As an angel investor or VC, how do you feel when you know one of your portfolio CEOs is making angel investments while they are also growing their own company?
It’s like a sauce or a spice — a little can be good, a lot creates concerns.
It’s important for CEOs, especially once you are post-traction, to engage with other CEOs. You can’t be too isolated, especially after the early days. One of the best ways to grow as a CEO is to engage with other CEOs that are at similar or later stages.
So I strongly encourage CEO dinners, meet-ups, etc. for everyone.
Then, after that, once you are truly at scale, you can begin to get a bit disconnected. 5 years in, you start to not really understand what the current mindset is for new founders today. You’ve become the establishment!
For CEOs and founders that are post-scale, angel investing is one way to stay current. Especially if you have very strong deal flow.
But I’ve found that most CEOs that angel invest later back away from it. Folks like Aaron Levie and Marc Benioff have some of the best angel portfolios on planet earth. But neither of them seem to be investing as much as they used to.
At first, CEOs post-scale do get information and fresh connections from angel investing that do keep them current.
But ultimately, it becomes too much of a distraction. All those CEOs want to meet, talk, get PR, get partnership help. It’s too much. And the financial returns are immaterial. Aaron Levie’s 6% of Box (at $180,000,000 today) will dwarf any angel investment, outside of an Uber or so 😉