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 OutcomesGuest Links:Website: https://www.highbeam.co/LinkedIn: David SegalInstagram: @tea_maverick X: @tea_maverickStay Connected!Aaron Spivak:Instagram @‌SpivakLinkedin The Founders ClubWebsite www.foundersclubofficial.com Instagram @‌TheFoundersClub Founder2Founder:Instagram @‌Founder2FounderPodcastTikTok @‌Founder2FounderPodcastYoutube @‌Founder2Founder.Podcast

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  1:14:43
• A Framework for Founders On How To Check In Before You Check Out

  In this episode of Founder2Founder, host Aaron Spivak sits down with Adam Klasner. Adam Mordechai Klasner is a widely respected personal growth facilitator, committed to empowering individuals and nurturing meaningful relationships. He masterfully integrates diverse modalities and techniques, including Breathwork, NLP (Neuro-Linguistic Programming), Family Constellations, and Imago facilitation, to guide his clients on transformative journeys. Adam's approach centers on a holistic comprehension of his clients' inner worlds and their connections with others. By harmoniously merging these aspects, he skillfully helps clients achieve profound self-awareness, heal past wounds, enhance communication, and foster profound harmony in their relationships. In addition to his professional endeavours, Adam leads a fulfilling personal life. Happily married and the proud parent of ten children, he appreciates the significance of balancing personal and professional pursuits, while infusing joy into both. Adam shares how facing himself 12 years ago began a life-altering shift, leading him to help men reconnect with their authentic selves. The conversation dives into the concept of “checking in”, a practice of emotional awareness, and how that self-awareness can transform how we lead, live, and relate to others. With a blend of vulnerability, spiritual insight, and grounded leadership, Adam offers tools for founders to identify emotional triggers, address inner wounds, and lead from a place of truth rather than fear.If you enjoyed the episode please subscribe and share this podcast with someone you think could benefit from it!Chapters:01:30 Who Is Adam Klasner?02:40 The Internal Crisis That Changed Everything05:03 The Workshop That Triggered a Life Transformation06:35 Why Most Men Say “I’m Good” And What They're Missing08:32 Aaron’s First Workshop Experience in Montreal11:06 How a Check-In Transformed a Meeting13:19 What Is a Check-In? A Tool for Real Vulnerability17:00 Why We Hide Behind Masks in Business and Life20:13 How Childhood Stories Shape Leadership Patterns23:08 Authenticity vs. Connection: The Tension We All Face25:33 Why Every Founder Must Balance Both to Lead26:50 Practical Daily Tools to Access Your Inner World30:06 Triggers Are Clues: How to Work with Emotional Discomfort32:43 Journaling, Breathwork, and Self-Inquiry: Building a Practice36:41 Aaron’s Real-Time Trigger: A Business Partner Conflict49:27 Discovering the Root Need Beneath the Reaction53:04 Why Real Growth Requires Revisiting the Past58:40 Aaron’s “I’m Not That Good” Belief and Where It Began01:04:01 The Power of Acknowledging What Is01:05:59 Where to Start: Journaling and Awareness 01:10:25 Gratitude for the Past: Why Everything Happens for a Reason01:14:12 What Spiritual Practice Taught Adam About Leadership01:19:56 The Moment Adam’s Father Told Him “You Can Do Anything”01:30:08 Message To Younger SelfGuest Links:www.iamanochi.com@findinganochiStay Connected!Aaron Spivak:Instagram @‌SpivakLinkedin The Founders ClubWebsite www.foundersclubofficial.com Instagram @‌TheFoundersClub Founder2Founder:Instagram @‌Founder2FounderPodcastTikTok @‌Founder2FounderPodcastYoutube @‌Founder2Founder.Podcast

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  1:32:32
• The Secret to Scale? It Wasn’t Capital — It Was Community.

  In this episode of Founder2Founder, host Aaron Spivak sits down with Gary Lipovetsky. Gary Lipovetsky is a digital entrepreneur, strategist, and creator with a track record of building and scaling online businesses. As the co-architect of Valeria Inc., he helped transform Valeria’s audience into a thriving global media company. Before that, he founded a top 100 global website with 200 million monthly sessions at its peak, built multiple successful social platforms, and raised $32 million in venture capital for an eCommerce startup within its first year. Now, Gary also mentors hundreds of creators through Creator Method, an academy helping them master monetization, community growth and even personal development through content creation. As the host of RISE podcast, he uncovers the strategies of top entrepreneurs and industry leaders. With 30 years in digital media, he continues to guide brands and creators in building lasting, impactful communities, resulting in the achievement of their business goals. He talks about the early days of hustle,  knocking on doors, cold calling local businesses, and hand-delivering coupon deals before DealFind ever became a household name. Gary opens up about the scaling phase and what he learned from building a company at lightning speed. He shares why launching a personal YouTube channel was never part of the original plan, how he built it to over a million subscribers, and what the platform taught him about branding and storytelling. Now in his next chapter with Free, he reflects on how his priorities have evolved, what he’s building towards, and why success today looks very different than it used to. This episode is a candid look at growth, reinvention, and staying grounded through it all.Be sure to rate the podcast and subscribe or follow on your favorite platform so you never miss a new episode, every Wednesday!Chapters: 01:35 Motivations Behind Success02:12 Early Life and Challenges04:30 Taking Control of One's Future06:01 First Steps into Entrepreneurship14:06 Defining Entrepreneurial Identity16:01 Partnerships and New Ventures22:36 The Impact of Content Creation30:52 The Dynamics of Relationships and Support33:22 The Power of Quick Implementation37:49 The School of Execution: Learning by Doing40:04 Community vs. Audience: The Shift in Content Creation46:03 The Importance of Focus in Content Creation57:54 The Birth of Creator Method: Community and Purpose01:08:55 Empowering Others: The Mission Behind Creator Method01:10:28 The Power of Collaboration Among Creators01:12:30 Shifting Perspectives: From Competition to Community01:13:00 Debunking the Algorithm Myth01:20:00 Redefining Masculinity: Supporting Your Partner's Growth01:30:32 Embracing Mortality: Living with Intention01:39:10 Choosing Gratitude: A Perspective ShiftGuest Links:Valeria Inc https://www.valeriainc.comCreator Method https://creatormethod.comInstagram @GaryLipovetsky https://www.instagram.com/GaryLipovetsky Youtube @Gary.Lipovetsky https://www.youtube.com/@Gary.LipovetskyStay Connected!Aaron Spivak:Instagram @‌SpivakLinkedin The Founders ClubWebsite www.foundersclubofficial.com Instagram @‌TheFoundersClub Founder2Founder:Instagram @‌Founder2FounderPodcastTikTok @‌Founder2FounderPodcastYoutube @‌Founder2Founder.Podcast

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  1:42:25
• From 3D Printer to Multimillion-Dollar Brand: The Playbook for Turning Simple Ideas Into Real Revenue – Without Chasing the Spotlight

  In this episode of Founder2Founder, host Aaron Spivak sits down with Jay Conohan. Jay Conohan is the founder of The Loud Cup Company, a serial entrepreneur, inventor, and proud father of three. With a relentless drive to figure things out, he’s built his career on resilience, hard lessons, and a willingness to bet on himself. From launching the Bath n Play, to juggling multiple ventures while holding a day job, Jay has faced failures head-on and turned them into stepping stones. He believes in fairness, brutal honesty, and proving people wrong when they count him out. With no degree but an unstoppable mindset, he’s built a life around innovation, family, and pushing limits—both in business and beyond. Jay dives into the critical moments that shaped his path, from making tough financial decisions to refining operations and leadership. He breaks down the mindset shifts that helped him scale and the lessons he learned along the way. This conversation is packed with real insights on what it takes to grow a business against the odds. Don’t miss this deep dive into the mindset and strategies behind real entrepreneurial success. Be sure to rate the podcast and subscribe or follow on your favorite platform so you never miss a new episode, every Wednesday!Chapters:03:07 Early Entrepreneurial Experiences and Lessons Learned05:51 The Impact of COVID on Business Ventures08:59 The Birth of the Bath and Play Product11:53 Networking and the Founders Club Experience15:02 The Role of Support Systems in Entrepreneurship17:59 Navigating Success and Self-Discovery21:01 Finding Purpose Beyond Business23:49 The Importance of Relationships in Business27:09 Facing Fears and Embracing Growth29:33 The Innovative Cup: A Unique 3D Printing Experience31:10 Building Connections: The Power of Networking32:43 Kickstarter Journey: From Concept to Launch34:10 Trusting the Process: Lessons in Entrepreneurship38:40 Scaling Up: The Transition from Kickstarter to E-commerce41:13 Achieving Rapid Growth: From Zero to Seven Figures44:43 Navigating Success: Balancing Business and Personal Life54:42 Reflections on Opportunity Cost57:53 Strategic Partnerships and Growth Potential01:01:35 The Power of Networking and Self-Awareness01:03:40 Lessons from Business Setbacks01:10:41 Turning Challenges into Opportunities01:19:11 Finding Purpose After Success01:26:28 Messages to My Younger SelfGuest Links:Loud Cup Company: www.loudcup.com @theloudcupLinkedIn: https://www.linkedin.com/in/conohan/Stay Connected!Aaron Spivak:Instagram @‌SpivakLinkedin The Founders ClubWebsite www.foundersclubofficial.com Instagram @‌TheFoundersClub Founder2Founder:Instagram @‌Founder2FounderPodcastTikTok @‌Founder2FounderPodcastYoutube @‌Founder2Founder.Podcast

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  1:31:51
• How to Go From Nothing to a Multimillion-Dollar Brand Without Outside Funding

  In this episode of Founder2Founder, host Aaron Spivak sits down with Lior Ohayon. Lior is a serial entrepreneur from Toronto, now based in Miami with his family. Finding early success in the internet marketing world, he eventually transitioned into tech and landed on e-commerce. His most recent co-founded business Hush, sold to a publicly traded company for a landmark $48M deal. Now he spends his time helping other startups find their voice and refine their story for a major exit.Lior Ohayon shares how he went from dropping out of school to building Hush into one of North America's top weighted blanket brands. He breaks down the key decisions that shaped his path, from leveraging SEO to fund his early ventures, taking calculated risks, and scaling a product-based business from the ground up.He reflects on the turning points that defined his journey, from struggling with seasonality, to launching a record-breaking Kickstarter and ultimately exiting the company. This conversation gets into the mindset and strategies behind real business growth. Be sure to rate the podcast and follow on your favourite platform, so you never miss a new episode every Wednesday!Chapters:03:07 The Decision to Drop Out of School06:02 First Steps into Entrepreneurship08:55 Transitioning to Software and SEO11:54 The Birth of Hush and Partnership Dynamics14:54 Navigating Challenges and Scaling the Business17:54 The Kickstarter Success Story21:07 Building Trust and Collaboration23:56 Celebrating Small Wins and Validation26:50 Overcoming Seasonal Challenges30:06 The Power of Belief and Support32:59 Lessons Learned from Partnership38:12 The Power of Problem Solving39:46 Goal Setting: A Catalyst for Success42:52 The Importance of Hard Work and Team Dynamics45:15 Learning Through Experience: The Journey of Entrepreneurship48:46 The Role of Preparation in Business Success51:48 Navigating Growth and Change During COVID-1954:34 The Importance of Values in Business01:01:16 Reflections on Personal Growth and Future AspirationsGuest Links: LinkedIn: https://www.linkedin.com/in/lior-ohayonStay Connected!Aaron Spivak:Instagram @‌SpivakLinkedin The Founders ClubWebsite www.foundersclubofficial.com Instagram @‌TheFoundersClub Founder2Founder:Instagram @‌Founder2FounderPodcastTikTok @‌Founder2FounderPodcastYoutube @‌Founder2Founder.Podcast

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  1:11:35

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