Aug 22, 2024 · 29m · top-founders
The Revocable Living Trust Cheat Code for SaaS Founders (Save millions on taxeS)
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Get Dynasty founder and former Carta VP of Sales Alessandro Chesseri joins Nathan Latka to break down how founders can shield millions in taxes and protect intergenerational wealth using modern digital trusts and South Dakota trust laws.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Nathan holds 32.7% of the talking time here. How this is scored →
Nathan as informed peer 6.0 Guest teaching 4.3 Guest disagreement 1.3 Nathan pushing back 3.3
speaking balance: gold is Nathan, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 15:52 Guest rejects divorce scenario jurisdiction premise
Alessandro interrupts Nathan's hypothetical scenario to firmly point out that real estate physically located outside South Dakota cannot be sheltered under South Dakota trust laws.
Hardest push from Nathan ▶ 22:45 Host challenges build vs. buy for trust licenseNathan aggressively questions why Dynasty is spending nine critical months applying for a license rather than using their fresh capital to acquire a smaller licensed firm.
Biggest teaching moment ▶ 10:45 Masterclass on QSBS multiplication via trustsAlessandro breaks down how sophisticated founders establish multiple irrevocable trusts for family members to stack $10M QSBS exemptions and shield up to $50M in exit proceeds.
Nathan holds their own ▶ 19:59 Host audits traffic and programmatic SEO liveNathan displays deep marketing expertise by analyzing Dynasty's programmatic SEO site architecture and verifying social channel subscriber counts in real time.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Nathan as informed peer | Guest teaching | Guest disagreement | Nathan pushing back | Why |
|---|---|---|---|---|---|---|
| Unpacking Carta's B2B Flywheel and Network Effects | 6 | 2 | 1 | 2 | Nathan showcases solid SaaS domain knowledge by outlining the standard AE quota playbook and asking how Carta engineered its multi-sided network effect. Alessandro details how Carta mandated cap table invites for both investors and law firms to create an organic flywheel. | |
| The Genesis of Get Dynasty and Seed Fundraising | 5 | 4 | 1 | 3 | Nathan benchmarks Dynasty's seed valuation and dilution against standard market terms. Alessandro explains the regulatory rationale behind raising $5M, specifically South Dakota's $1M liquid reserve requirement for corporate trust licensing. | |
| Tax Strategies for Founders: QSBS Stacking and Avoiding Probate | 6 | 6 | 1 | 3 | Nathan frames a concrete $10M exit scenario to press on state tax liabilities and probate pitfalls. Alessandro educates on why standard wills still get trapped in probate court and illustrates how founders stack multiple QSBS exemptions across trusts. | |
| Corporate Trustees, Retaining Control, and Strategic Wealth Moves | 7 | 5 | 2 | 5 | Nathan raises practical founder concerns around losing control, divorce paper trails, and borrowing against trust collateral. Alessandro clarifies the legal boundary separating digital assets from physical real estate in South Dakota trusts. | |
| Growth Engine, Funnel Monetization, and Trust Licensing Roadmap | 7 | 4 | 2 | 5 | Nathan references live Ahrefs data and YouTube metrics to dissect Dynasty's programmatic SEO and influencer marketing, then challenges why they don't acquire an existing licensed trust company. Alessandro explains the banking division's strict vetting process. | |
| Founder Best Practices, Market Positioning, and Perpetual Dynasty Trusts | 5 | 5 | 1 | 2 | Nathan questions competitive positioning against incumbent legal software and search ad bidders. Alessandro clarifies how perpetual dynasty trusts bypass the 40 percent generational estate tax. |
Statements from this episode (18)
Chesseri claims he grew Carta to over $400M ARR as VP Sales
“Prior to Dynasty, he was VP of sales at Carter, where he took the company from zero to over four hundred million dollars in ARR.”
Chesseri: Carta pioneered requiring companies to onboard their investors
“Every time we signed on a company, we forced them to invite their investors into the platform, which was kind of a unique thing at the time. Cap table management providers weren't actually getting investors to use the product as well.”
Chesseri: Carta aimed to become private markets' DTCC, transfer agent, and broker
“We wanted to be, you know, the entire stack in the public markets, you have brokerage account, you have brokerage accounts, right? And so we wanted to be the brokers for the employees and the investors. We also wanted to be the transfer agent and we wanted to …”
Chesseri: Get Dynasty raised $2M friends-and-family and $2.5M seed round
“Friends and family was about two, seed round was about two and a half.”
Chesseri: Dynasty maintains over three years of runway
“We have a lot of, we have like three plus years of runway. We're keeping expenses super low.”
Chesseri: South Dakota trust licensing requires $1M in reserve bonds
“We're becoming a licensed trust company in South Dakota, and that's going to require us to have a minimum of a million dollars on reserves. It filed via a bond.”
Chesseri: South Dakota trusts eliminate state income and capital gains taxes
“If those shares were held in a South Dakota trust in South Dakota, there is no state taxes for income or cap gains. So you save 1.3 million dollars right out of the gate just by having your trust in South Dakota.”
Founders can multiply $10M QSBS exemptions using multiple irrevocable trusts
“And so for federal taxes, if you want to save more money on federal taxes, what you do is you create a revocable trust and you gift your shares to your children or to your spouse or to your relative, your brother. And each of those trusts that you create gets …”
Chesseri: Only exercised shares can be moved into irrevocable trusts
“You can't move options into an air vocal trust. You have to move exercise shares into an air vocal trust.”
Founders can transfer wealth by paying rent to trust-owned homes
“If the trust buys real estate, they can rent to live in that real estate. So they're not directly connected. So for example, like, let's say I have my daughter I'll create an irrevocable trust for my daughter. I'll use the proceeds of sale to buy a house. I'll…”
Chesseri: 80% of Dynasty Customers Come From Word-of-Mouth and Short-Form Video
“Close to 80% of our customers right now are just coming from word of mouth and organic short form videos.”
Dynasty Spends Under $5K Monthly for 20-25 Short-Form Videos
“We can get it done for, you know, less than 5000 dollars a month and get like 20, 25 videos a month.”
Chesseri: Dynasty Has Roughly $50K ARR From $99 Product
“So we're not necessarily, we say we're pre-revenue, but we actually have about 50,000 dollars ARR, and that's coming from the 99 dollar a year product.”
Dynasty Has Driven Over $100K in Revenue to Bridgeford Trust
“Bridgeford Trust Company and they charge 8000 dollars a year and we've given them, you know, a hundred plus thousand dollars in revenue.”
Chesseri: Dynasty Will Secure South Dakota Trust License in Nine Months
“We're getting licensed in the next nine months. We're working on the application process right now. We're working with the South Dakota legislators. We're building our board in South Dakota and we'll be licensed in about nine months.”
Bill Ackman, Insight Partners' founder, and Carta's founder invested in Dynasty
“Bill Ackman is one of our investors. We have the founder of Insight Partners, one of our investors. We have the founder of Carta. We got a bunch of billionaires as investors.”
Chesseri: Dynasty trusts avoid the roughly 40% estate tax across generations
“When you have a regular revocable trust and you die, your trust has to be settled. It has to be paid out, which means estate taxes. The state debt tax is about 40%. If you have a dynasty trust lives forever. It gets passed from generation to generation to gene…”