My $5M “Mistake”: When Betting on Yourself Doesn’t Work Out
All the gurus tell you to bet on yourself. But what happens when it doesn’t work out? Four years later, here’s my answer.
I wanted to start off this blog by writing about something raw and real.
Over four years ago I left my job as an individual contributor in cybersecurity to start my own company. Just a couple years earlier I’d sworn that I’d never do that because the uncertainty and stress weren’t worth it. But there I was on my last day, saying goodbye to great colleagues and “jumping out of a perfectly good airplane.”
What I didn’t–couldn’t–know was that that decision would end up costing me more than $5M.
I’d been in cybersecurity for a while by then. I started in an R&D lab before moving to the Bay Area, pulled in by the excitement of startup life and the so-called “lottery tickets” of early-stage company equity. I still remember the day my stepdad–a lifer at one company in one small town–essentially yelled at me for leaving my first job to pursue something as unknown as a startup.
But it worked out.
I joined early enough to get meaningful equity. I loved what I did and the people I worked with (it’s still the greatest group of people with whom I’ve had the pleasure of working). And eventually, the company was acquired.
At the time, I was already planning my exit. I’d made up my mind to start my own thing. The acquisition didn’t change that, partially because I had very little room to grow internally, and I wanted to see if I could actually build something on my own. I waited two quarters to vest 1/8th(!) of my new equity package, then left.
Someday I’ll write in more detail about my company-building experience (where I got it wrong, and where I got it right), but suffice it to say that I learned an unbelievable amount. The phrase “drinking from a firehose” doesn’t do it justice–I was drinking from Niagara Falls.
Many of those lessons were huge growth opportunities for me, and I honestly don’t directly regret having started my own company. One of the biggest reasons why I decided to start something was that I didn’t want to look back and say “what if?” at the end of a well-paid but otherwise unremarkable career.
I definitely achieved that.
But it came at a significant cost.
To add insult to injury, after I decided to shut down my first company due to a toxic cofounder relationship, I had a chance to go back to the acquired company. I could’ve rejoined and started vesting right where I left off.
But I said no. Why?
Because my cofounder (who was not full-time) slowed me down, causing me to take longer than I should’ve to discover that product-market fit was really not there. And around the same time, I had a motivational meeting with a founder friend of mine who went through a similar situation a few years prior, pivoted to start their company solo, and ended up building something reasonably valuable. They encouraged me not to throw in the towel just yet and to bet on myself again.
So I did. And honestly, it almost worked out.
The second company I started did have some early success and was growing. Simultaneously, I landed some critical channel partners that opened up a lot of promising opportunities. But after about 18 months of building (and a few tough breaks on deals), I decided that I couldn’t scale earnings to the level I needed. I even had a few acquisition conversations, but eventually those fizzled.
Across the two companies, I had been bootstrapping for nearly 3 years, and I wasn’t comfortable continuing to burn up our savings. So I joined a different cybersecurity company.
I gained many things, but financial success was not one of them.
They say “pics or it didn’t happen,” so here’s a (redacted) picture of my stock holdings that I gave up back when the price was less than 25% of its current value (roughly late 2021):
Everyone says that two things in life are certain: death and taxes. But I’d argue that there’s a third: uncertainty.
What looks like a great move at the time can turn out to be an expensive mistake just a few years later, just as something that feels terrible at the time can turn into a great opportunity. Hindsight is 20/20, but the future is unknown.
From personal conversations with friends, people I know through Internet forums, and many of the news stories I see every day, I’m confident that there are a lot of people in the world right now living with an incredible amount of uncertainty. It’s not just about money, though, but about relationships, identity, and even where to live.
I’m starting this blog for you.
For those asking questions like:
“What will work look like in 5 years?”
“Should I spend money and enjoy now or squirrel away as much as possible?”
“Will things ever feel certain?”
My hope is that “Certainly Uncertain” becomes a place for sharing, commiserating, and finding community in our uncertainty–even if we don’t always have the answers. And while I’ll (at least at the beginning) keep my writing roughly anonymous, know that there is a real human at the other end of these posts, typing away at a keyboard about real challenges and uncertainties in their own life.
great read - Uncertainty being a certainty like death and taxes is a great point.