From Craps Tables to Sudoku Grids: A Microsoft Vet's Journey into Puzzle Setting

From Craps Tables to Sudoku Grids: A Microsoft Vet's Journey into Puzzle Setting

From Hey, Good Game by Nate Kadlac, Aaron Kardell, Joseph Rueter

June 10, 2025 · 40 min · Episode 67

About this episode

David Workman shares his journey from Microsoft veteran to elite puzzle setter, discussing his unique approach to puzzle creation and gambling strategies.

Meet David Workman, known in the puzzle world as "HalfBakedLunatic" - a Microsoft veteran who creates Sudoku puzzles so difficult he can't solve them himself. David shares the incredible story of how he invented TiVo's core technology in 1996, only to watch it slip away when his two-page concept paper got buried at Microsoft. He reveals his epic gambling simulation that proved why casinos always win (even with unlimited money, you'd eventually make bets exceeding the world's GDP), and explains the paradox of puzzle creation - building something is the opposite of solving it. With 64 puzzles published and 10 featured on the legendary Cracking the Cryptic YouTube channel, David has earned his place among elite puzzle setters. His masterpiece had viewers watching for 45 minutes before a single digit was placed. Plus: the hilarious tale of licensing Elvis for $1,200 while a cockroach photo nearly cost millions. Check out David Workman's Resources: http://www.halfbakedlunatic.com/ https://www.linkedin.com/in/mediabizdev/ https://www.youtube.com/channel/UCCkyCXQNZY5ZhoSy1dL8b1Q https://logic-masters.de/Raetselportal/Benutzer/eingestellt.php?start=0&name=HalfBakedLunatic Games…

People in this episode

Hosts: Nate Kadlac, Aaron Kardell, Joseph Rueter

Guest: David Workman

Topics covered

  • puzzle setting
  • gambling strategies
  • technology invention
  • Sudoku puzzles
  • storytelling
  • puzzle creation

Keywords

  • David Workman
  • Sudoku
  • puzzle setting
  • gambling
  • Microsoft
  • TiVo
  • Cracking the Cryptic
  • HalfBakedLunatic
  • Kropki puzzles
  • Elvis

Mentioned in this episode

Organizations: Microsoft, TiVo, Cracking the Cryptic

Products: Sudoku, Craps, Pinochle, Kropki puzzles

Places: world

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