There’s a pattern I’ve observed in a number of my friends who are SaaS CEOs. Some fear their board and VCs. The VCs say “Jump”, they say “How High?” That’s for a different post. That doesn’t work out well for anyone. {This tends to happen when you have an insecure CEO, and VCs who control the company.}
Actually for every 1 of these types of “How High?” SaaS CEOs, there’s probably 2 of a more surprising type: the ones that see their VCs, at least their first investors, as Friends.
By that, I mean as CEO there really aren’t that many people you can talk to about everything happening in the company. Like sometimes no one. But your Board — you get together every 4-8 weeks, and talk about everything, at least everything operational. Sales. Leads. Product. Successes and shortcomings. Financial issues. Cash flow. People issues. Everything.
And your VCs give you some good advice, especially because really no one else can. Because no one else knows what they know, at least at a strategic level, across your entire company. And at the early stages, your interests often really can be very closely aligned.
But then, something changes. And it seems like your VC “Friend” lets you down — from your perspective at least. They always do, as the company grows and evolves. They don’t like a senior hire you make. They aren’t happy about who you are looking to bring in as a Series B investor. They don’t want you to put your friend on the board as the “outside director”, but instead, their friend on the board as the “outside director.” They challenge your option grants, which they think are too generous (they see them as dilutive, you see them as accretive).
It’s a natural process, once you get some traction, and to them, the pie starts to look at a little more zero sum to them, even though it never does to you.
I’m not in any way trying to be critical here. I am eternally grateful to everyone that ever took a chance in investing in any of my companies. And VC advice, as long as you understand its natural bias, can be incredibly valuable. Its only agenda is making lots of money 
This is very valuable and pure. VCs have no fiefdoms to protect, no skill gaps to disguise.
Just remember, no matter how many quiet moments you share — your VCs are your bosses, and your investors. Not your friends.
Don’t get confused, or you’ll make some mistakes. Or at the very least, be disappointed.
BFF image from here.
