Pitch to Plunge

Four investors waited in white chairs on the deck. Among them were Chris Camillo, a self-taught investor who co-founded the investing community Dumb Money; Bill Perkins, who founded the energy hedge fund Skylar Capital and wrote the bestseller Die With Zero; and Di-Ann Eisnor, who started Waze's US office.

The format had one rule. Every founder pitched the same four investors, and anyone who walked away with four noes got dunked into a tank surrounded by sharks.

I pitched first, so my opening line opened the episode: “What if you could play a video game while running?” Then I told them why I was building it. Running helped pull me out of depression as a teenager, and most people who start running quit within weeks.

Ippo is my answer. On an Apple Watch, a creature appears mid-run, the watch buzzes and you sprint to catch it, and the effort you put in raises the pets you collect. A classmate ran a live demo on the deck, and I asked for $25,000.

Chris Camillo made the offer: $25,000. Bill Perkins said he'd match it, and the two agreed to split it, $20,000 from Chris and $5,000 from Bill. I accepted on the spot, standing on the deck between them. It was the first deal of the episode.