By any objective measure, my first company failed. The saddest part? It happened after seven years.

2015 was, at the same time, the best year of my life and the worst. My son was born. My company almost died. I had to move my family back from New York to London to fix the problems that had surfaced. Along with just under half of my brilliant team, I made my wife redundant whilst she was on maternity leave. I had to part ways with my cofounder. The series of events left me with crushingly low self-esteem and high anxiety. And I carried this trauma around for years after. Looking back now, I’m surprised I got through it. 

I started Glow as an ambitious and naive 30-year-old. When we moved into our first office and I was joined by intrepid co-founding team members, it felt pretty good. When our customer numbers started to grow and we became one of Facebook’s top-tier strategic partners, it felt great. When some of Europe’s greatest venture investors backed us, it felt amazing. When we grew the team to close to 100 people and launched in new countries, I swelled with pride. We won a few awards, I appeared as an ‘expert’ on Sky News, twice, and we were flattered by positive feedback from industry peers.

And then after seven great years, things fell apart pretty quickly. 

We hit a series of issues: we faced rapid and huge changing market dynamics, our technical product couldn’t keep up, causing us to churn customers; we had hired amazing (and amazingly expensive) people in too many places at the same time and burned through our recently raised cash too quickly. As all this was happening, my wife gave birth to our son, Noah. 

What followed was the most intense twelve months of my life. 

I had to battle the board over several very long weeks to justify my rescue plan. I had to make great people redundant. And I had to stand in front of my team and investors in a humiliatingly public mea culpa. 

I had to leave my wife and baby son in NYC every Sunday night to fly back to London, returning to them late on Friday night. I did this for seven weeks before we relocated back for good.

Making people redundant is one of the hardest things I’ve had to do as a leader. The first time I did it, I made sure I had a face-to-face conversation with each person affected, so I could apologise and explain the process 1-1. I barely slept the night before, and a dark cloud hung heavily over me as I walked to the office. The quote “if you’re going through hell, keep going” was a constant mantra in my head during this time. I often would find myself hiding in the toilet so I could cry in private. 

The emergency funding round came at a heavy cost. Not only did it wipe out the value for early shareholders, including those brilliant angels, friends and family, whose belief in me had now been broken. But it came with conditions: we had to draw down the funding in 1-month tranches with approval needed each time. Slowing us down when we needed to speed up. I should have pushed back at this, stressing the need for quick decision making and voicing caution at onerous approval cycles, but sadly this was my inexperience shining through (not helped by the shame of allowing it to happen on my watch).  

Once we’d stabilised the business on to a solid footing, we decided to work towards a sale. In February 2016, 11 months after my son was born, we were acquired and, over the 2 years that followed, would grow the newly combined business 3x, having great fun with my new colleagues as we launched in new markets and strengthened our position, until I left in January 2018. 

The impact this period had on my self-confidence, health and relationship was traumatic and could still be felt for many years after. I ghosted friends for no reason and when I was with them I found it hard to engage, papering over the trauma I was experiencing with platitudes and brush offs. I found solace in escapism, turning to substances and frequent late nights. At work, I experienced crippling anxiety and crushingly low self-esteem. When I was at home I couldn’t sleep at night, couldn’t be present with my wife, was not able to be the husband and father my family deserved. To top it all off, I was pretty miserable company. It took deliberate, and sustained effort over many years, to heal. Looking back now the memories are still raw, I oscillate between embarrassment and sorrow. And at the same time, I’m proud I didn’t give up when it got difficult. If you’re going through hell. Keep going.

I have learned so much from my experience building and selling Glow. I wish I’d known I had these blindspots and worked harder to mitigate them:

1. I didn’t sweat the small stuff enough - putting in place a management framework, like OKRs, to give accountability to the right people, nor did I put in the controls to see problems coming before it was too late.

2. I tried to run after all commercial opportunities - as I wanted to win the race we were in - without addressing the operational stress that I saw around me. 

3. I avoided conflict and didn’t make difficult people decisions quickly enough. 

I have a huge sense of personal responsibility for the failings of Glow. It ate me up for a long time afterward until I learned to refocus that emotion to something productive: helping others avoid making similar mistakes. As the door to Glow closed, two new doors opened: working with early-stage CEOs at Founders Factory as they launch and scale their businesses, and launching a CBD brand, Good Remedy to help people manage stress and improve focus. 

What I double down on now when coaching CEOs and their teams, are reflections of my failures. They’re in the hope that when I have my time as CEO again, I will have learned to mitigate my blindspots. 

Remember when you start a company, you should be prepared to be in it for a long time. Plan for a decade of your life. Whilst there will always be a never-ending list of things that you need to do, running a business is all-consuming after all, it’s essential to give yourself time to recover, get perspective and recharge. Here are some resources and frameworks that worked - and continue to work - well for me:

• Find a peer group of founders where you can discuss the scary real things that are going on. At Founders Factory, we host regular ‘Founder Circles’ - an opportunity for small groups of founders to get together and share learnings or seek advice.

• Know yourself - the greatest gift you can give your team is the work you do to improve yourself. The best leaders are those who understand what they’re running toward, what they’re running away from, and why. Read this from the brilliant NFX which has everything you need to know. And then listen to this podcast series, from Adam Grant + TED.   

• Implement a comms architecture + KPIs and tie them to your vision + strategy. More on this topic in a future post, but this is the best piece I’ve read on it. 

• Find a coach / mentor / psychotherapist. Go check out: Ben McKie at Psyched Global, Nova Cobban, Rebecca Morley, PUSH, Inside Out, George Warren.

  
  
  
  

• Hold on closely to the real relationships that exist outside of your professional life. Everything else can and will bounce back.

As an entrepreneur, you will have to navigate through some of the hardest periods imaginable, and that can leave you feeling hopelessly overwhelmed and out of your depth... and that is OK. It may feel lonely, but remember it's not - every other entrepreneur is going, or has gone, through the same tough times. It's in this crucible of leadership, that great leaders are formed. Keep going.