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
Rebuilding Purpose After a Major Exit and How The Work Doesn’t End When You Succeed
In this episode of Founder2Founder, host Aaron Spivak sits down with serial entrepreneur David Segal, best known for building DAVIDsTEA into a $200M brand and now serving as President of Highbeam. David shares the full arc of his entrepreneurial journey, starting with the humble beginnings of DAVIDsTEA, through the grind of expansion and the thrill of going public, to the surprising emotional lows that followed a major exit. With refreshing honesty, he opens up about his feelings after selling the company, how he found renewed purpose, and the process of reshaping his identity beyond his business.
David and Aaron explore the hidden cost of scaling quickly, the emotional whiplash of sudden wealth, and the importance of defining success beyond financial freedom. The conversation is packed with invaluable takeaways for founders at every stage, from negotiating working capital terms that change your bottom line, to the mindset shifts required when stepping into a new venture. Whether you’re in the trenches or on the other side of a win, David’s story is a powerful reminder that the work never really ends, it just evolves. Don’t forget to subscribe, share with a fellow founder, and leave a review if you enjoyed this episode.
Chapters:
01:10 – Starting DAVIDsTEA: The Idea Nobody Was Doing
04:32 – Early Failures and Lessons in Persistence
07:27 – From 4 Stores to 30: What Changed?
08:45 – Building for Scale: The Highs and Pitfalls
11:55 – Expansion Mistakes in the U.S. Market
14:33 – Handing Over the CEO Role: Ego and Learning
16:02 – The Power of Process (Without Bureaucracy)
20:23 – Leaving DAVIDsTEA and Losing Identity
22:15 – From Rock Bottom to Highbeam: A New Beginning
25:50 – Life-Changing Money Doesn’t Mean Life-Changing Fulfillment
28:15 – What Founders Need to Know About Life After the Exit
31:00 – Starting Mad Radish and Firebelly: Lessons in Patience
34:50 – David Now vs. Then: Maturity in Decision Making
38:52 – Sleep On It: Slowing Down to Make Better Decisions
40:09 – Working Capital Masterclass: The Deal That Can Save Millions
44:03 – Lifestyle Business or Unicorn? How to Decide
46:41 – Operating for Cash Flow vs. Chasing the Exit
48:57 – The Power of Compounding and Long-Term Operating
50:33 – Managing Post-Exit Wealth: Keep It Simple
54:56 – David on Legacy and Still Being “Just Getting Started”
58:20 – The Power of Environment and a Supportive Partner
1:01:25 – Entrepreneurship is a Personal Journey
1:03:39 – Advice to 19-Year-Old David: Put in the Work, Keep Showing Up
1:06:19 – Meditation, a “Digital Sabbath”, and Mental Resilience as a Founder
1:11:07 – Final Reflections: Inputs Over Outcomes
Guest Links:
Website: https://www.highbeam.co/
LinkedIn: David Segal
Instagram: @tea_maverick
X: @tea_maverick
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