An Introvert Haggling With Billionaires

It can be hard explaining to people what I do at work. Betting on horse races, building a tech startup, something with chat-bots, raising funds from VCs, working with a rag-tag team of astrophysicists and poker players from Cambridge. A lot of my friends have their own funny spin on what I do for a living.

These days it seems like I’m always on the phone haggling with billionaires, and along the way I get myself into some pretty unlikely situations. Like that time I suggested to one of them to toss a coin for an extra few million dollars in valuation for our startup (he didn’t take that offer, but I was getting a bit desperate).

Just a few hours ago I was negotiating with the right hand man of a guy who made a fortune by betting on football and now does something a lot like in the movie Moneyball: he owns a premier league football club! These guys will be investing in our Hong Kong horse racing betting strategies. Late last week I was speaking to investors representing another British billionaire and they said “sorry Tom, we’re out of cash because we’re bidding to buy Chelsea F.C.” What??!!

That’s our bread and butter at Seamless: building fully automated systems that predict and bet on the outcomes of horse races. You can listen to Will recounting some good anecdotes in this podcast if you want to learn more about our adventures in sports betting.

Most of my time these days has very little to do with horse racing however. Now I’m all in on Chai, a startup building YouTube for AI chat-bots. It’s Will and me working on this again, alongside two of our colleagues Rob and Ziyi.

Earlier in the week we received our first investment of 250,000$, valuing our business at $8.5 million. Less than we wanted but a good start.

That investor is a billionaire member of the PayPal mafia, the original team that built PayPal and went on to build LinkedIn, YouTube, SpaceX, Affirm along with a few other multi-billion dollar businesses. Feels like we’re part of the club now!

All this haggling for investment, negotiating on company valuation, and hustling to get in the room with top investors has been a wild ride for an introvert like me. One of the great things I learned along the way is Chris Voss’ approach to negotiation and difficult conversations. I must have read a dozen books for work in the last quarter, and Voss’ Never Split the Difference was the most helpful. He is a former hostage negotiator for the FBI and gives his tips and tricks for getting people to give you what you want. I don’t like talking, arguing or conflict, and the last few months have been a real trial by fire. You learn by doing, they say, well by gosh I have learned a ton.

I turn 24 in two weeks and things only seem to be getting crazier: we plan to move to California and Chai is growing better and faster than anyone expected. It looks like we’re in for a great adventure and I’m excited. And if it all goes south, the real point of all this was to take some good risks and learn, so I’m happy.

If people like this post I’ll write some others with some more mad stories from work because there’s a lot more where that came from 😛

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This post was previously published on MEDIUM.COM.

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