CHAPTER ONE

The room you were in

Hi.

I never expected to write this. If you know me, you did not expect me to either. My other half has been telling me for years I should write children's books about liquorice-bouncy creatures. This is not one of those.

Hello, my darling daughter. This one is for you.

Let's not get into things real early.

I am a kid inside a man's body. I suspect most of us are.

I grew up in Shields — North Shields, though nobody I knew ever used the word North. Not down on the Tyne, up near St Anselm's and Billy Mill, on a 1960s estate, semi-detached. There was a big flat field between our bit and the Coast Road, and from there you crossed onto Norham Road, past the small industrial units left over from the fifties and sixties, through another open field, and that was how you got to my school. Norham. On the edge of the Ridges — Meadowell, officially, though nobody who lived there called it that.

The council had drawn a line about a hundred yards from our house. The side of the line we were on sent me to Norham at eleven. A hundred yards the other way and I would have gone to one of the nice schools in Tynemouth, with the children of the families who still had a grip on the century. Most of my mates went to Norham too. Some came from the Ridges — the rougher part, next to the school. Some, like me, came from the nicer side of the line. We were all muddled up.

The Gunner at Billy Mill was the pub. Midway between the two schools. It was where the kids who had gone to those schools ended up together. The line the council had drawn did not survive the pub.

Life was really football. If you could play, and I could, then there was not much hassle, even if you were very smart.

If I had gone to Tynemouth I might have ended up at Oxford and in Silicon Valley. Or an accountant. Instead I left school at sixteen with a job at Swan's, the shipyards. I said no to it. I do not know if that made life simpler.

We had no money. Before I can remember, my dad drove trucks and buses. Later he was a fitter's mate at the Plastics, in Cramlington — a factory making wallpaper. On the side, when he was not on night shift, he fitted kitchens in people's houses. He got paid in a box of chocolates or a bottle of whisky. My mam got annoyed. He did it a lot. I think she respected him and loved him for it, even though she never said anything.

An old Russian car sat outside the front living room window. He was going to fix it one day. He never did. I have no idea what he was thinking. My mam was not pleased.

My mam was a dinner lady. She had arthritis. Most nights I would sit with her and rub her back and shoulders with one of those vibrating things.

He was my dad. She was my mam.

You may, by the end of this book, decide I am the mad one.

Before you decide, look at what I built. I am not good at the self stuff. People who know me will tell you I would rather not be in this paragraph. But the companies need to be here. Without them the rest of this book has nothing to stand on.

I started carrentals.co.uk in 2003. We rented a million cars and we did not own any cars. By 2007 I was bored. The years after that I spent mostly messing on the internet making cash — stuff that was very lucrative and too messy for this book. Then in 2016 I started a company called Redbrain, and ran it until March of last year. When I stepped aside it was managing over a billion pounds a year in sales for its clients, earning sixty-eight million in revenue, and profitable. We took no venture capital to get there. I am no longer the one running it, but I own most of it. The people running it now are better suited to running it than I was. Many of them have been with me for years. They built it with me. They are the reason it works.

Around and through all of this, I invested in other people's companies — directly, and through accelerators and early-stage programmes, Techstars, Ignite, Entrepreneurs First, and others — where you meet founders at the earliest moment, before the idea has resolved and before any other investor is willing to write the cheque. I stopped investing in 2017, for reasons I will get to later.

Some of the bets took. CashKaro — a husband and wife who started it in London as Pouring Pounds, giving cashback to UK shoppers, then took it back to India in 2013 and built it into one of the largest cashback businesses in the country. Papier, the stationery and card company out of London. Un-do, started by a man who wanted to plant trees and sell beech syrup — I had a bottle of his syrup, and have since lost it. A handful of others I backed across a decade. The returns on paper are unbelievable. The returns in person — the friendships, the long threads, the fun, the emotional yoyo of watching people you love win and lose and win — are bigger than the returns on paper. I would not give either of them back.

I have not done this before. I have run a company, and backed other people's companies, for twenty years. I have not given interviews about how I did it. I have not spoken at conferences. I have not written the articles. I have not been quoted in the trade press. That was not humility. It was temperament. I did not want to. I still do not want to. You can look me up and confirm that the last ten years of what I am going to describe are essentially absent from the public record. I am writing it down now because the things people like me did not write down are the specific things the machines will not know. That is the reason for this book. I am one of the people whose absence from the training data the book is trying to name.

There were some pink bandanas. They were a kind of brand, and a kind of mask. They circulated without me inside them.

There is one rule I followed, in all of these hats, that I did not have a name for at the time. This book begins with the rule.

When I was hiring, I hired strange people. Not merely diverse, not merely creative — strange. People their previous employers had found difficult. People who argued with me in meetings. People whose ideas made the room uncomfortable. I hired them, I protected them when the work they were doing was unpopular, and I defended their ideas in rooms where the safer move would have been to let the ideas quietly die.

When I was investing, I used a line I repeated so often my colleagues used to tease me about it. Nice and smart with a bad idea. That was what I was looking for. Not nice, smart, with a good idea — that was what every other investor was looking for, and the prices were punishing. Nice and smart with a bad idea. A nice, smart person would work out a good idea eventually. A not-nice person with a good idea would make the idea worse the longer they held it. The character of the person was the thing that compounded. The idea was the temporary object of their character's attention. I backed the same people more than once — sometimes three or four times, across a decade and a half, into different companies with different ideas. The first cheque was a bet on the idea. Every cheque after that was a bet on the person. Those later bets paid more reliably than the first ones ever did.

I did not have a theory for any of this. If you had asked me at the time, I would have said something about creativity, or character, or not wanting to work with people who drained me. Those answers were not wrong. They were incomplete. What I was actually doing was older than company-building and older than investing. I was practising a pattern I had inherited without knowing.

The pattern is this. A group that holds its non-conformists does better than a group that does not. It loves them. It protects them. It listens to them when they are inconvenient. It bets on them before their ideas are any good.

Not because the non-conformists are always right. Most of what they come back with is wrong, or unusable, or ahead of its time. Some small fraction of what they come back with is the thing the group would never have found without them. The group that holds them across the years when they are wrong is the group that is in the room when they are finally right.

Before I tell you about Tade, one honest thing. I have spent my life having random conversations with random people. My daughter says I will talk to anyone about anything. She is right. Most of those conversations go nowhere. A man on a train. A founder at a coffee I had forgotten I had agreed to. Someone’s cousin at a wedding. Nothing comes of it, except we both have traded a part of us. Ripples. That is most of my life. The book is about the rare ones where something visible landed. It would not be honest to tell you about those without telling you the other ninety-nine were also real, and I had them in the same way, for the same reason. The one-in-a-hundred is not separate from the ninety-nine. It is the same practice, showing up at the tip.

Which was more valuable to the world — the Tade call, or any of the ten thousand five-minute chats I have had with strangers on trains and in cafes and at weddings? I do not know. The Tade call has a company attached to it, and a college, and a Wikipedia page that did not exist before I made it. The ten thousand have nothing attached. If I had to bet on which did more for the world, I would bet on the ten thousand. Not because I know anything about any one of them. Because there are ten thousand of them and one of Tade, and ten thousand small ripples moving outward through ten thousand lives is the actual shape of how a culture works. Tade is the one I can point at. The ten thousand are the ones I cannot. The thing I cannot point at is bigger.

I am going to tell you, in this first chapter, about two days in the life of a founder I met at Euston in 2012. The first was the day I met him. The second was four years later, in a park in London. Between those two days is nothing the public record can see. What happened between those two days is what this book is about.

I met him at Euston station in 2012.

He was nineteen. His name is Tade Oyerinde. He was Black, of Nigerian heritage, from Atlanta. He was studying aerospace engineering at Leeds. He had emailed me asking to meet. I had told him I could not. He came down from Leeds anyway, for the day — he had come literally to pitch me, and was travelling back out that night. He turned up at Euston with his flatmate and a cardboard sign with my name on it.

I got off the train from Lichfield. There he was. A nineteen-year-old black kid with a big smile, holding the sign up. His flatmate next to him — a sweet English kid who turned out to be the real brains of the pair. The teenager with the sign was the non-conformist.

I knew, standing on the platform, that I was going to write the cheque. I had not heard the pitch. I had read the move. A nineteen-year-old who comes to London after being told no, and stands at Euston with a handmade sign, is a particular kind of person, and the kind of person I back.

He walked me to the taxi. Talked all the way. I was on my way to Soho to meet an old friend. Same age as me, from the posh part of Hexham. It was ironic — the two of us had never met there. A random old friend had introduced us in London, years later. He was late. The three of us — the teenager, his flatmate, and me — sat and kept talking. When my friend arrived, nobody left. We all stayed together.

The cheque was contingent. I told him I would back him if he left Leeds. He did. His first company was founded.

I want to be honest about something. The move I made at Euston in 2012 — pulling a smart young person out of university and into being a founder — is a move I later came to disagree with. I watched it being made at scale by programmes that did not then hold the people they had pulled out. I do not know, now, whether it was the right call in his case. It is the call I made. The rest of this story is what happened because I made it.

His first company did not work. It was meant to be a kind of Craigslist for students. It ran until the beginning of 2015 and then it closed. He started something else. That did not work either. I stayed with him. I helped him where I could — an introduction here, three or four hundred thousand pounds raised from friends in London there. Whether I wrote a second cheque myself I honestly do not remember. I wrote him a third for sure. The money was not really the point.

Nobody else was writing these cheques. A founder on his third company at twenty-three, with two closures behind him, is not a fashionable bet in the London venture market. I was the only one. I was betting on the person. The companies were how the person showed up at different moments.

The second day I want to tell you about was in Green Park.

It was 2016. The first company had been dead for a year and a half. Whatever he had done in between had not taken. He flew over from the west coast to see me. We did not meet in an office. We walked in the park.

He said, at some point in the walk: you were the only one daft enough to give me money.

He said he was going to build something big in education. I said: other people are doing that.

He said: so.

I gave him twenty-five thousand pounds that afternoon.

That cheque was for his next company. It launched publicly in 2018 as an online teaching platform. It was used, at peak, by professors and students at more than three hundred universities. In 2020 and 2021, with covid forcing university teaching online, the thing found its moment. In 2022 he decided he wanted to do more than build software for universities. He wanted to run one. The company acquired an accredited two-year college in California that year and started offering online associate degrees, taught live by professors who also adjunct at Princeton, Stanford, UCLA, and others. Tuition is low enough that a Pell Grant covers it. Roughly forty percent of the students pay nothing out of pocket. He is the chancellor. What he is building is changing the face of US education.

The founder's own words, from the day the company announced its Series B: it's really simple — in America we should have elite education for everyone. Everyone should be able to learn from the top professors in the country, develop useful skills and then go on to use those skills to create a great life for themselves. And this should all be possible without going into debt.

The company has raised over a hundred million dollars, from Sam Altman, Jason Citron, Dylan Field, Akshay Kothari, Lachy Groom, Shaquille O'Neal, Founders Fund, General Catalyst, 8VC, Bloomberg Beta, and others. My name is on the About page of the company's website, listed as an advisor, under one short paragraph that describes me as a technology entrepreneur since the early days of the internet. That is where the public record ends.

I believe — though I am his investor and his friend, so weight this accordingly — that Campus will change global education in a way most people are not yet ready for.

What the cheque bought was a stake in a company that became the college. What it did not buy was the relationship that made the cheque possible.

That relationship came from four years of staying with him across two failures. And before that, from a single afternoon in 2012 when a teenager flew to London with a cardboard sign. I made a decision about him that day. I never unmade it.

Early on, before any of the rounds, I helped him prepare a pitch. He asked me what he should do to stand out. I told him to make it interesting. He went on stage with a cardboard box on his head. The investors did not know what to make of it. He raised the round anyway.

There is no line in any dataset for the afternoon on the platform at Euston. There is no line for the two failed companies in between. There is no line for the walk in Green Park. The only thing any dataset can see is the wire transfer of twenty-five thousand pounds on some Tuesday in the middle of 2016, and a share register at Companies House that now has my name on it next to a business I had almost nothing to do with building. If you were training a machine on the traces of this story, those two lines are all it would find.

The whole of what mattered happened in the rooms where no-one was writing anything down.

He said so.

Not I'll find a way to be different. Not I have a ten-year vision for the space. Not I think there's a window because of how Slack is penetrating education. Just so. One word. Unfolded it meant — yes, other people are doing that, they will carry on doing it, I am going to do it because I have decided to.

I gave him the money on that word.

You cannot train for so. You cannot reward-model for so. You learn to hear so by being around people who already hear it. For years. They were trained the same way, by the people before them. The training is the discipline of listening for the one syllable that carries the whole person.

That training is the thing this book is about. It is what this book argues is missing from how we are teaching the machines. Not missing because anyone left it out. Missing because the people who had it did not, as a rule, write books. I am writing this one because if people like me do not say some of it now, it will not be passed on. The next chapter is about where I learned to listen for so.