Holy sh*t, THIS is the side hustle gospel.

Earlier this week I came across one of the greatest business talks I've ever heard.

PERIOD.

I didn't learn about it from one of my usual business podcasts and I didn't read about it from any number of my go to founders on Twitter.

Instead, I randomly stumbled on it in the Y Combinator Hacker News forum.

It's not even a recent talk.

It's from over 15 years ago!

The production quality isn't even good.

The audio is rough and the video doesn't even capture the slides the presenter is referring to.

But for anyone who's ever started a side hustle project, or even thought about starting one, this might be the most important 30 minute talk you ever listen to.

But first, a quick story of how I ended up here...

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San Francisco Stranger

Exactly two years ago, I attended a 3-day conference in San Francisco.

On the final night I took a few of my clients out to dinner.

One thing *drink* led to another and before long we found ourselves at a dueling piano bar.

It was a blast. But it got LOUD. And in what felt like a split second, it got so crowded you could barely move.

So, without needing to even exchange a word, we all decided to bail.

Outside on the sidewalk we came up with a plan to hit one final bar before we called it a night.

As our Uber arrived we all piled in and we were off.

What we hadn't noticed until we were all settled was that a random lady had gotten into the car with us. 🤣

After a short period of awkwardness she just said confidently - "That bar got too crazy for me too and all my friends went home...so I'm with you guys now".

In the end, what was intended to be a short stint at bar #2, turned into three more hours of incredible conversation.

It's no exaggeration to say that this lady ended up being one of the most interesting people I have ever met.

About 10 minutes before we all went our separate ways, she told us her full name.

We all instantly knew who she was - the co-founder of one of the hottest startups in San Francisco.

*Despite all of its issues, this still remains one of the coolest things about the city…you truly never know who you’ll bump into.*

Her company had just closed a fundraising round in the hundreds of millions and would go on to be one of the best performing IPOs in the country the following year.

That's why I had to ask her what the hell she was talking about when she had just told us a few minutes prior that she was working on a new startup - one that was just a few weeks old.

What she told me next I will remember for the rest of my life.

As a result of screwing up their cap table and taking on so much outside capital so quickly, her and her cofounder now owned barely a fraction of 1% of the business.

In fact, as she was quick to point out, it wasn't even accurate to refer to it as "her company" anymore.

Here was this lady who was the talk of the town. But in reality, even if this business that she started eventually sold for BILLIONS one day, her personal upside was extremely limited.

So she was already starting a new project. Something smaller. Something she'd take her time on. Something she'd own.

DHH & The Side Hustle Gospel

Fast forward to this past week and an old story from 2018 started circulating on Twitter.

It was about how FanDuel was acquired for $465M in cash and the founders walked away with...NOTHING.

You read that right. Nine years of work - zero, zip, zilch, nada.

Without getting into the weeds, due to something known as a "liquidation preference", two key investors were entitled to the first $559M in the event of an acquisition. And because FanDuel sold for less than this amount...you get the idea

The story immediately gave me flashbacks to our anonymous San Francisco founder and ultimately led me down a rabbit hole.

At the bottom of the rabbit hole was the name of two companies.

Two companies that rejected the entire premise that outside capital was necessary to run a successful business. Two companies that believed profitability (not just growth) from day 1 was the most important thing to ensure long-term survival. Two companies that didn't give a sh*t if the rest of Silicon Valley referred to them as a "lifestyle business".

The first company - Mailchimp.

If you're unfamiliar with the Mailchimp story here's the key takeaway - cofounders Ben Chestnut and Dan Kurzius decided to bootstrap the business for 20 years without ever taking a single dollar of outside investment.

When the pair finally sold to Intuit in 2021 for $12 billion, they dished out $300 million in employee bonuses and evenly split the remaining $11.7 billion.

Because remember, after 20 years, they still owned 100% of the business (!!). INSANE.

The second company - 37Signals (Basecamp).

Basecamp was also founded over 20 years ago by 37Singal cofounder Jason Fried and partner David Heinemeier Hansson (DHH).

Except for a minority share by Amazon’s Jeff Bezos, the company has also never taken outside investment.

*I should point out, when the pair took Bezos' investment in 2006, the company didn't need the cash and Bezos didn't assume any control over the business. Both Fried and DHH simply wanted to protect their own personal downside.*

Today, Basecamp is estimated to pull in over $250M in annual recurring revenue.

What really blew me away was when I learned that DHH helped build this company with just 10 free hours a week while working full time as a consultant.

It was his side hustle. Think about that.

I immediately had to know more about this guy. What's his deal? What's he all about?

And that's what led me to DHH's epic 2008 talk to a group of aspiring startup founders - a talk that I plan to listen to a couple times a year...forever.

You can find the talk HERE.

I'll end with this...

As minority owners, Keysearch represents Mike and I's first foray into the "lifestyle business" arena.

And it really couldn't be a better setup. We have incredible partners and 10,000 amazing customers. We're learning a ton and having an absolute blast along the way.

But here's what I've never been more certain of when it comes to the future of Twin Publishing: Keysearch is the first, it won't be the last.

Have a weekend!! ✌️

-Keith

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P.S. - Let me know what you thought of DHH's talk! Am I crazy, or is it even more relevant today than it was 15 years ago?

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