TJ Laessig is a former corporate grinder turned entrepreneur, with a long history of winning at gambling games from poker, to fantasy sports, to business. Cupe is TJ’s best friend and partner in crime for the past 15 years, along for the ride every step of the way.
Tune in to this podcast series for risk / reward strategies, untold stories, and hot takes on all things sports, gambling, and entrepreneurship.
Follow along as TJ & Cupe navigate their way through the highest stakes game you can play – the game of life.
Rory wins the Masters & Completes the Golf Grand Slam
Sunday was one of the most epic Master's finishes of all time, with Rory McIlroy defeating Justin Rose in a playoff. TJ and Cupe break down this historic win, share their viewing experiences, and discuss the state of professional golf as a whole.
Watch the Show on YouTube: https://www.youtube.com/@tjlaessig
Follow TJ on X: https://x.com/tjlaessig
Follow TJ on Instagram: https://instragram.com/tj_laessig
26 Mar 2025
Severance, Survivor & TV Show Landscape in 2025
TJ and Cupe talk about the landscape of TV in the year 2025, whether or not Severance is the best show ever, and why Survivor is TJ's all time favorite.
Watch the Show on YouTube: https://www.youtube.com/@tjlaessig
Follow TJ on X: https://x.com/tjlaessig (https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqa2xwdWpEYTg1clV3Sy1IdDhXVngwZnBjS2E5QXxBQ3Jtc0tuQld1UTZJa0E4S0ltYmFSS0dOVkxfVGtJbkpNcEdfMkxmWWRxTFljTFdwMllMeHRqLXJpSWowRlY1azk5OUlmYXFSbTFOVXFTUTBoTkw1RVlReE5EdnVyN0U3RzR4SU1pVk1JYnNQNlUtcGlYcnZfZw&q=https%3A%2F%2Fx.com%2Ftjlaessig&v=p5lkfDM4p6I)
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18 Mar 2025
Win Your March Madness Bracket Using Game Theory
March has arrived, which means one thing - college basketball will be taking over our TVs! On this episode, TJ and Cupe discuss how you can use the principles of Game Theory to win your March Madness bracket.
Watch the Show on YouTube: https://www.youtube.com/@tjlaessig
Follow TJ on X: https://x.com/tjlaessig (https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqa2xwdWpEYTg1clV3Sy1IdDhXVngwZnBjS2E5QXxBQ3Jtc0tuQld1UTZJa0E4S0ltYmFSS0dOVkxfVGtJbkpNcEdfMkxmWWRxTFljTFdwMllMeHRqLXJpSWowRlY1azk5OUlmYXFSbTFOVXFTUTBoTkw1RVlReE5EdnVyN0U3RzR4SU1pVk1JYnNQNlUtcGlYcnZfZw&q=https%3A%2F%2Fx.com%2Ftjlaessig&v=p5lkfDM4p6I)
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12 Mar 2025
Golf is the Greatest Leisure Sport on the Planet
Cupe and TJ talk all things golf including their reasoning for why golf is one of the best sports in the world. They cover their golf history and why golf has EXPLODED in popularity over the last 10 years. Hint: Netflix and YouTube have a lot to do with it.
Watch the Show on YouTube: https://www.youtube.com/@tjlaessig
Follow TJ on X: https://x.com/tjlaessig (https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqa2xwdWpEYTg1clV3Sy1IdDhXVngwZnBjS2E5QXxBQ3Jtc0tuQld1UTZJa0E4S0ltYmFSS0dOVkxfVGtJbkpNcEdfMkxmWWRxTFljTFdwMllMeHRqLXJpSWowRlY1azk5OUlmYXFSbTFOVXFTUTBoTkw1RVlReE5EdnVyN0U3RzR4SU1pVk1JYnNQNlUtcGlYcnZfZw&q=https%3A%2F%2Fx.com%2Ftjlaessig&v=p5lkfDM4p6I)
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5 Mar 2025
Poker for Dummies & Learning to Play GTO
Poker is the OG skill gambling game. On this episode, TJ and Cupe talk through their journeys in the game of poker, the evolution of poker study over the years, and the poker retreat TJ attended last November.
Watch the Show on YouTube: https://www.youtube.com/@tjlaessig
Follow TJ on X: https://x.com/tjlaessig (https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqa2xwdWpEYTg1clV3Sy1IdDhXVngwZnBjS2E5QXxBQ3Jtc0tuQld1UTZJa0E4S0ltYmFSS0dOVkxfVGtJbkpNcEdfMkxmWWRxTFljTFdwMllMeHRqLXJpSWowRlY1azk5OUlmYXFSbTFOVXFTUTBoTkw1RVlReE5EdnVyN0U3RzR4SU1pVk1JYnNQNlUtcGlYcnZfZw&q=https%3A%2F%2Fx.com%2Ftjlaessig&v=p5lkfDM4p6I)
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26 Feb 2025
USA vs Canada Recap & the Great Game of Hockey
For a brief moment last week, hockey took the sports world by storm with the 4 Nations tournament, culminating in the USA vs Canada championship game. On this episode of Gamble, TJ and Cupe break down their past experiences with hockey, discuss the success of the 4 Nations tournament, and talk about the future of hockey, its potential to increase in popularity, and why they believe it is the best team sport in the world.
Watch the Show on YouTube: https://www.youtube.com/@tjlaessig
Follow TJ on X: https://x.com/tjlaessig
Follow TJ on Instagram: https://www.instagram.com/tj_laessig
18 Feb 2025
Make +EV Decisions & Think Like a SHARP Gambler
TJ and Cupe break down one of the key terms in the gambling space - Expected Value. TJ explains the concept of EV, shares examples of EV across games like poker, fantasy sports, and NBA Top Shot - and even discusses how you can apply this decision-making framework in your everyday life.
Watch the Show on YouTube: https://www.youtube.com/@tjlaessig
Follow TJ on X: https://x.com/tjlaessig
Follow TJ on Instagram: https://www.instagram.com/tj_laessig
Follow Cupe on X: https://x.com/therealcupe
Follow Cupe on Instagram: https://www.instagram.com/golf_cupe
13 Feb 2025
$10,000 Wins & the Early Days of Daily Fantasy Sports (DFS)
TJ and Cupe travel back in time to 2012-2017, the early days of Daily Fantasy Sports (DFS). They reflect on the landscape of the games at that point in time, share stories of their first $10,000 wins, and discuss the value of being early to new game types, and how you can identify these types of opportunities for yourself.
Watch the Show on YouTube: https://www.youtube.com/@tjlaessig
Follow TJ on X: https://x.com/tjlaessig
Follow TJ on Instagram: https://www.instagram.com/tj_laessig
Follow Cupe on X: https://x.com/therealcupe
Follow Cupe on Instagram: https://www.instagram.com/golf_cupe
5 Feb 2025
Poker, Fantasy Sports & Intro to Gamble: The Game of Life
TJ and Cupe premier the first episode of a new podcast, Gamble : The High Stakes Game of Life.
The show will cover TJ's life journey and a decades worth of highs and lows in poker, fantasy sports, entrepreneurship, and more with color commentary from side-kick Cupe.
On Episode 1, they provide an introduction to the podcast series as a whole, dive into their individual backgrounds, and specifically talk through their origin stories in poker, fantasy sports, and business.
Watch the Show on YouTube: https://www.youtube.com/@tjlaessig
Follow TJ on X: https://x.com/tjlaessig
Follow TJ on Instagram: https://www.instagram.com/tj_laessig
Follow Cupe on X: https://x.com/therealcupe
Follow Cupe on Instagram: https://www.instagram.com/golf_cupe
31 Jan 2025
Introducing Gamble: The High Stakes Game of Life
TJ Laessig is a former corporate grinder turned entrepreneur, with a long history of winning at gambling games from poker, to fantasy sports, to business. Cupe is TJ’s best friend and partner in crime for the past 15 years, along for the ride every step of the way.
Tune in to this new podcast series for risk / reward strategies, untold stories, and hot takes on all things sports, gambling, and entrepreneurship.
Follow along as TJ & Cupe navigate their way through the highest stakes game you can play – the game of life.
Reach and audience
Public platform figures. Ratings count people who left a rating, not total listeners.
YouTube views
672
Score snapshot 15 Sept 2025
Apple Podcasts (US)
5.0 / 5
1 ratings
Podcast Authority Score: 17 / 100
A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.
Quality
9
Social presence
0
YouTube
66
Engagement
0
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Guest appearances
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