How Justin Duke is building Buttondown into the perfect bootstrapped business

February 7, 2025

Key Takeaways

Founders should prioritize building a company they genuinely enjoy working on, even if it means making calculated risks and avoiding the trap of simply creating a job they dislike.
Effective marketing, especially for SaaS products, often involves a combination of conventional strategies and leveraging relationships with influential users, with a focus on understanding and serving specific niches.
Balancing independence and agency with a safety net is crucial for founders, ensuring that while they have the freedom to make quick decisions, there’s also infrastructure in place to support them during challenging times.

Segments

Founder’s Enjoyment & Role (00:04:23)

Key Takeaway: Founders must actively design their roles to avoid creating a job they dislike by carving out enjoyable tasks like engineering and customer interaction, rather than solely focusing on management.
Summary: Justin discusses his deliberate approach to ensuring he enjoys his work by prioritizing engineering, product exploration, and customer interaction, while delegating management tasks to avoid becoming solely a ‘CEO’ doing things he’s not passionate about.

Marketing Strategy & Niches (00:07:16)

Key Takeaway: Button Down’s marketing success is heavily influenced by large users broadcasting their use of the tool, but to break into new non-technical niches, a more deliberate marketing approach is needed beyond relying on existing evangelists.
Summary: The discussion shifts to marketing, where Justin notes that while conventional methods are ‘fine,’ the biggest growth driver has been word-of-mouth from influential users. He acknowledges the need for targeted marketing to expand into new, non-technical niches.

Targeting Technical Users (00:09:03)

Key Takeaway: Aggressively targeting technical users through clear language like ‘Markdown’ on the website can effectively signal the product’s intended audience and attract customers who are a better fit, even if it narrows the total addressable market.
Summary: Justin explains the strategic decision to double down on targeting technical users, using ‘Markdown’ as a signal to attract the right audience and deter those who might not be a good fit, focusing on polish and service to retain these users.

Content Consumption & Fun (00:15:34)

Key Takeaway: Running a company should include elements of fun and personality, such as seasonal website changes, as this is a core reason for pursuing entrepreneurship and can lead to more authentic customer connections.
Summary: The conversation concludes with a discussion on content consumption and the importance of having fun in running a company, exemplified by seasonal website changes, emphasizing that this enjoyment is a key motivator for entrepreneurship.

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Processing Time: September 11, 2025 at 01:20 PM
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Caption Count: 177 captions

Prompts Used

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Transcript section:
[00:00:01.280 --> 00:00:10.080] I feel like if every cliche about marketing is true, it's just like you're trying a bunch of stuff every now and then something works and you're like, okay, let's try that 50 more times.
[00:00:10.080 --> 00:00:13.920] And then maybe if you're lucky, it actually does repeat and it wasn't just a fluke.
[00:00:13.920 --> 00:00:19.120] Hello, and welcome back to Indiebytes, the podcast where I bring you stories of fellow indie hackers in 15 minutes or less.
[00:00:19.120 --> 00:00:24.640] Today I'm joined by Justin Duke, who is the founder of Button Down, a simple email tool he launched in 2017.
[00:00:24.640 --> 00:00:31.280] Justin was last on the podcast two years ago when he just hit 15k MRR and had left his role at Stripe to focus on Button Down full-time.
[00:00:31.280 --> 00:00:34.080] I was struck then by Justin's well-thought-out approach to building.
[00:00:34.080 --> 00:00:40.320] He makes calculated risks and shares a lot of his learnings on his blog, Applied Cartography, which is an essential read for any indie hackers.
[00:00:40.320 --> 00:00:45.680] This episode, I catch up with Justin to hear how he's grown a team to eight people and his approach to building a company he loves.
[00:00:45.680 --> 00:01:00.160] This is a cut-down version of an hour-long catch-up I had with Justin, which I'm going to make available on the Indiebytes membership at indiebytes.com/slash membership, where we discuss his personal blog, how he structures his time as a new parent, and we go deeper into hiring high-agency unicorns.
[00:01:00.160 --> 00:01:03.200] I also want to thank my sponsor EmailOctopus for supporting the show.
[00:01:03.200 --> 00:01:12.240] Now, obviously, Email Octopus are a competitor to the product of today's guests, so I asked Justin if he was okay with it, and his response shows exactly how all founders should approach competitors.
[00:01:12.240 --> 00:01:22.800] Near and dear to my heart, they've been like posting sort of their bootstrap stuff for years, and they have a very rich history of talking about their growth.
[00:01:23.200 --> 00:01:32.800] My philosophy with the email space is always like my biggest competitors are the tools that have been around for 30 years, not 10 years.
[00:01:33.280 --> 00:01:38.160] That's where the truly subpar user experiences are happening right now.
[00:01:38.160 --> 00:01:42.960] So, if you want to give Email Octopus a go, head to emailoctopus.com or hit the link in the show notes.
[00:01:42.960 --> 00:01:46.000] Another quick note: Justin is using a Blue Yeti microphone.
[00:01:46.000 --> 00:01:47.120] You know my thoughts on that.
[00:01:47.120 --> 00:01:49.680] So, I can only apologize for his audio quality.
[00:01:49.680 --> 00:01:52.160] I promise you'll forget about it after a couple of minutes.
[00:01:52.160 --> 00:01:58.240] We kick off this episode talking about how Button Down is going two years after our previous Indiebytes episode.
[00:01:58.960 --> 00:01:59.960] It was so funny.
[00:01:59.680 --> 00:02:04.440] I listened back to the episode we did, what, like almost two years ago.
[00:02:04.760 --> 00:02:10.760] It sounded like I was talking about me and Button Down from like 10 years ago.
[00:02:10.760 --> 00:02:13.400] The business itself doing really, really well.
[00:02:13.400 --> 00:02:18.840] I can no longer really share revenue numbers because we've just kind of grown to the point, but very healthy growth.
[00:02:18.840 --> 00:02:30.280] After leaving Stripe, there was like a clear sort of mission in my head, which was like, I want to just figure out if this is sustainable for me from like an existential point of view, from a financial point of view.
[00:02:30.280 --> 00:02:34.120] Like this feels good to like spend my time working on this full-time.
[00:02:34.120 --> 00:02:37.480] And then once we kind of hit that milestone, I was like, yeah, I like this.
[00:02:37.880 --> 00:02:39.400] This is what my days are.
[00:02:39.400 --> 00:02:41.240] Then it's like, okay, what's next?
[00:02:41.240 --> 00:02:43.960] Because you can always grow a company.
[00:02:43.960 --> 00:02:47.080] Like the default position is to keep trying to grow it.
[00:02:47.080 --> 00:02:50.840] ButtonDown had reached the point where I couldn't just keep doing it myself.
[00:02:50.840 --> 00:02:55.000] Like I know I was having a kid, I had other interests and I didn't want to work 80-hour weeks.
[00:02:55.000 --> 00:02:56.600] So it's like, do you hire a team?
[00:02:56.600 --> 00:03:02.280] And then if you hire a team, you're shifting back into management when really what I like doing is engineering.
[00:03:02.280 --> 00:03:35.560] And a lot of the past year for me has kind of been navigating that maze of figuring out a way to keep having it be a business that I legitimately enjoy spending all of my time thinking about and getting my hands dirty in, while also still like making sure it grows, making sure the new folks on the team aren't thrown off into the deep end, making sure new customers are still having a great experience and kind of like hitting that next level beyond just, okay, this is not quite an escape velocity, but the fight to survive, that part is done.
[00:03:35.560 --> 00:03:38.600] Like, button Down is a healthy and thriving business.
[00:03:38.600 --> 00:03:40.920] Now, what are the next sets of goals?
[00:03:40.920 --> 00:03:45.040] You're absolutely right because I speak to founders that fall into this trap.
[00:03:45.040 --> 00:03:49.760] There was one chap I met the other day who'd like grown his business to 30 cameras.
[00:03:44.840 --> 00:03:50.560] That's very healthy.
[00:03:50.800 --> 00:03:54.640] And he was just like, Am I just like chasing growth now?
[00:03:54.960 --> 00:03:55.520] Is this it?
[00:03:55.520 --> 00:03:56.960] He was just, he was bored.
[00:03:56.960 --> 00:03:58.720] He was like, what's next?
[00:03:58.720 --> 00:04:11.040] And you've got so many of these indie people that like just getting something off the ground, getting it to a few K MRR, and then don't like once they're now in the business to actually keep working on it and like keep motivation going.
[00:04:11.040 --> 00:04:19.680] Or you've got other people who do like the fact they've built themselves a job where they have pretty much full control over what they do and they're very passionate about it.
[00:04:19.680 --> 00:04:23.840] So I'm guessing you've put a lot of thought into making sure it's in the latter camp.
[00:04:23.840 --> 00:04:38.880] Yeah, one of the things that has been sort of like priority number one is, and I've run into this phrase a lot, but like I really wanted to avoid making myself a job that I hated.
[00:04:38.880 --> 00:04:43.200] And like, I think it's very obvious to me how that would happen.
[00:04:43.200 --> 00:04:58.960] Of like, if I just carve out all the things that I really love, which is like doing engineering work, doing like interesting product exploration, talking to customers and users, and I say, these are no longer worth my time because they're low leverage.
[00:04:58.960 --> 00:05:03.120] I'm going to hire those positions out and I'm going to manage those people instead.
[00:05:03.120 --> 00:05:12.000] And what I'm left with is all the stuff like quote-unquote a CEO is supposed to do, but also not what I'm particularly passionate about or frankly, even good at.
[00:05:12.000 --> 00:05:17.600] And figuring out a way to balance those two things has been really, really key, especially the past like six months.
[00:05:17.920 --> 00:05:19.680] So, how big's a team?
[00:05:19.680 --> 00:05:20.680] How's growth?
[00:05:20.680 --> 00:05:23.760] And what are you spending your time on day to day-to-day?
[00:05:23.760 --> 00:05:33.880] Yeah, so we're around eight folks total, and that's a mix of mostly contractors, a couple W-2s, myself included.
[00:05:34.200 --> 00:05:45.240] And what my day-to-day looks like is less around like line-level management of, okay, it's time for everyone to open linear and we're going to like carve out the tasks and do all that.
[00:05:45.240 --> 00:06:00.360] Like, I've been very particular about wanting to work with folks who feel really comfortable with ambiguity and sort of getting their hands dirty and doing things that might not necessarily be the case at larger companies.
[00:06:00.360 --> 00:06:17.240] And so, like, the example I always give is most large companies, even really, really good ones, design like the IC engineer role such that the median IC engineer doesn't have to like do design or talk with customers or look at a support inbox or any of those things.
[00:06:17.240 --> 00:06:41.480] And my philosophy has sort of been the opposite: I feel very strongly that that's where the best product work comes from is being able to context switch from a, this customer wrote in asking about this thing, and they think it's a bug, but actually, what this is, is like a better UX waiting to happen, and I can connect those dots because I'm like looking at all of these things.
[00:06:41.480 --> 00:06:58.920] And so, finding and working with folks who are really, really good at that level of thinking, as opposed to like a you can imagine an abstract like contract engineer who's just like, give me a bunch of tickets and I'm gonna knock them out, and like that is my relationship with this business.
[00:06:58.920 --> 00:07:07.640] And that to me has been really, really rewarding because it's also it removes some of the things that I didn't love about engineering management, which was the administrivia.
[00:07:07.640 --> 00:07:16.880] Instead, a lot of the engineering conversations I get to have are closer to like design or architectural conversations, which feels much more interesting and rewarding to me.
[00:07:16.880 --> 00:07:18.560] Any marketing highs?
[00:07:18.560 --> 00:07:19.440] Not yet.
[00:07:19.440 --> 00:07:22.960] That's probably going to change at some point.
[00:07:22.960 --> 00:07:40.640] The thing that has always been like a good problem and a bad problem with Button Down's growth is like we have all of the conventional SaaS playbook things of like you do referrals and you mess with AdWords and you've got programmatic SEO and all of these things.
[00:07:40.640 --> 00:07:42.400] And they're all like fine.
[00:07:42.400 --> 00:07:50.720] And then someone who has a massive following starts to use ButtonDown and like broadcasts to their subscribers, hey, we're using ButtonDown now.
[00:07:50.720 --> 00:07:53.520] And like that just dwarfs everything else.
[00:07:53.520 --> 00:07:58.720] And so like there's every now and then I'm just like, maybe I shouldn't do any marketing whatsoever.
[00:07:58.720 --> 00:08:04.880] Like all that really matters is relationship management with these like really, really large authors.
[00:08:04.880 --> 00:08:09.760] And like because that is the dominant flywheel, like that's all we need to care about.
[00:08:09.760 --> 00:08:23.440] And of course that's not true because what has happened, I think growth-wise with ButtonDown over the past year is, well, we've sort of hit saturation in a couple niches, in a couple parts of like the super technical space.
[00:08:23.440 --> 00:08:37.280] But to break into like more non-technical niches where we're still a really good and compelling product, that's where we need that other bucket of marketing because we don't have people in those spaces yet to proselytize.
[00:08:37.280 --> 00:08:40.080] But I feel like every cliche about marketing is true.
[00:08:40.080 --> 00:08:42.400] It's just like you're trying a bunch of stuff.
[00:08:42.400 --> 00:08:46.320] Every now and then something works and you're like, okay, let's try that 50 more times.
[00:08:46.320 --> 00:08:50.400] And then, maybe, if you're lucky, it actually does repeat and it wasn't just a fluke.
[00:08:50.400 --> 00:08:54.400] How are you sort of approaching who you are for?
[00:08:54.400 --> 00:09:02.920] And as you get bigger and bigger, and you're saying you've sort of reached terminal velocity in some niches, what is your approach to that at the moment?
[00:09:03.320 --> 00:09:13.000] We have doubled down on being very aggressively for technical users.
[00:09:13.000 --> 00:09:17.160] Like, we had temporarily removed the word Markdown from our splash page.
[00:09:17.160 --> 00:09:24.840] Like, Markdown has always been the canary of like, are we trying to very, very loudly signal that we are for technical people or not?
[00:09:24.840 --> 00:09:35.640] Because if you're a non-technical user and you read Markdown like through the H2 and you don't know what that is, you're like, am I going to need to Google to understand this product?
[00:09:35.640 --> 00:09:43.080] Conversely, if you're a technical user and you see Markdown, even if you don't really care about that as a feature, you instantly know this is a product for me.
[00:09:43.080 --> 00:09:52.120] And I think that kind of niche, because it is like the total addressable market of like that little subset is not like $100 million company status.
[00:09:52.120 --> 00:10:02.840] It's a very strong and solid company, but like, I think that is too narrow in focus for a lot of the larger and more nascent companies to try and push at.
[00:10:02.840 --> 00:10:07.480] And beyond that, what we want to just do is focus on polish.
[00:10:07.480 --> 00:10:10.280] Like, focus on polish, and I'd say focus on service.
[00:10:10.840 --> 00:10:14.200] Our churn is incredibly low.
[00:10:14.200 --> 00:10:31.400] And I say that despite email being this very weird industry where at any day, any point in time, you can export all of your subscribers, all of your archives, move to a new service, and everyone kind of has the same pricing model and same feature base.
[00:10:31.400 --> 00:10:35.080] And the reason people stick around are for three reasons.
[00:10:35.080 --> 00:10:37.160] One is familiarity.
[00:10:37.160 --> 00:10:42.280] People go with the tools that they're already using for something else that they're comfortable in.
[00:10:42.280 --> 00:10:52.320] They go for stability, both in terms of like the API and the interface and also deliverability, because that's the most important thing for emails is actually landing in inboxes.
[00:10:52.320 --> 00:10:54.160] And the third is like customer service, right?
[00:10:54.160 --> 00:11:00.000] We have so many people who explicitly say, yeah, I was thinking about moving to this other provider.
[00:11:00.000 --> 00:11:03.680] And the reason I'm not is because the customer service is really good.
[00:11:03.680 --> 00:11:10.480] I'm actually chatting with a human and not a chat bot or like getting bumped between like three or four different routing things.
[00:11:10.480 --> 00:11:17.680] Like I can email support and I'm getting a response back the same day from the same person who chatted with me like three weeks ago.
[00:11:17.680 --> 00:11:20.800] Your copy on your homepage, is that written by you?
[00:11:20.800 --> 00:11:21.440] It is.
[00:11:21.680 --> 00:11:24.160] That was the first time I got some help.
[00:11:24.160 --> 00:11:37.600] I was working on this with, because this is also the tunnel vision of spending all day and all week and all year, like thinking about emails and newsletters is you forget that words mean different things to different people.
[00:11:37.600 --> 00:11:46.880] But the original prose comes from either me or my design partner who I'm going to shout out, Nick DeSabado.
[00:11:46.880 --> 00:11:48.800] That's nickd.org.
[00:11:49.120 --> 00:11:49.920] It's very cool.
[00:11:49.920 --> 00:11:50.560] I love it.
[00:11:50.880 --> 00:11:59.840] Do you think more people should take this approach to Marx and Zite just having a couple of paragraphs to copy a bit of social proof like you have?
[00:11:59.840 --> 00:12:06.000] I'll put the link for this if people are listening and they want to read through this page we're discussing.
[00:12:06.400 --> 00:12:19.440] One of the things that is probably correct that I've always disregarded is I've never run a single A-B test or a single like quantitative test on Button Down Splash Page.
[00:12:19.440 --> 00:12:31.560] Like, whatever we publish is always based purely on vibes of like, does this seem like a more accurate reflection of who we are, who we're trying to attract, all of those things.
[00:12:31.560 --> 00:12:33.640] And like, that's the only thing that matters.
[00:12:33.960 --> 00:12:43.720] The person who reads like this amount of text above the fold and gets like scared off because they're just like, this is not for me, this doesn't resonate, is not going to be a good button-down user.
[00:12:43.720 --> 00:12:53.480] And conversely, like, the people who read this and they're like, this voice is so different than every other SaaS marketing site that I've ever seen and all those, those people make really, really good customers.
[00:12:53.480 --> 00:13:04.600] And it's better to kind of splinter that really, really early, top in the funnel, as opposed to like having a very, very generic top of funnel that gets a lot of people through the door.
[00:13:04.600 --> 00:13:09.560] But then once they're deeply enmashed, then they're like, oh, this actually wasn't for me at all.
[00:13:09.560 --> 00:13:10.840] I'm going to bounce off.
[00:13:10.840 --> 00:13:12.920] And it's also, I think, just kind of fun.
[00:13:12.920 --> 00:13:31.720] Like, I do not envy the folks who kind of have to like redesign their bento grid every year and like get the I'm always super impressed with all those really cool micro interactions and stuff, but like I'm always suspicious that those things have a meaningful impact on the conversion of the landing page itself.
[00:13:31.720 --> 00:13:39.560] And they're not just effective because they're like a social channel of you can show that as a video and that brings people in through the front door.
[00:13:39.560 --> 00:13:45.960] That's valuable, but that's also like sort of a different value prop than just having really strong pros.
[00:13:46.280 --> 00:13:54.680] And I guess because you run button down yourself, you're free to make decisions like this and no one's telling you.
[00:13:55.000 --> 00:13:57.320] I don't need to ask anyone for extra time off.
[00:13:57.320 --> 00:13:59.880] I don't need to ask anyone for irregular hours.
[00:14:00.040 --> 00:14:13.320] The downside of that, of course, is like, as opposed to being in a larger organization or a place where you have stakeholders or co-founders who can help shoulder the burden, every email I didn't answer in like October because I was getting three hours of sleep a night and all that stuff.
[00:14:13.320 --> 00:14:15.680] Like, there was no one else to really answer that.
[00:14:15.920 --> 00:14:18.160] It would be me the following day.
[00:14:18.160 --> 00:14:34.000] And so, there's always, I think, this interesting balance between having a lot of independence and agency and freedom versus having a lack of safety net or a lack of support system to help you.
[00:14:34.000 --> 00:14:45.120] And what I've always tried to do is like thread that needle of like, let me make sure that if I do drop off the grid for a week or whatever, there's scaffolding and infrastructure in place.
[00:14:45.120 --> 00:14:51.120] But I can still change my website's H1 on the drop of a hat because I feel like it.
[00:14:52.320 --> 00:14:56.080] We do these seasonal H1s that I tank conversion, I'm sure.
[00:14:56.080 --> 00:15:01.200] But I just find them funny: like, change button down to boot and down because it's Halloween.
[00:15:01.200 --> 00:15:05.760] Like, that's why I want to run a company is to do silly things.
[00:15:05.760 --> 00:15:13.120] And to me, like, sacrificing that in pursuit of some other thing sort of feels like I'm missing the whole point.
[00:15:13.120 --> 00:15:14.000] Dude, you're so right.
[00:15:14.000 --> 00:15:17.680] And this is what I love about builders, people like you.
[00:15:17.680 --> 00:15:22.320] You can do what interests you and what's fun and what has personality.
[00:15:22.320 --> 00:15:25.200] And you can bring that because it is just you.
[00:15:25.440 --> 00:15:30.880] But you are still very thoughtful about the decisions you're making with the product.
[00:15:30.880 --> 00:15:33.520] But why not have fun with it at the same time?
[00:15:34.160 --> 00:15:35.920] Now, a few minutes left.
[00:15:35.920 --> 00:15:37.120] What are you watching?
[00:15:37.120 --> 00:15:38.640] What are you reading?
[00:15:38.640 --> 00:15:39.920] What are you listening to?
[00:15:39.920 --> 00:15:42.880] What's your content consumption diet currently?
[00:15:43.200 --> 00:15:51.680] The business or non-fiction book that by far I've loved the most this year is called Becoming Trader Joe.
[00:15:51.680 --> 00:15:58.320] A lot of these business book autobiographies I've found to be like really, really boring and really, really facile.
[00:15:58.320 --> 00:16:04.600] Where it's like, oh, yeah, I had this divine plan from day one and here's every master stroke along the way.
[00:15:59.840 --> 00:16:07.160] And this is like the polar opposite of that.
[00:16:07.720 --> 00:16:08.680] Newsletter?
[00:16:08.920 --> 00:16:14.600] You put me onto Matt Levine's money newsletter and you said it was just beautiful writing.
[00:16:14.600 --> 00:16:16.840] But what else are you reading newsletter wise?
[00:16:16.840 --> 00:16:41.720] I think the next one I'm going to plug is Patio 11 or Patrick McKenzie's Gets in Money, which covers a lot of the same stuff, but I think he has a similar aptitude of like, let me break down these really, really important but deeply technical topics about finance and explain and entertain the reader in a way that I think very few people have been able to do.
[00:16:41.720 --> 00:16:42.200] Cool.
[00:16:42.200 --> 00:16:43.480] Well, I've got to let you go.
[00:16:43.480 --> 00:16:44.520] It's 10 past.
[00:16:44.520 --> 00:16:45.160] Thank you so much.
[00:16:45.480 --> 00:16:48.360] This was a blast to chat again and catch up.
[00:16:48.360 --> 00:16:53.160] I feel like this was less of an interview and more just like hanging out with you again after a couple of years.
[00:16:53.160 --> 00:16:53.640] It was.
[00:16:53.880 --> 00:16:54.600] I really enjoyed it.
[00:16:54.600 --> 00:16:56.120] I can't wait to turn this into an episode.
[00:16:56.120 --> 00:16:57.800] Justin, keep doing amazing stuff.
[00:16:57.800 --> 00:16:59.160] Really appreciate chatting.
[00:16:59.160 --> 00:16:59.560] Of course.
[00:16:59.560 --> 00:17:00.840] Take it easy and chat soon.
[00:17:00.840 --> 00:17:02.840] Thank you for listening to this episode of Indie Bytes.
[00:17:02.840 --> 00:17:08.360] If you enjoyed this conversation and want access to the full hour-long chat Justin and I had, sign up to the Indie Bytes membership.
[00:17:08.360 --> 00:17:09.560] Link is in the show notes.
[00:17:09.560 --> 00:17:12.600] And a thank you to my sponsor, Eman Octopus, for making the show happen.
[00:17:12.600 --> 00:17:13.480] That's all from me.
[00:17:13.480 --> 00:17:14.920] See you next week.

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

[00:00:01.280 --> 00:00:10.080] I feel like if every cliche about marketing is true, it's just like you're trying a bunch of stuff every now and then something works and you're like, okay, let's try that 50 more times.
[00:00:10.080 --> 00:00:13.920] And then maybe if you're lucky, it actually does repeat and it wasn't just a fluke.
[00:00:13.920 --> 00:00:19.120] Hello, and welcome back to Indiebytes, the podcast where I bring you stories of fellow indie hackers in 15 minutes or less.
[00:00:19.120 --> 00:00:24.640] Today I'm joined by Justin Duke, who is the founder of Button Down, a simple email tool he launched in 2017.
[00:00:24.640 --> 00:00:31.280] Justin was last on the podcast two years ago when he just hit 15k MRR and had left his role at Stripe to focus on Button Down full-time.
[00:00:31.280 --> 00:00:34.080] I was struck then by Justin's well-thought-out approach to building.
[00:00:34.080 --> 00:00:40.320] He makes calculated risks and shares a lot of his learnings on his blog, Applied Cartography, which is an essential read for any indie hackers.
[00:00:40.320 --> 00:00:45.680] This episode, I catch up with Justin to hear how he's grown a team to eight people and his approach to building a company he loves.
[00:00:45.680 --> 00:01:00.160] This is a cut-down version of an hour-long catch-up I had with Justin, which I'm going to make available on the Indiebytes membership at indiebytes.com/slash membership, where we discuss his personal blog, how he structures his time as a new parent, and we go deeper into hiring high-agency unicorns.
[00:01:00.160 --> 00:01:03.200] I also want to thank my sponsor EmailOctopus for supporting the show.
[00:01:03.200 --> 00:01:12.240] Now, obviously, Email Octopus are a competitor to the product of today's guests, so I asked Justin if he was okay with it, and his response shows exactly how all founders should approach competitors.
[00:01:12.240 --> 00:01:22.800] Near and dear to my heart, they've been like posting sort of their bootstrap stuff for years, and they have a very rich history of talking about their growth.
[00:01:23.200 --> 00:01:32.800] My philosophy with the email space is always like my biggest competitors are the tools that have been around for 30 years, not 10 years.
[00:01:33.280 --> 00:01:38.160] That's where the truly subpar user experiences are happening right now.
[00:01:38.160 --> 00:01:42.960] So, if you want to give Email Octopus a go, head to emailoctopus.com or hit the link in the show notes.
[00:01:42.960 --> 00:01:46.000] Another quick note: Justin is using a Blue Yeti microphone.
[00:01:46.000 --> 00:01:47.120] You know my thoughts on that.
[00:01:47.120 --> 00:01:49.680] So, I can only apologize for his audio quality.
[00:01:49.680 --> 00:01:52.160] I promise you'll forget about it after a couple of minutes.
[00:01:52.160 --> 00:01:58.240] We kick off this episode talking about how Button Down is going two years after our previous Indiebytes episode.
[00:01:58.960 --> 00:01:59.960] It was so funny.
[00:01:59.680 --> 00:02:04.440] I listened back to the episode we did, what, like almost two years ago.
[00:02:04.760 --> 00:02:10.760] It sounded like I was talking about me and Button Down from like 10 years ago.
[00:02:10.760 --> 00:02:13.400] The business itself doing really, really well.
[00:02:13.400 --> 00:02:18.840] I can no longer really share revenue numbers because we've just kind of grown to the point, but very healthy growth.
[00:02:18.840 --> 00:02:30.280] After leaving Stripe, there was like a clear sort of mission in my head, which was like, I want to just figure out if this is sustainable for me from like an existential point of view, from a financial point of view.
[00:02:30.280 --> 00:02:34.120] Like this feels good to like spend my time working on this full-time.
[00:02:34.120 --> 00:02:37.480] And then once we kind of hit that milestone, I was like, yeah, I like this.
[00:02:37.880 --> 00:02:39.400] This is what my days are.
[00:02:39.400 --> 00:02:41.240] Then it's like, okay, what's next?
[00:02:41.240 --> 00:02:43.960] Because you can always grow a company.
[00:02:43.960 --> 00:02:47.080] Like the default position is to keep trying to grow it.
[00:02:47.080 --> 00:02:50.840] ButtonDown had reached the point where I couldn't just keep doing it myself.
[00:02:50.840 --> 00:02:55.000] Like I know I was having a kid, I had other interests and I didn't want to work 80-hour weeks.
[00:02:55.000 --> 00:02:56.600] So it's like, do you hire a team?
[00:02:56.600 --> 00:03:02.280] And then if you hire a team, you're shifting back into management when really what I like doing is engineering.
[00:03:02.280 --> 00:03:35.560] And a lot of the past year for me has kind of been navigating that maze of figuring out a way to keep having it be a business that I legitimately enjoy spending all of my time thinking about and getting my hands dirty in, while also still like making sure it grows, making sure the new folks on the team aren't thrown off into the deep end, making sure new customers are still having a great experience and kind of like hitting that next level beyond just, okay, this is not quite an escape velocity, but the fight to survive, that part is done.
[00:03:35.560 --> 00:03:38.600] Like, button Down is a healthy and thriving business.
[00:03:38.600 --> 00:03:40.920] Now, what are the next sets of goals?
[00:03:40.920 --> 00:03:45.040] You're absolutely right because I speak to founders that fall into this trap.
[00:03:45.040 --> 00:03:49.760] There was one chap I met the other day who'd like grown his business to 30 cameras.
[00:03:44.840 --> 00:03:50.560] That's very healthy.
[00:03:50.800 --> 00:03:54.640] And he was just like, Am I just like chasing growth now?
[00:03:54.960 --> 00:03:55.520] Is this it?
[00:03:55.520 --> 00:03:56.960] He was just, he was bored.
[00:03:56.960 --> 00:03:58.720] He was like, what's next?
[00:03:58.720 --> 00:04:11.040] And you've got so many of these indie people that like just getting something off the ground, getting it to a few K MRR, and then don't like once they're now in the business to actually keep working on it and like keep motivation going.
[00:04:11.040 --> 00:04:19.680] Or you've got other people who do like the fact they've built themselves a job where they have pretty much full control over what they do and they're very passionate about it.
[00:04:19.680 --> 00:04:23.840] So I'm guessing you've put a lot of thought into making sure it's in the latter camp.
[00:04:23.840 --> 00:04:38.880] Yeah, one of the things that has been sort of like priority number one is, and I've run into this phrase a lot, but like I really wanted to avoid making myself a job that I hated.
[00:04:38.880 --> 00:04:43.200] And like, I think it's very obvious to me how that would happen.
[00:04:43.200 --> 00:04:58.960] Of like, if I just carve out all the things that I really love, which is like doing engineering work, doing like interesting product exploration, talking to customers and users, and I say, these are no longer worth my time because they're low leverage.
[00:04:58.960 --> 00:05:03.120] I'm going to hire those positions out and I'm going to manage those people instead.
[00:05:03.120 --> 00:05:12.000] And what I'm left with is all the stuff like quote-unquote a CEO is supposed to do, but also not what I'm particularly passionate about or frankly, even good at.
[00:05:12.000 --> 00:05:17.600] And figuring out a way to balance those two things has been really, really key, especially the past like six months.
[00:05:17.920 --> 00:05:19.680] So, how big's a team?
[00:05:19.680 --> 00:05:20.680] How's growth?
[00:05:20.680 --> 00:05:23.760] And what are you spending your time on day to day-to-day?
[00:05:23.760 --> 00:05:33.880] Yeah, so we're around eight folks total, and that's a mix of mostly contractors, a couple W-2s, myself included.
[00:05:34.200 --> 00:05:45.240] And what my day-to-day looks like is less around like line-level management of, okay, it's time for everyone to open linear and we're going to like carve out the tasks and do all that.
[00:05:45.240 --> 00:06:00.360] Like, I've been very particular about wanting to work with folks who feel really comfortable with ambiguity and sort of getting their hands dirty and doing things that might not necessarily be the case at larger companies.
[00:06:00.360 --> 00:06:17.240] And so, like, the example I always give is most large companies, even really, really good ones, design like the IC engineer role such that the median IC engineer doesn't have to like do design or talk with customers or look at a support inbox or any of those things.
[00:06:17.240 --> 00:06:41.480] And my philosophy has sort of been the opposite: I feel very strongly that that's where the best product work comes from is being able to context switch from a, this customer wrote in asking about this thing, and they think it's a bug, but actually, what this is, is like a better UX waiting to happen, and I can connect those dots because I'm like looking at all of these things.
[00:06:41.480 --> 00:06:58.920] And so, finding and working with folks who are really, really good at that level of thinking, as opposed to like a you can imagine an abstract like contract engineer who's just like, give me a bunch of tickets and I'm gonna knock them out, and like that is my relationship with this business.
[00:06:58.920 --> 00:07:07.640] And that to me has been really, really rewarding because it's also it removes some of the things that I didn't love about engineering management, which was the administrivia.
[00:07:07.640 --> 00:07:16.880] Instead, a lot of the engineering conversations I get to have are closer to like design or architectural conversations, which feels much more interesting and rewarding to me.
[00:07:16.880 --> 00:07:18.560] Any marketing highs?
[00:07:18.560 --> 00:07:19.440] Not yet.
[00:07:19.440 --> 00:07:22.960] That's probably going to change at some point.
[00:07:22.960 --> 00:07:40.640] The thing that has always been like a good problem and a bad problem with Button Down's growth is like we have all of the conventional SaaS playbook things of like you do referrals and you mess with AdWords and you've got programmatic SEO and all of these things.
[00:07:40.640 --> 00:07:42.400] And they're all like fine.
[00:07:42.400 --> 00:07:50.720] And then someone who has a massive following starts to use ButtonDown and like broadcasts to their subscribers, hey, we're using ButtonDown now.
[00:07:50.720 --> 00:07:53.520] And like that just dwarfs everything else.
[00:07:53.520 --> 00:07:58.720] And so like there's every now and then I'm just like, maybe I shouldn't do any marketing whatsoever.
[00:07:58.720 --> 00:08:04.880] Like all that really matters is relationship management with these like really, really large authors.
[00:08:04.880 --> 00:08:09.760] And like because that is the dominant flywheel, like that's all we need to care about.
[00:08:09.760 --> 00:08:23.440] And of course that's not true because what has happened, I think growth-wise with ButtonDown over the past year is, well, we've sort of hit saturation in a couple niches, in a couple parts of like the super technical space.
[00:08:23.440 --> 00:08:37.280] But to break into like more non-technical niches where we're still a really good and compelling product, that's where we need that other bucket of marketing because we don't have people in those spaces yet to proselytize.
[00:08:37.280 --> 00:08:40.080] But I feel like every cliche about marketing is true.
[00:08:40.080 --> 00:08:42.400] It's just like you're trying a bunch of stuff.
[00:08:42.400 --> 00:08:46.320] Every now and then something works and you're like, okay, let's try that 50 more times.
[00:08:46.320 --> 00:08:50.400] And then, maybe, if you're lucky, it actually does repeat and it wasn't just a fluke.
[00:08:50.400 --> 00:08:54.400] How are you sort of approaching who you are for?
[00:08:54.400 --> 00:09:02.920] And as you get bigger and bigger, and you're saying you've sort of reached terminal velocity in some niches, what is your approach to that at the moment?
[00:09:03.320 --> 00:09:13.000] We have doubled down on being very aggressively for technical users.
[00:09:13.000 --> 00:09:17.160] Like, we had temporarily removed the word Markdown from our splash page.
[00:09:17.160 --> 00:09:24.840] Like, Markdown has always been the canary of like, are we trying to very, very loudly signal that we are for technical people or not?
[00:09:24.840 --> 00:09:35.640] Because if you're a non-technical user and you read Markdown like through the H2 and you don't know what that is, you're like, am I going to need to Google to understand this product?
[00:09:35.640 --> 00:09:43.080] Conversely, if you're a technical user and you see Markdown, even if you don't really care about that as a feature, you instantly know this is a product for me.
[00:09:43.080 --> 00:09:52.120] And I think that kind of niche, because it is like the total addressable market of like that little subset is not like $100 million company status.
[00:09:52.120 --> 00:10:02.840] It's a very strong and solid company, but like, I think that is too narrow in focus for a lot of the larger and more nascent companies to try and push at.
[00:10:02.840 --> 00:10:07.480] And beyond that, what we want to just do is focus on polish.
[00:10:07.480 --> 00:10:10.280] Like, focus on polish, and I'd say focus on service.
[00:10:10.840 --> 00:10:14.200] Our churn is incredibly low.
[00:10:14.200 --> 00:10:31.400] And I say that despite email being this very weird industry where at any day, any point in time, you can export all of your subscribers, all of your archives, move to a new service, and everyone kind of has the same pricing model and same feature base.
[00:10:31.400 --> 00:10:35.080] And the reason people stick around are for three reasons.
[00:10:35.080 --> 00:10:37.160] One is familiarity.
[00:10:37.160 --> 00:10:42.280] People go with the tools that they're already using for something else that they're comfortable in.
[00:10:42.280 --> 00:10:52.320] They go for stability, both in terms of like the API and the interface and also deliverability, because that's the most important thing for emails is actually landing in inboxes.
[00:10:52.320 --> 00:10:54.160] And the third is like customer service, right?
[00:10:54.160 --> 00:11:00.000] We have so many people who explicitly say, yeah, I was thinking about moving to this other provider.
[00:11:00.000 --> 00:11:03.680] And the reason I'm not is because the customer service is really good.
[00:11:03.680 --> 00:11:10.480] I'm actually chatting with a human and not a chat bot or like getting bumped between like three or four different routing things.
[00:11:10.480 --> 00:11:17.680] Like I can email support and I'm getting a response back the same day from the same person who chatted with me like three weeks ago.
[00:11:17.680 --> 00:11:20.800] Your copy on your homepage, is that written by you?
[00:11:20.800 --> 00:11:21.440] It is.
[00:11:21.680 --> 00:11:24.160] That was the first time I got some help.
[00:11:24.160 --> 00:11:37.600] I was working on this with, because this is also the tunnel vision of spending all day and all week and all year, like thinking about emails and newsletters is you forget that words mean different things to different people.
[00:11:37.600 --> 00:11:46.880] But the original prose comes from either me or my design partner who I'm going to shout out, Nick DeSabado.
[00:11:46.880 --> 00:11:48.800] That's nickd.org.
[00:11:49.120 --> 00:11:49.920] It's very cool.
[00:11:49.920 --> 00:11:50.560] I love it.
[00:11:50.880 --> 00:11:59.840] Do you think more people should take this approach to Marx and Zite just having a couple of paragraphs to copy a bit of social proof like you have?
[00:11:59.840 --> 00:12:06.000] I'll put the link for this if people are listening and they want to read through this page we're discussing.
[00:12:06.400 --> 00:12:19.440] One of the things that is probably correct that I've always disregarded is I've never run a single A-B test or a single like quantitative test on Button Down Splash Page.
[00:12:19.440 --> 00:12:31.560] Like, whatever we publish is always based purely on vibes of like, does this seem like a more accurate reflection of who we are, who we're trying to attract, all of those things.
[00:12:31.560 --> 00:12:33.640] And like, that's the only thing that matters.
[00:12:33.960 --> 00:12:43.720] The person who reads like this amount of text above the fold and gets like scared off because they're just like, this is not for me, this doesn't resonate, is not going to be a good button-down user.
[00:12:43.720 --> 00:12:53.480] And conversely, like, the people who read this and they're like, this voice is so different than every other SaaS marketing site that I've ever seen and all those, those people make really, really good customers.
[00:12:53.480 --> 00:13:04.600] And it's better to kind of splinter that really, really early, top in the funnel, as opposed to like having a very, very generic top of funnel that gets a lot of people through the door.
[00:13:04.600 --> 00:13:09.560] But then once they're deeply enmashed, then they're like, oh, this actually wasn't for me at all.
[00:13:09.560 --> 00:13:10.840] I'm going to bounce off.
[00:13:10.840 --> 00:13:12.920] And it's also, I think, just kind of fun.
[00:13:12.920 --> 00:13:31.720] Like, I do not envy the folks who kind of have to like redesign their bento grid every year and like get the I'm always super impressed with all those really cool micro interactions and stuff, but like I'm always suspicious that those things have a meaningful impact on the conversion of the landing page itself.
[00:13:31.720 --> 00:13:39.560] And they're not just effective because they're like a social channel of you can show that as a video and that brings people in through the front door.
[00:13:39.560 --> 00:13:45.960] That's valuable, but that's also like sort of a different value prop than just having really strong pros.
[00:13:46.280 --> 00:13:54.680] And I guess because you run button down yourself, you're free to make decisions like this and no one's telling you.
[00:13:55.000 --> 00:13:57.320] I don't need to ask anyone for extra time off.
[00:13:57.320 --> 00:13:59.880] I don't need to ask anyone for irregular hours.
[00:14:00.040 --> 00:14:13.320] The downside of that, of course, is like, as opposed to being in a larger organization or a place where you have stakeholders or co-founders who can help shoulder the burden, every email I didn't answer in like October because I was getting three hours of sleep a night and all that stuff.
[00:14:13.320 --> 00:14:15.680] Like, there was no one else to really answer that.
[00:14:15.920 --> 00:14:18.160] It would be me the following day.
[00:14:18.160 --> 00:14:34.000] And so, there's always, I think, this interesting balance between having a lot of independence and agency and freedom versus having a lack of safety net or a lack of support system to help you.
[00:14:34.000 --> 00:14:45.120] And what I've always tried to do is like thread that needle of like, let me make sure that if I do drop off the grid for a week or whatever, there's scaffolding and infrastructure in place.
[00:14:45.120 --> 00:14:51.120] But I can still change my website's H1 on the drop of a hat because I feel like it.
[00:14:52.320 --> 00:14:56.080] We do these seasonal H1s that I tank conversion, I'm sure.
[00:14:56.080 --> 00:15:01.200] But I just find them funny: like, change button down to boot and down because it's Halloween.
[00:15:01.200 --> 00:15:05.760] Like, that's why I want to run a company is to do silly things.
[00:15:05.760 --> 00:15:13.120] And to me, like, sacrificing that in pursuit of some other thing sort of feels like I'm missing the whole point.
[00:15:13.120 --> 00:15:14.000] Dude, you're so right.
[00:15:14.000 --> 00:15:17.680] And this is what I love about builders, people like you.
[00:15:17.680 --> 00:15:22.320] You can do what interests you and what's fun and what has personality.
[00:15:22.320 --> 00:15:25.200] And you can bring that because it is just you.
[00:15:25.440 --> 00:15:30.880] But you are still very thoughtful about the decisions you're making with the product.
[00:15:30.880 --> 00:15:33.520] But why not have fun with it at the same time?
[00:15:34.160 --> 00:15:35.920] Now, a few minutes left.
[00:15:35.920 --> 00:15:37.120] What are you watching?
[00:15:37.120 --> 00:15:38.640] What are you reading?
[00:15:38.640 --> 00:15:39.920] What are you listening to?
[00:15:39.920 --> 00:15:42.880] What's your content consumption diet currently?
[00:15:43.200 --> 00:15:51.680] The business or non-fiction book that by far I've loved the most this year is called Becoming Trader Joe.
[00:15:51.680 --> 00:15:58.320] A lot of these business book autobiographies I've found to be like really, really boring and really, really facile.
[00:15:58.320 --> 00:16:04.600] Where it's like, oh, yeah, I had this divine plan from day one and here's every master stroke along the way.
[00:15:59.840 --> 00:16:07.160] And this is like the polar opposite of that.
[00:16:07.720 --> 00:16:08.680] Newsletter?
[00:16:08.920 --> 00:16:14.600] You put me onto Matt Levine's money newsletter and you said it was just beautiful writing.
[00:16:14.600 --> 00:16:16.840] But what else are you reading newsletter wise?
[00:16:16.840 --> 00:16:41.720] I think the next one I'm going to plug is Patio 11 or Patrick McKenzie's Gets in Money, which covers a lot of the same stuff, but I think he has a similar aptitude of like, let me break down these really, really important but deeply technical topics about finance and explain and entertain the reader in a way that I think very few people have been able to do.
[00:16:41.720 --> 00:16:42.200] Cool.
[00:16:42.200 --> 00:16:43.480] Well, I've got to let you go.
[00:16:43.480 --> 00:16:44.520] It's 10 past.
[00:16:44.520 --> 00:16:45.160] Thank you so much.
[00:16:45.480 --> 00:16:48.360] This was a blast to chat again and catch up.
[00:16:48.360 --> 00:16:53.160] I feel like this was less of an interview and more just like hanging out with you again after a couple of years.
[00:16:53.160 --> 00:16:53.640] It was.
[00:16:53.880 --> 00:16:54.600] I really enjoyed it.
[00:16:54.600 --> 00:16:56.120] I can't wait to turn this into an episode.
[00:16:56.120 --> 00:16:57.800] Justin, keep doing amazing stuff.
[00:16:57.800 --> 00:16:59.160] Really appreciate chatting.
[00:16:59.160 --> 00:16:59.560] Of course.
[00:16:59.560 --> 00:17:00.840] Take it easy and chat soon.
[00:17:00.840 --> 00:17:02.840] Thank you for listening to this episode of Indie Bytes.
[00:17:02.840 --> 00:17:08.360] If you enjoyed this conversation and want access to the full hour-long chat Justin and I had, sign up to the Indie Bytes membership.
[00:17:08.360 --> 00:17:09.560] Link is in the show notes.
[00:17:09.560 --> 00:17:12.600] And a thank you to my sponsor, Eman Octopus, for making the show happen.
[00:17:12.600 --> 00:17:13.480] That's all from me.
[00:17:13.480 --> 00:17:14.920] See you next week.

How Justin Duke is building Buttondown into the perfect bootstrapped business

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