10 Things I Wish My Board and VCs Had Told Me

They say CEO is a lonely job, and I guess in some ways true, but in many ways it’s quite the opposite. If you do it right as a founder, there’s nothing more rewarding than getting to work on Monday. Checking in with the team. Being on a journey together.

But what is hard is getting help seeing the forest through the trees. Here are the Top 10 things I wish I’d been told.

So I’m telling you:

1. Power laws are real. $1m MRR is when it gets great. No, it doesn’t get any easier then, per se. It never gets truly easier. But you won’t fail after $10m ARR or so if your customers love you. It is different. And you can build something that will trust last once you get there.

2. Just go find the VP you need. You can miss a quarter if need be. No, you can’t miss every quarter. But you aren’t public. You can miss a quarter intentionally once every 6-8 quarters or so if need be to get something bigger done. Focus as CEO on what will move the needle. Go find the VP you really need. I got the VPs of Sales, Product and Marketing I needed. But I should have taken a pause and just found our true VP of Engineering.

3. Truly beloved products win. Invest more there. 60+ NPS, 130%+ net revenue retention, however you measure it is special. Double down there. You can screw up a lot of other things. Most products are not beloved. If yours is, invest more there and worry a little less about pressure to do new things, new market segments, etc.

4/ If you need a little more $$$, and you are doing well — we will help. I needed just a little more money, but not a ton. Now, I just tell the founders I invested in they can have what I have reserved for later whenever they want (if they’ve earned it). No need to wait. This isn’t bridge financing. It’s throwing in a few nickels from the next round now if it will help the CEO scale faster with less stress.

5/ It’s OK to talk honestly about exit goals. It is OK to sell anytime everyone makes money. I wasn’t comfortable having this discussion. Now I tell founders it is cool to talk about it anytime.

6/ Do not be scared we will block a sale. We fear this as founders. I wasted a lot of energy here where I shouldn’t have, and paradoxically, it can drive a sale earlier than need be. I tell founders now anything is OK if we make money, and if it’s fair, even if we don’t. Just remember, it will take you 5–7 years just to get back to where you were if you sell.

7/ If you need a salary raise, just tell us. Stressing about salary after a few million in ARR is dumb. I asked for a $10k bonus after closing a $500k+ deal in the middle of the worst recession of our lifetimes, and felt uncomfortable about it. Now I just tell founders whatever is fair is fine by me.

8/ Play to your strengths. If you aren’t great at something, do more of what you are great at.

9/ It’s OK to sell some shares later. At $10m ARR or so, you’ll get to sell some. That will help you push on for the next 5–50 years.

10/ You are either a very good or a great CEO. We don’t know which yet. But. We believe in you. Hearing this would have helped a lot. Now I know to tell the founders I work with this exactly. That I am extremely proud to work with them. And that in almost every case, they are better founders than I ever was.

note: original post updated with full video on topic above

Published on July 6, 2020