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Hey, I’m Tim! ☕

I confess: I cheated my way through high school and university.

Wouldn’t have graduated otherwise. But weirdly, I think it made me a better entrepreneur.

As cofounders, you’re always hunting for shortcuts, looking for ways to game the system and get that unfair advantage.

But you and your cofounder(s) need to align on where you draw the line. What are y’all really willing to do to get ahead?

Moral Grey Area

Most startups die because they move too slowly, not because they took one too many risks.

Unless it’s the wrong risk.

I feel an obligation to clarify: this isn’t an endorsement of doing shady stuff. This is simply a recounting of what has been done by other startups.

Uber

Uber operated in multiple cities and countries without the proper licenses and ignored regulations. They were accused of using "greyball" software to evade law enforcement.

Airbnb

Airbnb launched in NY, SF, and Barcelona without regard for local rental laws. In New York, they were accused of enabling illegal hotel operations in residential buildings.

Facebook

Remember the Cambridge Analytica scandal? Although they weren’t a startup, Facebook allowed a third-party app to harvest user data for ads without consent.

Startups often thrive because of their ability to play in these grey areas.

To be frank, I’m not here to police you about that.

I’m here to make sure you and your cofounder(s) are on the same page about what you’re willing to do.

Nonobvious Implications

If one of you is comfortable with pushing the limits, but the other is not, you’re on a path toward conflict.

And when the rules are blurry, that conflict escalates quickly.

Suddenly, you have a mismatch of values that can paralyze decision-making. Or, you have a cofounder who’s silently shaming and feeling second-hand guilt.

You have to understand each other's comfort zones. It’s not just about the illegal or immoral stuff. Know each other’s risk tolerance in general.

3 things to consider:

1. Hidden Cost: Misalignment doesn’t just create tension, it also saps energy. Even small compromises create a lingering feeling of unease.

2. Unexpected Places: You assume that you’ll know when you’re stepping into a grey area. But even the smallest shifts in your moral compass can snowball.

3. Scaling Morals: The bigger you get, the less flexibility you’ll have. Decisions that once felt like necessary risks become harder to defend.

You should understand these things about each other:

• What’s the biggest risk you’re willing to take for this company?

• How do you weigh short-term sacrifices versus long-term gains?

• Where do you draw the line between aggressive growth and unethical behavior?

• How do you handle situations where one of you wants to pursue a risky idea that the other is uncertain about? (most important)

The hardest part isn’t finding the grey area. It’s deciding where you draw your line in it.

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Thanks y’all,

Tim He