7 Important Lessons From A Late Starter Entrepreneur: Learn Quickly From Your Mistakes (Or Die) and More


Another liberating lesson is that you don’t need to know all the answers when you start. Indeed, the basic methodology of a start-up is to experiment and fail quickly. I still remember Haim Mendelson, a Stanford professor with a handsome white beard and a ruthless forensic eye, tearing up my team’s rickety business plan before concluding, “You only have 70% of the answers. . But that’s probably enough.

If you only have 70% answers when you start a business, you are obviously going to make a lot of mistakes. But that’s part of the process: all startups are a game of trial and error. Failure in many ways is inevitable and, if you’re lucky, not fatal. The most important thing is to try to learn from your mistakes.

While journalism tends to be a sequential business – you have to meet your deadline or you’ll have a very short career – running a startup is all about parallel processing. Before you finish one job, another shouts out for your attention. You’re thrilled to hire a terrific marketing manager, then your lawyers spot a landmine in a term sheet. Your team hosts a spectacular event, then a key technology developer quits. Your life becomes an endless series of mini-crises that are rarely fully resolved.

One of the biggest mistakes we made was hiring the wrong people for particular jobs. It wasn’t so much a reflection on them: they were all smart, decent people doing their best. But they weren’t perfectly suited to a largely unstructured and unpredictable work environment. We had no choice but to lose them, which was a painful process for everyone involved.


Investor Fred Adler wrote a book with this title. The phrase has since appeared on countless investor decks, lapel badges, and even throw pillows. But it’s not until you start a business that you realize the terrifying truth that you really can’t stay financially unhappy for long. No amount of customer love or public acclaim for your product matters more than cash. Unless you can generate enough revenue – or continue fundraising – you’re going to go bankrupt. As they say in retail, turnover is vanity, profit is sane, but money is reality.

This realization gnawed at me for the early hours of many nights in April 2020, during the first upsurge of the COVID-19 pandemic in the UK, when Sifted began operating on financial fumes. Although the FT agreed to support the company, it had always made it clear that it would never stop it no matter what. The COVID-19 crisis has challenged our fundraising plans and forced us to face the unwelcome reality that we may soon have to lay off all 14 employees. Luckily, our original investors, a few enthusiastic new converts and the FT came for us and we raised £1.3m (S$2.3m), giving us a boost.


One of the most fun things about being an entrepreneur, even a nano-entrepreneur like me, is swapping war stories with others who have played the game. gave me Kathryn Parsons, the irrepressible co-founder of Decoded, the digital training company. “I think the one essential thing you need as an entrepreneur is to never give up,” she said.

Compared to almost every other founder I’ve met, I started out with huge advantages: the backing of a media brand as strong as the FT, a large network of contacts and a relatively straightforward business proposition.

Even so, there were many heartbreaking moments where I wondered why I had pursued such a crazy idea. My respect for these founders who did everything to build a meaningful business without any of the benefits I enjoyed grew exponentially.