Skip to resource content
Founder conversationBuilder <$5m

How Dynasty Gets 2,000 Free Signups a Month and $50K ARR From Living Trusts

Alessandro Chesser explains how Dynasty uses a free revocable trust as its acquisition engine, and how South Dakota irrevocable trusts can cut founders' tax bills at exit.

Alessandro Chesser · Dynasty

Published August 22, 2024
Watch the full conversation
About this resource

Explore the lesson. Sign in to access the resource library.

What you’ll learn

Alessandro Chesser, co-founder and CEO of Dynasty and a former VP of Sales at Carta, explains how Dynasty gives away a free revocable living trust to feed a paid funnel, with about 2,000 signups a month and roughly $50K ARR. He also walks Nathan Latka through why founders use South Dakota irrevocable trusts to reduce state tax and multiply the QSBS exemption before an exit.

Read the source passages

Key moments

Find the ideas you need and go straight to the source.

Carta's forced investor invite flywheel

“But 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.”
Watch at 01:53

Free revocable trust as acquisition

“We're using the revocable products as our acquisition. That's the mass market product.”
Watch at 26:10

South Dakota trust state tax saving

“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 $1,300,000 right out of the gate just by having your trust in South Dakota.”
Watch at 10:15

Cost of short-form video content

“we get it done for, you know, less than $5,000 a month and get, like, 20, 25 videos a month.”
Watch at 21:42

$50K ARR from the $99 product

“we actually have about $50,000 ARR, and that's coming from the $99 a year product.”
Watch at 22:10

Resource files

About the speaker

Alessandro Chesser

Co-founder & CEO · Dynasty

Company revenue
$50K

More founder interviews