Exit Paradox

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.

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.

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.

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.

Ten years ago, Brock Weatherup sold his first company, Pet360.com, to PetSmart for $160 million. It took under five years to build. Since then, he’s had two more successful exits, but two years ago, his journey took an unexpected turn when a life-changing medical diagnosis reshaped his entire outlook. In this episode, Brock talks about the secrets behind his consistent success, what keeps him optimistic and gives him a sense of purpose, and how he cultivates relationships in both business and private life. _____________________________________________________ TIME STAMPS: 00:00:00: Introduction 00:01:17: Brock's first company exit experience 00:03:02: Transition challenges after the exit 00:03:31: Acquisition by PetSmart and transition experience 00:06:00: Acquisition of PetCoach 00:07:45: Brock's role and relationship with PetCoach team 00:08:59: Insights on being a startup to grown-up stage founder 00:09:41: Brock's involvement in subsequent businesses 00:11:00: Selling Great Pet Care due to MS diagnosis 00:11:56: Diagnosis impact on priorities and motivations 00:13:09: Adjusting to life with MS 00:14:38: Post-exit reflections and personal journey 00:15:41: Engaging with the business community in new ways 00:16:27: Realignment of life and business perspectives 00:21:47: Reflections on Sharing Knowledge and Purpose 00:22:08: Importance of Meaningful Involvement and Family Time in Purpose 00:22:26: Daily Approach to Living Purposefully 00:24:10: Impact of Diagnosis on Relationships and Support System 00:26:07: Friends' Support During a Difficult Time 00:26:54: Tracing the Evolution from First Business to Present 00:27:03: Story of the First Business Failure 00:30:02: Lessons Learned from Business Failures 00:31:15: The Role of Investors and Ethics 00:35:59: Challenges of Transitioning from Owner to Employee Mentality 00:38:24: Celebrating Failures and Learning from Them 00:40:52: Keeping Perspective in Business Ventures 00:41:14: Adapting and Learning in New Environments 00:42:48: Introduction to the CEO’s vision 00:44:09: Staying humble and continuing to learn 00:51:22: Balancing experience and youthful energy 00:52:06: The importance of continuous learning 00:54:01: Past performance vs future success 00:56:15: Building successful teams 00:59:55: The value of the cap table and smart investment decisions 01:02:22: Financial considerations and risk profiles 01:03:27: Final advice for building a new business after an exit 01:02:50: Being intentional in business and personal life 01:03:11: Setting personal intentions and accountability 01:04:25: Specific goals and realistic expectations 01:06:00: Applying business discipline to personal life 01:07:15: Correlation between personal and professional success 01:08:08: Open communication and its importance 01:09:19: Achieving balance and happiness 01:09:22: How to be remembered

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.

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.

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.

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.

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.