As a boy I was an only child, left to my own devices a lot. I filled the time by making things. Spaceships out of matchboxes and other odds and ends, glued together on the kitchen table. And in the garden, a den. Not a sheet over a washing line. A proper wooden build on stilts, three storeys of it, and it kept growing until it was tall enough that the council got involved and told me to take it down. The strange thing was who used it. I had the most diverse mix of friends you could imagine. The squeaky-clean ones, and a much rougher lot from the other end of things. Different worlds, and both of them in that den, sometimes at the same time. Nobody needed an invitation. I'd built it, and it belonged to whoever turned up. And I noticed something even then, though it took me decades to understand it. For me, the joy was in the building. Imagining the scenes, the scenarios, what the thing could be while it was still becoming. Once it was finished, I barely played in it. The spaceships were the same. Built with total absorption, then set aside.

Years ago I became fascinated by failure. Not avoiding it, but what it actually does: how it teaches, redirects, and builds people in ways success never can. I was so convinced this deserved its own philosophy that I coined a word for it, Failosophy. I bought the domains. I trademarked it. I even built out the economic side and called it Failonomics. Then I made it real. I created The Failosophy Show, a podcast about the importance of failure. I recorded ten or twelve episodes with real guests: an Olympic skier, a former ambassador, a drinks industry pioneer, among others. The thinking was strong. The conversations happened. Then I hit the editing. Hours of audio per episode, excruciating to cut, and the part of the work I found no joy in at all. I published a handful of episodes, decided the conversations were going round in circles and that nobody was getting much out of them, and stopped. The trademark, the domains, and the recordings went in the drawer.

In 2010 I built a personal development programme called Wish & Wisdom. I'd spent 25 years frustrated that nothing on the self-help shelf had any lasting effect on me, so I built my own: a structured system for finding what you actually want, and the route to it that fits who you actually are. I was certain it was a breakthrough. I loved every hour of building it. I was so confident that I rang BBC Three Counties Radio and talked my way into twenty minutes of airtime to promote it. I was nervous, but I did it, live, on one of the biggest local stations in the region. On air, I invited people to a Wish & Wisdom workshop. I hired a village hall as the venue. I set it up and waited. Nobody came. Not one person. I packed up, went home, published the programme quietly as a PDF, built a website for it, and never promoted either again. It sat untouched for sixteen years.

This was the mid-to-late 1990s, the run-up to the dot-com bust, and everyone was piling onto the internet. Businesses were throwing up websites, households were getting online, and new dial-up providers were launching every month to serve them. Every provider claimed to be the fastest and the most reliable, all of them charged by the minute, and nobody actually knew which was best. That was the gap. My company was Net Basics. I built the system that measured the actual speed of the UK's dial-up ISPs, ranked them, and sold the rankings to the internet magazines. For the magazines it was perfect: independent numbers nobody else had, current, comparable, provider by provider. The listings spread into every UK internet magazine's ISP guide, and then into cover-mounted books: entire two-hundred-page giveaways with 200+ ISPs on test. If you bought an internet magazine in the late ’90s and checked the listings before choosing your provider, you were reading Net Basics. It was a home run.

When I worked in North Carolina in the late 1980s, one of the health club regulars became a good friend. Nothing romantic, just two people who got on. Truth be told, I'd known her maybe two weeks when she said, ‘I'd like to take you somewhere.’ Where? ‘You'll see.’ The answer was a two-hour drive into the Appalachian Mountains, and the deeper we went, the quieter it got. Towns thinned to houses, houses thinned to nothing, and my spider sense started ringing. I fought it and stayed in the car. We finally stopped in the middle of absolute nowhere, at a clearing walled with trees. ‘Just follow me.’ Every instinct I had said I wouldn't be coming out of those trees again, and by then it was too late anyway. The hills have eyes, as they say. The trees stood tight beyond a joke: not slow-you-down tight, turn-sideways tight, each trunk pressing your back and your chest as you slid between them, and with every one I squeezed past, the feeling grew. Then everything opened up. Forty years on, I have never forgotten the sight. The Chattooga River, exactly where they filmed Deliverance sixteen years earlier. The power of the water, the steep valley sides, that thick green. If you know the film, they get picked off along that river. The shiver went straight down my spine.

I had a thing about large shopping centres taking trade away from communities. A few years earlier, in the US, I had seen what the big malls did to independent stores, and one of my clients was the family behind one of the big new British shopping centres, so I had watched it from both sides. In response I built a product called Shopper's Guide, and it was a clever little machine. Local shops bought a page in the booklet, each page carried a small discount coupon, and every booklet had a unique number printed on it, which entered its holder into a prize draw. Copies were delivered free through every letterbox in the area, and the winning numbers were published only in the participating local stores, so to find out whether you had won, you had to walk back onto the high street and into the shops. We sold it to particular kinds of places: villages rather than cities, market towns rather than big towns, local high streets. It was good, it was successful, and we got quite a few areas going. This was the late ’80s, and I was thinking about opening more, maybe even franchising it. There were three salespeople altogether, including me. Then we started getting pushed back. Areas that had sold no longer sold, and nobody would give us a straight reason. It turned out the large newspaper groups had been suggesting to the local trade that their future was better positioned with the local newspapers than with Shopper's Guide. I was the one leading the company; the others were in it for a bit of a ride, a bit of fun. And I was too young to start fighting the David and Goliath thing, and I just didn't think it was my fight.

I got involved in the internet during its pioneering days, and went through a phase of registering dot-com domain names, picking them up cheap. One I really liked was consumerology, which I’d registered years before and which had sat there doing nothing ever since. Then one summer I took the family on holiday to Cornwall. Normally I’d have done some work in the evenings, but the weather was miserable and the kids needed cheering up, so for once I did none at all, and for a whole week I never even checked my email. When I got home I found a trail of messages waiting, all about consumerology. The first said, in words to this effect, ‘Hey mate, your domain name consumerology, it’s really cool, I’ll give you a few quid for it.’ Because I hadn’t responded, another had arrived, and then another, the urgency, professionalism and seriousness rising with each one, until there were eleven or twelve of them spanning about a week. The last, which had landed the very day I returned, explained that they were an American company interested in acquiring consumerology, and would I please call their solicitor. My immediate thought was: thank god I never answered the earlier ones. So I made the call, found myself speaking with an American lawyer in London, and over the following week or so we negotiated a price in the tens of thousands of dollars. Then I caught the train down, signed the papers in an ballroom-sized office, and came away with the cheque. The buyer, it turned out, was a major American healthcare company creating a public-facing think tank full of Harvard professors, and they wanted consumerology badly, to be the front of it.

People say to build a successful business you need passion. In 2004, while I was working as the senior innovation guy at a global financial services company, I had an idea I couldn’t put down. I called it Gym Permit. Fitness had been my world: I had run club sales and marketing in the UK and USA, so I knew how clubs made and lost money. The idea was simple: instead of being locked into a membership at one health club, you held a single permit that let you use a whole network of participating clubs, and each club was paid for each visit it received. The obvious objection is that clubs would be cannibalising their own memberships, and that is exactly what I got. The answer is that clubs sit half-empty most of the day carrying high fixed costs, so a permit visitor costs them almost nothing to serve and brings in revenue that would otherwise not exist. More importantly, the permit reaches the people clubs can never sign: the commitment-shy, the travellers, the people who want variety. It grows the market instead of carving it up. So I tested it: I found a quiet office and called a health club, and after many objections, I sold the club’s owner the Gym Permit concept. It was one of the hardest calls I have ever made. After that the day job got much harder, my passion for Gym Permit steadily declined, so I considered myself not up to the task, and the idea never progressed. But that one experience taught me a great deal. Here is the kicker: eight years later a company was founded in Brazil doing exactly what Gym Permit was designed to do. It was called Gympass; today it’s Wellhub, operating across the world and worth billions.

I was driving from Goodlettsville, Tennessee, to Fayetteville, North Carolina, the best part of a nine-hour journey. This was the era of paper maps. I was no map reader at the best of times, and this was an American map, full of interstates that meant little to me. Mid-afternoon the sky went dark and heavy snow set in, so I pulled in at a small out-of-the-way store. I got chatting to the old man who ran it and told him where I was heading, and he showed me a much shorter way across. What he couldn’t know was that I had never learned to read contour lines, so I took his shortcut with no idea that it went straight over the Blue Ridge Mountains. I climbed in blizzard conditions, in a car with no heater, wearing two pairs of gloves, two jumpers and a leather jacket, and it took me forty or fifty three-point turns to get up. I was battered. Then, near the top, I broke through the weather into brilliant sunshine, and spread out below me was the most picturesque lake I have ever seen: Lake Lure, where Dirty Dancing had been filmed less than a year before. It was October, and the view was mine alone.

When I moved from Tennessee to North Carolina I stayed in a motel for a week and became very friendly with the owners, their son, and the staff. One day I came in from work and they all rushed towards me, pointing. The motel was basically a courtyard, mostly closed except for one small entrance, with the main building behind reception overlooking it. Across three or four parking bays, not just one, sat what I can only describe as a huge Addams Family vehicle, tower and everything. Long story short: it belonged to a woman in her eighties, and she was convinced she had designed the next great American car. The Addams Family car was the model. She built the body of the car out of papier-mache, with, I expect, the help of friends. The annual event went as follows: she made it, drove it up from Atlanta, Georgia, all the way up the East coast, staying at this motel on the way, and showed it to some significant or senior people at the car maker, most likely Chrysler or AMC. And in fairness to her, if any company was ever going to say yes, it was AMC, legendary for producing some of the most eccentric, unusual and roundly mocked car designs in American history. They said no. Not now, not this, just no. Then she drove it all the way back down, and the weather tore it to bits. The next year she began rebuilding it, and she did the same thing all over again.