I’ve never been this consistently stressed out for this long in my life. Six weeks ago, my business partner and I entered into a verbal agreement with a group of angel investors to fund our company.

The cofounder relationship

This is as hard as they say it is. I am very lucky to have Race, who is honest and humble and smart and motivated and confident. He compliments me well by having a lot of qualities that I don’t. He is a great talker and can go on passionately about our product for as long as you let him. I am criminally understated and often leave out details. We make a good team. But we are very different. It takes a lot of honest communication on both of our parts to get on the same page sometimes.

Before we were funded, I was getting ready to shelf Tealeaf as another failed project. It might be interesting to talk about in an interview, but it wasn’t going to make us any money, I thought. At the same time as I was reprogramming Tealeaf to cut costs, Race was talking to his roommate’s dad who wanted to invest in Tealeaf. He told me he was talking to this guy, but I thought everyone’s roommate’s dad is an “investor” and wants to give you money and it never works out so whatever. During this time, Race sent me a couple ideas for when we got funded. He wanted to buy some new computers and hire his friends to help us code. That email went straight in one ear and out the other because I thought the chances of this investment actually going through were less than none. So, I responded and said “sure”. I didn’t want to argue details on something that would never happen.

Well, fast forward 2 months of investor talks, and it did happen. And now we had other people’s money to be responsible for and figure out how to use in the best way. It was at this point I realized that I had to be honest with Race and tell him that I wasn’t really thinking when I agreed to buy computers and hire people I didn’t know. That was a hard conversation. On the one hand, best business practice is to cut costs where you can, and we really weren’t going to need $3000 MacBooks for everyone. But on the other hand, I had to concede that I had agreed to it in the past and it was my fault for flip flopping and changing my mind. There had to be some compromise. We agreed that we would buy computers but keep them as company computers to potentially sell in the future. We hired his two friends but with the expectation that they are more in an intern type role and not going to get paid like full engineers. We are working it out and making compromises. I am sure that there will be many more compromises to come, with this particular relationship and with future cofounder relationships that I will have.

Bringing in a third eye

Both Race and I are nerdy engineer type guys. We grew up playing videogames way too much and reading math textbooks. I have a little bit of business knowledge from reading an article here and there, but my experience is inadequate for all the business-related things required in a startup. With business being an obvious hole in the Venn diagram of Race and my skills, we decided to bring Wyatt in to do the business heavy lifting. And boy, was that a smart move by us.

I feel bad for all the technical founders out there who have to do it all without a Wyatt helping them. I know that Race and I would drown and probably not even be funded right now if it weren’t for Wyatt. He single-handedly circumvented all lawyers for our angel round by drafting up a Safe Note and corralling all our investors to sign it. He is on the phone with hedge fund managers and machine learning engineers trying to figure out where we should go next as a business. He is helping us design our trading strategy with options trading to maximize emphasis on our AI predictions. Having a business partner who actually knows business is valuable. Who would have thought?

Trading $100k of stock options every day

As a kid playing halo with my little brother, I would always be the one standing far away from the fight safely using a sniper. My little brother was always the one running straight into the fight and dying over an over, taking down one or two enemies with him. I am extremely risk averse. My personal stock portfolio consists solely of ETFs and index funds. Trading with Tealeaf is the exact opposite.

Every day Tealeaf is trading around $100k of options. There is the potential to lose that much money every day. There is also the potential for big gains. By the time I wake up in the mornings, we have usually traded about $20k, and it’s always a surprise to see how well we did. For the first couple days of trading I was sick to my stomach all day. I was so nervous that the code that I had written would mess up and lose all our money. Luckily, we didn’t lose all our money. Only some of it. But that’s the nature of the game. Over the next month or two we are expecting to see a success rate over 50%, meaning some gain in our portfolio. Until then, I am slowly getting more desensitized to the potential huge fluctuations in our portfolio value.