Thelma & Louise

TL;DR

Hey, I’m Tim! ☕

Last week, I posted on LinkedIn about the importance of cofounderships and one of you instantly reached out for help. My ears perked up.

Normally, people reach out to tell me if something resonated or to give content suggestions. But there was a different sense of urgency in your voice.

If you're reading this, you’ll know who you are because —thank you— you handed me the perfect story to share (using fake names Thelma & Louise).

Here’s the one thing to remember: There’s a million things that could kill your company. But if death must find it, may it find your cofoundership alive.

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Let’s get into it ⤵

DEEP DIVE

As a wise philosophy once said, “real.” Let this be a lesson on keeping things real, especially with your cofounder.

Mutiny Moment

• The CEO, Thelma, suddenly tried to oust the CTO, Louise, by demanding that Louise step down to a 5-hour/week advisory role.

• Louise, refusing to back down, sought legal advice but no one could give a clear answer because of their weird equity and board structure.

• Louise confronted Thelma, who admitted she had issues with Louise’s performance but didn’t bring it up because they’re best friends.

• Months of stalemate led Thelma to confessed she actually wanted the advisory role so Louise took over as CEO and kept the CTO role.

Actionable Advice

• Feedback doesn’t have to be harsh. Sweet words mask the bitterness of reality but sugarcoating the truth only delays the inevitable.

• It’s you and your cofounder against the world. If you have an issue with them, take it up with them first before going to somebody else.

• Evaluate role suitability monthly. Life happens, circumstances change. You should document this over time and plan for contingencies.

• Hopefully it doesn’t come to this, but if it does, make sure you have a confidante (investor, friend, mentor, etc) that you can both trust.

TIM’S TAKE

Candid Comments

• It’s heart breaking that they went from college friends and roommates to cofounders who travelled the world together to strangers again.

• During those months of tension, I doubt any real progress was made for the business. They have VCs and a board to answer to though.

• I’ve cofounded with best friends and it can be tougher because you assume you know their feelings and skip explicit communication.

• I’ve found that shifting from “Why did/didn’t you do this?” to “How come this was/wasn’t done?” opens up more constructive dialogue.

Related Resources

• Use Carta to manage all things equity, including cap tables, valuations, fundraising, issuing shares, and expense accounting.

• Startups Gallery handpicks the most promising, early-stage companies every week. Maybe yours could be featured next.

• Tickets for Shitpitch events are still available but selling fast. Pitch or back a startup. I’ll be at the Dallas event on September 10.

• Check out Thentrepreneur for breakdowns from top startups and find out what’s trending with other founders at Foundcy.

LAST LOOK

Make sure your cofounder sees this — either pass it along or get them to subscribe. A solid relationship takes everyone's effort.

Looking for a cofounder coach? Hit reply.

PS: Wondering why you’re hearing from me on Monday? I’m now releasing new editions twice a week — Mondays and Fridays. I’ll change up the format.

Tim He
Founder & CEO