I fired myself as CEO of CB Insights earlier this year.

After announcing this, some early-stage B2B startup founders reached out to asking me to advise them or join their board.

I had never done any advisory work of this type but having made every mistake in the book so why not?

I did it for free (no cash, no equity) and didn’t take any board seats.

I just wanted to see if I’d be useful and if I actually liked it. 

Spoiler alert: I hated it.

Why? 

It was surprisingly and maddeningly repetitive. 

Early-stage startups all face the same problems dressed up a bit differently.

And the solutions aren’t as unique as you’d think. 

I felt a bit like a broken record in these meetings with founders.

So I’m no longer doing any startup advisory but figured I’d distill the things I was repeating into five critical lessons. 

The next time anyone pings me to be an advisor, I’m just going to send them this blog post.

These aren’t MBA theories—they’re battle scars from my own failures.

The 5 lessons are:

1. Narrow the focus, increase the quality
2. Optimize for speed 
3. Don’t hire until it hurts
4. Talk to customers. A lot! 
5. If unsure about a teammate, move on

Most of these are probably quite obvious, but I’ll expand quickly on each in case helpful.

Note: I’ve made every single one of these mistakes. Some of them probably tens of times. 

1. Narrow the focus, increase the quality

Founders love shiny objects and grandiose visions (I’m very guilty of this). 

It’s a trap. 

Trying to do everything for everyone leads to mediocrity across the board. 

Cut ruthlessly until you have one thing you can do better than anyone else for a specific customer. 

Then obsess over quality. 

It’s your simplest differentiator, yet few do it well.

2. Optimize for speed

While big companies deliberate, you should be shipping. 

Forget analysis paralysis—embrace Coinbase founder Brian Armstrong’s mantra: “Action creates information.” 

Move fast, learn faster. 

It’s your secret weapon.

The side benefit of speed is it attracts people with a bias to action and repels people who don’t like to work.

3. Don’t Hire Until It Hurts

There’s no messiah hire. 

You can’t outsource your thinking with the hope someone else will swoop in and figure it out.

Get into the weeds and figure that isht out.

The unfortunate reality is that adding people won’t magically solve your problems. In fact, more likely than not, it will actually create new ones.

Wait until the work piles up to the point of pain. 

Then you’ll know exactly who you need.

And then and only then do you hire someone.

4. Talk to customers. A lot!

Get out of your own head. 

Talk to customers constantly. 

They’ll tell you what’s broken, what they love, and how they do their work. 

It’s not just about chasing new business—stay close to existing users for these insights and also watch how it helps your retention. 

5. If unsure about a teammate, move on.

Frank Slootman nailed it: “When there is a doubt, there is no doubt.” 

If you’re unsure about a team member, that feeling rarely improves. Note: in my experience, it never gets better.

Act fast. 

A misaligned hire is cancer to a small team.

Former college football coach Nick Saban’s sentiment s spot on here

“If you want to make everyone happy, don’t be a leader, sell ice cream.”

Remember: Your job as a founder isn’t to be liked. It’s to win. Make the tough calls. 

You need to be effective, not endearing. 

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That’s everything.

For any startup founders who wanted advice from me, it’s all above. No need for a call. No need to pay me in cash or equity.

Now the key is to take action.

So after you’ve read this, go ship some shit, set up some customer meetings and/or have that hard conversation with that teammate that you’ve been avoiding.

Good luck out there.

“It is remarkable how much long-term advantage we have gotten by trying to be consistently not stupid, instead of trying to be very intelligent.” – Charlie Munger