Lessons from 20 years as an entrepreneur

In 2006, I was MD of a small creative agency in the UK. It wasn’t your typical route into an MD role.

I’d returned from 2 years overseas, traveling around Latin America, Australia and NZ. Instead of returning to London—where I’d made quite a lot of money in a job I didn’t like—I decided to move to Southwest England. My dream was to buy a second-hand estate car and a windsurfer, rent a small cottage by the sea, and write.

The reason I picked Southwest England was my twin brother. He’d taken a job with a yacht manufacturer a few years earlier, and was constantly telling me how great it was down there.

Luckily for me, that yacht business had a supplier – a small creative agency, called DNA Advertising, which did most of its creative work. Thanks to nepotism, DNA hired me as an account-manager/copywriter/salesman/tea-maker.

I didn’t get to do much writing, truth be told, but what I did get was a fast-track education in business.

Back then I was nothing if not self-assured. After only 3 months in the job, I was precocious enough to tell my new bosses that either I needed to become an owner and director of the agency, or I was leaving.

Somehow, they agreed.

Here’s what happened next:

• I got a 10% stake in the company.
• They appointed a 70-year-old captain-of-industry as my mentor.
• I received an incredibly rapid education in business.
• 5 years later I exited.
• Overnight I learned the value of ownership versus salary.
• So I put some cash to work in my first angel investments.
• Growing in confidence, I started Medra Capital with a friend.
• We invested $1.5m into 13 startups (some great picks/mistakes).
• On a roll, I raised $2m for my own startup.
• 2yrs later, I shut it down (N.B. THIS is what “humbling” means).
• I took a job, having said I’d never again work for someone else.
• I spent at least 18 months trying to regain my mojo.
• Eventually I realised there was value in the bad, as well as good.
• So we launched DQventures to help others avoid such failures.

The surprising thing is, along the way, the dream of writing disappeared. Aside from odd moments thinking about writing a novel, I never gave it much thought. But, as things turned out, more than 50% of the work I do for DQ now involves… writing.

Funny how things turn out.

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What’s the moral of the story?

I guess it’s a combination of:

1. If you don’t ask, you don’t get.
2. The best thing a job can provide isn’t payment…
3. …It’s knowledge and experience.
4. But the most likely route to wealth isn’t a job, it’s ownership.
5. However, no matter how good you are, startups are very hard.
6. …So is early-stage investing.
7. To get ahead, lean into what you love and what you’re best at.
8. And be patient…
9. With luck, maybe your dream will eventually come true.