250 or 60 to 4

Welcome back. Been heads down building a side project for two straight weeks, excited to be launching it in beta in the next week or so. More details on that in a few months.

Today we are going to talk about a small remodeling of this newsletter. It’s going to be short and all over the place, so good luck following along.

For those don’t know my background, I became interested in finance when I first played the stock market game in 9th grade. I came in last place, but I also placed 342 trades in 3 months. The next closest was around 60. I learned two things quickly when I was 14, first was that I loved the markets and finance. Second is that I am a god awful day trader.

Flash forward to college, and my interest switched toward the private markets. I worked for multiple private investors and startups throughout college and loved finding early stage companies to work with or write about.

To this day, I still follow the private markets and the startup world very closely. Over the last 7 or so years I’ve spent in this space, I have discovered some truly incredible companies and investment ideas very early on. Yet, due to some pretty dumb rules by the SEC, I’ve only been able to act on a few of them.

Just recently two of the startups I’ve followed from the early days, Rogo AI and Titan raised massive funding rounds.

I would have invested in Rogo AI at around a $48m valuation. They recently just raised a round at $350m valuation. That would be a 6.29x return.

I would have invested in Titan at roughly a $50m valuation. They recently raised a round at $1b valuation. That would be a 20x return.

Running these what-if calculations suck. Now obviously, just noticing these companies doesn’t mean you get an allocation, but that fact doesn’t make this hypothetical fun, so let’s ignore it.

250 or 60 to 4

So with my exposure to these early-stage companies, as well as what I believe is a small edge on new investment ideas, what could I do if I actually had a fund? What if I could invest $1m, or $50m, or $100m into ideas? What would that look like?

Well, that’s what this newsletter is going to transition to. Each week, I will present a new investment idea of what I would do if I have either $250m, $60m, or $4m to invest in a new idea. 

Alright, so why the random numbers? Well, I listen to music for probably about 60-70% of my workday. I had this idea when listening to the song 25 or 6 to 4 by Chicago, one of the most successful bands in the rock era. So to be creative and pull from that, we are doing $250m, $60m, and $4m.

Even better, we are going to be tracking all these ideas in a new application I build in the last 30 minutes (thanks AI!).

Looking forward to this new direction, and hopefully some of them will even be public market investments so I can actually put my money where my mouth is.

Alright, quick version, time to pack for Charleston. I’ll see you next week.

Song of the Day

I live in Fairfield County, CT my entire childhood, so obviously my family had a 4-door jeep. One of the best times was after high school driving with the top down listening to this song in the summer. To this day, it is still a banger.