E245: From $0 to Billions in a Regulated Market
How I Invest with David Weisburd
How I Invest with David Weisburd is a podcast that interviews the world's leading institutional investors. Previous guests include The Ford Foundation, Northwestern University Endowment, CalPERS, Stepstone, and other top limited partners.
David Weisburd
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E245: From $0 to Billions in a Regulated Market

E245 • Nov 18, 2025 • 52 mins

How do you build a multibillion-dollar company from scratch, walk away at the peak, and reinvent your life around purpose, generosity, and impact? In this episode, I talk with Pete Kadens, one of America’s most respected first-generation wealth creators and one of the leading philanthropists focused on closing education and opportunity gaps across the U.S. Today. Pete and I dive into how he built Green Thumb Industries (GTI) into a multibillion-dollar cannabis company, the unsexy strategies that made it work, and why choosing overlooked markets and consumers unlocked massive profit. We cover the power of ownership cultures, transparency, discipline frameworks, and why giving equity and education to employees creates extraordinary performance. We also explore the character transformation that led him to retire at 40.

Highlights:

  • The unsexy strategy behind scaling GTI into a multibillion-dollar operator
  • Why Pete targeted the 30–50-year-old female consumer long before the market noticed
  • How choosing Toledo instead of Chicago and Erie instead of Philadelphia created monopolistic advantages
  • The power of ownership cultures, ESOP-style alignment, and financial transparency
  • Why employees perform better when they are treated like owners
  • Pete’s shift from business success to a life of impact and philanthropy
  • The emotional toll, guilt, and clarity that led him to retire at 40
  • How he rebuilt his parenting philosophy: presence, character, and modeling discipline
  • Why “how you do anything is how you do everything” became his family standard
  • The timeless rule he lives by: the gap between “I should” and “I did”

Guest Bio:

Pete Kadens is a serial entrepreneur and dedicated philanthropist who currently serves as Chairman of The Kadens Family Foundation, a national charitable organization focused on closing education and wealth gaps. He is also the Founder and Co-Chairman of Hope Chicago, which is educating tens of thousands of underserved Chicagoans, and a key supporter of Hope Toledo, now serving more than 300 families with tuition-free college and trade-school pathways.

Pete is the Founder & Chairman of Warmer, a new social platform designed to create kind, supportive, and non-toxic peer-to-peer interaction. He also serves as Chairman Emeritus of StreetWise, one of Chicago’s largest homeless assistance organizations, and sits on multiple nonprofit and for-profit boards dedicated to social impact.

Pete is a 2019 Henry Crown Fellow at the Aspen Institute, one of the most selective fellowship programs in the world, recognizing leaders who create ventures solving society’s most challenging problems.

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Stay Connected:

X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Pete Kadens: https://www.linkedin.com/in/petekadens/

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