The Billionaire Trust Strategy You’ve Never Heard Of | Dan Pascone with Alessandro Chesser | Ep. 35

In this episode, Dan Pascone sits down with Alessandro Chesser, CEO of Dynasty, to break down one of the most powerful and least understood tax and estate tools used by ultra-wealthy founders and families. Nevada trusts layered on top of Qualified Small Business Stock (QSBS). They walk through how QSBS works, why some founders legally pay zero tax on tens of millions of dollars of gains, and how Dynasty is trying to “democratize” these billionaire-style strategies so they’re not just reserved for people with $100K+ legal budgets.

You’ll hear why timing is everything (especially for early-stage founders), how Nevada (and South Dakota) became trust havens, what it really means to “own nothing, control everything,” and why a simple $1,500/year decision early in a company’s life could be worth eight figures later on. If you’re building, working for, or investing in a high-growth C-corp tech company, this is a must-listen.

• Most wealthy families use trusts and most others should. A basic revocable trust avoids probate, cuts legal friction for heirs, and can prevent your estate from becoming a multi-year court battle. It’s often a major upgrade from “just having a will.”
• Nevada (and South Dakota) trusts are the advanced play. Properly drafted Nevada irrevocable trusts offer strong asset protection (from lawsuits and creditors), 0% state income tax, and the ability to move wealth across generations with favorable estate tax treatment.
• QSBS is one of the most powerful tax exemptions in the code. If you own eligible Qualified Small Business Stock in a C-corp (non-services business) and hold it for 5+ years, you may be able to exclude up to $10M (or more, depending on timing) of capital gains from federal tax.
• Trust stacking can multiply the QSBS benefit. Each qualifying trust can have its own $10M QSBS exclusion. By gifting shares into multiple irrevocable trusts for different beneficiaries, founders and early stakeholders may be able to legally shield tens of millions more from tax.
• Timing matters more than most founders realize. The best time to set this up is early, when shares are worth very little and you can gift them without chewing through your lifetime gift/estate tax exemption. Wait until your company is clearly valuable, and you’re constrained by that exemption.
• This is niche but the stakes are huge. Dynasty focuses narrowly on helping founders and large shareholders (typically 2%+ owners) of C-corp tech companies set up Nevada trusts for QSBS. The downside is small and fixed; the upside, in a successful exit, can be life-changing.

• [00:27] – Dan introduces Episode 35 and Alessandro, CEO of Dynasty, and frames the conversation around qualified small business stock and billionaire-style trust strategies.
• [01:16] – Alessandro shares his background: banking and trust training at large financial institutions, then nearly a decade building Carta’s sales org from $0 to $300M+ ARR.
• [02:45] – How Dynasty brings those two worlds together: software + trusts, focused on democratizing Nevada trusts historically used by billionaires.
• [03:32] – Trust basics: why a revocable living trust beats “just a will,” and how probate court can become an expensive, multi-year mess for families.
• [05:05] – Revocable vs. irrevocable trusts: what changes when you give up ownership, and why irrevocable structures open the door to asset protection and tax benefits.
• [05:47] – Why Nevada and South Dakota are the top trust jurisdictions in the U.S., and how their laws mirror some of the benefits people associate with offshore havens.
• [08:03] – QSBS 101: what qualifies, why C-corp structure matters, the 5-year holding requirement, and how the $10M federal gain exclusion works.
• [09:29] – The Roblox example: how creating 12 separate trusts allowed the CEO to unlock roughly $120M in tax-free gains using QSBS and trust planning.
• [10:47] – Founder psychology: “I just want to build the company” and why waiting to think about trusts and QSBS can be an expensive mistake.
• [11:32] – Gift and estate tax constraints: the $14M lifetime exemption and why early gifting, when shares are nearly worthless, is the sweet spot.
• [12:52] – How Dynasty productizes this: $1,500/year for up to four Nevada trusts low fixed downside, potentially massive upside if the company wins.
• [15:07] – The “aha moment” for Dynasty: seeing an investor at Carta pay zero tax on $40M of gains while others paid full freight and realizing how few people could afford that structure.
• [16:51] – Recent QSBS-related tax discussions in the news and how that has increased awareness, even if most founders still don’t fully understand the rules.
• [17:35] – Who should pay attention: anyone owning ~2%+ of a non-services C-corp with real exit potential, not just the founding CEO.
• [19:39] – “When is it too late?” Why it’s almost never too late to plan, unless you’ve already burned through your lifetime gift/estate tax exemption.
• [20:39] – Lightning round: deep-dish pizza, favorite tech tool (Nola AI note-taker), Rockefeller’s “own nothing, control everything,” and starting a startup as a bucket-list win.
• [24:18] – Advice to his younger self: live more in the present, don’t be afraid to fail, and remember that family and health matter far more than financial wins.

Episode 35 of the Making Sense of Your Money podcast features Alessandro Chesser, CEO and co-founder of Dynasty, in a deep dive on how the wealthiest founders and families use trusts and QSBS to legally reduce taxes and protect assets and how those same tools can, in theory, be used by “mere multimillionaires” too.

Alessandro’s career arc sets the stage: he spent his early years in big-bank financial services, working directly with high-net-worth clients and getting trained on how to read and interpret trust documents. That’s where he first saw how common trust structures are among the wealthy. In the second half of his career, he joined Carta as its first sales hire, helped build the sales organization, and watched firsthand how equity, cap tables, and tax rules play out in real startups and exits.

He and Dan start with the basics. A revocable living trust, he explains, is often the “entry-level” tool that helps families avoid probate court. Wills must go through probate a slow, public, and sometimes contentious court process that can drag on for years. A simple revocable trust lets a successor trustee handle your estate privately, generally with fewer legal fees, delays, and family blowups.

From there, they move up the ladder to irrevocable trusts and, specifically, Nevada and South Dakota trusts. These jurisdictions have become onshore trust havens because of their favorable laws: strong asset protection from lawsuits and creditors (with some federal exceptions), 0% state income tax inside the trust, and the ability to pass wealth through multiple generations under very favorable estate tax rules. Alessandro frames it as the legal version of “own nothing, control everything” a Rockefeller-inspired idea that the truly wealthy have used for generations.

The conversation then zeroes in on Qualified Small Business Stock. QSBS is a section of the tax code that allows founders, early employees, and some investors in eligible C-corp companies to exclude up to $10M (and, for some, $15M) of gains from federal tax if they hold the stock for at least five years. That benefit is per taxpayer, per issuer. The catch: not all companies qualify (services businesses generally don’t), structure matters (C-corp vs. LLC/S-corp), and timing is crucial.

This is where Dynasty comes in. Alessandro explains that each qualifying irrevocable Nevada trust can have its own QSBS exclusion. By creating multiple trusts for different beneficiaries and gifting QSBS-eligible shares into each, a founder can multiply the tax-free benefit. He cites the well-known case of the Roblox CEO, who reportedly created 12 trusts and ultimately unlocked around $120M of tax-free gains using this strategy.

Dan pushes on founder psychology: when you’re pre product/market fit, staring down a hundred other fires, it’s tempting to ignore complex tax and estate planning. Alessandro agrees emotionally but argues that the math says otherwise. Early is best. When your shares are almost worthless, you can gift them into trusts without chewing up much (or any) of your lifetime $14M gift/estate tax exemption. Wait until traction is obvious and valuations are high, and the same planning becomes far more constrained.

Dynasty’s pitch is to make this practical: for a fixed $1,500/year, founders can set up and maintain up to four Nevada irrevocable trusts, with Dynasty acting as trustee and handling tax filings. If the company never takes off, the downside is a few thousand dollars over a few years. If it works, the upside could be tens of millions in tax savings and multi-generational asset protection. Alessandro is candid that this is a niche product aimed at a specific group: people who own ~2%+ of a non-services C-corp with real exit potential.

They also touch on the recent increased attention around QSBS in the media and policy debates. That visibility has led more founders to at least ask questions, even if they don’t fully understand the rules yet. Alessandro emphasizes that planning is almost never “too late” so long as you haven’t exhausted your lifetime exemption but the earlier you think about it, the more flexibility you have.

In the lightning round, Alessandro reveals his love for deep-dish pizza (Zachary’s and Little Star in the Bay Area, Gino’s East in Chicago), his favorite modern tool (Nola AI, a note-taking assistant for meetings), a classic quote that guides his strategy (“own nothing, control everything”), and his personal hacks as a busy founder and dad of two small kids (including shaving his head to save time). His parting advice to his younger self: worry less about the future, don’t fear failure, and remember that family and health matter far more than any exit or valuation.

Lightly edited for clarity and flow.

Dan: Brought to you by Tailored Wealth, helping business leaders live their version of a rich life.

Dan: Welcome to another edition of the Making Sense of Your Money podcast, where we cut through the financial noise and help business leaders make smart, confident money decisions.

Dan: Welcome to episode number 35 of the Making Sense of Your Money podcast. I’m your host, Dan Pascone, founder and CEO of Tailored Wealth. As always, each episode features a trusted voice in the financial world, bringing their expertise to help high achievers confidently make sense of their money.

Dan: Today I’m pumped. We’ve got a great guest with us. We’ve got Alessandro Chesser, CEO of Dynasty. He and his team are doing some really unique stuff in the qualified small business stock space. I’m excited to learn more. Thanks for joining us, Alessandro great having you.

Alessandro: Thanks for having me.

Dan: We’ve got a lot to cover. I know our audience wants to hear about your background, your expertise, and what you and your team are building. Give us a quick 90-second overview of who you are and what led you to found Dynasty.

Alessandro: Sure. The first ten years of my career were in financial services. My very first job was at Bank of America, then Wells Fargo, Washington Mutual I did the banking circuit. I was always on the sales side, helping high net worth individuals with whatever they needed: deposits, loans, investments.

Alessandro: That’s where I first learned about trusts and why the richest people use them to protect assets and reduce taxes. The banks trained us on how to interpret trust documents and how to talk to clients about them.

Alessandro: The second half of my career has been in Silicon Valley tech. I joined Carta as the very first sales hire in 2014. I ended up leading sales there for nearly eight years, helped grow the company from zero to over $300M in annual recurring revenue, and hired hundreds of people. I got a front-row seat to what it takes to build a business.

Alessandro: Now I’ve taken those experiences and started Dynasty with two co-founders who were also among the first employees at Carta. Dynasty really ties together the two halves of my career: financial services and trust knowledge on one side, and software and democratizing complex legal documents on the other.

Alessandro: We’re focused on democratizing the most powerful financial instrument available to Americans today trusts and, more specifically, Nevada trusts. These are the structures billionaires use to protect assets from lawsuits and creditors and to reduce taxes.

Dan: There’s a lot to unpack there. Let’s start at the foundational level. I talk a lot about the strategies wealthy people use, especially around taxes. Why do the wealthiest people use trusts? Then we’ll get into this Nevada trust concept.

Alessandro: At the broadest level, the main use case for a trust is to help your family access your assets after you die without going through probate court. That’s the mass-market use. Most people think, “I just need a will.” But wills have to go through probate. Trusts don’t.

Alessandro: Probate is a 12 to 18 month process, sometimes much longer I’ve seen it drag on for 5–6 years, especially if the family doesn’t get along or someone contests the will. When you die with only a will, the government has to process your estate through the court system.

Alessandro: With a simple revocable trust, you’re creating a separate entity that will process your estate after you die, through a successor trustee you appoint – not through the courts. So you avoid a lot of fees, delays, and legal battles. Probate can tear families apart; anybody can show up and make claims. It’s messy and expensive.

Alessandro: We sometimes call probate the biggest “tax” on non-rich Americans. People think they’re fine because they have a will, but the will is exactly what drags them into probate. A basic revocable trust solves most of that.

Alessandro: Beyond that, there are different types of trusts. Broadly, revocable and irrevocable. Revocable means you can revoke it you’re the grantor, you still effectively own and control the assets, and you can change it any time.

Alessandro: Irrevocable means once you create it and fund it, it’s permanent. You’re giving assets to beneficiaries and you can’t just pull them back. Because you’re giving up ownership, irrevocable trusts can offer stronger asset protection and potential tax advantages.

Alessandro: Nevada irrevocable trusts and similarly, South Dakota trusts are special because of the state laws. Dynasty is a licensed Nevada trust company. We set up and maintain Nevada trusts and serve as trustee.

Alessandro: Nevada and South Dakota have the best laws in the country for asset protection and taxes. Properly drafted, a Nevada trust is extremely difficult for creditors or plaintiffs to penetrate. If I live in California and I’m sued there, a California judge generally can’t force distributions from a properly structured Nevada trust.

Alessandro: On top of that, there’s 0% state income tax at the trust level, and very favorable rules that allow trusts to last for hundreds of years, moving wealth from my kids to their kids to their kids, without incurring estate tax at each generation the way a normal estate might. There are additional tax benefits depending on the type of trust you use.

Alessandro: At Dynasty, we’re a full-stack Nevada trust company. We create the trust, we act as Nevada trustee, and we file the trust tax returns. We’re unique in doing all three.

Alessandro: But we’re not trying to be everything to everyone on day one. Our initial focus is narrow: startup founders and others with Qualified Small Business Stock. We help them unlock more QSBS benefit using Nevada irrevocable trusts.

Dan: Let’s go there. Explain QSBS qualified small business stock from a founder’s standpoint. What is it and why does it matter?

Alessandro: QSBS gives you, depending on when the company was formed or the shares were issued, roughly $10–$15 million in tax-free capital gains when you sell. It’s available to founders, early employees, and certain investors in qualifying small businesses.

Alessandro: The company needs to be a C-corp, not an LLC or S-corp. It can’t be primarily a services business. Tech companies and product companies usually qualify; pure services firms usually don’t. And you need to hold the shares for at least five years.

Alessandro: If you meet those tests and then sell your company or your shares, the first $10M (or $15M for some newer issuances) of gain per taxpayer per company can be 100% excluded from federal tax. It’s arguably the most powerful tax exemption in the code.

Alessandro: For simplicity, I usually talk about the $10M number, because for companies issuing shares before mid-2024 that’s the relevant cap.

Alessandro: Now, anybody with QSBS-eligible stock can potentially use that $10M exemption. What we do is help people get more of it by creating trusts. Each qualifying trust gets its own $10M QSBS exclusion.

Alessandro: So, for example, the CEO of Roblox created 12 trusts that held Roblox stock. When they went public, those 12 trusts each had their own QSBS buckets. That’s how he reportedly realized around $120M in tax-free gains. It’s all public; it’s been written up in the New York Times.

Dan: Very cool. Let’s walk through the journey of a typical SaaS founder. They’re pre–product/market fit, they’re trying to survive, maybe thinking about QSBS. How do you help them? What does it look like?

Alessandro: First, we aren’t the ones who make you QSBS-eligible. You need a good lawyer and a platform like Carta to get the structure right C-corp, proper documentation, meeting the QSBS requirements. We have partners who can help with that if needed.

Alessandro: Once your company is set up to qualify, we step in to help you get more QSBS coverage. We help you create Nevada irrevocable trusts for beneficiaries kids, parents, siblings, spouse, whoever you choose. You gift some of your shares into each trust. Each trust now has its own QSBS cap.

Dan: The founder mindset question: “I just want to build the company, I’ll worry about taxes later.” What do you say to that?

Alessandro: It’s totally understandable emotionally. You’ve got fires everywhere when you’re building a startup. But it’s a bit of a chicken-and-egg problem. If you wait until you have serious traction and a high valuation, your stock is already very valuable and you’re constrained by the lifetime gift/estate tax exemption.

Alessandro: Right now, that exemption is about $14M. You can gift up to that amount during your life without paying gift tax. Every dollar above that is generally taxed at 40% federally, plus possible state tax.

Alessandro: The best time to set this up is early, when your shares are worth close to zero. You can gift them into trusts, preserve your entire exemption, and let the growth happen inside the trusts. The only real risk is the money you spend on the structure.

Alessandro: Our pricing is $1,500/year for up to four trusts. If your company flames out in three years, you’ve lost $4,500. That’s the fixed downside. If it hits, the upside is potentially $40M of extra gain sheltered from tax. So the asymmetry is pretty clear once you see it that way.

Dan: How are you getting this in front of founders who are so busy?

Alessandro: Right now, mostly through social and direct conversations. LinkedIn, Twitter, podcasts like this. Education is a big part of it QSBS is more well-known now, especially after recent tax discussions, but the trust stacking angle is still pretty niche.

Alessandro: And then when I get on calls with founders or early employees, we walk through their cap table, what they own, what the potential exit scenarios look like, and whether this planning is likely to matter in their situation.

Dan: You mentioned your “aha” moment. What made you think, “There’s a company here”?

Alessandro: At Carta, one of our investors did this used multiple trusts to get roughly $40M of gains tax-free. Meanwhile, people like me sold stock and paid full tax. That contrast stuck with me.

Alessandro: When I dug in, I realized this kind of planning typically cost hundreds of thousands of dollars in legal, trust company, and tax work. That makes it inaccessible to all but the ultra-wealthy.

Alessandro: The startup insight was: if we can standardize and software-enable this, we can dramatically lower the cost and make it accessible to a much broader slice of founders and early shareholders. It’s very niche, but the value per customer is huge if it works.

Alessandro: It also fits a classic startup playbook I learned from Peter Thiel’s writing. Start with a tiny, underserved niche in our case, QSBS-eligible founders of C-corp tech companies and aim to own that niche. Once you own it, you can expand outward inch by inch. You don’t start by trying to “do everything for everyone.”

Dan: Has the recent tax talk around QSBS changed your conversations with founders?

Alessandro: Yes. It’s created awareness. Even if people don’t fully understand the rules, they’ve heard “QSBS” and know it’s important. That makes the first conversation much easier. We’re not starting from zero anymore.

Dan: Who should be thinking about this most seriously?

Alessandro: As a rule of thumb, anyone who owns about 2% or more of a non-services C-corp with real exit potential. That includes founders, co-founders, some early employees, and some early investors.

Alessandro: Why 2%? Rough math: on a $1B exit, 2% is $20M. If you only use your personal $10M QSBS cap, you’re paying full tax on the other $10M. With trusts, you might be able to shield more of that.

Alessandro: There are also long-running bootstrapped tech companies where the founder owns 80% and will never see a billion-dollar exit, but their personal outcome could still be tens of millions. For them, this is very relevant too.

Dan: Why does QSBS exclude services businesses?

Alessandro: The intent of QSBS is to encourage investment in innovation product and technology and to create jobs and growth. Congress wrote the rules to favor that kind of economic activity. Pure services businesses don’t fit that policy goal as cleanly, so they generally don’t qualify.

Dan: When is it “too late” to think about this?

Alessandro: It’s almost never too late, as long as you haven’t already used your lifetime exemption. You can still gift into trusts even if your stock is very valuable. The tradeoff is you chew up more of that $14M exemption right away.

Alessandro: You still might want to do it, because most wealth managers will tell you that getting appreciating assets out of your name and into trusts is important. It’s just more elegant and flexible if you do it early, when the stock is worth very little.

Alessandro: It’s “too late” in a narrow sense if you’ve already used your entire lifetime gift/estate tax exemption on other transfers. Once you’ve used it, you can’t use it again. That’s why we try to get people thinking about this when their shares are still cheap.

Dan: That’s a great breakdown. Let’s shift gears and let the audience get to know you a bit. You’re officially entering the lightning round. First thought that comes to mind ready?

Alessandro: Let’s do it.

Dan: Coffee or tea?

Alessandro: Coffee.

Dan: One meal for the rest of your life what is it?

Alessandro: Pizza. Not the healthiest, but my favorite.

Dan: Any specific spot?

Alessandro: I’m a deep-dish guy. In the Bay Area, I love Zachary’s and Little Star Little Star might be my top pick. In Chicago, Gino’s East.

Dan: You’re in the Bay now are you from there originally?

Alessandro: Yeah, born and raised.

Dan: You’re a tech guy now. What’s one tool or piece of technology, other than your computer or phone, you can’t live without? Hardware or software.

Alessandro: Nola AI. It’s a note-taker for meetings. It transcribes calls into digestible notes. It doesn’t record video; it just takes notes. For someone doing lots of sales calls, it’s a game changer for tracking and follow-up.

Dan: Love that. Favorite quote or phrase about money or success?

Alessandro: “Own nothing, control everything.” It’s attributed to John D. Rockefeller. It captures the essence of trust planning. If you give assets away to a trust, you don’t legally own them anymore, but you can still structure things so there’s control and benefit for your family. That’s the whole game.

Dan: Favorite book on finance or business?

Alessandro: How to Win Friends and Influence People by Dale Carnegie. It’s the best sales book I’ve ever read, even though it’s not framed as a sales book. It’s not about tricks; it’s about being a genuinely good person, listening, caring about other people’s interests, and communicating from that place. If you do that, you naturally become more influential.

Dan: Do you have a personal hack you can share with the audience?

Alessandro: I shave my head. No haircuts, no styling, no time wasted. I’ve got a startup and two little kids two and four so every minute counts.

Dan: Love it. What’s one bucket-list item you’ve already accomplished?

Alessandro: Starting a startup. That was always on the list.

Dan: And a milestone you’re currently working toward?

Alessandro: Raising our Series A.

Dan: Last one: if you could give one piece of advice to your younger self, what would it be?

Alessandro: Live more in the present. Don’t obsess over the future or beat yourself up over the past. Don’t be afraid to fail. In the grand scheme, the stuff we worry about exits, valuations, titles isn’t what matters most. What really matters is my kids, my wife, our health and happiness. Once you have kids, it becomes very clear that most of the small stuff doesn’t matter.

Dan: Totally agree. If listeners want to connect with you, collaborate, or learn more about Dynasty, where should they go?

Alessandro: LinkedIn or Twitter. Just search for “Alessandro Chesser” and you’ll find me. You can also look up Dynasty from there.

Dan: Awesome. Alessandro, thanks so much for sharing your time and insights today. Really cool stuff.

Alessandro: Thanks for having me.

Dan: That’s it for the episode. You can find our podcast along with our newsletter and YouTube channel all for free at makingsenseofyourmoney.com. And as always, prioritize your version of a rich life.

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