15 Rules for Cofounders

INTRO

Hey, I’m Tim! ☕

Gagan Biyani is the cofounder of Udemy, Growth Hackers, Sprig, and Maven.

In 20 years of building companies, he’s had 10+ different cofounders.

These are this 15 rules for cofounders — and my take on each one.

I couldn’t resist getting a little meta: I cold DM’ed his current cofounder, Wes Kao, to chat about product strategy and mentorship.

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Gagan’s 15 Rules

I’ll share how much I agree (or don’t) and break down why.

Then, I’ll tally it up at the end.

Let’s get into it.

1. Somewhat disagree. You don’t have to but I strongly recommend you do. Survivorship bias is strong with this one.

   
   There are many more strangers → cofounders that failed.

2. Strongly agree. This reduces confusion, impacts equity, and ensures decisive leadership.
   
   More info from a16z on cofounder prenups here.

3. Strongly agree. Kind of renders Rule 1 redundant, doesn’t it? You get to know each other by having a trial period, no strings attached.

4. Somewhat agree. Yes, you should be willing to have an equal equity split with your cofounder, but that doesn’t mean you should.
   
   A slight imbalance (e.g., 49/51) helps with decision-making.

5. Strongly agree.

6. Strongly disagree. Align first on personality — not passion, not purpose.

   
   Ideas pivot, markets shift, and strategies evolve. Personality is what’s left when everything else is in the air.

7. Somewhat agree. There has to be some sort of gravitational pull that you can’t quite explain.

   
   However, understand the difference between inclination and learned skills.

8. Somewhat agree. I get the sentiment but if it’s impossible to predict, then why try to predict it?

   
   More useful would be to keep a pulse check on it and evaluate as you go.

9. Strongly agree. It’s really important to get to know each other outside the confines of your work. Get into hobbies, family, friends, other interests, etc.

   
   Here’s the guide he linked.

10. Strongly agree. This should be part of Rule 9.

11. Strongly disagree. Using the same fundraising and product examples he did:

    
    The business cofounder could be responsible for all of it. The technical cofounder could stay out of it and focus on engineering.

    
    But that’s not how the best cofounders handle it. They tackle the same challenge from different angles.

    
    The business founder still takes charge of pitching. The technical cofounder prepares the data room, performance metrics, and takes over technical Q&A.

    
    On the other hand, the business cofounder supports product development by talking to users, building non-technical demos, and creating documentation.

12. Strongly agree. It’s tempting to overlook this when they bring flashy credentials or that one expertise you’re chasing.

    
    But don’t let it bite you in the ass.

13. Strongly agree. That’s my entire mission.

    
    If it’s getting ugly, you can book time with me to get it sorted out.

14. Somewhat agree. In theory, this works. In practice, you’re unlikely to learn much, unless it’s really good or really bad.

15. Strongly agree. I chatted with a cofounding team where one had to resign but they took it in stride and he later became an investor in the company.

    
    I’ve also seen cases where cofounders were stubborn about unwanted changes and that led to the cofoundership crumbling.

Survey Says…

Strongly agree: 8

Somewhat agree: 4

Somewhat disagree: 1

Strongly disagree: 2

This goes to show that some things are “best practices” but even a few disagreements show deeper nuances worth unpacking.

More to come.

How I Can Help

ONE MORE THING

Every time you refer someone, you:

1. Look like a genius for finding Cherrytree.

2. Might just rescue a struggling cofoundership.

3. Shine a light on the importance of the cofounderships.

4. Make my day.

Thanks y’all,

— Tim He