Exit Paradox

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.

My guest today is Adam Rossi. He sold his company, Platinum Solutions, 14 years ago and walked away with life changing wealth. But what hit him first after his exit was regret. We talk about how he came to terms with his new reality, searched for his new purpose, and dealt with losing his found identity. My favorite part of Adam's story is that he built his company with his wife, Leila, and their marriage didn't just survive. Building and selling the business, it actually got stronger through it. We talk about what Adam would do differently now that he's had 14 years to reflect. Adam's story is fascinating and full of hard won wisdom. I'm so grateful he shared it.00:00:00 – Introduction & Adam’s Exit Story00:01:06 – Why Exited Founders Make Bad Investors00:05:15 – From Angel Investing to Private Equity00:09:00 – Why Most Second Companies Fail00:10:15 – Lessons from a Failed Acquisition00:12:07 – Buying vs. Building a Business00:14:34 – Regret After Exit and Finding New Purpose00:17:27 – Sacrifice, Purpose & The Next Big Thing00:20:18 – Impact, Meaning & Philanthropy Struggles00:23:44 – Coaching Entrepreneurs as a Calling00:25:18 – Why He Hasn’t Jumped into a Big Mission Yet00:27:00 – Kids, Family, and Timing the Next Move00:29:00 – Angel Investing: Rise and Decline00:31:06 – The Illusion of Control in Angel Investing00:32:35 – Advice for New Angel Investors00:34:45 – Lifestyle Balance Post-Exit00:36:00 – The Grind Years: 20-Hour Days and Stress00:38:00 – Building a Business with His Wife00:41:30 – Division of Labor and Complementary Skills00:43:00 – Conflict Resolution in a Husband-Wife Team00:44:45 – Why They Didn't Start a Second Business Together00:46:15 – Raising Entrepreneurial Kids with Wealth00:50:45 – The Only Real Passive Investing Strategy00:53:26 – Life Rules: Wealth vs. Freedom00:56:40 – Is Balance Between Mission and Freedom Possible?00:58:45 – Mental Health After the Exit01:01:00 – Why He Shares His Story Publicly01:03:15 – A Book for His Kids and Maybe the World01:07:17 – Will He Publish It?01:09:41 – How Adam Wants to Be Remembered01:10:36 – Closing Thanks & Final Reflections

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.

My guest today is Cory Janssen, co-founder of Investopedia. Cory sold the business 17 years ago, but what came next was far from the smooth ride he or anyone might have expected. He spent years in painful trial and error, half-heartedly starting new ventures while avoiding real work, experimenting with professional investing and retirement. None of it satisfied his deeper need for the sense of purpose he felt while building Investopedia. Everything changed when Cory went back to building and working. But this time it felt different. His focus shifted toward unselfish, larger impact goals. His new non-monetary motivation gave him powerful drive and a clear sense of direction and alignment. Today, Cory finally feels deeply fulfilled, energised and joyful. There is so much to learn from Cory's story and we are so lucky he agreed to share it openly. It's rare, raw and packed with specific practical insights for anyone navigating the complexities of post-exit life. _____________________________________________________ TIME STAMPS: 00:00:00 Introduction 00:01:40 Guest Introduction: Cory Janssen’s Story 00:04:00 Founding Investopedia: The Early Days 00:10:55 Deciding to Sell Investopedia 00:22:15 Regret After Selling: Financial and Emotional Impact 00:35:10 Working for the Acquirer: Lessons Learned 00:46:50 Negotiating the Sale Process: Tips for Founders 00:56:20 Post-Exit Struggles: Managing Wealth and Purpose 01:07:10 Challenges of Professional Investing 01:15:30 Rediscovering Passion for Building: Transitioning to AI 01:26:15 Balancing Parenthood and Entrepreneurship 01:37:30 Raising Kids with Wealth: Avoiding Entitlement 01:40:00 Closing Reflections and Key Takeaways

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.

In this engaging discussion, Sarah Douglass, founder of Wise Owl Outfitters, shares her journey of intentional living after selling her successful e-commerce business. She opens up about the emotional void that followed her financial success and her struggle to resist the urge to find immediate productivity. Sarah emphasizes the importance of rediscovering her identity beyond entrepreneurship and explores the delicate balance of motherhood and ambition. Her insights on personal growth and the search for authentic fulfillment are both inspiring and relatable.