Losing Yourself at the Exit (Transmission #353)

For five years, my entire identity and self-worth was tied to my travel startups: Oh Hey World (2012-2013) and Horizon (2014-2017).

Entrepreneurship can feel a lot like Cast Away. Everything falls on you, and nothing else matters. I worked day and night. Friends, family gatherings (including funerals), dating, hobbies—everything took a backseat. All I thought about was my company.

Then, poof. Horizon shut down.

The weight of product updates, bug fixes, team morale, customer growth, and endless decisions evaporated overnight. But so did the thing that gave my days structure and meaning.

No emails. No customers. No partners. No team. 

Just a black hole of nothingness.

Nobody talks much about what happens after the startup ends. The fundraising decks disappeared. The product roadmap disappeared. The mission disappeared. 

What was left was figuring out who I was without the thing that consumed my life.

After shuttering Horizon, I spent a year in a dark place while processing one of the hardest emotional setbacks in my life.

Without my startup, I felt like I had lost my purpose. I couldn’t wrap my head around the reality that life existed beyond the startup, because for years, it hadn’t. 

The sorrow of failure created a void I had never experienced before. It took years to truly get over the loss of personal capital, burnout, self-pity, and not being able to give my mother a clear answer to the question, “What are you doing?” An emptiness that, still to this day, is hard to describe.

I carried a lot of shame about failing publicly. I was financially strained after funding the company myself. And while I didn’t have investors to answer to or employees whose livelihoods depended on me, I still had to confront a question I wasn’t prepared for:

Who was I without Horizon?

THE COPING PROCESS
My friends didn’t understand what I was going through, nor did my family. And, thus, I held it all within.

At the time, I had no peers to talk to. No understanding of the power of being seen and understood by people who had lived through something similar. 

What I needed wasn’t advice. I needed space to process what happened—and people who understood the weight I was carrying. Peer Passage Colorado is exactly the environment I wish I'd had when Horizon came to an end: a safe space to be around people who had stood in my shoes.

I didn’t realize it at the time, but I was depressed. The founder blues you might call it.

Fairly soon after shutting the company down, while looking for a “real job,” I ended up starting Geek Estate Mastermind. Suddenly, I had a new “baby” to tend to. It’s the path many take: dive into something new immediately. 

It eventually became clear that being the public face of a global internet company wasn't my life's calling. Getting to that realization took years. Marc Davison pushing me to tell my story at Turn On was a big part of that process for me—six years after shutting the company down.

What I should have done is not spend years holding that emptiness alone.

THE POWER OF PEERS
In hindsight, I can tell you with certainty that it was a mistake not to spend time processing the end of Horizon. Suppressing my feelings didn’t make them go away. It just pushed them deep down, but they would come back with a vengeance years later. I had to deal with my shame at some point.

I’m far more self-aware and emotionally mature than I was a decade ago. I realize bottling up my feelings isn’t healthy. Today, I have a therapist. I lean into absolute truth in safe places. I have a small group of friends who I share everything with. I belong to a peer mastermind group of community builders. 

In short, I have outlets—personal and professional, and some that span both—that I didn’t have back then. And I’m not shy about being vulnerable. I’m not alone.

Most of the proptech mergers and acquisitions I’ve heard about in recent years are firesales of distressed assets. Not lucrative outcomes for founders. Few are riding off into the sunset with millions in the bank. 

The Horizon/Oh Hey World outcome was not lucrative. Far from it. Regardless of the financial outcome of moving on from your “startup baby,” you have to deal with losing the thing at the center of your professional and, often, personal life. 

Who are you then? How do you move forward?

Entrepreneurship stranded me on an island. For years, I convinced myself I had to navigate it alone. 

I was wrong. 

I just wish I had found my Wilson sooner.

[Thanks to Bryan Copley and Jesse Garcia for feedback on this article.]