As a 4th generation entrepreneur, hustle is in my DNA. Since elementary school, when I'd haggle at the baseball field snack counter and trade my way to walking home with $5 or $10 and free food, I've been in love with the game of entrepreneurship. I believe one of the biggest tells for a true, die-hard entrepreneur is their answer to the question: "What are some of the strangest ways you've made money?"

It's fascinating to hear people's replies. Airbnb's founders selling "Obama O's" cereal to keep their startup afloat. Or Steve Jobs and Steve Wozniak who started by selling illegal gadgets that allowed users to make free long-distance phone calls. These scrappy beginnings often hint at the innovative thinking that leads to bigger successes.

In that spirit, here are the five strangest ways I've made money:

1. Arbitrage Opportunities In Designer Snakes

I discovered an arbitrage opportunity in the designer green tree python market, where breeders spend $5k to $10k+ on snakes. Many top breeders now run waitlists due to demand outweighing supply. I simply sign up for top positions on these waitlists, choose the most desirable snakes in each clutch (bold yellow diamonds, minimal designs, dark red color), and then resell that snake to another buyer - without ever receiving it. This virtual snake trading has netted me over $10k.

2. Duct Tape Wallet Empire

In middle school, boredom in class one day led me to create a wallet out of duct tape, which I sold to a classmate for $1. This evolved into a micro-business of "personalized duct tape wallets." Students could choose their sticker and even have their name on it (wooow). I expanded into different colors of duct tape, charging more for blue or electrical tape versions. Looking back, I'm still amazed anyone actually paid for these!

3. The Jiu Jitsu Bet

I started betting higher belt jiu jitsu players $5 that they couldn't tap me out with certain moves. While not entirely my idea (I stole it from a training partner at Method MMA), I realized it was easy to sell on someone's pride. A brown belt isn't going to turn down a challenge from a purple belt. This strategy didn't always work in my favor - I got smashed by some good athletes - but I've made about $180 from it. More importantly, it's significantly improved my submission defense and typically results in good scraps + highly realistic training scenarios that help you get better faster.

4. The Unsolicited Roof and Window Salesman

During college, I worked for HCR, insisting on being a salesman rather than a lead setter despite my age. I became the youngest salesman in company history and graduated training in Vienna, VA faster than 98% of anyone else.
Within two months, I was Maryland's top salesman, selling roofs and windows to people who typically didn't even want them.

5. Data-Driven Automated Investing

This isn't weird I just couldn't think of anything else so I'm shilling my company.
Since middle school, I've been experimenting with automated investing, following in the footsteps of legends like Kevin Davey, Ernie Chan, and Jim Simons. By 25, I've made enough to uncomfortably retire, which allowed me to bankroll my current company, Surmount, until we secured professional investment.

These experiences have all contributed to my entrepreneurial journey. They've taught me valuable lessons about identifying opportunities, understanding human psychology, perseverance, and the power of automation and data.