Why successful founders fail the second time – post-exit playbook with Anastasia Koroleva

Get Steve’s full jet-buying guide in our free newsletter: https://truewealthshow.com/download-guide/ Sold your business and thinking about building again? Your second company could be more dangerous than your first. In this episode, True Wealth hosts Anthony Ng Monica and Fintan Costello sit down with Anastasia Koroleva, an entrepreneur who achieved a nine-figure exit and has spent more than a decade studying what happens to founders after financial success. Anastasia explains why experienced founders can still struggle the second time around, including the founder who poured more than $100 million into a business they knew they should have left years earlier. She also reveals why making life too easy after an exit can backfire, how your decision-making changes after selling, and the three founder archetypes that can help you work out what to build next. You’ll learn: - The fastest way exited founders can lose their wealth - Why your second business may be harder than your first - The $100M mistake successful founders can make after an exit - The 3 founder types: Artist, Architect and Allocator - Why founders often make their worst decisions after selling - How to choose work that still motivates you after financial freedom - Anastasia’s unconventional approach to raising ambitious children around wealth About Anastasia Koroleva: Anastasia Koroleva is an entrepreneur and exited founder who achieved a nine-figure exit early in her life. After her own second business failed, she spent more than a decade studying successful founders and the psychology of life after an exit, helping entrepreneurs understand what to build, how to make better decisions and how to find fulfilment once money is no longer the main goal. Follow Anastasia: - Instagram: @exitparadox - YouTube: https://www.youtube.com/@ExitParadoxPodcast - LinkedIn: https://www.linkedin.com/in/anastasiakoroleva Follow True Wealth: - Instagram: @truewealthshow - TikTok: @truewealthshow - Anthony on LinkedIn: https://uk.linkedin.com/in/anthonyngmonica - Fintan on LinkedIn: https://nl.linkedin.com/in/fintancostello - True Wealth website: https://truewealthshow.com/ 00:00 — Why successful founders fail the second time 02:20 — The second-time founder trap 05:50 — The fastest way to lose your exit wealth 10:42 — Why the “easy” second business often fails 16:09 — How to choose what to build next 18:35 — The 3 founder types: Artist, Architect and Allocator 23:00 — What Elon Musk, Steve Jobs and Peter Thiel do differently 30:07 — Why successful founders still need hard problems 32:07 — The post-exit path to apathy 40:17 — How to make better high-stakes decisions 41:18 — Why founders make bad decisions after an exit 48:17 — How much of success is actually luck? 59:05 — How to raise ambitious children after wealth 1:10:50 — Her son became financially independent at 15 Book a direct call at Daily Body Coach with Anthony: https://www.dailybodycoach.com/ #truewealth #exitedfounders #entrepreneurship