A year ago, I made an outrageous proposal to the CEO at the company I’d only been working at for three months: let me quit, start my own company, and be my first customer. Maybe that doesn’t sound that outrageous. People do things like that every day, right? But for me, at that time, it was the biggest, riskiest move of my life.
By most measures, I’d enjoyed a successful career as a technology leader. I’d run development groups, technology teams, and did a tour as a CTO. I had a great track record for crafting good software, building awesome teams, and holding my own in executive circles. I’d worked for a lot of startups, some that had done well, and if you looked at my resume, you’d think I was successful. And I suppose I was, but I wasn’t happy.
Since I was a kid, I wanted to be an entrepreneur. My father embodies the very definition of an entrepreneur. He grew up poor, couldn’t afford to go to college, and began his career as an electrician. He went on to start several companies, reinventing himself countless times, until he had provided the life for his family that he’d always dreamed of. My brother is a successful entrepreneur in his own right, having started a company right out of college and building his own little empire.
When i was in my early 20s, I was a finalist in a worldwide entrepreneurial contest sponsored by IBM. Ultimately, I didn’t pursue that company because I was in a great situation professionally. I’d always assumed I’d start my own company someday, but as the years went on, life got more complicated. I got married, bought a house, and had kids. Suddenly there were mortgage payments, life insurance, healthcare costs, retirement savings, college savings, etc. We’ve all heard that story before. It seems cliche at this point, but damn is it true.
Even though I’d spent my entire career taking risks by predominantly working at startups, starting my own company had become an unacceptable risk. I began telling myself that being a good dad was more important than being an entrepreneur. When I’d talk about my career with my wife, she’d ask if I still wanted to start a company someday. I’d tell her that my priorities had changed. She’d press harder, and I’d get defensive. She’d eventually drop it, but we both knew that I was hiding from the truth.
In 2012, after a few years of less-than-ideal work situations, I found myself working for a new company. I was happy. I was spending my days doing things I loved, building a great team, improving the culture of the company, and working on some interesting software. And then three months in, the CEO pulled me aside and told me he was selling the company. I went home that night with a very heavy heart. I wasn’t worried about my job security, or the change in leadership — I was jealous. I’d become fast friends with the CEO, and looked up to him as an entrepreneur. He had taken nothing but an idea, and through blood, sweat, and tears, built a successful company. He put in the hard work, made the right decisions, and now he was being rewarded. He deserved it, and I wanted the same.
I didn’t sleep that night. Partly because we had a two month old baby, but mostly because my gears were cranking. The notion of starting my own company, which I’d shoved so far down, had come bursting out. I thought about the financial risk. I was making good money at the time, but hadn’t achieved the level of financial security for my family that I longed for. We had some savings, but our expenses were high. I thought about the logistics. How would I get customers? Where would I work? How would I handle health insurance? Most importantly, I thought about the notion of controlling my own destiny. No matter how well I’d performed in my career, or how much influence I had, I was always just a cog in the machine. On one hand, that was comforting; if things went wrong, I could blame someone else, right? I could hide behind the failures of others. It couldn’t have been my fault — I’m the smart technology leader who does no wrong. On the other hand, I was leaving my fate to chance. I was trusting others to make me their number one priority, and to make decisions with the best interest of my family in mind; and that just wasn’t realistic. I’ve worked with some amazing people who have gone out of their way to do right by me, but ultimately their responsibility was to themselves and their families.
By the morning, I told my wife that I was thinking about starting my own company. She heard me out, and expressed some concern, but told me that she trusted me, and knew how important it was that I take a crack at entrepreneurship at least once in my life. Yes, I married up.
I spent a couple of weeks thinking everything through. I really didn’t want to start a business without any revenue, so I decided that I’d at least try asking my current company if they’d like to be my first customer. Giving notice and asking the same company to be a customer is slightly ludicrous. Some companies would be so mad, or hurt, that you were leaving, the last thing they’d want to do was help you. I had two things working in my favor though: first, I had a feeling that my CEO would understand my desire to start my own company; second, one of my favorite pieces of advice I’ve ever received was “always give someone the opportunity to say no.”
I made the pitch and they accepted. Three weeks later, on September 1st, 2012, Barbershop Labs was born. My entrepreneurial journey had begun!
In part two of this series, I’ll share what I’ve learned in the first year.