David speaks with Rob Fitzpatrick, author of three books, including The Mom Test and Write Useful Books, both of which are among the most universally recommended books for early entrepreneurs and non-fiction writers. His books are used in universities such as Harvard, MIT, and UCL, and are also manuals for training at companies like SkyScanner and Shopify. He has led training programs at companies like HP and Sony Mobile, and has supported many startups and entrepreneurs.

They talked about:

πŸš€ Rob’s Y Combinator journey

πŸ”„ Lessons learned from a failed pivot

πŸ’‘ What to learn and unlearn in bootstrapping

✍️ The process of writing the Mom Test

⏰ Knowing the right time to quit in entrepreneurship

🌱 Embracing feedback for growth

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πŸ“„ Show notes:

[00:00] Introduction

[02:03] Rob on his 2007 YC journey

[03:52] Introduction to entrepreneurship

[06:46] Lessons learned from a failed pivot

[08:49] Surviving a startup setback

[10:55] Key learnings and unlearning in transitioning to bootstrapping

[12:15] The London's cheapest startup co-working space

[15:00] Building an agency business

[19:33] The Mom Test Book

[20:26] The growth of the Mom Test

[22:00] The process of publishing the Mom Test Book

[27:26] Knowing when to quit

[28:45] The development of Rob's books

[30:15] How to deal with feedback

[34:41] Selecting projects strategically

πŸ—£ Mentioned in the show:

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

Georgia Institute of Technology | https://gatech.edu/node/1

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

BBC | https://www.bbc.com/

Sony Pictures | https://www.sonypictures.com/

MTV | https://www.mtv.com/

Golden Handcuffs | https://en.wikipedia.org/wiki/Golden_handcuffs

Bootstrapping | https://en.wikipedia.org/wiki/Bootstrapping_(statistics)

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

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

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

The Lean Startup | https://theleanstartup.com/

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

Useful Books | https://www.usefulbooks.com/

PBS | https://www.pbs.org/

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

Thinking in Bets | https://amzn.to/44NWiQc

Angela Duckworth | https://angeladuckworth.com/

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

Alice Bentick | https://alicebentinck.com/

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

Full episode transcript below

πŸ‘€Connect with Rob:

Twitter: https://twitter.com/robfitz

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

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

πŸ‘¨πŸΎβ€πŸ’» 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.

🐣 Twitter: @Delikwu / @itstheknowledge

🌐 Website: https://www.davidelikwu.com

πŸ“½οΈ Youtube: https://www.youtube.com/davidelikwu

πŸ“Έ Instagram: https://www.instagram.com/delikwu/

πŸ•Ί TikTok: https://www.tiktok.com/@delikwu

πŸŽ™οΈ Podcast: http://plnk.to/theknowledge

πŸ“– Free Book: https://pro.theknowledge.io/frames

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πŸ“œFull transcript:



Rob Fitzpatrick: 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. 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 interested. 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.

This week I'm sharing part of my conversation with Rob Fitzpatrick, who is the author of three awesome books, including The Mom Test and Write Useful Books, both of which are among the most universally recommended books for early entrepreneurs and non fiction writers.

Both of those books were actually recommended to me before I even met Rob, so it was actually really great for me personally getting to sit down with him and ask him a bunch of questions about some of the points mentioned in his books.

So this is a bit of a [00:01:00] throwback to an earlier conversation that we had, but you're going to hear us talking about Rob's journey going through Y Combinator in 2007. So one of the really early cohorts of YC in San Francisco, you're going to hear us talking about Rob's lessons from trying a startup and failing and having to pivot multiple times. We talk about some of the key lessons for bootstrapping that he's learned across his journey. We talk about his process for writing The Mom Test. And knowing when is the right time to quit and when is the right time to keep going as an entrepreneur.

And then finally we talk about what the process really is for being able to create something that people love, being able to create a product, being able to create a book, whatever format that takes. Rob has a really unique process for developing that and you're going to hear us talking about that in this episode.

And you can get the full show notes, the transcript and read my newsletter at theknowledge.Io. And you can find Rob online on Twitter @RobFitz.

Now, like I said, if you love this episode, please do share it with a friend and don't forget to leave a review wherever you listen to podcasts.


Rob on his 2007 YC journey

David Elikwu: You were in YC in 2007 and I think to this day that is still one of the hallmarks of 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. So, you know, we Still knew it wasn't easy to get into, 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 [00:03:00] 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. Like, you know, 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 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.

Introduction to entrepreneurship

David Elikwu: I think you touched on something that a lot of founders find where when you start a venture backed business, when you [00:04:00] 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 be, like a bit more thoughtful rather than just kind 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 [00:05:00] 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. But 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. 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 [00:06:00] 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. We did it and I got one of my, I got my favorite teacher to like quit. Well, he was like the head teaching assistant. I got him to quit and join the company. One of my other buddies dropped out 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.

Lessons learned from a failed pivot

David Elikwu: And so you, 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 [00:07:00] 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 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 custdev, 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 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. So we chose these industries we were selling to, like the entertainment industry, we're selling to music studios, music [00:08:00] 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 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.

Surviving a startup setback

Rob Fitzpatrick: 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 [00:09:00] 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, cause 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 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 me, they go, 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. 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 [00:10:00] till like one in the morning, cause 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. Once 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 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, important failure for me.

Key learnings and unlearning in transitioning to bootstrapping

David Elikwu: I'm interested in moving to bootstrapping and also I think you're working on a lot of like [00:11:00] 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, I guess, 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 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 like, it's not gonna turn around in a month, right? And at a certain point you need to draw the line. And like, 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.

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 [00:12:00] 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.

The London's cheapest startup co-working space

Rob Fitzpatrick: 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 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 like, 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 like 30 people, the whole like [00:13:00] 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 you know, 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 like 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 tenant showed up. I didn't have like a 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, I joined a boxing gym, which was a way better idea cause that a 50 quid a month or whatever was worth it. And I got to shower there each day. 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 [00:14:00] 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 cause 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 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. Cause 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. 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 [00:15:00] money. It was fun.

Building an agency business

Rob Fitzpatrick: 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 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. 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 [00:16:00] 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 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 [00:17:00] closed a $7 Million deal in the Middle East to basically do education for the whole country, this big four year program. 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, and basically feed all the money back into the local entrepreneurship ecosystem. Two of us didn't want to do 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, you know? 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, cause if you're manufacturing to manage quality, you really need to be in the [00:18:00] 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 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.

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?


The Mom Test Book

Rob Fitzpatrick: 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 [00:20:00] 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, like, for that type of person. And so I was like, oh, there's a cool little niche here.

And so I 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.

The growth of the Mom Test

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, [00:21:00] being a digital nomad is awesome, but I don't feel good 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 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, cause 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.

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 [00:22:00] books are so hard to sell.

The process of publishing the Mom Test Book

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 presence that you'd been building?

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

David Elikwu: Yes, yeah. There's a few questions to unpack. One is the original inertia to write a book, cause 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 [00:23:00] 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 polished. You know, 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 was 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 like, he's kind of 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 [00:24:00] 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. 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, I 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 kind of like you trick yourself in a good way with the Sunk Cost Fallacy. Cause I probably only [00:25:00] spent like 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 away. And you know, you work it and that trick keeps working. And At some point, 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, I think I changed it now, but in the original intro, the intro was almost saying like, 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 like, 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, my best guess of how it works. And I thought maybe it would be helpful [00:26:00] for a couple people.

As I approached launch data, it was really scary. And what finally pushed me to get it out the door 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 like 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 [00:27:00] something unless I've made sure that those ideas work for other people. I'm doing it now. I'm writing about outcome-oriented 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.

Knowing when to quit

David Elikwu: I'm really interested in, you've kind of 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 [00:28:00] founder, you have to be gritty, you have to keep going effectively everything 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.

The development of Rob's books

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 [00:29:00] signals about whether it's used by your readers, right? 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, out of 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. I've done some beta reading where I'm like, I cannot fix these problems. 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 good author to make it come across. So I would never give up after the [00:30:00] 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, that was a fun, like three months writing a manuscript.

How to deal with feedback

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, 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 good.

What's usually true or closer to the truth is that when you talk [00:31:00] 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, 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 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 [00:32:00] 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, 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 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. [00:33:00] 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 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 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, beep, 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. Maybe [00:34:00] 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 of 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, when customers tell you things, that's not the data, that's not the treasure. That's the metal detector going beep, beep, 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.

Selecting projects strategically

David Elikwu: Yeah, So on the flip side, how do you decide which projects to start? You know, the question in my mind is do you 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 [00:35:00] 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.

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 sort of 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 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 it is no longer a good fit for me. It's harder with a team, right? Cause 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 [00:36:00] 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, cause 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 cause 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 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. 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 [00:37:00] 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 of 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 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 and 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 [00:38:00] 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: 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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