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To Boldly Go Where No Bettor Has Gone Before

Episode 14 · November 2026 · Matt & Andrew · 31 min

On the eve of the midterms I’m calling a Democratic sweep, which means unwinding the Senate bet from Episode 9. How I read a late break in the polls, why Kansas should scare Republicans, and a side bet on when we’ll know who won.

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12 Selling Harris, Buying Newsom & Will the Dolphins Go 0-17? Off the Cuff! September 2026 · Show notes & transcript · Andrew and I both forgot we were recording, so this one’s off the cuff. A 4-2 Week 1, why the Dolphins could go 0-17, a 30-seat midterm line,...
11 Man vs Machine vs the Miami Dolphins: Our NFL Season Bets September 2026 · Show notes & transcript · NFL only. Three Super Bowl baskets race all season: Andrew’s, mine, and one my AI...
10 NFL Is Back: The Lions Are Underpriced, Should Rubio Scare Democrats & Is AOC’s Surge a Mirage? August 2026 · Listen & show notes · Twelve days to kickoff, and I think the Lions are the most mispriced team in football....
09 We’re Back: World Cup Confessions, Betting the 2026 Midterms & NFL Value Picks August 2026 · Listen & show notes · Back after a long summer. The midterms paradox: 8 of the 10 closest Senate races lean...
08 How to Actually Make Money on Polymarket May 2026 · Listen & show notes · How to actually make money on Polymarket: bet what you know, chase reward markets, use...
07 Masters Meltdown, World Cup Arbitrage, Weather Betting & the Aliens Money Glitch April 2026 · Listen & show notes · Andrew’s Masters portfolio blew up after some drunk trading in Italy. Then World...
06 Polymarket Fees, Democrat Nomination Arbs, Masters Picks, SpaceX Ticker Bet, & Still Undefeated April 2026 · Listen & show notes · Polymarket’s hidden fees and what they cost you, an arbitrage in the Democrat...
05 Still Undefeated: Kalshi Gets Sued, WBC Arbs & Blind Betting a French Mayor March 2026 · Listen & show notes · Five bets resolved, five wins, and Tim cashes the Oscars. Kalshi raises $1B while getting...
04 Name Change, Bot Challenge Results, Texas Primary Edge & Masters Arbitrage March 2025 · Listen & show notes · The show is now World at Odds. I lost the $100 bot challenge to Andrew, then we break...
03 Iran Strikes, Polymarket Insider Trading & the $100 Bot Challenge February 2025 · Listen & show notes · Andrew and I dig into the Iran strike markets: trading breaking news, the latency edge,...
02 Super Bowl Scoring, Betting for Beginners & the Aliens Debate February 2025 · Listen & show notes · I bring in Tim Williams, an architect from Omaha who’s never gambled, for a crash...
01 Greenland, 2028 Election Nominees, Super Bowl Odds & Mark Kelly January 2025 · Listen & show notes · The one that started it all. Andrew and I explain what the show is, then get into...

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