484 Alessandro Chesser

Jeffrey Feldberg: [00:00:00] What if the most powerful wealth building tool isn't just for the elite, but for anyone with a smartphone?

Meet Alessandro Chesser, a FinTech trailblazer on a mission to democratize estate planning. As the founder and CEO of Dynasty, Alessandro is transforming the way Americans approach Wealth preservation by making living trust accessible, affordable, and digital Alessandro's journey began at 16 selling financial products at Bank of America.

His journey led him to become the first sales hire at Carta, where he played a pivotal role in scaling the company from zero to over 300 million in annual recurring revenue. Now with Dynasty, he's leveraging his extensive experience to simplify the complex world of trusts, aiming to make them a standard part of financial planning for all.

Through the innovative use of technology and a commitment to transparency, Alessandro is not only challenging traditional estate planning, but also addressing [00:01:00] systematic issues such as pay equity and financial literacy. His work is a testament to the belief that everyone deserves the tools to secure their financial future. 

And before we start the episode, a quick word from our sponsor, Deep Wealth and the Deep Wealth Mastery Program. Here's Sanjay, a graduate of Deep Wealth Mastery, and he says, the investment I made in the Deep Wealth Mastery Program, it's a rounding error compared to the value created today and the future value I'll receive.

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Man, I love that kind of feedback because it's that kind of feedback that's what gets me out of bed every [00:02:00] day.

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So if you're interested in growing your profits, preparing for a future liquidity event, whether that's two years away or 22 years away, and if you want to optimize your post exit life, Deep Wealth Mastery is for you. Please email success at deepwealth. com. Again, that's success, S U C C E S S at deepwealth. com. We'll send you all the information about Deep Wealth Mastery, otherwise known as the Scale for Ultimate Sales System. 

That's where you want to be. You want to be with other successful business owners, entrepreneurs, and founders, just like you, who are looking to create market disruptions. Whether you're a startup, whether you've been in business for three or four decades, whether you're manufacturing, whether you're high tech, SaaS, low tech, whatever the case may Come in and network with other [00:03:00] business owners, with other businesses, just like you, because they all want to lock in their financial freedom and enjoy both success and fulfillment.

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Deep Wealth Nation welcome to another episode of the Deep Wealth Podcast. Well, for all you business owners, founders, entrepreneurs out there, I've got a question for you. Would you like the inside track that when the time is right for your Exit, or perhaps you're doing some kind of family transition.

You have an above board way to secure financial freedom, your legacy in a way that you probably haven't heard of, but you should. Would you also like to hear from a founder who knows a thing or two about scaling? And if you said yes to both those things, you've come to the right place. We have a very special guest in the House of Deep Wealth.

Alessandro, welcome to Deep Wealth Podcast, and absolute pleasure to have you with us. There's always a story behind the story. What's your story? What got you from where you were to where you are today?

Alessandro Chesser: Yeah. Yeah. [00:04:00] Thanks for having me on the show. Everything that I've done in my entire career has led me to this point. My very first job at 16 years old was at Bank of America. Working with, high net worth individuals who came into the bank and needed help with their, investments or their bank accounts, or loans or whatnot.

In addition to the fact that they would come in with their living trust documents. And so the banks actually trained us on how to interpret these trust documents. How to, make sure that we knew how to talk about them with the clients. And so that was the very beginning of my career.

I spent almost a decade in financial services. And then after that, I ended up working for Silicon Valley startups. you know, worked for a few different ad tech companies. And then I ended up at a company called Carta. Who now is, a couple thousand employees. joined as the first sales hire in 2014, and over the course of eight years, we got up to about $300 million in annual recurring revenue.

And all we did at Carta was we helped startup [00:05:00] companies automate legal documents. Um, Startup companies and startup investors both. And so it was legal, tech and FinTech type of company. We created infrastructure for all of their share transfers from the company to the employees and to the investors.

Like literally created like a stock market for them. 'Cause none of that existed before for private. Startup companies. It was all in Excel spreadsheets and paper stock certificates. So we digitized the entire thing. And then, so just combining those two experiences, financial services working with, I knew exactly what trusts were.

And then second, like working on legal tech and FinTech and combined both of those experiences and I saw the next area that needs to be democratized, which is trust. And not just any regular trust, but the most powerful trust that the richest Americans use Nevada Trusts specifically Nevada and South Dakota Trust.

We, we chose to become a Nevada trust company specifically. But really it's any of these there's four or five states where the richest people have their trust in South Dakota, Nevada, Wyoming, [00:06:00] Delaware and these states have the greatest laws for asset protection and taxes and privacy. And so that's the business we're working on, democratizing now Nevada Trust for everybody.

Jeffrey Feldberg: Okay. Wow. My goodness. There's a lot to go in there. And so we're gonna talk about what you're doing now on the financial side and trust, but before we do offline, you had briefly mentioned that, and you mentioned it just now, from a scaling perspective with Carta, I mean, my goodness, you're one of the first hires there.

The company has gone places when it comes to scaling. Obviously the larger that we can scale our companies, Alessandro, the more you're gonna be able to help us with what you're doing right now. So it's really a win-win from that perspective. When it comes to scaling, looking back, what's the one thing as entrepreneurs that maybe we're just missing the boat on, or we're simply not doing, or we're just doing it wrong, that can make all the difference for us.

Alessandro Chesser: You know, There's a lot of lessons that I took from my experience at Carta and I would say one of the, so scaling and product market [00:07:00] fit has its own challenges. You're talking about scaling, which is separate from product market fits once you already have product market fit, like how do you scale it?

I would say one thing that I learned, which was very important, it's counterintuitive advice, and it comes from my old CEO of Carta Henry. He wrote this blog post on how to hire. And so, the traditional way of hiring employees is you're scaling as you're, exceeding growth Targets and you need to hire people very fast. The old kind of mantra is be very careful with who you hire. Go slow, spend lots of time with them and be very calculated in the hires that you make. Well, Henry had the opposite approach and he was like, listen, you can spend all your time with somebody interviews and you can do the Google tests to make sure that they're smart.

He's in the end of the day, whether an employee's gonna work out or not. It's really a coin toss. Like maybe they're gonna be fit, maybe they're not. 'cause it's not just like, are they capable? It's are they gonna end up fitting in culturally? Are they gonna end up being motivated? Are they gonna like the mission of the company?

There's all [00:08:00] these additional factors that go into how effective they end up becoming. And so Henry's big, statement is like. Hire fast. Fire fast, move forward. Nobody's good at hiring, so don't try not to be too smart about it and make decisions quickly. And if they work out it works out.

And if it doesn't work out, let them know quickly because that's gonna be better for the company, but it's also gonna be better for them personally. Nobody wants to drag out of relationship where, like I think it happens to be the situation when you spend months on like hiring the right person and then finally you hire them.

You usually have a sense like right away of whether or not it's gonna be a good fit after they start. And like it's not working out right away, but like you spent so much time like looking for them, so you really wanna make sure this is gonna work out. You're gonna extend it out months and try to give them the right feedback and coaching.

Usually it's not gonna work out and you're gonna end up waiting, maybe six months of your time wasting six months of your time just from hiring, looking for the right person. It still ends up not working out. And then you're slow on making the decision to let them go because you're like, oh, I just, [00:09:00] there's all this sunk cost into going into this.

And so Henry's, his whole blog post is called How to Hire and anybody can just search it and reward how to hire. He talks about hire fast, fire fast is very important for startup companies. You don't have time to waste. And, make decisions quick.

Jeffrey Feldberg: Yeah. I love what I'm hearing and as you're talking about that, yeah. Hands up guilty as charged. I was one of those guys back in my startup. I would do all the tests. I would bring candidates in. I remember I would give them case studies and spend hours and more times than not, you're right.

Even where on paper was a fit. In reality, it was. And so what I'm hearing you say is two things when it comes to scaling, it's all about the people, number one, and then number two. Hire done's better than perfect. Bring the people on board and if you're seeing some red flags early on, it's probably a good indicator.

Don't try and stretch it out and make that tough decision that you have to and hire. No, it's may work out, it may not work out and not, okay, fine. And if it has, terrific, but don't let the hiring process slow you down in terms of the scaling up [00:10:00] and getting to where you want to get to. How am I doing with that?

Alessandro Chesser: Yeah, that's exactly right. And there's a very famous example that Henry uses in his blog post, which is I think it's one of the founder of Instagram and he actually interviewed with Facebook, and Facebook turned him down for a job and then he ended up starting Instagram and it ended up.

Acquiring Instagram and it costs Facebook like multiple billion dollars to have to acquire Instagram. And so he, it ended up being very successful acquisition for them, obviously. But the point is Henry used to say false positives are okay. False negatives or not, like turning down the person that ends up being the right fit can cost you greatly, like hiring the person that ends up being the wrong fit.

You can quickly fix that after the fact.

Jeffrey Feldberg: Okay. Lots going on there and you both nation some words for the whys for you. Soak in that and just run with that. Give it a try. Hey, done's better than perfect. Bring the person on board. When you have an opening, see how it goes. And again, the [00:11:00] analysis of paralysis. All those other things that come to mind, just do it.

To borrow another thing. Just do it and see where that takes you. So it's actually a great segue in terms of what you're doing right now. So we follow your advice. We're scaling quite nicely. We now have a company. We have a terrific market fit. Revenues are coming in, the profits are coming in. We've got a great runway ahead for us.

At this segue for most entrepreneurs, they're just gonna do the same old thing that everyone else does and get the same old results that everyone else does. What's wrong with that narrative? What do you want us to know and how do you fit into that picture?

Alessandro Chesser: Yeah. So what's wrong with the narrative of doing exactly what everybody else is doing? I think that if you want to be a truly great company, you have to think different. there's no one size fits all playbook for scaling a company. I think people like, there's a lot of like business coaches out there.

Here's what you do. Here's exactly what, here's the steps you take. But every company is different, every market is different, every competitor is different, and so you really need to look at things from an individual company perspective and like who your competitors are.

And I think that [00:12:00] trap that a lot of people fall into as you're scaling is they hire super experienced people who come in and they have a playbook. And from my experience, like oftentimes somebody comes in and they use the playbook from outside and like it ends up not working.

It's like really you have to create a brand new playbook specifically for your company. And so you can't really look at things uniformly and think one size fits all approach to building companies. And so I think that's like a huge mistake that a lot of companies take. And we took it, we did it at Carta, we hired all these experienced people and they came in with their playbooks and their playbooks all failed.

You have to take a more custom approach to the company that you're building and the market that you're operating and the competitors that you have. You have to figure things out, like piece by piece. There's definitely is not a one size fits all to, to building a company.

Jeffrey Feldberg: Of that goes back to culture, which we're all about in our nine-step roadmap. Step number two X-Factors. When we have a rich, vibrant, thriving culture, it's really a competitive advantage out in the marketplace. And so with that said, we're gonna put some of the growth tactics and the scaling [00:13:00] tactics aside for just a minute.

Talk to us about what you're doing now on the financial side and with trust and what we don't know that we really should know.

Alessandro Chesser: So qualified small business stock or QSPS is the greatest tax exemption. That exists. It's for C Corp shareholders. it has to be more of like a technology company than a services. If your revenue's 100% services, like you're not gonna qualify for QSPS. So the goal of QSPS, it's a tax exemption that exists that allows you to sell 10 to $15 million of shares in a C corp and pay zero.

Taxes. Literally the greatest tax exemption that exists. Like where else can you sell $15 million worth of shares and pay zero taxes on capital gains, like where there's nowhere else you can do that. The objective of this tax exemption is to incentivize investors to invest in startup companies. That was the whole purpose.

It was like 1991 and. The laws were [00:14:00] created that allow investors to invest in startup companies and pay zero taxes on 10 to $15 million in capital gains. And the idea was to get more investors to invest in startup companies, create more startup companies, create more jobs for employees, have more successful outcomes, and reinvest that money back into the ecosystem.

Creating more startup companies. This really worked, I mean, the US is the leader. Globally when it comes to startup companies. And a lot of that has to do with the tax incentives that exist, that create more startups. By having more investors that wanna invest in startups is huge. And so if you're not familiar with QSPS, I suggest you look into it.

Make sure your startup qualifies for a lot of, like I said, if you're an early stage startup company and you're technology company, a lot of your revenue is more on the, software or technology side. like if you're selling something online, there's a good chance you're gonna qualify for QSPS and the criteria is though that you it has to be C corp.

You have to hold the shares for at least five years. To get the tax exemption and you have to acquire the shares, which all startup [00:15:00] founders are gonna qualify for this, but you have to acquire the shares before the company has $50 million in assets. So all the early employees, if you're raising capital, the second you have more than $50 million in assets, those the employees after that will not qualify and the investors after that will not qualify.

But all the early, it's really there to incentivize early investors or early employees. But for those that do qualify, it's 10, $10 million. For any shares that were issued before July 4th of this year, July 4th is the big beautiful bill date. And any company after July 4th, any shares issued after July 4th.

So if you're gonna start a C corp, it's a great time to do it because you're automatically gonna get, this is changed from $10 million exemption to $15 million exemption. So the first $15 million will be 100% tax rate if you hold the shares for five years. And so it's something that I think a lot of founders are not really familiar with.

And the way I learned about it was in the early days of Carta one of our employees actually, who came from [00:16:00] PWC, told us about it I never heard of it before and I'd been in the startup space for a while and I was like, really? You can pay real taxes on $10 million in gains and. But for employees, you can't actually qualify for that holding period, the five years unless you exercise your share.

You have to hold the shares for five years, so you have to exercise early. any employees that work for startup companies make sure you look into this and make sure you. Do an analysis on, how much it's gonna cost you to exercise and if you're bullish on the company, like you should definitely do it if you can qualify for QSPS.

'cause otherwise you're gonna lose close ha to half your money in taxes if you don't. what my company get dynasty.com does is we help people actually multiply their QSPS benefit by creating trust for family members. So you get the $10 million exemption. In your name, but if you create trust for your two kids and your wife, for example, each trust will get its own QSBS exemption.

So three trusts [00:17:00] will give your family an additional. $30 million in tax free capital gains. So you know, three trust times 10 million each. $30 million in tax free capital gain eligibility, and plus the 10 million that you already have in your name, that means $40 million, 100% tax free, like literally the greatest tax exemption that exists.

Jeffrey Feldberg: Okay, so let's walk this back. There's a lot there. It all sounds exciting. So QSBS, the qualified small business stock, and what I'm hearing you say is when we have A-Q-S-B-S, we can do this special tax exemption where when we've held it for five years, a hundred percent of the capital gains, there's zero tax on it.

As long as we can meet some certain criteria. Now I'm familiar with a C Corp and an LLC and all the other types of statuses for companies. It sounds like an only a C Corp from what you're saying is gonna qualify for someone in Deep both Nation who's not even sure what kind of company they have. So what's a C Corp?

What's the difference between a C Corp and an S-Corp and an LLC [00:18:00] and what should they know about this?

Alessandro Chesser: Yeah, so LLCs and S Corps are typically taxed as a pass. Through entity. So the taxes can be passed through to the individual. The individual is not necessarily an employee, but more of a member of this passed through entity. And so like you, if you were working with an LLC, you would pay taxes yourself.

You'd be 10 99 and you wouldn't have a W2 C corp, your taxes as a corporation. So the company is, not passing through the taxes directly to the individual. So the company would be paying taxes first, then passing the income to the employees as W2 income, and then the employees will pay their own separate taxes.

So if, usually if you have like a cashflow positive business, it is better to do an LLC or, an S corp. 'Cause you can pass through the data, you're going to not get double taxed. And so you can be more tax efficient, but if your goal is to sell the company or you know, IPO, or, you know, raise venture capital for [00:19:00] example.

You definitely want to be a C corp. And I think if you're gonna raise venture capital, then your plan is usually to Exit. It's either gonna be to Exit to, selling the company or to go public. And so if, if you're optimizing for Exit, then like, yeah, do a C corp and like then optimize for QSPS 'cause you can, get all these millions of dollars in tax free gains.

But if you're a goal, on the other hand, is just to operate a profitable business forever and never Exit. Then, you know, you're better off doing one of these past three entities like an LLC or an S-corp. we're not a CP, I'm not gonna give any tax advice here. I would say talk to your CPA and get confirmation on all this.

But typically that's how it works. If it's a cashflow positive business that you never intend to sell better to be an LLC or an S-corp. And if it's the opposite and you're, either looking to raise venture capital or you're looking to sell it in the future, then like C Corp is probably gonna be better.

Jeffrey Feldberg: Okay. And Nation, as we just heard, this is not financial advice. This is. As Alessandro myself, were just sharing some thoughts, some stories with each other. Always check with your proper advisors in [00:20:00] terms of what you should be doing on the financial side, but you made an important distinction, and what I heard was if I don't plan to have some kind of an Exit, perhaps it's going public.

Perhaps it's getting some investment in the company, selling some of the company, all of the company. If that's not the plan, if I'm gonna have a generational family business going on here. Then what we're talking about, the QSBS isn't where I want to be, but if I know, yeah, at one point I am gonna be exiting the company, then having the company as a C corp and looking into the QSBS in terms of qualifying for that and getting all that set up, that's where I want to be because there's some tremendous upsides that are there for me.

So it's a great segue, Alessandro, in, in terms of what you're doing now at Dynasty, so where do you play a role in that? When do you start and when do you enter the process, and then what happens from there? Why don't you walk us through that.

Alessandro Chesser: Yeah, so when you start planning from it, from day one. You know, you're gonna start a company. What type of company are you gonna build? Is this gonna be optimized for acquisition? Is this gonna be, you're gonna raise capital? [00:21:00] Or are you just gonna build a cash flow laundromat for example. And like the type of business is very important 'cause it needs to be like more of a technology company in order to qualify for QSPS regardless.

So, first thing to look at is like the type of company you're building and whether it's gonna qualify for QSPS, if it does qualify for QSPS and your goal is to Exit. Then, you really should be structuring as a C corp right outta the gate so you can start the clock for that five year holding period.

The problem is you know, some people are like, oh, I'll just start as an LLC, and then if I end up, thinking later down the line, I'm gonna sell it, I'll convert it to C corp. But then once you convert it, now the five year clock starts. I have a lot of people in that situation where they're in LLC right now and like, they're like, oh, I'm gonna sell my company.

I wanna get QSPS. It's like, well now you're gonna have to wait five years. with the new rules, there's a little bit of flexibility on that five years. Now you can sell it at the three year mark and get 50% of the QSPS exclusion or sell it at the four year Merck and get 75%. Of the exclusion, but you still have to wait three years minimum just to get 50%.

So I would say you wanna do [00:22:00] that planning day one. Like when you're starting your company. Is your company gonna be eligible for QSPS based on the type of company it is? Yes or no? If it is, then how do you wanna structure your company? Do you wanna optimize for Exit or do you wanna optimize just for cash flow positive?

Own it forever. And I think making those decisions on day one because otherwise it's gonna be very hard to switch around later.

Jeffrey Feldberg: Okay, so some terrific Advisor, nation. Like anything else, hey, know where you wanna be and if yes, I'm gonna be doing an Exit, this is where I want to be, then it's cleaner. It's more efficient time-wise, money-wise, to actually start off as a C corporation as opposed to trying to change things up a little bit later on.

And it sounds like there's some other implications that are going on and it can be time consuming, more complex. And Alessandro, going back to something that you said. So if I'm a manufacturing company. Based on what you're saying, it sounds like this may not be eligible for me. It's only for technology kinds of companies, service types of companies who would, yes, this is a perfect fit, so who would be a [00:23:00] perfect fit for this?

And hey, you know what, you're there. Sorry, it's not a fit. It's not allowed under the program. What does that looking like?

Alessandro Chesser: I would say like the perfect fits are like, yeah, your traditional. Software company, selling software as a service or your traditional, like e-commerce company, like selling products up through the internet are a great fit. Usually venture funded startups, like I would say 95%, 99% are gonna qualify.

But for those that are like more regulated industries, let's say you're a lender and you maybe you're using a little bit of technology, but most of your revenue is tied to just straight like services. Then you're probably not gonna qualify. You wanna talk to a lawyer, regardless and ask 'em.

'cause there is a little bit of gray area. It's not black and white, like there's a little bit of gray area. But I would say like traditional, like non venture funded businesses. If it's a technology company, that's the distinction. Are you a services company or are you a technology company?

If you're more of a technology company, then like, and you're not in a regulated industry, like odds are, you're probably gonna qualify.

Jeffrey Feldberg: Got it. Okay. And Alessandra, I know one of the things that you're doing at Dynasty, [00:24:00] and when I was doing some of the background, I really liked what I was reading about this and learning about this. You want to, if I can use the word democratize, trust. And you want to take trust out there so that the typical entrepreneur who's eligible one knows about it and two can benefit from that.

So talk to us about that. Did you just wake up one day and say, Hey, I'm gonna be doing this, or where did that light bulb moment come for you? What led to that?

Alessandro Chesser: So the Nevada Trust Company specifically, during our time at Carta, we saw that we saw all these cap tables, that's what Carta is, cap table management platform for startups. And so we saw all the, Cartas got a monopoly like. Close to Monopoly, like 70% I think of startups are on Cardus platform, pre IPO startups.

And so when you look at these start and we did all the onboardings, my teams, helped get the Excel based cap tables and move 'em into software. And so we look at all these cap tables and we saw that a very small percentage of founders. Would put their founder shares into like multiple trusts for family members.

And it was like, why are they doing that? Are they [00:25:00] just being super generous? Are they just giving away all their shares? actually learned about it. 'cause one of our investors did this and created a bunch of trusts and sold $40 million and paid zero taxes and told me about it. And so when I heard that, I was like.

That's incredible. Why doesn't everybody do that? And he's oh. 'cause it costs a couple hundred thousand dollars to set it up and it costs like $25,000 a year just to maintain it. I was like it shouldn't cost that much. Like these are templated legal documents, like why can't we need to fix that?

And so that's when we started looking into turning into an actual business and. We left and we, raised capital and we raised $6 million and we went through the process of becoming a Nevada trust company. ' you know, Nevada is like the number one state in the country when it comes to trust.

Like they have all the best rules that allow you to do all these crazy things with trust that, help minimize taxes and help protect assets from everything lawsuits and bankruptcy, creditors, even divorce. And so we knew we were gonna become a Nevada Trust company, and we knew we wanted to democratize Nevada Trust.

For [00:26:00] anybody who wants to use the Nevada trust, why not? Why not let them? If it's a farmer in Oklahoma who wants to protect their farm from lawsuits, why not? Why shouldn't we let them do that? Because the old model, they're not gonna be able to afford it, but with our model, we can make it available to them.

The billionaires do this, why shouldn't everybody else? But as we became a trust company, in the mantra of, building a successful startup and going zero to one, you wanna go really narrow with your first customer profile and create a very solid business and then expand, inch by inch.

the reason why you want to go narrow is because the goal is to create. obsessively happy customers delirious happy customers. That's the right phrase. You wanna make your customers deliriously happy. the only way to do that is to be very specific on who you're selling to and what problem you're solving.

You can get really good at solving that. If you just focus on one problem specifically, you can get very good at solving that one problem and you can create the best experience possible. And so that's, we focused in on startup founders and Qs PS, [00:27:00] stacking, it's one very narrow problem, like Nobody else is doing this, so we're the only player in the market. That's completely full stack licensed Nevada Trust Company doing QSBS stacking for startup founders. It's very narrow. And so it allows us to go and take the market very quickly and acquire a, large amounts of customers every single month and become the defacto solution.

And then once we're the defacto solution, then we expand the market inch by inch. And we go from startup founders to startup investors, and then we go to the limited partners at the venture funds, and then we go to the masses and we help everybody right by inch by inch. Versus if we just try to go to the masses in the very beginning, like there's all types of competition trying to go after the mass market customers.

It's hard to make anybody deliriously happy if I'm like, one guy's putting a farm in the trust, another woman's putting her crypto in the trust. Like how do you, create a deliriously happy customer when you're trying to solve everybody's problem? And everybody has different problems. And so we really focused in on this one problem.

And then the plan is to expand over time.

Jeffrey Feldberg: Okay. My goodness. So there's a lot there. So a few things. Let's go [00:28:00] back to some of the numbers, just to put this in perspective. And you're saying that we do this right, and we're working with you, the dynasty team through QSBS, and again just. Putting some numbers out there, I could have perhaps $40 million in trusts that are gonna be exempted.

So to use round numbers, I have some kind of liquidity event, which is obviously what we're all about here at Deep Wealth. Let's just make the math easy. I have a hundred million dollars liquidity event, so from that a hundred million dollars, which would normally be taxable. What I'm hearing, and you can say, Jeffrey OnBase off base, the a hundred million dollars, less than $40 million, that's exempt.

It's now $60 million. That's the taxable amount and not the a hundred million dollars. How am I doing with that?

Alessandro Chesser: That's exactly right. But you know, one interesting caveat is that. There are examples of people creating 10 plus trusts and getting over a hundred million dollars in tax free capital gains attached to these trusts. And one example is the founder of roblox. You can read about it in the New York Times Roblox founder QSPS.

You'll see it. They created 12 trusts and got $120 [00:29:00] million in tax free capital gains. So, that's the, that's why it's called trust stacking. You stack a bunch of trusts and they each get QSPS exemptions.

Jeffrey Feldberg: And so there's always gonna be outliers there and perhaps that's the way to go. Perhaps that's not, but Alessandro, you, the dynasty team, it sounds like you're gonna just be helping me go through that. So that's what's going on there. However many trusts I have that are QSBS under that umbrella.

That's what I'm subtracting from the net amount from my liquidity event that's gonna be taken out of the mix and whatever's left over, that's where I'm getting taxed on. So that's significant savings that we're talking about. And then the other thing that I heard you say, and I love it as an entrepreneur, you're going out there, you're solving a problem.

Up until you covered this problem, you found out about this problem, you asked the right questions. Why is it so complex? Why is it so expensive? And it sounds like with Dynasty, you and the team, you're now simplifying that process and you're taking the high cost out of it, and you've been focusing on entrepreneurship down the road, maybe you'll do something else and [00:30:00] expand that into other areas of the market.

But right now, for founders, for entrepreneurs who know they're gonna have some kind of liquidity event, again, going public, selling part of the company, all of the company. You are there with the QSBS trust services to sign me up and get me going in that direction. So what's some of the secret sauce when I'm working with you and the dynasty team?

What's going on with that? What would that look like time-wise and approximate cost? Not down to the penny, but just very high level. What's that looking like?

Alessandro Chesser: Yeah, so we charge $1,500 a year for four trusts. And that covers trust creation trust administration, and annual tax filing. So, super, it's like 5% of the traditional costs of doing this. We can be so much cheaper because we only do this, we only work with founders. We only work with QSBS, stacking stock like founder shares.

And so we're not gonna help you with your farm, we're not gonna help you with your crypto, we're not gonna help you with your home. And so we're very specific. So allows us to create this like full stack. Product where everything is automated and it's like a factory. A factory for [00:31:00] one specific problem, right?

And we've solved that problem very effectively. the old model is this will take you three to four months to complete with the, you have to work with the lawyer. They're putting all this customization into your trust. They're helping you with all your other assets as well, and they're looking at the full picture.

They're doing all your, you know, then they added in a CPA for the tax planning and then when, once you're done creating the trust and you work with the trust company to do the actual trust administration and then they help you file a tax returns too. And so by the time you're done with this three, four months and you're working with the trust company that's charging you.

10, 20, $30,000 a year for the administration. 'cause they're doing everything manually. They're using fax machines, they're using filing cabinets where we are a complete like venture backed technology company. And we automated trust creation, we've automated trust administration, we've automated the filing of the tax returns 'cause we only do it for this specific use case.

And so that's how we're able to be significantly more cost effective and. We can get these trust done in a matter of day. Our fastest is three [00:32:00] days and we're trying to get it done in two days, like next week. And so, like, eventually we're gonna get it done in one day for a customer. And that's lightning compared to the old model of doing this.

Jeffrey Feldberg: And so what I'm hearing you say, Alessandro is. You're taking your background before you started Dynasty all of your entrepreneurial experience, and you are now putting your focus and your energy into this. Because what you're saying is, Hey, I am not gonna be all things to all people. So if you wanna do your home and other kinds of assets, I'm probably not the company.

We aren't the company for you. But if you have a company. That fits this specific criteria and you fit within our system. Then for $1,500 a year, you'll have four trusts, and behind the scenes we're automating everything. You're not gonna have to go from one Advisor to the next Advisor and have to find out, okay, who's the tax specialist or who's the trust specialist, and where am I gonna be going for this or that?

It's a one size or a one stop shop. Which is Dynasty. You've done all this in the background. I'm making an assumption here, and you'll clarify. Of [00:33:00] course, behind the scenes in terms of the regulations and any changes and whatever needs to be done. You're tracking all that for me. So I simply show up, sign the property documentation, pay your service fee, and then behind the scenes you're doing everything else.

So I'm saving time, I'm saving money and effort so I can go back. Build my business, scale it, take it to a terrific level, and actually appreciate what you're helping me do on the backend. When it comes time for my liquidity event, I'm gonna have hopefully lower taxes by the sounds of it. How am I doing with that?

Alessandro Chesser: That's exactly right. You know, You're gonna work with us. We're going to, you know, it's really a white glove like onboarding process. We don't put a lot of work on your plate. We get on a couple phone calls with you. We extract everything we need. We automate it on our end. we do have add-on packages for those that want to add on an attorney or add on a cpa like we have, like law firm and CPA firm partner that we work with.

You pay a few thousand dollars extra, you end up with the CPA or lawyer add-on. that feels a little bit closer to like the traditional process. Obviously it slows things down. But for those that. You don't want extra [00:34:00] assurance and, don't want to just work with the startup company by themselves.

Like I would say 95% of our customers don't do that. 95% just sign up and, you know, use our product like out of the box as is. But for those that want the more sophisticated type planning, like we have the resources to do it.

Jeffrey Feldberg: Okay, so what I'm hearing you say is, Hey, we have a one and done over here, but Jeffrey, you wanna get a little fancy, you want to customize. Okay. I can't give you the quicker turnaround time or the lower service fees, but I can accommodate you and we have the ability to do that. And so Alessandro, I'm thinking now from a listener in Default Nation and they're listening in to our fireside chat, just you and I here, and they're saying, okay, let me get this straight.

I can get this trust and up to four trusts with the dynasty and team, and I'm saving up to $40 million. Hey, it sounds too good to be true. What's the catch? Are there any catches here?

Alessandro Chesser: So the important thing to know is that these aren't your trusts. You're setting up trust funds for these beneficiaries, whether it's your children or your parents, your siblings, your spouse, whoever. It's their money, [00:35:00] not your money. So you can't look at it from the perspective of oh, this is all my tax free money.

No, you the only. Reason why the tax savings are coming is 'cause you're spreading out your shares to people that are not owners in your company. Now they're becoming owners and so they get their own QSBS eligibility, for example, like me giving my shares to my brother directly, he would have complete control of those shares and he could go spend the money on whatever he wants after we.

It versus when I put it in a trust, there's a little bit more control in place of like how that money can be reinvested and what the distributions can be used for. And so me as the trust creator, I can have some level of influence in the trust and how the funds are invested. If I want the trust to invest in real estate, the trust will buy real estate.

If I want the trust to invest in startups, those trust will invest in startups. so it's like you have to look at it as like a trust fund that you can control. It's more like an investment account. You can look at it as your personal piggy bank. You have to look at it as like, these are an investment account.

Trust funds for your beneficiaries. It's their money. It's [00:36:00] not your money. The IRS would never let you maximize QSPS for your own individual purposes. It has to be for other people.

Jeffrey Feldberg: Okay. Some terrific insights there and so de Both Nation, if you are planning on having your children or spouse or family members at one point in time, have them be the beneficiary or benefit financially. This is definitely one way to go, but de both nation, we just heard it straight from the source. If you're saying, Hey, I can get these four trusts and it's $40 million I can play with down the road.

It's not taxable, not happening. Uncle Sam is not gonna let you do that. It has to be for specific beneficiaries. Now, Alessandro, is there a time limit to this trust? Do they expire at one point in time that you then have to do something, or is that infinitum? How does that work?

Alessandro Chesser: No, these are Nevada dynasty trusts. That's another benefit of using Nevada Trust, is these trusts can live for 360. Five years. So the whole purpose is like to create multi-generational Wealth planning. They go to your children and then they go to their children and then their children. And it's a [00:37:00] fortress that's excluded from estate taxes for 300.

It never has to pay that 40% estate tax for 365 years. And while the assets are held in these trusts, they're protected from everything, as I mentioned, like lawsuits, creditors. If anybody gets divorced, whether it's the grantor or the beneficiaries, it doesn't matter. These trusts are excluded from their estate, so they're not gonna be.

At risk of a divorce. So if you're passing money to your children and you're worried that they're gonna get married and then get divorced and lose half your money, you don't have to worry about that anymore. Like, These trusts are gonna create that infrastructure, that fortress to provide for multiple generations and make sure that there's like money left over.

And so that's the purpose of them. It's not. These, the, usually the distributions are limited, like for cost of living, housing, healthcare, education, transportation. Usually the money in these trust is not gonna be used for, cannot be used for. Frivolous spending, gambling, whatever, like vacations, like sports cars, like usually the purpose is to provide like a minimum standard of living for like multiple [00:38:00] generations.

And so because they can exist for 365 years, it just really creates a lot of flexibility on the planning side.

Jeffrey Feldberg: Has some terrific news here in terms of what you're doing, and if we flip the script for just a second, because here you are, you're a startup. You found an inefficient marketplace. You went out, you got some investment, and you now have this company that's out there that's making it more efficient. It's making it more accessible.

So from one entrepreneur to another, what's that been like? Because it sounds like you're going up against some very established, well-funded, multi gazillion dollar companies. You're the new kid on the block. How's it been for you?

Alessandro Chesser: I think all the lawyers like pushed back against us. You can't do this, you know, and I'm like, we've already done over a hundred customers in 90 days, and we work with the largest sustained planning firm in the country as a partner anyways. So. I think that there's always gonna be the incumbents and we're not going after their business though.

Like I'm not going after the customers that are gonna go pay a hundred thousand dollars to set up trust, like they can go do that. Like we're not going after that. We're going after the early. The best time to set these [00:39:00] trusts up is day one. When you start your company, because there's gift tax implications, the best time to do it is when the shares are worth zero.

'cause there's no gift tax. The longer you wait, the more the shares go up in value, the more gift tax implications you're going to have. So like that's the problem we're trying to solve. We're trying to make it possible for a startup founder to do this from day one, but founders from day one can't afford a hundred thousand dollars to create this.

So like we're expanding the market and going after a new customer that wouldn't do this otherwise. So that's my argument to them is we're not going after your customers. We're creating a new group of customers. But with that said, like they're always gonna look at us as threatening, and that's the nature of the business.

Like we're a venture-funded startup and they are not. And we're very different.

Jeffrey Feldberg: Yeah, it's so interesting and to your. Point for someone who's a founder, even if they knew about this, which they probably don't, even if they wanted to do this because yeah, hey, it sounds great. I don't have the time. I don't have the money. This is way too complex not happening. So dynasty, you and the team, you're coming on board here.

Hey Jeffrey. We can have it done within [00:40:00] days for you go focus on your business, but we have you covered. And Alessandra, you're exactly right. When I have a clean slate, I'm starting with zero. And I put these trusts in place that's the most tax efficient, that is the best way to do it, and is not taking away from my next marketing campaign or my next hire, which we're talking about earlier, because let's face it, $1,500 a year.

It's relatively inexpensive. It's a rounding error compared to the savings. And then on the flip side. There's a 365 year limit, you're telling me on the trust. For all intents and purposes, it might as well be forever because obviously, sadly none of us will be around for that, but we're protecting the family or whoever the beneficiaries are.

They have something that protects 'em, whether they get married and that marriage doesn't work out, there's all kinds of protection in it for them. So talk about the gift that keeps on giving for the beneficiaries where I have the foresight to be able to do this for them. Wow. It's a complete game changer.

And Alessandra, when it comes to liquidity events now, and I have these trusts that [00:41:00] are in place, does it interfere or make it more complex when I have a buyer coming in and saying, oh my goodness, you have all these QSBS trusts going on here. Uh, No. Go Jeffrey. We don't wanna go down that path. Any issues there?

Or it's part of the course.

Alessandro Chesser: Yeah, I'll start with the second question, which is related to, yeah. Investors coming in and taking a look at the cap table and seeing if there's all these trust, like they're very familiar with it. The most successful investors and founders do this and they know that. the founder's still gonna retain the voting rights for the shares, and that's usually what they care about.

But other than that this is estate planning. Estate planning is a, it's for the richest Americans too. Like we're not doing anything below board, like you said in the very beginning. It's above board. These are very. Wellknown strategies that the most successful Americas use. And so we wanna make it available for everybody.

And so if anybody were to push back, you just point to all those public examples oh, how come they can do this? Like, why aren't you, you know, it doesn't make sense for to stop anybody from doing it. The investors use this. They're not gonna stop the founder from doing it. And then your first question, [00:42:00] what does this look like for the beneficiaries?

I mean, this is. We are democratizing trust funds. That's really what this can say. Multi-generational trust funds. Most Americans don't have a trust fund and people think that you need millions of dollars to create a trust fund now. Now, if you have a company, you can create that trust fund from day one, you can put 10% of your shares into these trust funds.

And if the company ends up working out really well, you got a lot of tax savings, but you have this like multi-generational structure that can provide for your family for 365 years. And so, democratizing trust funds, like it's never too early to create that trust. Like if you can afford 1500 per year for up to four, like. do it. And you know, a worst case scenario is like your company doesn't make it and it goes outta business. Like you don't have to pay for the trust funds anymore, and like you haven't risked, the only risk is at 1500 per year. Maybe a few years goes by, the company goes outta business, you've lost 4,500.

But if it does work, you know your fixed cost is like 1500 a year, but if it does work, you get millions of dollars in tax free capital gains. Like it's enormous upside potential. And [00:43:00] so, I think for those that have children, that have spouse, even if you don't, the ability to plan for like future children and create these trust funds in a tax efficient manner, like it didn't exist before.

Jeffrey Feldberg: As we're talking about this, to me, it's like insurance. If we look to, I'm gonna insure my house and I insure my house year after year. I've never used it. But I've still insured my household. Same kind of thing with this, Hey, I'm going to ensure the future for whoever the beneficiaries are. And as we enter the golden era here as Americans going down this path for Wealth accumulation, Wealth preservation, this is one terrific way of doing it, completely above board.

It's been for the elite up to this point. You're democratizing trust to get this out there to every entrepreneur who wants it. You've made it accessible. It's incredibly affordable. And it's easy. It's quick. It doesn't get any better with that. So, deep Default Nation, you've heard something that you probably haven't heard before and it's something that you should look into.

And Alessandra, before we go into our wrap up mode, [00:44:00] as I'm looking at the time here and I'm looking at my list of questions, which I've barely begun to get through, is there a question I haven't yet asked or even a theme, a topic or a message that you wanna get out to see about Nation before we go into the wrap mode?

Alessandro Chesser: Yeah, I think the most important thing is like the, and you mentioned it. Earlier, like the planning, the earlier the better. The more taxes you, the earlier you set this up, the more taxes you can save. The longer you wait, the more gift tax implications and the more restricted you're gonna be from being able to create trust and get assets out of your name.

Estate planning works well when you have high appreciating assets, but you give 'em out of, gift them to the trust before the trust go up in value.

Jeffrey Feldberg: Absolutely love preparation, as we say here at Deep Wealth and with a nine-step roadmap. Preparation, when it's done well is the gift that keeps on giving the time, the effort, even the small investment that goes into it. The ROI, it's a rounding error relative to what you're getting from doing that. So absolutely love that.

So that said, Alessandro, we're gonna go into wrap up mode and it's a tradition here in the Deep podcast. It's my privilege, my honor, where every single guest I ask the [00:45:00] same question. It's a really fun question. Lemme set this up for you. When you think of the movie Back to the Future, you have that wonderful and magical DeLorean car that can take you to any point in time.

So imagine now it's tomorrow morning. This is the fun part. You look outside your window and not only is the DeLorean car there, it's curbside. The door is open, it is waiting for you to hop in what you do, you're now gonna go back to any point in your life, Alessandra, as a young child, a teenager, whatever point in time it would be.

What would you tell your younger self in terms of life lessons, life wisdom, or, Hey Alessandro, do this, but don't do that. What would that sound like?

Alessandro Chesser: I think that, the most important thing for me is, I would say for me personally, like I waited a long time to take the leap into entrepreneurship. I waited until I had a successful outcome at my last startup company. I waited until I got married and had kids. I don't know why I did that.

I started a company, I should have done it before. I think like the earlier the better. [00:46:00] that's my biggest regret is like kind of did the opposite. I waited until I had a lot of responsibilities, and then I started a company. I would say, doing it when you, before you have all the responsibilities of children and whatnot that's when you can take the risk.

That's when it makes more sense. And so that, to me, it was just, hindsight's 2020. But you know, going back in time, I would've probably taken the leap and started a company a lot sooner.

Jeffrey Feldberg: Well, Alessandro is saying, goes better late than never, and you did it. So congratulations to you on that. And it's also great advice, Hey, don't wait to start your entrepreneurial journey. It's actually going back to how we began the conversation where you shared when it comes to hiring. Just do it.

Don't overanalyze and see how it goes. You can always change course, and if it works out, great. If it doesn't, that's okay too. At least you're out there and you're doing it. One of my sayings is Dreamers dream doers do. And if you look out there at the successful people, it wasn't perfect. They just started.

They went out there, they did it. The dreamer, we all know who these people are. They tell us their [00:47:00] dreams and how big it's gonna be. But nothing happens is just talk. It's like writing on the sand. It's there one second. Gone the next. So it's some terrific advice. And let me ask you this, someone in Deep Nation, Alessandro, they have a question for you or the team.

They even want to sign up and get things going. Where would be the best place online that someone could reach you?

Alessandro Chesser: LinkedIn's probably the best. Alessandro Chester. You can find me on LinkedIn or you can find me on Twitter. Com That would be the best ways to get ahold of me.

Jeffrey Feldberg: Nation doesn't get any easier. Go to the show notes. All of Alessandro's contact information, all the sites, it's all there. It's a point and click. Well, it's official. Alessandro, congratulations, as we like to say here at Deep Wealth. It's a wrap. May you continue to thrive and prosper while you remain healthy and safe.

Thank you so much.

Alessandro Chesser: Thanks for having me. 

Jeffrey Feldberg: So there you have it, Deep Wealth Nation. What did you think? 

So with all that said and as we wrap it up, I have another question for you.

Actually, it's more of a personal favor. 

Did you find this episode helpful? 

Have you found other episodes of the Deep Wealth Podcast empowering and a game changer for your journey? 

And if you said yes, and I [00:48:00] really hope you did, I have a small but really meaningful way that you can actually help us out and keep these episodes coming to you.

Are you ready for it? 

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God bless.