Establish The Run Fantasy Football What It's Like To Win $2 Million In NFL Best Ball with UD Champ Sam Sherman and DK Champ Samuel Shepard (Episode 954)
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Jan 9, 2026 Sam Sherman, an Underdog Best Ball Champion who won $2 million, shares how he drafted his winning team and his strategy during the process. He emphasizes the importance of balance and using rankings while drafting. Samuel Shepard, a DraftKings Best Ball Millionaire winner, discusses his background in fantasy and the tools he utilized for success, including a focus on premium tight ends and correlation plays. Both champions reflect on their emotional journeys and future plans after their massive wins.
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From Business School Side Gig To $2M Win
- Sam Sherman stumbled into fantasy content during business school and parlayed it into two seasons of work at Establish The Run.
- He later left for a traditional job, then won $2 million in Best Ball which reopened the possibility of returning to fantasy content.
Draft In A Way You Can Sustain
- Draft in a way that fits your life: Sam did most of his 90 drafts while exercising to avoid burnout.
- Prioritize enjoyment so you can sustain drafting volume across a season.
Pod Luck Is Part Of The Tournament
- Pod luck is an intrinsic feature of Underdog's format and winning often requires variance along the way.
- Sam argues strong final-week scoring matters more than a flawless regular season.