Democratizing Wealth: Alessandro Chesser on Building Dynasty and Lessons from Carta’s Early Days

What if the same wealth tools billionaires use were accessible to everyone?

In this episode of First Builders, hosts Amber Illig and Rachel Tsui sit down with Alessandro Chesser, Co-Founder & CEO of Dynasty, a licensed Nevada trust company helping founders and investors maximize equity value through smart ownership structures like QSBS stacking.

Before founding Dynasty, Alessandro spent eight years at Carta, joining as the company’s first sales hire and helping scale revenue from zero to $300M. Along the way, he learned how ownership structures shape outcomes—not just for investors, but for founders and employees too.

In this conversation, Alessandro shares:
– Lessons from building Carta’s early sales and culture
– Why trust and education are the missing pieces in equity strategy
– How Dynasty is democratizing complex wealth tools like Nevada trusts
– The risk and reward behind becoming a licensed trust company
– Why compassion and clarity are underrated founder superpowers

It’s a candid look at what it takes to build credibility, complexity, and culture—from a first builder who’s done it twice.

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LinkedIn: https://www.linkedin.com/in/alessandrochesser
Dynasty: https://getdynasty.com

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Transcript

0:04

Welcome to First Builders, the podcast for those who shape companies from the ground up. I'm Amber Illig, founder and general partner at the Council Capital, where we invest in early teams solving critical problems in essential industries. And I'm Rachel Choi, partner at the Council. This show is about the people behind the playbooks, the ones who take a leap early and help define what their companies would become before anyone else could see it. Today's guest is one of the few founders tackling a space that's rarely discussed but deeply important. How to maximize equity value through smart ownership structures. And before founding Dynasty, Sandra spent eight years at Carta, helping companies and investors manage cap tables, valuations, and equity. He started as Carta's first sales hire in 2014 and became VP of sales, driving company revenue from zero to over 300 million. Even though Carta is still private today, early employees have had some opportunities to cash out their equity. Now with Dynasty, he's helping founders and investors leverage QSBS stacking, which is a tax strategy that can significantly increase how much value they keep from their equity. Alessandro, welcome to First Builders. Thanks for having me on the show. Yeah, super excited. Well, let's dive in. Um, would love to start with your time at Carta. Um, we know you started in sales there. So, what did working inside a fast scaling fintech tell you about ownership and equity strategy? I learned a lot. But one thing that was very clear to me in the very beginning was the most successful, the repeat founders that were working on their second companies, they always created a bunch of trusts. And in the very beginning, that was literally what we were all doing. We were all helping up sales we got. We had to all pitch in. Salespeople were also onboarding companies. So I did a, you know, probably a couple hundred onboardings myself. And seeing seeing trust, especially with the repeat founders, was definitely the the you know eye-opening moment for me when it came to structuring equity and with what the most successful people did. Yeah, no, that's actually that's really fascinating to me. So hearing, and if I hear this correctly, like the sales folks, like including yourself, would kind of be like the customer success onboarding, you know, folks as well. So interesting that that was the case for you guys, but probably a great way to ensure that you really establish that trust with their with your customers and with those founders. Yeah, and it got crazy. There was one month, it was probably December 2015, where we were we had to shut down, we had way too many customers. Uh, it was a very good thing. But we we signed up so many customers that we had this huge, massive onboarding backlog, and we literally shut down sales for the entire month. And all the sales, I had a sales team of like 15 or 20 at that point, and we all were doing onboardings. Yeah, it was it was a fun experience. We were still selling, we were just uh pre-selling for January, we were post you know, DLC. Wow, that's an incredible problem to have. Was there a moment where you thought, like, while a lot of just seeing the disconnect between like first-time founders and second-time founders, we see that in other areas where like second-time founders just know how to leapfrog certain issues, and even we believe first builders that have been early inside of companies know how to leapfrog certain issues and get ahead faster. But related to that insight that you had about the trusts, was there a moment when you thought, wow, you know, these first-time founders kind of have no idea what they're missing out for? Uh yeah, I would love to hear more about that. Yeah, I was something specific, not related to trust, kind of related, but just QSBS in general. You know, when we it was 2014 and we hired an ex um PWC tax accountant on our onboarding team, actually. Um, and that individual was really early career, like 23, 24 years old. And he was explaining to us in a like town hall company meeting, and we were like, I don't know, 15, 20 in place. He was explaining to us what QSPS was. And um, some of the senior leaders in the company, including our CEO Henry and our general counsel, that was the most surprising one of all, but our general counsel who came from Cooley were basically saying, Oh no, that sounds too good to be true. Don't believe him about QSPS. And they were telling us not to exercise because the company was risky. They didn't want us to like, it was coming out of a good, good spot of not wanting us to take the risk of exercising our shares. But some of the employees took that advice of not exercising, didn't exercise. By the time they did, we raised too much money and they weren't able to take advantage of QSPS. You have to exercise your shares before the company had the old rules, before the company has $50 million on its balance sheet. And so they didn't, we ended up raising a big fundraising round for our Series C. And you know how it is. By the time the rank and file employees learn about the fundraise, it's over, there's already a term sheet. It's too late. They can't exercise. It's already in the news, basically. They missed it and they didn't even know that QSPS was a real thing at that point either. And um, on the other hand, I believed that the PWC count, regardless of what our CEO and general counsel said, I said, you know what, I'm gonna exercise. And I was a little bit later in my career than some of the other employees, so I had the means of being able to exercise. I think that's one of the things that makes it difficult for early employees, is they can't afford and usually it's cheap, but there's still a cost associated with it in the beginning. Um, and so I exercised and I got to take advantage of QSPS, at least for one exemption. And so just seeing that, like, you know, that's the type of thing that our CEO, Henry, if he ever starts another company again, I guarantee you he's gonna tell everybody about QSPS. Second time founder, like knows what it is, gonna educate the employees, tell them, hey, if you believe in this company, you should actually exercise your stock because it's gonna help you benefit from qualified small business stock treatment. So, you know, it's important if you believe in the company to exercise. And it's also important at the company level to make sure that employees can early exercise their options. In order to be able to early exercise their options, there needs to be a specific clause in the company formation documents that allows them to early exercise. And not all companies allow that, and they don't even know. Like when you form your company, like our law firm didn't really go over the, they're just like, here's our standard documents. We had to ask them like, hey, we want to be able to early exercise because otherwise employees can't start the clock, the the five-year clock for QSPS. If they can't exercise, they have to wait till the shares vest. Um, and so and there's other tax implications with not being able to exercise early, because the best time to exercise is right away when you get the shares, because there's no actual gain at that moment in time. So when you exercise, there's gonna be no alternative minimum tax as due because it's just it's even you you got the shares at the price that the company is valued at today, so it's a wash. Versus if you wait to 12, 24, 36 months, now you exercise. Now you have this huge gain that's gonna be reflected in alternative minimum tax. You're gonna end up having to pay a ton of taxes just to exercise your shares. Yeah. But you gotta have a lot of trust, right? Like that the company is going to do well and you know, to to make that decision. And it sounds like you had that. I was curious, like, what made you you know have that um intuition about it? What made you stay at Carta also like for so long as well? Henry convinced me on my initial interview, not immediately at the interview, but when I went home and I reflected on it, and it was a very interesting interview. The first time I met him, he was like barefoot and he like was whiteboarding and he was he was like, here's the stock market that exists today in the public markets, here's all the infrastructure that exists in the private markets, and it was like law firms, spreadsheets, and he's like, We're gonna recreate the entire stock market, but for private companies. And I had some experience in the private cap table space. I worked for the incumbent, and uh, and so I was like, no, that's not possible. That's against the law, has to be paper. I debated him, and I'm the natural debater as a salesperson, so I'm like arguing with him, and then I went home and I thought about it, and I was actually talking to a friend of mine about the interview, and I started like taking Henry's side and I was debating, I was like, here's what Henry was saying, and here's what he thinks. And in that discussion with my friend, my friend's like, Well, sounds like you should just join then. And I was like, You're because I made such a compelling case for what Henry was saying. And so then I reached back out to Henry and I said, Hey, I know I argued with you in the interview and I didn't think it was possible. I said, But now I believe. And I just was completely at that moment, like I believed in the mission of the company. And so, you know, I I told him I probably gave up a little too much leverage. I said, I'll join, you know, and that was before he made me an offer. So he ended up making me the lowest offer ever. And, you know, I joined anyways, but um, it all worked out. That's really interesting. Yeah, we talked actually one of the top three things we look for and founders in the first conversation is do they have a huge vision for what they're building and not just where they want to exit the company and the numbers, but more like do they see the world in a different way with their product in it? And it's funny because it's almost like bordering on delusion. You have to really sort out like who's delusional versus who has a real vision that could come to life. So I love that you saw Henry as he's like, you know, just as close to that edge as you want to be to be able to build something big. So that's super cool. Reality distortion, that's what they call it, right? It's the Steve Jobs thing. Henry made us read a book called Presentation Secrets by Steve Jobs, and it talked a lot about that. That's awesome. And now today you've decided to found your own company after that eight-year run at Carta. So, first of all, congrats on the run. It's insane to go from zero to three hundred million ARR at any company anywhere, especially joining from the early days. So that's awesome. But what made you leave and and even want to leave and start a company? You know, honestly, like I come from an immigrant family. I would have never started a venture-funded startup. I probably would have been a small business owner, but not a venture-funded startup with the risk connected to it. You know, I would have never done it unless it was the perfect situation, which is I made enough money at Carta, have my nest egg, I was able to buy a couple houses, and I had perfect co-founders. My one of my good friends that I had worked with for over a decade, who was our first product manager hire at Carta, he always wanted to start a company. So me and him were always talking about it. And then I became really good friends with employee number one at Carta, the engineer that built the platform. And so we kind of talked about it together a lot. You know, we have sales, product, and engineering. We're like, we're a perfect fit to start a company. We can do a lot by ourselves. And so the stars aligned, like everything kind of came together, including the idea. Uh the idea for Dynasty came to me from one of the smartest people I know. He was running our strategy team at Carter at the time. He's a Stanford guy, super well connected. He has his own startup now, but he put together this like memo on Dynasty, and he was like presented to me because I was the go-to-market person for the company. I was working, you know, running sales and finding product market fit for all the new businesses. And he was like, ow, this is what Carter should do next. And he had it all documented. And uh that to me was the light bulb moment of like, yeah, this should exist. It wasn't until later when I was like, okay, maybe we'll start a company. And I was chatting with that individual again, and he was and I reminded him of his idea that we never nobody ever did. And he's like, Yeah, you should start it. I'll invest right now. And that's what kicked off the company. So it was the perfect situation. Yeah, it's like you had the friction removed. It was like you you had the nest egg, you had the person saying, I want to be your first investor. Here's the idea, here are the people. That's awesome. Yeah, that's amazing. And for our listeners out there, can you tell us a little about the core problem that Dynasty is solving today? Yeah. So I mean, we saw this, you know, with the richest people were creating trusts and optimizing taxes, and everybody else wasn't. And that's like the core problem is like the richest people have access to the best tools that allow them to gain advantages, and the rest of us don't. And that's like the core problem. But, you know, the more we drilled into because trusts are like there's a lot of companies kind of tackling the trusted will space already. Uh, there's trust and will, there's Rocket Lawyer, there's LegalZoo, there's all, you know, probably a dozen other brand new startups that are all tackling the trust and will space. Um, but the deeper we dug into it, the more we realized that the biggest area that needs to be democratized is not the regular trust, but the complex trusts and the Nevada Trusts, for example, or the Wyoming or Delaware Trust, the South Dakota Trust. There's like a handful of states that have the best laws in the United States for trusts. And so we we kind of drilled into that and we're like, we want to open this up for anyone, not just the regular trust that your parents may have, but the trust that the billionaires use. And that was the trust that allowed for, you know, QSPS stacking when we saw it, like those were the trusts that were being used. They weren't the regular trust, they were the irrevocable South Dakota or Nevada trusts. And so the more we learned about this kind of hidden world of trusts, and there's a whole bunch of like content on the internet about like South Dakota Trust and Nevada Trust, and like that's where all the billionaires keep their money. And it's like the new Switzerland. It's not only for people in the United States, but for people offshore as well. They're moving money to South Dakota, they're moving money to Nevada. The more we learn about that, like why? Well, it's because of taxes, it's also because of asset protection, it's also because of privacy. Like everybody should be able to use these. Like maybe the taxes only the richest people can benefit from, or the startup founders, but the asset protection, anybody should be able to benefit from that. You know, if I have if my life savings is $50,000, why can't I protect that from lawsuits, divorce, whatever? Like, why can't I protect it in an asset protection trust? The same way that Elon Musk can protect his assets, why can't I do the same thing? And so that, you know, we started seeing that, and our investors were are very focused on us being a mass market company, not a boutique go after the you know top 1% company. We want to be a mass market company, but we, you know, it actually had to become a licensed Nevada trust company. We we decided on Nevada. Nevada was a state that we wanted to offer trust in. Um, and in order to offer Nevada Trust, you needed a Nevada trustee. And so we had to become a licensed Nevada Trust company. It was took a couple of years, cost a couple million dollars. We just got our license a few months ago. And so we have this big bold mission of bringing Nevada Trust services to the masses. We had to go take a couple steps back and figure out, okay, well, what's the first market we want to capture? And uh it wasn't, again, I won't take any credit for it at all. It was another, it was our investors, one of our investors specifically, who said, get as narrow as you can, find a market that has, you know, a viral network effect. And they're like, you know what? It's startup founders, it's QSPS Trust, which is kind of the reason why we started this to begin with. And it's the market that we know, it's the go, you know, go-to-market that we know, it's it's the network that we have, it's viral. You sign on one founder, they introduce you to two more co-founders, and they introduce you to their friends, and then their investors are asking questions. You know, we we know how to do it. So it's just made perfect, and it's our own problem as well at this point. So we're like, perfect. So we launched it. So we're starting with founders, but the goal is to expand, kind of go after and capture this first market and then expand it inch by inch into the masses. So from founders to executives at startups to general partners of venture firms to limited partners of venture firms and to small business owners, you know, to the masses and getting all the way to the homeowner. Like that's the big mass market opportunity. That's so cool. And I love your focus on the mass market, like building something for the 99%, not just the top 1%. Um, I feel like there's been so much discourse for years, but even heating up recently around billionaires, and everybody's almost asked, like, pick a side. Do you love them or do you hate them? Um, you know, personally, I I like some, I dislike others. I think they're all humans who can kind of choose the impact they want to have while they're here. But obviously, one of the main things that they're criticized for is, you know, all these tax breaks and paying less taxes than everybody else. And I liked your take on, I think it was on LinkedIn the other day. You said, like, hey, instead of, you know, us constantly complaining about them, why don't we do something about it and just focus on how do we democratize all these things they're taking advantage of and make sure everybody has access. So I love that you're tackling it. And it it seems like you you have to chip away at a big block, but even the first chip is like huge, like being able to tackle this QSBS problem. So it's like it's like getting every day we're unpeeling more and we're like we have founders that are selling their companies for hundreds of millions of dollars and they own 70, 80 percent of it, and they're putting all it into a trust that we're gonna be the trustee of. So the opportunity is like huge. It's getting bigger and bigger and bigger. Um, and we haven't even, you know, scraped the surface of the market potential. Yeah, absolutely. I know obviously like the QSBS stocking is legal, but it's not widely used. Why do you think it's still under the radar today? First of all, you know, until now, most people didn't even know about QSPS. Like my like I said, my C CEO of Carta didn't know about QSPS. The general counsel didn't know about QSPS, right? From Cooley. And so, you know, that's like step one. Like people just don't know about it to begin with. Step two is like, if you do know about it, you have to usually talk to a family office to learn about stacking QSPS and then the costs associated with that. The old way of doing it, you'll pay over $100,000 to stack four trusts. Plus, you need to do like $10,000 a year in administration costs. So, like, you know, the only founders that could afford that were the successful ones at their either repeat founders or late stage founders. And the problem is at the later stages when the founders can afford it, that's when it is harder to do because you're limited. You can only gift up to $14 million in your lifetime without paying any gift taxes. So the the best time to stack trust is actually day one when your shares are worth zero, because you can stack as much as you want and you can preserve your lifetime exemption. The problem is expensive, so that's the problem we're solving, making it possible for founders to do from day one. That's awesome. Um, and what has some of the the first builders type work been like at Dynasty, building things from zero to one and kind of skipping back, you know, it had been eight years since you've been in those early days. What has building the product, educating the market, and convincing founders to act early been like? So hard. So hard. Like I joined Carta as zero ARR, but Henry already had a lot of stuff done. And I didn't, you know, respect that. I didn't understand that. He always told me, like, oh, you have no idea. You have no, I mean, he was working on it for like two or three years before I joined, even with zero ARR, right? Like, it just takes time. And he, you know, he he struggled to fundraise and he's talked about it a lot publicly. And so, you know, in the beginning, getting the license was very difficult and and expensive. And fundraising, until now, it's gotten a little bit easier, but fundraising has been it's not an easy thing to do, especially when you're tackling a market that's so everybody knows it's huge, but like building a consumer company, nobody wants to invest in consumer companies. Most investors I talk to are like, why don't you go BDP? Why don't you and I mean the challenger is like, no, we're going consumer. We're gonna do TikTok videos and Instagram. We did a lot of them. We did a and we generated a lot of consumer interest from TikTok videos and Instagram videos, but not a lot of revenue. And so, you know, now going backwards and like how do we launch this trust company business and generate strong enough revenue to build into this market and support the masses, you know, starting with founders, it just it's working from a revenue perspective and a viral network perspective. And so it was just picking the right market and and getting the license. And but like up until this point, we tried a bunch of different markets. Before we got licensed, we got a lot of one-time revenue, but not a lot of recurring revenue. And just figuring out how to market differently, like especially in today's world where you can't just go and send thousands of emails a day like you used to, or you can't go and buy Facebook ads like you used to. And like now you need to figure out like how to hack growth without spending any money. And so, you know, luckily the founder go to market, like we know it well. So it's just it's a network and you know, doing exactly what we're doing right now, right? Talking to investors, talking to law firm partners and doing webinars and getting founders, you know, the most important thing, you know, product-led growth. Like, create an experience so good that people tell all their friends and family about what they're doing. And the way that you're able to do that best is when you focus on one persona. Before we were more broad, before we got our license, and we're like, okay, we're gonna help people with their homes, we're gonna help people with their brokerage accounts. And like, we make nobody deliriously happy when you do that. If you want to create deliriously happy customers, you have to just focus on one problem and one customer type. And so for us, founders and founder stock, and that's it. And now we're creating deliriously happy customers. Now we have people going on LinkedIn and like posting about us without us asking them to do it because they're able to get this done in like a day. And it would have taken it for 2% of what it would have costed them otherwise. And so, yeah, that's why it's so important to just focus on one as narrow of a customer persona as you can. Yeah, no, definitely. And it sounds like, you know, it was like a hard-earned to get to that point, right? Especially when you went from kind of like going to the masses to now this kind of like deep focus on there. So switching gears a little bit, you know, thinking about how you're selling something that's really complex, right? It's compliance heavy, like you said, you had to get the license. How do you build that kind of trust with your with the founder quickly? Um, you know, how how does that happen for you guys? Yeah, that's a great question. And something that luckily I have a lot of experience doing at Carta. We had the same problem at Carta. I mean, at Carta, what we did was we got an opinion letter from DLA Piper. We paid a bunch of money. They gave an opinion on the validity of our uh electronic stock certificates. And so that was like uh I used that so many. And then I got a case study from Perkins Cuey. And so every time founder would doubt what we were doing, or their law firm would tell them that we're illegal because it's conflict of interest, like we were gonna cut into their law firm's fees. Then I would be like, no, look at this case study from DLA Piper, look at this. Or an opinion letter from DLA Piper. Look at this case study from Perkins Couie. And I would literally tell them, like, your law firm doesn't want to help you, go to Perkins Cooey. They'll help you cut costs by using our software. And so that's what we did at Carta. The equivalent of that at Dynasty, you know, no law firm wants to do an opinion letter on like trust documents, especially because all the law firms that actually know trust documents are competitors to us. And so, or they view us as a competitor. But what we've been able to do is we put together a really good group of partners that we work with that helped us come up with this package, including lawyers, including CPAs, but more most importantly, you know, Carta and Morgan Stanley. Morgan Stanley's probably the best one of all. I I've had the head of estate planning for Morgan Stanley review our trust documents, review our package and kind of bless it. And I've, you know, have teams at Morgan Stanley that we work hand in hand with now. And when I get a founder who is, you know, wants to make sure we're legitimate, I say, talk to my friends at Morgan Stanley Private Wealth. They only work with people with $100 million plus, but they'll talk to you and they'll talk to you about what we're doing and they'll help you set it up, like with us if you want. And obviously they have more interest in managing your money when you sell your company. So I just like obviously that's why they're willing to talk to you. But, you know, having those type of partners to be able to send people to to validate us and build credibility like is key at this stage. In addition to at this point, we're getting a lot of um customer referrals. Somebody signs up, they set it up, then they tell their friends, like that's the best. That that's how you establish credibility. Yeah. It's it's amazing that you've been able to get like those partnerships with um, like, you know, like Morgan Stanley, I'm sure, when you were trying to at least like land like their first couple founders, right? Like that was probably like a really key component. Yeah, and it actually wasn't that hard. I spent a lot of time with them now, but the reason why it's easy is because I'm not asking them to send me any customers at all. I'm telling them I'm gonna send them customers and they love it. And I send them customers. I sent them like three, like three, and like very, and the ones that I'm sending them are the ones that are like very successful, like hundred million dollars plus in the assets. And so they love it. They're like, they're all so like we'll review all your documents, we'll connect you with our CPA partners, we'll help you have the best package possible because they're looking at customer acquisition. Yeah. And so they love it. So that's why it's been easy to partner with them, is because I'm sending them all the customers. They haven't sent me, they've yeah, I think you've sent me a few, but we're acquiring the customers. So we we control everything. That's cool. Yeah, and and speaking of other learnings, you know, you recently shared a story from your time at Carta that really stuck with me. You wrote about launching a public markets platform, even though Carta was focused on the private markets at that time. They were wanting to kind of try this out in the public markets in 2018, integrating with infrastructure, enabling sell orders, selling to dozens of small pupp companies, and then kind of getting you getting the chance to land one of the largest IPOs of 2019. Um, so yeah, we wanted to ask a little bit about that. Good one. Yeah. And I actually I have the post pulled up, but I won't read the whole thing. But there's a couple of lines in there that I felt like really, you know, hit hard, right? Like product was telling me we weren't ready to support them, but I ignored the message. I pushed ahead in selling the deal. The customer trusted me, trusted Carta, and I was selling way too uh far ahead of the curve. And we ended up dropping the ball and it ruined our reputation. And my CEO is trusting me, and I'll never make this mistake again. So when product says we aren't ready, we aren't ready. Yeah, that's I mean, first off, I love how transparent you are and how candidly you share that story. Um, because it's a brutally honest reflection. And I'm sure a lot of people have stories like that um that they're not sharing on LinkedIn. But what made you decide it to share it publicly now? You know, in the day that we're in right now, um, you know, obviously just trying to get attention online is like, how do you do it? You can brag or you can be vulnerable. And I think not enough people are like truly vulnerable and just reflecting on like telling stories of where you've learned really hard lessons. And I just I was trying to think of like what I could talk about, like what's the biggest mistake I've made? And that was the one that I could think of. That was off the top of my head. You know, it was a huge pivotal moment. Like Carta could be supporting public companies right now, Carta should be supporting public companies right now because they have the all the pipeline for it, you know, and the amount of IPOs that have came off of Carta and the missed revenue uh opportunities, like is huge. And um, you know, I always believed that Carta could be a hundred billion dollar company. I still believe it. I still believe it, but that was one way that it would have been possible and we missed and we've and we failed. And you know, the whole vision at the beginning was we're gonna create a stock market for private companies. And that shifted around. And we also tried to do that. That was Carta X. But um, you know, it was like, okay, well, if we're not gonna create a stock market for private companies, let's just take them public because that's when the wealth is created. That's where the biggest opportunity is to make an impact on people's lives, but also the biggest opportunity to monetize, right? Especially when you raise Carter raised a billion dollars. Like if we have big, really big revenue targets, and where can we make the most money when our customers make the most money? And otherwise it's just a leaky bucket. You'd lose customers when they create the most value, when they make their money, you're not even capturing them anymore. You'd lose them. And so it was it was a big opportunity, and we failed to execute. And I own a lot of that. I own a lot of that. I think we did a really good job with that team, but I have a tendency to, you know, to have tunnel vision sometimes, and I pushed it too far. My head of product was telling me we were ready, and I was giving a different message to the CEO and the board members. And uh I was and this this worked for me a lot of times previously, like you push it through and you make it work, and you stay up until midnight every night and you make it work. Yeah. Uh but we were just so far from being able to support this one. Yeah. Again, it's uh kind of like that vision bordering on on delusion. It's like nine times out of ten, you hit it, and then like that tenth time, it's like, okay, yeah, probably should have listened. It was a it was a huge problem. And you know, like I said, most importantly, it lost our CEO's faith and us as a team. He disbanded the team and Carter never got into the public markets. Yeah. So it's unfortunate, but it's a really good lesson for me, especially now because we're in another heavily regulated industry, and if we mess up, like there's big major issues. And I think that was like one of the biggest reasons. Like my underlying like message was like, okay, we're not gonna do this with dynasty. Yeah. Like we did it last time, it's the same team. My head of product is my head of product now. He was a head of product for that business as well. And so now, you know, he's he will never, especially with what we're now we're completely in charge. Like, no, our product, it took three years to release it. We might have had the opposite problem this time. We took three years to launch it, but uh here we are. Yeah. And it sounds like, yeah, like you've really kind of uh carried that lesson with you, right? Like if you have and so I'm curious, like, you know, are you tempted ever like to close a big deal when the product's not truly ready yet? Or do you feel like that's something that you have like a much like harder look at, just you know, knowing what you know you've already experienced? Yeah, it definitely happened in this company already where we had some billionaires and wanted to create trust with us. And, you know, this was before when we were doing everything and we did it, and we support them now. And uh, you know, we're we're their trustee. And I actually tried to get out of that one and I told them, I was like, hey, we're not, you know, we we were this isn't normal business for us. Like you really should be working with your and they were like, Don't worry about it. We have all of our we have our family office reviewing everything. They're like, we just want to work with you because we like tech companies and so we support them and everything went good and everything's fine. But you know, now that won't happen anymore because we only work with founders and founder stock now. So like there's no founder that we can't work with. Like, if it's founder stock, we have this airtight package. And if there needs to be additional planning when it comes to like the tax side, we brope in our Morgan Stanley private wealth, we broke in our CPA partner, maybe an attorney partner as well. We bring the whole family office infrastructure. We still serve as the trustee. That's the business that we actually want. But so like we're not in position to sell ahead anymore. Like we only have one customer type that we work with, and we know it very well. Um, and then yeah, switching gears again, like what did Carta get right about scaling culture and product that you've brought into Dynasty? Yeah, Carta, Carta did a lot right in the early days. Culture, we had a cult. It was literally a cult. We were all bought in. I don't know like what I mean, it's just Henry just had a really effective way of selling the the vision of the company. And we were super close and you know, we had to be in person. Didn't matter if we lived in San Francisco, we had to commute down to Mountain View, and we did camping trips. We did like whitewater rafting, like we did a lot, like a lot as a small company. And the camping trips are great. Like, I hope to bring that back to Dynasty. We're still small, but could probably do it. But yeah, we did, I think culturally, like we all, you know, you have to really have a clear mission. I think that was the biggest takeaway that I have from that is you have to have a clear, clear mission for everybody to be like obsessed with. And the second part is you have to like motivate them to like or you have to hire the right people that are mission-driven towards your mission. And one thing that we did was weird, but you know, in the beginning we didn't have a lot, and we're actually doing it now again, but we didn't, you know, we didn't couldn't afford to pay top dollar is for Carter, we did this until pff probably until now. We always used we all the everybody we hired is like, look, we're not gonna pay the best. If you're looking for money, go work at Salesforce or Google or wherever. If you're looking to build a really big company that makes a big impact and have large upside connected to that with stock, this is the company for you. We tell them straight up, we're not gonna pay the best, not even close. We're gonna pay on the bottom end. And uh that attracted the right people. Like I think the people that were just looking for money would self-select out and the people that really believed in our mission, like me telling them that we're not gonna pay the best at all and we're not gonna negotiate. Henry has this whole blog post on like how to hire, and he says, we don't negotiate. We do the same thing now. He actually did the same thing with me when he hired me because he gave me a terrible offer and he knew I was gonna accept already. And I tried to negotiate, and he said, We don't negotiate. Here's why. I made you the best offer I'm willing to pay you. If I were to negotiate with you, you would wonder maybe I could have got more. At this point, no, this is the best you this is my best. This is my walk-away price. Now you know that you can trust me going forward. I joined and we do that at Dynasty now, and we did I did it at Cardiff with hundreds of people that I hired, and it were I the right people opt in for that type of environment, and it built really, really good culture. That's so cool. Yeah. I like how it's just straightforward, probably wastes a lot less time as well in the process because you're not waiting for a week for them to come back with a number and then you to think about it, quote unquote, and then get back to them. It's just it's a whole dance, and sometimes you just want to like both parties know where they're kind of willing to land, and it's better to just cut to the chase. So Henry Henry also believes that like negotiations were unfair because only certain type of people always negotiate and certain people never did. Yeah. And some are really good at it naturally, and then others try and they're just not so yeah, yeah. It does, it does like um level the the play, like the the playground essentially on that. So yeah. Um, so then conversely, is there anything like from Carta that you've intentionally like not applied a dynasty or anything that you're like, hey, we're doing this differently? That's a good question. You know, uh at Carta, we didn't have good data for how people should be compensated, not on the cash side specifically, but more on the equity side. And you know, we we a lot of the early employees believed that they were severely undercompensated from an equity perspective. And so what we actually one of the products I launched at Carta towards the end of my eight years there was a compensation tool, a Carta total compensation. And it you got all the CART data, all the equity data, created benchmarks. And we from day one were like, we're gonna use that and we're gonna show people the data and show them where we're compensating them. So building trust immediately. So Carta didn't have the ability to do that in the beginning because the tool didn't exist, but I think that was a lesson of like you want to build trust and not make people feel like they're getting ripped off later. Like, show them how you're coming up with the decision to pay them, and you're using data and you're intentionally paying them this percentile reflective against everybody else in the same position at the same size company in the same location. I think that's huge. Like we use that every every time we hire somebody now. I pull it up, I show them here it is, here's your role, here's where we're gonna pay you. Yeah. No negotiations for it. No negotiations. No, but it's so good because I think like, you know, people just need to understand the process. Like when it seems super opaque, which is it just feels a lot more like sketchy. Like you're just especially if you don't know what's happening. And once you know the process, at least you can say, Hey, I don't agree with the process, but at least I know what it is, right? Like, yeah. And then you make your decision from there. Yeah, exactly. Um, and then as a former first sales hire, turn VP of sales who managed hundreds of people in your time at Carta, what's your take now on the right time to make that first sales hire? When we are cons when when we are consistently, it's right about now. When we are consistently doing over $50,000 a month in new ARR, is that uh based on my experience of building a sales team? $50,000 a month is a good quota, $600,000 a year. Give them a total compensation that's 20 to 25% of that. And the numbers work. You can build a scalable sales team like around $50,000 a month in quota and just about where we're at right now. That's why I recently made a post about looking for a salesperson. Yeah, that's awesome. And helpful for you to share too, because I think uh a lot of times like founders get pressure from investors, like founder-led sales, founders-led sales, founder-led sales. And we definitely believe in founder-led sales because it's the best way to get quick feedback from customers and implement it directly into the product. And as a CEO, you can hop onto calls a lot faster and get to calls with people a lot faster than someone that works for you. Because you, you know, people see it in your title on LinkedIn. They're like, whoa, the CEO, the CEO or the founder's reaching out to me. Um, but there comes a time where things are breaking and there's other things you need to focus on. And it's helpful to know where you see that switch as being kind of worth it. Yeah. When I'm when I when I can effectively be a salesperson with the quota and carry my own bag, like that's when I can replicate it. And until I get to if if I'm not at the point where I can generate consistently $50,000 a month in revenue, then we haven't found product market fit yet. And if we haven't found it, I'm not going to outsource that. I have to do that. Totally. Yeah. Yeah. I love the perspective of like, yeah, it has to be once you get to that product market fit aspect. Yeah. And the product market fit definitions all, you know, there's so many different definitions. I like the one from Mark and Treason where when the customers are ripping the product out of your hands. But to me, it's like when it's when I'm a when the numbers work, the unit economics work for me to be a sales rep. Like when I'm when I'm able to be a commissioned sales rep myself based on the revenue I'm generating, then I'll hire, then I'll replicate that. Yeah. Spoken like a true sales turned founder. So love it. So yeah, so curious too, like, um, is there a time when you made a decision at Dynasty that felt risky at the time, but actually ended up paying off? We became a licensed trust company, it cost a couple million bucks. A lot of investors didn't want us to do it because it's highly regulated, it takes a long time, and they were like, you're too small to be thinking about that. But by doing that, it gives us a huge regulatory boat. Nobody else can do what we're doing unless they have that trust company license, which is a lot of money goes into doing it, a lot of time, and a lot of work. And so it's um it was risky uh because investors were like, that's a services business. Why are you but nope, there's no venture-funded licensed trust companies. We're the first. Uh, but now that we have it, it's enabled this new product, which is flying off the shelf. And it's the real, it's the first real time we've had product market fit in three years, and it's like reminds me of 2015 card all over again. The amount of interest that I'm getting from so many partners and so many customers, and like when I'm back to back to back to back, I had to change my sales calls to 15 minutes instead of 30 minutes to fit more in, and then I had to change it back because I'm like, I can't get this done in 15 minutes, it's like more complex. So like I have people that are like getting upset because they can't get on the phone with me for two weeks because my schedule's packed. Like, that's a good feel, but it's all enabled by this trust company license. So very happy that we another investor convinced me to do it, and all the credit goes to him. That's so cool. Um, I love that you're going after the complex problem first. Like Rachel and I were actually just talking about that earlier this week with another founder. But it feels like right now, especially in the age of AI, it is so hard to have defensibility. It's hard to build a moat, it's hard to show how you're different. Every everybody can like build something easily easy on top of something else. But when you really go for these, you know, regulatory challenges and big complex problems that most people don't want to solve, that's where the real opportunity's at. So that's super cool that you decided to take the risk and do it. Yeah. It's a good it's a good time. Go after the hard problems. Yeah. So with that, we'll transition to uh rapid fire questions. So we've just got a few and you can say whatever comes to your mind first. Um, but they're they're designed to be pretty quick. So Rachel, I'll let you kick off. Yeah. Okay. So what do you think is the most underrated skill for a founder? Compassion. I think a lot of founders are like, you know, tend to be very cutthroat. And I think that if you want people to follow you into the fire, like you gotta have compassion and you gotta care about them. And they if you want them to care about you, they you need to care about them. So not a lot of people talk about that. And there's a lot of cutthroat founders out there, but I think compassion is very important. Answer. And what's a book or concept that's stayed with you? How to win friends and influence people, another book that Henry made me read. I think I have that sitting on my shelf as you read it. Yeah. And it's just, you know, the core takeaway from that book that I got was be a good person. Speak in terms of the other person's interest, not your own. Like just do the right thing. If you if you're speaking terms of the other person's interest, like and you show them that like you're on their side, like you're gonna be able to influence them better. Just be a good person. If you want, you know, you want to influence people, be a good person. I'd be genuine. And then last one, what's a piece of startup advice that you think is total BS? I think there's like this, um, there's a lot of people that are like, you need to test and measure every single thing you can do you do. I think we try to do a lot of that and we're like, you know what? Like we're way too early. Like, we need there's some things you just have to go with your gut on. There's some things you have to go with your gut on. And you know, I think that if you can test and measure all day, every day, and still never find product market fit. And so it's just you can just create a lot of busy work for yourself. And so I don't think that's the answer for product market fit. I think there's a lot more art than science when it comes to product market fit. And I think a lot not a lot enough people give credit to that. Awesome. Uh, so we have one last question that we ask every founder that comes through here. Uh, so if you had a magic wand, imagine you get three wishes. What's one thing that you would fix for for founders, for yourself, and then for sort of the the industry at large, which you're operating in? One thing that I would fix is uh California's recognition of QSPS. It's like one of five states. So many companies here. So many all the companies are here, all the companies are and New York recognizes QSPS. Yeah. It's ridiculous. It's like California is gonna punish tech companies for being there because everybody wants to be here. It's like ridiculous. Like that's one thing that I would fix for all of tech. Absolutely. It makes no sense. It's speaks to California just not caring about us. Like we all live here, we all want to be it's a beautiful place to be, but like come on, one of five states. Yeah. Especially when we're so entrepreneurial. It makes no sense. It makes no sense at all. We're like, it's like being cocky, you know, like it's like, yeah, that would be the one thing that I could think of. That's awesome. And then what about something for you personally? One thing I would wish for yourself, yeah. Wish for myself. Um you know, I love being a founder, but I love being a father even more. And I wish that as this company progresses, that I can actually be more president instead of less president. Like that's that's like my biggest challenge. It's like it's you know, working hard on the company and the sleepless nights and like it steals from my young children. And the fear that I have is that the more successful we become, the worse it's gonna get. But my wish is that it's the opposite and the easier it's gonna get. Yeah. I truly believe with good good leadership skills, like you can grow your team and manage your team in a way that allows you to have a life outside of work. You know, obviously you grind for those first few years and first five years, it's always gonna be a lot of hard work. But, you know, I've seen people that have both, and I think it's possible. But it kind of comes back to even what you were mentioning before, which is like being a compassionate leader. I think people want to work hard for people like that. So and they probably want similar things to you as well. Yeah. Yeah, absolutely. That's cool. Awesome. Well, Alessandro, what's the best way for founders to get in touch with you? And is there anything that you would like to shamelessly plug? No, just best way to get a hold of me, probably LinkedIn. I'm more active there than anywhere else at this point. Twitter does not work for me at all. I'm in the same boat recently. Last year I was on fire. This year, not so much. So Yeah, it's tough. So LinkedIn, probably best way to get a hold of me and check us out. Plug just Dynasty. Check us out. Get Dynasty.com. If you're founder, if you're an angel investor, check us out. Yeah. And fun fact, I was an early customer of Dynasty too, even pre-pivots, but I'm excited about this new pivot too. So super exciting. But yeah, thank you so much for coming on the show. And that's it. Thanks, Alessandro. Really great to have you on. It was so nice to have Alessandro on, especially after we hosted a webinar with him. Um, curious, uh, Amber, what stood out to you from this uh conversation? Yeah, a few things. Hey, I've been following his journey for years, and it's funny, we were joking with him after the recording earlier that he feels like an extension of our team this past week because of that webinar that we did too. So, but you know, one I have we hadn't dug in with him in this way before. So it was really cool to hear how he thinks about company building. And I liked how he talked a lot about focusing in on one problem, one persona. And I think a lot of founders think they're getting specific because they get that advice. And then they try to go after that, they realize it's too big of a focus area. They get a little bit more specific, and that's when things really take off. So it seems like he had the same experience. And it's just a good reminder to everyone like get more specific, build something really tight for that market, and then have people clamoring after the thing that you're building for them because it's so specific to them. And then the other one that I really liked that came up was just his willingness to take the risk and get that license to create trusts in Nevada, which I, you know, I didn't realize it costs like $2 million to do that. And I can understand why early stage investors would be like, do you want to spend $2 million if you only raised like three or something? I don't know how much he's raised, but if you've only raised three to five million, you really want to spend two of it on that. And so being able to take that risk, I think has paid off a lot. And, you know, at the council, we love complex spaces because it is there are so many people building easy things right now and it's easy to build. And so it's it's just hard to stand out when it's really easy to replicate whatever you're building. So I think that just that's gonna set him apart and give them a lot of escape velocity, even if someone else else catches on to what they're doing and wants to do the same thing. Yeah, totally. And I think speaking of like that focus on the customer too and you know, being able to find that product market fit, I loved how he was been thinking about that as he transitions from founder-led sales over to actually making his first sales hire. Um, we talk a lot about this with founders of like when is that right time? And um, I think spoken like a true salesperson, you know, he thinks about it as, hey, do I have enough to actually make like the commission and have like, you know, dry the revenue perspective for like the first sales hire. So yeah, I really love that. He's been kind of focused in on that piece of it. Yeah, it's funny because my brother has also been a first sales hire at a scaling tech startup that didn't scale as big as Carta, but that was one of his biggest takeaways too, is like it is so hard to be a first salesperson or even an executive of sales or you know, a person hired onto a sales team if there isn't product market fit. Uh it's just an uphill battle. So even if you have downward momentum because your product is so good, that's when you really need salespeople to be able to take those calls, onboard people, teach them how the product works. So I thought that was really important for him to point out. Yeah, absolutely. We're gonna link everything that Alessandra mentioned in the show notes. And if you want more first builders like this, tune in for our next guest. Thanks for tuning in.