Founder2Founder with Aaron Spivak
Entrepreneurship isn’t just a career—it’s a relentless, all-consuming way of life.
Welcome to Founder2Founder a raw and unfiltered podcast where host Aaron Spivak pulls back the curtain on what it really takes to build something from the ground up. No sugarcoating, no overnight success stories—just deep, honest conversations with some of the most driven, underrated, and game-changing founders of our time. From brutal setbacks to game-changing mindset shifts, Aaron goes beyond the polished success stories to uncover the unglamorous, deeply personal side of building a business.
As a seasoned entrepreneur himself, Aaron goes beneath the surface and gets into the nitty-gritty of what it truly takes to succeed. He’ll dive into the habits, behaviors, and routines that set elite founders apart, the tactics and strategies that are working today, and the mindset shifts required to push through the hardest moments. Through raw personal stories, late-night struggles, and breakthrough moments, guests open up about what it really means to grow, not just as a founder, but as a person.
Each week, Aaron sits down with visionary entrepreneurs from high-growth startup founders to seasoned CEOs, for real, unfiltered conversations about the highs, lows, and everything in between. Whether you're scaling a company, launching your first venture, or just looking for inspiration, this podcast will give you the insights, motivation, and real-world advice you won’t get just anywhere. If you're ready to strip away the illusion and get real about what it means to build, sacrifice, and thrive, this is the podcast for you. Join us every Wednesday!
Founder2Founder with Aaron Spivak
How Adam Wexler Bootstrapped His Way to a Multi-Billion Dollar Exit
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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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