Exit Paradox

Anastasia Koroleva
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  • ENTREPRENEURSHIP
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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. Alex Macdonald. A $300M Exit is No Reason to Retire

    5 DAYS AGO

    Alex Macdonald. A $300M Exit is No Reason to Retire

    What would you do if you sold your company for 300 million dollars? Retire? Explore the world? Do all these other things you had no time to do while building a business? This is not what my friend Alex Macdonald did when he sold his company Velocity Black two years ago. In fact, Alex made it quite impossible for himself to have any kind of post-exit sabbatical. Why? Well, Alex has seen enough of his post-exit founder friends getting stuck in full-blown existential crisis after they sold their company. He didn't want that to happen to him. I think honestly, if I had had that void, it probably would have not led to a productive use of my energy. I'm actually very happy that I had something immediately to jump into. And yeah, that's led to me not having to go through that challenging period that I see a lot of my friends go through, questioning their identity and everything. In this episode, we're going to explore why he made this decision, whether two years later he still feels it was the right one, and how he applies the lessons from his first full entrepreneurial cycle to building his new business, appropriately called SQL. 🚀 00:00:00 - Introduction 💼 00:02:25 - The Story of Velocity Black 🏦 00:07:46 - Selling Velocity Black to Capital One 🔥 00:07:05 - Why Alex Started Another Business Before Selling His First One 🧠 00:10:52 - The Founder’s Existential Crisis After an Exit 👷‍♂️ 00:12:45 - The Shortage of Builders, Not Investors 💪 00:14:19 - Work-Life Balance & Health After an Exit 📊 00:16:21 - Lessons from Running a 24/7 Business ⚖️ 00:19:52 - Changing Approach to Work with Sequel 🕵️‍♂️ 00:21:19 - Different Approaches to Post-Exit Businesses 🏛️ 00:24:19 - Sequel: Building a Next-Gen Goldman Sachs 🏁 00:27:26 - Managing Motivation After Financial Success 🔑 00:31:03 - Fulfillment vs. Happiness: What Really Matters? 🩺 00:33:15 - The Biohacking & Longevity Obsession 🤝 00:35:51 - Community & Meaning in Life After an Exit 🙏 00:39:13 - The Idea of Creating a New Religion 📜 00:45:46 - The Role of Structure & Responsibility in Life. 🔓 00:54:08 - The Challenge of Freedom After an Exit 📈 00:57:46 - Angel Investing & How It Led to Sequel 🎯 01:03:42 - Helping Athletes Transition Beyond Their Careers 💰 01:07:37 - Building a Legacy vs. Just Making Money ⚠️ 01:10:52 - Avoiding Mistakes in Early-Stage Investing 📢 01:15:30 - The Power of Influence in Investing 🚀 01:20:05 - Sequel’s Future Plans & Scaling the Model 🏆 01:25:00 - What Drives Long-Term Success? 🛑 01:30:10 - Final Thoughts & Advice for Founders

    1h 35m
  2. Cory Janssen. 17 Years Post-Exit: Insights from Investopedia’s Founder

    JAN 11

    Cory Janssen. 17 Years Post-Exit: Insights from Investopedia’s Founder

    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

    1h 41m
  3. Michael Miller. Meditation: the Ultimate Post-Exit Medicine

    JAN 10

    Michael Miller. Meditation: the Ultimate Post-Exit Medicine

    This interview is a special one for me. Michael Miller has been a friend for over 15 years and has made a huge difference in my life. He's a Vedic meditation teacher who taught me to meditate at a time when I was searching for clarity and tranquility following a life-changing exit. Since then, meditation has been my go-to tool for healing, finding peace, processing ideas, and making decisions. And it's not just me, people like Jack Dorsey, Bill Gates, Arianna Huffington, and Ray Dalio all credit meditation for helping them on their own post-exit journeys. Before discovering his calling as a meditation teacher, Michael had a successful business career. That experience gives him a unique ability to explain meditation in ways that make sense to us entrepreneurs. If you've tried meditation before, but let it slip, this might just inspire you to pick it back up. _____________________________________________________ TIME STAMPS: 00:00 The Healing Power of Meditation 02:46 Personal Journeys and Transformations 06:10 The Science Behind Meditation 11:54 Meditation as a Decision-Making Tool 17:49 The Ripple Effect of Meditation 24:06 Creating Peace from Within 40:07 The Ripple Effect of Inner Peace 44:51 The Journey of Personal Growth Post-Success 49:52 Addiction as a Spiritual Search 52:15 From Material Success to Fulfillment 59:33 Designing a Toolbox for Holistic Leadership 01:13:30 The Journey of Self-Discovery 01:18:05 Navigating Life Stages and Transitions 01:23:25 Embracing Discomfort for Growth 01:29:35 The Role of Community and Giving Back 01:34:08 Traveling with Purpose 01:39:23 Understanding Consciousness 01:42:34 Defining Purpose and Connection

    1h 48m
  4. Sarah Douglass. Post-Wealth Search for Happiness

    12/02/2024

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

    11/20/2024

    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
  6. Rick Eigenbrod. 'Post-Exit Death is Inevitable'

    11/14/2024

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

    10/31/2024

    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
  8. Brock Weatherup. Secrets of Successful Sequels

    10/21/2024

    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
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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 - 2025
  • Episodes
    47
  • Copyright
    © Anastasia Koroleva
  • Show Website
    Exit Paradox

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