How Adam Wexler Bootstrapped His Way to a Multi-Billion Dollar Exit

In this episode of Founder2Founder, Aaron Spivak sits down with Adam Wexler, Founder and Executive Chairman of PrizePicks, the largest paid fantasy sports platform in North America. With a career spanning from music tech startups to influencer marketing software and now dominating the fantasy sports industry, Adam is a prime example of what it means to build with vision, grit, and resilience. Beyond PrizePicks, Adam has launched multiple ventures, served as a pioneer in fantasy sports innovation, and continues to shape the industry through his not-for-profit initiatives and leadership as an active board member.

Adam opens up about his early years experimenting with product-market fit, including his first startup GoRankem, the transition into B2B SaaS with Insightpool, and the eventual creation of PrizePicks after enduring setbacks that would have stopped most founders in their tracks. He shares battle-tested lessons on resourcefulness, hiring with culture in mind, building when no one is watching, and maintaining momentum through uncertainty. This is a masterclass in entrepreneurial durability, from scrappy beginnings to strategic exits, told with honesty, clarity, and tactical wisdom.

Chapters:
 02:20 – Discovering the Startup Bug During Birthright Trip
 06:23 – Finding His First Technical Co-Founder
 08:13 – Building GoRankem and the Power of Crowdsourced Music Discovery
 11:57 – The Harsh Reality of Monetizing B2C
 14:39 – Using Kickstarter Before Crowdfunding Was a Word
 18:58 – Becoming the First Tech Startup to Raise on Kickstarter
 22:04 – Resourcefulness and the Art of Bootstrapping
 25:00 – Lessons From Chapter One: Necessity Breeds Hustle
 28:27 – The Canoe Test and Hiring With Intention
 31:41 – Culture as a Defensible Advantage
 34:33 – The Birth of Insightpool and Enterprise B2B SaaS
 39:45 – Spinning Up Multiple Ventures at Once
 44:09 – Identifying Influencers and Building the Next Chapter
 47:36 – Scaling Insightpool Through Enterprise Clients
 51:10 – Transitioning From CEO to Chief Strategy Officer
 55:12 – How Letting Go of Ego Opens Bigger Doors
 59:24 – The Origin of PrizePicks and Pursuing B2C Upside
 1:03:42 – The Collapse of Fantasy Sports in 2015
 1:16:25 – Founding PrizePicks Amid Regulatory Turmoil
 1:20:45 – Navigating COVID and Keeping the Business Alive
 1:29:41 – The Barbados Offsite and the ClearCo Connection
 1:36:04 – Reflecting on Legacy and Impact Post-Exit
 1:39:43 – What’s Next: Not-for-Profit, Special Projects, and Brand Stewardship
 1:43:34 – Advice to His Younger Self: Let Adversity Mold You

Guest Links:
Website: https://www.prizepicks.com/
https://thehiddenjams.org/
Instagram: @thewordpainter
LinkedIn: Adam Wexler

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