Tech founders competed in a startup's glitzy $100,000 poker tournament. I took them on.

• Monaco sponsored what it billed as "the largest founder poker tournament of all time."
• The AI startup, which recently emerged from stealth mode, offered $100,000 in prize money.
• Monaco's poker night is part of a trend of startups thinking outside the box to generate buzz.

An AI startup you've probably never heard of just spent $200,000 on a poker tournament, complete with $100,000 in prizes, an array of Silicon Valley tech founders, and Tiffany jewelry. The goal wasn't gambling. It was marketing.

A few weeks ago, Sam Blond, the cofounder and CEO of AI sales startup Monaco, announced an offer that seemed too good to be true: The company was sponsoring "the largest founder poker tournament of all time," with $100,000 in prizes and celebrity guests at "the coolest venue in all of San Francisco." Best of all, there was no entry fee to play.

"Attendees will remember this event for the rest of their lives," Blond promised.

Talk about setting a high bar!

When someone from Monaco's PR team asked if I wanted to play, there was only one correct answer: "I'm all-in."

When I'm not writing about tech for Business Insider, I spend a lot of time on the felt. I've competed in the World Series of Poker Main Event and play in friendly games in Los Angeles at least once a week.

If I could hold my own with the best players in the world in Las Vegas, surely I could compete with a bunch of nerdy startup founders?

$200,000 to cut through the 'noise'

In case you're wondering, Monaco uses AI to automate tedious parts of the sales process, such as researching leads and drafting personalized outreach emails. Backed by Peter Thiel's Founders Fund, it came out of stealth mode less than two months ago.

Monaco shelled out around $200,000 on the event, half of that on prize money and the other $100,000 on the swanky ballroom, buffet, dealers, and drinks.

That is not chump change for a Series A startup. Blond told me he sees it as a smart marketing expense to get on the radar of its key customers, which are other startups. He has also been sending poker sets and handwritten notes to founders to get them to demo Monaco.

"Startup founders are notorious for loving poker," he told me. "It felt like an on brand fun thing to do."

Monaco's poker night is part of a trend of startups thinking outside the box to generate buzz, according to C.C. Gong, a principal at Menlo Ventures who played in the tournament and often hosts her own poker nights.

Last month, Listen Labs, a Sequoia Capital-backed startup that uses AI-powered "autonomous researchers" to conduct qualitative customer interviews, spent $25,000 on a Berghain-themed techno party to attract engineering talent.

"It's getting harder to cut through the noise," Gong said. "The founders who are getting through are the ones who are able to create something unique that sticks in your mind."

Poker has long been a staple of Silicon Valley's social fabric, a game of calculated risk that mirrors the startup grind itself. In the last few years, the obsession has hit a fever pitch with the rise of the "All-In" podcast and a post-pandemic hunger for in-person events.

"You can find multiple poker nights every night of the week in San Francisco," said Gong. "It makes sense that poker is a game that appeals to this audience."

$100,000 on the line

After riding an elevator to the 15th floor, I was handed a poker chip that would be my entry ticket and walked over to a well-stocked bar offering "Pocket Aces" vodka martinis and "Full House" Old Fashioneds. So much for tech founders going dry.

After scarfing down some tacos and sliders, it was time for the cards to be dealt. I wanted to sit at a "soft" table, so when I saw an empty seat next to DoorDash cofounder and high-stakes regular Stanley Teng, I hurried past.

I was happy that my instincts proved correct, as it became apparent I was playing with founders with limited poker experience. I was also getting great cards and, after a few hours, found myself at the last of two tables, next to one founder discussing AI agents and another who had just graduated from the Y Combinator accelerator. He was trying to tell me about how he was in the midst of "pivoting" his startup, but I could barely hear him over the blaring house music.

While I had the biggest stack of chips at my other table, at this one, I found myself short-stacked, which meant other players could bully me around. I missed the lackadaisical play at my first table because here, everyone definitely knew what they were doing.

A player quickly put me all-in. I called with the top pair of kings and doubled up. A few hands later, another player bet, and then I put him all-in with pocket aces. He mucked his cards. I was now building my chip stack, but at the later stages of tournaments, the blinds, or minimum amount you need to put in, keep going up fast, and my stack began to dwindle. A player on my right made a big bet, and I looked down at my hand and was happy to see pocket jacks. I went all-in, and he called, showing ace-five.

I was a 66% favorite, but as the dealer flipped over the cards, he revealed what I did not want to see: Another ace.

I was out of the tournament in 15th place. That is a good outcome out of 108 players, but it was painful finishing just six places away from being "in the money," where I would have pocketed $2,500 for 9th place. (Per Business Insider guidelines, I would have donated the winnings to charity.)

A short time later, I watched as Kris Rudeegraap, co-CEO of Sendoso, a corporate gifting platform, raised his fists in the air after winning $30,000 for first place with the same hand I had been beaten with: ace-five.

Blond affixed a real Tiffany's bracelet to Rudeegraap's wrist while other founders tossed stacks of fake hundred-dollar bills across the table at him.

"We don't have fun in San Francisco anymore," one founder could be overheard saying as people began to stream out. "This was the best startup launch ever."

Blond declared the event an instant success and says he plans to do more poker nights.

"There was a lot of demand generated from people who saw the posts about the event, were interested in attending, started understanding what Monaco does, and then were interested in partnering with us as a customer," he said. "I also hope people really enjoyed themselves. That was the point."