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Welcome to the Cherrytree newsletter, where I share stories and strategies to help you become the cofounder your startup deserves.

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Roots to Shoots

I made little progress my first 7 years in the startup world, stuck in place, watching time slip by. All of a sudden, I made more progress this summer than I ever believed was possible in a year.

Or so I thought.

Bamboo can stay underground for 5 years before shooting up to its full height in a matter of weeks.

I think there’s something powerful there.

The last 7 years, the days where I felt like I was running in place, the endless effort with nothing to show for it…maybe those were the roots. But this email isn’t about that journey. (I’ll share my progress on LinkedIn).

It’s easy to look at other cofounders (like Ben and Madeline) and judge by what’s visible. Traction, views, deals, launches, events. It’s hard to comprehend the years of “being underground” that they had to go through before reaching that growth.

What’s 1000x more dangerous, is being in different growth stages as your cofounder. I’ve been there.

And if you are too, there are signs. Impatience, repeated miscommunications, mismatched risk appetite, or decisions that feel off because one of you is thinking long-term while the other is reacting to immediate pressure. You blame the situation, the market, or even the other person, but usually, the cause is misaligned emotional growth.

When that happens, even a technically successful startup can feel like a battlefield.

The conventional advice is obvious: communicate more, spend time together, “be patient.” That helps a little, but it doesn’t address the root problem.

Misaligned emotional growth is structural. Here are three approaches that’ve worked in the most high-performing cofounderships I’ve seen:

1. Map the Underground

Think of each cofounder as bamboo. Some roots grow faster, some slower, some wider, some deeper. Make it explicit.

Not just “I’m stressed” or “I’m busy,” but concrete markers of growth. What skills, experiences, or lessons are each of you processing now? Visualize it. Track it.

Recognize that what looks like inertia in one cofounder may actually be deep foundation-building. Once you see it, you stop misinterpreting inaction as resistance, impatience as laziness, or caution as weakness.

2. Time-Shift Decisions

When growth stages are misaligned, the problem is often timing, not capability. The solution is deliberate sequencing.

Assign decisions to the cofounder whose emotional growth is aligned with that type of risk. Delay or break up decisions that require both of you to be fully aligned. It sounds minor, but treating timing as a variable, rather than a flaw, prevents repeated conflict.

3. Construct Invisible Contracts

Much of emotional misalignment is unspoken expectation.

Explicitly write invisible contracts: norms, thresholds, and fallback rules for disagreements, risk-taking, and accountability. They’re not legally binding, but they are psychologically binding.

For example: “If I feel pressure to scale faster than my cofounder can handle, we defer the decision for a week.” Or: “We each get one ‘hold a decision’ pass per month when we feel underprepared.”

The point is, you don’t fix misalignment by “trying harder.” You structure the partnership to accommodate uneven emotional growth.

Done right, it’ll lead to explosive shared growth.

That’s all for now,

Tim He

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