- Cherrytree
- Posts
- Matching Hoodies and Mismatched Expectations
Matching Hoodies and Mismatched Expectations
We’re crushing KPI's and each other's spirits
Forwarded this email? Subscribe for more.
Hey, I’m Tim! ☕
Every Monday, I help you become a top 1% cofounder.
Actionable advice: Practical tips you can start applying today.
Relatable stories: Real-life experiences from people just like you.
If you really want to answer the unGoogleable questions ↓
Ignoring Ignorance
Many cofounders disagree on if they’re ignoring an issue or if they’re ignorant of it. Let that sink in.
Ignoring = lack of acknowledgement; ignorance = lack of awareness. At any given point, you’re only one conversation away from reaching a clearer source of truth.
The peaks of stock market bubbles, obvious in hindsight, are deceptively difficult to time. There’s no single metric that signals when the clock is about to strike 12:00.
→ Cofounderships on similar trajectories are plagued by the same uncertainty.
As a cofounder, it’s your job to address your blindspots before the bubble bursts.
Three common issues that mask deeper problems when things are “going well.”
Success masks cracks.
When the business is doing good, you assume your cofoundership is solid. In the same week as Twitter’s IPO, the book Hatching Twitter was published and exposed the juvenile backstabbing between the 4 cofounders.
Despite the financial success, their friendships dissolved in a pool of jealousy, passive-aggressiveness, cursing matches, and secret coups to oust one another.Little things add up.
Small annoyances accumulate tension. In the moment, you have more urgent and important matters to handle, but over time, this makes you avoidant and defensive.
Garry Tan talked about his experience starting Posterous in detail in this YouTube video. At first, he didn’t admit it to “keep up the fiction that they were good cofounders for one another.”Never had a fight.
Cofounders who begin with somewhat equal decision-making power are at risk of a major conflict because you’re used to consensus. It’s a red flag when you claim to be equal but own different areas like business and tech.
Overlaps between the areas is what leads to disputes. While Airbnb and Google cofounders had similar equity, they used a weighted voting structure.
When companies become overhyped, you ignore certain truths that contradict the hype. The more you do that, the more you neglect research, and the more ignorant you become.
A booming business doesn’t guarantee a solid cofoundership. But a booming cofoundership leads to a solid business.
That’s all for now,
Tim He
BTW — The Cherrytree cofounder community is now open. Join here →
Work With Me
Coaching — Can be individual or as a cofounding team. Starts at 15-minute quick calls and can be ongoing multi-month engagements.
Workshops — Designed for accelerators, incubators, and venture studios. Learn the fundamentals of building a solid cofoundership from Day 1.
Speaking — Now booking engagements for 2025. Perfect for VCs, unis, and podcasts. Webinars and in-person available.
Our Sponsors
Cherrytree is free. Always has been, always will be. That’s all thanks to our amazing sponsors. Show them some love ↓
Inventory Software Made Easy—Now $499 Off
Looking for inventory software that’s actually easy to use?
inFlow helps you manage inventory, orders, and shipping—without the hassle.
It includes built-in barcode scanning and connects with Shopify, Amazon, QuickBooks, and more.
Try it free and save $499 with code EASY499—for a limited time.
🚀 Compare plans on our pricing page
Quick, hard-hitting business news.
Morning Brew was built on a simple idea: business news doesn’t have to be boring.
Today, it’s the fastest-growing newsletter in the country with over 4.2 million readers—thanks to a format that makes staying informed both easy and enjoyable.
Each morning, Morning Brew delivers the day’s biggest stories—from Wall Street to Silicon Valley and beyond—in bite-sized reads packed with facts, not fluff, and just enough wit to keep things interesting.
Try the newsletter for free and see why busy professionals are ditching jargon-heavy, traditional business media for a smarter, faster way to stay in the loop.