“With my investment, you’ll become the largest dating site in the world. He was willing to make a very large investment in our company, and he went on to discuss the details of how such an arrangement would work. When I got there, he told me he thought what we were doing at SNAP Interactive was great-we had a great product, we were growing very fast, and they wanted to be part of it. This venture capitalist asked me to fly out to Silicon Valley to meet with him, so I obliged him because this could have meant a whole lot of money coming our way.

In the midst of this period of Facebook-driven explosive growth, a venture capitalist approached me with an offer that I couldn’t refuse-but I did. As one of the first Facebook apps, we were able to grow at a truly explosive rate, all without making major changes to our product’s core functionality. In hindsight, this was obviously the right choice. We transitioned the app entirely to a new platform that had just begun to support apps-Facebook. We took our dating app, which at the time was a standalone website with modest traction, and tore it all down. The $10 Million Check I Left on the TableĮarly on in our company’s history, we made a gutsy call. I walked away from a $10 million check at a critical moment in our company’s history, and while we were still profitable and still successful, it’s hard not to think about what could have been. You can read plenty of articles that make good arguments against fundraising when you don’t need it to be profitable, but I have a story from the other side. It involves something many founders struggle with-fundraising. However, I still have plenty of regrets over decisions I made, and one in particular stands out as the most poignant. My company, Snap Interactive, was at one point worth well over $100 million. Nonetheless, the thought is there from time to time-” What if I’d done it just a little bit differently?” Obviously, successful founders don’t let these regrets haunt them forever, and they don’t dwell on them endlessly. The reality is this: every successful founder regrets at least one major decision they’ve made.Įvery founder, in their weaker moments, thinks about what greater heights their company might have reached if they’d done something differently. We look at great founders like Brian Chesky (Airbnb), Neil Blumenthal (Warby Parker), and Kevin Systrom (Instagram), and picture perfectly confident, regretless people. Most of us have a misguided view of successful founders.

Explosive growth cliff lerner