The Ledger

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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)
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