Exit Paradox

Anastasia Koroleva
  • 5.0 (4)
  • ENTREPRENEURSHIP
  • UPDATED WEEKLY
Exit Paradox

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, and build fulfilling lives and families. My mission? To inspire exited founders to wield their unique blend of experience, time, wealth, and community power for a profound global impact. 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 🙏.

  1. Sarah Douglass. Post-Wealth Search for Happiness

    DEC 3

    Sarah Douglass. Post-Wealth Search for Happiness

    My dear friend Sarah Douglass sold her incredibly successful e-commerce business three years ago, achieving the financial freedom she had always dreamed of. But soon after, she found herself grappling with a new challenge: balancing her newfound success with an ever-deepening desire for contentment and a powerful drive to create impact. In today’s conversation, Sarah shares her journey with disarming authenticity, opening up about her deepest struggles. We explore the unexpected void left by success, the difficulty of resisting the urge to immediately start something new just to feel productive, and her shift from chasing external milestones to embracing intentional living—rediscovering who she is as a whole being, not just as an entrepreneur. _____________________________________________________ TIME STAMPS: 00:00:00: Introduction and greetings 00:01:04: Sarah's business journey beginnings (Music school) 00:01:39: Transition to selling online (Discovery at dinner) 00:02:04: Starting with camping gear (Wise Owl Outfitters) 00:02:56: Challenges and operations (Traveling to China) 00:03:40: Balancing family and business (Moving and kids) 00:04:23: Working with her husband 00:05:21: Husband's role and career shift (Becoming a painter) 00:04:37: Decision to sell the business 00:05:00: Influences and reasons for selling 00:07:01: Financial freedom and exiting strategy 00:08:16: The selling process (Timeline and logistics) 00:09:56: Reflections on the buyer's bankruptcy 00:11:06: Emotional impact of selling 00:12:10: Post-sale challenges and burnout 00:13:23: Realizations and health impact 00:14:40: Personal and existential reflections 00:16:55: Seeking and understanding contentment 00:18:37: Advice on spirituality and life direction 00:19:06: Initial thoughts on spirituality and personal development 00:19:23: Exploring different avenues for growth 00:19:46: Impact of personal coaching and physical health 00:20:36: Reflection on life's purpose post-exit 00:21:32: Evaluating new opportunities and the allure of starting new businesses 00:25:00: Importance of being helpful to others 00:27:18: Finding balance in life and prioritizing oneself 00:27:50: Balancing motherhood and business 00:32:17: Handling wealth and teaching children about money 00:34:42: Shifts in business motivation without the need for money 00:38:17: Importance of having a supportive team 00:39:08: Pursuing new, exciting projects 00:40:02: Balancing current business with new ventures 00:40:26: Benefits of taking extended trips 00:42:04: Discovering oneself through new experiences 00:46:04: Reflections on legacy and impact on others 00:48:02: Interpretation of "Stay hungry, stay foolish" 00:51:03: Struggles of balancing business and family as a woman 00:56:06: Comparison of post-exit life to athletes' career transitions 00:56:38: Feeling lonely during the process 00:56:52: Searching for information online 00:57:15: Conclusion and thank you

    58 min
  2. Tim Schumacher. Sedo’s Exited Founder on Work-Life Balance

    NOV 20

    Tim Schumacher. Sedo’s Exited Founder on Work-Life Balance

    Tim Schumacher is the exited founder and former CEO of Sedo, one of the world's largest domain marketplaces, which he led for over a decade before stepping down 13 years ago. What sets Tim apart is how he mastered the elusive work -life balance while still building his company, something most entrepreneurs only dream of. This balance helped him avoid the emotional rollercoaster that so many of us face after a successful exit. In this episode, Tim shares his thoughts on keeping life supernormal, the bootstrapper mindset, being a scaler versus a zero-to-one founder, and finding new purpose in tackling climate change. _____________________________________________________ TIME STAMPS: 00:00:00 - 00:00:39 Introduction 00:00:39 - 00:02:58 Tim Schumacher's Exit and Reflections 00:02:58 - 00:05:58 Transition to New Ventures 00:05:58 - 00:07:28 The Importance of Rest and Work-Life Balance 00:07:28 - 00:09:51. Personal Interests and Climate Change 00:09:51 - 00:11:55. Evolution of Motivation and Values 00:11:55 - 00:16:38. The Bootstrap Mindset 00:16:38 - 00:18:28. Balancing VC and Bootstrap Approaches 00:18:28 - 00:25:30. Scaling vs. Building from Scratch 00:25:30 - 00:29:37. Financial and Purposeful Integration 00:29:37 - 00:31:12 Managing Identity Change Post-Exit 00:31:12 - 00:37:05 Work-life Balance and European Influence 00:37:05 - 00:36:59. Entrepreneurial Legacy and Family 00:36:59 - 00:42:20. Reflecting on Business Strategies and Learnings 00:42:20 - 00:45:26 Revisiting Entrepreneurial Failures 00:45:26 - 00:47:09. Cultural Exposure and Entrepreneurial Growth 00:47:09 - 00:49:29 Purpose and Motivation Beyond Business

    48 min
  3. Rick Eigenbrod. 'Post-Exit Death is Inevitable'

    NOV 14

    Rick Eigenbrod. 'Post-Exit Death is Inevitable'

    Rick Eigenbrod is a deeply respected thinker in the post-exit world. A clinical psychologist and co-author of the classic Yale paper What’s Next: The Entrepreneur’s Epilogue, he’s spent years guiding founders through life after the exit as an executive coach. In this conversation, we get into why Rick believes a “death of who we used to be” and a subsequent "re-birth" are inevitable post-exit, and how resisting these changes only adds to the struggle. Rick generously shares the tools and exercises he’s found most effective in navigating this transformative process. We also explore the grip of dopamine addiction, the healing power of legitimizing post-success frustration, simple ways to reconnect with our natural curiosity and playfulness, and the bittersweet reality of leaving some people behind as we experience exponential personal growth.

    1h 30m
  4. Roy Rubin. Magento’s Exited Founder: Globetrotting and the Search for Purpose

    OCT 31

    Roy Rubin. Magento’s Exited Founder: Globetrotting and the Search for Purpose

    Roy Rubin the visionary founder of Magento, built the open source e-commerce platform from the ground up, leading it to a remarkable exit to eBay in just four years. He then stayed on at eBay for two years, but felt suffocated by corporate walls. That's when it hit him. He barely knew his family anymore. So he and his wife pulled their kids out of school, packed up. and set off on an open-ended journey around the world. For 14 months, they traveled without a plan, letting each destination choose them and discovered what freedom really meant. When they returned, threw himself into the challenge of cycling and completed an Ironman. He also started an angel investment firm to stay intellectually engaged. He has built a beautiful life, but now 13 years post-exit, he is still looking for a new purpose. Roy is torn between the urge to build something big again and the fear of sacrificing his family and lifestyle. Roy is disarmingly open and witty in this conversation. His ideas on personal growth, leadership and fulfillment are fresh and thought-provoking. _____________________________________________________ TIME STAMPS: 00:00:00: Introduction and greetings 00:01:38: Roy's background and introduction to Magento 00:02:3: The founding and growth of Magento 00:03:36: Why Magento was sold to eBay 00:05:28: Reflections on selling Magento 00:05:53: Period after selling: Working at eBay 00:06:51: Challenges and experiences at eBay 00:10:18: Frustrations and limitations at eBay 00:11:07: Difficulty in leading within eBay 00:13:39: Reflections on regret and learning from the experience 00:15:53: Pain of working at eBay 00:18:04: Changes in the leadership team post-acquisition 00:19:25: Leadership style and inspiration 00:22:07: Transparency and leadership approach 00:25:24: Personal reflections post-exit 00:25:48: Reflecting on leaving Magento in 2013 00:28:03: Deciding to leave eBay after Magento's Imagine conference in 2014 00:29:15: The decision to travel with family for 14 months 00:30:00: The travel route through Central America, South America, Asia, and Europe 00:31:03: The travel experience and its impact on family dynamics 00:36:04: Encouragement to other founders to take time off and travel 00:43:02: Discovering new passions post-travel, specifically Iron Man and cycling 00:45:59: Introduction to Personal Journey 00:46:26: Discovering Passion for Sports 00:46:10: Reinventing Post-eBay Life 00:46:44: Starting the Fund During COVID 00:48:04: Transition to Angel Investing 00:51:27: Managing Wealth Post-Magento Sale 00:54:03: Investment Philosophy and Public Equities 00:56:45: The Non-Financial Rewards of Investing 00:58:17: Search for Purpose Beyond Business 01:01:27: Reflection on Purpose During Magento Years 01:03:33: Balancing Life with Current Ventures 01:06:12: Discussing a life of 24/7 dedication 01:06:47: The search for purpose 01:08:01: Meeting new people 01:10:00: The intense journey with Magento 01:12:56: Coping with the transition post-acquisition 01:16:07: Being a creator versus an operator 01:19:11: Future impact and legacy 01:22:10: The desire for more meaningful work 01:26:21: Closing remarks and goodbyes

    1h 24m
  5. Brock Weatherup. Secrets of Successful Sequels

    OCT 21

    Brock Weatherup. Secrets of Successful Sequels

    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

    1h 8m
  6. Scott Wolfe. After $500M Exit: “My Vision Is Forever Unfinished"

    OCT 14

    Scott Wolfe. After $500M Exit: “My Vision Is Forever Unfinished"

    Three years ago, Scott Wolfe sold his company, Levelset, for half a billion dollars. Excited and relieved at first, he soon found himself deeply frustrated with the reality that his vision for the business would now never be realized. Scott is a natural creative who sees building a business as an artistic endeavor. It was this intrinsic need to create that sustained him through the grueling journey of building his business. Post-exit, he misses being driven by that vision and working alongside his exceptional, organically built team—one he feels can never be re-created. In this conversation, we explore the pros and cons of starting a sequel, the paradox of purpose, being a true “hedgehog,” the need for authenticity, full-time parenting, and raising entrepreneurial children. _____________________________________________________ TIME STAMPS: 00:00:00: Introduction and welcome to Scott 00:01:11: Reflections on selling the company 00:02:22: Feelings post-sale and personal identity 00:05:01: Comparing business to art 00:06:58: Transition from attorney to entrepreneur 00:08:57: Founding and growing Levelset 00:11:15: Key roles and talents in the company 00:13:21: Starting a new business and family considerations 00:19:00: Debating the reasons to start another business 00:21:02: Seeking purpose and fulfillment 00:23:21: The necessity of creativity and purpose 00:24:06: The challenges of balancing personal and professional life 00:25:01: The paradox of purpose 00:26:31: Rebuilding life and purpose post-exit 00:27:56: Adjustments and surprises after exiting a company 00:29:02: Facing mortality and existential reflections post-exit 00:31:36: Managing personal expectations and regrets 00:34:07: Reflecting on unfinished business and the non-finality of accomplishments 00:38:03: The journey and appetite for creative endeavors 00:40:44: Exploring new experiments and hobbies post-exit 00:42:28: Writing and reflecting on vision after business exit 00:43:32: Building and helping companies after the exit 00:45:08: Structuring the company's vision 00:45:48: Financial exit and its impact 00:47:25: Managing newfound wealth 00:54:58: Becoming a cautious investor 00:56:00: The hedgehog concept 00:58:53: The influence of entrepreneurial family upbringing 01:01:42: Wishing entrepreneurial experiences for children 01:05:32: The importance of self-reliance and vision for entrepreneurs 01:06:22: Strategy Development and Investment Philosophy 01:08:07: Changes in Motivation Over Time 01:10:40: Current Motivation and Challenges 01:13:36: Inspiration and Choosing People to Surround Yourself With 01:14:21: Building a Network Organically 01:16:33: The Importance of Purpose and Motivation 01:17:49: Reflections on Authenticity and Meeting New People 01:18:04: Legacy and How to be Remembered

    1h 20m
  7. Johnathan. 'Life Forced a New Purpose on Me'

    OCT 7

    Johnathan. 'Life Forced a New Purpose on Me'

    My friend Jonathan has chosen to remain anonymous in exchange for stepping outside his comfort zone — and that he did! Eight years ago, he began a gradual exit from his incredibly successful, bootstrapped company. This strategic approach had an unexpected benefit: it smoothed his post-exit transition, making it more manageable both emotionally and financially. His search for a new purpose—a lengthy and confusing path for most—became clear and compelling after his family was hit by a mental health issue. In this interview, Jonathan shares raw, unconventional wisdom about the advantages of bootstrapping and exiting in stages, and how painful personal challenges gave him a new purpose and source of fulfillment. _____________________________________________________ TIME STAMPS: 00:00: Introduction 01:00 Transition after selling the company 01:20: Jonathan's unconventional wisdom 02:08: Jonathan's previous careers 03:06: Motivation for starting a new business 03:53: Challenges faced in hierarchical systems 04:44: Importance of money in decisions 05:47: Founding a data business 06:44: Challenges in raising money 08:24: Misconceptions about data 10:03: Advantages of bootstrapping 11:14: Financial challenges and salaries 14:53: Impact of minority exit in 2016 17:02: Reasons for full business exit 18:12: Dividend checks and responsibility 19:04: Working with private equity firms 21:04: Importance of choosing the right partner 22:10: Reflections on Exiting During COVID 23:00: Health Issues and Impact on Business 24:03: Regrets and Decisions on Exiting 25:10: Continuing Involvement Post-Exit 26:14: Merging with a US Company 27:02: Adjusting to Life After Business 28:32: Personal and Family Focus Post-Retirement 30:26: Supporting Academic Research and Mental Health 31:29: Motivation of Wealth Training for Children 35:17: Disinterest in Material Possessions 38:13: Sources of Fulfillment and Life Satisfaction 41:47: Outdoor Activities and Personal Well-being 42:00: Processing Life's Experiences into Wisdom 45:36: Small experiences of delight 46:12: Caring for employees through share options 46:50: Satisfaction from contributing to others' happiness 47:08: Reflection on being remembered 48:04: Conclusion and gratitude

    48 min
  8. Jason Kirby. From Exit to Ease: Letting Go of the Stress

    SEP 4

    Jason Kirby. From Exit to Ease: Letting Go of the Stress

    Jason Kirby. He Sold Liquid Sky software to Walmart six years ago, but became disillusioned when Walmart abruptly scrapped the company's ambitious plans. Seeking a new direction, Jason joined Generation Esports, rapidly scaled it and exited three years ago. This last exit prompted Jason to reassess his priorities, leading him to focus on family, health and meaningful work. This shift inspired him to found Thunder, a tech enabled investment bank and launch the fundraising demystified podcast. In this interview, Jason shares his journey from high stress startups to a life centered on fulfillment and purpose. _____________________________________________________ TIME STAMPS: 00:00:00: Overview of Jason’s Expertise 00:01:27: Starting Liquid Sky 00:01:56: Formation and Operational Beginnings of Liquid Sky 00:02:24: The Vision and Mission of Liquid Sky 00:03:11: Partnership and Expansion Efforts 00:03:37: Business Philosophy and Personal Contribution 00:05:15: Diverse Industry Experience 00:06:50: Curious Nature and Learning Process 00:06:53: Liquid Sky’s Rapid Growth and Sale to Samsung 00:08:05: The Failed Acquisition by Samsung 00:10:17: Crisis and Pivot Strategy 00:11:01: Final Attempts for Acquisition and Survival 00:13:28: New Strategy with Walmart 00:15:39: Outcome and Life Post-Acquisition by Walmart 00:19:42: Excitement about Walmart Gaming 00:20:25: Transition to San Diego and New Opportunity 00:20:50: Introduction to Generation Esports 00:21:48: Investing Energy into Generation Esports 00:24:05: Initial Reflection and Momentum 00:25:42: Navigating the COVID-19 Challenges 00:26:28: Series A Funding and Rising Tensions 00:29:06: Decision to Leave Generation Esports 00:31:00: Self-discovery and New Relationships 00:35:19: Learning from Relationship Dynamics 00:36:00: Considering the Next Move 00:36:10: The Idea of Starting Thunder 00:36:42: The seed for Thunder 00:37:18: What Thunder does 00:39:02: Thunder as a tech-enabled investment bank 00:40:21: Introduction to the podcast "Fundraising Demystified" 00:42:00: Origin of "Fundraising Demystified" 00:44:04: The value of understanding venture capital 00:45:11: Advice for post-exit founders considering new ventures 00:52:01: Importance of risk tolerance 00:52:58: Determining the endgame for new businesses 00:53:41: Plans for Thunder 00:54:14: Decision against starting another big business 00:55:04: Balancing career and family priorities 00:55:48: Balancing Family and Ambitions 00:56:07: Introduction to Entrepreneurship in College 00:56:11: Influence of Successful Entrepreneurs 00:56:35: Reflections on Success and Family Time 00:56:39: Closing Remarks

    57 min
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Ratings & Reviews

5
out of 5
4 Ratings

About

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, and build fulfilling lives and families. My mission? To inspire exited founders to wield their unique blend of experience, time, wealth, and community power for a profound global impact. 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 🙏.

Information

  • Creator
    Anastasia Koroleva
  • Years Active
    2023 - 2024
  • Episodes
    44
  • Copyright
    © Anastasia Koroleva
  • Show Website
    Exit Paradox

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