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How Monkey Tilt Founder Sam Kiki Took Down a $255K Pot on High Stakes Poker
Inside the poker moment that brought a tech billionaire and a crypto founder to the same high-stakes table.
When most people think about DoorDash, they think about late-night tacos, hungover brunch deliveries, and the little red bag showing up at their door. What they probably don’t think about is one of its co-founders sitting across from a fast-rising crypto casino founder, pushing $95,000 worth of chips into the middle of a poker table.
But that’s exactly what happened when Stanley Tang, the billionaire behind your favorite food delivery app, went head-to-head with Sam “Señor Tilt” Kiki, the founder of MonkeyTilt in a quarter-million dollar pot.
On Monday, January 5, PokerNews published a recap of Episode 1 from High Stakes Poker Season 15, which premiered on PokerGO last month. The episode featured Tang and Kiki squaring off in a $500/$1,000 no-limit hold’em cash game alongside comedian Kevin Hart and poker pro Andrew Robl, with $1.5 million on the table before the first card was even dealt.
The hand unfolded fast.
According to the outlet, Kiki raised to $7,000, and Tang — holding A
J — bumped it up to $30,000. Kiki called Tang’s three-bet, and the flop came Q8Q
, giving Kiki trip queens and Tang the nut-flush draw. The turn didn’t complete Tang’s flush, but after Kiki fired $35,000, Tang shoved for $95,500 as a semi-bluff. Kiki called, they ran the river twice, and neither runout helped Tang. Kiki scooped the full $255,000 pot.
What set this showdown apart is that both players are entrepreneurs who built massive companies from the ground up — one in consumer tech, the other in the rapidly evolving world of crypto gambling.
Tang co-founded DoorDash back in 2013 while he was still a junior at Stanford, launching it from a dorm room under the original name Palo Alto Delivery. Fast forward to 2024, and DoorDash made its debut on the Fortune 500 at No. 443, pulling in $8.6 billion in revenue. Tang’s current reported net worth sits around $1 billion.
Kiki, meanwhile, has been carving out his own lane. According to Forbes, the Las Vegas native earned a neuroscience degree from Amherst College before climbing the corporate ladder at MGM Resorts and Caesars Digital. He eventually launched MonkeyTilt, a crypto-integrated gaming platform that has raised over $50 million from investors like Pantera Capital and Polychain.
In a 2024 interview with Fortune, Kiki described his vision: “I’m looking at the future as you log in and you’re hanging out on the site for a few hours, talking to your friends. You’re gambling together. You’re having fun the same way you would in Vegas.”
That vision didn’t stay theoretical for long. Fortune reported that the platform moved fast out of the gate, pulling in roughly $200 million in monthly betting volume within its first eight months online — a pace that helped attract heavyweight backers like Pantera Capital and Polychain Capital.
