Four years. Blood, sweat, and tears. And then it all came crashing down.
The startup world loves to talk about failure as a "badge of honor". People talk about how almost every successful founder had multiple failures before their big win.
In hindsight, this is usually true. But, in the moment, you don’t often have the same clarity.
Failure makes you question everything. What went wrong? What could you have done differently? How will you face the people who believed in you?
I spent years building my first startup, RetailMLS (2010-2014). I took money from the people closest to me. And when it didn't work out, the pain was real. Anyone who tells you otherwise isn't being honest.
But here's what I've learned about failure: If you're not moving forward, you're moving backward. You can't change the past. But you can learn from it.
Looking back, I'm actually grateful that I got my failure out of the way early in my career. Those hard lessons led me directly to where I am today — If I hadn't gone through that experience as a founder, I might never have discovered my passion for investing.
Yes, it was a financial loss in the short term.
Yes, it was emotionally devastating.
But it shaped who I am.
The key isn't avoiding failure — it's what you do with those lessons afterward.
And sometimes, the path forward isn't the one you originally imagined… It’s even better.
