Exit Paradox
Anastasia Koroleva
I'm Anastasia Koroleva, a 4x exited founder exploring life after selling a business with some of the most remarkable post-exit entrepreneurs in the world. Together, we rediscover purpose, redefine success, master investing, and build fulfilling lives and families.
Having survived a 9-digit exit, I dedicated a decade to researching the deepest challenges faced by entrepreneurs after a business sale. This podcast is the platform to share my and other exited founders' hard-earned wisdom with the world.
To join our community, please subscribe and share your thoughts. I’d love to hear from you 🙏.
Having survived a 9-digit exit, I dedicated a decade to researching the deepest challenges faced by entrepreneurs after a business sale. This podcast is the platform to share my and other exited founders' hard-earned wisdom with the world.
To join our community, please subscribe and share your thoughts. I’d love to hear from you 🙏.
Episodes
Mentioned books
Feb 28, 2025 • 55min
From $100M Exit to Fulfilment: Josh Payne’s Playbook
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.
Feb 18, 2025 • 1h 35min
Alex Macdonald. A $300M Exit is No Reason to Retire
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.
Jan 7, 2025 • 1h 41min
Cory Janssen. 17 Years Post-Exit: Insights from Investopedia’s Founder
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.
5 snips
Jan 6, 2025 • 1h 48min
Michael Miller. Meditation: the Ultimate Post-Exit Medicine
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.
15 snips
Dec 3, 2024 • 57min
Sarah Douglass. Post-Wealth Search for Happiness
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.
Nov 20, 2024 • 47min
Tim Schumacher. Sedo’s Exited Founder on Work-Life Balance
Tim Schumacher, the exited founder and former CEO of Sedo, shares insights on mastering work-life balance while growing a successful domain marketplace. He reflects on the importance of rest post-exit and his transition into climate-focused ventures. Tim discusses the bootstrapper mindset versus venture capital approaches, emphasizing sustainable growth. He also highlights his shift in motivation, moving from entrepreneurship to tackling pressing climate issues, all while managing personal identity and values shaped by his experiences.
34 snips
Nov 14, 2024 • 1h 30min
Rick Eigenbrod. “Post-Exit Death is Inevitable”
Rick Eigenbrod, a clinical psychologist and co-author of a pivotal Yale paper, dives into the transformative journey after business success. He discusses the 'death of who we used to be' that entrepreneurs face post-exit, emphasizing the need for acceptance in this painful evolution. Rick unveils his effective tools for self-discovery, addressing dopamine addiction and the emotional toll of letting go of former identities. He highlights the bittersweet nature of personal growth, balancing joy, frustration, and the importance of authentic connections.
Oct 31, 2024 • 1h 24min
Roy Rubin. Magento’s Exited Founder: Globetrotting and the Search for Purpose
Roy Rubin, the visionary founder of Magento, shares insights from his incredible journey after selling the e-commerce giant to eBay. Feeling suffocated in corporate life, he embarked on a 14-month globe-trotting adventure with his family to rediscover freedom and connection. He reflects on the challenges of transitioning from startup culture to corporate constraints and the emotional journey post-exit. Now focused on angel investing, he candidly discusses the struggle to find new purpose while balancing ambition and family life.
Oct 22, 2024 • 1h 8min
Brock Weatherup. Secrets of Successful Sequels
Brock Weatherup, an entrepreneur who sold Pet360.com for $160 million, shares his insights on success and resilience. Reflecting on his journey through three successful exits, he discusses the emotional challenges of transitioning from owner to employee after acquisitions. Following a life-changing MS diagnosis, Brock emphasizes the importance of strong relationships and living with purpose. He also highlights the power of mentorship and intentional living, showing how personal and professional aspirations intertwine, especially during tough times.
Oct 15, 2024 • 1h 20min
Scott Wolfe. After $500M Exit: “My Vision Is Forever Unfinished"
Scott Wolfe, founder of Levelset and author of a $500 million exit, shares his post-sale reflections on life, purpose, and creativity. He grapples with the emotional rollercoaster from pride to frustration after selling his business, highlighting the challenges of reclaiming identity. Wolfe compares entrepreneurship to art and discusses the bittersweetness of leaving behind a collaborative team. He also dives into the quest for fulfillment, the impact of entrepreneurial parenting, and the paradox of purpose in a new life chapter.
