18:30.320] Is this the controversial part where you're like trying to like kind of separate a certain kind of business from another kind of business or a certain kind of entrepreneur from others?
[00:18:30.320 --> 00:18:34.240] I think that's the part that people got sensitive about.
[00:18:34.240 --> 00:18:42.480] I can see how people might be sensitive, but I think it's true, if only because like, you know, people's motivations and like the desired outcomes are different.
[00:18:42.480 --> 00:18:44.400] It's like, are you even playing the same game?
[00:18:44.400 --> 00:18:44.880] Yeah.
[00:18:45.120 --> 00:18:49.360] So like, to go with the sport metaphor, it's like, are we playing the same sport?
[00:18:49.360 --> 00:19:00.560] Like, if, like, if you're playing like entrepreneurship volleyball and I'm playing entrepreneurship water polo, am I, you know, are we, should we really be judged by the same rules?
[00:19:00.560 --> 00:19:00.880] Yes.
[00:19:00.880 --> 00:19:01.360] Right.
[00:19:01.360 --> 00:19:15.280] And I think that that could apply to like somebody's side project that they're doing out of total passion, zero commercial desire versus, you know, bootstrap business whose goal is to be profitable or massively profitable.
[00:19:15.280 --> 00:19:15.600] Yeah.
[00:19:15.600 --> 00:19:19.920] Versus like a venture-batched startup whose like plan is to like lose tons of money for a while.
[00:19:19.920 --> 00:19:20.320] Yes.
[00:19:20.320 --> 00:19:20.720] Right.
[00:19:21.040 --> 00:19:21.360] Yeah.
[00:19:21.360 --> 00:19:22.040] Let's, okay.
[00:19:22.040 --> 00:19:22.240] Let's.
[00:19:22.400 --> 00:19:23.840] These are like very different games.
[00:19:23.840 --> 00:19:24.080] Yeah.
[00:19:24.080 --> 00:19:24.960] Let's let's talk.
[00:19:24.960 --> 00:19:26.800] Let's dig into this a little bit.
[00:19:26.800 --> 00:19:38.520] So for you, when you were starting Chartable, outside of your business objective or your even your philosophical objective, what was your personal objective?
[00:19:38.520 --> 00:19:40.520] Like why were you starting it?
[00:19:40.520 --> 00:19:45.880] Why were you making this bet and risking your time and your energy, et cetera?
[00:19:45.880 --> 00:19:48.280] What were you hoping to get out of it personally?
[00:19:48.600 --> 00:19:55.480] I think that if I'm really honest with myself, there's a lot of ego involved.
[00:19:55.480 --> 00:20:05.400] I have been trying to build startups for a long time and had never really gotten anywhere that I could point to and say, I'm super duper proud of that.
[00:20:05.400 --> 00:20:06.680] I did that myself.
[00:20:06.680 --> 00:20:10.760] You know, that said, like, that's certainly part of it and probably more than I want to admit.
[00:20:10.760 --> 00:20:17.080] Another part of it is that, like, I'm wired to get kicks from putting stuff on the internet, right?
[00:20:17.080 --> 00:20:19.160] And making stuff that people use.
[00:20:19.880 --> 00:20:36.760] When we've stumbled upon podcasting as like a potential industry to explore, I was just totally shocked that the kind of tools available to creators were, you know, I hate to say this word, but I'll use it, like, primitive compared to what's available for other media.
[00:20:36.760 --> 00:20:43.000] Like, you know, I mentioned earlier, I do, you know, I made mobile apps in the early days of the App Store.
[00:20:43.000 --> 00:20:55.160] And really quickly, these very sophisticated tools developed for creators to, you know, I don't know if we would have taught them creators at the time, but developers to make apps and to like, you know, figure out what's working and to grow them and all that stuff.
[00:20:55.160 --> 00:20:56.040] We were just kind of shocked.
[00:20:56.280 --> 00:20:58.200] Tools like App Annie.
[00:20:58.200 --> 00:21:04.840] Yeah, App Annie, Flurry, even the early monetization networks like Admob and stuff all had a big analytics component.
[00:21:04.840 --> 00:21:05.240] Yeah.
[00:21:05.240 --> 00:21:12.040] You know, because like you put this app out there and you had no idea what was happening other than like you would get download numbers from Apple once a day.
[00:21:12.040 --> 00:21:12.440] Yeah.
[00:21:12.440 --> 00:21:12.920] Right.
[00:21:12.920 --> 00:21:13.480] Yes.
[00:21:13.480 --> 00:21:17.040] So even worse than what podcasting was when we started.
[00:21:17.440 --> 00:21:17.840] Yes.
[00:21:17.840 --> 00:21:18.240] Yeah.
[00:21:18.560 --> 00:21:19.600] Exactly.
[00:21:14.920 --> 00:21:21.680] But you know, quickly it got super sophisticated.
[00:21:21.760 --> 00:21:26.800] And I think that that helped enable what is an absolutely massive app economy.
[00:21:26.800 --> 00:21:29.680] And we were hoping to do the same for audio, for podcasting.
[00:21:29.840 --> 00:21:30.400] Podcasting.
[00:21:30.400 --> 00:21:30.640] Right.
[00:21:30.640 --> 00:21:32.640] So I got, I like making stuff, right?
[00:21:32.640 --> 00:21:34.240] That's like, that's ultimately what it comes down to.
[00:21:34.320 --> 00:21:35.920] And I want to get more into that too.
[00:21:35.920 --> 00:21:47.040] But there's still, I gotta, I just want to sit here for a second because there's a I understand the draw to want to make stuff.
[00:21:47.040 --> 00:21:49.120] I understand that completely.
[00:21:49.120 --> 00:21:54.400] I also understand the attraction to what seems like an opportunity.
[00:21:54.400 --> 00:22:05.040] Hey, there's a wave out there that seems to be growing and I want to take my surfboard and I want to paddle out and I want to try to catch that wave because it looks like a good wave.
[00:22:05.680 --> 00:22:07.680] I can understand all of that.
[00:22:08.560 --> 00:22:21.120] But, you know, for me, I still had to discuss with my spouse, you know, hey, I'm about to embark on this journey and even pre-transistor.
[00:22:21.120 --> 00:22:22.400] Like, why are you doing this?
[00:22:22.400 --> 00:22:28.400] Why don't you just try to get another job at Microsoft and climb the ladder?
[00:22:28.400 --> 00:22:31.120] And that might be better.
[00:22:31.120 --> 00:22:33.680] So what was driving you personally?
[00:22:33.680 --> 00:22:35.760] Why even play this game?
[00:22:35.760 --> 00:22:38.640] Why make these bets in the first place?
[00:22:38.640 --> 00:22:40.800] I mean, I think ego is actually a pretty good answer.
[00:22:40.800 --> 00:22:41.680] That's part of it.
[00:22:41.680 --> 00:22:50.480] Yeah, I mean, ego is probably a big chunk of it, but also like, and this is, they're probably related, but like literally, what, what makes me happy, right?
[00:22:50.480 --> 00:23:00.600] What makes me happy is, and this has always been the case since I was putting like programming tutorials on the internet like, like you know, 30 years ago, right?
[00:22:59.440 --> 00:23:03.800] Making stuff that people use makes me happy, period.
[00:22:59.760 --> 00:23:08.120] Yeah, and you get to make a lot more stuff when you start a company.
[00:23:08.120 --> 00:23:21.720] You have a much tighter loop between, hey, I have this idea that might be good, and let's find out if it's good, versus like the kind of, you know, just by its nature, any larger company has more risk.
[00:23:21.720 --> 00:23:27.160] You know, like it's risky for them to do something new, and so it has to run through all the different departments and all that stuff.
[00:23:27.160 --> 00:23:27.800] Yeah.
[00:23:27.800 --> 00:23:41.160] I remember when I joined Microsoft, I was supposed to try to fix a bug with the spell checker that's like a shared component between like Outlook and Word and all the Office stuff.
[00:23:41.480 --> 00:23:50.680] And they were like, you have to go talk to so-and-so over in Word because he owns the dialogue box that contains the spell checker settings.
[00:23:50.920 --> 00:23:53.560] It's like this guy's like life's work, basically.
[00:23:53.560 --> 00:23:53.880] Right.
[00:23:53.880 --> 00:23:54.280] Yeah.
[00:23:54.280 --> 00:23:56.600] And I'm like, I don't know that I want to be that guy.
[00:23:56.600 --> 00:24:02.680] Like, I think that's a good thing to own that to make sure that that dialogue box, that settings panel is really good.
[00:24:02.680 --> 00:24:05.640] And I'm glad that somebody really wants to do that.
[00:24:05.640 --> 00:24:06.440] Right.
[00:24:06.920 --> 00:24:13.800] But for me, I wouldn't get enough kicks out of it to like refine the dialogue box for 20 years.
[00:24:13.800 --> 00:24:14.120] Yes.
[00:24:14.120 --> 00:24:14.520] Right.
[00:24:14.840 --> 00:24:23.080] But and then there's this other iteration on top of that, which is you start this record label, which is fun.
[00:24:23.080 --> 00:24:24.360] You control things.
[00:24:24.360 --> 00:24:25.800] You get to find the artist.
[00:24:25.800 --> 00:24:27.560] You get to do the marketing.
[00:24:27.560 --> 00:24:32.920] But there was part of that that was not satisfying because you say it didn't make very much money.
[00:24:32.920 --> 00:24:33.240] Yeah.
[00:24:33.240 --> 00:24:39.560] I mean, I spent all the saving money I saved up, uh, and um, we weren't able to do it anymore because we ran out of money.
[00:24:39.560 --> 00:24:40.120] Right.
[00:24:40.120 --> 00:24:42.760] You know, going back to the idea of the different paths, right?
[00:24:42.760 --> 00:24:51.200] Side project versus bootstrap versus like a venture, and these are not the only options, but there are a few of the many available options for making something on the internet.
[00:24:51.520 --> 00:24:55.600] It was not sustainable for something to just keep eating money, yeah.
[00:24:55.600 --> 00:24:58.400] And there's no way anyone was going to invest in our art label.
[00:24:58.400 --> 00:24:59.440] I didn't even think about it.
[00:24:59.440 --> 00:25:01.280] Yeah, yeah, yeah, yeah.
[00:25:01.280 --> 00:25:02.640] Uh, so like, what's the goal?
[00:25:02.640 --> 00:25:06.080] What's, you know, what you know, I was too young to have like really thought it through.
[00:25:06.080 --> 00:25:08.640] We just thought it would be something cool to do and something fun to work on with friends.
[00:25:08.640 --> 00:25:09.120] Yeah, right.
[00:25:09.120 --> 00:25:11.360] Well, I mean, I, and I've been, I've been there.
[00:25:11.680 --> 00:25:13.360] I know that feeling.
[00:25:13.360 --> 00:25:21.440] I think one thing I'm just, and I think this will, as we get into this kind of funded versus bootstrap conversation, it'll be interesting.
[00:25:21.440 --> 00:25:33.680] But the, again, the thing about business, if anybody can put out a shingle and then try it, which is great, I think what you quickly learn is that you're doing this for reasons.
[00:25:33.680 --> 00:25:34.960] I want to be creative.
[00:25:34.960 --> 00:25:36.640] I want to have freedom.
[00:25:36.640 --> 00:25:39.920] I want to have people use the things I make.
[00:25:39.920 --> 00:25:42.080] I want to, you know, all those things.
[00:25:42.400 --> 00:26:02.160] And it's very likely if I was independently wealthy, like if I was just a trust fund kid or something, maybe I wouldn't start businesses because maybe if I could just create things, I would be okay with it.
[00:26:02.160 --> 00:26:02.800] What do you think?
[00:26:02.800 --> 00:26:12.720] Do you think for you, if the economic incentive wasn't there, you would have been okay to just keep creating things if you knew you just had enough money?
[00:26:12.720 --> 00:26:13.600] It's hard to say, right?
[00:26:13.600 --> 00:26:15.600] Because I'm not a trust fund kid, you know?
[00:26:15.760 --> 00:26:19.600] And so, like, obviously, like, wanting to make money is part of it.
[00:26:19.560 --> 00:26:23.120] But, but like, money is definitely not my primary motivator.
[00:26:23.120 --> 00:26:23.840] It just isn't.
[00:26:23.840 --> 00:26:29.120] I could have, I would have made many different decisions all throughout my career, if you even want to call it that.
[00:26:29.160 --> 00:26:41.320] That uh, if money were my primary motivator, I've left great jobs a bunch of times because, like, uh, it wasn't, you know, I felt like I had something else to a different itch to scratch.
[00:26:41.320 --> 00:26:43.160] Yes, I guess we'll see.
[00:26:43.160 --> 00:26:46.760] I, I, you know, life is long, right?
[00:26:46.760 --> 00:26:51.960] Um, you know, this was an amazing outcome for me and for my team, but I'm not done yet, right?
[00:26:51.960 --> 00:26:53.720] And so, the motivations are different.
[00:26:53.720 --> 00:26:58.520] It's not the same as like literally thinking that this is like life or death.
[00:26:58.520 --> 00:27:03.000] Obviously, it wasn't life or death, it's just making a website on the internet and trying to sell it.
[00:27:03.000 --> 00:27:18.120] It felt so intense, especially the kind of the last year, year and a half of Chartable's independent existence, um, really trying to fulfill what I saw as its potential.
[00:27:18.120 --> 00:27:24.280] Yeah, uh, it felt like this like imperative, and a lot of that, you know, it's economic, right?
[00:27:24.600 --> 00:27:37.400] Um, but also just like deeply personal, you know, deeply, it's about my own baggage as a maker of things and as a person existing in the world that I felt like I really had to do this, yes, right?
[00:27:37.400 --> 00:27:39.960] Yeah, and do I feel like I still have to do it?
[00:27:39.960 --> 00:27:40.840] Yeah, I do.
[00:27:40.840 --> 00:27:43.160] Like, I'm broken in that way, right?
[00:27:43.160 --> 00:27:50.760] Like, that, uh, you know, if I were to be done, you know, I'm we have a long, a lot of work to do at Spotify.
[00:27:50.760 --> 00:27:59.720] Yeah, whenever that work is done, you know, I don't think I'm just gonna like go chill on a beach for five years, like I'm just gonna go do something else, go make something else, right?
[00:27:59.720 --> 00:28:20.000] I don't know that I could help that, yeah, you know, even if I like thought that it was like irrational, which I think it is irrational to do, um, I'm still going to probably do it because that's just that's how at this point, that feedback loop of wanting to make something and seeing it made and seeing people use it and trying to make it better and trying to sell it and trying to learn.
[00:28:21.040 --> 00:28:23.520] That's that's that's my that's my loop.
[00:28:23.520 --> 00:28:24.800] I'm addicted to it, right?
[00:28:24.800 --> 00:28:25.680] That's what I want to do.
[00:28:25.680 --> 00:28:44.080] And your comment about the timeline is so interesting because one of the things that was interesting when you and I met was we were on this path where our timelines were adjacent, and but we had we got to see the flux of that, right?
[00:28:44.080 --> 00:28:47.280] And of course, life is still playing out.
[00:28:47.280 --> 00:28:53.680] Uh, so I got to watch you make bets, and you got to watch John and I make bets.
[00:28:53.680 --> 00:29:02.720] And at different times, it felt like you know, like at the beginning, you had raised money, and so you and you and I talked about this.
[00:29:02.720 --> 00:29:09.200] It's very, it's kind of like at that point when you raise, I think you raised 1.3 initially, is that right?
[00:29:09.200 --> 00:29:12.240] Yeah, it's like uh, yeah, almost one and a half, not quite one and a half.
[00:29:12.240 --> 00:29:24.560] So you raised one and a half, and it was like you had chosen a path because at that point, you know, getting to 20k MRR wasn't like that wouldn't be good enough.
[00:29:24.560 --> 00:29:28.480] Like you had to keep, you had, you had a different path, correct?
[00:29:28.480 --> 00:29:39.840] Yeah, it was, there was a point, you know, we had thought that we were gonna like try to bootstrap it, bootstrap it, meaning like we didn't even know what we were building, bootstrap our company, right, when we quit our jobs at Angelist.
[00:29:39.840 --> 00:29:45.760] But when we fell down the podcast rabbit hole, we just thought, like, man, this opportunity is just so dang big.
[00:29:45.760 --> 00:29:50.480] And it would be foolish not to be more aggressive.
[00:29:50.800 --> 00:29:52.640] That was our thought at the time.
[00:29:52.640 --> 00:29:55.600] Now, I will say that's not the only path.
[00:29:55.600 --> 00:29:56.960] That's the path that we chose.
[00:29:57.040 --> 00:30:01.160] I'm incredibly impressed by what you and John have built.
[00:29:59.760 --> 00:30:12.200] And there's a lot of other folks building and podcasting that have been building their own way, whether that's a venture way or angel way or a self-funded way, whatever way it is, or as a side project, right?
[00:30:12.200 --> 00:30:12.760] Yeah.
[00:30:12.760 --> 00:30:15.000] You know, these are all totally valid paths.
[00:30:15.320 --> 00:30:16.840] We chose a particular path.
[00:30:16.840 --> 00:30:19.640] And once we chose, we had to commit, right?
[00:30:19.640 --> 00:30:21.400] There's no going back, right?
[00:30:22.120 --> 00:30:27.400] So that certainly changed what our company's journey looks like.
[00:30:27.400 --> 00:30:31.480] And in the end, we have an outcome that I think we can all be very happy with.
[00:30:31.480 --> 00:30:38.840] Was it the absolute world-changing $10 bazillion dollar outcome?
[00:30:38.840 --> 00:30:39.080] No.
[00:30:39.080 --> 00:30:45.640] But was it like a really important change for us and a great positive outcome for our team and our investors?
[00:30:45.640 --> 00:30:45.880] Yeah.
[00:30:45.880 --> 00:30:47.560] And that's great, you know?
[00:30:47.880 --> 00:30:48.840] And I'm really proud of that.
[00:30:48.840 --> 00:30:50.040] Yeah, well, and you should be.
[00:30:50.040 --> 00:31:00.840] I think that that's what I liked about talking to you is because it was like I could see, I mean, and there were times where I could see Dave's approaches is probably better.
[00:31:00.840 --> 00:31:11.400] Like at the beginning, when John and I were suffering and, you know, John's still working a full-time job, I had my own stuff going on, but I'm really putting all my time and energy into a transistor.
[00:31:11.400 --> 00:31:15.240] And so I had money stress and John had time stress.
[00:31:15.240 --> 00:31:20.840] Because now it's easy to like gloss over that in the past, but it's very likely the initial pain.
[00:31:20.840 --> 00:31:25.320] Well, the initial pain, it's very likely we might not have made it through that.
[00:31:25.640 --> 00:31:36.040] And I think when I've talked to other folks who have raised money, Adie Pinar is another one who he's saying he bootstrapped initially WooCommerce.
[00:31:36.040 --> 00:31:42.600] And then everything he's done since, he said, I'm never bootstrapping again because it's not fair to my family.
[00:31:43.560 --> 00:31:57.520] The idea that I would be running this thing on fumes and hoping to make it through this ring of fire unscathed is just, it's too much to ask.
[00:31:57.520 --> 00:32:02.640] There was a huge cost, you know, for me personally, for my, you know, my wife and my kids and stuff.
[00:32:02.640 --> 00:32:07.440] Like it was like, you know, to deny that I think would be, you know, dishonest, right?
[00:32:07.440 --> 00:32:08.480] It was absolutely a huge cost.
[00:32:08.480 --> 00:32:13.840] My wife, you know, you had mentioned talking to your response about before starting transistor that it's like a big change.
[00:32:13.840 --> 00:32:16.720] And we talked it through and we had some timelines.
[00:32:16.720 --> 00:32:19.600] And like, you know, given that we had a good outcome, it all makes sense.
[00:32:19.600 --> 00:32:22.320] In the retrospect, it was also a great idea, great way to go.
[00:32:22.320 --> 00:32:24.960] It absolutely could have gone a different way, right?
[00:32:24.960 --> 00:32:27.040] And it would have been, it would have felt very different.
[00:32:27.360 --> 00:32:36.560] And even, you know, especially at the end, like going through an MA process, it was very stressful.
[00:32:36.880 --> 00:32:39.200] And my kids noticed, right?
[00:32:39.200 --> 00:32:41.280] I have two, like a six-year-old and a three-year-old.
[00:32:41.360 --> 00:32:42.320] They absolutely noticed, right?
[00:32:42.320 --> 00:32:44.640] So I'm not, wasn't around very much, right?
[00:32:44.640 --> 00:32:46.320] I was here in the garage, right?
[00:32:46.720 --> 00:32:47.600] All the time.
[00:32:47.600 --> 00:32:56.640] You know, I'd wake up at like five, do some work, go in at 6:30 and get my older daughter ready for school, walk her to school, come back.
[00:32:56.640 --> 00:33:02.720] You know, it's just like, it was like, there's some weeks and months of like total grind, right?
[00:33:02.720 --> 00:33:04.080] But in retrospect, totally worth it.
[00:33:04.320 --> 00:33:13.840] Do you think raising money made the personal side, family side, less stressful because you were able to pay yourself a salary from the beginning?
[00:33:13.840 --> 00:33:15.600] Yeah, it definitely did.
[00:33:15.600 --> 00:33:20.800] I mean, we had a kind of built-in checkpoint.
[00:33:20.800 --> 00:33:24.640] I personally had one because we knew that we wanted to have a second child.
[00:33:24.640 --> 00:33:33.880] And either I would have to have something that was like, I would be okay with committing to bootstrapping and saying, okay, we're going to bootstrap this, and this is the plan.
[00:33:33.960 --> 00:33:40.440] And then I'll be making excess dollars a month within, you know, 18 months or whatever it is, or raise money or go get a job.
[00:33:40.440 --> 00:33:40.840] Yeah.
[00:33:40.840 --> 00:33:41.720] Those are my options.
[00:33:41.720 --> 00:33:42.120] Yeah.
[00:33:42.120 --> 00:33:42.440] Right.
[00:33:43.320 --> 00:33:46.760] And so that's probably influenced our decision making a little bit.
[00:33:47.320 --> 00:33:54.520] But once we were able to raise, like, yeah, like having health insurance, which, you know, you guys don't have to worry about in Canada.
[00:33:54.840 --> 00:33:56.520] Well, we have to worry about it for John.
[00:33:56.920 --> 00:33:57.720] And Jason.
[00:33:57.720 --> 00:33:59.720] We have John and Jason now.
[00:33:59.720 --> 00:34:03.640] And so Helen and I, Helen's in the UK, I'm in Canada.
[00:34:03.640 --> 00:34:05.560] And it's a lot easier.
[00:34:05.560 --> 00:34:06.120] You guys have it covered.
[00:34:06.280 --> 00:34:07.080] A lot easier.
[00:34:07.720 --> 00:34:11.720] Like all we have to worry about for Helen and I is dental and vision.
[00:34:11.720 --> 00:34:18.840] I was paying for Cobra out of pocket for my family, you know, from the time I left Angelus till we raised money.
[00:34:19.160 --> 00:34:22.360] And that was absolutely brutal, right?
[00:34:22.360 --> 00:34:24.280] It's like just totally insane.
[00:34:24.920 --> 00:34:33.720] And I imagine, you know, I imagine it has some impact on entrepreneurship in the US because like it's like thousands of dollars a month, you know, crazy.
[00:34:33.720 --> 00:34:37.000] Joe Biden, if you're listening to this, I mean, I'm sure he'd agree.
[00:34:37.000 --> 00:34:37.480] Yes.
[00:34:37.480 --> 00:34:39.080] But actually, actually, I'm sure he'd agree.
[00:34:39.080 --> 00:34:39.400] Yeah.
[00:34:39.400 --> 00:34:40.040] Is it doable?
[00:34:40.040 --> 00:34:40.600] But yeah.
[00:34:41.720 --> 00:35:01.240] To those on the other side of the house, if you're listening to this, I think that the greatest gift you could give entrepreneurship, free market economy like the United States, is health insurance because you want to give people some sort of safety net.
[00:35:01.240 --> 00:35:10.520] And I absolutely, even starting a business was definitely a massive risk, especially since I've had businesses fail.
[00:35:11.160 --> 00:35:23.920] But if I knew that, if I didn't know that I, if one of my kids got sick, I'd be able to go to the hospital and it wouldn't cost me $30,000 or $100,000 or whatever.
[00:35:23.920 --> 00:35:27.360] I don't think I would have started a business because it's too big of a risk.
[00:35:27.360 --> 00:35:30.400] Yeah, super, it is like a huge impediment.
[00:35:30.400 --> 00:35:37.760] And like for us, I basically was paying for like Cobra, which is a continuation of like your previous employer's health insurance.
[00:35:37.760 --> 00:35:39.280] And it was just crazy expensive.
[00:35:39.280 --> 00:35:41.360] And it was the only way I could make it work, right?
[00:35:41.360 --> 00:35:43.360] It's like there's really no other option.
[00:35:43.360 --> 00:35:54.080] And absolutely factored into, you know, my like very scary spreadsheet of impending doom of like whether I would have to like get a job or like give up, you know?
[00:35:54.880 --> 00:35:56.720] And it won't be the same next time, right?
[00:35:56.720 --> 00:36:10.960] Like, you know, we were fortunate enough to have a good enough outcome that if I were to do the irrational thing and to try down at some point in the very distant, hopefully very distant future, ask my wife, she hopes it's also very distant, you know, that it wouldn't be as much of a burden, right?
[00:36:11.520 --> 00:36:29.840] But it'd still be hard to, you know, it's still just like a massive cost and a scary thing, you know, with a family to think that like, well, just because like dad has a really weird brain and he really likes making things on the internet in this very particular way.
[00:36:29.840 --> 00:36:32.880] And so he's going to do this crazy thing and it's going to impact you.
[00:36:32.880 --> 00:36:34.320] Like, I don't know, that's pretty weird, man.
[00:36:34.320 --> 00:36:38.880] I don't even know that I'm, when I frame it that way, I'm like, wow, like, does that really the right thing to do?
[00:36:38.880 --> 00:36:39.360] I don't know.
[00:36:39.360 --> 00:36:39.840] Yeah.
[00:36:40.800 --> 00:37:09.080] I mean, it's so interesting to think about the in terms of a bat because one thing I was just thinking about while you were speaking is in some ways, you pre-acquisition and me right now, I think we do have a similar anxiety, which is most of my potential net worth is still locked up in this company.
[00:37:09.400 --> 00:37:22.600] And I think the benefit that profitable bootstrapped companies have is that if they are doing well, founders can take more money off the table each year just through distributions.
[00:37:22.920 --> 00:37:33.160] But like the way I describe it now is, especially since this, you know, whatever transistor is, it's, it's a, it's a, I think it's a success for a bootstrap company.
[00:37:33.160 --> 00:37:35.960] But it came to me in my 40s.
[00:37:35.960 --> 00:37:43.480] And so I say, I'm, I am poor in terms of net worth, but, but wealthy in terms of income, right?
[00:37:43.480 --> 00:38:00.680] So it's nice having a high income, but there's still this feeling of like, if this goes away, I still have that same anxiety of like I haven't taken enough off the table for this to be fine.
[00:38:00.680 --> 00:38:06.360] Now, every year that we keep going, that becomes less and less of a concern.
[00:38:06.360 --> 00:38:19.000] But the selling your company, you're basically pulling forward all you're pulling forward years and years of revenue in the future, and you're getting it now and you're able to put it away, right?
[00:38:19.000 --> 00:38:19.480] Yep.
[00:38:19.480 --> 00:38:19.960] Yep.
[00:38:19.960 --> 00:38:21.240] And it's trade-off, right?
[00:38:21.240 --> 00:38:25.560] I mean, you know, for us, it was absolutely the right thing to do.
[00:38:25.560 --> 00:38:42.040] And like, we really couldn't be happier about where we ended up and our timing, and feeling like we have the ability to like kind of go even kind of bigger with our vision for publisher tools, right?
[00:38:43.480 --> 00:38:45.440] As part of Spotify.
[00:38:44.600 --> 00:38:49.200] But yeah, you know, you want to talk to anxiety, man.
[00:38:49.360 --> 00:38:51.760] I mean, I was a mess, you know?
[00:38:52.400 --> 00:38:58.320] And that kind of existential dread is not there in the same way.
[00:38:58.320 --> 00:39:06.480] But now it's like, well, we did this thing, like we have to kind of make good on all of our promises to customers and all the things that we talked about.
[00:39:06.480 --> 00:39:08.240] Like we, we've, we have all these ideas.
[00:39:08.240 --> 00:39:11.040] We've been doing this for four plus years now.
[00:39:11.040 --> 00:39:14.800] I think our, I guess our four-year anniversary of Charlotte will be like next week or something.
[00:39:14.800 --> 00:39:15.440] Oh, nice.
[00:39:15.920 --> 00:39:17.840] And we have a lot of work to do.
[00:39:17.840 --> 00:39:22.160] And it's just, it's very different to get that work done in the larger environment.
[00:39:22.160 --> 00:39:25.040] There's like kind of, it's almost like there's more at stake.
[00:39:25.040 --> 00:39:26.800] It's not like there's more at stake for me.
[00:39:26.960 --> 00:39:33.440] Like personally, like if I screw up, then like my entire income is going to be destroyed and my family will be ruined.
[00:39:34.240 --> 00:39:40.640] But, you know, Spotify has really big ambitions for its podcast business.
[00:39:41.120 --> 00:39:44.080] And we're hoping to play a very large part of that.
[00:39:44.080 --> 00:39:45.760] And so we have to do that, right?
[00:39:45.760 --> 00:39:46.640] It's work.
[00:39:46.640 --> 00:39:47.760] It's work to be done.
[00:39:48.000 --> 00:39:51.440] And so I've kind of traded one kind of anxiety for another.
[00:39:51.440 --> 00:39:52.880] I'll absolutely take that trade.
[00:39:53.920 --> 00:39:59.280] And now my anxiety is, can we like make good on our promises, make good on the vision?
[00:39:59.280 --> 00:39:59.680] Yeah.
[00:39:59.680 --> 00:40:01.200] And, you know, so far so good.
[00:40:01.200 --> 00:40:03.040] It's still early days, right?
[00:40:03.760 --> 00:40:06.160] But it's definitely just trading.
[00:40:06.160 --> 00:40:09.600] And this is probably just another way that I'm wired is to worry about something.
[00:40:09.600 --> 00:40:09.840] Yeah.
[00:40:09.840 --> 00:40:12.320] Not worried about, okay, can we actually follow through?
[00:40:12.320 --> 00:40:12.560] Yeah.
[00:40:12.560 --> 00:40:13.040] Right.
[00:40:13.040 --> 00:40:13.600] Yeah.
[00:40:13.920 --> 00:40:16.560] Can you tell me a bit about that transition?
[00:40:16.560 --> 00:40:28.720] When I talked to John about an acquisition, his feeling is like, ah, neither of us has worked for a big company, but we've both worked for companies of 100, 200 people.
[00:40:28.720 --> 00:40:32.280] And we, we like this way more.
[00:40:29.600 --> 00:40:39.800] But every once in a while, I have a thought of like, maybe we could.
[00:40:40.120 --> 00:40:55.400] See, this is the fantasy, but I think maybe this is delusional, but maybe we could, John, maybe we could go to somewhere like Amazon or Spotify or Apple and really kick ass at that level.
[00:40:55.400 --> 00:40:57.960] That would be sort of interesting.
[00:40:59.480 --> 00:41:13.400] How was the transition for you and your team of being like you're this little unit that can execute at a certain level and you're scrappy and you're, you know, you're doing all the things?
[00:41:13.400 --> 00:41:18.200] Is that transition difficult going from small company to big company?
[00:41:18.200 --> 00:41:19.320] Do you feel more empowered?
[00:41:19.320 --> 00:41:25.720] Like, do you just feel like you've just got a bunch more gas in your tank and now, or they've given you like rocket boosters?
[00:41:25.720 --> 00:41:29.480] Like, what's the feeling inside of a bigger company?
[00:41:29.480 --> 00:41:30.920] Yeah, it's definitely a different feeling.
[00:41:30.920 --> 00:41:32.520] For me, I think there's trade-offs, right?
[00:41:32.520 --> 00:41:37.080] Like the total impacts we can have if we're able to execute.
[00:41:37.080 --> 00:41:39.960] I mean, we are able to execute because we're very capable.
[00:41:41.240 --> 00:41:49.080] But, you know, the impact we can have as part of Spotify is absolutely much larger.
[00:41:49.080 --> 00:41:59.320] Spotify has these crazy ambitions and they've been very public about how they want, how big they want their ad business to be and how important podcasting is to that bet.
[00:42:00.360 --> 00:42:12.920] And so, if you fast forward a few years, as like, you know, they execute on that, they, we execute on that plan, um, you know, the impact is just ginormous.
[00:42:12.920 --> 00:42:15.040] And what Chartable was this small company?
[00:42:14.680 --> 00:42:21.280] We were absolutely limited by our resources, we could only do what we could do with our budget and with our you know headcount.
[00:42:21.520 --> 00:42:25.120] And uh, we're absolutely getting you know, we have two new hires starting next week.
[00:42:25.120 --> 00:42:29.440] We have other open roles, like it's really exciting to like get a little bit of that rocket fuel, right?
[00:42:29.440 --> 00:42:32.960] Yeah, and the trade-off is that I'm not in charge anymore.
[00:42:33.120 --> 00:42:49.840] You know, there's a I am not the CEO of Spotify, yeah, and uh, you know, so like we're we're simultaneously like trying to like step on the jazz in terms of like what we can do as Chartable, but also figure out what it means to exist within this larger company.
[00:42:49.840 --> 00:42:54.240] And you know, we're one piece of like a very big puzzle, yeah, right.
[00:42:54.240 --> 00:43:01.840] Um, so there's there's kind of like there's there's pluses and minuses, there's like things that are harder, things that are easier.
[00:43:01.840 --> 00:43:09.680] Yeah, uh, the antisential dread being gone, that's quite valuable to me, yeah, yeah, honestly, better for my team, better for my family.
[00:43:09.680 --> 00:43:17.600] It's like I don't, you know, I don't have to like uh wake up every morning or in the middle of the night with that like sweat, right?
[00:43:17.600 --> 00:43:20.960] You're sleeping better, oh, yeah, oh, good.
[00:43:20.960 --> 00:43:27.280] Uh, because I, I mean, you know, uh, based on where I was at the end, um, my sleep was extremely poor, yeah.
[00:43:27.360 --> 00:43:30.960] And so, uh, any advice, any advice for sleep?
[00:43:31.280 --> 00:43:32.960] I don't know if you think you want it from me.
[00:43:32.960 --> 00:43:35.520] I mean, I sleep quite well right now.
[00:43:35.520 --> 00:43:37.280] I, as soon as transistor, good for you, man.
[00:43:37.520 --> 00:44:02.280] As soon as transistor was that's an interesting, I think it's one reason I'm so excited about this idea of you know, the market provides most of the momentum for a company, and riding the right wave is so important because the other things I tried, I was able to get to a place where, you know, this is making enough money for my family to live and it's great.
[00:43:59.840 --> 00:44:06.680] But what didn't go away was staying up all night, thinking about ideas.
[00:44:06.840 --> 00:44:08.200] What do I got to launch next?
[00:44:08.200 --> 00:44:09.480] What do I got to do next?
[00:44:09.800 --> 00:44:12.520] Once transistor was working, I slept way better.
[00:44:12.520 --> 00:44:16.520] I still sometimes wake up at four in the morning, but it's not with dread.
[00:44:16.520 --> 00:44:18.040] It's more like excitement.
[00:44:18.040 --> 00:44:20.680] It's like, oh, wow, I just get fired up.
[00:44:20.680 --> 00:44:26.360] I'm wondering if you have any advice for other companies that might get acquired in the future.
[00:44:26.360 --> 00:44:34.360] How could, what can they do now to prepare to make that due diligence time less of a nightmare?
[00:44:34.360 --> 00:44:36.200] Or is it just you just got to go through it?
[00:44:36.200 --> 00:44:37.720] It's just always going to be difficult.
[00:44:37.720 --> 00:44:39.000] You can definitely prepare.
[00:44:39.000 --> 00:44:43.240] You know, for me, I'm not a, I'm not a trained business person.
[00:44:43.240 --> 00:44:43.720] Yeah.
[00:44:44.040 --> 00:44:51.960] And so the financial side of it was something that I had to prepare kind of like during prep for the process and during the process.
[00:44:51.960 --> 00:44:55.160] So all that kind of like really boring stuff, to me, very boring.
[00:44:55.160 --> 00:44:55.720] Yeah.
[00:44:55.960 --> 00:45:08.120] Stuff like having a solid, you know, solid accounting, bookkeeping, revenue model, tax stuff, making sure all that stuff is super clean and ready to share.
[00:45:08.280 --> 00:45:09.880] It's really important, right?
[00:45:09.880 --> 00:45:10.280] Yeah.
[00:45:10.280 --> 00:45:17.640] I spent many hours on it when I would have rather been working on product kind of because I was like cramming it all into a very short time, right?
[00:45:17.640 --> 00:45:24.520] Not that we hadn't like, you know, had some books or whatever, but it wasn't, it didn't feel as important, you know, to me when I was like flying on my own.
[00:45:24.520 --> 00:45:25.640] So get a bookkeeper.
[00:45:25.640 --> 00:45:28.360] Get a really good bookkeeper and pay attention.
[00:45:28.360 --> 00:45:30.040] This is totally like way in the weeds.
[00:45:30.040 --> 00:45:35.080] But for example, what you count as like cost of goods sold versus RD expense.
[00:45:35.080 --> 00:45:36.040] That stuff matters, right?
[00:45:36.040 --> 00:45:39.640] When people are figuring out how you fit into their financial models.
[00:45:39.640 --> 00:45:42.600] What do you count as cost of goods sold with the SaaS business?
[00:45:42.840 --> 00:45:53.200] Like hosting, not all the hosting, like hosting for like, you know, the kind of paid portion of the site versus like the marketing site is marketing expense, right?
[00:45:53.920 --> 00:45:58.400] All these kinds of classifications, like your kind of financial partners might not necessarily know your business.
[00:45:58.400 --> 00:45:59.920] They don't know your business as well as you do.
[00:45:59.920 --> 00:46:00.240] Yeah.
[00:46:00.240 --> 00:46:00.560] Right.
[00:46:00.560 --> 00:46:06.400] So like knowing what to, what to put where, you know, some of it is like very much cut and dry.
[00:46:06.400 --> 00:46:09.840] This is what the IRS says, or this is what, you know, the government says.
[00:46:09.840 --> 00:46:12.320] But a lot of it is like, well, what does it mean for your business?
[00:46:12.320 --> 00:46:12.880] Right.
[00:46:13.440 --> 00:46:20.400] How do you use this particular piece of software or this other service to support your customers, right?
[00:46:20.400 --> 00:46:22.000] Or to acquire new customers.
[00:46:22.000 --> 00:46:27.760] And then like understanding the levers of the business, like how, you know, you seem to know a lot about SEO, for example, Justin.
[00:46:27.760 --> 00:46:28.800] You do a great job.
[00:46:28.800 --> 00:46:34.960] Understanding how, like, how you can model growth in the future and telling that story is a big piece.
[00:46:34.960 --> 00:46:44.080] And we certainly had our own models, but with the kind of level of rigor that potential acquirers might want to see is more than you would use internally.
[00:46:44.080 --> 00:46:44.480] Yeah.
[00:46:44.480 --> 00:46:44.800] Right.
[00:46:45.440 --> 00:46:51.280] Having something to guide a product roadmap is very different than having something to present to a finance team.
[00:46:51.280 --> 00:46:51.680] Yes.
[00:46:51.840 --> 00:46:53.200] Or to an investor, even.
[00:46:53.840 --> 00:46:55.360] You know, the level of rigor is different.
[00:46:55.920 --> 00:46:58.240] How did you make that process more equal?
[00:46:58.240 --> 00:47:01.040] Because Spotify is a massive organization.
[00:47:01.040 --> 00:47:02.640] You're a small little team.
[00:47:02.640 --> 00:47:06.960] Did you, you just had a lawyer on your side, some finance people on your side?
[00:47:06.960 --> 00:47:07.920] Yeah, we had a great team.
[00:47:07.920 --> 00:47:09.040] We had a great lawyer.
[00:47:09.040 --> 00:47:16.320] We hired an investment banker, this guy at Yale Yee, and who's great and who's been behind a lot of podcast deals.
[00:47:16.320 --> 00:47:16.880] Okay, interesting.
[00:47:16.880 --> 00:47:19.040] Who really helped us understand the process?
[00:47:19.040 --> 00:47:24.160] You know, we had all these different partners that supported us and they would come on the calls when needed.
[00:47:24.800 --> 00:47:27.840] But ultimately, if you're the CEO, it's mostly on you.
[00:47:27.840 --> 00:47:28.240] Yeah.
[00:47:28.240 --> 00:47:28.800] Right.
[00:47:29.120 --> 00:47:30.840] You're kind of driving the process.
[00:47:31.160 --> 00:47:40.360] It's definitely, it's kind of hard to speak about in the abstract, but there's plenty of good resources out there.
[00:47:40.760 --> 00:47:44.120] And, you know, for me, it was definitely something that I learned so much by doing.
[00:47:44.360 --> 00:47:47.720] I feel like I went to business school in like a really short time.
[00:47:47.720 --> 00:47:47.960] Yeah.
[00:47:47.960 --> 00:47:48.120] Yeah.
[00:47:48.920 --> 00:47:49.400] Right.
[00:47:49.400 --> 00:47:49.880] Yeah.
[00:47:49.880 --> 00:47:51.000] I can see that being stressed.
[00:47:51.560 --> 00:47:54.200] That is an understatement of a century for me.
[00:47:55.640 --> 00:47:57.480] So let's talk about podcasting.
[00:47:58.120 --> 00:48:02.280] First, I want to know what are you excited about doing with Chartable?
[00:48:02.280 --> 00:48:05.800] What's this next kind of phase look like?
[00:48:05.800 --> 00:48:11.080] And then second, let's talk about the podcast industry in general, where you think it's going.
[00:48:11.640 --> 00:48:14.920] You know, what are the next five, 10 years?
[00:48:14.920 --> 00:48:16.600] So let's start with Chartable.
[00:48:16.600 --> 00:48:19.560] What are you excited about building now with Chartable?
[00:48:19.560 --> 00:48:28.520] Yeah, the big things we're doing as part of Spotify is just doubling down on building tools for publishers, help them understand and grow audience.
[00:48:28.840 --> 00:48:32.680] And that's how we fit into the Spotify picture.
[00:48:32.680 --> 00:48:54.600] And so we're really excited about leveraging microphone data, leveraging Spotify data to give publishers a better understanding of what's happening with their shows, who's in their audience, and tools to, we have these smart links and smart promos like web to podcast attribution, podcast to podcast attribution that folks use for marketing their podcast every day.
[00:48:54.600 --> 00:48:58.680] We want to really make those just like unstoppable tools.
[00:49:00.280 --> 00:49:04.040] And we think that leveraging some of the Spotify data to do that will be great.
[00:49:04.040 --> 00:49:08.440] I don't know how much detail I can go into, but we're planning on improving them.
[00:49:08.440 --> 00:49:13.720] Will it continue to be agnostic in terms of also providing data from Apple?
[00:49:13.720 --> 00:49:14.760] And is that the plan?
[00:49:15.040 --> 00:49:26.160] I can't speak to what Apple is going to let us do or not do, but our plan is to keep the tool as agnostic as it can be and to offer it to all podcasters, even if you don't host on Microphone.
[00:49:26.880 --> 00:49:49.680] But you can imagine that Spotify has data for what happens on Spotify so that our insights into what happens within the Spotify world will be available to folks who publish their podcast to Spotify and we'll have extra tools for folks that the audience that happens on Spotify.
[00:49:50.000 --> 00:49:59.360] This opens up a whole new spectrum of possibility for you because Spotify has demographic data that you've never been able to access before, right?
[00:49:59.360 --> 00:50:08.000] So you've got what they're listening to, what country they're in, age, like there's a bunch of other.
[00:50:08.000 --> 00:50:08.640] Yep.
[00:50:08.640 --> 00:50:11.600] You must be really excited about that possibility.
[00:50:11.600 --> 00:50:12.800] We're really excited, right?
[00:50:12.800 --> 00:50:14.080] And it's certainly a process.
[00:50:14.080 --> 00:50:20.480] Like we want to make sure that we honor Charitables contractual commitments to our publishers about and to listeners about privacy.
[00:50:20.480 --> 00:50:26.160] And Spotify has like really strong privacy frameworks, like really intense processes, right?
[00:50:26.160 --> 00:50:27.760] So there's a lot to do.
[00:50:27.760 --> 00:50:37.680] I wouldn't say that we're done with it, but we've spent a lot of the first like chunk of our time within Spotify, kind of working through those legal processes to make sure that everything is in the clear.
[00:50:37.680 --> 00:50:39.440] But I'm so excited about it, right?
[00:50:39.440 --> 00:50:48.240] Because we're a data company and love putting, you know, giving podcasters data that'll help them grow their shows.
[00:50:48.240 --> 00:50:51.040] And we're getting close, man.
[00:50:51.280 --> 00:50:55.600] Can you tell me a quick, like, what's an example story of this?
[00:50:55.600 --> 00:51:04.600] Like, is it that I'm going to have a podcast and I'm going to want to know which show I should do a promo swap with?
[00:50:59.520 --> 00:51:10.360] And so you're going to be able to better identify the shows that I should do a promo swap with?
[00:51:10.360 --> 00:51:12.680] Like, you're going to surface that kind of information?
[00:51:12.680 --> 00:51:14.280] That's that's one potential story.
[00:51:14.280 --> 00:51:15.240] Like, I don't know.
[00:51:15.240 --> 00:51:21.800] Um, you know, in the short term, the goal is just to like make things kind of like quicker and easier for folks.
[00:51:21.800 --> 00:51:24.040] Like, for example, like, we were part of Megaphone.
[00:51:24.040 --> 00:51:27.080] We can make like a lot of chartable customers and Megaphone customers.
[00:51:27.080 --> 00:51:37.640] We can make the kind of like tight integration between Chartable and Megaphone that will just make people's day-to-day, like the marketing audience development people that have to live in Chartable and Megaphone make their lives really easy.
[00:51:37.640 --> 00:51:38.920] And that's what we're shipping in the short term.
[00:51:39.000 --> 00:51:39.240] Got it.
[00:51:39.240 --> 00:51:39.400] Right.
[00:51:39.480 --> 00:51:43.880] Just like kind of like improving the flows.
[00:51:43.880 --> 00:51:47.400] Like Chartable as an independent company, we have like so many steps to get anything done.
[00:51:47.400 --> 00:51:47.800] Yeah.
[00:51:47.800 --> 00:51:53.160] And, you know, for the folks that are within, you know, the kind of Spotify fold, we can make their day-to-day much better.
[00:51:53.160 --> 00:52:02.600] But yes, you can imagine in the longer term offering folks like, yeah, better ways to grow their audience and leveraging demographic data to do that.
[00:52:02.600 --> 00:52:03.160] Yeah.
[00:52:04.440 --> 00:52:09.480] And, you know, we have to like finish our processes before I can promise anything.
[00:52:09.480 --> 00:52:12.120] But yeah, your story is not far off.
[00:52:12.120 --> 00:52:16.680] Like ultimately, our job is to help people understand and grow.
[00:52:16.680 --> 00:52:17.000] Yeah.
[00:52:17.000 --> 00:52:17.160] Right.
[00:52:17.160 --> 00:52:19.960] And promo is just such a big part of growing a show.
[00:52:19.960 --> 00:52:20.520] Yeah.
[00:52:20.520 --> 00:52:25.640] And whether it's promo within your own network, which is like a huge use case, right?
[00:52:27.080 --> 00:52:30.200] Or promo across networks, across shows.
[00:52:30.200 --> 00:52:33.480] And it doesn't have, and it's not just like these gigantic networks that are doing this.
[00:52:33.480 --> 00:52:37.320] It's like even shows getting a modest number of downloads can benefit from promo, right?
[00:52:37.320 --> 00:52:39.240] So, and we want to make sure that we're serving those folks too.
[00:52:39.240 --> 00:52:39.880] Yeah.
[00:52:40.200 --> 00:52:48.560] What, uh, to end, what do you think are some things about the podcast industry that I'm missing?
[00:52:50.480 --> 00:52:57.840] What do you think I'm not seeing as indie bootstrapper Justin?
[00:52:57.840 --> 00:53:00.480] What am I not seeing that maybe I should be thinking about?
[00:53:00.480 --> 00:53:08.160] I don't know how much of your, I think there's a big international story about podcasting, which is not like a hidden secret or anything.
[00:53:08.320 --> 00:53:10.960] Chartable was very US-centric.
[00:53:11.600 --> 00:53:15.120] Spotify is a global company and has global ambitions, right?
[00:53:15.120 --> 00:53:31.920] And so it's cool to, you know, now that we have more resources and are part of this bigger team, to think about what does it mean to serve audiences and to serve publishers that are outside our very US-centric bubble.
[00:53:32.240 --> 00:53:36.800] And I think the growth story for international markets is just like amazing.
[00:53:36.800 --> 00:53:37.120] Yeah.
[00:53:37.120 --> 00:53:37.520] Right.
[00:53:37.520 --> 00:53:39.840] And there's all kinds of challenges to serve them, right?
[00:53:39.840 --> 00:53:41.040] There's language challenges.
[00:53:41.040 --> 00:53:42.640] There's like, is the ad market there?
[00:53:42.640 --> 00:53:44.480] Like, you know, all these different things, right?
[00:53:45.040 --> 00:53:58.160] But as far as something I'm really excited about, and that would have been super hard for us and maybe hard for you guys as a bootstrap company, like international, I think, absolute mega trend over the next like five to 10 years, right?
[00:53:58.160 --> 00:53:59.760] And we'll be interesting to see how it plays out.
[00:53:59.760 --> 00:54:04.800] Yeah, that's interesting because now you have this perspective with Spotify.
[00:54:04.800 --> 00:54:08.240] I always think about the shrouded ceiling.
[00:54:08.240 --> 00:54:15.200] Like we know the glass ceiling you can see above you, but the shrouded ceiling is like, there's just all this world of possibility that you don't even see.
[00:54:15.520 --> 00:54:25.760] And I think the exciting thing for you would be, again, you get to go into this company, you go, oh, well, we've got all this data and we've got all this experience.
[00:54:25.760 --> 00:54:28.000] And yeah, that's fascinating.
[00:54:28.000 --> 00:54:30.680] Well, Dave, I'm going to let you go.
[00:54:30.680 --> 00:54:31.240] Thanks so much.
[00:54:32.200 --> 00:54:33.480] I wish we could keep going.
[00:54:33.640 --> 00:54:34.600] I got to jump to you.
[00:54:29.840 --> 00:54:37.160] I want to just say thank you for having me on.
[00:54:37.320 --> 00:54:43.080] Congrats to you and John for all the amazing progress that you've made and the amazing things that you've built.
[00:54:43.080 --> 00:54:45.400] And looking forward to doing it again soon, man.
[00:54:45.400 --> 00:54:46.120] Well, congrats to you.
[00:54:46.360 --> 00:54:49.240] I'm really pleased for you and your team.
[00:54:49.480 --> 00:54:53.160] I just so glad that you were able to have that exit.
[00:54:53.160 --> 00:54:56.120] Couldn't have happened to nicer people in the industry.
[00:54:56.120 --> 00:54:56.760] So congrats.
[00:54:56.760 --> 00:54:57.720] It's very kind of you to say.
[00:54:57.720 --> 00:54:58.520] Thank you very much.
[00:54:58.520 --> 00:54:58.920] All right.
[00:54:58.920 --> 00:54:59.640] Thanks.
[00:54:59.640 --> 00:55:00.600] Talk to you later.
[00:55:00.600 --> 00:55:00.920] All right.
[00:55:00.920 --> 00:55:01.800] Thanks, Justin.
[00:55:01.800 --> 00:55:05.160] Thanks for listening and thanks to our Patreon supporters.
[00:55:05.160 --> 00:55:35.880] We have Jason Charnes, Mitchell Davis, Marcel Folle, Alex Payne, Bill Kondo, Anton Zorin, Harris Kenney, Oleg Kulig, Ethan Gunderson, Ward Sandler, Russell Brown, Noah Prale, Colin Gray, Austin Lovelace, Michael Sitver, Paul Jarvis, and Jack Ellis, Dan Buda, Darby Frey, Adam Duvander, Dave Junta, and Kyle Fox from getrewardful.com.
[00:55:35.880 --> 00:55:37.560] See you next time.
[00:55:54.680 --> 00:55:58.520] Podcast hosting is provided by transistor.fm.
[00:55:58.520 --> 00:56:09.800] They host our mp3 files, generate our RSS feed, provide us with analytics, and help us distribute the show to Spotify, Apple Podcasts, and more.
[00:56:09.800 --> 00:56:21.120] If you want to start your own podcast or you want to switch to Transistor, go to transistor.fm/slash Justin and get 15% off your first year.