The Road Ahead: Part 1

INTRO

Hey, I’m Tim! ☕

Cofounding a company has never been simpler — or more complicated.

The stakes are higher, the competition fiercer, and the definition of what makes a "good cofounder" is evolving fast.

We're on the brink of a cofounder renaissance.

And with that, here’s Part 1 of my predictions on what’s next for cofoundership.

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Cofoundership 2.0: What’s Next?

When you see enough of something, you notice trends and make predictions. For me, that something happens to be cofounderships.

Good predictions don’t come from trying to look further out than everyone else. They come from looking at what's happening now but with unusual depth.

1. Cofounder Coaching Becomes Commonplace

The Great Depression destroyed families.

Families that once felt secure found themselves facing unemployment or reduced wages. Breadwinners suddenly couldn’t put food on the table.

They had to make tough choices: ration food, sell possessions, relocate. The American Dream became a nightmare.

Families decided to split up or have fewer children. Others decided not to start families altogether.

The birthrate plummeted. To many eugenicists, these trends underscored the importance of promoting the marital and family stability of the white middle class.

Thus, the birth and growth of marriage counseling.

Over time, the focus has rightfully shifted from racial purity to forming happy and healthy relationships for everyone.

Along the way, there were 2 mental shifts that allowed this to happen:

1. Society went from ignoring the individual in order to see the system (“take one for the team”) to seeing the individual again as existing in a complex system (higher expectations for relationship quality).

2. The normalization of other forms of therapy, broadly.

Similarly, Covid-19 destroyed companies.

It forced cofounders to confront uncomfortable truths about their businesses. Stress levels were high and conflict became inevitable. But there’s a bright side.

More people realized that they can't overlook the human element in their ventures. The destigmatization of mental health awareness extends to cofounders as well.

As this trend continues, we’re likely to see cofounder coaching become commonplace. Not only that, I can see investors start demanding it, which I’ll talk about in Part 2.

Ultimately, this is another tool to help you create a happy, healthy relationship and by extension, a successful company — because it’s your baby.

2. Cofounder Matchmaking Takes Over

The wave of online, app-based, swipe-and-match, and profile discovery mania from the dating world has now swept into cofounder matching.

We’ve all seen what this has done to modern dating — plenty of upsides, but also some real downsides. Yet I can’t deny the value it brings.

Plus, I’m acquainted with Hazim Mohamad, cofounder of Coffeespace, and Catheryn Li, the brains behind YC’s cofounder matching platform.

Selfishly, it’s probably a good thing for Cherrytree. More cofounders = more potential subscribers.

Still, I feel like I have a duty to voice my concerns.

Maybe I’m thinking too far into it. It’s likely not much more than the usual stuff.

Commoditization, reducing people to numbers and metrics, increases superficiality, ghosting, biases, stereotypes, decision fatigue.

For cofounderships, I don’t believe that’s the full picture, though it’s part of it.

Platforms like Tinder have redefined success as quick, casual encounters, where shallow relationships are expected. From there, they can “see where it goes” or decide to end it at that.

And if it’s mutual, it’s a win-win.

Becoming cofounders, however, is like a marriage, in which case the Tinder model would be like randomized forced marriages based on initial attraction.

On the other hand, the efficiency can’t be overlooked though. There have been 250,000+ swipes on Coffeespace and 100,000+ matches through YC.

But the only way this model works long-term is if the definition of success changes like it did changed for dating.

The goal should be quick, casual encounters, where shallow relationships are expected. Maybe a small project together. Or a trial period.

From there, you can “see where it goes” or decide to end it at that.

The danger of labeling it a cofounder matching platform is that when people match, they automatically assume they’re expected to be cofounders.

That’s not the case.

And then there’s the verified, premium, super, gold, whatever crowd. While it may be a cash grab for dating apps, I think there’s a version of it that may actually be beneficial for cofounders.

People will need some sort of vetting system.

I’ll cover that in Part 2.

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