Andrew Lynch: Confronting Uncomfortable Truths

The first time I communicated with Andrew, he gave me some good advice. ​

I didn’t know it at the time, but he had just been fired from his role at a startup called Book in a Box. He was experimenting with the possibility of consulting and copywriting.

He posted in the Choose Yourself Facebook group with the following offer: post a link to your website and I’ll give you five ideas to improve it, for free. The response he received surprised me, and I suspect, surprised Andrew too.

I posted the link to my blog, Phronetic. Andrew responded and gave me some kind words. Then he told me to start building an email list. At that time, I’d just finished Seth Godin’s Permission Marketing, so I understood why I needed a permission asset. But I was stalling. Andrew’s words were like a skydiving instructor. They helped me make the jump from procrastination to action.

Since then, Andrew has given me lots of help. I bugged him with questions about self-publishing my first book. I’ve asked him about Cal Newport and other thinkers we’ve both read. I sent him drafts of a project which I’ve since abandoned. He sent me a story called A Message to Garcia when I was struggling with writing.

If I was to slap a ratio on it, I’d say that for each piece of guidance that I’ve received and acted on from Andrew, I’ve ignored five more. So naturally, I felt both excited and nervous to talk to him for the first time. I know he’s smart, accomplished and that he’s spent time around people I admire. But my nervousness was unnecessary. 

Andrew is honest, patient, determined, and most importantly, receptive to diverse ideas and perspectives. I had a lot of fun talking to him, and I’m sure that this is just the first of many fruitful conversations. I hope you enjoy it as much as I did.

MATT: Let’s start with your transition from a corporate role, to Book in a Box, and back again.

ANDREW: Sure, let’s do it.

MATT: I’ve got an idea of how it happened. But I don’t know where you came from and how you made the connection with Tucker [Max, co-founder of Book In A Box]. 

ANDREW: I’ve been a big fan of Tucker’s books since about 2006 or 2007. I found his writing and books online and thought he was really funny. I thought he was a very good writer, and obviously, a very intelligent guy. I followed him a little bit then.

Then, as his movie was coming out in 2009, and I was a full time student in Leeds, I sent him an email. I was pitching him for a job saying, “I can do this and this and this. I’m happy to do it and I’ll work for you for free.”

He said no at the time.

MATT: When you look back on that email, do you cringe? Or was it well done?

ANDREW: No, not really. It was a reasonable pitch. I probably… I didn’t tailor it enough to him. My pitch was like, “give me a job. I’m smart.” He came back to me and said something like, “instead of coming to me with a handout like everyone else does, think about how you can solve my problem. Or what you can do for me. Rather than saying, ‘I’m a smart guy, give me a job. I will prove it by being smart and doing smart things,’ think about your audience a little bit more.”

A guy like Tucker, even then, would get tons of emails like that every week. I don’t know about these days, but I imagine he still gets that a lot.

I pitched a couple of other people with the same thing. I ended up doing a bit of work for Ramit Sethi of I Will Teach You to Be Rich. I helped him with his book launch and then he referred me to this author from Stanford who was writing a book. I did a little research on his book, but nothing huge.

I graduated a couple years later and started working full time in a normal, corporate graduate job.

MATT: That was in finance.

ANDREW: Yeah, I was a trainee accountant. Then, I think it was late 2013, I got an email from Tucker replying to an email from 2009. He said, “Hey, how come you stopped writing on your blog? I used to read it and I thought it was pretty good. It was one of the few I subscribed to in my Google reader.”

That was weird. But we started going back and forth. I mentioned my career and how I felt about it and again, I made a pitch to him. “If you have any work you want me to do, I’m happy to do it.”

Actually, I think I did it a bit better and said, “Do you know any authors who are writing a book? I’d be happy to do research, writing, whatever, for them.” It turned out he was in the middle of writing a book and starting this new website. It was his book about dating advice. It was called Mate and the website was The Mating Grounds.

So I did some research for his site and helped him manage the podcast. I was doing that for about five months for no money at all, and then for another few months for a hundred dollars a week on the side of my day job. 

So I was working nine to five, coming home, going to the gym, having dinner, tidying up, and working on Tucker’s stuff from ten till midnight or one AM. I did that five days a week. It was pretty hard.

Then, end of summer, autumn 2014, Tucker and Zach started Book in a BoxIt started to take off. By the end of the year, they had more work than just the two of them could handle so they asked me to come on-board full time, starting January 1st 2015. They flew me to out to Austin and I stayed for three months, which is exactly how long you can be there without having to get a proper visa. 

So I basically lived with Zach in an apartment building next to Tucker. The three of us would get together every day for an hour, discuss stuff, and then go back and do work. That’s what it was like for a few months. Then I came back to the UK because my girlfriend, my family and everything were here, and I started working remotely.

MATT: So, your average day. Was it full-on like startups are made out to be? Eighteen hour days? Or was it more laid back and well managed?

ANDREW: It wasn’t crazy to begin with because my job was split. On one hand, I was improving and building out the processes. On the other hand, I was managing all the client projects from start to finish. 

That wasn’t too bad for the first few months because we were pretty new. We didn’t have that many clients. But as the year went on, we got busier and busier and busier. So by the end of it, I was flat out. Getting lots of emails every day. Going back and forth with clients and freelancers. It was busy, but it wasn’t crazy, manic, twenty hour days like the stereotypical startup thing.

MATT: You were Publishing Manager right? That was your official title?

ANDREW: Yeah, exactly.

MATT: That entailed managing relationships, developing the processes, a bit of everything really?

ANDREW: Yeah. It was my job to shepherd the author through the process. I would hand them off to an outliner. Then, when they were done, they would come back to me and I’d match them with an editor. Once they were done with that, I’d help them through their cover design. I’d help them with that and then we’d get it proofread, get the interior laid out, formatted for Kindle and everything like that.

MATT: So the end of 2015 comes and you had the… Well, the first I heard about it was when you wrote that article about being fired on Christmas eve.

ANDREW: It wasn’t that bad. It was the day before Christmas Eve.

MATT: I read it. It was very open, honest stuff. When was the turning point?

ANDREW: Towards the end of 2015. Maybe mid-autumn. I started to get pretty busy. I was working remotely, on my own. It wasn’t fun at all. I don’t enjoy it and I’m not good at it. I’m quite sociable and outgoing. With the time difference, I’d be up and working at nine or ten and no one else from the company would even be online until one or two in the afternoon. Even then, I’m spending my whole day talking to them on email, or Slack, or occasionally, on Skype. And I wasn’t really enjoying the work. To be honest, I wasn’t that good at it either. There’s a reason I trained to be an accountant and I’m now an accountant. I’m good at it. I know it well. I enjoy it.

Publishing and writing? I can write well. I like that. But I don’t really like managing creative projects. I wasn’t really good at it. I didn’t enjoy it. And I wasn’t getting much in the way of management or feedback either. So I just fobbed off my work. I tried to do the bare minimum to avoid getting fired. Although it turns out I missed that goal slightly.

Basically, I didn’t enjoy it and I wasn’t good at it, but I didn’t want to say anything. I really liked the people I was working for and I liked the company. I assumed that if I went to Tucker and Zach and said, “I’m not very good at this job. You know that and I know that. I shouldn’t really be doing it,” presumably, that would be me out of the company. There wasn’t another job in the company I could do. There wasn’t a need for an accountant or finance analyst or anything like that. I think that was the reason I didn’t say anything.

So I just let it build and then eventually, Tucker and Zach made the call, which was absolutely the right call. I think Tucker has since written this in an article, but I probably shouldn’t have been hired in the first place. I was really grateful that I was and I really enjoyed working for them. I like those guys and I’m good friends with them still. But that particular job, at that particular time, just wasn’t right for me.

MATT: The transition back into more traditional work, was that difficult? Or was it a relief to go back into a more normal environment?

ANDREW: Yeah, in some ways it was a relief. 

I had a period in-between jobs where I was doing some freelance copywriting. I got three or four clients and I probably could have built it into a sustainable business. But I realised I didn’t like that either. I like being around other people. I like the social interaction and engagement. 

So when I got offered a full time job in a management accounting role for a company here in the North East, I was more than happy to take it. I’m really enjoying the job, I really like the company and the people I work for.

I think there’s a lot to be said for enjoying a job because you’re good at it. It’s fun and enjoyable to be good at something. I was in a role where I was floundering every day, not really knowing what I was doing, hanging on the by the skin of my teeth. Now I do a job where I can perform well, where I can excel. It’s a lot more satisfying.

MATT: How do you find the balance between pushing right to the edge of your capabilities, and actually being able to exercise control? How do you make sure you’re still pushing yourself?

ANDREW: I’m still challenged in my current role. I’m doing stuff I haven’t done before. I’m still learning. But it’s learning within a certain sphere. It’s learning about accounting, finance, and how to manage a business from a financial point of view. It’s learning and pushing myself within a certain circle of competence

Now contrast that with what it was like at Book in a Box. I was being pushed out of my comfort zone, doing things I’d never done, but it was helping someone to get a really good book cover, or trying to find six really good proofreaders. I didn’t know how to do that.

In essence, I did learn new things, but it was things I didn’t really care about. If I never learnt how to hire a book cover designer or a proofreader, I wouldn’t care. 

The stuff I’m learning now and pushing myself on now, I want to know more about. Does that make sense?

MATT: Yeah. It’s like, all that stuff was cool, but it’s not really relevant to what you want to spend your life doing.

ANDREW: Right, exactly. If someone said to me, “Oh, you should go and be a chef at a fancy restaurant. You’ve got to push yourself and get outside your comfort zone,” I wouldn’t have a clue what I was doing. I’m not good at that and I have no experience in it. I’m sure I could learn to be somewhat capable at it. I’m probably smart enough to be reasonable at anything, but there’s tonnes of stuff I don’t enjoy doing and don’t want to do. 

Actually, take that back. I would never even be a reasonable chef. I would be awful. But there’s a reason I don’t do that for a living. I don’t want to. I have no interest in it. Even if you tried to teach me how to do it, push me and make me learn new things, I wouldn’t really care.

MATT: So how do you find, not necessarily what you enjoy, but… I’ll step back a little bit. I applied for a role at Book in a Box a while ago. I didn’t get in and Tucker ended up giving me some advice. He told me to focus on where my skills overlap with what the world needs.

But how do you find that point? How do you find the balance between doing stuff that you enjoy, and making sure the stuff you enjoy provides value for other people?

ANDREW: That’s a good question. Honestly, I don’t know the answer. It just so happens that the thing that I enjoy and I’m quite good at is accounting and finance. There’s plenty of those jobs out there. As opposed to what you’re doing, which is a little more unconventional, where you’re having to cut your own path. It does require experimentation and trying to focus on what the market wants, instead of what you want.

I tried to do it when I got laid off from Book in a Box. I tried to start my own freelance copywriting business because I thought, “I quite like writing. I’m good at it.” And copywriting is a nice way to make money because people know they need to spend money on good copy. Clients are willing and able to spend that money. There’s marketplaces out there, like Fiverr, Upwork and Elance where people are posting jobs. It seemed like a perfect market to me.

Like I said, I got three or four clients and realised I could be a decent copywriter. But it would be boring to me because I’d be sat at home, alone on my laptop all day, instead of out and interacting with people.

Doing any kind of work, there’s always certain parts you enjoy more than others. You just have to be very honest with yourself about what that is for you.

One of the things I thought I would love about Book in a Box is working remotely. Having the flexibility to sleep in when I want to sleep in, work late when I want to work late. That’s generally what I prefer. I prefer to stay in bed in the morning, but I can work until one or two.

It turns out that’s really difficult when you have a girlfriend who works nine to five, and wants to spend time with you between the hours of six and ten. She doesn’t want you to be working all the time. She doesn’t want you to be asleep when she’s awake. 

Realising that the reality of life conflicts with that ideal forced me to be honest with myself and go, “You know what? I really, actually want a nine to five office job.”

That doesn’t mean it’s a boring job. It doesn’t mean I’m a corporate drone. It just means I have a place of work that I go to, with other people that I interact with. I’m perfectly okay with that.

MATT: A couple of the groups we’re both members of—Choose Yourself, The End of Jobs—have this tendency to lionize the entrepreneurial lifestyle.


MATT: Is that sort of thinking something you subscribed to before you started working at Book in a Box, but changed your mind about?

ANDREW: Yeah, I was definitely drinking that Kool-Aid. One of the people both you and I admire is Ryan Holiday. I saw my path working for Tucker as being able to do what he’s done. Start my own company, have my own clients, do consulting, be remote, write when I want to, publish books, speak all over the world. 

No doubt, all that works for Ryan. I’ve never met him myself, but I know people that know him, and—he wrote about this in his latest book—he’s a workaholic. He’s pretty quiet, introverted and focuses a lot on his work. But that’s not who I am as an individual. It took me going through that testing phase, trying out remote work and freelancing to realise that.

Going back to your question, some of that lionizing of the entrepreneur lifestyle and the location-independent, passive income businesses is bullshit. 

I think I resisted the fact that I quite like a nine to five because it conflicted with the idea of who I wanted to be in my head. This online, remote entrepreneur who makes lots of money in his twenties. I know some of those guys as well. They’re single. They work eighteen hours a day. They work alone at home on their laptops. Every photo they put on Instagram is filtered and takes twenty hours to get right. 

None of the stuff you read online, none of it’s a real reflection of life. At best, you’re seeing the edited highlights that someone wants you to see. 

The other thing to remember is that there are tons and tons of successful entrepreneurs or business owners who don’t earn money online and aren’t location independent. They have a real, physical business with real customers, with real staff, with inventory, with cash in the bank.

MATT: Not every successful person is the founder of a SaaS company.

ANDREW: Exactly. The choice for entrepreneurs isn’t between starting a location independent, passive income business that sells video courses or starting the next Facebook. There’s ten thousand other ways to do that kind of thing.

Right now, I’m happy accepting that I have a load to learn. And for me, the best way to do that and the most enjoyable way to do that, is to have a job with other people. 

That kind of entrepreneurial material did have a big impact on me. But it took me a while to be honest with myself and realise that it’s okay not to be like that.

MATT: I’ve found that difficult as well. Only in the last two or three months have I started to come up for air and realise what I don’t want to do or be.

It’s very difficult to get that separation, to look at where you are from a detached perspective. Have you found an easy way to have those conversations with yourself?

ANDREW: It wasn’t entirely me. I had a couple of good friends. One guy in particular, Kevin, that I used to work with at Book in a Box, he and I are quite similar in a lot of ways. I’ve talked a lot about this sort of stuff with him. He’s talked about his own issues and how he’s working through them with me. Having someone like that, someone you can trust, can speak to, who is going to be honest with you is so useful.

Kevin helped me figure this stuff out. He said, “Why don’t you just go and get a job? You’d be good at it and it’s clearly what you want. You could scratch about trying to be an entrepreneur or freelancer and make money that way. Or you could just go and earn much more money doing something that you enjoy with people that you like and get on with.” When he put it like that, it was a no-brainer.

MATT: One of the things it took me a while to figure out, especially when it comes to entrepreneurship, is that the important thing isn’t going out and going it alone. It’s the underlying skillset that you have.

ANDREW: Yeah, totally.

MATT: You need valuable skills before you go out and do your own thing. 

The route you’re on, starting in corporate, joining a start up and then going back to a more traditional environment, it doesn’t rule out anything in the future. Where you are, in a traditional environment, you’re still building career capital, positioning yourself and maintaining entrepreneurship as an option.

ANDREW: Exactly. It’s not a binary, either-or thing. Doing one doesn’t mean you can never do the other. 

My first company, NFU Mutual [a large insurance company in the UK], they have over a billion pounds in turnover and nearly four thousand employees. That was a big company. Book in a Box was three of us sat around a dining table talking. This company that I’m working for has about ten million pounds in turnover, but it’s still fairly small.  I think there’s two hundred and fifty employees. But I talk to the owner and the managing director most days. I work directly for the finance director. 

It’s small enough that I can see the inner workings. It’s small enough for me to have an impact, but big enough to have a role for me that is something I enjoy and want to do. I can learn what I want to learn and get involved in what I want to get involved in.

I can also learn about entrepreneurship. The guy who owns the company started it from scratch ten years ago, so there’s plenty I can learn from him. The guy who runs it now is a very, very good, very capable manager. There’s plenty of things I can learn and plenty of people I can learn from.

So yeah, there’s shades of grey between big corporate behemoth and tiny start-up.

MATT: On a more practical level, for me, the idea of income streams and single points of failure is one of the most persuasive arguments for entrepreneurship and doing your own thing. 

Having more income streams makes you a lot more robust. How do you reconcile that fact with deciding to go for a single job where you have a single, salaried income?

ANDREW: I think we’re talking about the same book. Having one source of income is fragile. And one of the ways you get around that is by having a decent amount of cash in the bank. I know that if I lost this job today, I would be fine for at least a couple of months. 

But obviously, there’s huge benefits to having multiple streams of income. At the moment I have my book, The Daily Practice Journal, which is available on Amazon and earns me a good three or four pounds a month. I have some investments that pay a little, but not a lot. And I’m looking at side projects I can do too. I still have time between the hours of six and ten when the girlfriend’s away. But yeah, having one job and being a slave to one boss does add a bit of risk.

At the same time, if you can do a great job and crush it, that goes some way to mitigating the risk. You might not see your income increase as quickly as if you were the owner of a company growing thirty or forty percent a year, but you do have a solid income. You can put some aside and build a little capital to start investing in side projects.

I think that’s where I’m up to at the moment.

MATT: So what’s your biggest obstacle right now? What are you working on?

ANDREW: What I really want to do is develop another income stream. I’m limited in terms of time, but I have a couple ideas just sitting on the side. My biggest obstacle is trying those out, testing them, seeing what works and what doesn’t.

I’m at a stage where I’m still quite young. I have a lot of time ahead of me, so now would be a good time to invest and start building some wealth that way.

The other thing I’m struggling with is trying to get into good physical shape. When I was sixteen or seventeen, I was working out religiously three times a week, running ten or fifteen miles a week, no problem. I was eating pretty clean. I was lean. I was in very good shape.

Now that I’m twenty seven, nearly twenty eight, and working at a desk job, driving an hour each way every day, I spend a lot of time sat on my arse, so I’m not in as good a shape as I want to be. 

I’m working on the big compound lifts and trying my hardest to eat right. But getting the diet right and the discipline is the hardest bit for me.

MATT: You’ve got a forty five minute commute to and back from work?


MATT: Do you make use of that time? I know a lot of people are fond of podcasts, audio books, and that sort of thing.

ANDREW: I do exactly that. Ninety five percent of the time I’m in the car. I have a few podcasts and audiobooks I listen to regularly. Some of them are “productive” podcasts. The Tim Ferriss Show or Freakonomics or Jocko Willink’s podcast. Other ones, like the Guardian’s Football Weekly, the Football Ramble, are just entertainment.

MATT: What audiobooks have you got queued up at the moment?

ANDREW: I just finished listening to Ready Player One by Ernest Cline. Have you heard of it?

MATT: I haven’t no.

ANDREW: It’s really good. And it’s narrated by Will Wheaton which is cool. The basic premise is that there’s a big virtual reality world called The Oasis, and the guy who created it is, far and away, the richest guy in the world. He’s like the future Bill Gates. This is set in 2030, 2040. Then he dies and, in his will, he leaves his entire creation, this incredible virtual world as well as all of his wealth, to whoever wins this contest.

It’s just following a guy who is competing in this contest. It’s really, really good. Someone described it as The Matrix meets Charlie and the Chocolate Factory.

MATT: Does that count as one of the “productive” ones?

ANDREW: No, not really. That was just good fun. 

I think one of my problems is that I read and consume too much non-fiction. Sometimes, it’s nice to read for pleasure and for the fun of it, rather than thinking I must be highlighting, tabbing pages, and learning a lot. 

That said, another audiobook I have is The House of Morgan by Ron Chernow. It’s a history of J.P. Morgan bank from when it was founded to the modern day. He also wrote that really thick biography of John Rockefeller.

I’ve got Genghis Khan and the Making of the Modern World by Jack Weatherford. I’ve got that in hardback, but I quite like the audio as well.

Another is Robert Greene’s 33 Strategies of War. Again, I’ve got the physical book, but I quite like listening to it. 

I’m listening to one at the moment called The Warren Buffett Way. I’ve read a couple biographies of Buffett, but this one is a little different. It focuses more on his investment and business strategies, as opposed to his life and biography, which would include stuff about his investment style but not focus on it specifically.

MATT: What have you changed your mind about in the last year or so? Has there been a seismic shift in your thought about something? Or has there just been lots of incremental developments in your ideas about different things?

ANDREW: It’s similar to what we were saying earlier.

When I started working for Book in a Box, my mindset shifted to thinking that anyone who works in a standard, corporate office job is an idiot and a drone. And anyone who works for a startup is a genius, a smart guy, is going to be very rich and wealthy, and is engaged in much more interesting work, much more fulfilling work. That was a completely false dichotomy.

It’s perfectly possible to be happy and fulfilled while working in a “normal” job. It’s perfectly possible to go to work from nine till five and find fulfilment from five thirty till ten thirty. Whether that’s with your hobbies, your family, your kids, fitness, anything like that.

The other biggest thing I’ve realised in the last six or twelve months is that I’m probably ready to get married, have kids and start a family. I think I’m mature enough, capable enough and financially sound enough to cope with it all.

MATT: When you shift into that stage of your life, it completely changes your tolerance for risk. You can’t afford to be as aggressive when you’re experimenting. Is that something you’re conscious of? Is that something that bothers you? 

ANDREW: I had this conversation with some people from NFU Mutual when I was working for Book in a Box. They still work for the insurance company that we worked for when we graduated. They said to me that working for a startup seems really, really, risky. I said, “Why is it risky? Why do you think that?” They said, “Well, because it might not work out. Who knows what’s going to happen?” I said, “No, but if this job doesn’t work out, I’ll have the experience and the skills to go and find another one. If it does work out, but not incredibly well, then I’ll be at a good job making good money. If it works out incredibly well, then fantastic. I can make a lot of money, be happy, then go and do my own thing.”

None of the possible outcomes were bad. It was uncertain, but not risky. I think it’s important to differentiate between the two. 

I think you’re right about having a family. If I have two kids, a wife and a mortgage, I’m not going to quit my job tomorrow, take my life savings and plow them into getting a new company off the ground. 

But on the flip side, it will probably encourage me to be a little bit smarter, to only jump into something once I’ve tested it and know it’s going to work. Or at least have a good idea that it will.

Maybe I invest a thousand pounds in five different ideas, rather than wasting fifty grand and remortgaging my house to start a company. There’s different ways around it. Entrepreneurship and starting your own business doesn’t mean spending lots of money and taking lots of risks. 

It’s like stepping stones. Maybe you start small with an online course or product. Dropshipping, a market stall, a food truck, whatever. Something that doesn’t cost a lot of money to get off the ground. It will never make you a multi-millionaire, but you might be able to turn £1k into £5k.

Then you find another thing. Maybe you want to open an online store with a physical product you’re getting manufactured nearby. So you take three grand, invest it in that and turn into ten or fifteen.

Instead of putting all your money on black and rolling the dice—those are two different games—you can do it that way. 

MATT: Is stepping out and doing something on your own not off the cards then? Is that something you’re still set on, or just an option at the moment? If an opportunity comes up or a gap in the market opens up, are you going to jump on it? Or do you see yourself being where you are now for the considerable future?

ANDREW: I think I’ll be where I am now for at least another six months or so. Probably more than that. Probably a year, eighteen months. 

I still have a lot to learn from the people I’m working with at the moment. That said, if an incredible opportunity came along tomorrow, and I talked about it with my girlfriend and family, then I may well jump on it.

I’m not actively looking for something else or another opportunity right now. It would need to be the right opportunity at the right time. But I’m certainly keeping my eyes and ears open.

MATT: In any job, one of the biggest things is getting feedback on your actions and the things you do on a day-to-day basis. I’ve never been in a traditional environment at a normal company. Is that feedback something that has to be embedded in the culture? Do you get it where you are now? Or do you have to push for people to give you that?

ANDREW: I think it depends on the culture and the company. Even more than that, it depends on your immediate boss or line manager. 

But if it’s not coming to you, you have to go out and ask for it. You have to elicit that feedback. One of the things I’ve said to every person that’s ever managed me is that if you see me doing something particularly well, that’s great and feel free to compliment me or say well done. But more importantly, if you see something you think I should be doing differently or I can improve on, please, please, tell me as soon as possible. If you think you’re going to offend me, don’t worry. Just say it as frankly, quickly and as honestly as you can because that’s how I’m going to improve.

More often than not, you have to ask for that type of feedback. Most people aren’t as comfortable giving negative feedback as they are positive feedback. You really have to be conscious about seeking that feedback.

The other thing to remember with you and I, when we’re talking about development and mastery, is that we’re only in our twenties. I’m nearly twenty eight. You’re a couple years younger right?

MATT: Yeah, twenty five. 

ANDREW: Assuming you work until you’re sixty five, which may not be true, it might be less, it might be more, you’ve still got forty years left of a working career. There’s a lot you can learn in forty fucking years. There’s a lot you can improve on. There’s plenty of time. There’s no mistake too big that you can make that you wouldn’t be able to recover from. There’s no opportunity so great that there will never be anything like it again.

Part of what I’ve learned is to not worry about that stuff so much. Yes, still be conscious of it and driving towards it. But I’m not thinking, “Fuck. Why have I not published three books yet? Why have I not started two companies? There are other people my age who have done that.”

Yeah, there are. There are also plenty of other people my age who are still fucking idiots, and either unemployed or working awful jobs that they’ve been in for five years and will be in for another twenty years. 

They don’t know any different, they don’t know how to develop and seek feedback. They have the wrong attitude. Stuff like that.

There’s different ways to look at it. I’m very conscious of feedback, I do ask for it and seek it where I can. But at the same time, I’m not furiously trying to tick objectives off a sheet just to try and get to the next level.

MATT: What does a typical day look like for you?

ANDREW: I leave the house about eight and get to work at nine. Then spreadsheets and email until five basically. The odd meeting here and there, but what I do is very desk based, office based. There’s a little bit of travelling and going out to sites to visit the guys who manage our contracts. But mainly I’m sat at a desk, working through accounting software, doing lots of Excel, lots of formulas and macros. Stuff like that.

Describing it like that sounds boring. I quite enjoy it. I like it and I’m good at it. I’m happy with it.

Funnily enough, a guy on Reddit who does basically what I do—he was a chartered accountant—automated a ton of his work in Excel, in macros and formulas. He went from that to database management and then started his own company. He does what I do but on a much higher level.

MATT: People have this perception of accounting work as something that’s very dull, boring and doesn’t give you a chance to exercise your creativity. Do you find that’s where the creativity comes in? Figuring out how to optimise that stuff and work out the most efficient way to do things?

ANDREW: Yeah, exactly. Tonnes of what I do is in Excel, and you can’t really call it Excel programming, but it’s one level removed from that. It’s one step down.

It’s creating a really effective, efficient process in Excel that anyone can use, is pretty fail-safe, and is easily updatable. It’s not far off programming. You are creating something new from scratch. There’s a decent amount of creativity in that.

The other part of accounting that I find interesting is that it’s a business superpower. We have marketing and sales and customer service, but we do it all to make money. It’s basically my job to make sure that we are doing that.

Within that, it’s my job to save a couple thousand pounds here or make a couple thousand pounds there. Getting involved at that level across a whole company is really, really, interesting. I love it.

MATT: I was looking on your website a while ago. It said somewhere on there that you are a process improvement specialist. Is that what you do? Take the big picture view of a process, figure out the constraints, the limits in it and make it better?

ANDREW: Yeah, that’s a big part of it. Everything I know about process improvement, I learnt from my first job at NFU Mutual. There was a guy there who used to work for McKinsey. I think he now works for KPMG, doing a project with McClaren. It’s either McClaren or Mercedes, but they’re looking at how they can use data, analytics and processes to improve the performance of their Formula One team. He’s a really, really smart, interesting guy.

It’s not just, “How can we make this process more efficient or cost less?” It’s about asking what you’re actually trying to accomplish with a given process and why it exists. If it’s a useless process that doesn’t add any value to anything, you can just stop doing it. There’s no point in having a really efficient process that doesn’t do anything.

You can go a step further. Normally, what you’d do is sit and map out what’s called a value stream, which is the whole process from start to finish, the way this process delivers value to the end customer. That can be a customer who is paying you money, or it can be an internal customer. A lot of what I do, in my job, is delivering value to internal customers. Telling people how they’ve done compared to their budgets and forecasts.

You’ve got to think about what exactly it is they want, and then ask, “How do we deliver it to them?” Create a big process map, a value stream, and look at what steps are and aren’t necessary. Can you move them around in a different order to make it easier? Can it piggyback on a different process? Are you delivering this gold-plated, super duper fancy thing, when, in actual fact, the customer would be happy with something simpler, quicker and easier? And looking at the constraints. Asking why they exist. Are there good constraints there? Do we need them? 

A lot of that, pretty much all of that, I learnt on the job, in my first job. 

Accounting, particularly in a smaller company, lets you see what’s going on in lots of different areas of the company. You can see into all these silos. You can often see things that people working in those individual areas can’t.

A really good example is that, at the moment, we run a lot of different contracts for clients all around London.

MATT: What’s the firm’s primary business?

ANDREW: Facilities management. Say you’re a marketing agency. You might have a big office, but your expertise is in designing and delivering marketing programs. You just want a nice office to work in. Well our company, for a fee, will supply all the receptionists, the security guards, the cleaners, the maintenance and fix anything that goes wrong with the building. You can just hire us to do everything for a monthly fee. We’ll take care of it all. 

Saw we do that for ten clients in central London. Each one of those guys running those contracts needs a certain number of people on reception, a certain number of cleaners et cetera. 

A lot of the time when someone can’t make it in or they need holiday cover, one of those guys will phone up a temp agency. Every single person, every single client and all of these managers in London will phone the same agency.

But from where I’m sat, overlooking the whole thing, seeing everything, I can say, “Okay, why don’t we just have one or two cleaners who are on call? They can go and work at any one of these individual contracts as and when we need them to. We can then pay that person ten pound an hour as opposed to paying an employment agency fifteen pound per hour, which saves us a lot of money when we’re talking about a hundred plus hours every week.

If you’re at the coal face on each individual contract, you wouldn’t see that. From our vantage point, being slightly less involved on each of them, we can see that and help make it better for the guys on site. They get a reliable source of labour. It’s better for us because it’s cheaper. And it gives some of our guys more hours and the chance to earn more money as well.

It’s things like that, that if you multiply by ten across the company, really allow us to make better money and have better processes.

MATT: It’s a very transferable skill set then. It transfers over to engineering and marketing and everything like that, but it’s all founded on being able to create and assess different processes.

ANDREW: That’s fundamentally what a business is. There’s this definition from The Personal MBA: “A repeatable way of producing and delivering a product to an end customer and selling it for more than it cost you to make it.” 

If you can do that over and over and over again, you have a business. If you can’t, then you’re a freelancer, an employee or you just don’t have a business.

There’s a couple of good books on this. One of them is called Work the System. It’s about this guy who bought a business—I can’t remember whether he bought or started it—and ended up working over a hundred hours a week. Doing everything himself. He realised he was spending all his time doing customer service or finance or marketing or sales, rather than building or hiring a team, or building processes to hand off to someone else. 

As a business owner or entrepreneur, it’s not necessarily your job to do sales or marketing or finance. It’s your job to set out how you want it to be done, build a process for it to be done and then hire someone to do it. Otherwise, you’re just building a job. 

It’s a fundamental business skill. Building, running and developing core processes.

MATT: I remember Derek Sivers talking about something similar. Probably a ton of other people have said the same thing. Entrepreneurship and building businesses is about making yourself irrelevant to the running of the company. If the company can’t function without your input, then there’s something fundamentally wrong with the way that it’s structured or designed to operate.

ANDREW: Yeah, absolutely. As the CEO of a company, you shouldn’t be answering customer service calls. Every decision shouldn’t need to go through you. If it does, then you haven’t built a self-sustaining organism.

MATT: You’ve had three or four major phases in your life. You’ve had university… Oh, that’s what I wanted to ask about. You paid your way through university playing poker. Is that right?

ANDREW: Yeah, to a certain extent. Obviously I had student loans, a little help from Mum and Dad. For day-to-day spending money, I played online poker.

MATT: I had a look through some of the bios of people at Book in a Box. Didn’t someone else do that?

ANDREW: Yeah. My friend, Kevin Espiritu. But I want to put it in context by saying that I made what could generously be called beer money. I won’t give you exact numbers, but I still have a job now. I don’t play professionally. Kevin’s five, six levels above me. He was very, very good. He was a much better player than I ever was. I think he played and paid his way through college.

MATT: It’s a different set up in the US. You actually have to pay your way. 

ANDREW: Right.

MATT: I know you’ve taken a lot from the work of Cal Newport. You found him through his books that are aimed at students.

ANDREW: Yeah, yeah.

MATT: I haven’t read them. But I’ve read So Good They Can’t Ignore You and Deep Work. How did those books impact how you approached your studies and learning?

ANDREW: In terms of studying, the biggest thing I took was exam prep. For any exam, I would sit down with a bunch of little notecards or flash cards. The kind that you and Ryan Holiday write quotes on.

MATT: The 6x4s, yeah.

ANDREW: For every module at uni, for every exam, for all the material I needed to know, I would write a question on one side of the card and the answer on the other.

I did a statistics course for example. So on one side, you’d have “Define standard deviation.” On the back, you’d have the definition. For each subject, I would have maybe fifty cards. Sometimes it was simple. Sometimes it was more complex. But I’d end up with about fifty cards and number them one to fifty. 

So you start at number one. You read the question and then you have to say the answer out loud to yourself. You flip the card over and if you get it right, great. You put it in one pile. If you get it wrong, you put it in a different pile. 

By the time you’ve gone through all fifty cards, you’ll have two piles. A pile where you got them all right and a pile where you got them all wrong. You pick up a pile where you got them all wrong and you start again. 

That does two important things. Firstly, you spend a lot more time studying the stuff that you struggle with, rather than the stuff you know really well. Secondly, having to verbalise the answer like that makes a huge difference in terms of recall and memory. 

Doing that, I found I could cut my study time by quite a lot and still do well.

MATT: Reminds me of a program called Anki. It’s basically a digital version of that process. That reminds me.

I don’t know if this was the same for you, but when I write out the 6×4 cards, I write them by hand, and it takes way, way longer. It’s so inefficient. But the inefficiency of the process is what gives it it’s value, because it forces you to interact with and handle the information more. Did you find that writing the flashcards?

ANDREW: I’m quite a visual thinker. If I’m trying to think through something, I’ll sketch out a diagram or a little table or a chart, or something which helps me think better than if I write it down. 

But I think you’re right. Note cards are the same. The act of having to write it down is beneficial.

MATT: Have you ever used the Feynman Technique?

ANDREW: No not really. I’ve used versions of it. In all honesty, I should probably use it for my current job, to make sure that I know I have my accounting down cold.

Accounting isn’t a book learnable subject. You can’t just sit down, read a few books on it and get it. You need to do it in practice. It’s like maths, you need to do it and practice it. Answer practice questions and have a teacher or someone grade you and assess how you’re doing.

But once you actually have that knowledge, something like the Feynman Technique could be a really good way to do that. Supplement it with a bunch of practice questions from accounting textbooks and you’d be super fluent in everything you need to know. 

I think that’s one of the big things, particularly in accounting. Everyone takes these exams in their early twenties and then puts their textbooks away for the next thirty years, and never looks at them again.

MATT: That’s the same in any discipline isn’t it? You do your initial training in your late teens or early twenties. Then you get into the job and the job itself is supposed to be enough to allow you to sustain an edge. To keep pushing you forward. But in ninety-nine percent of the cases, it isn’t.

ANDREW: You do MMA right?

MATT: Well, jiu-jitsu. I don’t do MMA. I don’t want to get hit in the face.

ANDREW: I imagine that, with jiu-jitsu, once you’ve learnt the basic positions and holds, they don’t just go, “Now, every time you come in, you’re going to fight someone. Then, at the end of the fight, that’s the end of the lesson. You have to go home. And when you come back, we’ll fight again.”

Presumably, you don’t do that. You work on elements of technique and conditioning and do some sparring. Is that right?

MATT: Yeah. I was at jiu-jitsu last night actually. I was drilling with Matt, one of the instructors.

It’s really interesting to see the difference between what I’m able to take from a drill or specific technique that we’re working on, and what the high level guys are able to take from it. The difference is such a massive chasm. 

When they’re learning a new concept, they’re experimenting with it, playing with it. They’re figuring out… They’re not just doing the technique, they’re working out the other things they can do with it. They’re saying, “Oh, we’re doing this, but from here, you can go to there.” Or, “This position leads into that, which can lead to this or this.” 

Rather than thinking in linear pathways, they’re thinking of branches and options.

ANDREW: I assume that’s something you get from fluency. If you know the basics, then you can know the variations. What works with what and how to transition from one to the other. It’s having the experience to know where all the pathways between one thing and another are.

MATT: So if you were an Average Joe accountant, who’s done his training and goes into a job, would you get fluency with all the techniques just by sheer practice?

ANDREW: To a certain extent, yeah. But—and this is probably just as true for accounting as it is for any other kind of job—you get perfectly capable at doing exactly what it is that you do every day. Then you level off very, very quickly. 

Without consciously making an effort to train other aspects that aren’t as specific to your day job, or thinking of new ways to do what it is that you do, but better, I don’t think you’d get better.

There’s a really good book on this called Talent is Overrated by Geoff Colvin. I think he was one of the first guys to popularise and go in-depth on the idea of deliberate practice. 

He talked about Benjamin Franklin and how he learned to write. Franklin wanted to be a great essayist, but he didn’t have a coach, he didn’t have a mentor or a teacher. So what he did was find a magazine at the time that published really, really good essays. Then, he would take an article, cut it up into sentences, then put them in a draw and forget the original article. Six weeks later, he’d open up that drawer, take out all these sentences, and put the essay back together again.

Then he’d compare it with the original to see how the structures differed. How did this guy structure his sentences compared to how I’ve done them? How has he done it differently? How does his story flow better than mine? 

He just did these weird things over and over again. He’d rewrite prose into verse, leave it for two months, and then try to rewrite it in prose again. Again, he’d compare it to the original and see how it differed. 

He was constantly comparing his own work, challenging himself. Through that deliberate practice, he became this fantastic, incredible writer.

There’s a lot of ways to apply that idea. If you want to be a writer, you could do exactly what Franklin did. I think I wrote about this on Medium. Imagine a footballer. There’s a couple parts of their training that are really important. There’s the basic fitness, making sure they’re in good enough physical shape to play the sport. Then there’s the specifics of their position.

If you’re a defender, you work on your marking, your tackling, your heading, your positioning, and how you play with your teammates. To do all those things, you need to be in good shape, fit, flexible, fast. And then you need to work on the technical skills as well. It’s those two aspects.

If I thought about that in my own professional sphere, my conditioning would be mental maths. Making sure I understand percentages, fractions, basic things like that, and doing tons and tons of basic exercises from simple accounting books.

In accounting, everything runs on the idea of debits and credits. On how things affect the balance sheet. Whenever you debit one thing, you have to credit another and the amounts always have to be the same. That’s why it’s called a balance sheet. It always balances

For example, if you get an invoice in from a supplier because you’ve spent money with them, then you debit your profit and loss account. That’s an expense. Then you credit the bit on your balance sheet called creditors, which is people you owe money too.

I don’t want to go into detail, but you can can do a ton of these exercises over and over and over and over again to get really fluent with the fundamentals of accounting. And maybe do some of the mental maths stuff. That takes care of the conditioning aspect.

And the specifics of your job? Well, it’s thinking about the systems you use every day. How well do I understand all of these? Do I understand what I can and can’t do within that system? Do I know it’s limitations, what it’s good at, and how I can change it to help me do my job better? What do I need to deliver to people on a regular basis and how easy is that to produce? Can I make it easier? What do I understand about how it’s made? What goes into producing that piece of work?

I spend ninety percent of my day with at least one spreadsheet open. So how well do I know Microsoft Excel? Do I know the five percent that everyone knows? Do I know how to use some of the other ninety-five percent of it? Do I know how to write macros and VBA code? Do I know how to link to other databases, or link to Powerpoints and Word documents?

There’s tons of ways I can practice and build those skills. Having that in place, as well as being fluent in the fundamentals, I know I’ll be able to do really, really well in my job.

MATT: I was listening to Cal Newport on the James Altucher podcast. He was talking about the story of his musician friend that he described in Deep Work

This guy was practicing and Newport was watching him. He’d play a song, real slow. Then he’d play it again, faster and faster, building it up to the point where he could barely do it. Newport watched him do this again and again.

The point of the anecdote was to illustrate that deliberate practice is only deliberate practice if there’s two things involved. Strain, from working at the boundaries of your ability, and feedback. Without one of those two things, it’s not deliberate practice. 

That sounds like what you described. Putting a strain on your most basic abilities, the building blocks of your discipline or craft, and constantly comparing yourself to a standard that’s higher than where you currently are.

ANDREW: For the musician, that’s a great example of him testing his technical skill. 

But I would bet dollars to donuts that he knows perfectly well, without looking, how to play a D chord and a C chord. He knows exactly why a C chord is a C chord, why it’s those three notes that go into making a C chord and why that sounds different to a D chord. He knows how to play his scales. That would be the equivalent of conditioning. The equivalent of a football player being able to run 10km. If he can’t do that, it doesn’t matter how good you are at heading or tackling. 

Once you have those things down cold, you can move onto the real stress and strain of genuine, proper, deliberate practice.

MATT: All these ideas about deliberate practice, feedback, perpetual improvement, you picked them up at a young age, right?

ANDREW: I think it’s more to do with how I’m wired mentally. I think that these things are important. But I almost think my problem is the other way. I put so much emphasis on that kind of stuff and forget the fact that once you have a lean, efficient, incredible machine, you need to make it do some work and make it produce things. I think you can spend too long optimising the machine itself, rather than having it turn out work.

MATT: That reminds me of a phrase. I’m pretty sure I’m butchering it, but it was something like, “death is premature optimisation.” 

So you had these mental models and tools from quite a young age. Then, from NFU Mutual, you went into Book in a Box. How did that toolkit impact you in both of those jobs? Was the application of those ideas the same, or did it differ slightly?

ANDREW: I’m not sure. I would say that, for the most part, those mental models and ideas about improving performance, I’ve only learnt over the past two, two and a half years. 

When I started at NFU Mutual, it was my first job out of university. That was over five years ago. When I first started, I was a typical, arrogant young kid who thought the world of work was easy. That I would just come up with fantastic ideas, tell people these fantastic ideas and that they would throw buckets of money at me. 

Turns out that doesn’t happen, which is a shame, but that’s life.

MATT: For me, there was a turning point in my life where I started to notice these things. It started with Nassim Taleb’s Antifragile. That was the book that taught me about education, intelligent trial and error, experimentation and things like that. From there, it just snowballed into where and who I am today. 

Was there a turning point for you? Was there one thing that made you reconsider how you look at your career, how you design your life?

ANDREW: I’d be hard pressed to come up with one specific turning point. I remember very, very clearly deciding wholeheartedly to throw myself back into reading. I think that was in 2007 or 2008.

I was reading Ryan Holiday’s early blog, from when he still worked for Tucker Max. I went onto Amazon and I ordered MeditationsFight Club and The 48 Laws of Power. From then on, I’ve spent, I don’t know, thousands of pounds on books.

MATT: I’m the same. We’ve got a two bedroom place and I’m sat in our second room, which I persuaded Molly to let me have as a study. It’s just filled with books.

ANDREW: One of my favourite things is to go on Reddit and look at room porn. Or library porn. Studies with these oak desks and phenomenal bookcases.

I’m looking at my bookcase now and I’m guessing that, if you were stood in front of it, you would see any number of books that you’ve got on your bookshelves too. What’s there? Antifragile and The Black Swan. A bunch of Malcolm Gladwell. NudgePredictably IrrationalInfluence by Cialdini. The 4-Hour Work WeekThe Godfatherby Mario Puzo. A Confederacy of Dunces. Steven Pressfield.

I think it’s similar to your own library in a lot of ways.

MATT: Yeah, definitely.

ANDREW: There’s Cal Newport. There’s Tim Ferriss. There’s some James Altucher. A ton of Robert Greene. The Power Broker by Robert Caro. I’ve got a couple of Ron Chernow books by my bed too.

That was big turning point for me. It was a conscious mind shift. It was like, “Oh yeah. If I just read books a lot, I’ll get an awful lot smarter.”

It wasn’t long after that I began to see a payoff. I remember very clearly one of the first essays I ever wrote in university. Me and my friend both submitted one. He had worked on his for maybe six or seven weeks. He’d lovingly crafted this thing over Christmas break. I sat down at about 10am the day before it was due, cranked it out in eight or nine hours and submitted it. He got, I don’t know, a mid 2:2 and I got a high first. The look on his face when we got our marks back was just priceless. Then he spent ages saying how, of course, I’m naturally good at writing because I read so much.

I thought to myself, “Well, that probably does have a fair bit to do with it.” From then on, I’ve realised there’s umpteen benefits to it and it still amazes me now. The number of times when it’s useful in conversation.

I’ll be like, “Oh yeah. Obviously, that’s a good representation of the idea of BlackSwans, incredibly rare events.” To guys like me and you—especially when we spend our time talking to other people like me and you—it’s easy to think that everyone has heard of the idea of being antifragile. Or of the ten thousand hour rule and deliberate practice. Or the idea of mastery and the forty-eight laws of power. It’s easy to think that everyone understands these things, but not everyone does. When you take that and go out into the real world, it gives you a hell of an advantage.

MATT: There’s two points I want to make here. The first really puzzles me. In my mind, and probably yours too, the benefits of reading and deliberate practice are, quite obviously, immense.


MATT: They’re so obvious, but I don’t see why people don’t go after them more. I find that really difficult to understand.

ANDREW: You and I do it because we enjoy it and we get something out of it. Other people see it as hard work and don’t want to do it.

MATT: There’s another point as well. You were exactly right. As you were listing off those books, I was looking at my shelves and the windowsill next to me, saying, “yeah, yeah, yeah.”

There’s this homogeneous reading list for creatives and entrepreneurs. These people, they’ve all read the same books and they communicate with the same ideas, which is definitely an advantage. To a point. I mean, there’s a reason people are gravitating towards these different authors and different ideas. But there’s this opposing idea from Antifragile. This passage where Taleb says that’s what necessary for success or competence in a field is usually what’s furthest away from what the average person in that field is reading. 

ANDREW: Yeah, that’s true. The very reason these mental models or ideas are useful is because not everyone has read them, not everyone is familiar with them. If everyone fully understood it and did exactly that, then doing it wouldn’t confer any advantage. It’s the differences that make the difference.

I thought about this from the point of view of poker. Think about a whole career in poker. There’s only so many combinations of two cards you can be dealt. There’s a finite number. Everyone is going to be dealt pocket aces the same amount of times, pocket kings the same amount of times, pocket queens the same amount of times. On average, the whole population of poker players is going to get dealt the same cards, in the same positions, in the same situations. Yet, there are players who have lost thousands and thousands. There are players, a bit like me, who maybe broke even or made a bit of money. Then there are players who have made a lot of money.

Players who have made a lot of money, it’s not because they got dealt different hands. It’s not because they got dealt better cards more often than someone else. It’s because they play them differently. 

If everyone played every hand exactly the same as everyone else, no one would ever make any money. You would basically just pass money around the table over and over again. It’s by doing things differently to others in a situation that you make or lose more money than them. 

There is something to be said for reading a little bit differently and reading a little bit wider. One of the people that does this really, really well is the guy who runs Ribbonfarm and Breaking Smart.

MATT: Venkatesh Rao. He’s increasingly invading my thought at the moment.

ANDREW: I don’t necessarily agree with everything he writes, and I don’t necessarily understand everything he writes. But of the people I’ve read online, he is an entirely unique thinker. He has this incredibly incisive viewpoint. And that’s because he reads a lot wider than everyone else. A lot more history. A lot more tech. It gives him a unique viewpoint.

On the other hand, like you said, there’s a reason why the same sort of books tend to be recommended by the same sort of people. To a certain extent, there’s probably a bit of an echo chamber effect. They’re good books. There’s a reason why you and I have read them and enjoyed them.

MATT: That’s the hard bit, isn’t it. Knowing when to follow good advice and when to do your own thing.

Have you read the Robert Coram biography of John Boyd?

ANDREW: No, but I know the gist of it.

MATT: Coram talks about Boyd’s OODA loop. It’s heavily influenced by Sun Tzu and The Art of War. The two and a half thousand year old book of strategy.

In The Art of War, there’s this idea that most strategies can be broken down into cycles of the ordinary and the extraordinary. If you imagine musical notes—like you said with poker hands—there’s a finite amount, but the combinations are infinite. 

That’s how you create great strategies. You blend the ordinary with the extraordinary. If you’re going into entrepreneurship, it would be using the lean framework—idea validation, soliciting and responding to feedback—and knowing when to push on without validation or certainty.

ANDREW: You’re taking different plays from the same playbook. Or different ingredients from the same kitchen and putting them together in different, unique ways. Some of those ways will be terrible. There’s ways to combine the ingredients in my kitchen to make an incredible meal, or to make something absolutely dreadful that no one would ever want to eat.

It’s up to you to decide what you want to do with it.

But there’s a reason why convention is convention. Being contrary just for the sake of it isn’t a good thing. I still want to drive on the same side of the road as everyone else. I still want to walk away from a burning building rather than into it. 

It’s figuring out which are the rules and standards you should follow, and which are the ones that are worth breaking and are safe to break. 

I think it was Taylor Pearson who said, in his book, that entrepreneurship has big returns because it is still perceived as risky. But actually it isn’t. 

MATT: How did you come across Taylor’s work? How has it influenced you? I’m relatively new to him.

ANDREW: It was a fair while ago. I just stumbled on one of his essays and followed his writing for a bit. Then when I was in Austin, working for Book in a Box, I met him a couple of times. He’s a cool guy. 

He led me into reading about the stepping stones of entrepreneurship. If you want to be an entrepreneur, you don’t have to quit your job, find ten million in venture capital and hire twenty developers. You can start by creating a simple product which gives you a little bit of cash. Then you can turn that into a slightly more complicated or bigger ticket product or service, and then you can turn that into a recurring revenue software business. 

The biggest thing I got from Taylor’s work is that you’re going to have to learn to deal with these things. I’m an accountant now. I probably won’t be in twenty years. It’s up to me to put together a suite of skills, experiences and connections that can help me deal with that change. 

It’s a similar idea to The Startup of You, by Reid Hoffman and Ben Casnocha.

MATT: That sort of thing, entrepreneurship, is something I’m trying to figure out now. I’ve got an idea for a service, and I’m trying to validate it. Walking through these steps and frameworks. It’s completely alien to me.

It’s quite scary. But what I’m finding is, it’s like fighting the Resistance. Your fear, how scared you are of things, completely obscures how risky something is. 

There’s zero risk in me creating a pitch and emailing it to someone. There’s no downside. They say no? So what. As long as I’m not a dick about it, I don’t ruin the chance of any future relationship. It’s just not right for them at the time. 

It’s getting over the hump of seeing something as… It’s like equating how scared you are with how risky something is. They’re not the same thing.

Have you read any of the work of Gerd Gigenrenzer?

ANDREW: No, I don’t think so.

MATT: He works in a similar arena to Daniel Kahnemann and Richard Cassidy. But he takes the opposite approach. He says that rather than nudging people to make less risky choices, we should educate ourselves about risk. I haven’t got my head around the debate.

But in one of his books, he explains the difference between risk and uncertainty. Risks can be measured, uncertainty cannot.

It’s constantly keeping that dichotomy in mind and preparing ourselves, not only for the bad situations that we can imagine, but for the things that we can’t.

ANDREW: I’d say that definition of risk is probably true. But only with downside risk.

If I flip a coin, and if it comes up heads, I win a hundred dollars, and if it comes up tails, I win a hundred and fifty dollars, that’s uncertain. I don’t know whether it’s going to be heads or tails. It’s a fifty-fifty chance, but there’s absolutely no risk.

MATT: It’s something I apply to my career and decisions. You have to make a little bit of mental space for the unforeseen circumstances.

ANDREW: If you want to make more money or be happier or have a different and interesting career, you’re going to have to take a couple of chances. But so be it.

I’m nearly twenty-eight now. I can’t think of anything that I could do professionally that would really matter by the time I’m fifty or sixty. There’s no mistake so bad that, if I made it tomorrow, I would never recover from. 

I think my attitude would be a little bit different to Elon Musk for example. He sells Paypal, makes a billion. Actually, a step back from that. He makes fifteen million and invests it all in Paypal. There’s no fucking way I would ever do that. I’d have five million sat in the safest, government, inflation-protected bonds known to man. That’s my rainy day fund.

The difference between nought and a million is huge. The difference between a million and five million is probably decent. The difference between five and ten million is a lot smaller. 

Again, with Paypal, where Musk sold it and made billions. He then took his billions and invested all of it, and more, in Tesla and SpaceX. That’s why he runs world-changing companies and I’m an accountant.

Someone like Mark Zuckerburg gets offered a billion for Facebook. I would sell, I would be straight out the door. I would have sold out so fast that it’s ridiculous. But he’s like, “No, no. I’ll keep going and I’ll turn it into thirty billion.” 

I think, really? Just take your money, go and have fun. But that’s just me.

MATT: Nassim Taleb talked about it in Antifragile. It’s skin in the game. It’s taking risks for what you believe in. If what you believe in is your ability to build a company like that, then you’ve got to keep going. That’s the ultimate skin in the game. You’re exposing yourself to the benefits, but also to the risks.

ANDREW: I respect it, but I feel like, at that level, it’s not even particularly rational to keep going.

What’s the difference in utility between a billion and twenty-five billion? Well, he’s going to give most of it away anyway, so what does it really matter? For those guys, it’s more about the challenge of building the company.

I don’t know enough about Mark Zuckerburg to know whether or not he’s taken any money off the table and made himself a little nest egg somewhere. I assume he probably has, but I’ve no idea. But if you’re worth twenty-five billion dollars, and a hundred percent of that is in one incredibly risky tech stock, I’d question your asset allocation. 

But there you go, that’s just me.