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[00:00:00.160 --> 00:00:02.000] You're listening to Startups for the Rest of Us.
[00:00:02.000 --> 00:00:03.200] I'm Rob Walling.
[00:00:03.200 --> 00:00:06.480] In this episode, I have a conversation with Braden Dennis.
[00:00:06.480 --> 00:00:07.840] He's come back on the show.
[00:00:07.840 --> 00:00:16.560] He's the co-founder of FinChat, and they have recently rebranded to fiscal.ai after raising a $10 million Series A.
[00:00:16.880 --> 00:00:23.920] I don't cover a lot of venture raises on this podcast because we focus on bootstrapped and mostly bootstrapped companies.
[00:00:23.920 --> 00:00:38.720] But now and again, in our ecosystem, we are seeing bootstrappers who catch lightning in a bottle and they realize that the opportunity that they've stumbled upon has much more potential than they originally thought.
[00:00:38.720 --> 00:00:46.240] And some of those folks decide to sell early, some folks continue to bootstrap, and others decide to go that venture route.
[00:00:46.240 --> 00:00:53.040] And today, Brayden and I discuss that decision about why he and his co-founders decided to shoot for the moon.
[00:00:53.040 --> 00:00:58.640] As you can tell by the title, we also talk about how they shut down a $1.5 million ARR product.
[00:00:58.640 --> 00:01:01.120] And we do a quick recap of what got them here.
[00:01:01.120 --> 00:01:07.120] You can hear more of that in his prior episode, which I mentioned during the interview.
[00:01:07.120 --> 00:01:13.040] Before we dive into that conversation, I want to let you know about our MicroConf local chapters.
[00:01:13.040 --> 00:01:16.160] Building a business can be isolating, but it doesn't have to be.
[00:01:16.160 --> 00:01:25.040] So inside MicroConf Connect, which is our online membership community, we are launching local chapters to help you meet each other in person.
[00:01:25.040 --> 00:01:38.080] Our first local chapters will be taking place in Barcelona, Toronto, Sydney, Austin, and London, giving you the chance to share challenges, exchange ideas, and build relationships with other founders in your area.
[00:01:38.080 --> 00:01:42.800] Alongside these local chapters, we're also opening up the MicroConf Ambassador Program.
[00:01:42.800 --> 00:01:47.520] If you want to help bring founders together in your city, you can apply to become an ambassador.
[00:01:47.520 --> 00:01:53.920] We'll provide everything you need: a comprehensive playbook, promotional support, and swag to make your events successful.
[00:01:53.920 --> 00:01:56.560] Because no event can be successful without swag, am I right?
[00:01:56.560 --> 00:02:07.720] If you're looking for accountability, collaboration, or just a good conversations over coffee, apply to join Microconf Connect and become a part of the community to learn more about local chapters and the ambassador program.
[00:02:07.720 --> 00:02:10.760] Head to microconfconnect.com.
[00:02:10.760 --> 00:02:16.040] And with that, let's dive into my enlightening conversation with Brayden Dennis.
[00:02:22.440 --> 00:02:24.840] Braden Dennis, welcome back to the show.
[00:02:24.840 --> 00:02:25.160] Mr.
[00:02:25.160 --> 00:02:27.080] Walling, it's always good to see you.
[00:02:27.400 --> 00:02:28.520] So good to have you, man.
[00:02:28.520 --> 00:02:31.960] So you were on episode 705 of this very show.
[00:02:31.960 --> 00:02:34.760] It was March 19th of last year.
[00:02:34.760 --> 00:02:37.160] So just over, what, about 15 months ago?
[00:02:37.160 --> 00:02:46.280] And we talked about how your SaaS app called Stratosphere, how you went from bootstrapped to taking money from Tiny Seed.
[00:02:46.280 --> 00:02:49.080] So we said mostly bootstrapped, to then going venture-backed.
[00:02:49.080 --> 00:02:53.640] And I believe you had raised pre-seed round, what was it, 2 million, 3 million?
[00:02:53.640 --> 00:02:54.600] It was 1.5.
[00:02:54.600 --> 00:02:55.480] 1.5.
[00:02:55.480 --> 00:02:56.120] Okay.
[00:02:56.440 --> 00:02:58.440] And we covered a bunch of topics.
[00:02:58.840 --> 00:03:07.800] You rebranded to FinChat and have more of an AI event where you could, you know, chat with what, public market data really is the thing that you have.
[00:03:07.880 --> 00:03:10.360] How you had launched a second product, and you and I talked through.
[00:03:10.360 --> 00:03:13.640] I was like, my advice is usually not to, and when is an exception, right?
[00:03:13.640 --> 00:03:15.240] We talked through in that episode.
[00:03:15.240 --> 00:03:18.440] And then you, I mean, I guess catch us up.
[00:03:18.440 --> 00:03:20.840] You raised that venture round.
[00:03:20.840 --> 00:03:23.080] And now you've just raised another.
[00:03:23.080 --> 00:03:27.960] You've raised a $10 million Series A, which is a shload of money for a bootstrapper.
[00:03:27.960 --> 00:03:29.880] And I still think of you, I mean, you guys are moving fast.
[00:03:29.880 --> 00:03:31.080] It's a big, ambitious space.
[00:03:31.080 --> 00:03:32.920] And you're now a venture-backed company.
[00:03:32.920 --> 00:03:38.840] But, like, when you and I first met, you were a podcaster with a little B2C, you know, personal finance app.
[00:03:38.840 --> 00:03:43.640] So, catch us up on the last year and a half.
[00:03:43.640 --> 00:03:47.360] Yeah, I mean, total funding to date is now 13 million U.S.
[00:03:44.840 --> 00:03:51.360] and it sounds insane to say because it's not so long ago.
[00:03:51.680 --> 00:03:55.280] I met you for the first time in Austin, Texas, after Tiny Seed.
[00:03:55.280 --> 00:04:03.280] And yeah, I was like, okay, we're just going to take this little bit of money, me and my co-founders, we're going to, you know, try to get this to a few million in ARR.
[00:04:03.280 --> 00:04:08.640] I mean, at that point, your only goal is like a million in ARR, a million in ARR, a million in ARR.
[00:04:08.960 --> 00:04:11.280] I will be happy when I hit one million.
[00:04:11.840 --> 00:04:12.960] You're going to be happy forever.
[00:04:12.960 --> 00:04:13.760] Forever.
[00:04:14.480 --> 00:04:15.280] Forever.
[00:04:15.280 --> 00:04:16.560] I'll be fully content.
[00:04:16.560 --> 00:04:18.560] There'll be nothing wrong with the world, right?
[00:04:18.560 --> 00:04:20.400] And so, you know, that was our goal.
[00:04:20.400 --> 00:04:28.720] And then, yeah, we launched this kind of second project because almost more out of curiosity, like what can we do with an LLM API?
[00:04:28.720 --> 00:04:31.680] It took off, so then we kind of merged the products.
[00:04:31.680 --> 00:04:34.480] And then, you know, more and more has happened since then.
[00:04:34.480 --> 00:04:44.560] We've had more ambitions to like actually just like go after these big players, like go after the data infrastructure, like what we can do with AI behind the scenes.
[00:04:44.560 --> 00:04:55.440] And so we figured we'd pivot a little bit away from the chat name because people were kind of pigeonholing us to that name, doing it with the Series A makes sense.
[00:04:55.440 --> 00:05:07.440] And the prize that we were then now set on, we realized that we were going to need a significantly more amount of capital, somewhere between five and 10.
[00:05:07.440 --> 00:05:13.040] And every venture investor is like, take more and go try to get this thing.
[00:05:13.040 --> 00:05:13.840] And you know what?
[00:05:13.840 --> 00:05:16.960] I don't think that's venture investors trying to be evil.
[00:05:16.960 --> 00:05:18.000] They're actually right.
[00:05:18.000 --> 00:05:19.840] They've seen pattern recognition.
[00:05:19.840 --> 00:05:21.680] Like, you're going to need more capital.
[00:05:21.680 --> 00:05:27.520] This is AI, and you're up against people who are raising, you know, hundreds of millions of dollars in some cases.
[00:05:27.520 --> 00:05:29.200] And so, let's talk about that rebrand.
[00:05:29.200 --> 00:05:35.960] So, you're now at fiscal.ai, and your H1 is the modern financial data terminal.
[00:05:35.960 --> 00:05:43.400] Go from idea to confidence with clean, global financial data trusted by the world's leading public market investors.
[00:05:43.400 --> 00:05:45.240] And your site looks gorgeous, by the way.
[00:05:45.240 --> 00:05:47.240] It's a really nice, nice rebrand.
[00:05:47.240 --> 00:05:49.880] So, moving from FinChat to fiscal.
[00:05:49.880 --> 00:05:52.600] Well, fiscal, I mean, fiscal is a great name, especially fiscal.ai.
[00:05:52.600 --> 00:05:55.480] So, the part of that was to not be pigeonholed as just like a chat app.
[00:05:55.480 --> 00:05:56.440] Is that the idea?
[00:05:56.440 --> 00:06:02.680] Yeah, we're like, okay, we've become finance plus AI, and FinChat kind of resembled that.
[00:06:02.680 --> 00:06:07.080] But we would talk to these big bank investors, these public market investors.
[00:06:07.080 --> 00:06:11.720] We had two problems: one, they thought it was just a financial chat.
[00:06:11.720 --> 00:06:16.120] They thought we were maybe like a Bloomberg chat competitor, which was not really true.
[00:06:16.120 --> 00:06:18.280] It was like a full actual data terminal product.
[00:06:18.280 --> 00:06:24.680] So, they're like pleasantly surprised when they came to the demo, but still, like, we were underselling a bit what we were doing.
[00:06:24.680 --> 00:06:42.360] And, two, a lot of big bureaucratic financial buyers had almost all AI chat domains blocked on the server because they didn't want anyone putting in customer-sensitive information, proprietary trading data, stuff like that.
[00:06:42.360 --> 00:06:44.520] And so, we were just always blocked.
[00:06:44.520 --> 00:06:47.880] So, those first demos, no one had ever seen the product before.
[00:06:47.880 --> 00:06:50.760] And that was really hurting our go-to-market.
[00:06:50.920 --> 00:06:51.880] That makes sense.
[00:06:51.880 --> 00:06:59.640] And when, as you said, timing it with the Series A makes a lot of sense because you have the money to acquire the domain and to do the redesign.
[00:06:59.800 --> 00:07:09.160] You touched on it briefly, but I want to double-click on this thing you said of, you know, we had raised the 1.5 million and we had FinChat and it was working.
[00:07:09.160 --> 00:07:11.160] And then we decided to be more ambitious.
[00:07:11.160 --> 00:07:15.000] We decided to take on the, I forget, you know, the terminals of the world or something like that.
[00:07:15.200 --> 00:07:17.040] And that's why you raised the Series A, right?
[00:07:17.040 --> 00:07:20.640] You just need a bunch of money to do something, but tell me what that is.
[00:07:20.640 --> 00:07:22.560] Like, why do you need a bunch of money?
[00:07:22.560 --> 00:07:24.080] Is it just because the others raised it?
[00:07:24.080 --> 00:07:25.040] And who are you competing?
[00:07:25.120 --> 00:07:28.320] Like, maybe talk us through like FinChat, what is it?
[00:07:28.320 --> 00:07:29.760] What was it in 30 seconds?
[00:07:29.760 --> 00:07:36.800] And then, like, what is fiscal and how is it so different that you needed to raise eight figures of funding in order to go after that opportunity?
[00:07:36.800 --> 00:07:38.720] Yeah, it's a fantastic question.
[00:07:38.720 --> 00:07:53.280] So the landscape of our industry today is dominated by primarily three or four massive tens of billions, if not hundreds of billions, each player of market cap on the public market.
[00:07:53.280 --> 00:07:59.680] You know, some of their stocks are worth over $100 billion, many of them in tens of billions of dollars.
[00:07:59.680 --> 00:08:10.640] And so if you think about what they do, they are essentially aggregating financial data with people at scale.
[00:08:10.640 --> 00:08:16.400] Tens of thousands of people manually aggregating financial data at scale.
[00:08:16.400 --> 00:08:22.000] And our vision was: how can we do this better, faster, cheaper with technology?
[00:08:22.320 --> 00:08:31.680] And so as our ambition started to grow in terms of going after that big prize, it became clear that one, we were going to need a larger team.
[00:08:31.680 --> 00:08:35.040] We're going to need a lot more engineering, especially on the data side.
[00:08:35.040 --> 00:08:44.000] And we're going to need a pretty thought-out B2B go-to-market plan that is not going to fly with a million or two in the bank.
[00:08:44.000 --> 00:09:05.000] It's just, like, I think it's a little bit tricky to understand, but one of my investors said with salespeople and the most talented go-to-market folks, they're either going to be the newest people on your team because there's a lot of churn, or the highest paid four or five times more than the CEO at a successful startup.
[00:09:05.240 --> 00:09:20.280] And I was like, that really broke my frame of reference because it's like, oh, wow, they're actually going to make like way, way more money than me if they're closing deals the way that we actually need to go from zero to five to 10 to 20 to 100 million in ARR, right?
[00:09:20.280 --> 00:09:25.080] Like if you just reverse engineer like how much these people should be making, it's significant.
[00:09:25.080 --> 00:09:29.800] So you kind of need a little bit more capital if that's what you want to do.
[00:09:29.800 --> 00:09:31.560] It's not the only route.
[00:09:31.560 --> 00:09:36.440] Like capital is just a method to live in the future, as you would say.
[00:09:36.440 --> 00:09:38.280] And I totally agree with that.
[00:09:38.280 --> 00:09:43.880] The people that I wish I could one day afford or have or work with, I can work with them now.
[00:09:43.880 --> 00:09:45.640] And that's awesome to me.
[00:09:45.640 --> 00:09:46.520] It's a big deal.
[00:09:46.680 --> 00:10:09.160] I like what you touched on with the, what you're investor set, because most founders, especially bootstrap founders, don't realize that, that a salesperson, a GTM person at a startup like yours, if they make, let's say a salesperson makes a million dollars in, it's obviously salary plus commission, they should be generating, I think that it's a loose 10 to one, I think, they should be generating 10 million in ARR for you.
[00:10:09.160 --> 00:10:13.640] So therefore, it's a really good deal for you, even though it sounds a million.
[00:10:13.640 --> 00:10:14.760] What are you insane?
[00:10:14.760 --> 00:10:15.800] We can't afford that.
[00:10:15.800 --> 00:10:18.200] And it's like, that's, I think, what you're touching on, right?
[00:10:18.600 --> 00:10:22.280] Yeah, most folks would be like, oh, I'll never pay someone that much.
[00:10:22.280 --> 00:10:25.480] But then if you say, hey, you know, do you want 10 million in ARR?
[00:10:25.480 --> 00:10:26.440] You're like, of course.
[00:10:26.760 --> 00:10:27.720] I'd pay a million for that.
[00:10:27.880 --> 00:10:28.360] Nobody's going to be a bad person.
[00:10:28.680 --> 00:10:29.080] Exactly.
[00:10:29.080 --> 00:10:30.600] Yeah, yeah, exactly.
[00:10:30.600 --> 00:10:37.400] And so that has taken me a little bit of time to come to terms with a little bit.
[00:10:37.400 --> 00:10:45.360] And once you come to terms with it, then you can really actually build the right team and grow and make the right capital allocation decisions.
[00:10:45.360 --> 00:10:49.040] And sometimes it's not always the cheap, scrappy way.
[00:10:44.920 --> 00:10:50.720] You can still be frugal in other ways.
[00:10:51.280 --> 00:10:54.800] And like I'm recording this from my very cheap office.
[00:10:56.720 --> 00:10:57.840] Yeah, totally.
[00:10:57.840 --> 00:10:59.520] Well, and that's the thing, right?
[00:10:59.520 --> 00:11:03.760] It's like, could you bootstrap or mostly bootstrap this idea?
[00:11:03.760 --> 00:11:06.560] Maybe you would just have to approach it really differently, right?
[00:11:06.560 --> 00:11:12.720] And you would have to grow it slower and you could still maybe build a smaller business that's super profitable.
[00:11:12.720 --> 00:11:19.520] Maybe, you know, I don't know all the intricacies of it with AI and the cost and stuff, but there's usually multiple ways to build these businesses.
[00:11:19.520 --> 00:11:25.280] Super bootstrapped, mostly bootstrapped, and then raising a bit of money and then raising a shit load of money, which you're teetering.
[00:11:25.280 --> 00:11:27.840] To me, you're teetering right on that shit load, Mark.
[00:11:27.840 --> 00:11:37.760] But if you want to go after something that is going to be, that is really crowded, where it is winner take most, and where it's a land grab, that's what it feels like to me.
[00:11:37.760 --> 00:11:40.000] Is that what is happening in your mind?
[00:11:40.000 --> 00:11:48.240] Across just the three players, and this is not including Bloomberg, because Bloomberg is privately held, so it's hard to say what they're doing.
[00:11:48.480 --> 00:11:51.520] Most people think they're doing over 10 billion in ARR.
[00:11:51.520 --> 00:12:02.640] But just the three major public companies in terms of what we're doing in the segments that we're competing, 13 billion in ARR across that kind of oligobly, right?
[00:12:02.640 --> 00:12:06.880] And so it's worth going after this prize in my mind.
[00:12:06.880 --> 00:12:11.440] And I think the more that I've built, the more that this has remained true.
[00:12:11.440 --> 00:12:21.600] Is when we were working on something with a smaller goal and really just focused on that 1 million ARR, which, by the way, is a great goal for everyone who's starting the business.
[00:12:21.600 --> 00:12:35.320] It's not like it was, I was spending less time thinking about this, losing less sleep than I am now about what I want to do with the business or the amount of work required of the weekends of the evenings.
[00:12:29.840 --> 00:12:37.240] I'm all in regardless.
[00:12:37.560 --> 00:12:40.040] So let's go for something really big, right?
[00:12:40.040 --> 00:12:43.080] Like, especially if I'm going to take on investor capital.
[00:12:43.080 --> 00:12:46.440] I mean, I'm running an investor financial data business.
[00:12:46.440 --> 00:12:49.080] I came from this as an investor first.
[00:12:49.080 --> 00:12:58.360] So I take taking someone's capital seriously because I was on the other side of that transaction for 10 years prior.
[00:12:58.360 --> 00:13:05.320] So yeah, I mean, I've been an investor in public markets since the day I turned 18, I could open up my non-registered account.
[00:13:05.480 --> 00:13:09.480] So this has been something that I've thought about for a long, long time.
[00:13:09.800 --> 00:13:13.400] Do you feel like taking this much money?
[00:13:13.400 --> 00:13:16.920] Obviously, it implies that you have to get a lot bigger.
[00:13:16.920 --> 00:13:23.240] Like I'm assuming you want nine figures, meaning 100 million plus of ARR and maybe 10 figures.
[00:13:23.240 --> 00:13:24.680] You know, you're talking 13 billion of ARR.
[00:13:24.680 --> 00:13:25.640] Like you want a check of that.
[00:13:25.640 --> 00:13:28.200] I mean, I don't think it hurt your feelings to get to a billion ARR.
[00:13:28.200 --> 00:13:31.880] So obviously it means your goals, your aspirations, they're just bigger.
[00:13:31.880 --> 00:13:32.920] They have to be.
[00:13:32.920 --> 00:13:39.560] Do you feel like simultaneously that increases your chance of failure?
[00:13:39.880 --> 00:13:42.920] Yes, it does, without a doubt.
[00:13:42.920 --> 00:13:52.440] And I think that this is the one thing that me and my co-founders hummed and hawed on the most as I sat them down because I deal with all the fundraising and talking with investors as the CEO.
[00:13:52.440 --> 00:14:00.120] And I told them, guys, this changes our floor of success has to be so much higher.
[00:14:00.120 --> 00:14:08.920] Our ceiling can be a lot higher, but the floor is now on, you know, level 12 in the elevator, and we're only on level three right now.
[00:14:08.920 --> 00:14:14.440] So we have to go a lot, lot higher for this to be a success now, if we go down this route.
[00:14:14.440 --> 00:14:16.720] So we had to come to terms with that.
[00:14:16.720 --> 00:14:18.320] But like I said, we're still hungry.
[00:14:18.320 --> 00:14:19.600] We still wanted to work for it.
[00:14:19.600 --> 00:14:22.880] We're like, we're probably going to get there anyways, right?
[00:14:22.880 --> 00:14:29.200] It's just going to take us longer if we have to scrap this all together with a million in the bank versus 10.
[00:14:29.200 --> 00:14:30.160] Yeah, that makes sense.
[00:14:30.160 --> 00:17:41.360] Something I'm really happy with is that when Enar and I sat down to figure out the tiny seed investment terms, and this was seven years ago, this 2018, 19, we were just trying to figure out, because there's all these terms, there was indie.bc had kind of this thing where you could pay back and buy back equity and it was like phantom equity but it was like maybe that's interesting but also it's like a little complicated and then other competitors came on the scene with similar things but they like had accidentally or intentionally exploding terms where like if you raised and you didn't pay it back like suddenly you owe they own three times more of your company than they originally like just bizarre stuff right we really wanted we're like equity is equity equity has existed for like a thousand years 800 you know like a very long time and so let's keep it pretty simple we do have a side letter of course because there's salary and participation caps and stuff you couldn't just pay yourself a million dollar salary and not pay tiny seed anything blah blah blah but one of the things we wanted to be really careful about was that we want tiny seed companies after they take our money to have optionality if you never want to raise money again and you want to basically be mostly bootstrapped great if you want to raise a bit of money if you want to raise a lot of money we didn't want that to negatively impact your ability and you are one of several founders who have raised a lot of money seven or eight figures and had at least from my perspective i just signed the docs i don't actually you know lawyer tells me to read them doesn't seem like our terms or any being affiliated with tiny seed had any negative impact on your raise is that true no and i think that you guys have been easy to work with because what i'll say is the newest investor in always wants to be the biggest swing and you know what so they basically that they as the lead will take those terms and previous investors of course there's dilution there's no way around this kind of inevitable feat you get your markup there's a little bit of dilution that's the world of of raising additional capital same with my holdings too right like we're all losing a little bit uh on new money in but the the terms that are coming in with the largest investor is like kind of like they want it their way and you guys have been very easy to work with on like hey they want this way but you're still gonna get this you're still gonna get that you're still a major investor you don't lose any of this this or that and i think that that's a good way to do it right because you're giving us optionality to keep growing if we want to if we didn't want to take any money like that's also fine too right so i think that's the right way to do it because businesses change over time a startup doesn't like when we first met my business was a lot different it was two names ago rub ten dollars a month if i remember it was it was crazy night and day right so you have to be you have to be flexible you have to be pivoting and and you you need investors that are open to that as well because really good investors know that like you're betting on that i'm gonna figure it out and that's something i tell you what, early on with tiny Seed, I did a microconf talk and i remember saying something like, if we start funding, I don't even think tiny Seed existed, but i was like, if i was going to invest in bootstrappers, it would be one round and then they'd never raise again.
[00:17:41.360 --> 00:17:42.480] They'd never have to raise again.
[00:17:42.480 --> 00:17:46.480] And I remember coming off stage and ainar was like, don't say that because you don't know.
[00:17:46.480 --> 00:17:47.600] And it was a real good wake-up.
[00:17:47.680 --> 00:17:49.040] Like, you don't know if they're going to want to raise.
[00:17:49.040 --> 00:17:53.440] Some businesses, we might invest $150,000, $200,000.
[00:17:53.440 --> 00:17:56.320] And it was a very small amount of money in the scheme of things.
[00:17:56.320 --> 00:18:01.600] And if they catch lightning by the tail, they might want to raise three, five, $10, $20 million.
[00:18:01.600 --> 00:18:06.160] And it's like, it's a small subset of Tiny Seed companies, but there are a decent chunk of folks who've done it.
[00:18:06.160 --> 00:18:09.680] And so, A, I'm glad that our terms, because that was the intent was to allow that.
[00:18:09.920 --> 00:18:15.520] Optionality, that was a big thing with Tiny Seed: hey, you can sell for 10, 20 million, but you can also go after the big one.
[00:18:15.520 --> 00:18:18.160] But it is a reminder, maybe to a listener.
[00:18:18.160 --> 00:18:21.120] There are a lot of listeners who are just diehard, bootstrap, bootstrap, bootstrap.
[00:18:21.120 --> 00:18:22.160] I just want a lifestyle.
[00:18:22.160 --> 00:18:23.760] That's what Drip originally was.
[00:18:23.760 --> 00:18:27.440] I was trying to build a little lifestyle business that was going to generate a bunch of profit.
[00:18:27.440 --> 00:18:28.480] And then guess what?
[00:18:28.480 --> 00:18:32.880] I found a bigger opportunity and I just took it in a different direction, right?
[00:18:32.880 --> 00:18:39.440] And like that changed my life because I was open to that possibility of changing my mind.
[00:18:39.440 --> 00:18:42.640] Did you think when you bootstrapped Stratosphere?
[00:18:42.640 --> 00:18:44.560] I had to say, since it's two names ago, I almost said finish.
[00:18:44.720 --> 00:18:51.600] When you bootstrapped Stratosphere in your mind, were you early on like, will never take money?
[00:18:51.600 --> 00:18:54.160] I would take money on the right terms.
[00:18:54.160 --> 00:18:55.440] Definitely want to raise money.
[00:18:55.440 --> 00:18:58.320] You know, where were you on that bootstrapping continuum?
[00:18:58.320 --> 00:19:05.520] I mean, I think I'd be giving myself a lot of credit if I think I had any sort of clue what I was going to do at that point.
[00:19:05.520 --> 00:19:15.280] But generally, I wanted to build something that would, me and my co-founders could pay ourselves a little bit of money, maybe hire a couple people.
[00:19:15.280 --> 00:19:24.640] You know, my dream was to have this kind of bootstrapped, can do whatever I want, cash flow business, so I could live in Bali and like surf every day.
[00:19:24.640 --> 00:19:27.200] That was like kind of my goal.
[00:19:27.200 --> 00:19:31.480] But, you know, things change, the business changes, your personal life changes.
[00:19:32.680 --> 00:19:38.920] You just want different things, especially, you know, when we started this business, I was, I'm 29 now, so I was 26.
[00:19:38.920 --> 00:19:44.440] Like, I didn't know what I wanted to do beyond what I was going to eat for lunch that day.
[00:19:44.440 --> 00:19:49.640] So I don't think I had a grand vision other than I knew I wanted to be an entrepreneur.
[00:19:49.640 --> 00:19:50.760] That's pretty much it.
[00:19:50.760 --> 00:19:55.720] And I knew I wanted to help solve the problems that I saw in finance.
[00:19:56.040 --> 00:19:59.320] And you are open to being open to what comes.
[00:19:59.320 --> 00:20:00.680] And it's like, hey, maybe we'll go bigger.
[00:20:00.680 --> 00:20:01.720] Maybe we'll rebrand.
[00:20:01.720 --> 00:20:03.960] Maybe we'll raise some funding.
[00:20:03.960 --> 00:20:15.080] I'm curious, as I mean, you're a 29-year-old CEO of a company that now has 34 people on your team and you have six more starting shortly.
[00:20:15.080 --> 00:20:18.040] You're about to be the CEO of a 40-person company.
[00:20:18.040 --> 00:20:20.520] There's got to be, I mean, that's bigger than any company I've ever run.
[00:20:20.600 --> 00:20:21.800] Drip was 10 when I sold it.
[00:20:21.800 --> 00:20:27.960] I guess I was running a team within, you know, the acquisition of or the acquirer of maybe 21 at the end.
[00:20:27.960 --> 00:20:31.080] But even Tiny Seed Microconf all combined today is still like 10 people, right?
[00:20:31.080 --> 00:20:33.880] So 40 is significantly more than I would even enjoy.
[00:20:33.880 --> 00:20:35.960] I just don't enjoy managing a lot of people.
[00:20:35.960 --> 00:20:42.280] There has to have been some maybe learnings, growing pains, just all of that stuff.
[00:20:42.280 --> 00:20:47.000] Again, as a, like you're obviously highly competent, very intelligent, but you are, you're a young dude.
[00:20:47.000 --> 00:20:49.320] Like I don't think you've managed 40 people before.
[00:20:49.320 --> 00:20:52.280] So what is this feeling like for you these days?
[00:20:52.280 --> 00:20:59.160] When we hit 25 people at the end of last year, I had a major wake-up call.
[00:20:59.160 --> 00:21:03.520] Like it like slapped me in the face once we hit 25.
[00:21:03.520 --> 00:21:09.960] And I hadn't built the right infrastructure for a company to exist at 25 people.
[00:21:10.280 --> 00:21:16.480] We were just flying by the seat of our chair like it was just me and my three co-founders.
[00:21:16.480 --> 00:21:18.720] And then I woke up and there's 25 people.
[00:21:18.720 --> 00:21:24.560] And it's like, whoa, okay, we gotta like see, I have to actually become a CEO.
[00:21:24.560 --> 00:21:37.200] And so I started trying to learn and trying to focus and just like take the realization that this is not just me and my co-founders hacking around away trying to make money on the internet anymore.
[00:21:37.200 --> 00:21:42.800] This is like people are making real money, real salaries, real lives working for us.
[00:21:42.800 --> 00:21:48.720] And we need to build a really sustainable, scalable company as we can go.
[00:21:48.720 --> 00:21:54.000] And so that's the wall, I would say, is 25.
[00:21:54.320 --> 00:22:01.280] And I was like, okay, I say I've been the CEO of this company for two years, but I haven't been.
[00:22:01.280 --> 00:22:02.640] Now I need to be.
[00:22:02.640 --> 00:22:06.480] And I think I've gotten a lot better, honestly.
[00:22:06.480 --> 00:22:13.280] What were some of the things, what were some examples of things that maybe weren't working that you had to then add structure in order to fix?
[00:22:13.280 --> 00:22:17.760] A book I'd recommend to everyone is called The Great CEO Within.
[00:22:17.760 --> 00:22:20.800] It's the tactical guide to company building.
[00:22:20.800 --> 00:22:23.600] It's short, it's like 200 pages.
[00:22:23.600 --> 00:22:26.720] It's just step-by-step advice.
[00:22:26.720 --> 00:22:35.840] There's lots of amazing CEOs who have chimed in in certain sections, whether it's, you know, Brian Armstrong of Coinbase or the guy who did Clearbit.
[00:22:35.840 --> 00:22:39.920] Like a lot of people came together to build this book.
[00:22:39.920 --> 00:22:44.640] And it's a book that every Sequoia founder is given when they invest in them.
[00:22:44.640 --> 00:22:46.400] And so I read that book.
[00:22:46.400 --> 00:22:57.200] That really helped me frame around this idea of if I have to do it twice, it needs to be an actual process or written down somewhere.
[00:22:57.200 --> 00:23:04.200] A company, Wikipedia, it can be as simple as just utilizing a Google Drive better and file systems.
[00:22:59.760 --> 00:23:05.560] Just little things like that.
[00:23:05.800 --> 00:23:08.600] If I have to do it twice, it needs to be a system.
[00:23:08.600 --> 00:23:16.840] Because there's a lot of stuff you're going to start having to repeat all the time, whether it's hiring, whether it's operational stuff, whether it's sales.
[00:23:16.840 --> 00:23:21.800] I was wasting so much time starting from scratch every time I was doing something.
[00:23:22.120 --> 00:23:24.840] So that really, really helped.
[00:23:24.840 --> 00:23:33.800] And then, secondly, around how to properly encourage my employees to succeed and tell them that they're doing a good freaking job.
[00:23:33.800 --> 00:23:37.080] Because a lot of them are doing an amazing job.
[00:23:37.080 --> 00:23:43.240] And I think that before I was just, I assumed that they knew that I thought they were doing a great job.
[00:23:43.240 --> 00:23:48.440] It is amazing what happens when you tell people just some simple recognition of how good of a job they're doing.
[00:23:48.440 --> 00:23:55.800] Because there's some people who are killing it at our company, like crushing it, working so hard and they're so happy here.
[00:23:55.800 --> 00:24:01.000] But, you know, it is amazing what some recognition or some recognition on a team call could do.
[00:24:01.000 --> 00:24:02.200] Some structure.
[00:24:02.200 --> 00:24:06.200] Every Friday, every single person in the company talks at our meeting now.
[00:24:06.200 --> 00:24:11.160] Before, it would just be me like telling them what we're going to do next week.
[00:24:11.160 --> 00:24:16.920] Now it's every single person telling me what they're going to do and asking me how I can help them.
[00:24:16.920 --> 00:24:21.480] So that has massively changed the way that the business is operated, I would say.
[00:24:21.480 --> 00:24:24.200] But it's not hard, Rob.
[00:24:24.200 --> 00:24:27.800] We're doing stuff that's way harder than these things that I've had to figure out.
[00:24:27.800 --> 00:24:30.680] This is easy, easy stuff, but it goes a long way.
[00:24:30.680 --> 00:24:32.520] Yeah, that's a great book recommendation, by the way.
[00:24:32.520 --> 00:24:38.200] I don't know that I've actually read it, but I have heard, I've seen it, and I know folks recommend it.
[00:24:38.200 --> 00:24:39.720] No, no fluff in that book.
[00:24:39.720 --> 00:24:40.600] It's very straightforward.
[00:24:40.760 --> 00:24:41.240] Yeah, it's tight.
[00:24:41.480 --> 00:24:42.200] Yeah, it's real tight.
[00:24:42.200 --> 00:24:43.560] Yeah, 200 pages.
[00:24:43.560 --> 00:24:48.000] Do you enjoy being the CEO of a 40-person company specifically?
[00:24:48.000 --> 00:24:49.280] Sometimes no.
[00:24:49.600 --> 00:24:53.200] Yeah, yeah, I was going to say, because there's got to be some hard days.
[00:24:53.200 --> 00:24:55.520] There's got to be some complicated days with it.
[00:24:55.520 --> 00:25:07.440] There's some complicated days, but there are some days that are so freaking good as well that, you know, the highs and the lows are certainly there.
[00:25:07.440 --> 00:25:14.080] And I try to, if I don't manage myself with the highs and the lows, my employees know it and feel it.
[00:25:14.080 --> 00:25:16.800] So I have to be pretty even keel.
[00:25:16.800 --> 00:25:20.560] So there are certainly days that are not as fun.
[00:25:20.560 --> 00:25:23.280] There are certainly days that are a ton of fun.
[00:25:23.280 --> 00:25:27.680] But at the end of the day, I don't want to do anything else differently right now.
[00:25:27.680 --> 00:25:37.200] So it would be a problem for me when there was hard days if I was just like, oh, there's something that I really want to do that's not this.
[00:25:37.520 --> 00:25:39.040] But I don't have that.
[00:25:39.040 --> 00:25:41.120] I want to see this thing work really well.
[00:25:41.120 --> 00:25:43.280] So that's, that kind of keeps me going.
[00:25:43.280 --> 00:25:43.760] Yeah.
[00:25:43.760 --> 00:25:51.040] I think growth also always used to keep, like, I know your growth curve, obviously, because I'm an investor in AC and it's like you're growing very fast.
[00:25:51.040 --> 00:25:56.960] And for me, MRR, ARR going up into the right, it made a lot of ills go away.
[00:25:56.960 --> 00:25:58.480] For me, I was just like, you know what?
[00:25:58.480 --> 00:25:59.120] It's working.
[00:25:59.120 --> 00:25:59.840] This is hard.
[00:25:59.840 --> 00:26:01.120] It's not supposed to be easy.
[00:26:01.120 --> 00:26:04.640] But if you're doing all this grind and it's flat, it's terrible.
[00:26:04.640 --> 00:26:08.000] Like it's the worst because you're just like, none of this is worthwhile.
[00:26:08.000 --> 00:26:08.960] I'm wasting my time.
[00:26:08.960 --> 00:26:10.560] I'm going, why am I doing this?
[00:26:10.560 --> 00:26:14.560] You know, so it growth cures most ills, I think.
[00:26:14.560 --> 00:26:17.200] ARR growth solves a lot of problems.
[00:26:17.200 --> 00:26:17.600] Yeah.
[00:26:17.840 --> 00:26:20.720] Including my ability to sleep well at night.
[00:26:20.720 --> 00:26:21.840] Exactly.
[00:26:22.160 --> 00:26:22.560] All right.
[00:26:22.560 --> 00:26:29.040] So I want to ask you, we were talking offline and you threw some bullets into a dock for me to help guide this conversation.
[00:26:29.040 --> 00:26:41.320] And one of the things that you said was something we could talk about was why I shut down a B2B product that went from zero to one and a half million ARR in 12 months and then I shut it down.
[00:26:41.320 --> 00:26:44.520] Talk us through what was that product and why.
[00:26:44.840 --> 00:27:00.840] We started licensing our AI co-pilot product, which is basically you could converse with all the financial data, get it to build you graphs, get you to summarize transcripts, slide decks, everything was pre-loaded into there.
[00:27:00.840 --> 00:27:05.800] We exposed that product while we were trying to build a ton of other products.
[00:27:05.800 --> 00:27:08.280] So it was just like a lot was going on.
[00:27:08.280 --> 00:27:11.720] It was a bit of a distraction, but the money was flowing in.
[00:27:11.720 --> 00:27:18.440] It went from zero to a million and a half of ARR, growing, you know, 20% a month consistently, even when I shut it down.
[00:27:18.440 --> 00:27:23.320] It was probably, it would probably be like two and a half, three today, maybe more.
[00:27:23.320 --> 00:27:26.600] The problem with it was we were signing big customers.
[00:27:26.600 --> 00:27:29.400] One of them was $250,000 a year.
[00:27:29.400 --> 00:27:31.480] Several were in the hundreds of thousands of dollars.
[00:27:31.720 --> 00:27:34.040] Some on the just tens of thousands of dollars.
[00:27:34.040 --> 00:27:39.880] And a lot of customers were coming offline pretty quick and telling us quickly that they were not going to renew.
[00:27:39.880 --> 00:27:48.680] And the reason for that was we solved a key problem at one point that ChatGPT couldn't handle any of these queries very well.
[00:27:48.680 --> 00:27:50.840] That problem went away.
[00:27:50.840 --> 00:27:56.280] And the foundational model started to kick our asses at our own game.
[00:27:56.280 --> 00:27:58.280] And so we started to see the writing on the wall.
[00:27:58.280 --> 00:28:01.240] We're like, okay, this is not actually what we're good at.
[00:28:01.240 --> 00:28:05.480] Us doing rag for them and solving this quick problem for these customers.
[00:28:05.480 --> 00:28:10.120] It's probably a quick solve because they want AI on their platform yesterday.
[00:28:10.440 --> 00:28:13.960] The CEO's begging the product team, why is there an AI not on our product?
[00:28:13.960 --> 00:28:23.440] We were a quick solution, a quick fix for them, but it wasn't the right solution for them because then they would say to us, How do I connect my customer service bot to this as well?
[00:28:23.440 --> 00:28:28.640] Or how do I connect my customer clients are asking how they do their own account openings?
[00:28:28.640 --> 00:28:32.800] And it's getting confusing because this was a very narrow product.
[00:28:32.800 --> 00:28:34.960] And we said, Okay, sorry, I can't help you with that.
[00:28:34.960 --> 00:28:38.640] Like, you're gonna have to build it from scratch with our data.
[00:28:38.640 --> 00:28:41.200] And then they started doing that.
[00:28:41.200 --> 00:28:43.360] And that had product market fit.
[00:28:43.360 --> 00:28:56.400] And so we shut down this out-of-the-box solution that so many people loved right away because the actual slower, longer implementation were customers that I think will be with us forever.
[00:28:56.400 --> 00:29:06.640] And that is a materially different type of anxiety when you see 30 customers sign up and 15 of them turn before three months in.
[00:29:07.600 --> 00:29:08.320] That's brutal.
[00:29:08.560 --> 00:29:10.800] Terrible, terrible.
[00:29:10.800 --> 00:29:12.640] So we just said, screw it.
[00:29:12.640 --> 00:29:15.520] We got, you know, we're going to shut it down with the financing.
[00:29:15.520 --> 00:29:17.280] And that's what it is.
[00:29:17.280 --> 00:29:18.640] That is what it is.
[00:29:18.640 --> 00:29:19.040] Wow.
[00:29:19.040 --> 00:29:19.360] Yeah.
[00:29:19.360 --> 00:29:20.640] These are hard decisions.
[00:29:20.640 --> 00:29:24.160] Did you feel hard decisions with incomplete information?
[00:29:24.160 --> 00:29:26.160] Did you have much doubt when you did that?
[00:29:26.160 --> 00:29:31.280] Because that's a one-way door-ish type of thing that's really hard to undo.
[00:29:31.280 --> 00:29:35.040] Were you kind of like convicted and you were like, no, this is the right way?
[00:29:35.040 --> 00:29:38.960] Or were you like, oh, he and Han trying it on for weeks and months?
[00:29:38.960 --> 00:29:51.120] I knew it was the right decision when I was seeing how much it was causing issues with our development team for building the long-term product that we actually envisioned.
[00:29:51.120 --> 00:29:58.560] Because there was a lot of bugs, it was a lot of customer service requests that we just were not getting for our core foundational product.
[00:29:58.560 --> 00:30:00.680] People were way more happy there.
[00:30:01.240 --> 00:30:12.680] So, a combination of churn and distraction from the dev team was enough for me to go, look, this is not what's going to make this business a success.
[00:30:12.680 --> 00:30:19.800] So, reverse engineering that, yeah, it's tough to say no to that much revenue when you're at our size, but I think it was the right call.
[00:30:19.800 --> 00:30:21.960] It's still really early to say, right?
[00:30:21.960 --> 00:30:27.400] Like, it sucks when customers ask us today if they can come buy it.
[00:30:27.400 --> 00:30:30.440] And I'm like, no, you can't.
[00:30:30.440 --> 00:30:31.800] I gotta say, no.
[00:30:32.120 --> 00:30:34.680] Turning down revenue is the worst.
[00:30:34.680 --> 00:30:39.960] Yeah, the worst is saying yes to revenue and having it churn, but the second worst is turning down revenue.
[00:30:40.360 --> 00:30:41.720] I want to switch topics a little bit.
[00:30:41.720 --> 00:30:46.600] I just have maybe two more questions for you, but one is about you have three co-founders.
[00:30:46.600 --> 00:30:48.120] So, there's four of you total.
[00:30:48.120 --> 00:30:58.360] And I'm curious, we talked about this last time we recorded, so I won't go too far into it, but I'm curious now that you're here where you are with a 40-person team and you've raised all this money.
[00:30:58.360 --> 00:31:06.760] What's maybe the biggest positive to having that many co-founders and the biggest negative that you've seen?
[00:31:06.760 --> 00:31:18.040] The biggest positive is that there are four of us across the different parts of our business that have an amazing leader on day one.
[00:31:18.040 --> 00:31:19.480] That's the biggest positive.
[00:31:19.480 --> 00:31:27.000] So, me as a CEO, my chief product officer, one of my co-founders, my CTO, one of my co-founders.
[00:31:27.000 --> 00:31:31.480] So, they run tech and product and they are outstanding at what they do.
[00:31:31.480 --> 00:31:36.680] And then, my CEO, Adrian, runs all of our data operations and just operations in general.
[00:31:36.680 --> 00:31:40.520] And he is, he's the dream hire, right?
[00:31:40.520 --> 00:31:46.400] So, I had kind of the dream hire on day one from day one, building the business.
[00:31:44.680 --> 00:31:50.880] And to me, that is super, super valuable, without a doubt.
[00:31:51.200 --> 00:31:52.720] Plus, I love these guys.
[00:31:52.720 --> 00:31:55.680] So it's nice to, it's great hanging out with them every day.
[00:31:55.840 --> 00:31:57.520] So it's just a good team.
[00:31:57.520 --> 00:31:58.640] We get along great.
[00:31:58.640 --> 00:32:13.040] The biggest downside, I guess, would be I could see the potential for clashing when it comes to decision making, hiring, product decisions, long-term vision.
[00:32:13.040 --> 00:32:24.880] But I think if you were to ask my co-founders, they would say that I've earned their trust to unequivocally make almost all of those decisions and ask them if it's okay.
[00:32:24.880 --> 00:32:26.560] And they give me the green light.
[00:32:26.560 --> 00:32:32.720] But we don't pose strategic questions and say, what do we think?
[00:32:32.720 --> 00:32:36.240] I pose the strategic questions, say, this is what I'm doing.
[00:32:36.240 --> 00:32:37.920] This is where we're going to go.
[00:32:37.920 --> 00:32:41.440] Does anyone have any major issues with this?
[00:32:41.440 --> 00:32:44.960] If so, then speak up, then we'll reroute.
[00:32:44.960 --> 00:32:51.840] But if not, and you, you know, I've given, I've gained your trust and your leash to be able to make these decisions, then let's go.
[00:32:51.840 --> 00:32:54.400] So everyone focuses on what they're good at.
[00:32:54.400 --> 00:32:59.360] And so I think the pros majorly outweigh any cons, in my view.
[00:32:59.360 --> 00:33:03.600] Yeah, well, it seems to be working for you, too, you know, with the growth and the success.
[00:33:03.600 --> 00:33:06.880] Obviously, raising funding is a tool and it's a milestone.
[00:33:06.880 --> 00:33:08.320] It's not the finish line.
[00:33:08.560 --> 00:33:10.960] You and I both know this, so I don't want to, that's not worth saying.
[00:33:11.120 --> 00:33:13.680] The finish line got a lot further away when you did this money.
[00:33:13.920 --> 00:33:15.440] We just extended the finish line.
[00:33:15.440 --> 00:33:19.360] So, last question for me today is regarding Tiny Seed.
[00:33:19.360 --> 00:33:26.800] When this episode goes live, Tiny Seed applications will open like a week or two later, right, for our next batch, our 16th batch or something like that, September 1.
[00:33:27.120 --> 00:33:30.760] And I'm curious, I don't know quite how to ask this question.
[00:33:31.080 --> 00:33:37.880] Maybe it's like, what are the top three or four things you and your team, you know, your founding team got out of Tiny Seed?
[00:33:38.200 --> 00:33:44.760] Or maybe it's if someone's on the fence, they're listening to this, what would be the benefits for them joining?
[00:33:44.760 --> 00:33:48.600] And maybe you could even say, well, if you're, if you want to do X, don't join Tiny Seed.
[00:33:48.600 --> 00:33:49.160] You know what I mean?
[00:33:49.160 --> 00:33:50.440] Like the pros and cons.
[00:33:50.440 --> 00:33:57.880] We don't have to go full pros and cons, but it's kind of like, what did you get out of Tiny Seed that like would lead someone to apply and want to do it?
[00:33:57.880 --> 00:33:59.240] Yeah, there's three things.
[00:33:59.240 --> 00:34:05.240] So if you're comfortable with saying, I think it was 200K that we raised from you guys.
[00:34:05.560 --> 00:34:11.960] And so at that time, nowadays, I'm like, that's like, what do I do with that, right?
[00:34:11.960 --> 00:34:12.360] Yeah.
[00:34:12.360 --> 00:34:17.560] But at that time, when you have 10,000 in the bank, it's everything, right?
[00:34:17.560 --> 00:34:19.800] Like, so it's that frame of reference.
[00:34:19.800 --> 00:34:26.920] So that did materially actually help us, I'm not going to lie, especially with our vision, which was, it was in a sweet spot for us at the time.
[00:34:26.920 --> 00:34:31.160] Of course, you know, the vision changed, the ambition changes, but at the time, it was the right amount.
[00:34:31.160 --> 00:34:42.200] The second thing that I think was super helpful was just, yeah, just early on, we were using you and ANR a lot around like pricing, which customers are working.
[00:34:42.200 --> 00:34:43.960] What do you think about this strategic?
[00:34:43.960 --> 00:34:46.600] Is freemium versus non?
[00:34:46.760 --> 00:34:59.960] Like some of the basic questions that you talk about on this podcast a lot are super helpful for anyone listening, but it's even more helpful if we can talk specifically about my business, right?
[00:35:00.280 --> 00:35:07.800] Like I can learn from Joe's other business, but when we're talking specifically about my business, it's obviously a lot more tangible.
[00:35:08.040 --> 00:35:09.640] So that would be the second thing.
[00:35:09.640 --> 00:35:21.760] And then the third thing is, I don't actively participate in the Slack community, but if I have a question, I know it's going to get answered really well by like 30 people in the matter of hours.
[00:35:22.080 --> 00:35:28.880] So I would say I am more of a receiver of information more than a giver on there.
[00:35:28.880 --> 00:35:31.440] So it's probably more of a one-way street for me.
[00:35:31.440 --> 00:35:36.240] It should probably be a little bit more reciprocal, but that's just kind of what I get out of it.
[00:35:36.400 --> 00:35:38.320] It's amazing for me, to be honest.
[00:35:38.320 --> 00:35:38.800] I'm glad.
[00:35:38.800 --> 00:35:46.160] And that, you know, it's funny with the first batch or two, the Slack group was obviously tiny because there were 10 founders and then 20 founders or whatever.
[00:35:46.160 --> 00:35:49.440] And Anar and I used to have to answer a lot of the questions.
[00:35:49.440 --> 00:35:51.280] And it was just like, well, no one else knows.
[00:35:51.280 --> 00:35:52.880] And so I am going to give my best answer.
[00:35:52.880 --> 00:35:54.400] And there'd be other stuff trickling.
[00:35:54.400 --> 00:36:01.280] Now, by the time I, we have an advice needed channel for those who don't know, you know, by the time I get to any question, there's already five responses.
[00:36:01.280 --> 00:36:04.000] And I tend to look through and be like, ooh, that's smarter than what I would have said.
[00:36:04.000 --> 00:36:06.000] Oh, he's done it more recently than I have.
[00:36:06.000 --> 00:36:07.120] Oh, she has better insight.
[00:36:07.440 --> 00:36:15.360] And it's usually like what they said, you know, with an arrow up, or maybe I have a little bit to add, but it's like, I'm no longer the expert.
[00:36:15.440 --> 00:36:18.320] I don't have to be the expert me, Rob Walling doesn't have to be the expert on everything.
[00:36:18.320 --> 00:36:19.520] And I shouldn't have to be.
[00:36:19.520 --> 00:36:23.840] Like, because there are 300 something, there's 204 companies and I think it's 310 founders.
[00:36:23.840 --> 00:36:28.240] I don't know the exact number, but very knowledgeable people like yourself that are really knee deep.
[00:36:28.240 --> 00:36:38.320] You know, if someone's like, hey, I want to know how ML stuff and data and financial whatever, like me, I don't really know, but like you or your co-founder Kevin or one of your other founders is going to really know it.
[00:36:38.880 --> 00:36:44.400] Even stuff like this, we're a Toronto, Canada-based startup and there's a Canada channel.
[00:36:44.400 --> 00:36:59.640] And we have specific questions around our tax situation or our HR situation that you know we're a little underserved because most of those questions on the internet or in these types of Slack communities are specifically about U.S.
[00:36:59.600 --> 00:37:01.080] tax or U.S.
[00:36:59.840 --> 00:37:01.720] regulations.
[00:37:02.040 --> 00:37:08.200] So, for us to have our little corner where we know we're dealing with the same context is pretty helpful.
[00:37:08.200 --> 00:37:09.080] That's great.
[00:37:09.080 --> 00:37:11.800] Well, Braden, thanks so much for coming back on the show, man.
[00:37:11.800 --> 00:37:17.320] If folks want to keep up with you on the internet, of course, you're BradoCapital on X Twitter.
[00:37:17.320 --> 00:37:21.480] And if they want to see what you're building, it's at fiscal.ai.
[00:37:21.480 --> 00:37:22.760] Thanks again for joining me.
[00:37:22.760 --> 00:37:23.560] Thank you.
[00:37:23.560 --> 00:37:26.440] Thanks again to Braden for coming back on the show.
[00:37:26.440 --> 00:37:29.960] And thanks to you for listening this week and every week.
[00:37:29.960 --> 00:37:33.800] This is Rob Walling signing off from episode 787.

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

[00:00:00.160 --> 00:00:02.000] You're listening to Startups for the Rest of Us.
[00:00:02.000 --> 00:00:03.200] I'm Rob Walling.
[00:00:03.200 --> 00:00:06.480] In this episode, I have a conversation with Braden Dennis.
[00:00:06.480 --> 00:00:07.840] He's come back on the show.
[00:00:07.840 --> 00:00:16.560] He's the co-founder of FinChat, and they have recently rebranded to fiscal.ai after raising a $10 million Series A.
[00:00:16.880 --> 00:00:23.920] I don't cover a lot of venture raises on this podcast because we focus on bootstrapped and mostly bootstrapped companies.
[00:00:23.920 --> 00:00:38.720] But now and again, in our ecosystem, we are seeing bootstrappers who catch lightning in a bottle and they realize that the opportunity that they've stumbled upon has much more potential than they originally thought.
[00:00:38.720 --> 00:00:46.240] And some of those folks decide to sell early, some folks continue to bootstrap, and others decide to go that venture route.
[00:00:46.240 --> 00:00:53.040] And today, Brayden and I discuss that decision about why he and his co-founders decided to shoot for the moon.
[00:00:53.040 --> 00:00:58.640] As you can tell by the title, we also talk about how they shut down a $1.5 million ARR product.
[00:00:58.640 --> 00:01:01.120] And we do a quick recap of what got them here.
[00:01:01.120 --> 00:01:07.120] You can hear more of that in his prior episode, which I mentioned during the interview.
[00:01:07.120 --> 00:01:13.040] Before we dive into that conversation, I want to let you know about our MicroConf local chapters.
[00:01:13.040 --> 00:01:16.160] Building a business can be isolating, but it doesn't have to be.
[00:01:16.160 --> 00:01:25.040] So inside MicroConf Connect, which is our online membership community, we are launching local chapters to help you meet each other in person.
[00:01:25.040 --> 00:01:38.080] Our first local chapters will be taking place in Barcelona, Toronto, Sydney, Austin, and London, giving you the chance to share challenges, exchange ideas, and build relationships with other founders in your area.
[00:01:38.080 --> 00:01:42.800] Alongside these local chapters, we're also opening up the MicroConf Ambassador Program.
[00:01:42.800 --> 00:01:47.520] If you want to help bring founders together in your city, you can apply to become an ambassador.
[00:01:47.520 --> 00:01:53.920] We'll provide everything you need: a comprehensive playbook, promotional support, and swag to make your events successful.
[00:01:53.920 --> 00:01:56.560] Because no event can be successful without swag, am I right?
[00:01:56.560 --> 00:02:07.720] If you're looking for accountability, collaboration, or just a good conversations over coffee, apply to join Microconf Connect and become a part of the community to learn more about local chapters and the ambassador program.
[00:02:07.720 --> 00:02:10.760] Head to microconfconnect.com.
[00:02:10.760 --> 00:02:16.040] And with that, let's dive into my enlightening conversation with Brayden Dennis.
[00:02:22.440 --> 00:02:24.840] Braden Dennis, welcome back to the show.
[00:02:24.840 --> 00:02:25.160] Mr.
[00:02:25.160 --> 00:02:27.080] Walling, it's always good to see you.
[00:02:27.400 --> 00:02:28.520] So good to have you, man.
[00:02:28.520 --> 00:02:31.960] So you were on episode 705 of this very show.
[00:02:31.960 --> 00:02:34.760] It was March 19th of last year.
[00:02:34.760 --> 00:02:37.160] So just over, what, about 15 months ago?
[00:02:37.160 --> 00:02:46.280] And we talked about how your SaaS app called Stratosphere, how you went from bootstrapped to taking money from Tiny Seed.
[00:02:46.280 --> 00:02:49.080] So we said mostly bootstrapped, to then going venture-backed.
[00:02:49.080 --> 00:02:53.640] And I believe you had raised pre-seed round, what was it, 2 million, 3 million?
[00:02:53.640 --> 00:02:54.600] It was 1.5.
[00:02:54.600 --> 00:02:55.480] 1.5.
[00:02:55.480 --> 00:02:56.120] Okay.
[00:02:56.440 --> 00:02:58.440] And we covered a bunch of topics.
[00:02:58.840 --> 00:03:07.800] You rebranded to FinChat and have more of an AI event where you could, you know, chat with what, public market data really is the thing that you have.
[00:03:07.880 --> 00:03:10.360] How you had launched a second product, and you and I talked through.
[00:03:10.360 --> 00:03:13.640] I was like, my advice is usually not to, and when is an exception, right?
[00:03:13.640 --> 00:03:15.240] We talked through in that episode.
[00:03:15.240 --> 00:03:18.440] And then you, I mean, I guess catch us up.
[00:03:18.440 --> 00:03:20.840] You raised that venture round.
[00:03:20.840 --> 00:03:23.080] And now you've just raised another.
[00:03:23.080 --> 00:03:27.960] You've raised a $10 million Series A, which is a shload of money for a bootstrapper.
[00:03:27.960 --> 00:03:29.880] And I still think of you, I mean, you guys are moving fast.
[00:03:29.880 --> 00:03:31.080] It's a big, ambitious space.
[00:03:31.080 --> 00:03:32.920] And you're now a venture-backed company.
[00:03:32.920 --> 00:03:38.840] But, like, when you and I first met, you were a podcaster with a little B2C, you know, personal finance app.
[00:03:38.840 --> 00:03:43.640] So, catch us up on the last year and a half.
[00:03:43.640 --> 00:03:47.360] Yeah, I mean, total funding to date is now 13 million U.S.
[00:03:44.840 --> 00:03:51.360] and it sounds insane to say because it's not so long ago.
[00:03:51.680 --> 00:03:55.280] I met you for the first time in Austin, Texas, after Tiny Seed.
[00:03:55.280 --> 00:04:03.280] And yeah, I was like, okay, we're just going to take this little bit of money, me and my co-founders, we're going to, you know, try to get this to a few million in ARR.
[00:04:03.280 --> 00:04:08.640] I mean, at that point, your only goal is like a million in ARR, a million in ARR, a million in ARR.
[00:04:08.960 --> 00:04:11.280] I will be happy when I hit one million.
[00:04:11.840 --> 00:04:12.960] You're going to be happy forever.
[00:04:12.960 --> 00:04:13.760] Forever.
[00:04:14.480 --> 00:04:15.280] Forever.
[00:04:15.280 --> 00:04:16.560] I'll be fully content.
[00:04:16.560 --> 00:04:18.560] There'll be nothing wrong with the world, right?
[00:04:18.560 --> 00:04:20.400] And so, you know, that was our goal.
[00:04:20.400 --> 00:04:28.720] And then, yeah, we launched this kind of second project because almost more out of curiosity, like what can we do with an LLM API?
[00:04:28.720 --> 00:04:31.680] It took off, so then we kind of merged the products.
[00:04:31.680 --> 00:04:34.480] And then, you know, more and more has happened since then.
[00:04:34.480 --> 00:04:44.560] We've had more ambitions to like actually just like go after these big players, like go after the data infrastructure, like what we can do with AI behind the scenes.
[00:04:44.560 --> 00:04:55.440] And so we figured we'd pivot a little bit away from the chat name because people were kind of pigeonholing us to that name, doing it with the Series A makes sense.
[00:04:55.440 --> 00:05:07.440] And the prize that we were then now set on, we realized that we were going to need a significantly more amount of capital, somewhere between five and 10.
[00:05:07.440 --> 00:05:13.040] And every venture investor is like, take more and go try to get this thing.
[00:05:13.040 --> 00:05:13.840] And you know what?
[00:05:13.840 --> 00:05:16.960] I don't think that's venture investors trying to be evil.
[00:05:16.960 --> 00:05:18.000] They're actually right.
[00:05:18.000 --> 00:05:19.840] They've seen pattern recognition.
[00:05:19.840 --> 00:05:21.680] Like, you're going to need more capital.
[00:05:21.680 --> 00:05:27.520] This is AI, and you're up against people who are raising, you know, hundreds of millions of dollars in some cases.
[00:05:27.520 --> 00:05:29.200] And so, let's talk about that rebrand.
[00:05:29.200 --> 00:05:35.960] So, you're now at fiscal.ai, and your H1 is the modern financial data terminal.
[00:05:35.960 --> 00:05:43.400] Go from idea to confidence with clean, global financial data trusted by the world's leading public market investors.
[00:05:43.400 --> 00:05:45.240] And your site looks gorgeous, by the way.
[00:05:45.240 --> 00:05:47.240] It's a really nice, nice rebrand.
[00:05:47.240 --> 00:05:49.880] So, moving from FinChat to fiscal.
[00:05:49.880 --> 00:05:52.600] Well, fiscal, I mean, fiscal is a great name, especially fiscal.ai.
[00:05:52.600 --> 00:05:55.480] So, the part of that was to not be pigeonholed as just like a chat app.
[00:05:55.480 --> 00:05:56.440] Is that the idea?
[00:05:56.440 --> 00:06:02.680] Yeah, we're like, okay, we've become finance plus AI, and FinChat kind of resembled that.
[00:06:02.680 --> 00:06:07.080] But we would talk to these big bank investors, these public market investors.
[00:06:07.080 --> 00:06:11.720] We had two problems: one, they thought it was just a financial chat.
[00:06:11.720 --> 00:06:16.120] They thought we were maybe like a Bloomberg chat competitor, which was not really true.
[00:06:16.120 --> 00:06:18.280] It was like a full actual data terminal product.
[00:06:18.280 --> 00:06:24.680] So, they're like pleasantly surprised when they came to the demo, but still, like, we were underselling a bit what we were doing.
[00:06:24.680 --> 00:06:42.360] And, two, a lot of big bureaucratic financial buyers had almost all AI chat domains blocked on the server because they didn't want anyone putting in customer-sensitive information, proprietary trading data, stuff like that.
[00:06:42.360 --> 00:06:44.520] And so, we were just always blocked.
[00:06:44.520 --> 00:06:47.880] So, those first demos, no one had ever seen the product before.
[00:06:47.880 --> 00:06:50.760] And that was really hurting our go-to-market.
[00:06:50.920 --> 00:06:51.880] That makes sense.
[00:06:51.880 --> 00:06:59.640] And when, as you said, timing it with the Series A makes a lot of sense because you have the money to acquire the domain and to do the redesign.
[00:06:59.800 --> 00:07:09.160] You touched on it briefly, but I want to double-click on this thing you said of, you know, we had raised the 1.5 million and we had FinChat and it was working.
[00:07:09.160 --> 00:07:11.160] And then we decided to be more ambitious.
[00:07:11.160 --> 00:07:15.000] We decided to take on the, I forget, you know, the terminals of the world or something like that.
[00:07:15.200 --> 00:07:17.040] And that's why you raised the Series A, right?
[00:07:17.040 --> 00:07:20.640] You just need a bunch of money to do something, but tell me what that is.
[00:07:20.640 --> 00:07:22.560] Like, why do you need a bunch of money?
[00:07:22.560 --> 00:07:24.080] Is it just because the others raised it?
[00:07:24.080 --> 00:07:25.040] And who are you competing?
[00:07:25.120 --> 00:07:28.320] Like, maybe talk us through like FinChat, what is it?
[00:07:28.320 --> 00:07:29.760] What was it in 30 seconds?
[00:07:29.760 --> 00:07:36.800] And then, like, what is fiscal and how is it so different that you needed to raise eight figures of funding in order to go after that opportunity?
[00:07:36.800 --> 00:07:38.720] Yeah, it's a fantastic question.
[00:07:38.720 --> 00:07:53.280] So the landscape of our industry today is dominated by primarily three or four massive tens of billions, if not hundreds of billions, each player of market cap on the public market.
[00:07:53.280 --> 00:07:59.680] You know, some of their stocks are worth over $100 billion, many of them in tens of billions of dollars.
[00:07:59.680 --> 00:08:10.640] And so if you think about what they do, they are essentially aggregating financial data with people at scale.
[00:08:10.640 --> 00:08:16.400] Tens of thousands of people manually aggregating financial data at scale.
[00:08:16.400 --> 00:08:22.000] And our vision was: how can we do this better, faster, cheaper with technology?
[00:08:22.320 --> 00:08:31.680] And so as our ambition started to grow in terms of going after that big prize, it became clear that one, we were going to need a larger team.
[00:08:31.680 --> 00:08:35.040] We're going to need a lot more engineering, especially on the data side.
[00:08:35.040 --> 00:08:44.000] And we're going to need a pretty thought-out B2B go-to-market plan that is not going to fly with a million or two in the bank.
[00:08:44.000 --> 00:09:05.000] It's just, like, I think it's a little bit tricky to understand, but one of my investors said with salespeople and the most talented go-to-market folks, they're either going to be the newest people on your team because there's a lot of churn, or the highest paid four or five times more than the CEO at a successful startup.
[00:09:05.240 --> 00:09:20.280] And I was like, that really broke my frame of reference because it's like, oh, wow, they're actually going to make like way, way more money than me if they're closing deals the way that we actually need to go from zero to five to 10 to 20 to 100 million in ARR, right?
[00:09:20.280 --> 00:09:25.080] Like if you just reverse engineer like how much these people should be making, it's significant.
[00:09:25.080 --> 00:09:29.800] So you kind of need a little bit more capital if that's what you want to do.
[00:09:29.800 --> 00:09:31.560] It's not the only route.
[00:09:31.560 --> 00:09:36.440] Like capital is just a method to live in the future, as you would say.
[00:09:36.440 --> 00:09:38.280] And I totally agree with that.
[00:09:38.280 --> 00:09:43.880] The people that I wish I could one day afford or have or work with, I can work with them now.
[00:09:43.880 --> 00:09:45.640] And that's awesome to me.
[00:09:45.640 --> 00:09:46.520] It's a big deal.
[00:09:46.680 --> 00:10:09.160] I like what you touched on with the, what you're investor set, because most founders, especially bootstrap founders, don't realize that, that a salesperson, a GTM person at a startup like yours, if they make, let's say a salesperson makes a million dollars in, it's obviously salary plus commission, they should be generating, I think that it's a loose 10 to one, I think, they should be generating 10 million in ARR for you.
[00:10:09.160 --> 00:10:13.640] So therefore, it's a really good deal for you, even though it sounds a million.
[00:10:13.640 --> 00:10:14.760] What are you insane?
[00:10:14.760 --> 00:10:15.800] We can't afford that.
[00:10:15.800 --> 00:10:18.200] And it's like, that's, I think, what you're touching on, right?
[00:10:18.600 --> 00:10:22.280] Yeah, most folks would be like, oh, I'll never pay someone that much.
[00:10:22.280 --> 00:10:25.480] But then if you say, hey, you know, do you want 10 million in ARR?
[00:10:25.480 --> 00:10:26.440] You're like, of course.
[00:10:26.760 --> 00:10:27.720] I'd pay a million for that.
[00:10:27.880 --> 00:10:28.360] Nobody's going to be a bad person.
[00:10:28.680 --> 00:10:29.080] Exactly.
[00:10:29.080 --> 00:10:30.600] Yeah, yeah, exactly.
[00:10:30.600 --> 00:10:37.400] And so that has taken me a little bit of time to come to terms with a little bit.
[00:10:37.400 --> 00:10:45.360] And once you come to terms with it, then you can really actually build the right team and grow and make the right capital allocation decisions.
[00:10:45.360 --> 00:10:49.040] And sometimes it's not always the cheap, scrappy way.
[00:10:44.920 --> 00:10:50.720] You can still be frugal in other ways.
[00:10:51.280 --> 00:10:54.800] And like I'm recording this from my very cheap office.
[00:10:56.720 --> 00:10:57.840] Yeah, totally.
[00:10:57.840 --> 00:10:59.520] Well, and that's the thing, right?
[00:10:59.520 --> 00:11:03.760] It's like, could you bootstrap or mostly bootstrap this idea?
[00:11:03.760 --> 00:11:06.560] Maybe you would just have to approach it really differently, right?
[00:11:06.560 --> 00:11:12.720] And you would have to grow it slower and you could still maybe build a smaller business that's super profitable.
[00:11:12.720 --> 00:11:19.520] Maybe, you know, I don't know all the intricacies of it with AI and the cost and stuff, but there's usually multiple ways to build these businesses.
[00:11:19.520 --> 00:11:25.280] Super bootstrapped, mostly bootstrapped, and then raising a bit of money and then raising a shit load of money, which you're teetering.
[00:11:25.280 --> 00:11:27.840] To me, you're teetering right on that shit load, Mark.
[00:11:27.840 --> 00:11:37.760] But if you want to go after something that is going to be, that is really crowded, where it is winner take most, and where it's a land grab, that's what it feels like to me.
[00:11:37.760 --> 00:11:40.000] Is that what is happening in your mind?
[00:11:40.000 --> 00:11:48.240] Across just the three players, and this is not including Bloomberg, because Bloomberg is privately held, so it's hard to say what they're doing.
[00:11:48.480 --> 00:11:51.520] Most people think they're doing over 10 billion in ARR.
[00:11:51.520 --> 00:12:02.640] But just the three major public companies in terms of what we're doing in the segments that we're competing, 13 billion in ARR across that kind of oligobly, right?
[00:12:02.640 --> 00:12:06.880] And so it's worth going after this prize in my mind.
[00:12:06.880 --> 00:12:11.440] And I think the more that I've built, the more that this has remained true.
[00:12:11.440 --> 00:12:21.600] Is when we were working on something with a smaller goal and really just focused on that 1 million ARR, which, by the way, is a great goal for everyone who's starting the business.
[00:12:21.600 --> 00:12:35.320] It's not like it was, I was spending less time thinking about this, losing less sleep than I am now about what I want to do with the business or the amount of work required of the weekends of the evenings.
[00:12:29.840 --> 00:12:37.240] I'm all in regardless.
[00:12:37.560 --> 00:12:40.040] So let's go for something really big, right?
[00:12:40.040 --> 00:12:43.080] Like, especially if I'm going to take on investor capital.
[00:12:43.080 --> 00:12:46.440] I mean, I'm running an investor financial data business.
[00:12:46.440 --> 00:12:49.080] I came from this as an investor first.
[00:12:49.080 --> 00:12:58.360] So I take taking someone's capital seriously because I was on the other side of that transaction for 10 years prior.
[00:12:58.360 --> 00:13:05.320] So yeah, I mean, I've been an investor in public markets since the day I turned 18, I could open up my non-registered account.
[00:13:05.480 --> 00:13:09.480] So this has been something that I've thought about for a long, long time.
[00:13:09.800 --> 00:13:13.400] Do you feel like taking this much money?
[00:13:13.400 --> 00:13:16.920] Obviously, it implies that you have to get a lot bigger.
[00:13:16.920 --> 00:13:23.240] Like I'm assuming you want nine figures, meaning 100 million plus of ARR and maybe 10 figures.
[00:13:23.240 --> 00:13:24.680] You know, you're talking 13 billion of ARR.
[00:13:24.680 --> 00:13:25.640] Like you want a check of that.
[00:13:25.640 --> 00:13:28.200] I mean, I don't think it hurt your feelings to get to a billion ARR.
[00:13:28.200 --> 00:13:31.880] So obviously it means your goals, your aspirations, they're just bigger.
[00:13:31.880 --> 00:13:32.920] They have to be.
[00:13:32.920 --> 00:13:39.560] Do you feel like simultaneously that increases your chance of failure?
[00:13:39.880 --> 00:13:42.920] Yes, it does, without a doubt.
[00:13:42.920 --> 00:13:52.440] And I think that this is the one thing that me and my co-founders hummed and hawed on the most as I sat them down because I deal with all the fundraising and talking with investors as the CEO.
[00:13:52.440 --> 00:14:00.120] And I told them, guys, this changes our floor of success has to be so much higher.
[00:14:00.120 --> 00:14:08.920] Our ceiling can be a lot higher, but the floor is now on, you know, level 12 in the elevator, and we're only on level three right now.
[00:14:08.920 --> 00:14:14.440] So we have to go a lot, lot higher for this to be a success now, if we go down this route.
[00:14:14.440 --> 00:14:16.720] So we had to come to terms with that.
[00:14:16.720 --> 00:14:18.320] But like I said, we're still hungry.
[00:14:18.320 --> 00:14:19.600] We still wanted to work for it.
[00:14:19.600 --> 00:14:22.880] We're like, we're probably going to get there anyways, right?
[00:14:22.880 --> 00:14:29.200] It's just going to take us longer if we have to scrap this all together with a million in the bank versus 10.
[00:14:29.200 --> 00:14:30.160] Yeah, that makes sense.
[00:14:30.160 --> 00:17:41.360] Something I'm really happy with is that when Enar and I sat down to figure out the tiny seed investment terms, and this was seven years ago, this 2018, 19, we were just trying to figure out, because there's all these terms, there was indie.bc had kind of this thing where you could pay back and buy back equity and it was like phantom equity but it was like maybe that's interesting but also it's like a little complicated and then other competitors came on the scene with similar things but they like had accidentally or intentionally exploding terms where like if you raised and you didn't pay it back like suddenly you owe they own three times more of your company than they originally like just bizarre stuff right we really wanted we're like equity is equity equity has existed for like a thousand years 800 you know like a very long time and so let's keep it pretty simple we do have a side letter of course because there's salary and participation caps and stuff you couldn't just pay yourself a million dollar salary and not pay tiny seed anything blah blah blah but one of the things we wanted to be really careful about was that we want tiny seed companies after they take our money to have optionality if you never want to raise money again and you want to basically be mostly bootstrapped great if you want to raise a bit of money if you want to raise a lot of money we didn't want that to negatively impact your ability and you are one of several founders who have raised a lot of money seven or eight figures and had at least from my perspective i just signed the docs i don't actually you know lawyer tells me to read them doesn't seem like our terms or any being affiliated with tiny seed had any negative impact on your raise is that true no and i think that you guys have been easy to work with because what i'll say is the newest investor in always wants to be the biggest swing and you know what so they basically that they as the lead will take those terms and previous investors of course there's dilution there's no way around this kind of inevitable feat you get your markup there's a little bit of dilution that's the world of of raising additional capital same with my holdings too right like we're all losing a little bit uh on new money in but the the terms that are coming in with the largest investor is like kind of like they want it their way and you guys have been very easy to work with on like hey they want this way but you're still gonna get this you're still gonna get that you're still a major investor you don't lose any of this this or that and i think that that's a good way to do it right because you're giving us optionality to keep growing if we want to if we didn't want to take any money like that's also fine too right so i think that's the right way to do it because businesses change over time a startup doesn't like when we first met my business was a lot different it was two names ago rub ten dollars a month if i remember it was it was crazy night and day right so you have to be you have to be flexible you have to be pivoting and and you you need investors that are open to that as well because really good investors know that like you're betting on that i'm gonna figure it out and that's something i tell you what, early on with tiny Seed, I did a microconf talk and i remember saying something like, if we start funding, I don't even think tiny Seed existed, but i was like, if i was going to invest in bootstrappers, it would be one round and then they'd never raise again.
[00:17:41.360 --> 00:17:42.480] They'd never have to raise again.
[00:17:42.480 --> 00:17:46.480] And I remember coming off stage and ainar was like, don't say that because you don't know.
[00:17:46.480 --> 00:17:47.600] And it was a real good wake-up.
[00:17:47.680 --> 00:17:49.040] Like, you don't know if they're going to want to raise.
[00:17:49.040 --> 00:17:53.440] Some businesses, we might invest $150,000, $200,000.
[00:17:53.440 --> 00:17:56.320] And it was a very small amount of money in the scheme of things.
[00:17:56.320 --> 00:18:01.600] And if they catch lightning by the tail, they might want to raise three, five, $10, $20 million.
[00:18:01.600 --> 00:18:06.160] And it's like, it's a small subset of Tiny Seed companies, but there are a decent chunk of folks who've done it.
[00:18:06.160 --> 00:18:09.680] And so, A, I'm glad that our terms, because that was the intent was to allow that.
[00:18:09.920 --> 00:18:15.520] Optionality, that was a big thing with Tiny Seed: hey, you can sell for 10, 20 million, but you can also go after the big one.
[00:18:15.520 --> 00:18:18.160] But it is a reminder, maybe to a listener.
[00:18:18.160 --> 00:18:21.120] There are a lot of listeners who are just diehard, bootstrap, bootstrap, bootstrap.
[00:18:21.120 --> 00:18:22.160] I just want a lifestyle.
[00:18:22.160 --> 00:18:23.760] That's what Drip originally was.
[00:18:23.760 --> 00:18:27.440] I was trying to build a little lifestyle business that was going to generate a bunch of profit.
[00:18:27.440 --> 00:18:28.480] And then guess what?
[00:18:28.480 --> 00:18:32.880] I found a bigger opportunity and I just took it in a different direction, right?
[00:18:32.880 --> 00:18:39.440] And like that changed my life because I was open to that possibility of changing my mind.
[00:18:39.440 --> 00:18:42.640] Did you think when you bootstrapped Stratosphere?
[00:18:42.640 --> 00:18:44.560] I had to say, since it's two names ago, I almost said finish.
[00:18:44.720 --> 00:18:51.600] When you bootstrapped Stratosphere in your mind, were you early on like, will never take money?
[00:18:51.600 --> 00:18:54.160] I would take money on the right terms.
[00:18:54.160 --> 00:18:55.440] Definitely want to raise money.
[00:18:55.440 --> 00:18:58.320] You know, where were you on that bootstrapping continuum?
[00:18:58.320 --> 00:19:05.520] I mean, I think I'd be giving myself a lot of credit if I think I had any sort of clue what I was going to do at that point.
[00:19:05.520 --> 00:19:15.280] But generally, I wanted to build something that would, me and my co-founders could pay ourselves a little bit of money, maybe hire a couple people.
[00:19:15.280 --> 00:19:24.640] You know, my dream was to have this kind of bootstrapped, can do whatever I want, cash flow business, so I could live in Bali and like surf every day.
[00:19:24.640 --> 00:19:27.200] That was like kind of my goal.
[00:19:27.200 --> 00:19:31.480] But, you know, things change, the business changes, your personal life changes.
[00:19:32.680 --> 00:19:38.920] You just want different things, especially, you know, when we started this business, I was, I'm 29 now, so I was 26.
[00:19:38.920 --> 00:19:44.440] Like, I didn't know what I wanted to do beyond what I was going to eat for lunch that day.
[00:19:44.440 --> 00:19:49.640] So I don't think I had a grand vision other than I knew I wanted to be an entrepreneur.
[00:19:49.640 --> 00:19:50.760] That's pretty much it.
[00:19:50.760 --> 00:19:55.720] And I knew I wanted to help solve the problems that I saw in finance.
[00:19:56.040 --> 00:19:59.320] And you are open to being open to what comes.
[00:19:59.320 --> 00:20:00.680] And it's like, hey, maybe we'll go bigger.
[00:20:00.680 --> 00:20:01.720] Maybe we'll rebrand.
[00:20:01.720 --> 00:20:03.960] Maybe we'll raise some funding.
[00:20:03.960 --> 00:20:15.080] I'm curious, as I mean, you're a 29-year-old CEO of a company that now has 34 people on your team and you have six more starting shortly.
[00:20:15.080 --> 00:20:18.040] You're about to be the CEO of a 40-person company.
[00:20:18.040 --> 00:20:20.520] There's got to be, I mean, that's bigger than any company I've ever run.
[00:20:20.600 --> 00:20:21.800] Drip was 10 when I sold it.
[00:20:21.800 --> 00:20:27.960] I guess I was running a team within, you know, the acquisition of or the acquirer of maybe 21 at the end.
[00:20:27.960 --> 00:20:31.080] But even Tiny Seed Microconf all combined today is still like 10 people, right?
[00:20:31.080 --> 00:20:33.880] So 40 is significantly more than I would even enjoy.
[00:20:33.880 --> 00:20:35.960] I just don't enjoy managing a lot of people.
[00:20:35.960 --> 00:20:42.280] There has to have been some maybe learnings, growing pains, just all of that stuff.
[00:20:42.280 --> 00:20:47.000] Again, as a, like you're obviously highly competent, very intelligent, but you are, you're a young dude.
[00:20:47.000 --> 00:20:49.320] Like I don't think you've managed 40 people before.
[00:20:49.320 --> 00:20:52.280] So what is this feeling like for you these days?
[00:20:52.280 --> 00:20:59.160] When we hit 25 people at the end of last year, I had a major wake-up call.
[00:20:59.160 --> 00:21:03.520] Like it like slapped me in the face once we hit 25.
[00:21:03.520 --> 00:21:09.960] And I hadn't built the right infrastructure for a company to exist at 25 people.
[00:21:10.280 --> 00:21:16.480] We were just flying by the seat of our chair like it was just me and my three co-founders.
[00:21:16.480 --> 00:21:18.720] And then I woke up and there's 25 people.
[00:21:18.720 --> 00:21:24.560] And it's like, whoa, okay, we gotta like see, I have to actually become a CEO.
[00:21:24.560 --> 00:21:37.200] And so I started trying to learn and trying to focus and just like take the realization that this is not just me and my co-founders hacking around away trying to make money on the internet anymore.
[00:21:37.200 --> 00:21:42.800] This is like people are making real money, real salaries, real lives working for us.
[00:21:42.800 --> 00:21:48.720] And we need to build a really sustainable, scalable company as we can go.
[00:21:48.720 --> 00:21:54.000] And so that's the wall, I would say, is 25.
[00:21:54.320 --> 00:22:01.280] And I was like, okay, I say I've been the CEO of this company for two years, but I haven't been.
[00:22:01.280 --> 00:22:02.640] Now I need to be.
[00:22:02.640 --> 00:22:06.480] And I think I've gotten a lot better, honestly.
[00:22:06.480 --> 00:22:13.280] What were some of the things, what were some examples of things that maybe weren't working that you had to then add structure in order to fix?
[00:22:13.280 --> 00:22:17.760] A book I'd recommend to everyone is called The Great CEO Within.
[00:22:17.760 --> 00:22:20.800] It's the tactical guide to company building.
[00:22:20.800 --> 00:22:23.600] It's short, it's like 200 pages.
[00:22:23.600 --> 00:22:26.720] It's just step-by-step advice.
[00:22:26.720 --> 00:22:35.840] There's lots of amazing CEOs who have chimed in in certain sections, whether it's, you know, Brian Armstrong of Coinbase or the guy who did Clearbit.
[00:22:35.840 --> 00:22:39.920] Like a lot of people came together to build this book.
[00:22:39.920 --> 00:22:44.640] And it's a book that every Sequoia founder is given when they invest in them.
[00:22:44.640 --> 00:22:46.400] And so I read that book.
[00:22:46.400 --> 00:22:57.200] That really helped me frame around this idea of if I have to do it twice, it needs to be an actual process or written down somewhere.
[00:22:57.200 --> 00:23:04.200] A company, Wikipedia, it can be as simple as just utilizing a Google Drive better and file systems.
[00:22:59.760 --> 00:23:05.560] Just little things like that.
[00:23:05.800 --> 00:23:08.600] If I have to do it twice, it needs to be a system.
[00:23:08.600 --> 00:23:16.840] Because there's a lot of stuff you're going to start having to repeat all the time, whether it's hiring, whether it's operational stuff, whether it's sales.
[00:23:16.840 --> 00:23:21.800] I was wasting so much time starting from scratch every time I was doing something.
[00:23:22.120 --> 00:23:24.840] So that really, really helped.
[00:23:24.840 --> 00:23:33.800] And then, secondly, around how to properly encourage my employees to succeed and tell them that they're doing a good freaking job.
[00:23:33.800 --> 00:23:37.080] Because a lot of them are doing an amazing job.
[00:23:37.080 --> 00:23:43.240] And I think that before I was just, I assumed that they knew that I thought they were doing a great job.
[00:23:43.240 --> 00:23:48.440] It is amazing what happens when you tell people just some simple recognition of how good of a job they're doing.
[00:23:48.440 --> 00:23:55.800] Because there's some people who are killing it at our company, like crushing it, working so hard and they're so happy here.
[00:23:55.800 --> 00:24:01.000] But, you know, it is amazing what some recognition or some recognition on a team call could do.
[00:24:01.000 --> 00:24:02.200] Some structure.
[00:24:02.200 --> 00:24:06.200] Every Friday, every single person in the company talks at our meeting now.
[00:24:06.200 --> 00:24:11.160] Before, it would just be me like telling them what we're going to do next week.
[00:24:11.160 --> 00:24:16.920] Now it's every single person telling me what they're going to do and asking me how I can help them.
[00:24:16.920 --> 00:24:21.480] So that has massively changed the way that the business is operated, I would say.
[00:24:21.480 --> 00:24:24.200] But it's not hard, Rob.
[00:24:24.200 --> 00:24:27.800] We're doing stuff that's way harder than these things that I've had to figure out.
[00:24:27.800 --> 00:24:30.680] This is easy, easy stuff, but it goes a long way.
[00:24:30.680 --> 00:24:32.520] Yeah, that's a great book recommendation, by the way.
[00:24:32.520 --> 00:24:38.200] I don't know that I've actually read it, but I have heard, I've seen it, and I know folks recommend it.
[00:24:38.200 --> 00:24:39.720] No, no fluff in that book.
[00:24:39.720 --> 00:24:40.600] It's very straightforward.
[00:24:40.760 --> 00:24:41.240] Yeah, it's tight.
[00:24:41.480 --> 00:24:42.200] Yeah, it's real tight.
[00:24:42.200 --> 00:24:43.560] Yeah, 200 pages.
[00:24:43.560 --> 00:24:48.000] Do you enjoy being the CEO of a 40-person company specifically?
[00:24:48.000 --> 00:24:49.280] Sometimes no.
[00:24:49.600 --> 00:24:53.200] Yeah, yeah, I was going to say, because there's got to be some hard days.
[00:24:53.200 --> 00:24:55.520] There's got to be some complicated days with it.
[00:24:55.520 --> 00:25:07.440] There's some complicated days, but there are some days that are so freaking good as well that, you know, the highs and the lows are certainly there.
[00:25:07.440 --> 00:25:14.080] And I try to, if I don't manage myself with the highs and the lows, my employees know it and feel it.
[00:25:14.080 --> 00:25:16.800] So I have to be pretty even keel.
[00:25:16.800 --> 00:25:20.560] So there are certainly days that are not as fun.
[00:25:20.560 --> 00:25:23.280] There are certainly days that are a ton of fun.
[00:25:23.280 --> 00:25:27.680] But at the end of the day, I don't want to do anything else differently right now.
[00:25:27.680 --> 00:25:37.200] So it would be a problem for me when there was hard days if I was just like, oh, there's something that I really want to do that's not this.
[00:25:37.520 --> 00:25:39.040] But I don't have that.
[00:25:39.040 --> 00:25:41.120] I want to see this thing work really well.
[00:25:41.120 --> 00:25:43.280] So that's, that kind of keeps me going.
[00:25:43.280 --> 00:25:43.760] Yeah.
[00:25:43.760 --> 00:25:51.040] I think growth also always used to keep, like, I know your growth curve, obviously, because I'm an investor in AC and it's like you're growing very fast.
[00:25:51.040 --> 00:25:56.960] And for me, MRR, ARR going up into the right, it made a lot of ills go away.
[00:25:56.960 --> 00:25:58.480] For me, I was just like, you know what?
[00:25:58.480 --> 00:25:59.120] It's working.
[00:25:59.120 --> 00:25:59.840] This is hard.
[00:25:59.840 --> 00:26:01.120] It's not supposed to be easy.
[00:26:01.120 --> 00:26:04.640] But if you're doing all this grind and it's flat, it's terrible.
[00:26:04.640 --> 00:26:08.000] Like it's the worst because you're just like, none of this is worthwhile.
[00:26:08.000 --> 00:26:08.960] I'm wasting my time.
[00:26:08.960 --> 00:26:10.560] I'm going, why am I doing this?
[00:26:10.560 --> 00:26:14.560] You know, so it growth cures most ills, I think.
[00:26:14.560 --> 00:26:17.200] ARR growth solves a lot of problems.
[00:26:17.200 --> 00:26:17.600] Yeah.
[00:26:17.840 --> 00:26:20.720] Including my ability to sleep well at night.
[00:26:20.720 --> 00:26:21.840] Exactly.
[00:26:22.160 --> 00:26:22.560] All right.
[00:26:22.560 --> 00:26:29.040] So I want to ask you, we were talking offline and you threw some bullets into a dock for me to help guide this conversation.
[00:26:29.040 --> 00:26:41.320] And one of the things that you said was something we could talk about was why I shut down a B2B product that went from zero to one and a half million ARR in 12 months and then I shut it down.
[00:26:41.320 --> 00:26:44.520] Talk us through what was that product and why.
[00:26:44.840 --> 00:27:00.840] We started licensing our AI co-pilot product, which is basically you could converse with all the financial data, get it to build you graphs, get you to summarize transcripts, slide decks, everything was pre-loaded into there.
[00:27:00.840 --> 00:27:05.800] We exposed that product while we were trying to build a ton of other products.
[00:27:05.800 --> 00:27:08.280] So it was just like a lot was going on.
[00:27:08.280 --> 00:27:11.720] It was a bit of a distraction, but the money was flowing in.
[00:27:11.720 --> 00:27:18.440] It went from zero to a million and a half of ARR, growing, you know, 20% a month consistently, even when I shut it down.
[00:27:18.440 --> 00:27:23.320] It was probably, it would probably be like two and a half, three today, maybe more.
[00:27:23.320 --> 00:27:26.600] The problem with it was we were signing big customers.
[00:27:26.600 --> 00:27:29.400] One of them was $250,000 a year.
[00:27:29.400 --> 00:27:31.480] Several were in the hundreds of thousands of dollars.
[00:27:31.720 --> 00:27:34.040] Some on the just tens of thousands of dollars.
[00:27:34.040 --> 00:27:39.880] And a lot of customers were coming offline pretty quick and telling us quickly that they were not going to renew.
[00:27:39.880 --> 00:27:48.680] And the reason for that was we solved a key problem at one point that ChatGPT couldn't handle any of these queries very well.
[00:27:48.680 --> 00:27:50.840] That problem went away.
[00:27:50.840 --> 00:27:56.280] And the foundational model started to kick our asses at our own game.
[00:27:56.280 --> 00:27:58.280] And so we started to see the writing on the wall.
[00:27:58.280 --> 00:28:01.240] We're like, okay, this is not actually what we're good at.
[00:28:01.240 --> 00:28:05.480] Us doing rag for them and solving this quick problem for these customers.
[00:28:05.480 --> 00:28:10.120] It's probably a quick solve because they want AI on their platform yesterday.
[00:28:10.440 --> 00:28:13.960] The CEO's begging the product team, why is there an AI not on our product?
[00:28:13.960 --> 00:28:23.440] We were a quick solution, a quick fix for them, but it wasn't the right solution for them because then they would say to us, How do I connect my customer service bot to this as well?
[00:28:23.440 --> 00:28:28.640] Or how do I connect my customer clients are asking how they do their own account openings?
[00:28:28.640 --> 00:28:32.800] And it's getting confusing because this was a very narrow product.
[00:28:32.800 --> 00:28:34.960] And we said, Okay, sorry, I can't help you with that.
[00:28:34.960 --> 00:28:38.640] Like, you're gonna have to build it from scratch with our data.
[00:28:38.640 --> 00:28:41.200] And then they started doing that.
[00:28:41.200 --> 00:28:43.360] And that had product market fit.
[00:28:43.360 --> 00:28:56.400] And so we shut down this out-of-the-box solution that so many people loved right away because the actual slower, longer implementation were customers that I think will be with us forever.
[00:28:56.400 --> 00:29:06.640] And that is a materially different type of anxiety when you see 30 customers sign up and 15 of them turn before three months in.
[00:29:07.600 --> 00:29:08.320] That's brutal.
[00:29:08.560 --> 00:29:10.800] Terrible, terrible.
[00:29:10.800 --> 00:29:12.640] So we just said, screw it.
[00:29:12.640 --> 00:29:15.520] We got, you know, we're going to shut it down with the financing.
[00:29:15.520 --> 00:29:17.280] And that's what it is.
[00:29:17.280 --> 00:29:18.640] That is what it is.
[00:29:18.640 --> 00:29:19.040] Wow.
[00:29:19.040 --> 00:29:19.360] Yeah.
[00:29:19.360 --> 00:29:20.640] These are hard decisions.
[00:29:20.640 --> 00:29:24.160] Did you feel hard decisions with incomplete information?
[00:29:24.160 --> 00:29:26.160] Did you have much doubt when you did that?
[00:29:26.160 --> 00:29:31.280] Because that's a one-way door-ish type of thing that's really hard to undo.
[00:29:31.280 --> 00:29:35.040] Were you kind of like convicted and you were like, no, this is the right way?
[00:29:35.040 --> 00:29:38.960] Or were you like, oh, he and Han trying it on for weeks and months?
[00:29:38.960 --> 00:29:51.120] I knew it was the right decision when I was seeing how much it was causing issues with our development team for building the long-term product that we actually envisioned.
[00:29:51.120 --> 00:29:58.560] Because there was a lot of bugs, it was a lot of customer service requests that we just were not getting for our core foundational product.
[00:29:58.560 --> 00:30:00.680] People were way more happy there.
[00:30:01.240 --> 00:30:12.680] So, a combination of churn and distraction from the dev team was enough for me to go, look, this is not what's going to make this business a success.
[00:30:12.680 --> 00:30:19.800] So, reverse engineering that, yeah, it's tough to say no to that much revenue when you're at our size, but I think it was the right call.
[00:30:19.800 --> 00:30:21.960] It's still really early to say, right?
[00:30:21.960 --> 00:30:27.400] Like, it sucks when customers ask us today if they can come buy it.
[00:30:27.400 --> 00:30:30.440] And I'm like, no, you can't.
[00:30:30.440 --> 00:30:31.800] I gotta say, no.
[00:30:32.120 --> 00:30:34.680] Turning down revenue is the worst.
[00:30:34.680 --> 00:30:39.960] Yeah, the worst is saying yes to revenue and having it churn, but the second worst is turning down revenue.
[00:30:40.360 --> 00:30:41.720] I want to switch topics a little bit.
[00:30:41.720 --> 00:30:46.600] I just have maybe two more questions for you, but one is about you have three co-founders.
[00:30:46.600 --> 00:30:48.120] So, there's four of you total.
[00:30:48.120 --> 00:30:58.360] And I'm curious, we talked about this last time we recorded, so I won't go too far into it, but I'm curious now that you're here where you are with a 40-person team and you've raised all this money.
[00:30:58.360 --> 00:31:06.760] What's maybe the biggest positive to having that many co-founders and the biggest negative that you've seen?
[00:31:06.760 --> 00:31:18.040] The biggest positive is that there are four of us across the different parts of our business that have an amazing leader on day one.
[00:31:18.040 --> 00:31:19.480] That's the biggest positive.
[00:31:19.480 --> 00:31:27.000] So, me as a CEO, my chief product officer, one of my co-founders, my CTO, one of my co-founders.
[00:31:27.000 --> 00:31:31.480] So, they run tech and product and they are outstanding at what they do.
[00:31:31.480 --> 00:31:36.680] And then, my CEO, Adrian, runs all of our data operations and just operations in general.
[00:31:36.680 --> 00:31:40.520] And he is, he's the dream hire, right?
[00:31:40.520 --> 00:31:46.400] So, I had kind of the dream hire on day one from day one, building the business.
[00:31:44.680 --> 00:31:50.880] And to me, that is super, super valuable, without a doubt.
[00:31:51.200 --> 00:31:52.720] Plus, I love these guys.
[00:31:52.720 --> 00:31:55.680] So it's nice to, it's great hanging out with them every day.
[00:31:55.840 --> 00:31:57.520] So it's just a good team.
[00:31:57.520 --> 00:31:58.640] We get along great.
[00:31:58.640 --> 00:32:13.040] The biggest downside, I guess, would be I could see the potential for clashing when it comes to decision making, hiring, product decisions, long-term vision.
[00:32:13.040 --> 00:32:24.880] But I think if you were to ask my co-founders, they would say that I've earned their trust to unequivocally make almost all of those decisions and ask them if it's okay.
[00:32:24.880 --> 00:32:26.560] And they give me the green light.
[00:32:26.560 --> 00:32:32.720] But we don't pose strategic questions and say, what do we think?
[00:32:32.720 --> 00:32:36.240] I pose the strategic questions, say, this is what I'm doing.
[00:32:36.240 --> 00:32:37.920] This is where we're going to go.
[00:32:37.920 --> 00:32:41.440] Does anyone have any major issues with this?
[00:32:41.440 --> 00:32:44.960] If so, then speak up, then we'll reroute.
[00:32:44.960 --> 00:32:51.840] But if not, and you, you know, I've given, I've gained your trust and your leash to be able to make these decisions, then let's go.
[00:32:51.840 --> 00:32:54.400] So everyone focuses on what they're good at.
[00:32:54.400 --> 00:32:59.360] And so I think the pros majorly outweigh any cons, in my view.
[00:32:59.360 --> 00:33:03.600] Yeah, well, it seems to be working for you, too, you know, with the growth and the success.
[00:33:03.600 --> 00:33:06.880] Obviously, raising funding is a tool and it's a milestone.
[00:33:06.880 --> 00:33:08.320] It's not the finish line.
[00:33:08.560 --> 00:33:10.960] You and I both know this, so I don't want to, that's not worth saying.
[00:33:11.120 --> 00:33:13.680] The finish line got a lot further away when you did this money.
[00:33:13.920 --> 00:33:15.440] We just extended the finish line.
[00:33:15.440 --> 00:33:19.360] So, last question for me today is regarding Tiny Seed.
[00:33:19.360 --> 00:33:26.800] When this episode goes live, Tiny Seed applications will open like a week or two later, right, for our next batch, our 16th batch or something like that, September 1.
[00:33:27.120 --> 00:33:30.760] And I'm curious, I don't know quite how to ask this question.
[00:33:31.080 --> 00:33:37.880] Maybe it's like, what are the top three or four things you and your team, you know, your founding team got out of Tiny Seed?
[00:33:38.200 --> 00:33:44.760] Or maybe it's if someone's on the fence, they're listening to this, what would be the benefits for them joining?
[00:33:44.760 --> 00:33:48.600] And maybe you could even say, well, if you're, if you want to do X, don't join Tiny Seed.
[00:33:48.600 --> 00:33:49.160] You know what I mean?
[00:33:49.160 --> 00:33:50.440] Like the pros and cons.
[00:33:50.440 --> 00:33:57.880] We don't have to go full pros and cons, but it's kind of like, what did you get out of Tiny Seed that like would lead someone to apply and want to do it?
[00:33:57.880 --> 00:33:59.240] Yeah, there's three things.
[00:33:59.240 --> 00:34:05.240] So if you're comfortable with saying, I think it was 200K that we raised from you guys.
[00:34:05.560 --> 00:34:11.960] And so at that time, nowadays, I'm like, that's like, what do I do with that, right?
[00:34:11.960 --> 00:34:12.360] Yeah.
[00:34:12.360 --> 00:34:17.560] But at that time, when you have 10,000 in the bank, it's everything, right?
[00:34:17.560 --> 00:34:19.800] Like, so it's that frame of reference.
[00:34:19.800 --> 00:34:26.920] So that did materially actually help us, I'm not going to lie, especially with our vision, which was, it was in a sweet spot for us at the time.
[00:34:26.920 --> 00:34:31.160] Of course, you know, the vision changed, the ambition changes, but at the time, it was the right amount.
[00:34:31.160 --> 00:34:42.200] The second thing that I think was super helpful was just, yeah, just early on, we were using you and ANR a lot around like pricing, which customers are working.
[00:34:42.200 --> 00:34:43.960] What do you think about this strategic?
[00:34:43.960 --> 00:34:46.600] Is freemium versus non?
[00:34:46.760 --> 00:34:59.960] Like some of the basic questions that you talk about on this podcast a lot are super helpful for anyone listening, but it's even more helpful if we can talk specifically about my business, right?
[00:35:00.280 --> 00:35:07.800] Like I can learn from Joe's other business, but when we're talking specifically about my business, it's obviously a lot more tangible.
[00:35:08.040 --> 00:35:09.640] So that would be the second thing.
[00:35:09.640 --> 00:35:21.760] And then the third thing is, I don't actively participate in the Slack community, but if I have a question, I know it's going to get answered really well by like 30 people in the matter of hours.
[00:35:22.080 --> 00:35:28.880] So I would say I am more of a receiver of information more than a giver on there.
[00:35:28.880 --> 00:35:31.440] So it's probably more of a one-way street for me.
[00:35:31.440 --> 00:35:36.240] It should probably be a little bit more reciprocal, but that's just kind of what I get out of it.
[00:35:36.400 --> 00:35:38.320] It's amazing for me, to be honest.
[00:35:38.320 --> 00:35:38.800] I'm glad.
[00:35:38.800 --> 00:35:46.160] And that, you know, it's funny with the first batch or two, the Slack group was obviously tiny because there were 10 founders and then 20 founders or whatever.
[00:35:46.160 --> 00:35:49.440] And Anar and I used to have to answer a lot of the questions.
[00:35:49.440 --> 00:35:51.280] And it was just like, well, no one else knows.
[00:35:51.280 --> 00:35:52.880] And so I am going to give my best answer.
[00:35:52.880 --> 00:35:54.400] And there'd be other stuff trickling.
[00:35:54.400 --> 00:36:01.280] Now, by the time I, we have an advice needed channel for those who don't know, you know, by the time I get to any question, there's already five responses.
[00:36:01.280 --> 00:36:04.000] And I tend to look through and be like, ooh, that's smarter than what I would have said.
[00:36:04.000 --> 00:36:06.000] Oh, he's done it more recently than I have.
[00:36:06.000 --> 00:36:07.120] Oh, she has better insight.
[00:36:07.440 --> 00:36:15.360] And it's usually like what they said, you know, with an arrow up, or maybe I have a little bit to add, but it's like, I'm no longer the expert.
[00:36:15.440 --> 00:36:18.320] I don't have to be the expert me, Rob Walling doesn't have to be the expert on everything.
[00:36:18.320 --> 00:36:19.520] And I shouldn't have to be.
[00:36:19.520 --> 00:36:23.840] Like, because there are 300 something, there's 204 companies and I think it's 310 founders.
[00:36:23.840 --> 00:36:28.240] I don't know the exact number, but very knowledgeable people like yourself that are really knee deep.
[00:36:28.240 --> 00:36:38.320] You know, if someone's like, hey, I want to know how ML stuff and data and financial whatever, like me, I don't really know, but like you or your co-founder Kevin or one of your other founders is going to really know it.
[00:36:38.880 --> 00:36:44.400] Even stuff like this, we're a Toronto, Canada-based startup and there's a Canada channel.
[00:36:44.400 --> 00:36:59.640] And we have specific questions around our tax situation or our HR situation that you know we're a little underserved because most of those questions on the internet or in these types of Slack communities are specifically about U.S.
[00:36:59.600 --> 00:37:01.080] tax or U.S.
[00:36:59.840 --> 00:37:01.720] regulations.
[00:37:02.040 --> 00:37:08.200] So, for us to have our little corner where we know we're dealing with the same context is pretty helpful.
[00:37:08.200 --> 00:37:09.080] That's great.
[00:37:09.080 --> 00:37:11.800] Well, Braden, thanks so much for coming back on the show, man.
[00:37:11.800 --> 00:37:17.320] If folks want to keep up with you on the internet, of course, you're BradoCapital on X Twitter.
[00:37:17.320 --> 00:37:21.480] And if they want to see what you're building, it's at fiscal.ai.
[00:37:21.480 --> 00:37:22.760] Thanks again for joining me.
[00:37:22.760 --> 00:37:23.560] Thank you.
[00:37:23.560 --> 00:37:26.440] Thanks again to Braden for coming back on the show.
[00:37:26.440 --> 00:37:29.960] And thanks to you for listening this week and every week.
[00:37:29.960 --> 00:37:33.800] This is Rob Walling signing off from episode 787.