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The the largest fintech community in the world. Subscribe to our newsletter to stay up to date on the latest in news opinions, and all things financial technology.

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Signals Fintech Founders: Dynasty's Alessandro Chesser

On building “Morgan Stanley 2.0”, why the average American should have a trust, and what democratizing access to trusts means for the US tax system.

Signals Fintech Founders: Dynasty's Alessandro Chesser

Hey fintech friends - Dez here, I’m super excited to share my interview with Alessandro Chesser, the CEO & Co-Founder of Dynasty. We covered a ton of ground here: Alessandro's vision to build “Morgan Stanley 2.0”, why the average American should have access to a trust, and got into a bit of philosophical debate on what would happen if Dynasty is successful in their mission to “democratize trusts.” This was a super fun interview for me and I think you’ll all enjoy it. Let’s dive right in.

Alessandro, great to be chatting with you again. Could you tell us what Dynasty is, as well as give us a little context on your background?

Hey Dez, great to be here. At Dynasty, our mission is to democratize the greatest financial instrument the richest Americans use that the rest of us don't use today: The living trust. We are building a vertically integrated trust company for both simple trusts and complex trusts. 

So a little bit about me and my background– I actually started my very first job in financial services at 16 years old; I was at Bank of America selling financial services and financial products.

I spent close to a decade in the consumer banking circuit working for Bank of America, Wells Fargo, and Washington Mutual. Over time I ended up moving into the software world. I got my first software job at Silicon Valley Bank (I guess I worked for two companies– Washington Mutual and Silicon Valley Bank– that are both no longer here) within a group called SVB Analytics. They owned a software platform called CapMx that was a “Version One” of cap table software. 

Over time, I became the only salesperson for that product and because of that experience, I wound up at Carta as the first sales hire in 2014. Carta was zero-ARR when I joined. Henry specifically recruited me because he found out that I was the only salesperson for the incumbent's product, and he wanted to leverage the relationships and the knowledge that I had in the space to build his business. I ended up at Carta for eight years,  as VP of Sales I built the business from $0 ARR to +$300 million ARR.

Amazing. Could you bring us inside that journey a little bit?

The most important part of that journey was that I got to really flex that zero-to-one muscle. I got tons of experience going zero-to-one with brand new products. I helped launch the cap table product, the company valuation product, the investor valuation product, the expense accounting product, the tender offer product, the public markets product, the CartaX product, and the compensation product. Most of the products that Carta has, I served as the first business lead for. That zero-to-one muscle is what Henry liked to use me for. I also built up a 200+ person sales organization brick-by-brick, so I got to build that 1-N skillset as well.

That's incredible. Really diverse and varied background and lots of different jobs over the course of a career. How'd you get a job at Bank of America at 16? Did you just walk in and apply? Did you know someone?