Exit Paradox

Amy Castoro, a wealth communication expert with the Williams Group, dives deep into the crucial conversations families must have about money. She highlights why 70% of families struggle with wealth transition and emphasizes the importance of trust and open dialogue. Amy shares insights on teaching children about finances early, fostering values alongside wealth, and crafting a family mission statement. Her practical tools and thought-provoking views challenge listeners to rethink their own relationships with money for a healthier family dynamic.

My friend Jay Radia doesn’t just build businesses—he builds momentum.He’s a three-time tech founder and a prolific angel investor.Since his last exit two years ago, he’s been building Blissgrowth—a venture studio that partners exclusively with exited founders.Why did he choose this path? What has he learnt so far? Was it the right move?For a while, Jay also co-hosted The Joyful Entrepreneur Podcast—a top 10 show about success and happiness.Today, we explore how Jay is designing his venture studio not just for financial success—but for joy, purpose, and meaning.And what he’s learned from both his own journey and the many post-exit founders he works with._____________________________________________________00:00:00 - Introduction 00:04:23 - Emotional journey post-exit00:06:00 - Experiencing emptiness despite success00:07:15 - Defining the Post-Exit journey (Pause, Reset, New Chapter)00:08:15 - Avoiding the corporate trap post-sale00:09:35 - Discovering he's not a CEO type00:10:15 - Founding Blissgrowth and love for early-stage building00:11:30 - Venture Studio vs Angel Investing and Accelerators00:13:15 - Pros and cons of running a Venture Studio00:15:15 - Team dynamics and focus of Blissgrowth00:16:45 - Common misconceptions about Venture Studios00:17:45 - How his studio compares to others00:19:15 - Angel investing vs Venture Studio involvement00:21:15 - Journey from emptiness to fulfillment00:23:15 - Connecting with intuition through stillness and yoga00:25:15 - Daily practices to cultivate inner clarity00:26:60 - The power of quiet and introspection00:28:15 - Rewiring mindset and deep inner work00:30:00 - Changing his relationship with fear00:31:30 - From fear to freedom and growth00:33:00 - The psychology of purpose and contribution00:34:15 - Observations on other exited founders and finding purpose00:35:45 - Why decoding purpose is a unique journey00:37:15 - Role of spirituality and Indian heritage in self-discovery00:39:45 - Spirituality as a path to love and connection00:41:15 - Overcoming skepticism and redefining success00:43:15 - AI, intellect, and spiritual work00:44:15 - Creating and renaming his podcast: Joyful Entrepreneur00:46:15 - Why he paused podcasting despite success00:47:45 - Lessons learned from podcasting00:49:15 - The power of public self-expression for exited founders00:50:45 - Normalizing post-exit struggles in the founder community00:52:15 - Redefining success after financial freedom00:53:45 - Jay’s 5-pillar framework for purpose00:55:45 - How Blissgrowth aligns with his purpose00:57:15 - Building to scale vs building to exit01:00:15 - Should founders build with an exit in mind?01:01:45 - Jay’s commitment to Blissgrowth long-term

Linda Abraham, founder of comScore and current head of Crimson Capital, shares her remarkable journey as a top entrepreneur and devoted mother of four. She reflects on her first business exit, achieving a massive 5X return in just two years. Linda discusses the emotional landscape of business transitions, surviving the dot-com crash, and the evolution of her companies. She emphasizes balancing motherhood with professional success, nurturing values in her children, and her shift towards holistic health and investment strategies.

Adam Rossi, who sold his company Platinum Solutions and found life-changing wealth, shares his journey of coping with regret and redefining purpose post-exit. He discusses the challenges of transitioning from entrepreneurship to investing, emphasizing the importance of mindfulness. Adam's insights on balancing family life with business are particularly compelling, revealing how building the business with his wife, Leila, strengthened their marriage. He reflects on the allure of philanthropy and the struggle for meaningful impact versus financial gains.

Mike Brown, a post-exit entrepreneur and dedicated coach, shares his tumultuous journey after selling his business. He discusses the emotional chaos following the exit, including the impact on his marriage and his struggles with identity. The conversation dives into the importance of finding purpose beyond achievement, navigating personal growth, and the dangers of early retirement. Mike also reflects on parenting and the nuances of defining wealth beyond mere dollars, emphasizing the value of meaningful relationships and self-discovery.

Cass and Mike Lazerow, entrepreneurs and authors of "Shoveling Shit, a Love Story", share their journey of building two companies together and achieving an $800M exit. They discuss the unique challenges and emotional toll of entrepreneurship, particularly as a married couple with children. The couple delves into the importance of mental health, work-life balance, and the lessons learned from their successes and failures. They also explore how to raise financially savvy kids grounded in self-discovery and purpose.

Josh Payne, founder of Stack Commerce, shares his transformative journey after selling his company for nearly $100 million. He discusses the emotional aftermath, emphasizing how money didn’t solve everything. Family takes precedence now, and he reflects on the identity shifts entrepreneurs face post-exit. By training for an Ironman, Josh highlights lessons in overcoming mental barriers and the importance of finding purpose beyond mere profit. His focus is on creating sustainable businesses while prioritizing well-being and family values.

In this conversation with Alex Macdonald, Founder of the $300M digital concierge company Velocity Black, he reveals his post-exit mindset. Rather than retiring, he dove into building SQL to avoid the existential crises many face after selling a business. Alex discusses the emotional toll of transitioning from entrepreneur to investor, the importance of community over individualism, and the significance of maintaining connections. He challenges conventional happiness, emphasizing that true fulfillment often springs from embracing struggle and cultivating kindness in leadership.

Cory Janssen, co-founder of Investopedia, shares his journey 17 years post-exit. After selling his company, he faced a turbulent period of trial and error in finding purpose beyond profit. His transition to impactful AI solutions reenergized him, shifting his focus from personal gain to community contribution. Cory discusses the emotional and financial complexities post-sale, insights on entrepreneurship, and the necessity of aligning personal goals with wider societal impact. His candid reflections offer valuable lessons for anyone navigating life after a significant business exit.

Michael Miller, a Vedic meditation teacher and former business professional, shares his journey from corporate success to spiritual fulfillment. He discusses how meditation can enhance clarity and decision-making, drawing insights from notable figures like Jack Dorsey and Bill Gates. Listeners will discover the science behind meditation, its healing properties post-exit, and the importance of inner peace for personal growth. Michael also emphasizes the balance of introspection and engagement with the world, advocating for meditation as a transformative practice for entrepreneurs.