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March 21, 2026 He Made Millions Playing Poker…Then His Side Hustle Did Even Better

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Taylor 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 Friday

And 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 built

If 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 impact
2:00 — Childhood & early competitive mindset
5:30 — Discovering poker in high school
10:00 — College & finance path
15:00 — First online poker experience
17:00 — Grinding $5 sit-n-gos
22:00 — First big tournament win
23:00 — $50K in college
25:00 — Moving into high stakes
28:00 — Heads-up battles & rivalries
31:00 — Origin of CardRunners
34:00 — Building the business
38:00 — First big success (and shutdown scare)
40:00 — Scaling CardRunners
47:00 — Transition into business focus
50:00 — Attempting to sell to Full Tilt
53:00 — Black Friday impact
55:00 — Pivot to DFS (DraftDay)
59:00 — Why DFS failed
1:03:00 — Playing DFS professionally
1:05:00 — Starting Establish The Run
1:12:00 — Business today
1:20:00 — Closing thoughts