Life After a Startup Exit Ain't All Rosy

We all dream about it. Cashing out, getting The Big Check™ and going on a shopping spree with “Bentleys and Benjamins”. But, once the fanfare wears off — What actually happens to all of us?

Do we walk away with a perma-smile until the day we die? Or do we just trade one set of problems for another?  Are we actually happier?

As a Founder with a few exits of my own, I’ve had this conversation with dozens of Founders post-exit who have had anything from a $1 million exit to a multi billion dollar exit.  What’s fascinating is that all of our outcomes tend to tell roughly the same story — and it’s rarely what anyone thinks it is.

Everyone has their own version of their outcome, but if I were to generalize my observations after some very deep and honest conversations over the past couple decades, it looks something like this:

We Lose our Identity

A startup company is very much an extension of its Founder.  The product, the culture, the ambition — is all an extension of us, and it’s something that eventually reflects in our own identity.  For years when we talked about our lives, the startup we built was part and parcel with our identity. It was a part of us.

And then we sold it.

We may have done well with the sale, but one thing is for sure — it’s not ours anymore.  We may still have our title, we may still commute to the same office, but it’s not ours. This loss of identity is brutal.  We can try to snuggle up with our mounds of newfound wealth but it doesn’t replace what’s really lost – a critical piece of who we are that no longer belongs to us.

In some cases we’re not there at all.  Yesterday, the lives and futures of huge swaths of our friends were in our hands.  Now we’re no longer even shared on those silly memes in email or Slack. We’re like the discarded spouse in a relationship of our own invention.  We can’t quite put our fingers on it at first, but we can tell some major part of our life is no longer there.

We miss it — even when we don’t want to admit it.

We Stop being Important

Our calendars used to be filled to the brim with people who needed us. Vendors who were trying to sell us something, employees who were pining for a promotion — even investors who wanted in on our deal.

Now, our inbox has digital tumbleweeds in it.  We keep reaching for that message notification that isn’t there.  No one “needs” us in that same way anymore. We long for one of those vendor pitches because we miss the days when our input mattered.  We’re no longer the gateway to someone else’s pleasure and it feels empty.

We don’t want to admit we loved it, but we can’t ignore that it’s gone.

We Buy all the Things we (think) we Wanted

We run out and buy expensive stuff.  We buy that car, that house, that over-priced piece of jewelry.  We feel we need to see a tangible reward to repay ourselves for the hours and years we lost — the sacrifice we endured and the time we can’t reclaim.  

We buy these things in triumph, only to learn later that the value of anything is the fact that we don’t have it.  Once we have it, we’re wondering why we sacrificed so much to get it. The payoff is never commensurate with the sacrifice.

We start second guessing ourselves.  “Was it worth it? Did we sell to soon? Is selling what we really wanted?” Those questions start amplifying over time, no matter how many times we head to the cash register.

We Feel the Need to “One-up” Ourselves

Anyone who is ambitious enough to build something worth selling tends to be so ambitious that they always want to beat themselves at anything.

“If I sold this for $1 million, then I need to start something that sells for $10 million!”

We build a whole new set of goals not based on what we want or need, but based on what has transpired in the past.  We don’t even need $10 million, but we get fixated on that number because it’s bigger than $1 million. We invent reasons that $10 million is the “right goal”.  We justify it with logic that no one understands but us.

We don’t need $10 million – we need a reason to do something at all.

We get Really, Really, Really Bored

After so many years of grinding and sacrificing the idea of being able to kick back and just breathe for once feels like the last leg of the world’s longest race.  We finally take some time off and do all of the things that we always wanted to do.

We read some books.  We go on some vacations. We take up some hobbies.

Then something really weird happens — we get super frigging bored. What scares us is how quickly it happens. We thought we’d take off an entire year and just work on our tans while doing some deep reading.  Instead, we’re sitting in bed in the middle of the day binge-watching Netflix in a bathrobe that reeks of Cheetos, wine, and body odor. (Note: your odors may vary).

We realize that our startups weren’t just a job — they were how we found the best and most creative use of our energy.  They were our hobby, we just hated what it costs sometimes to maintain them. We yearn to get back to that hobby.

We Run to the next Shiny Thing

At that point we’re so frigging bored we start to think of anything we can to become our “next great startup idea”.

Have you ever noticed that after a band comes out with a hit album that they almost never have another album that’s as good?  That’s because they had their whole lives to think about the first album and were essentially rushed into the next one. That’s what happens with Founders.

We immediately try to fill the void that was our last great startup idea.  We jump onto any new idea that seems to fit the bill of “new”, “noteworthy”, and immediately available.  Incidentally this tends to be a really horrible idea.

But, we have to do something.  We can’t sit around and talk about that house we just bought forever.  We need something new to fuel us. We need the next shiny thing or we’re going to go mad inside this giant new house with our odorous bathrobe!  (Man, we should really wash this thing.)

We Start Getting Depressed

We can’t figure out what’s happening to us.  We can’t quite process the fact that so much of our identity, our relationships and our creative output was so intently focused on our startup – we thought it was just a job!  We thought selling it was the big payoff!

WTF?

We find ourselves getting lonely and depressed.  We have all day to sit around and think about it while our friends  — those suckers who still have jobs (!!!) — are too busy to spend time with us.

We have a Hard Time Talking About it

When we’re sitting across from our friends, especially toward the end of Year 1, we start to get really uncomfortable about where we are in life. We’re missing some key ingredients that used to define our conversations. Our friends are telling us about the next mountain they are climbing at work — we’re talking about the last mountain we saw on our umpteenth vacation.  It doesn’t sync anymore.

We don’t feel comfortable talking about the fact that we’re feeling lonely and depressed.  That we’re anxious that we have no flipping clue what we’re going to do with the rest of our lives.

We don’t feel justified in complaining because “we’re successful, damnit!”  We feel guilty talking about how shitty we feel every day even though we’re supposed to feel amazing about the outcome.

We do the only Thing We Know

We realize the money doesn’t replace what we really wanted: Purpose.

We do the only thing we know how to do: We start another startup.  

And for once, we’re happy again.