There are no certainties in an entrepreneur's path, apart from one: you are bound to have a roller coaster ride. No matter how successful you end up being. It's never a straight line to success or failure. Along the way, the true test of whether you have what it takes to make it is what you do in your lowest of low moments. When you are most vulnerable. For make no mistake - they will come!
You need to thrive in the gutter
In my experience you can almost separate people into two: those who stay down when they're down or drift sideways, wither and die. And those who jump back up stronger. My biggest successes, leanings and adventures always followed from such low moments.
When I was weakest and most vulnerable. I'm one of those people who performs much better when things aren't going my way. It's like a slap in the face, it wakes me up, makes me more stubborn and determined to hit back even harder. Peacetime CEOs are those who do well when things are doing well. They are typically the people who you hire to take a business from B to C and scale it up. They are smooth, political and great at blowing the trumpet. But the journey from A to B is definitely a wartime situation. You need to thrive in the gutter.
The First Fall
My first moment of vulnerability was when my first business wasn't scaling. I was in my mid-twenties with no experience at all, no co-founder, partner or other senior member of the team, running what's probably the hardest type of business to run - a service business. Exhausted and demoralized, with employees and clients jumping ship at an accelerating pace, I had to figure a way out. Failure was not an option - I had friend's and family money in the business and countless hours of sweat and anxiety.
I felt like a brick had hit me on the head.
Fortunately my cost base was quite low, so going bust would take a while, but that's like dying a slow and painful death. It's almost better if it's a short sharp blow. I decided to go away for a few days to steam off and think it through. It was in that trip that the idea hit me. Why don't I turn the business on its head, circumvent my own self by turning a service provider to a platform business that connects service providers (like myself) with customers and take a cut instead of delivering the service myself? That way it can scale. It was the 'eureka' moment I was waiting for. PeoplePerHour was born.
Blessings In Disguise
My next low moment was almost two years later. After putting in all the hard work of building a working platform we needed capital to grow the business. After a lot of networking and cold outreach we started having some interest from big name VCs. Within a few months we had a few competing offers so we felt we were guaranteed a deal. Then, literally a week away from closure, the financial meltdown happened. We were back to square one. We had no more than three weeks of runway until we went under.
It was one of those moments your parents are waiting for, thinking 'finally! he'll go get a real job now!' Instead I spent a many sleepless nights contacting absolutely everyone I knew, thought I knew, or didn't know but thought I should have known! I persisted like a dog on a bone, unwilling to give up. In the end that was one of the biggest blessings in disguise. To this day I am pretty sure had the original deal gone through the investors would have pulled the plug later on or in the very least fired me as CEO.
Just when things were going so well
Another low moment was almost at the other end of the roller coaster ride. Burning through a heap of cash per month but with the support from our investors who wanted us to shoot for the stars. Until that support dried up. This time round I knew that the likelihood of raising new money before going bankrupt was slim or close to none. I had to do probably the hardest thing a founder CEO (or any leader) is faced to do. Fire half the team. Some of whom left by themselves, but still moments of downsizing are not for the light-hearted. It was painful demoralizing and also humiliating. I felt I let so many people down. Yet once again, out of that moment of weakness we re-emerged so much stronger. The employees who stayed were investors in the business now, and members of the wartime team. They started - and still do - acting like owners. Not just doing what they are told but thinking for themselves and challenging the status quo, challenging everything including the CEO!
A transformation for the best
Lastly, as a lot of the people that left were the more expensive management layer, this created another transformation. It gave a chance to the more junior, newly fired-up team members to step up and fill some deep shoes. They were now the ones at the front, punching above their weight and doing a job that normally someone ten years their senior would do. The best people, the real 'A-players' are the ones who thrive in these very rare opportunities. And the only way to find out is to put them in one.