Lessons Learned in Five Years as a Venture-Backed CEO
Just over five years ago, we raised our Series A and I became a venture backed CEO.
Five years is a long time in startup land and an eternity in crypto.
As someone who never specifically aspired to run a venture-backed startup, nor knew very much about “The Valley”, how the game is played, or any of the people in it, I knew very early that I’d have a lot to learn.
But there was far more than I could ever have guessed.
Most of these I’m still working to apply to myself — and I have a feeling that there are many more in store for me — but in the meantime, I wanted to share the lessons I’ve learned with peers, aspiring CEOs, and the folks at Blockchain planning to start their own companies.
1. Set Good Habits Early
In the early days, you will constantly tell yourself that everything will stabilize after you reach X.
But the reality is, things may never stabilize and you are not likely to be working there when the company stabilizes in 10 years. You really can’t put off living. So set good habits early — I recommend exercise, spending time apart from your phone, and talking deeply with people that love you. Consider having a hobby.
Take regular time out — this will both allow your brain to reset and drive you to build a more resilient organization. Almost no one does this. Embarrassingly, I didn’t learn to do this until Antony Jenkins, a board member, threatened to make it a board meeting metric.
2. Your phone is a liability
You will develop an addiction to your phone. You will feel like you need it at all times. That you must read every message in every general Slack channel.
After the first thirty people, this is not true and if you are to be successful, you need to create mental space for purposeful interactions with people and thoughtful work.
You cannot be present in solving hard problems, or with people, if you are addicted to your phone. Try leaving it behind.
Rest when you can — it’s never going to get easier. Most importantly, track your activity against your goals. Track it or it won’t happen.
3. What do you have to do to win?
You need to know the answer to that question on two levels. The first, at the company level and the second, specific to you.
You personally can’t do everything really well, nor can your company. Figure out what you have to do. The likely case is that you only have enough time to do that, and often barely so.
If you can figure out what your company has to do to win, you will have solved half of your problems.
4. Don’t just recruit the flashiest race car you can
At some point, the company will be successful and you’ll make some key leadership hires. You will be tempted to go for the fanciest hire — the one they’ll put on the front page of the business section.
While the validation that this ‘real person’ will join your startup briefly feels great, it’s far more important to hire people who believe in the mission. Anyone joining your startup should be ready to buckle in for a long, difficult, and unclear road involving a lot of hands-on work.
Look for true believers — you will need people with belief and conviction you can rely on to lead the team with you when times are hard.
5. Everyone was somewhere else before
No one is going to arrive at your startup a blank slate. They’re going to walk in, sit at their desk, and bring in all sorts of habits and baggage they picked up at their first job, in college, in high school, or from their parents.
Expectations and dreams. Desires and insecurities.
So first of all, try not to take everything so personally. It’s easy to feel as though every creation of drama, failure, or lack of effort is directed at you personally. It isn’t. Second, try to be empathetic, understanding and realize that while it may feel all about you sometimes, it really isn’t.
After all, you walked in with your own issues too.
6. Invest in support functions early
You should build your core engineering team and product first. Once you have that done, and have some traction, make sure to invest in a world-class talent and finance function as fast as possible.
A strong talent function will ensure you can win in the long-term and it gets more difficult to build a great one as time goes on. A great finance function is even more critical — without it, you will lack the insight and analysis you need to build an effective business and make the best strategic decisions.
7. Take all “news” with several hundred grains of salt
In the early years, I was obsessed with reading the news about my own industry and tech generally. The sea of noise around financings, product launches, and hires becomes distracting and nearly impossible to determine what’s actually real.
Most of the tech news you read is spin — not reflective of the truth. Oftentimes the press about a company will be rosy when internally the company is struggling, and negative when the company is doing well.
So stop paying so much attention. Focus on what your mission is, put your head down, and figure out what you need to accomplish in order to get there.
8. Put speed first
As CEO, you’re in charge of the tough decisions department. The ability to fully engage in the discussion and then leave it once the decision is made is a skill I’ve developed from watching Jeremy Liew in board meetings, for whom it is a superpower.
There will never be perfect data to make a decision, and perfection often gets in the way of making a perfectly good decision today. So make it. Have a full, intense discussion, but make a call and then insist everyone is behind it.
You will often be wrong. You will often think you should change your mind. So change it — but even so, make the decision fast.
In startup land, speed is your greatest friend.
N.b. Thank you to the kind reviewers of this post, my team, board, investors, and executive coach
