David Arnett’s career proves that the best job description is the one you write yourself. A Wharton grad who taught tennis and chess before digitizing the world’s first TV ad archive he spent 16 years inventing his own roles in market research and product management. His chess champion mindset became his secret weapon for breaking down startup problems. In early 2020 a weekly virtual poker game sparked his next pivot: Chuck, a sport fan community & engagement app built to let friends talk sports one-on-one instead of shouting into the stadium. David’s story offers practical takeaways on embracing uncertainty leaning into your unique talents and making the leap from corporate ladder to founder life.
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David Arnett: Chess Champ to Founder
Jul 03, 2025

Founder@50
After 30 years of building startups, teams, and products, entrepreneur and media exec Jeremy Toeman is taking time to reflect — and to ask the questions that don’t get answered in pitch decks or exit press releases.
Founder@50 is a podcast for anyone rethinking life, work, or identity. Guests include 20-somethings just starting out to 50-somethings starting over or reflecting back.
Through candid conversations with founders, creators, and builders from all walks of life, Jeremy draws on decades of experience. His career spans places like WarnerMedia, Etsy, and CBS, and this podcast is here to uncover the lessons, mistakes, and moments of reinvention that shape how we build meaningful lives.
Because after years in the game, what really matters is clarity, growth, and doing work that actually lasts.
Still building. Still questioning. Always learning.
After 30 years of building startups, teams, and products, entrepreneur and media exec Jeremy Toeman is taking time to reflect — and to ask the questions that don’t get answered in pitch decks or exit press releases.
Founder@50 is a podcast for anyone rethinking life, work, or identity. Guests include 20-somethings just starting out to 50-somethings starting over or reflecting back.
Through candid conversations with founders, creators, and builders from all walks of life, Jeremy draws on decades of experience. His career spans places like WarnerMedia, Etsy, and CBS, and this podcast is here to uncover the lessons, mistakes, and moments of reinvention that shape how we build meaningful lives.
Because after years in the game, what really matters is clarity, growth, and doing work that actually lasts.
Still building. Still questioning. Always learning.Listen on
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