David speaks with Rob Fitzpatrick,  a well-storied entrepreneur, and writer. Author of three books, including The Mom Test and Write Useful Books, both of which are among the most universally recommended books for early founders and non-fiction writers.

We talked about his journey getting into YC in 2007, trying to build this business, pivoting mid-interview, and building a business that ultimately failed. He also talks about how he rose from the ashes and tried a bunch of different things.

And eventually built an agency that was making about a million dollars a year, and then the journey to the place where he is now, where he is taking a much slower and more deliberate approach, both to building businesses and also to writing.

🎙 Listen in your favourite podcast player

📹 Watch on Youtube

👤 Connect with Rob Fitzpatrick:

Twitter: @robfitz | https://twitter.com/robfitz

Books: The Mom Test | https://amzn.to/3UeADcN ;

Write Useful Books | https://amzn.to/3Vp1HYj

Website: https://www.robfitz.com/home

YouTube: https://www.youtube.com/c/RobFitzpatrick

📄 Show notes:

2:45 | Getting into Y Combinator in 2007

4: 28 | An introduction to entrepreneurship

7:14 | Lessons from failure

11:48 | The classic mistake founders make

15:05 | Freelance programming

18: 19 | Kickstarting a board game

19: 22 | Writing The Mom Test

20: 20 | How to get traction with book sales

23: 09 | How he wrote his first book

24: 48 | Dealing with the Sunk Cost Fallacy

30:20 | Deciding what feedback to accept

33:54 | The metal detector test

35:31 | Dealing with ADHD

36:18 | Force yourself to talk to people

37:19 | The great lie of Lean Startup

38:32 | Building a lifestyle for yourself

42:55 | Managing your time and energy

45:58 | The secret to great sleep

47:23 | The future of the creator economy

49:51 | Lessons from Leonarda DaVinci

52:18 | If you produce good things, people will find it

54:37 | Make things that become more famous than you

57:30 | How to build a career

🗣 Mentioned in the show:

Hacker News | https://news.ycombinator.com/

Y Combinator | https://www.ycombinator.com/

Seed Camp Week | https://seedcamp.com/

Sunk Cost Fallacy | https://www.theknowledge.io/sunk-cost-fallacy/

usefulbooks.com | http://usefulbooks.com/

Annie Duke | https://www.annieduke.com/

Thinking in Bets | https://amzn.to/3VlU196

Angela Duckworth | https://angeladuckworth.com/

Grit | https://amzn.to/3Vzu3iR

Workshop Survival Guide | https://www.workshopsurvival.com/

Alice Bentinck | https://twitter.com/alicebentinck

Why we use Edge to generate ideas | https://medium.com/entrepreneur-first/why-we-use-edge-c08fe37adf1

Web 3.0 | https://www.investopedia.com/web-20-web-30-5208698

Leonarda DaVinci | https://www.britannica.com/biography/Leonardo-da-Vinci

Enlightenment | https://www.britannica.com/event/Enlightenment-European-history

David Kadavy | https://kadavy.net/

Brennan Dunn | https://twitter.com/brennandunn

Full episode transcript below

👨🏾‍💻 About David Elikwu:

David Elikwu FRSA is a serial entrepreneur, strategist and writer. David is the founder of The Knowledge, a platform helping people think deeper and work smarter.

🚀 Career Hyperdrive

Career Hyperdrive is a live, cohort-based course that helps people find their competitive advantage, gain clarity around their goals and build a future-proof set of mental frameworks so they can live an extraordinary life doing work they love.

During this course, you will make the leap from 'going with the flow' to actively crafting your journey. And you’ll join a community of ambitious peers who will hold you accountable for betting on yourself.


🧭 The Knowledge

On The Knowledge Podcast you’ll hear from the best and brightest minds in business, entrepreneurship, and beyond. Hosted by writer and entrepreneur David Elikwu, each episode features in-depth interviews with makers, thinkers, and innovators from a variety of backgrounds.

The Knowledge is a weekly newsletter for people who want to get more out of life. It's full of insights from psychology, philosophy, productivity and business, all designed to help you think deeper and work smarter.

Website: theknowledge.io

Podcast: plnk.to/theknowledge

📜Full transcript:

Rob Fitzpatrick: [00:00:00] I will tell you my career strategy is to find something I'm interested in. Figure it out, build some products in the space, get to know other smart people in the space, learn a lot from them, and then eventually consolidate that into a book and move on to the next interesting thing, and, I don't know, 3, 4, 5 years per topic. Get a book at the end, move on to something new. It's pretty fun.

David Elikwu: Hey, I'm David Elikwu. And this is The Knowledge. A podcast for anyone looking to think deeper and work smarter. In every episode I speak with makers, thinkers, and innovators to help you get more out of life.

This week I'm speaking with Rob Fitzpatrick. He's an incredibly well storied entrepreneur and writer as the author of three books, including The Mom Test and Write Useful Books, both of which are among the most universally recommended books that I've come across.

And the testament to that is the number of books that he's been able to sell year after year after [00:01:00] a year, completely through referral and word of mouth. So he's both an incredibly prolific writer, but also he is an entrepreneur and he's a builder, and you're gonna hear him talking about getting into YC in 2007 and trying to build this business, pivoting mid-interview, building a business that ultimately failed.

But then he talks about how he rose from the ashes and he tried a bunch of different things. He eventually built an agency that was making about a million dollars a year, and then getting to the place where he is now, where he is taking a much slower and more deliberate approach, both to building businesses and also to writing. So Rob has a ton to share. I'm sure you're gonna love this episode.

You can find Rob on Twitter @robfitz and a quick note for anyone listening to this right now, you can find this podcast wherever you enjoy consuming content.

You can listen to it on your favorite podcast player. You can watch this on YouTube. You can find clips on, [00:02:00] YouTube shorts, Twitter, TikTok, Instagram, wherever you are, you can probably find this podcast. So feel free to consume it in the way that is most comfortable for you.

If you do, please don't forget to share it with a friend and leave a review wherever you listen to podcasts, because it helps us tremendously to reach other people just like you.

So without any further ado, this is Rob Fitzpatrick.

So I'd probably start from you were in YC in 2007 and I think to this day that is still one of the hallmarks of something you are building something great. If you get into YC, you're gonna be the next big thing. It's still something that is highly coveted and really exclusive, really hard to get into. And I'm sure it was equally the same back then.

Rob Fitzpatrick: Well, First off, like when we went through in 2007, it was a very different program than it is now. It was smaller batches, it was less well known. We took it because it was the only option for kind of super early stage teams, whereas now it's this prestigious elite thing. Still knew it wasn't easy to get into, [00:03:00] but it didn't seem like quite the impossible mountain that it is now. And we actually threw away our idea and pivoted mid-interview and they ended up funding us on an idea that we came up with during the interview with PG's help. And we'd been working for a year and a half or two years, but he was like, this will never work. It'll never scale. It's ridiculous. To be fair, I think it would've been a really good kind of bootstrap agency business, the creative agency, which would've been a pretty good fit for the team we had at the time. But, we were really enamored by the idea of the investors. And truthfully, we were so new, we didn't know how to build a business on our own. So we really wanted the roadmap that we felt investors could provide. Instead of just wandering around the wilderness, like hoping to find some nutrition, we're like, all right, they're at least showing us a path and it was both a good and a bad thing. It was good cause it got us in the game and it was really fun. And we all fell in love with business and most of that team has continued doing businesses since then. It was bad because by shifting our idea to fit what investors wanted, we pulled it pretty far away from what we wanted and we ended up feeling, or at least me, I felt stuck for the next three or four years, working really hard to build a business that I [00:04:00] didn't necessarily love. And then we failed anyway. I think maybe if I'd gotten rich off that one, I would've been like it was all worth it, but since we failed, I was like, what did I just throw away the last three years on? And this is ridiculous. I should have done the fun thing with my buddies.

David Elikwu: I think you touched on something that a lot of founders find where when you start a venture backed business, when you go into a business and you have investors and you're not bootstrapping, it's a completely different beast that you're dealing with. And I'm really interested, maybe going back a step, what was your first introduction to, whether it's the word entrepreneurship or this idea of building something for yourself? Cause I think that's not something that everyone thinks that this is for me, this is something I can do.

Rob Fitzpatrick: It was kind a happy accident. I was in university, I went to Georgia Tech in Atlanta and I was studying first computer programming, and then I switched into more like video game design. They called it computational media, but it was cool. It was like a liberal arts spin on. Anyway, I went into it for the game design, and we were trying to make like serious games, so games that would teach like educational lessons or would [00:05:00] be, like a bit more thoughtful rather than just of fun and blowing things up. And we took a spin on that and that's what we pitched to YC. But the reason we took that leap is because I'd enrolled in a course that I didn't really know what it was about, but I really liked the professor and I think it was called something like Project Proposal. And I thought I was at the time on the academic path, I was starting my master's and I wanted to get a PhD and I wanted to become a professor. Because I figured for the type of games and game research that I was interested in, there are no jobs. No jobs. Cause you were specifically not making games to be fun. You were making games often to be non fun, to make a point. And so like clearly there's no market for that. So I thought that project proposal was about applying for kind of academic grants and academic funding. the way the professor took it was actually more about applying for external funding for commercial funding for venture capital. And it took me all semester to like wrap my head around this concept and I kept making these class proposals where I was like, yeah, and we're gonna, we're gonna ask for $350 cuz that's what we need to get the software we need. [00:06:00] And he's like, no, no, no, you need to pay yourself. I was like, I don't need to pay myself. And he's like, you should ask for more money. I'm like, anyway, I finally got it.

And that made me curious cuz about the same time, the reason I got into academia is that I thought it would be a pure battleground of the minds. I was like, yeah, I'm gonna be free from all the corporate bs. The best idea wins. There's no bureaucracy in academia and as I started being friends with professors and PhD candidates, I was like, oh, I made a huge mistake. And so that kind of disillusionment with the purity of the academic system, coincided with this discovery of venture capital and startup funding. And I was like, oh. And so I took what I was doing as my kind of postgraduate research and tried to fit it into a box that I thought would be appealing to investors. And because I was reading Hacker News, I was like, oh YC was the only investor I knew about that would take applications from random internet strangers. So, you know, we did it. And I got one of my, I got my favorite teacher to like quit. He was like the head teaching assistant. I got him to quit and join the company. One of my other buddies dropped out [00:07:00] of university. He was like an artist, like another guy graduated first and then joined. And we had this cool like artsy designing team. And then we're like, okay, investors teach us about business.

David Elikwu: And so you pivoted it ended up not working out. Could you share maybe more details on if there was a specific reason it didn't work out and maybe some of the lessons that you learned along the way?

Rob Fitzpatrick: Yeah. There's a bunch of reasons. When you look at these startup postmortems, it's funny cuz like the business fails and you're like, you wanna write a postmortem? You wanna understand and share the failure, right. Move the community forward. And what I've noticed is that like you don't have the counterfactual. So we, you tend to look at whatever you did and just assume that doing the opposite would've worked or you latch onto some easy solution. So everyone's like, oh, if we just built a better mvp, it would've all been perfect. If we'd just don't cuss the, it would've been all perfect if we'd been marketing driven instead of sales driven, or vice versa. And so you grasp for these kind of easy answers. And I did that at first. I was like, oh, we made this wrong industry choice, or we did this when we should have done this or whatever.

I think actually what I attribute now, the root [00:08:00] cause of the failure for is that we ended up pivoting toward a business model that looked really good on paper. And the reason we did this, it like looked good in a vacuum. It looks good on a spreadsheet. But an idea is only good in so far as your team is able and excited to execute on it. And so we chose these industries we were selling to, like the entertainment industry. We're selling to music studios, music labels, movie studios like the bbc, like television companies. It is really hard to break into those networks. We did it eventually. We got Sony pictures, we got mtv, we got the, we got all these big brands as customers, but it took me like a year to build the credibility, to understand the language, to meet the people to learn those skills, to understand their way of operating their language.

And that's like a year of traction that you've given up. That's a year of progress you've given up. And like we had to learn sales, we had to learn enterprise, like supporting enterprise customers. We had to learn all these things. And you can do it, like [00:09:00] you can learn anything if you're excited enough to do it.

But we'd also chosen things. We were like, we didn't really care. All we cared about was the success, right? We didn't have intrinsic, we pivoted away from our intrinsic motivations in the idea. And when you do that, like all you've got left is extrinsic motivations, which is like success. It's traction.

So when we were getting all the press coverage and the investors loved us, it was really fun. We're like, yeah, we're doing it. We're winning. We're being business people. And then once that stuff dried up we raised our seed round just as the 2008 financial crisis was happening. And we like signed the term sheet, but the money hadn't hit our bank account.

And as everyone knows, the deal's not done until the money's in your bank account. And so after the global financial crisis my investors called me, we just used the last of our money to get one way tickets out to London, cuz the investors were in London. There's a big like advertising media scene in London, better for us than san Francisco, just cuz our customers were there. So we raised from London investors and we flew, used the last of our cash. We flew out. We didn't even have money for plane tickets back home, right? And the investors call [00:10:00] me, they go, Rob, your business today is worth half of what it was worth yesterday. If this deal came to us today, we would never in a million years even consider accepting it.

Then like the longest pause of my life, I'm like, how do I even get my, I'm thinking, how do I get my team home? Like we're stuck in a foreign country like, where we don't have residents or the ability to work. And longest pause of my life. And then he goes, but we've never gone back on a handshake, so let's get the money to you tonight before things get any worse. I was like, Yes. And I ended up having to bribe this cafe owner to stay open till one in the morning, cuz I was faxing like paperwork back and forth with lawyers in San Francisco. Anyway, it was a whole mess.

We were very like driven by these gatekeepers. And it's like when this stuff was happening, when the gatekeepers were saying yeah. It was very fun and we could keep going what is that dried up after the financial crisis, it was like, why are we doing this? But now we're stuck. We've signed these big multi-year contracts with big customers that we worked for months to convince to pay us. We can't stop now. We've got employees, like people have quit their jobs to work on this company. So I was like, oh, why did I do this to myself? It was like the entrepreneur's version of golden handcuffs. It's like you build your [00:11:00] own like golden prison. And I was honestly happy when we failed because I did everything I could to keep it alive and I would've continued for years if we'd had a chance. But I was so burned out and I just wanted to do something fun again. And since then I've been bootstrapping and working on fun projects for customers I like with people I like working with.

So that was a really, like important failure for me.

David Elikwu: Yeah. That makes a lot of sense. I'm interested in moving to bootstrapping and also I think you're working on a lot of like smaller projects in terms of, I guess part of it is the nature of bootstrapping and part of it is maybe you're just working on things. Either you can do yourself or you can do with a small group of people.

I'm interested in what you had to, learn or unlearn in that transition and how different that is to trying to run and operate a company that's designed to scale.

Rob Fitzpatrick: So after the first one failed, I'd made a classic error that a lot of founders do where I let the company's failure destroy my personal finances as well, because I didn't want to admit that we were failing. So I kept using [00:12:00] my own savings to basically cover payroll. I feel like, oh, one more month.

One more month, we can, it's all gonna turn around. But if you think about that it's not gonna turn around in a month, right? And at a certain point you need to draw the line and I should have drawn the line when I still had my savings, not after I'd actually gone broke.

So yeah, I bought us like three more stressful months, but what good is that? Just cause I didn't wanna admit failure. And so that meant that I was broke, right? So I was like, okay, first, and I was burned out. I was like, first priority, I need free time to get outta burnout and I need money to like get a place to sleep. And so I looked for a business that I could basically like get started with the money in my pocket. I had like the deposit from my apartment that had been given back to me. So I had like a little bit of money in my pocket from that deposit, but nowhere to sleep.

And I found this old warehouse that was scheduled to be demolished. It was dirt cheap. And I was like, okay, I'm gonna get this warehouse and I'm gonna set it up as London's cheapest startup co-working space. There was like exposed electrical wiring, there was like water falling from the ceiling, so we could only, we had to [00:13:00] strategically place the desks so that the water wouldn't land on computers, but it was London's cheapest startup co-working space. And, you know, we got a handful of companies in there, and I would go to all the startup events and in London, the pubs were closing at 10:00 PM something like that.

So right as people were like getting hungry and starting to get in the mood to party. So I would go to these startup meetups like five nights a week and just before closing time, and at closing time, I'd be like, hey, the party continues at my co-working space. And so I'd get this whole gang of 30 people, the whole like co-working or the startup meetup would come with me and they'd get into this weird derelict like warehouse that was, should have been demolished years ago.

And they're like What is this place? I'm like, you wanna rent a desk? It's super cheap. And what that meant is I had to be physically present all day, right? To in case something went wrong, but I was mentally free and it was a very like, cash flow positive business. So I did that for about a year and I lived in it. I had a corner in the back where I slept . And then I would wake up early and I would like put my stuff away before the first tendon showed up. I didn't have like a [00:14:00] shower, so for a while I was showering from a plastic bottle that I hung from the ceiling that I drilled holes in. And I would fill it up with a kettle. So I would have hot water and I'd have one to soap up and another wash off. Then I joined a boxing gym, which was a way better idea cuz that a 50 quid a month or whatever was worth it. And I got to shower there each day and so I did that for about a year.

It was fine, right? Cause I got to think, I got to process what had happened in the first business. I got to play with ideas in a very safe environment. I did a bunch of just like dumb throwaway projects, where I spent a week or two weeks just build a product, try to launch it, see what happened, try to do customer support. I tried to make viral products. I tried to make like little productized servicey things. I just tried a bunch of stuff. I was really in like a let's try things mode, right? I didn't want to lose another four years to one big idea. And at the end of that year I was like, okay, that was fun. I enjoyed having my time, but it also be nice to have like pocket money cuz that place just barely broke even.

It was enough to like, keep me like simple food. But that was it. So I was like, okay, let's take what I've learned from the first business and this year of like experimental [00:15:00] products and let's put myself out as a freelancer. And that was really helpful to learn how to be a freelancer. I did freelance programming. I did a little bit of like startup strategy, like helping other entrepreneurs build their pitch decks. And build their story to raise funding. Cuz we were good at figuring out what gatekeepers wanted to hear. That was like the thing we were best at in the first business. And I did that for a while and I was like, okay, I can make money doing this, but I don't really love it. It's like, instead of being, instead of trying to figure out what investors and big enterprise customers want, I'm trying to figure out what these smaller clients want, but it's still not what I want. But I saved up a little bit of money. It was fun. And then I met up with another fellow he had a similar background or set of experiences to me.

This was a little bit of a twist where he'd had a successful business in Canada, had a falling out with the co-founder moved to the UK and tried to replicate the same business in the UK. It was for the hotel industry, but there were meaningful enough differences in the hotel industry between Canada and the UK that he was like, yeah, I've already validated this. I know it [00:16:00] works. And he tried to build the same thing again that completely failed. So we were both kind of burned by these recent failures and we're like, okay, let's set up, we'd both done freelancing. We're like, let's set up a little agency business together. So we set up like an events, an education kind of agency thing, and it went pretty well.

We were like, let's not make the same mistakes. So we were like, we're only gonna do this if we can get a bunch of pre-orders. So we went around, we're basically like our first week, we barely knew each other. We're like, yeah, let's just go hit the streets. And we started walking around to what we thought would be our clients and we ended up getting 50,000 pounds in kind of handshake deals in that first week where people were like, yeah, if you put this together, we'll hire you for this many days at this rate. And we're like, okay, cool.

So we got that 50K. Like in theory it wasn't in our bank account, but it was, you know, a handshake deal. We're like, it's something, right? It shows we're not completely nuts. And over the next two or three years, we built that up to about a million quid a year. And then there was a big, we added a couple more partners, we add some employees. We were traveling all over Europe doing all sorts of fun events and workshops. Fun little agency business, but we just could not find a way to [00:17:00] productize. And eventually, something that I learned also with that business is we were really careful at the beginning to understand what all of the partners and founders wanted, like how the business would integrate with our lives.

But then what happens is over three years, people's lives change. People's goals change, people's financial needs change. You know, they get married, they have a baby. They decide they want more money, they decide they want less money, like stuff changes. And so we'd calibrated really well at the beginning, but we didn't keep up with it.

So then three years later, we were surprised to realize that everyone wanted different things. And we were at this strategic impasse where we closed a 7 million dollar deal in the Middle East to basically do education for the whole country, this big four year program. And, it was that deal that caused us to shut down the company because one of us wanted to run the deal as a social enterprise, basically feed all the money back into the local entrepreneurship ecosystem. Two of us didn't want to do [00:18:00] it at all because it was so far away from the productization that we wanted. And one of us was like, someone's gonna take this money, so it may as well be us. We're not gonna do the worst job. So we were at this impasse and we actually ended up shutting down the business rather than take the deal.

And I don't even know what the lesson learned from that one is, but I did know that afterwards I really wanted to get into products. So I kickstarted a board game. I was still in my learning stage, right? I was like, oh, I've never done a physical product. Let's try that. Did not like that. Manufacturing sucks. Especially, I don't know how drop shippers do it, cuz if you're manufacturing to manage quality, you really need to be in the factory. Like you need to be watching it get made. But if you're doing small runs, like I think we only made 90 grand off that Kickstarter and most of it went into manufacturing, so there's barely any profit.

I couldn't afford to like fly to China or Germany and like, sleep on the factory floor for two weeks. Like everyone was telling me I was supposed to do. I was like, no. And so that meant it was hard to quality control like a lot of problems. So I was like, okay, screw that.

David Elikwu: I think you need really tight feedback loops with drop [00:19:00] shipping. Cause I, I run a drop shipping business back in the day and I think well short of yes, flying to China, which is exactly it. Short of that, you just have to, I either get customer feedback really quickly and just chop and change. You might have to move supplier. it introduces a lot of friction. Yeah, I completely get that.

Rob Fitzpatrick: It is tough, man, and it is stressful and you hear someone gets a box and it's not what they expect and you're like, oh, how do I even deal with this?

So around that time, at some point I'd written the first book, The Mom Test about what I'd figured out about trying to do enterprise sales as an introverted techie and like the customer development and all of this. And that book had just been like, it barely did any sales at the beginning, but by three or four years after its launch, it was starting to do 3000, 4,000, 5,000 a month. And I was like oh, this is a decent income stream. I'd been kind of waiting for it to disappear or to die off. But I was like, well, it's a short book. It's a useful book for a certain type of person. It's not the best book on sales, but if you're an introverted techie, it probably is the best book on sales for you for that type of person. And so I was like, oh, there's a cool little niche here.

And so I [00:20:00] went back and started paying attention, like, how can I optimize this book? Can I treat it like a product? Can I tilt its growth a little bit further upwards? And I started to understand a little bit more about books as a product. And yeah, we got that up to 10,000 a month, 15,000 a month, something like that.

David Elikwu: I was just gonna ask with the initial growth with that? was that just through word of mouth and referral? Like What do you think kept it going and starting to get that traction?

Rob Fitzpatrick: So my like short view on books. I wrote about this in my most recent, which is called Write Useful books. It's basically if you treat non-fiction, like a problem solving product, like you treat it as something useful and you really niche down about who it's for. It's like this book solves this problem for this person at this point in their life. And you want that problem to be something that is frustrating enough to them that they're going to talk about the problem. They're gonna be like, man, this is killing me. Customer interviews are so hard or like, I just moved to a new city and I'm so lonely or like everyone's saying, being a digital nomad is awesome, but I don't feel good even, you know, I feel like alone when I'm traveling the world.

If it's one of these problems that people will verbalize, then someone else can be like, ah, I [00:21:00] know the solution to that problem. It's this book, or they might say, or this app, or this coach or this habit. Like they can suggest any number of things, but sometimes they suggest a book. And that was what was happening for the Mom Test, people go, ah, custdev it sounded so easy, but it's actually so hard and someone's like, oh yeah, I know this solution, read this book. It took over, like the way I launched it is I kind of figured that I would need to let some number of people know it existed, cuz otherwise who's gonna recommend it? So I launched it in London at a couple of events. They let me basically show up and give away books to everyone. I did one at Seed Camp Week and one at Lean Conf, I think Seed Camp Week, we gave away 500 books and Lean Conf we gave away 200. I think the conference is covered, printing costs or something. So I didn't make a profit, but I got to give the book to the right people. And I think I sold a, I did a ton of content marketing at the time. I had a blog and I was like, yeah, I'm gonna sell so many copies through my blog. I think I sold like 50 copies in total through my own channels, like books are so hard to sell

David Elikwu: I was gonna ask quickly on that, how did you get the original book deal? Was it based off your, success as a founder and business builder or because of your [00:22:00] presence that you'd been building?

Rob Fitzpatrick: The opportunity to give it away at the conferences do you mean.

David Elikwu: Yes. Yeah. well, Okay, there's a few questions to unpack. One is the original inertia to write a book, cuz writing a book is one of those things that loads of people in their heads think, oh it would be fantastic to write a book. Very few people actually sit down and do. Second of all being like the process of putting it out there. What was that like? Was it an opportunity that came up? Was that something that was just completely self-determined that you said, I need to get this into the world and you put it out there.

Rob Fitzpatrick: Useful books in particular, they come a lot out of teaching. I think teaching and listening are kind of part of writing, arguably like the most important part cuz you gotta have something worth saying and you gotta be able to say it in a way that works. And so I'd run a lot of kind of events. I'd done a lot of talking to other founders, coaching, whatever. And one of the things that seemed to be most helpful of all the things I ever told them was the way I approached these customer conversations. You know, it's kind of casual, it's kind of easy. You're not trying to be too fancy or too [00:23:00] polished. You treat them like a friend. You're interested in their life rather than trying to treat them like a client.

Anyway, so then I was on a really boring vacation. What's the trigger? Less boring and more awkward. Basically, I'd met a fellow named Rob at a startup event. My name is also Rob. We're both named Rob's and we're like, hey Rob. And we're both thirsty fellas and we had a few beers. And toward the end of the night he's like, Rob, you're awesome. You should come to Bavaria, like South Germany with me and my wife's family for New Years. And I was like, Yeah. And you know, you wake up the next day and you're like, wow, that was a terrible idea. Like never gonna happen. But then like a month later he sends me a message. He's like, well, New Years is coming up. I know this is weird, but if you still want go to Bavaria, you're welcome. And I was like, alright. And so I went out there and the father-in-law, which is he's like the King of this little south German town. He owned the bowling alley, the bar, the power plant, and he was just like a wonderful host, right? But a very like overbearing host, oh, we gotta go watch the ski jumps, like the high jumps and eat hot dogs. [00:24:00] That's what we always do. It's oh my gosh, okay, we've been drinking for like 40 hours. Like, are you sure we need to do this? He's like, shut down my bowling alley. Come on, we're gonna go bowling. We got the whole place to ourselves like, oh my gosh.

Anyway, so I was just like, at a certain point they'd put me in this like little cabin on their property. And I had no internet, no media. I hadn't brought anything to do. And at a certain point I just needed to hide from this. Like very friendly, but extremely domineering father-in-law of a dude. I didn't even know that well. And so I was just like in the cabin and all I had was a notebook and a pen. And I probably still got in the notebook actually, I'm just holding it up here if you're listening on audio. This was the notebook. And I did like, this is the original, like I just wrote the whole thing long form where I took all the things that had come up during conversations with founders that I talked to. And I was like, boom. And I just dumped all the ideas.

And then having done that, there's of like you trick yourself in a good way with the Sunk Cost Fallacy. Cuz I probably only spent three days doing this brain dump on that vacation. But then when I got back I'm like well, I started it now I gotta keep going. I can't throw this [00:25:00] away. And you know, you work it and that trick keeps working. And At some point, like I started putting it out to beta readers and I have a much more structured process for this now. It's like we got a tool for it and everything. You can find it all at usefulbooks.com.

But back then I just emailed PBS. Do not email PBS. It's a disaster. But one dude pinged me back he goes, I think there's some really interesting stuff in here, but chapters two, three, and four kind of pretentious, aren't they? And I looked at it and I was like, you know what? You're right. So I just deleted those three chapters and suddenly the book got shorter and it got better. And I was like, okay. And when I put it out, the, I think I changed it now, but in the original intro, the intro was almost saying do not listen to me. It's like, all I've ever done is fail. I don't know what I'm talking about, but this is my experience and this is my best guess of how it works. Cause I didn't know, and I didn't wanna over state my confidence or competence and trick founders into doing the wrong thing. But I'm like, hey, this is my best guess of how it works. And I thought maybe it would be helpful for a couple people.

As I approached launch data, it was really scary. And what finally pushed me to get it out the door [00:26:00] was one of the people I had as a beta reader, was helping to organize this Seed Camp conference. And he is like, Hey, that book you're working on would be really good for our participants. Do you think you're gonna have it finished in time for this big event we're doing? And I was like, yes. And then I look at the manuscript and I'm like, oh, no but that kind of gave me this like line in the sand and it launch with so many typos. But I was like, I don't care. I gotta get this thing out. And then after it launched like that, I did like five quick updates to start fixing typos as quickly as I could. At one point I even had a typo on the front cover, which is pretty embarrassing. But it did build the seed audience. And sometimes now we're like, I've got the typo version. I got the first edition with all the typos. And yeah, it was scary, but then people kept saying nice things and I started hearing stories from other founders about how it had worked or how they'd applied it. And that combination of starting small, having the thoughtful beta readers, doing lots of coaching, it gave me some confidence and the ideas.

And I still do that with all my books, where as like, I wouldn't write something unless I've made sure that those ideas work for other people. I'm doing it now. I'm writing about outcome-oriented [00:27:00] communities now as my fourth book. And it's like, I don't have a lot of experience, so I'm like talking to lots of community builders. I'm putting the ideas out there. People are trying to use them. I'm seeing what works. And it's the same thing you would do for any other products, right? You don't build it in your head in secret for years. You try to make sure that it fits into other people's lives as well. Ideas, books, they're just a different type of product.

David Elikwu: Yeah, that makes a lot of sense. I'm really interested in, you've presented two sides of a coin where, so you had that first business that you ran where one of the issues you mentioned was not knowing when to quit and not knowing when to give up and maybe extending it past the useful lifetime of it.

And I know, Annie Duke also has a great book. Thinking in Bets where she talks about this idea of quitting. I think she's actually got a new book, which is also specifically on quitting. But Annie Duke talks about this idea of so in, there's another book by Angela Duckworth called Grit, and people love this idea of grit and people espouse that, to be a founder, you have to be gritty, you have to keep going effectively everything [00:28:00] that you were doing right? You have to put your own money into the business. You have to never quit, never give up, but simultaneously, very often. Part of success is also knowing when to quit and knowing when to stop something, put a pin in something, knowing when to pivot.

And so I think you've had that side of your background where first of all, you maybe got the balance wrong of not quitting at the right time. And then you've had a few other businesses, a few other things that you've run where you have pivoted or you have quit. But then with the book, you also leaned into the Sunk cost fallacy where okay, you've spent some time writing something.

And sometimes that might be the time where people would quit. And sometimes that would be the time when people would give up on something, even if they spent time brainstorming or imagining what it could look like. But you kept going with that.

Rob Fitzpatrick: I have given up on other books. I think I've written four or five books to pretty serious manuscript stage that I never released. And I stopped them during beta reading, mostly because during beta reading you start to get signals about whether [00:29:00] it's used by your readers, right? If it's, you don't want to, like your first round of beta readings always gonna be a disaster, right? There's always some like book killing mistake in chapter one or two that stops everyone from proceeding. They're like, when we did it for the Workshop Survival Guide, my second book about education design. We did our first round of beta reading. Not a single reader made it through chapter two outta dozens of people.

And when I looked at it, I was like, that's fair. That is a very boring academic chapter. Very long, very theoretical, no actionability whatsoever. So we fix it and then it's okay, now people are getting up to chapter four, then we fix that problem. Now they're getting up to chapter nine. And then we follow up with them later and it's like, oh yeah, I used that. This is what happened, or I tried this, it didn't work for this reason. It's like, okay, that's a bug, that's a bug in my book. Like, I can go fix that bug. And like I've done some beta reading where I'm like, I cannot fix these problems. Like these problems are too fundamental. There was one where I rewrote it like five times and I was just like, I'm just not, maybe I don't understand the content well enough. Maybe I'm not a [00:30:00] good author to make it come across. So I would never give up after the first version. But at a certain point I'm like urgh, and then there was one when I started reading, I was like, actually, I don't care about this topic. And I just stopped for that reason. I was like, I don't want to promote this book. I don't want it. I've screw it, and I just shut it down. I was like, oh, that was, fun, like three months writing a manuscript.

David Elikwu: Fair. How do you know which feedback to take and which to discard? Because I think this maybe goes to some of the principles and some of the things that you talk about in The Mom Test, but this idea that we should be going out, we should be getting beta readers, beta customers, testing the market, getting feedback from customers, but some of it is useful to help us iterate and help us change, but then some of it might not match the vision of what we're trying to make.

Rob Fitzpatrick: So one thought is that, your customer segmentation really matters. Let's say you have a new idea or you're thinking about a problem and you go talk to 10 people and like eight of them don't care at all and two of them care a lot. When you look at the like the naive interpretation of that data is like, oh, only 20% of our market cares. This is not [00:31:00] good.

What's usually true or closer to the truth is that when you talk to 10 people, you didn't have a clear sense of who you were trying to talk to or who your customer segment actually was. You were looking at an industry like I had one where it was for universities, so we talked to 10 universities.

Only two of them cared. But it turns out the two that cared were the ones who, their self identity as universities were that they were the experimenters and the creators of best practice. So they were willing to try new stuff, even if it might fail because they had the budget, they had the reputation.

They weren't gonna go, no one was gonna get fired. They were supposed to try new things. Whereas the other eight were either the followers of best practice or they were just trying not to get shut down and have their funding cut and they couldn't afford to do anything. And so we go, oh, so our customer segment isn't universities. Our customer segment is like the experimental visionary, like leader universities, the setters of best practice. And so then you talk to another 10 and [00:32:00] instead of two out of 10 caring, eight out of 10 care, and you go, aha, we found our segment.

And the same can be true with book feedback, where with the Workshop Survival guide had the best example where I thought that the ideas of running a high energy workshop would be interesting to teachers to like school teachers, to university teachers. And so I included some examples from their world. They hated it, hated it. Because it is harder to teach students who are forced to be there. Then it is to teach adults who choose to be there, just fundamentally. And also, I might have a month to prepare for one workshop, whereas teachers have to come up with a new class almost every day. So, they felt like I was talking down to the challenge of their situation, and they reacted with enormous hostility, right? They hated the book. And they would get really angry at me, and they sent me a lot of mean notes. But as you dig in to that, and you understand why, right? you kinda use the metal detector. You try to get the signal behind the noise. And I'm like, oh. And I realized what I just [00:33:00] explained to you. And so I removed all of the examples about classrooms and I made all of the examples just be about professional workshops for adults who choose to be there. I was like okay, and then once I'd made that choice, I ignored all of the feedback that had come from teachers. I'm like, that feedback is, I've like made the change based on that feedback, right? Which is like, they are not my reader. And I filtered that out from my mind and I said, thank you so much, you really helped, I changed the books in these ways. Like, you were totally right. You know, You wanna be grateful cause they did make it better.

And then the funny thing is, after I launched the book, I started getting emails from teachers who said, I know this book isn't for the classroom, but the techniques are so helpful, I really loved it. I've applied it already. And I was like, oh yeah. But the positioning matters and so both of those cases, like the, which type of university, it's like a segmentation issue. And so that's one thought on which feedback to ignore.

And the other thought is, I use this metal detector metaphor, especially with feature requests where when someone requests a feature or they say, I love it. I hate it. You [00:34:00] need to do this, don't do this. I think of that like the metal detector, you know, you're scanning the beach and the metal detector goes beep. You don't go like, Aha, I found it. Time to go home, like job. No, you go, wait, there's something here. Maybe it's trash. Maybe it's treasure. I don't know. I need to dig. And so then you get down on your hands and knees with that little bucket and you start digging, right? You don't know what you're gonna find. Maybe it's a pile, tin cans. But sometimes it is, you know, I guess someone's wedding ring and they're really sad they lost it. I don't know. It's not my hobby. But the, you do the same thing with all of these. Like when customers tell you things, that's not the data, that's not the treasure. That's the metal detector going beep.

You still need to dig. Usually several layers underneath that comment, like, why do you want that feature? What would that let you do? And sometimes it falls apart. They go, oh, actually I don't think I would really use it. It's just a cool idea. And you're like, yeah, it is a cool idea. And other times you realize it's a critical buying criteria, but you don't know unless you dig in a little bit.

David Elikwu: Yeah, So on the flip side, how do you decide which projects to start? Are you usually, the question in my mind is do you [00:35:00] start with the book or do you end with the book? You've written a lot of books, which are about things that you've discovered through practice and through learning and through coaching and teaching all of those things. But I'm interested to know how you go about pivoting between each other different topics.

Rob Fitzpatrick: Yeah I do other types of products also like we run useful books like, that one started as a book, but then we built a software thing and an author's community, and so now we've got like a whole business there. There's a five person team and we're bootstrapping and you know, it's got all those pieces.

Like I do software stuff on the side as well, so I've got a few different things going on. But, so I am ADHD, and one of the qualities of that is that it is really hard to stay excited about stuff that you're not excited about. I, know that sounds like self whatever, like nonsense, but it's hard for me to convince myself to be excited about something. I have to actually be excited about it. And when I am, it's very easy to dig deep right, to focus on it, to stay interested. And I've learned, like one of my big lessons from the first business is I cannot force myself to stay interested. I gotta actually be [00:36:00] interested. So I value the optionality.

One of the things I like about bootstrapping is that I am able to quit if I realize that like it is no longer a good fit for me. It's harder with a team, right? Cuz you need to be respectful of other people's commitments and you want to try to, you know, et cetera.

So that's the first thing I look for is like, am I really excited about this? With books, with businesses, with all of it. And one of the filters I use is I force myself to talk to lots of people. I do not really like talking to people. I'm introverted. I'd rather, but if I'm excited about a topic, I will overcome that. Cuz I care so much about the whatever it is, the problem the possibility space, the product. And when I'm talking to people, it's fun cuz we're talking about the thing we both care about and it's like, yeah. And if I'm not willing to talk to the people up front, I know I'm not gonna be willing to do all the other work later. So it's a helpful filter for myself.

Then with books it's like, do I wanna spend two years thinking about this topic? Is this a two year topic or is this a two month topic? If it's a two month topic then I probably should make some videos or blog posts, but not a book. If it's a two year topic, then it is probably a book, right? And then a business is [00:37:00] this a five year topic? And not every business has to be a five year thing. It depends on the table stakes, how long it's gonna take to start up. Like some ideas are just slow to build and slow to validate, and you kind of have to give it five years for it to have any chance. Other types of ideas, you can get a pretty serious signal in three months and you can make a data driven decision.

One of the great lies of Lean Startup is that you can make these sorts of data driven decisions about every idea. And you can't, there's some ideas where it works really well, but there's other ideas where you go let's give it half a decade. See what happens. But you only get to make that choice, what, 10 times in your working life, you only got 10, half decades to give to something, maybe eight half decades. And so you go, oh do I really care? Is this a half decade idea? And I think about that. And then when I'm looking for what I'm gonna the people entrepreneur first really good kind of global accelerator. Alice Bentinck, she has this concept that she calls Edge, where when they're looking for the fit between an idea and a team, they're like, what is this team's edge? Their unfair advantage. And she looks for like deep [00:38:00] expertise in the industry or with the customer. Deep technical know-how that would allow them to execute in a way no one else could execute, stuff like that. And I look for that, for myself. I'm like, where's my edge on this idea?

Because I don't know, I'm getting old now, man. I'm lazy. I don't wanna work long hours. I wanna work fewer hours and get better results. And I can only do that if I kind of stack the deck in my favor, which means playing to my strengths. So I'm like uhhhh, am I interested? Do I have Edge? Do I like hanging out with the customers? If so, then yeah, let's go for it.

David Elikwu: So I mean, that probably leads to another question maybe about the lifestyle that you've built for yourself and the life that you've built. A question that I guess I probably wouldn't ask now was whether you'd ever considered going and working full-time at all, cuz it seemed like everything was quite linear and, then you've just followed your passions from stage to stage and eventually there were some things that found success and then it was common sense in some respects just to keep going down that path.

Rob Fitzpatrick: It is been wind day, so the books have been great for me cuz they've been, even when it was only a little bit of royalty income, I think [00:39:00] now the three books do something like 25,000 a month in royalties, which is good, right. And that's pretty much on autopilot. And some of that we used as bootstrapping capital. Like we took the third book's revenue and used that as our bootstrapping capital for the most recent business. Which was really helpful. It let us hire some employees earlier than we would have been able to otherwise cuz we have that bit of cash flow. So that's given me a cushion where I've been able to be pretty playful with the types of ideas that I go after.

And I tend to prioritize the things that I'm gonna learn the most from and be most interested in. But I've also taken time off. I took three years off to learn to sail, fix up a sailboat and, putter around. I took the boat from London where I bought it and fixed it up to Barcelona over like three summers and I lived on it for a couple years. So that was kinda like my sabbatical period. And at the time I thought that I was gonna do the early retirement thing. I told people that I retired. My partner Teresa, she was joking the other day. She's yeah, when we met you told me you were retired and now you work all day. This sucks. And it was [00:40:00] true.

And like I, you know, it felt like I had the book income, I had the financial stability. I was like, yeah, it's fine. I don't, I got no ego in this race. I don't need to have a big success anymore. But then at some point when the boat was in Barcelona, my buddy Devon, he had some sort of work emergency, like with a project with something.

And I was like, yeah, I got free time. I'll help you out. So we spent a week or two and we hustled this deadline together and I can't even remember what the project is, which is funny. But anyway, like it was so much fun to be working with someone much smart on something under like intense circumstances with a bit of pressure being able to flex the creative muscles.

And I was like, eh. It was like, like I loved it. Like the adrenaline, the excitement, the creativity. So I was like, let's do a business, you know, like. And so we got back into it and I was like, oh, I don't actually want to be retired, I just don't want to have to do bullshit. But to work on interesting things with smart people is great. That's what I want to be doing. So yeah, we started, we set up a structure where we both worked on separate projects, but we shared the profits and we ended up distributing about [00:41:00] 450 grand in profits that way over three or four years. Where, sometimes he'd be making more money and it would come my way. Sometimes my stuff would be making more money and it would go his way. And it was kind like a two person skunk works, but it was very flexible because we didn't need to get each other's approval. But it meant that if one of us. Had something that showed some promise. It was very natural for the other one to come in and collaborate on it because we both had half on anything that worked.

And then two of those things ended up showing enough promise that we tried to turn them into businesses. One we spent about a year on, and then we're like, nah, and we shut it down. And then the other one is what's now The Useful Books business, which is like the beta reading software, the authors community, the book. And that's been really fun. I can't remember why I started that rant, but, oh yeah. That's why I got back into working. And the way we tried to set up that business is we said so Devon works part-time as a venture capitalist. He does like startup investment stuff. And then we wanted to bootstrap this business and I like to work on my books and I have other projects and stuff.

So from the beginning we said this was a 20 hour a [00:42:00] week business. It was always gonna be three days a week or halftime or whatever. And we pretty much stuck by that. And as we hired people, we added one more partner and we hired a couple employees for everyone. It's like, Hey, this is a 20 hour week thing. Like we're not trying to go full time on this. Like we take our time, we got the cash flow already. It's like, you know. The downside of that is it makes you move slow, right? Because, and so there's some stuff that takes us 12 months that we probably could have gotten done in four months if we'd really been like together in the same room and hustling it.

But it's also been nice. So there there's tension there. Like every aspirational value has another side to the coin. As you say, it's like we work at a relaxed pace and we're okay with things taking longer. Like we go fast, but we're okay with breaking things like, and I found that whenever it's like you have this cultural virtue, you should think about what you're giving up for that and be comfortable with that. Cuz otherwise you go crazy, right? Cuz you want all the good stuff and you don't know which trade offs you're actually making.

David Elikwu: Yeah, that's a really good point. So how do you manage your time and your energy between the different projects [00:43:00] between this business that's going at whatever pace it's going and other things that you might be interested in?

Rob Fitzpatrick: Not super well. I've also got my first, first kid on the way, arriving in a couple months. So that's on my mind and I'm trying to set things up to take a proper paternity leave and everything like that.

And so, the theory, this is theory, is wake up, do my writing for a couple hours cuz my writing is like, it kind of drives my personal projects my personal business. And that's where I get my biggest sense of craft. I'm no longer programming. So most of the stuff that I do for the business, it's more like management, marketing, admin, community, customer support. It's important stuff, but I don't get like a deep sense of craft from it. So I like to start my day, do my writing and take care of my personal stuff in the morning in theory. And then afternoon is like, meant to be for the business and whatever has to get done. In practice, I haven't found that clean division has worked for me. Maybe someone more organized could do it, but I have waves of excitement and energy and so I try to work [00:44:00] off of a weekly schedule rather than a daily schedule. So I'm like, this week I need to get these things done, and then on certain days I'm like more excited about it or less excited, so then I, you know, it gets cranked up or scaled down or whatever. And cuz it sucks. If you're super excited about a project, it sucks to be like, okay, that's enough of that onto the boring thing cuz you know, you're like, you lose the wave that you're writing.

But I started working with a coach, so I've got a, I've been working with an ADHD coach for the last year, which has been good. I've really like leaned into the support network like talk to my team about like, the tasks that seem to be really anxiety creating for me, or where I seem to lose disproportionate amounts of energy.

We've hired employees to take over some of those mundane tasks or to outsource them. We be good about the processes. And that stuff was important. When I was trying to just deal with it all myself, I was slipping back into burnout pretty noticeably. And once I started being like, actually, guys, I don't wanna do this again. Here's my situation, here's what's hard for me. Everyone kind of rallied and that was a, you know, an important moment for the team. And, I don't [00:45:00] know, trying take things less seriously. It's not the end of the world if an email goes out with typos or something, even though it feels like it is.

David Elikwu: Yeah. I'm interested to know what you think about maybe the wider quote unquote creator economy or people becoming like solopreneurs or trying to go into business where they're either like a one man band or a small group of people in a similar way to some of what you are doing. Because I think we've seen particularly recently, okay. One is the economy and how things are going at the moment, but I think we also had a very, not glorified, but we had a heyday during the pandemic period where I think it was all the rage everyone was talking about creators, the creative economy, this and that, web3, all of that. The web3 part has fallen to the wayside, and

Rob Fitzpatrick: Hmm.

David Elikwu: to know how you see that evolving for the majority of people.

Rob Fitzpatrick: I think there's a lot to say about that. One more thing I just wanna latch back onto the previous topic you asked me about the days, cuz there's a couple practical things that I probably should have mentioned. So these are just things I learned. Maybe this is common sense and everyone else knows this, but this was new for me.

Sleeping well isn't about what you [00:46:00] do in the evening, it's about what you do in the morning. So waking up, getting natural light, like the exercise you do in the first half of the day it tells your body when you're supposed to be falling. So it was actually like building a morning routine that allowed me to start sleeping better and like that makes everything easier. And then getting a bit more like heads on with the business anxiety. Cuz when I was avoiding the business anxiety or trying to like distract myself from it, then it's like I'm not sleeping well. I'm thinking about it. I have to play more video games to distract myself in the business problems.

But actually I started getting, I live in the mountains in Northern Catalonia and little farming village, like 20 people. We've got really cold mountain water here. It's like a 10 degrees celcius. It's like below 50 degrees Fahrenheit. I started getting into this, like this cold water stuff, and I was like, oh, it distracts me from all the business drama and I realized you can use that kind of like exposure therapy where you're like, it's supposed to be uncomfortable, but I'm going to like enjoy like putting up with it for a bit.

You can use that for the business anxieties as well. So I'm like, oh, I'm really anxious about this business problem, but instead of like distracting myself from it with video [00:47:00] games, it's like, let's expose myself to the uncomfortable cold water of this business problem and just like work it, and work it a little bit more each day. And one that's like great for your brain, but also eventually the problem goes away, and then you don't have to hide from it anymore. So those two things, like getting the sleep right and like gradually exposing myself to these anxiety sources more and more until I deal with them was crucial. And my days have been a lot better since then.

Anyway, so as for the creator economy I think it's amazing. There's so many options, but I also think that most people are not as good as they think they are at what they do. And so I've tried to hire a lot of freelancers who talk a big game on Twitter, and as soon as I start working with them, it is clear that they are not very good. And then like you can see them on Twitter being like, ah, it's impossible. Clients are blah, blah, blah. Fine, you know, maybe I'm the jerk in this scenario. I don't know. But I'm not saying that to be mean. I'm saying that because this is like a distinguishing factor. Like think about how many restaurants you go into or small businesses where you're just like, if you just fix the service, if you just added another waiter or waitress, if you [00:48:00] just like, major website sensible, instead of being this ridiculous like motion graphic promotional brand story, like just show me the menu and the opening times of the phone number. Like If you get the basic stuff right, it really sets you apart from the crowd cuz the crowd is very bad. Like they are not good at what they do. You've got all these idiots on Twitter spending all of their time trying to write threads in a way that the AI can clearly do better already. And what, okay, imagine how stupid someone needs to be to follow someone who spends all day writing threads. That's an AI could write. Imagine the value of that person as a customer. It's like zero and so they're spending all day learning a skill that has already been commoditized to attract an audience that has no value. I don't understand what theyre doing. And then they're like, yeah it's like, you know.

Learn how to understand people's real problems. Learn how to be good at like customer support and customer service. Learn how to design a good user experience. Learn how to have a unique thought that isn't just like an [00:49:00] AI respin of what everyone else is saying. It can't be respond because it's yours. Like you came up with it.

And I feel like there's an infinite opportunity for any creator, in almost any industry to just be like, actually I'm gonna do this better. I'm going to be better. And if you can do that, man, like the opportunities are crazy. You can go anywhere. I can't, like, there's so many roles I would love to hire for and like I don't even need them to be full time, right?

If someone's like, I can do this in an hour a week and it's gonna cost you this much money, I'm like, yes. But I can, I hire these people and they're like, ah, well whatever, this doesn't need to be Rob complaining for an hour. But yeah, if you get good at a skill and, but it's just not, it's not just the skill, right?

It's like you gotta be able to manage up, you gotta be able to manage sideways, you gotta be able to communicate. You gotta be able to listen, you gotta be able to teach. You gotta know a decent amount about tech and product and like, we're back to the era of the generalist, which I actually think is cool because I don't know about you, but I always used to romanticize this era of like Leonarda DaVinci or the Enlightenment, where like you could learn everything like if you look at Leonardo [00:50:00] DaVinci's old Resume, have you ever seen this?

David Elikwu: No, I haven't.

Rob Fitzpatrick: So there's a copy of Leonardo DaVinci's resume, cuz he was basically applying for patronage from like kings and royalty. That's how like you made a living back then as an artist. And, his resume's incredible. It's like, I can build weapons of war, including catapults, like digging machines that will go under enemy walls and collapse them. I can build beautiful marble statues of your likeness. And then at the bottom it's like, I can also draw, it's like a footnote. It's like I can draw a little bit. And so one, it's amazing that he could do all these things, right. And it's like, so exciting, the fulfilling life to be able to draw from all these different like, areas of knowledge. But then it also shows that he really understood what his customers wanted. His customers, in this case were kings who wanted to wage war. You know, him being able to draw is like the least of their concerns. So he also had that empathy, that understanding of what his customers wanted, which allowed him to build an interesting career.

I don't know. I feel like we're, I don't know, but don't listen to me though. I got lucky.

I will tell you my career strategy [00:51:00] is to find something I'm interested in. Figure it out, build some products in the space, get to know other smart people in the space, learn a lot from them, and then eventually consolidate that into a book and move on to the next interesting thing, and, I don't know, 3, 4, 5 years per topic. Get a book at the end, move on to something new. It's pretty fun.

David Elikwu: I'm interested in. Okay. Something you mentioned about this idea of writing and everything that you said about Twitter. I completely agree with. I was talking to someone on this podcast actually quite recently, David Kadavy and just talking about this idea that, you can write really good stuff but part of the reason I think you see this proliferation of people that write. The robotic AI tweets is because, they have figured out how to game the system and there's a certain thing that works and if you keep pressing the button and doing the thing that works, eventually you'll get the clicks, you'll get your attention, you'll get all of the stuff that comes with it. And so what's hard is trying to find the balance of doing something good and putting something good out there and sticking with [00:52:00] just optimizing for quality versus optimizing for audience capture and just trying to get as many eyeballs as possible.

So what do you think of that balance where, you know, on one hand you want to do the good thing, but on the other hand, if you could produce lots of good stuff and no one sees it, or do you think that it always happens that if you produce good things, people will find it.

Rob Fitzpatrick: No, marketing is important, right? Like distribution is hard. I mean, this whole like Twitter, like AI writing thing, the moment we're in right now, it reminds me a bit of what happened when AdWords was new and SEO AdWords arbitrage was a thing cuz the SEO market was very inefficient and so people could come in and capture all the search terms and then just redirect it through AdWords clicks. And a bunch of people got really rich doing that, right? And that's fine. Like, some people aregoing tobuild really big audiences that they find a way to monetize through like AI writing Twitter shenanigans, right? But like the SEO arbitrage, it's zero value creation, right? And personally, like if I'm [00:53:00] investing my time in something, I don't want that to be like shuffling papers around a desk for no purpose, even if I make some money doing it. Like I want to feel proud of the way I'm spending my limited life.

And there's people who got really rich doing like AdWord arbitrage. People will get rich doing, I guess like Ai fortune cookie arbitrage. We could call it. Like pretending to be a human. When you're really an AI fortune cookie, it's like, great, like you can get rich. If you value your life so little that like you're willing to advance closer to your grave, like by doing that for money. It's like, it's insane to me, but fine, like power to you. But then like at the end of the SEO arbitrage era, a bunch of people were like, this is unfair. Google took away my livelihood. And it's like, this is not unfair. Like you were doing something that was fundamentally non-value creating, like you are a human parasite, you know? And like, good, you got good and fat. Be happy that you got anything. So, whatever, people can do it. I'm not gonna say it doesn't work. Like my audience grows slow as hell cuz I like, I put zero thought into it. My thought goes into like, how do I spend my time doing things I think are interesting? And by putting them out there, like I'm not trying to put them out in like an [00:54:00] optimal way, but enough seems to come back to me. I don't know. I'm not gonna say there's gonna work for everyone. Maybe I have some super power or secret talent or I'm blessed. I like, I don't know. But my first book, like it sold 150,000 copies now and I had zero audience when I launched it. I still have maybe I have 10,000 Twitter followers now, but I've sold like way more books than I have Twitter followers. And sometimes I look at people who are like, they've got a million Twitter followers and they've sold 10,000 books. And I'm like there's something's wrong there, right? That says something about the quality of the book.

And there was a, I wish I could remember the fellow's name, but he's in the web3 space, but his quote that stuck with me is he goes, make things that become more famous than you. If you can only sell stuff because you're famous, then you're not making good stuff. Like being famous like is great, right? It's a great multiplier. By all means. If you can be famous, like it seems fun but that's not Plan A. Plan A is make good stuff, and yeah, then you need to figure out how to get it out there. That's hard.

The way I like to think about audience is. Do people know that you can do something well? And [00:55:00] do they believe that you can do that reliably? That's essentially what, like what it is. Like when I was teaching workshops, the reason people hired me, even though I wasn't the flashiest was there like, I was very predict. They're like, I know Rob can do this. I know he will show up on time. Like I know he will deliver it consistently. If he gets sick, I know he will send someone who's also pretty good to take his place. It's like, you know, covered. I had no followers, but we were able to build a decently sized teaching business, right? Because I, it was reputation and you don't need to see them as a follower account. If people have read my book and liked it because I've made good what they consider good work and I put it out into the world. Even though they are not following me, like they are in my audience. Because they believe in the quality of my work and should I ever need money or work or opportunities, right? I don't know, I just don't believe that the number on Twitter or on your newsletter list is an accurate representation of what that audience is actually worth.

Brennan Dunn is amazing with his email stuff, and he has this like, side project. He's got like 50 businesses, but his side project is Create and [00:56:00] Sell. He did a newsletter the other month quite recently where he basically shared all his numbers and he doesn't have that many subscribers. It's like 10,000 email subscribers, something like that. But what blew my mind is that 30% of his email subscribers have bought something from him.

David Elikwu: Yeah, I'm one of them.

Rob Fitzpatrick: Yeah, Me too. Me too. I love this stuff. He's amazing. And but 30%, like what's the typical conversion off of a list? It's single digits for sure. And I say it's like, why is that? right? He's become one of the best in the world at email marketing. He's like, ruthlessly authentic. He's super consistent. Like, you know, it's gonna be high quality. You know, and he's built this beautiful business that most indie creators would kill to have. He said he does it in like five hours a week, something like that. And it is like this six figure approaching, seven figure little side business. I don't know. He's the role model as far as I'm concerned, right. Get good. Have unique thoughts. Do it authentically. Do it consistently. It's not about the pure size.

David Elikwu: So right on the top of that, you're just talking about this idea of becoming the best in the world at something or [00:57:00] being able to produce something of high quality consistently. But then also we've talked about your whole journey, right? Your whole background. A lot of the stuff that you've shared has come from things that you've learned. And I think in your career journey, you've followed the compass and not the map. You've followed your interest and found and discovered and shared what you've discovered rather than, I don't think there's any linear path that takes you to where you've ended up.

So I'm interested to know, if you were to go back and you were to start again from your, let's say early twenties or late teens. How would you start and where would you start?

Rob Fitzpatrick: I got into programming when I was in high school, which was probably the best thing I did for myself. And that was fueled by video games because I wanted to start making mods for my favorite video games. And I needed to be able to write a little bit of code for that. And, It's funny how much like effort my parents put into trying to get me to stop playing video games.

But it was because of that passion that I got into programming early and then that led in useful directions. I think that was fine. That's why I went to, followed my interests in most steps. There were a couple places though [00:58:00] where it's like follow the interest but also have kind of constraints or unconditional on that. So as much as I love video games that's what got me into programming. That's what I went to university for. The video game industry is a very terrible place to work. And so as soon as I realized that and I had friends inside the industry, I was like, oh, so I shouldn't do that. I should find another way to apply my interest.

So that's when I went the academic, like video game research route. And then I was like, oh, wait, actually that's way more political than I'm interested. So I was like, okay, how can I spin this into the startup route? So like, it's like both constrained by, it's like constrained by the interest, but also like limited by the pragmatic realities. Right? Like I was just reading an excellent write up by someone who's been a professional pixel artist for a long time, making pixel art for video games and stuff. And they've been playing with you know, the new AI art stuff and they're like, oh, it's not quite as good as me yet, but it will be really soon. And they've already started pivoting their business into teaching other [00:59:00] people how to use the AI to make art like they make, whereas I see other artists who are complaining and they're like, oh, my job, my career, I've worked for years to build this thing and now everyone can do it. This fellow is like, oh, I can see the way this is moving. Very pragmatic, right? It's oh, let me be the teacher. Let me enable this for everyone. Like, how cool, right? And that person's gonna make a fortune.

So, I see both things. I'm very curiosity driven, I think therefore I am this sort of fundamental axiom. I feel like I'm curious about it, therefore it is worth doing. And that's like a fundamental axiom. I design games as a hobby, right? For fun, it's like something I do for jokes and maybe play a board game that I made with my friends sometime or I'll do like, I'll have a free weekend and I might do a little prototype of some video game, but I don't wanna get into that industry. That industry sucks, So like, that's a hobby. I do that for fun. Books, I also really like books and I can make money. Okay. So I'll do that more as a business. Right now, community, tick both boxes. I like teaching. I don't wanna fly around the world anymore. That no longer fits my life. But like, community is a nice way to [01:00:00] teach and it's got a good business model and I don't need to leave my chair. So it's like, okay, I'll do that. So it is like self-directed, but also like eyes open to the economic reality around. Not everything can make money. Not every good product has a market for it, but you know that, that's part of your job is to find the fertile soil for the thing you care about and like find the right place to plant it.

It's not about becoming the best in the world, like out of everyone or for everyone. It's about being the best in the world, like for a certain type of person at a certain moment in their journey, right? If you're learning how to program, like you don't want to be learning how to program from the world's best programmer. You want to be learning how to program from someone who's like a few months ahead of you in the journey, and they've still got the empathy for your worldview, your problems, your frustrations, your confusions, right? And so it's possible that teacher who's like only been programming for six months, but is really thoughtful about it, is the best teacher in the world for those beginner students.

And like if you're teaching lawyers how to program, like, that's gonna be a different best in the world [01:01:00] for that group of people than if you're teaching children how to program. So I'm not the best in the world at like, anything I do, but like there's a certain group of people who I am the best for because I'm speaking in their language and I understand their worldview, right. So it's also about finding your people and, and like, I think that's what people mean when they say be authentic. It's like, know who you are, you know, plant that flag, be proud about it and then like, you're gonna be the best in the world for someone.

David Elikwu: Yeah. No, I think that's such a good point. Just this idea of putting something out into the world and also using you as an example, a lot of the other stuff that you do centers around the core mission. And I love the point that you made earlier about, people don't think you're credible because you've written the books.

They, sorry. People don't think that,

Rob Fitzpatrick: People don't buy my books because they think I'm credible. Like they think I'm credible because they got value from my books, right. So it's like, I put work out that people like. People judge the work on its own, they don't like my stuff because of me, right. It's like, people have the arrow of causality backwards there.[01:02:00] Like maybe if you're buying, like whatever from some superstar celebrity makeup, you're buying the makeup because of the celebrity. But if it's a useful product, if it's a problem solver, like you're not gonna buy a coffee machine that doesn't work because a celebrity endorsed it, right? You're gonna buy the coffee machine that works and then you're like, oh, who made this? They're good at making products, right? Like people have the arrow backwards.

David Elikwu: Yeah, it's a really strong point, and even with writing, most people do naturally just now assume, oh, I wanna write something, therefore I have to build an audience. I have to go and do this whole other exercise of audience building and finding people, and how can I get attention, blah, blah, blah, so that I can do the thing that I actually want to do.

Rob Fitzpatrick: Yeah, you do need to get it out there. So for books in particular, I think of seed marketing is like, it's my job to find the first thousand perfect readers. And then once I've done that, which can take a while, it's a pain to find, you know, early marketing is slow. But then it's like, okay, at that point then word of mouth should kick in if the product is good enough. And if it's not good enough, then the book deserves to fade away. Right? I don't wanna [01:03:00] force people to read something that they don't like enough to recommend. So that's how I think about it. But I commit to do manual marketing up to a thousand copies, and then I'm like, okay, it's not gonna do its own thing. That's not possible for every business. Some products are inherently recommendable, some aren't, but you know, yeah, you gotta do something. But it is not, it's not always about getting famous, right. There's sometimes easier paths to the goal.

David Elikwu: Maybe as the last thing, maybe you can talk a bit more about what you're building with Useful Books as a business. Cause I know you are doing the community aspects. You've got some beta reading software, tell us more about that.

Rob Fitzpatrick: Yeah, so useful books is we're trying to will eventually help the publishing industry. Cuz basically everyone thinks that writing books is a total gamble where kind of like, venture capital or something where it's like, yeah, write 10 books maybe one of them works. And even big publishers kind of have this worldview. And then it, you know, authors think about it. And if you think that you're spending a year of your time on a book that's essentially a 1 in 10 gamble. I don't know, that's weird, right? And then people start cutting corners, they're like, ah, it doesn't matter anyway, [01:04:00] it's all a gamble. It's like, no, you can apply a sense of craft and product design. You can make these things work.

So the business we're building is these three parts around that thesis. So there's the book itself, which is like, here's the knowledge, here's the process, here's how to apply modern product development and iteration and learning to nonfiction. Then we've got like the author's community, cuz you got this process, but it's hard to put into practice. Like, you know, writing a book takes a long time. Sending an early manuscript that you know has problems, sending that to beta readers is terrifying. So it's helpful to do that in like a group. So we have the community, which is kind of like if you're thinking about this as a regular product business, we've got like the knowledge or the process. Then we've got the customer success community. And then we have a piece of software which called Help this book, which is specifically for beta reading. So we're basically like along this journey that you're gonna have to take to get to success. There's a special extra annoying pain point, that there's not a good product for us. We've like built the software product there. And we do it on a bundle of subscription, you asked about the business model. So basically like the book, and I'm in the process now of doing an update to [01:05:00] the book and we're also like, we're giving the web version away for free. We're gonna give the whole book away as like an email drip course. We're going to give the whole thing away as a YouTube series. So you can buy the book and you can watch it for free. Because what that really does for us is like, that's kind of our content marketing and our mindset changed, which turns someone from like a random non-fiction author into an ideal customer for us.

And then the community and the software kind of bundled, and we think of it as an outcome-oriented community, which is the topic of our next book, where we're not trying to keep people forever, we're trying to get them to a successful book and then let them go. It's like we graduate them, we're like, you have graduated, you have done it. Congratulations.

So we have a couple hundred authors in there now and you know, they go through and it's really cool. I think for a lot of marketing led software businesses, having a customer community that you really invest into, it takes a lot of time. It sucks to run a community, very time intensive. But it's a customer development superpower, cuz you get to watch people struggle all day and you get to see what they get stuck on. Like the dream of customer development is to get to watch people doing their [01:06:00] work with no bias. You want to get, see what people do not hear what they say, right? Because what they do has no bias in it. What they say has lots of bias and a lot of the tricks of the mom test and customer development is around getting around that bias of what they told you. But if you can set up these customer success communities, these outcome-oriented communities, you can just watch them. There's no bias. It's incredible. The quality of learning is so good. And then people have problems and it's like, oh, I can help you with that. Let's jump on a quick call. Boom, you're in a cust dev call.

Like you're helping them with their problems. You're talking through all the nuances, right? And they're so happy cuz they're like, wow, thank you so much for giving me this time. It's like, no, thank you. Like this is my customer learning. And, and so both sides are delighted. It is labor intensive, but I think it's really powerful. So anyway, that's our business.

Oh, and then long term we wanna launch a publishing house. And our thesis for the publishing business is that during beta reading you get a lot of data, both qualitative and quantitative, on how a manuscript works for readers. Are they getting to the end? Where do they give up? Where do they skim? [01:07:00] Is it getting better version after version, like is the author iterating? And we think that with that data we can really make a more predictive about which books are gonna succeed. And then that means that we can make more generous publishing deals to authors because from our perspective it's not as risky and we really want to bet on first time and un platformed authors. So authors who have never had a successful book before and who don't have a big audience because that's who the publishing industry values the least. Cuz they don't know what to do with these people. And we're like, well, we can look at the performance of the manuscript itself, make them an offer. And, you know, anyway, we're doing that, we're starting with a kind of like agent model where we're passing like one pagers of some of our community members to other publishers. So basically like, this is a new author and here's the data about their books, performance with beta readers. Then we can send that to publishers and if publishers end up publishing that author, we got a commission. So then that's like a transitional model, so it's like information [01:08:00] product, community, software product, and then eventually leading into this hopefully disrupted publishing model.

But we'll see a lot to do for five people working halftime.

David Elikwu: Yeah. No, but it's an amazing vision and I really think that sounds like it will really revolutionize the publishing industry. I know that I've seen a lot of stats about how few books are actually read. Where, you know, you have people that get these big publishing deals or all of this stuff, but like you said, publishers very much treat this like venture capital where they're going to invest in a bunch of books in a year, knowing that a few of them will only be read by a handful of people, and a small number will be read by thousands of people, and that's the entire bet.

Rob Fitzpatrick: And if you look at the publishing industry, especially for nonfiction, all of the money comes from the back catalog, which is books older than six months, they continue to sell. So if you look at New York Times bestsellers, they hit peak sales on average, they hit peak sales at around 12 weeks.

And then by the end of the first year, they've lost 95% of their peak sales, and by the end of the second year, they've lost 98% of their peak sales. [01:09:00] The exceptions to that I wanna say it's about 2% of the books are the exceptions, where they become the back headlock. I might be fudging that number, it might be 5%, but their responsible for like 90% plus of the publishing industries profits, and they take barely any of the marketing because they're selling through word of mouth. And so the whole challenge, at least for nonfiction as I understand it, is like, how do I specifically aim my book for the back catalog? It's like, solve a problem, be able to grow on word of mouth and be able to last for at least a decade.

Like, you know, pick these long lasting evergreen topics. And if you can aim for the back catalog. And then if you can test for recommendability, you know, and problem solving ahead of time, then you really change the dynamics of the publishing industry, right? Because you're cutting out this group of books that's like a flash in the pan and doesn't actually drive long term profits. So it's like, it's all about making the back catalog classics and doing so intentionally. At least in my opinion, you can make an art book about whatever, of course, you know, if you're doing it for art, like do what you want. But if, you want the book to be a business asset or an income stream, [01:10:00] you know, back catalog problem solver is the way to go, in my opinion.

David Elikwu: Yeah, that's how to make useful books.

Thanks a lot Rob. I really appreciate you making the time.

Rob Fitzpatrick: It's my pleasure, thanks to having me.

David Elikwu: Thank you so much for tuning in. Please do stay tuned for more. Don't forget to rate, review and subscribe. It really helps the podcast and follow me on Twitter feel free to shoot me any thoughts. See you next time.

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