StarZero All shows Try the podcast clipper →

Alessandro Chesseri

Co-founder & CEO, Dynasty · 1 appearance on the record.

computed by AI from the episodes · how this works → · full disclaimer →

founderexecutiveoperator@SandroChess ↗LinkedIn ↗getdynasty.com ↗

Alessandro Chesser is the co-founder and CEO of Dynasty, a digital trust and estate-planning platform for founders and startup employees. Previously, he served as an early executive and VP of Sales at Carta, scaling company revenue to over $300 million in ARR.

17statements → 10claims → 6claims resolved → 67%fully supported → 4.12/5average certainty → 1.47/5average debate potential → ≈4.5/5argument clarity, estimated → 1said about them ↓

4 supported 1 partly supported 1 contradicted 4 not checkable as stated how the 10 claims stand · each chip opens the sources

1 prediction · 9 assertions · 2 insights · 5 disclosures · every statement was checked. The prediction and assertions are the 10 claims: statements the public record can support or contradict. 6 are resolved, and 4 name no date, number or outcome precise enough to check. Everything else (opinions, insights, what ifs, disclosures) can never be settled by the record, so it carries no assessment.

The record, in short

What the tape says about how Alessandro argues and how the claims held up. Everything they said, and everything said about them, is in the tabs below.

Their most notable supported claim

Assertion Supported
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 …”
Alessandro Chesseri Aug 22, 2024 ▶ 11:19 The Revocable Living Trust Cheat Code for SaaS Founders (Save millions on taxeS)

Their most notable contradicted claim

Prediction Didn’t hold up
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.”
Alessandro Chesseri Aug 22, 2024 ▶ 22:21 The Revocable Living Trust Cheat Code for SaaS Founders (Save millions on taxeS)

Expressed certainty vs assessment result

none yet certainty 1
none yet certainty 2
none yet certainty 3
75% certainty 4
75% certainty 5

weighted support: a fully supported claim counts one, a partly supported claim counts half. Each filled bar is clickable and opens exactly those claims; "none yet" means nothing said at that certainty level has resolved yet

How they sound: not measured why? →

We measure speaking style by listening to the audio itself, and a fair number needs at least 2,000 words from one person on tape we have measured. There is too little of Alessandro Chesseri on measured tape to publish a rate. This says nothing about how they speak.

Everything Alessandro Chesseri said on Top Founders that made the record, most notable first. Filter by type, assessment or year in the ledger →

Assertion Supported
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 …”
Alessandro Chesseri Aug 22, 2024 ▶ 11:19 The Revocable Living Trust Cheat Code for SaaS Founders (Save millions on taxeS)
Assertion Supported
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.”
Alessandro Chesseri Aug 22, 2024 ▶ 10:21 The Revocable Living Trust Cheat Code for SaaS Founders (Save millions on taxeS)
Insight
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…”
Alessandro Chesseri Aug 22, 2024 ▶ 17:02 The Revocable Living Trust Cheat Code for SaaS Founders (Save millions on taxeS)
Assertion Supported
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.”
Alessandro Chesseri Aug 22, 2024 ▶ 1:53 The Revocable Living Trust Cheat Code for SaaS Founders (Save millions on taxeS)
Prediction Didn’t hold up
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.”
Alessandro Chesseri Aug 22, 2024 ▶ 22:21 The Revocable Living Trust Cheat Code for SaaS Founders (Save millions on taxeS)
Disclosure
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.”
Alessandro Chesseri Aug 22, 2024 ▶ 23:54 The Revocable Living Trust Cheat Code for SaaS Founders (Save millions on taxeS)
Insight
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…”
Alessandro Chesseri Aug 22, 2024 ▶ 26:27 The Revocable Living Trust Cheat Code for SaaS Founders (Save millions on taxeS)
Disclosure
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 …”
Alessandro Chesseri Aug 22, 2024 ▶ 3:29 The Revocable Living Trust Cheat Code for SaaS Founders (Save millions on taxeS)
Disclosure
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.”
Alessandro Chesseri Aug 22, 2024 ▶ 5:13 The Revocable Living Trust Cheat Code for SaaS Founders (Save millions on taxeS)
Assertion Supported
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.”
Alessandro Chesseri Aug 22, 2024 ▶ 5:47 The Revocable Living Trust Cheat Code for SaaS Founders (Save millions on taxeS)
Assertion Partly supported
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.”
Alessandro Chesseri Aug 22, 2024 ▶ 12:14 The Revocable Living Trust Cheat Code for SaaS Founders (Save millions on taxeS)
Assertion Not checkable as stated
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.”
Alessandro Chesseri Aug 22, 2024 ▶ 18:45 The Revocable Living Trust Cheat Code for SaaS Founders (Save millions on taxeS)
Assertion Not checkable as stated
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.”
Alessandro Chesseri Aug 22, 2024 ▶ 21:42 The Revocable Living Trust Cheat Code for SaaS Founders (Save millions on taxeS)
Assertion Not checkable as stated
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.”
Alessandro Chesseri Aug 22, 2024 ▶ 22:09 The Revocable Living Trust Cheat Code for SaaS Founders (Save millions on taxeS)
Assertion Not checkable as stated
Chesseri: Dynasty's total monthly operating expenses are under $40,000
“Less than 40,000 dollars a month.”
Alessandro Chesseri Aug 22, 2024 ▶ 27:41 The Revocable Living Trust Cheat Code for SaaS Founders (Save millions on taxeS)
Disclosure
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.”
Alessandro Chesseri Aug 22, 2024 ▶ 5:41 The Revocable Living Trust Cheat Code for SaaS Founders (Save millions on taxeS)
Disclosure
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.”
Alessandro Chesseri Aug 22, 2024 ▶ 21:08 The Revocable Living Trust Cheat Code for SaaS Founders (Save millions on taxeS)

The other half of the tape: Alessandro Chesseri's own voice is left out of every number here. 1 statement on the record names them. every mention, with the transcript →

Statements about Alessandro Chesseri, by other people (1)

Assertion Partly supported
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.”
Nathan Latka Aug 22, 2024 ▶ 0:47 The Revocable Living Trust Cheat Code for SaaS Founders (Save millions on taxeS)

Appearances (1)

EpisodeDateSpeaking time
The Revocable Living Trust Cheat Code for SaaS Founders (Save millions on taxeS) Aug 22, 2024 17m
Made with StarZero

Turn any episode into a week of clips.

This entire site, over 2,600 episodes transcribed, diarized, checked and made playable, runs on the StarZero media pipeline. Drop in your own episode and the podcast clipper finds the moments worth sharing, cuts them, captions them, and reframes them for every feed.

Try the podcast clipper Learn more