On Lightspeed

Before deciding to invest in Cheddar, Jeremy suggested that I join Lightspeed as an investor. This was incredibly flattering and a bit mind blowing. It was certainly out of the box thinking at a time when people were mostly pinging me about operational and revenue roles.

I came out and met with the partnership. We talked about the portfolio, my experiences, their experiences, and the ideas around what would become Cheddar. People tend, in general, to give me a hard time about most of my ideas, especially the new ones. The Lightspeed team wasn’t like that. They wanted to talk about ideas and chess moves with regard to how the industry would play out.

In my years of knowing Jeremy, and the meals and coffees, we’ve always had conversations around, “what happens if this dynamic plays out,” “what would the incumbents do,” “how could a startup do a flanking move,” etc.

In fact, when I presented the notion of “live video” as the next big thing in media, Jeremy said “yes, and…” at a time many others said, “live doesn’t work, you should do short clips with text subtitles on Facebook.”

We have a lot of hard work ahead with Cheddar, but Lightspeed sees that the only way to build the future is to make a bet on where the puck is going or may be going, as opposed to where it is or was. This is how the firm ended up backing Bonobos, Nest, the Honest Company and especially those in media like Mic, Beme, and Snapchat (and some exciting unannounced ones as well).

The firm has been fast, direct, and helpful with me from day one. Jeremy and I agreed to terms on a single phone call, and the funds were in the bank in 4 weeks. When I have a question or an idea as the founder and CEO, Jeremy gets it done and occasionally has a better idea, which he makes happen for me. With that said, 90% of emails are me asking for his approval as a board member, and him writing back in 10 minutes with “ok,” “yes” or “sure.” With that said, in the 5% to 10% of times my ideas are wrong or a decision is flawed, he calls me out quickly and advises an alternative.

And so given how this is how I want to operate as an entrepreneur, I’m proud and honored to be a Venture Partner with the firm and bring this same style to media and tech startups in NYC.

That role starts today. Ping me if you’d like to learn more about Lightspeed.