Trusts Build Fortunes! How Alessandro Chesser Scaled Dynasty with Ackman & TikTok
Release Date: 06/06/2025
The Resilient Riches Podcast
What happens when one of the world’s top war experts refuses to stay silent? In this powerful episode, Yair Klyman sits down with John Spencer - Chair of Urban Warfare Studies, internationally recognized war scholar, and one of the leading voices countering disinformation since October 7th. Spencer has briefed global leaders, advised the IDF, and been quoted by Prime Minister Netanyahu himself. Here, he unpacks: The “Israeli Standard” - how double standards in warfare law and media bias are reshaping global perception. The dangerous role of disinformation and why silence is not an...
info_outlineThe Resilient Riches Podcast
What happens when one of the world’s top war experts refuses to stay silent? In this powerful episode, Yair Klyman sits down with John Spencer - Chair of Urban Warfare Studies, internationally recognized war scholar, and one of the leading voices countering disinformation since October 7th. Spencer has briefed global leaders, advised the IDF, and been quoted by Prime Minister Netanyahu himself. Here, he unpacks: The “Israeli Standard” - how double standards in warfare law and media bias are reshaping global perception. The dangerous role of disinformation and why silence is not an...
info_outlineThe Resilient Riches Podcast
In this episode of the Resilient Riches Podcast, Yair Klyman sits down with the incredible Rose Han — one of the world’s top financial influencers and author of the new #1 Amazon bestseller At A Zero — to unpack the exact steps she used to go from six figures in debt to building a multi-million dollar net worth, and how you can start doing the same no matter where you're starting from. 🔑 Topics we cover: The Zero by Zero framework to grow wealth step-by-step How to escape the paycheck-to-paycheck cycle (even if your expenses feel fixed) The truth about W2 jobs — and how they...
info_outlineThe Resilient Riches Podcast
In this episode of the Resilient Riches Podcast, Yair Klyman sits down with the incredible Rose Han — one of the world’s top financial influencers and author of the new #1 Amazon bestseller At A Zero — to unpack the exact steps she used to go from six figures in debt to building a multi-million dollar net worth, and how you can start doing the same no matter where you're starting from. 🔑 Topics we cover: The Zero by Zero framework to grow wealth step-by-step How to escape the paycheck-to-paycheck cycle (even if your expenses feel fixed) The truth about W2 jobs — and how they...
info_outlineThe Resilient Riches Podcast
What does it really take to build wealth that lasts? In this powerful session, Yair shares his personal journey of watching his family lose everything — and the lessons that came from rebuilding smarter. Together with his father, he developed the Resilient Riches Blueprint, a framework for creating wealth that can withstand taxes, inflation, market crashes, and life’s unexpected turns. You’ll learn: Why most people unknowingly follow generic, broken financial advice How to align your wealth strategy with your values and lifestyle Practical ways to minimize taxes and maximize...
info_outlineThe Resilient Riches Podcast
What does it really take to build wealth that lasts? In this powerful session, Yair shares his personal journey of watching his family lose everything — and the lessons that came from rebuilding smarter. Together with his father, he developed the Resilient Riches Blueprint, a framework for creating wealth that can withstand taxes, inflation, market crashes, and life’s unexpected turns. You’ll learn: Why most people unknowingly follow generic, broken financial advice How to align your wealth strategy with your values and lifestyle Practical ways to minimize taxes and maximize...
info_outlineThe Resilient Riches Podcast
What begins as a press trip to Qatar ends with house arrest in Israel. In this powerful episode of Resilient Riches, host Yair Klyman sits down with Zvika Klein, Editor-in-Chief of the Jerusalem Post, to explore the high-stakes world of media, politics, and narrative control. Zvika shares his dramatic personal story of being invited to Qatar, pulled into an unexpected investigation back home, and ultimately becoming the focus of a nationwide debate about truth, credibility, and democracy. Beyond the headlines, this episode dives into: Why Israel has struggled to control its own narrative —...
info_outlineThe Resilient Riches Podcast
What begins as a press trip to Qatar ends with house arrest in Israel. In this powerful episode of Resilient Riches, host Yair Klyman sits down with Zvika Klein, Editor-in-Chief of the Jerusalem Post, to explore the high-stakes world of media, politics, and narrative control. Zvika shares his dramatic personal story of being invited to Qatar, pulled into an unexpected investigation back home, and ultimately becoming the focus of a nationwide debate about truth, credibility, and democracy. Beyond the headlines, this episode dives into: Why Israel has struggled to control its own narrative —...
info_outlineThe Resilient Riches Podcast
Most high achievers chase success at full speed — but too often, they cross the finish line in poor health, exhausted, and unable to enjoy the rewards they’ve worked so hard for. In this episode of Resilient Riches, Yair Klyman sits down with performance coach, nutritionist, and author Ryan Munsey (F Your Feelings) to explore how health and wealth are not opposing forces — they’re partners in long-term success. You’ll learn: Why controlling your calendar is the foundation of peak performance How to use time-blocking to protect your health, family, and focus time The critical...
info_outlineThe Resilient Riches Podcast
Most high achievers chase success at full speed — but too often, they cross the finish line in poor health, exhausted, and unable to enjoy the rewards they’ve worked so hard for. In this episode of Resilient Riches, Yair Klyman sits down with performance coach, nutritionist, and author Ryan Munsey (F Your Feelings) to explore how health and wealth are not opposing forces — they’re partners in long-term success. You’ll learn: Why controlling your calendar is the foundation of peak performance How to use time-blocking to protect your health, family, and focus time The critical...
info_outlineMost people don't realize that the wealthiest individuals quietly use trusts to protect and transfer their assets—while everyone else gets stuck in probate court, paying unnecessary fees and taxes.
In this episode of Resilient Riches, Yair and David Klyman sit down with Alessandro Cheeser, founder of Dynasty, a tech-forward trust company that’s turning the traditional legal industry on its head. After building Carta into a multibillion-dollar startup, Alessandro turned his attention to the outdated world of estate planning—and built a scalable, VC-backed disruptor doing 30,000+ trusts in just 2 years.
You’ll learn:
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Why revocable trusts are one of the most powerful (and underused) tools in personal finance
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How Alessandro’s team digitized trust creation—making it as easy as updating your social profile
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The difference between revocable vs. irrevocable trusts—and how the wealthy use them to protect assets from lawsuits, creditors, and taxes
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How to raise capital from elite investors like Bill Ackman and the founder of Insight Partners—even if you’re a first-time founder
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Why traditional Facebook ads are dead, and how influencers + TikTok are reshaping customer acquisition
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The smart strategy behind giving away your product for free—and making money elsewhere
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What startup founders can do to eliminate $10M+ in capital gains taxes
Alessandro also shares his personal journey—from working as a bank teller at 16 to building legal tech companies that are reshaping industries. If you're a founder, advisor, or simply someone who wants to understand how real wealth is built and protected, this episode is a must-listen.