Why I love “medium stakes”

I’ve spoken to many founders with 8-figure exits.

They all complain about the same thing.

The first 2 years after the exit are the hardest.

Not because they have to stay for the earn-out.

But because they feel rudderless and without purpose – and deeply unsatisfied.

So, they usually do two things: angel investing and venture building.

And guess what? They hate it.

It turns out that the joy that comes with building a company is because of the required stress and sacrifice.

You can’t have one without the other.

It’s a broken duality. Deep in their souls, they know starting another company is not going to bring lasting happiness.

The Post-Achievement Paradox

This feeling isn’t limited to founders.

You see it when people chase marathons and Iron Man competitions.

You see it in the mad scramble to become a partner or managing director.

Accomplishing things that are hard (and thus require struggle and sacrifice) feels deeply satisfying.

Yet at some point, the grind stops being worth it.

How do you break the cycle?

So, what are you supposed to do when the struggle is no longer worth the reward?

(Yet a big part of you still craves the reward.)

I’ve seen my coaching clients take a few paths.

First, let’s talk about philanthropy.

In most cases, these exited founders don’t really have an appetite for philanthropy.

They’ll give to their local communities and their kids’ schools. They’ll support their friends’ charities.

But they’re typically not interested in setting up the next Gates Foundation.

(Asking WHY they don’t care about philanthropy is a whole other topic.)

Enter the “medium stakes” game

Next, they look for problems to solve that are still deeply rewarding.

After all, they want the satisfaction of completing the goal – without the associated grind.

This is what I like to call medium-stakes games.

Enter “angel investing” and “venture building.”

What are other medium-stakes games?

Training for a marathon, writing a book, teaching a university course, starting a YouTube channel.

Now, if you’re really burnt out, a portfolio of medium-stakes games feels awesome.

(Especially if it lets you capture the Magic Window of parenthood.)

The problem with diversification

Personally, I love living in the land of medium-stake games.

I get to the challenge of building things like a newsletter, podcast, and coaching business – but without feeling like I’m being fed to the wolves.

I get to sleep 9 hours a night – like a baby.

And if I’m honest – if all those things were gone tomorrow, it would be a bummer.

But I’d be fine. I’d find something else to do.

That’s what makes my professional activities a bonafide “medium stakes portfolio.”

However, I’d be remiss if we didn’t bring in some portfolio theory here.

When you combine a bunch of different investments into a portfolio, you often sacrifice the absolute return of the portfolio. The benefit is that your portfolio becomes much less volatile.

(Consider the risk and return profile of a portfolio with 100% stocks and one that is 60/40.)

But there’s a “dark side” to diversification. You’ll never get that “big win.”

Because you’ve opted out of the “high stakes.”

And therefore you must be ok with leaving money on the table.


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