Startup Days: A Lifetime in a Few Years and Then It’s Over

It’s Friday so … I came across a FB picture of some old startup swag this week, and I stared at it for a few minutes.

There’s a very specific kind of nostalgia that comes from startup life. It’s not like anything else – not being a VC, working in a big company, or anything else I’ve done in my life. It’s a mix of college, bootcamp, and a lifetime of experiences, all jammed into a few intense, defining years. And then its over.

My startup was like that. Dan Sommer, Ajay Shah and David Elkins and I started Handshake.com as a B2C site connecting small service businesses and consumers. (Airbnb is trying this again now 😉 Then we pivoted to a B2B scheduling software tool (SaaS before SaaS!) but a bit too little, too late.

I moved cross country. Lived the Cali life. I learned more business lessons in those three years than I have in almost any other stretch of my career.

We raised too much, found too expensive of an office space (my mom helped pick furniture), hired too fast, spread ourselves too thin, but we didn’t have Product-Market fit. We brought in Senior Execs too early and then strategic capital before we figured out the right partners.

I learned the importance of focus. We spent too much on Yahoo! ads. I took a Spin Selling course. Most importantly, I learned how to manage people of all ages – even when I was still figuring it out myself.

But then everyone moved on. No big reunion. No goodbye tour. Just a fade-out. People I spent 15-hour days with, traveled with, laughed and argued with – and then it’s done.

At one point, we were so close that on a road trip seeing customers, I mistakenly wore my colleague’s pants and he wore mine!

It was a crash course in everything – product, leadership, humility. And then, just like that, it was over. But I wouldn’t trade that experience with those people for the world! It helped make me the investor and partner I am today.

Those years were chaotic and exhausting, but deeply formative. I didn’t realize it then, but I was learning the foundations of everything I still use today as an investor.

It’s amazing – startups are short chapters, but they leave lifelong imprints.