Hindsight is 20/20 Reflecting on my entrepreneurial mistakes and how I'd fix them

"I was 17-years-old when I started my first business. My friends were all applying to university but, by the time A-levels were over and school was out for summer, I was already making money online.

So, I grew a small company and started undercutting incumbents in the web hosting market. They were grossly overcharging customers for something that should have cost peanuts.

By the time I was 24, I had sold that company, SupaNames, to a UK public limited company (PLC) in a £2.1m exit deal having turned a £150 investment into more than 24,000 customers. I'm afraid to say that I only made one wise investment with the money. I bought a penthouse apartment in Birmingham, I bought a Ferrari, and I invested £275,000 into setting up business number two, which I still run today. The wise investment was the property. The car I was far too scared to drive so I just sort of stared at it on the driveway for a few months before I finally sold it. As for the startup money, that was unwisely frittered away – and here's why.

I'd had the idea for Time Etc when I was working on my first business. I was always overwhelmed by small tasks like paying bills, chasing late payers, expense reports, or sharing paperwork with our accountant. Because I was so busy, I'd ignore these jobs, they'd pile up, and some would turn into problems. Of course, if I had done those tasks myself, my business would have suffered. So, in 2007, I decided to launch a company that would connect time-poor entrepreneurs and busy professionals with experienced personal assistants who could take on these small administrative tasks and help their clients work out what to prioritise.

I hired a grand, fancy office and filled it with brilliant Personal Assistants. There was one major problem: we had no customers yet. The £275,000 cash injection had given me the confidence to go out all guns blazing but, with such huge overheads, we burned through that money in a matter of months. Added to that, our small and initially enthusiastic team didn't have enough to do and, as a result, people lost motivation. After some soul searching I remembered that I was, in fact, a tech person. So why was I trying to launch a people business? I rewound and started again, this time building the technology to support an army of freelance, virtual assistants. The platform would also be client-facing, so people could be matched with VAs and set their tasks through it.

It was a hit. Our virtual assistants liked the flexibility of being able to work from anywhere (this was years before the pandemic) and our customer growth was strong and steady, particularly in the US. We achieved this without any external investment, growing organically, led by feedback from our customers.

Fast forward a few years, and the business was healthy, but I was not. I was clocking up 100 hours per week at the office. I found making decisions hard, even small challenges seemed insurmountable, I was permanently plagued by coughs and colds, and my emotions were all over the place. Back then, 'burnout' wasn't in the lexicon. I just knew that I couldn't go to work anymore, and that my relationships with friends and family were fraught. After trying all sorts of productivity hacks and temporary fixes, I eventually worked out that my entire approach to work and entrepreneurship needed overhauling.

I had thought that 'time in' was directly proportional to 'success out'. This is wrong; it's dangerous information that's hurting people. Working smart is vastly better than working hard. Understanding this has completely changed the way I work. My work week is now just 35 hours, I spend all my spare time with my three children, and the business has never been healthier.

My advice to other entrepreneurs is this:

1. Don't lose sight of what you're good at like I did. Your unique skills are an asset. Beyond that, work on your empathy and leadership skills; there's no avoiding it if you hope to grow a healthy business with motivated people.
2. Get into the habit of delegating low-value but nevertheless important tasks early on. Entrepreneurs work an average 46-hour week and spend, on average, 36% of it doing low-value administrative tasks like invoicing, data entry and ordering office supplies. But it may not be a coincidence that those who self-identify as 'expert delegators' also have healthier revenue growth and profit margins (source).
3. Prioritise your mental and physical health above all else, and make sure your team's health is covered too. Rest and relaxation isn't a reward for hard work, it's a non-negotiable necessity if you want to keep working and enjoy your life. Scheduled breaks should be sacrosanct.
4. Consider what your business would look like if you didn't take external investment. I always knew I didn't want a fast-growth startup and a quick exit, but a strong, stable business that I could grow with for many years, without anyone dictating the terms. I've no regrets that we bootstrapped Time Etc.