I Was Fired From 3 Startups in One Year

Photo taken in 2015, my year of sorrow and collapse

2015 was a rough year for me.

I didn't start it thinking I’d be repeatedly hurling myself against a wall, but that's what ended up happening. I banged myself into new shapes and watched parts fall out along the way. The whole time, I kept thinking, Silicon Valley embraces failure, right?

I heard these words a lot. It was repeated so often that it was a cliché. As I looked deeper, though, and I found that the people talking publicly and glowingly about failures were often company founders looking back from the comfort of success. I realized soon enough rejection was a much less popular topic.

Rejection, the dirty little not-so-secret.

But that's why I'm writing about rejection. It's something we will all face in our lives, and after losing three startup jobs in one year, I'm an expert. The overlooked topic now fits me like a strange, mismatched glove.

I never thought I'd have three different full-time, permanent jobs in one year. Losing those jobs was tough on me and my family in ways that make “failure is good” seem like the reductive homily on a greeting card I’d happily shred, and strongly affected my mental health.

I want to share what I learned from rejection in 2015. It was a year that showed me startups at their best — what amazing potential for growth — and their worst, where employees are barely given a first chance to succeed, much less a second, due to the focus on the short-term.

When I began 2015, I'd been at large media companies for over a decade. I felt stale and ready to tackle a new set of problems.

Startup #1

If startups were people, Startup #1 was the cool kid with great design sense who promised you everything would be better. You know, the one who talks about his fixie and goes to the new bar before it officially opens. I was the oldest person at Startup #1 and by far the least cool, but I knew the SF food and media scene. Everyone was nice to me despite my slow adaptation to Slack giphy banter.

We were a small team — seven guys plus me in a co-working space in the Tenderloin District. We released our first app in October 2014. It was meant to be first in a series of apps, but January arrived and there were still no plans for app #2. More importantly, there was no second round of funding. My job, and the fate of the company, felt extremely tenuous. When I got the “you around?” on Slack first thing Monday morning, January 5th, I knew what was coming. I headed to Showdogs, a Tenderloin hot dog restaurant, braced to have an uncomfortable good-bye conversation with the two co-founders, who were facing the prospect of repeating the same awkward conversation over and over that day.

Startup #1 Takeaway

Just because the whole company was disappearing, it still felt personal. Despite knowing that it had nothing to do with me, for the next couple weeks I found myself listening to breakup songs and moping around the house.

Startup #2

Two months later, I joined Startup #2, which had everything going for it — an experienced team, a strong mission, and ample funding with good prospects for more. “Could be a great new relationship for me,” I thought. Startup #2 was a cool kid who had grown up and stashed his skateboard in the garage but still had lots of energy, with lots of ideas and the experience to make them happen.

This startup had some money and knew how to spend it. It would pay for meals, laundry, and even housecleaning so I’d have less to worry about (which of course means more ability to focus on work). Initially, our office was a small repurposed apartment in the Castro. It was so small that to have phone conversations without disturbing each other, we made muffled calls from the coat closet. But soon enough we moved to a nice big office down the street.

Startup #2 was promising, but as with most relationships, things got more complicated as time went on. Five months in, Startup #2 decided I wasn’t who it thought I was at the beginning, and I was let go on July 3 — not the kind of independence I was hoping to celebrate that week.

Startup #2 takeaway

Startups grow quickly, and they change quickly. I still don’t exactly understand why it was that I was fired. But I did understand that when my boss said, “You don’t seem happy,” he was right. A week after I was fired, I was diagnosed with generalized anxiety disorder by a neurologist I went to for migraine treatment. It was an easy diagnosis for her, she said, because in her practice she sees many tech professionals (anxiety turns out to be a surprisingly common affliction in the tech industry, as well as in other high-risk, high-reward professions). Figuring out I was experiencing anxiety took me 39 years. The enormity of the discovery softened the blow of my professional rejection, though it still aches like an old war wound some nights.

Startup #3

I met Startup #3 in late September through a mutual friend. Small, deeply customer-focused, and (gasp!) profitable from the start, Startup #3 seemed like an anomaly in Silicon Valley (in a good way).

“This one really is different,” I said to myself.

I’d describe Startup #3 as self-made and down-to-earth. Startup #3 was (and is) genuinely committed to building tools that users need and want, even if the tools aren’t sexy. For example, Startup #3 cares about making your Aunt Verna Mae in Kansas feel comfortable, even though it’s her first time on this newfangled internet.

Our first month together was great — or so I thought. Then I got my very first feedback: a sheet of paper detailing misunderstandings and shortcomings. It took a few more weeks for Startup #3 to figure out that it didn’t quite know what it was looking for when it hired me, but now it did: someone with a few traits that I just don’t have.

Final Takeaway

The worst experience — being fired two weeks before Christmas and after only two and a half months on the job — led to the best takeaway (third time’s the charm!). I didn’t take it personally this time. It wasn’t a fit for either of us. Rather than carry the awkwardness of the moment, I took the opportunity to ask the founder detailed questions about my performance. Her answers helped me feel like I really understood the reasons behind the poor fit. That left me free of the nagging doubt I’d had after the prior two jobs, the constant speculation of “What if I had…” or “Why…?”, which can keep a person up at night.

What I Learned From These Startups

Losing a job isn’t necessarily a failure, nor a cause for embarrassment.
I learned a lot about the people around me by how they reacted to my rejection.
I’m married to the right person; not everyone could handle what I’ve been through. At every step he’s given me perspective and made my experience better.
The ability to depersonalize rejection — even when it is personal — is a super power I’ve been granted by my year of startups.

The risk of startups isn’t just whether they succeed or fail. Just as risky, for people working there, is that your value is dependent upon the whim of a very small group of people, and often just one. They hire quickly; they can tire quickly; they fire quickly. It may seem cruel, and sometimes it is, but there’s a coldly rational reason for it. Tech is a cutthroat industry where getting to market and getting funding is crucial. This puts a lot of stress on founders, who then may make rash decisions as a result.

Under pressure, some coal turns into diamonds, but a lot of it just turns to dust.

Does everyone who goes through this volatile world come out more resilient? We’ll know when the rejection of workers is seen as being as sexy as the failure of CEO’s.

If failure helps a person learn, then perhaps dealing with rejection helped me become braver.

I don’t relish my head’s recent intimacy with the wall. But I’m still intact. I’m less scared about work than I’ve ever been. I’m not even scared about having you read this, and having my name right next to the word REJECTION. Considering how banged up I am, that’s saying a lot.

Originally published Dec 28, 2015 // Last edited Jan 19, 2023