What does a former tech entrepreneur, AI solutions expert, mountaineer, and philanthropist do with a little extra time on their hands after retirement?
If you’re Victoria Livschitz, you fall in love with poker, enlist a few of the game’s wizards as mentors, and quickly ascend to the highest stakes while co-founding one of poker’s most innovative AI training platforms, Octopi Poker.
Basically, Livschitz has declared, ‘To hell with retirement.’ She feels it was one of the best decisions of her life. Play poker with the best in the world, see how high and far she can go, and let the chips fall where they may, literally.
“Part of my devotion to poker is an obsession,” shared Livschitz. “It's still new enough for me to be in love with poker. But it's also now a much more calculated investment of time and effort to hopefully be one of the best in the game.”
Watch the full interview above, or listen via Apple and Spotify.
Love of chess ignites business opportunity
Livschitz loved competitive chess when she was very young, though it never became a professional pursuit. Yet chess did evolve into one of her first business ventures while studying mathematics and computer science in university.
“In the early days of the internet, an online chess academy was my first foray into internet businesses. After that, I worked for several companies and was part of the original research team that built and commercialized the very first cloud.”
Cloud entrepreneur
Livschitz had a strong inkling that cloud technology was the next big thing in the computing world and formed a company called Grid Dynamics in 2006. It was the first practical tech company dedicated to building clouds. The company would grow to be a major player in the industry and go public in 2020.
After leading Grid Dynamics through the aftermath of COVID, Livshitz retired, moved to Montana, and pursued another one of her life’s passions – long-distance backpacking and mountaineering.
“I left the corporate environment, I believed hopefully for good. Montana seemed like a perfect place to leave civilization and competitiveness behind me. Tell God your plans and listen to him laugh at you. Because somehow my guilty pleasure became watching final tables of big poker events.”
Livschitz was so enthralled with the game that she hopped on a plane for a ten-day trip to Las Vegas during the 2021 WSOP to see what the crazy game was all about.
Since that fateful adventure, Livschitz has quietly accumulated more than $2,200,000 in career cashes while capturing titles at the 2022 Aria $10K high roller and the 2023 EPT Deep Stack event.
Octopi Poker’s origins
However, Livschitz was dragged back into the corporate world of AI and computer science, this time happily under her own volition, following Andrew Lichtenberger’s 2022 $50K WPT SHR Poker Showdown win.
“Andrew had just won the $50K. Morale was super high amongst everyone. In the aftermath, the pros told me I needed to use solvers and other clunky poker tools to improve my game. I was like, ‘My God, what is this?’ This is not designed for humans. The barrier is insane. I don't want to use it.”
Thus popped the kernel of an idea between Livschitz, Schulman, Lichtenberger, and Phil Shing to create an easy-to-use AI interface that would allow all levels of players to once again have fun studying poker and improving their game. Octopi Poker was born.
PokerOrg’s Craig Tapscott caught up with Livschitz soon after she assumed the CEO role of Octopi Poker. They talked about:
- Beginner’s luck at first WSOP outing, cashing for $30K
- Meeting future mentors Sam Grafton, Nick Schulman, and Andrew Lichtenberger
- The origins of George and Tom, Octopi’s artificial intelligence engines
- Testing the waters of high-stakes cash games in Vegas and LA
- The origins and metaphors behind the name Octopi poker
- #1 mission to bring back the pure joy of studying and playing poker
- Understanding the mathematics and variance in poker as compared to the beautiful game of chess
Listen NOW! You can listen to the full interview on PokerOrg’s Apple and Spotify podcasts.
(NOTE: As this article went to press, Livschitz finished third in the 2025 PokerGo Tour’s Last Chance Event 1 for $127,650.)
