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
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.
Oct 8, 2024 • 48min
Johnathan. 'Life Forced a New Purpose on Me'
Jonathan shares his path of transitioning from a successful company to a new purpose, driven by personal challenges within his family. He discusses the advantages of bootstrapping and leaving a business in stages, which made his emotional journey smoother. Through reflections on mental health, he emphasizes the importance of philanthropy and supporting future generations. Their dialogue also touches on financial literacy for youth, the value of relationships over wealth, and the joys of nurturing a startup akin to raising a child.
Sep 6, 2024 • 57min
Jason Kirby. From Exit to Ease: Letting Go of the Stress
Jason Kirby, a tech entrepreneur who scaled Generation Esports and founded Thunder, shares his transformative journey from high-stress startups to a fulfilling life. He reflects on the challenges faced during the sale of Liquid Sky to Walmart and the emotional turmoil that followed. Jason emphasizes the importance of curiosity and adaptability in business, and how those traits helped him pivot towards a meaningful venture. He also discusses balancing family life with professional aspirations, highlighting the need for personal fulfillment over mere business success.
Aug 30, 2024 • 1h 10min
Matthew Johnson. Prolific Exited Entrepreneur on Work-Life Balance
Matthew Johnson is a prolific exited entrepreneur known for transforming the healthcare software sector and leading TruConnect into a telecom powerhouse. In this conversation, he reveals his journey from finance to fulfilling entrepreneurship, emphasizing the importance of work-life balance and family. Matthew shares insights on hiring and management challenges, navigating investment strategies, and raising entrepreneurial children. He also discusses his passion for charity work, illustrating how purpose-driven endeavors provide deeper fulfillment than mere profits.
Aug 20, 2024 • 32min
Bill Flagg. 5 Exits Later: Pursuit of Inspiration
Bill Flagg is a seasoned entrepreneur who built five thriving tech businesses before seeking a simpler life in Portugal. In their conversation, Bill shares his journey from intense entrepreneurship to a place of creativity and inspiration. He discusses the emotional turmoil of his post-exit identity crisis and the challenges of letting go of past achievements. Emphasizing the importance of introspection, he reflects on finding joy in simplicity and the fulfillment that comes from embracing uncertainty and living authentically.
Aug 14, 2024 • 37min
Tony Kula. Post-Exit Shift: From Workaholic to Ironman
Tony Kula, a former entrepreneur who built and exited three businesses by his mid-20s, shares his transformative journey from workaholic to Ironman athlete. He reflects on the importance of prioritizing health and personal fulfillment, especially after the challenges faced during the pandemic. Tony discusses his new ventures in angel investing, emphasizing the significance of supporting aspiring entrepreneurs. He also explores the evolving meaning of purpose and the legacy of kindness one leaves behind.
11 snips
Aug 7, 2024 • 58min
Shane Neman. Secrets of Post-Exit Happiness
Shane Neman, an entrepreneur behind the successful JoonBug and EZ Texting, shares insights from his rollercoaster journey of building and selling businesses. He dives into the emotional complexities of life after a lucrative exit, revealing how to attain happiness and balance. Shane discusses his pivot to real estate investment and personal health strategies, like cold plunging, after grappling with burnout. His reflections on decision-making emphasize the importance of self-identity beyond entrepreneurship, blending wisdom with humor for a truly engaging conversation.
Jul 31, 2024 • 1h 8min
Ben White. 'Dark Decade' After $800M Exit: Addiction. Divorce & Financial Losses
Ben White, a successful entrepreneur who sold his last business for $800M, shares his tumultuous journey through addiction and divorce following his exit. He discusses the emotional void left by stepping away from business and the poor investments made in that time. Despite a dark decade, Ben reveals how he emerged happier than ever by focusing on personal relationships and authenticity. He reflects on the value of genuine friendships and the importance of staying grounded as he returns to entrepreneurship with renewed vision.
Jul 24, 2024 • 47min
Alex Bean. From $2.5B Exit to Fulfillment and Impact.
Alex Bean, founder of the $2.5 billion fintech company Divvi, now runs a VC firm called Tandem and authored 'The Factory for Good.' He dives into the emotional ups and downs after a big exit, sharing feelings of joy mixed with unexpected unfulfillment. Alex emphasizes the importance of finding purpose beyond wealth, nurturing relationships, and impacting future generations. He discusses transforming personal finance to focus on social good and exploring one's unique strengths for fulfillment. His insights aim to inspire a meaningful legacy.
