What were milestones that you encountered becoming a CEO?

Everyone’s journey is a bit different. Clearly, some folks are skilled enough to start right there, e.g. the Stripe founders, Bill Gates, etc.

For me, it took a while to build up the experiences and confidence to get there:

  1. First, I worked with enough startups and CEOs to “get it”. I had a chance as a startup lawyer working in “Silicon Valley” to work with 20+ startups. Saw a few IPO, a bunch get acquired, a number fail. This also gave me a chance to interact with dozens of CEOs, founders and VCs. This doesn’t teach you how to be a CEO yourself, but it does help you learn what the best ones do. So you can copy them a bit.
  2. Second, I joined the best startup that would have me, as a Director and then Senior Director. We then had our own mini rocketship, hitting challenges and being acquired, and then being part of an IPO. I didn’t build it myself. But I got to part of the management team and make mistakes, and work cross-functionally with the other leaders and managers.
  3. Third, I then managed a small team. This was critical to learning what management really was. The first team I managed I inherited, and I was terrible at it. But I started to learn what it took to recruit, inspire, and yes fail a team.
  4. Fourth, I found a great co-founder. When the time came when I found some white space, an opportunity to start a company, there was no way I could have done it without a co-founder better than me. Luckily, she worked in the same company and had co-invented the technology.
  5. Fifth, I raised the money and built the team and closed the first customers. You don’t always need to raise money to do a start-up. Bootstrapping is far better. But if you do need to raise money, it’s the CEO that has to do it. And I learned to recruit. To hire our CTO, our first VPE, etc. etc. And to close $6m in customer contracts through founder-led sales.

I’m still learning.

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