Two months ago I stepped away from Clearscope after a ten-year run. For the first time in a decade, I am sitting in front of a blank page asking a question you rarely get to ask while running a company: what do I actually want to build and explore next?

TL;DR

My next chapter is trading public equities and web3 — pairing an old online-poker temperament with Claude Fable 5 and GPT 5.6 Sol as analysts across an initial $20k live bankroll.

  • A Chipotle burrito funded the first bankroll: In high school I bought my friend Eric a burrito in exchange for a $10 PokerStars transfer. Following the Chris Ferguson bankroll rules, that $10 compounded into six figures by the end of college.
  • The detours taught the economics: Buying into a Dickey’s Barbecue Pit ($19,000 check) proved that rent has no variance; two failed startups and a decade building Clearscope proved how software compounds.
  • Poker transfers temperament, not edge: Bankroll rules become position sizing, tilt control stays tilt control, and most of the job is folding.
  • The desk this time: One AI builds and backtests, a second AI audits and tries to kill the thesis, and every idea gets benchmarked against buy-and-hold.

No fund, no paid signals, no course — just real capital and public receipts. Nothing here is investment advice.

The legend at boarding school

I spent my last two years of high school at the Texas Academy of Mathematics and Science (TAMS), a residential program where teenagers skip senior high school to take a full university course load. You would expect the formative lesson of a place like that to come from the syllabus. It didn’t.

The story that circulated through the dorms was about an upperclassman named Haseeb who played online poker seriously enough to bank house money before ever setting foot at UT Austin. For seventeen-year-old me, that rumor permanently reframed financial freedom. It wasn’t a salary you climbed toward for thirty years; it was a table with a buy-in you could afford right now. I wanted that freedom more than anything in the course catalog.

A burrito for a bankroll

Getting cash onto PokerStars as a teenager without a bank wire was its own puzzle, so I used the dorm economy. My friend Eric had funds on the site, and we executed the least glamorous foreign-exchange swap in history: I bought him Chipotle, and he transferred me $10 on PokerStars.

That $10 came with a strict operating manual. Chris Ferguson had famously turned $0 into $10,000 on Full Tilt by never risking more than 5% of his bankroll in a single cash game or sit-n-go. I gave myself a $10 head start and copied his rules verbatim. At a $10 roll, 5% meant grinding the lowest micro-stakes tables on the internet — sweating nickels and dimes against recreational players while still feeling every swing in my stomach.

A dim home office around 2010: a black desk with a white MacBook and three external monitors showing poker tables and forums, a trackball mouse, and a row of retired cell phones.
The battlestation, circa 2010. One laptop, three monitors. Risk management is the plush one, top right.

The math held. Stake by stake, semester by semester, that burrito money compounded into six figures by the time I graduated college.

Full Tilt Poker screenshot: a $30/$60 Limit Razz table with Chris Ferguson seated with $324, the author logged in as iRAKEyou sitting out, and a tournament lobby listing Chris Ferguson with 5,910 chips.
The graph didn't survive, but this did: me (iRAKEyou, sitting out) at a $30/$60 Razz table on Full Tilt — Chris Ferguson himself across the felt. The guy whose homework I copied.

Poker did more than pay tuition. It installed the operating system I still run today: think in expected value, size every bet to survive a cold run, and treat every session as a single draw from a probability distribution rather than a verdict on your intelligence.

Spreadsheet of sit-n-go push/fold calculations: rows of poker hands with expected-value numbers across stack sizes, and color-coded folding-equity percentages by players left to act.
The actual curriculum: push/fold EV tables from my sit-n-go sheet — expected value by hand, by stack depth, by players left to act. The spreadsheet still opens.

The barbecue detour

What does a college kid do with a fresh six-figure poker bankroll? Naturally, he and a few friends buy into a Dickey’s Barbecue Pit franchise.

A handwritten personal check dated April 25, 2010 for $19,000 to a restaurant holdings company, memo line Capital Contributions, with the bank account numbers covered by a gray redaction bar.
The buy-in, in ink: $19,000 of poker bankroll, April 2010. Memo line: “Capital Contributions.” (Bank numbers redacted.)

On paper, it looked like diversification into real-world cash flow and smoked brisket. In practice, brick-and-mortar food service taught me a single unforgettable lesson: the rent has no variance. Poker lets you fold bad hands, switch tables, or take a week off when the games dry up. A commercial lease bills you on the first of the month whether customers walk through the door or not. We didn’t blow up; we simply realized we were playing at a table where the house rake belonged to the landlord.

That experience convinced me software was the superior game, so I taught myself to code. Even then, markets tugged at the back of my mind as the only arena bigger than poker. I filed trading under someday and went to build startups.

The fork I didn't take

After my first couple of startups died the quiet, ordinary way, I hit the one real fork of my twenties: move to Silicon Valley to join a Y Combinator startup, or sit down and trade full-time.

My dad made the case that operating inside a working technology company would compound my skills far faster than trading alone in a room. He won the argument, and he was right. I joined 42Floors, learned search and growth from the inside, and co-founded Clearscope — which became a ten-year run I’m deeply proud of. Stepping away two months ago finally reopened the road I didn’t take a decade ago.

What transfers (and what doesn't)

Claiming “poker gives me an edge in financial markets” is lazy. Some habits transfer directly; others don’t transfer at all.

  • Bankroll management is position sizing. Same math, same objective: survive a drawdown long enough for positive expectancy to show up. I’ve lived by the 5% rule since my roll was denominated in burritos.
  • Process over outcome. A +EV decision that loses money is still the right play. Poker drills that distinction into your nervous system one river card at a time; markets liquidate anyone who confuses a lucky win with skill.
  • Tilt recognition. Financial markets are purpose-built to manufacture emotional tilt. Poker charged me cash on the spot for every tilted click until I learned to close the laptop.
  • Discipline to fold. Most of winning poker is folding mediocre hands pre-flop. Most of swing trading is sitting on your hands until the setup is clean.

What doesn’t transfer is domain edge. Knowing how to lose gracefully says nothing about FOMC rate paths or semiconductor inventory cycles. Temperament keeps you in the game, but it isn’t alpha — a fact I already proved to myself when I had three AIs backtest ~310 quantitative strategies and watched simple buy-and-hold beat almost all of them after realistic transaction costs. The benchmark remains undefeated until proven otherwise.

The desk this time

What makes the experiment worth running now is that I’m not grinding solo. Claude Fable 5 and GPT 5.6 Sol sit on the desk as full-time analysts — one researches signals and writes the backtest code, while the other audits the math and tries to falsify whatever the first built. Our house rules from the vibe-trading experiment remain non-negotiable: no LLM ever touches live order execution, auditors must reproduce numbers from raw data rather than trusting prose summaries, and every strategy is benchmarked against doing nothing.

I am 100% in exploration mode: no outside capital, no paid Discord signals, and definitely no course. Just the operating principle behind everything else on this site — put real skin in the game, log the theses in public, and keep every receipt.

Robinhood portfolio overview on a phone with the dollar amounts hidden, showing a green year-to-date chart trending up and to the right.
Where the experiment lives: the book, mid-July 2026. Numbers hidden until there's something worth showing.

Seventeen-year-old me heard a dorm-room legend about a kid who bought his freedom at an online poker table. It took a Chipotle burrito, a six-figure grind, a barbecue franchise, two dead startups, and ten years of Clearscope to sit back down at the tables with my own chips.