He Made Millions Playing Poker…Then His Side Hustle Did Even Better

EPISODE · Mar 21, 2026 · 1H 21M

He Made Millions Playing Poker…Then His Side Hustle Did Even Better

from Table 1 Podcast · host Table 1 Podcast

Play Poker With the Table 1 CommunityNew players on Phenom Poker can get a 200% deposit bonus up to $2,000.Sign up here:https://play.phenompoker.com/register?r=Table1OR… come play with us in Las Vegas at Table 1https://table1.vegasTaylor Caby didn’t set out to change poker.He set out to get a job.Finance degree.University of Illinois.Do well in school → get hired → make money.That was the plan.Poker was just something on the side.A few home games.$20 buy-ins.Messing around with friends.Then online poker showed up.And the first problem?He couldn’t even deposit.He asked his dad to use the credit card.Dad said yes.Mom said no.So for six months… he played freerolls.Grinding for pennies.Eventually he figured it out and loaded about $30–$35 online.That was the bankroll.Six months later?He wins a tournament for $3,000.By the end of the year:He’s made $50,000 playing online poker.In college.And within another year…He’s playing some of the biggest games on the internet.Then something bigger happened.He realized something nobody else had figured out yet:People weren’t losing because they were unlucky.They were losing because they didn’t understand the game.So he started recording how he played.Not as a business.Just something to put on a resume.That became CardRunners.The first real poker training site.And almost overnight…Players got better.Games got tougher.And suddenly…People started saying he was ruining poker.From there:♠️ Built one of the most influential poker businesses ever♥️ Played high-stakes online against the best in the world♦️ Partnered with Full Tilt during the poker boom♣️ Watched it all collapse on Black FridayAnd here’s the part most people miss:He saw it coming.The whole thing, in his words, “felt like a mirage.”Then he did something most poker players never do.He walked away.Built a DFS company.Lost money.Went back to gambling.Then built another business…Establish The Run.Same idea as CardRunners.Different game.In this episode of The Table 1 Podcast, Taylor joins Art Parmann and Justin Young to break down:♠️ Turning $35 into $50K (and beyond)♠️ The early days of online poker (and how soft it was)♠️ Building CardRunners from a dorm room♠️ Why players said he “ruined the game”♠️ The truth about Black Friday♠️ Starting (and losing money on) a DFS company♠️ What he learned about business vs poker♠️ How Establish The Run was builtIf you want to understand how poker evolved from chaos… to strategy… and what it actually takes to build an edge twice… this episode is a must-listen.Show Notes:0:33 — Intro & early poker impact2:00 — Childhood & early competitive mindset5:30 — Discovering poker in high school10:00 — College & finance path15:00 — First online poker experience17:00 — Grinding $5 sit-n-gos22:00 — First big tournament win23:00 — $50K in college25:00 — Moving into high stakes28:00 — Heads-up battles & rivalries31:00 — Origin of CardRunners34:00 — Building the business38:00 — First big success (and shutdown scare)40:00 — Scaling CardRunners47:00 — Transition into business focus50:00 — Attempting to sell to Full Tilt53:00 — Black Friday impact55:00 — Pivot to DFS (DraftDay)59:00 — Why DFS failed1:03:00 — Playing DFS professionally1:05:00 — Starting Establish The Run1:12:00 — Business today1:20:00 — Closing thoughtsConnect with Taylor CabyTwitter / X: https://x.com/TaylorCabyCome Play Poker With UsIf you're in Las Vegas and want to play in our Table 1 private game at ARIA, you can request a seat here:https://table1.vegasPlay Online With UsJoin us on Phenom Poker and get a deposit bonus:• Up to 200% bonus on your first deposit (up to $2,000)• Use our link to sign up• Deposit using USDTLink: https://play.phenompoker.com/register?r=Table1

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He Made Millions Playing Poker…Then His Side Hustle Did Even Better

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