Trusts Build Fortunes! How Alessandro Chesser Scaled Dynasty with Ackman & TikTok
Release Date: 06/06/2025
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Ever felt like you were just making the rich richer—without building anything for yourself? In this episode, Yair Klyman sits down with Ryan Bakke, a former Deloitte CPA who ditched the corporate grind to build a multimillion-dollar online tax and real estate advisory business. Ryan shares how a rooftop conversation with a Big Four partner triggered his Shawshank Redemption-style escape plan—and why he now helps everyday earners become wealth builders through tax strategy and real estate. You'll learn: Why depreciation is a “legal cheat code” for real estate investors The 7 steps...
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What happens when your biggest dream shatters—but you refuse to quit? In this raw and powerful episode of Resilient Riches, Yair Klyman sits down with Barak Schwartz—a former basketball player turned elite trainer, turned digital media force—whose journey is anything but ordinary. Barak shares how repeated injuries derailed his basketball career, but instead of giving up, he channeled that setback into helping others. Then, after the tragic loss of his close friend at the Nova Festival on October 7th, Barak made a life-changing decision: to become a voice for truth, identity, and Israel....
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Most 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 After building Carta into a multibillion-dollar startup, Alessandro turned his attention to the outdated world of estate planning—and built a scalable, VC-backed disruptor doing 30,000+ trusts in...
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Trusts Build Fortunes! How Alessandro Chesser Scaled Dynasty with Ackman & TikTok
The Resilient Riches Podcast
Most 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...
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Bring God into Your Business with Reb Adam (Audio)
The Resilient Riches Podcast
What if the missing link to your business growth isn’t strategy or hustle—but spiritual alignment? In this powerful and deeply personal episode, Yair Klyman sits down with Reb Adam Yitzchak Polinovskiy—social media influencer, spiritual coach, and guide to CEOs, UFC fighters, and high-achievers seeking more than just success. Together, they unpack how aligning your business, values, and spiritual identity isn't just fulfilling—it’s effective. Reb Adam shares how he went from disconnected atheist to a deeply committed spiritual teacher and coach, integrating teachings from...
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.