Dog Catches Car

Hey y’all — do you remember that scene in The Dark Knight where the Joker says…

Turns out that’s not too far off from a founder who eventually exits their company.

We chase successful, in some cases life-changing, exits with a singular focus for years only to… suddenly not have that sense of purpose anymore…

I was struck this week by a blog post called “I am rich and have no idea what to do with my life” where Loom’s co-founder Vinay Hiremath describes how he’s felt lost for over a year since selling it to Atlassian for $975 million.

I’d recommend reading his post in full (it’s relatively short), but here’s why what he’s feeling is something many founders feel, even if their own exit isn’t nearly a billion:

Dog Catches Car

The $60M Hangover

Put yourself in Vinay’s shoes.

After 10 years of grinding you’re excited for a big cashout and maybe either a breather while you rest and vest your full earn-out at the acquirer or just getting onto the next big idea, whatever it may be.

But then you get it and you realize your internal north star is just… gone. The thing you’ve been driving towards for years no longer is at the center of your life.

You’re rudderless and adrift.

What… should you… do…?

In Vinay’s case, he couldn’t take it — he decided to give up a $60M package he had at Atlassian after 5 minutes walking in the woods. One encounter with nature was enough to knock down the value of spending his time in a place he wasn’t energized by.

But the other extreme (diving into a new singular-focus with a new startup) doesn’t work either. Here it is in Vinay’s words:

Over the next few months, Vinay:

• Broke up with his girlfriend of 2 years

• Climbed a 6,800m peak in the Himalayas with no experience

• Joined DOGE for 4 weeks

• Quit and went to Hawaii to learn physics

• Continued to work through existential questions

If that sounds maximally chaotic and all over the place it’s because it is.

But, honestly, if you sold your company for $975M after ten singularly-focused years and suddenly had infinite freedom would you really know how to handle it any better?

The First Rule of Exited Founders Club Is…

Look… committing to building a company, whether you’re raising venture and going for a unicorn exit or not, is not something to take lightly.

It can consume you.

So it’s probably somewhat natural that people avoid mentioning that ultimately succeeding and achieving full liquidity for yourself leaves you with, in some cases, a feeling of loss after the initial celebration wears off.

That’s not really an enticing sales pitch for more people to go become founders, right?

Combine that with how there number of founders who achieve those life-changing outcomes are so low, and it just isn’t something that gets talked about much.

But that’s exactly why we should be talking about it.

When Elon talked about how running a startup is like eating glass, it wasn’t meant to encourage people to become founders — it was to prepare them for the reality.

And, if they back out of starting a company because they hear it might be tough to figure out what to do afterwards, well… I hate to break it to you but they likely weren’t going to get to that point anyway.

The Unavoidable Identity Trap

The premise of Vinay’s post may have surprised some people who smugly say “if I had $975M I’d have nothing to complain about” (which he acknowledges in the post, too) but, to be honest, most of you reading this can probably relate to why he’s feeling that way.

When you’re building a startup, let alone getting it to a $975M exit, you allow it to become part of your identity — in some cases, a big part.

Vinay’s story shows how a decade in founder mode can leave you feeling defined by your startup, instead of the other way around.

It’s a trap, yes, and a therapist’s advice would probably be to find at least one thing outside your company that you can put some focus towards or get excited about… but for the people actually building it can be easier to say than actually prioritize and do.

Personally, the two companies I’ve built to millions in revenue that have given me freedoms in life have required my absolute dedication and focus so I can’t in good conscience say go follow the therapist’s advice.

Maybe the time you spend as an aimless wanderer where “everything feels like a side quest” after a big exit is the price you pay for getting there in the first place. Maybe that’s ok as long as it’s worth it to you.

PS — I’d really recommend reading his piece in full. It’s easily my favorite founder essay of the year so far.

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