Navigating Early Pivots - Adam Dell - Domain Money - Episode #50

We're in an existential fight to prove that we have the right to exist and that that requires an enormous level of commitment and passion and willingness to bear uncertainty and risk.

Welcome to Not Another CEO Podcast. I'm your host, David Politis. Every week we talk to inspiring leaders and get the true stories, the ups and downs, the lessons learned, and come away with actionable advice for our own journeys. Today's guest is a serial entrepreneur, investor and operator who has spent the last 20 plus years at the forefront of technology. He has founded and led Multiple companies, including Buzzsaw.com, which was acquired by Autodesk in 2002. Message One, acquired by Dell Technologies in 2008. Clarity Money, acquired by Goldman Sachs in 2018. His latest venture, Domain Money, is an AI powered personal finance and investment platform designed to help individuals build wealth. They do it by democratizing access to financial expertise. He's someone who I've learned from over the years. Honestly, every conversation I've had with him, he teaches me something new, something that sticks with me. So I'm really excited to have here today. Adam Dell, founder and CEO of Domain Money.

Thanks for having me, David.

I'm very excited. First question right out of the gate. So what is the one thing you've done at Domain Money and your other companies, big or small, that's had the biggest impact and you'll do again if you're CEO of another company in the future?

Yeah, that's a good question. I think the most impactful thing that I do that might be different than a lot of CEOs is that I recruit myself right out of LinkedIn. It is the most powerful tool I have found to get to individuals directly. And I'm a little bit unique, particularly in the New York tech scene, in that I've been in and around financial services for, you know, a decade now. And if you're in financial services, if you're in technology, the convergence of those two things. You've probably heard of some of my work. And so I have a bit of an advantage, a competitive advantage among all the recruiters who are scouring LinkedIn. If you get an email from me on LinkedIn, it is in fact from me and I am, in fact reaching out to you and I have found that my hit rate is pretty high. And while it's very time consuming, it's really effective for recruiting great teams, which, as you know, is the core of success of any startup.

So you said it's time consuming. I have done it before. It is very time consuming. Like how much time will you spend on it? Like, hours a day, hours a week? Like, what, what is, how much time will you actually spend doing this?

Yeah, I'll spend hours a day on it. And I have a system that's pretty refined at this point, by the way. I have some help, I have my assistant who will help me. But, you know, let's say we're hiring for a particular role, a product marketing function. You know, I'll identify a list of, you know, five to 10 companies that I think there is, you know, talent in that is, you know, relevant to the experience set that I'm looking for. We'll define the years of experience, we'll define the titles, and we'll use those filters within LinkedIn to identify a set of candidates that we'll reach out to. And then I'll send a message. You know, some percentage of those people get back to me and those filters of somebody responded, okay, they're interested or they're curious. We have a series of filters that we use to try to weed out who's ready for and interested in a startup. Who has the requisite experience set and does that meet with the needs that we have as a company.

Do you how when you do an intro call, like, I'm going to just guess based on knowing you, probably a lot of people may just respond, maybe just to talk to you, you know what I'm saying? Like, do you do a five minute, like, do you have some, like, set time so you don't spend hours, you know, talking to people who are not really serious or you, you talk to them for half an hour.

I mean, we try to weed out the people who are just in it for a meeting. There are some people who are gracious enough to be honest about it. And hey, I'm not interested in moving, but I, you know, I did want to take the meeting, you know, because I want to network with you or whatever. And I try to, you know, be polite and give them some time, but maybe not the full 30 minutes. I try to be respectful of people's time and hope that they're respectful of mine. It is enormously time consuming, but it is also ultimately a great way to, as I said, get to great talent. I'm not a huge fan of using recruiter because they essentially do the same thing, but with much less effectiveness because they don't have the depth of understanding of exactly the skill set you're looking for. You know, I sort of know, I sort of know it when I see it. I've done enough Recruiting and enough hiring that for any given role. I kind of know what I'm looking for.

I, I think this is, so this is actually the, you're the first person to say this as this answer. I think I've interviewed 50 people now and you're the first person. But it's, it's something that, having done it before but not as consistently as you and not as aggressively. Like I, I know you hired someone who used to work with me and, and you reached out and you pinged me and you checked on them and then you said can you, you know, and, and, but it's such, it's really good advice because I think even if you're not a super successful person, multi time CEO, there is something when it comes from CEO, from founder, like there's something that when someone like that reaches out because it's different than 90% of the other companies or 95% of the other companies, you will get responses. And I, I would actually say, I think it's even past just recruiting it, it's actually for any, it's for sales, it's for, you know, partnerships. Like if you actually, you are the one reaching out, it cuts through noise because people say, wow, that's how important this role is. Or I would be as a partner, like the founder is reaching out like that. So I think that's really, that's really good advice.

Yeah, it's worked really well for us.

Have you ever do do. Is there a stage that you give that you stop doing that or like you do that regardless of stage of the company?

No, you can't do it forever. But in the early stages of a business, you know, call the first 50 to 100 people you can do it, but you know, you can't do it past, excuse me, you can't do it past 300 people. Something like that.

Okay, I want to talk a little bit. You know, so this is you. I have many companies you've had. It's hard to, it's hard to keep count, but many of them and in this one you've raised, I'd say a significant amount of money, you know, kind of early on to build this business. Is that process as easy as people maybe assume it is, given your track record? Like is that something you just call the people who you invested, who invested in you before and you kind of of raise the money? Is that, is that what that process is like?

I've been really fortunate to have a consistent set of backers with my startups. And you know, when the markets are Frothy and people are excited and you hit them with something that speaks to what they are looking for. It is a pretty straightforward fundraising process, particularly given that I've done this a couple of times. But of course, you know, when markets are more tumultuous and people are less bold, fundraising can be challenging. I was able to raise the money for domain money quite quickly. It was sort of as you described. I sent out a deck to a few of my prior investors, told them what I was doing and pretty quickly got term sheets and commitments. That's not always the case and I certainly don't believe that that's always going to be the case. Right. You kind of have to prove yourself each time. It is amazing to me how much is dependent on the psychology of the investor community at any moment in time.

Can you talk a little bit? I. So that, that is, that's the advice I tell people all the time is like, you know, it is because, because I get people who tell me, oh, but that company just raised this much and they do the same thing. I'm like, but, but they raised it two years ago. And two years ago it's like that's, you know, different, different time and maybe can, like, how does that. Because you've also been an investor. I mean, you've been, you know, you're at Austin Ventures and you've been an investor. You've had some very successful investments. How does that happen? I don't know how to ask that question. Like, how does that, that, that. It's like everyone just goes in the same once, once one people, one group starts to get nervous and everything. It feels like it's just this trickle down that everyone starts to follow that and then vice versa. Like where does that come from, do you think?

Well, herd mentality is a real thing. Sentiment in the market is a real thing. The psychology of the investor, the psych consumer. There are, you know, whole courses taught at the University of Chicago about the impact of psychology on the markets and on consumer confidence and the measure of all those things. That is a very real dynamic and it exists even within the intelligent community of the venture capital industry that purports to be contrarian thinkers and going against the, the, the trend or tide, you know, if you want to be right, you can't be, you know, conventional in your thinking all the time. But you know, psychology is a powerful thing. And when people see their stock portfolios down and they see their portfolio companies struggling because the markets are overall tough, not just the public markets, but you know, when Consumer confidence goes down, people spend less, so consumer businesses don't do as well, so consumer startups suffer and all the things have a cascading effect that that is something that's not that the venture community and the investor community is not immune from. I often think about OpenTable. You know, we went public in 2008 when no one was going public and it was sort of a unique thing for us to do. And in a way we got a lot of attention from the investor community because we were the only company that was brave enough or absurd enough to go public in that environment. And thankfully, given that we were really one of the few companies to go public at all, it ended up serving us well because we got a lot more attention from the investor and community than we otherwise would have got.

Interesting. So one of the things I, I think is, you know, maybe you could just talk a little bit about the evolution of domain money because it's not what you set out to build originally and it feels like it's taken you time to now find what feels like fast moving water. You know, can you maybe just talk about the, the evolution of that?

Yeah, sure. We set out to build a, a crypto bank effectively and discovered pretty early on that the world didn't need that. And part of my thesis was that crypto would become a mainstream asset class, which probably happens at some point, but it's a long way away. And so made the very tough decision to pivot pretty early on. Well before the most recent kind of crypto winter and well before my employees and co workers at the company felt like it was the right time to pull the plug. In fact, the team was quite surprised and shocked that I made such a significant change. But I think in hindsight it's turned out to be a good decision. You know, if you look at the market cap or the relative value of businesses like Coinbase or Robin Hood relative to how much cash they have and what kind of margins they they create, I just don't think that business was worth pursuing and so shifted to what we're doing now, which is financial planning. And to be fair and transparent, it wasn't an easy transition at all. Pivots are hard by nature. This one was particularly hard because candidly, I had a rough idea of what I wanted to try to do within wealth management, but not a precise idea. I knew that there was a real problem with wealth management in that most Americans can't afford a high quality financial advisor. The do it yourself tools out there, many of which I was very familiar with really left a gap in between. You know, you've graduated from do it yourself tools like mint and betterment and having a high yield safety account. Your life is starting to get much more complex. You have another baby on the way. You want to buy a house, you got to save for college. You need to be on track for retirement. You need insurance. You know, all of those pieces need to fit together. And the do it yourself tools kind of fall short when that level of complexity arises. I knew that that dynamic and problem existed, but I didn't know exactly how to crack it. And so it took us a little while to find our way. And we candidly tested a lot of different ideas as we found precision around the value prop. We think now we've gotten it pretty tight. We've served over a thousand clients at Domind Money today. Our client satisfaction rates are really high. And we really do a very unique thing. One is we deliver a very, very personalized financial plan to clients which give them very specific to dos. This is how much money you should put into your 529 account each month to be able to pay for Charlotte's education. She's going to go to college in 12 years. Here's the estimated cost of that. If you contribute this much each month, you'll be on track to pay for her education. We give you very specific to do's in each of the areas of your life that are important. You care about travel, you care about a new home, you care about a new car. We'll build a plan around those goals that fits within your lifestyle, your income, your expenses. What do you have left each month, how do we contribute that to your various goals? And we price it very fairly. You know, you go to a typical wealth advisor and you're looking for, you know, wealth management. They're going to charge you 1% fees on your assets or they'll charge you a flat fee, you know, 10, $15,000 a year. Our services are priced at, you know, 30, $200 a year or $4,800 a year. They're very, very fairly priced and the price goes down over time as the needs you have change. And so we've really tried to price it in a way that speaks to the value and the problem set the clients have. And so we feel pretty dialed into product market fit.

How did you get your. Having been through a pivot myself, pretty big one and, and like how did you get the team to buy in? I mean it is a big, it's a big deal, especially, you know, for you as the founder, it's like it's all in your head. You think about it every night, like you came to this thing, but to them, you're just showing up and telling them like, hey, we're going this completely different direction. How, how did you get the buy in from them?

Yeah, it's, it's hard. You know, it's a lot of communication, it's a lot of back and forth with the team. And candidly, you know, as the founder trying to find product market fit, you know, you've got to convey confidence and optimism at the same time. You need to be transparent and realistic with your team. And I try to be both. I try to tell them, you know, with all honesty, hey, it's on us to figure this out. No one's coming. You know, if we don't figure this out, we die. And here's the things we're trying and we're testing and we're in an experimentation phase and just be clear about that. And I think, you know, people who have the appetite to be in an early stage company, particularly one going through a pivot, they understand that and will bear through a lot of pain and work with you to try to discover the answer to that experiment. But it did require and does require a lot of experimentation. And know we ran into a lot of walls and had a lot of long nights thinking about how to, how to evolve the business. And we still do that. You know, as you know, a startup is an unending series of puzzles to solve and each one gets, has its own unique traits and, and complexities and we're trying to solve them each day. And you know, I tell people that I interview, you know, what are you looking for or what do you expect to happen here? And I tell them that we're in an existential fight to prove that we have the right to exist and that that requires an enormous level of commitment and passion and willingness to bear uncertainty and risk. And that's the truth of it. And if you don't have that appetite, a startup's probably not right for you, especially not one at this stage. And it's not for everybody. I kind of love it. That uncertainty. Clearly, clearly that, that uncertainty that, that thing inside of you that forces you to figure it out is very motivating to me and I quite enjoy it.

I think the thing you said there about I again we talked about this like the people listening to this. Mostly it's early stage founders, first time founders, first time CEOs, executives who want to be CEOs, or founders one day. And I think one of the things you said there is really important is qualifying like making sure you have the right people around the table so that when you show up and say we're going to pivot, of course it's still scary. It's still, you know, there's still the uncertainty. But having the people around the table who you've already pre qualified to make sure that they're, they're in the mindset that this could happen and that they're in the mindset that there is this uncertainty and they're kind of, they embrace that versus are scared of that. You know, I think what, what I see is a lot of times, including myself frankly, early in my career, I would try to convince people to join versus like what you just described is almost convincing them not to join. And the people who still join are the people you want on the team. You know, it's kind of because I think first time founders you're like, no, you're going to come, we're going to be billionaire. Like this is going to be amazing. It's actually you have to do the opposite to make sure that you the right kind of person, at least in the early stage. Right?

Yeah, I absolutely do that. I, I sort of downplay the, the, the excitement and I, I, I really amplify the uncertainty and the risk because I want people to understand what they're getting themselves into and particularly in this current business. Because we have so many of our team members who come from traditional financial services businesses. Right. We have certified financial planners on staff. They serve our clients. We tend to hire from the best banks and financial institutions in the marketplace. Those individuals tend to have come up through corporate America in a more traditional training program. And so they are by definition people who are less but interested in taking on risk. They're not startup folks by their DNA. And so it really requires us to find people who have the financial expertise to deliver high quality financial planning services with a culture of risk taking and experimentation, which is really not part of the ethos of work management as an industry.

How did your investors take the pivot? Like is it, is it, did you just tell them one day we're pivoting and that was kind of, that was it? Or do you go have a conversation with them? Like how did they react to it?

I mean, I gave them some data. I tend to be quite driven by data. You know, emotions don't make skilled workers. And so I presented them with some facts and data and said, here's what I believe the terminal value of this business is at some level of reasonable scale and I didn't think it was worth it. And I told them I wanted to go pursue this wealth management thing and they were very supportive. They certainly asked a lot of probing questions and challenged my thinking, which they're there to do and I appreciate that. But they were quite supportive. And you know, we've, we've, we've, you know, worked hard to find our path but as I, as I mentioned, you know, there's, there's no guarantees in life. This, this remains a startup. And while we've made real progress in the last year and had our best month ever in March, you know, we did nearly 250,000 in bookings in March, which is really good for us as a startup. We're on a good trajectory and you know, feeling really strong about the business and its prospects. You know, it's still an early stage company and we still have a lot to fight for to justify our existence.

As I said, how did you, you mentioned you've served a thousand or you're serving a thousand customers on this new version of the platform. And how did you get the first set of those? I mean, did you call people personally? Did you put on, was it all online marketing, you know, kind of demand growth marketing? How did you get that first set on the new platform?

Yeah, well, one thing we did was we, we acquired a very small RIA that had served us a reasonable number of customers and we relied on that model of referral and lead generation to begin with. And then we started to do all the things you would expect. We had a referral program, we had some organic content, we did some paid social, we started to know, try to drive our, our SEO and SEM efforts. And so all the things that you do as a growth hack strategy to get early clients, we did. One of the most successful things we did was we partnered with a woman named Katie Gotti who has a, a platform called Money. With Katie, it's a very robust, vibrant community of people who are interested in understanding how to empower themselves in their financial lives, think about money in from a place of abundance and really not be subject to the, the bad deal offered by traditional banks or some of the competitors of the market who charge 1% AUM fees. The ethos of that empowerment and you know, taking charge of your life and being in command of your financial future. Does ethos really align with ours domain Money and in our partnership with Katie Gotti, she promoted the service offering because of her own experience with one of our advisors. You know, we really do give people an incredible level of clarity and transparency about their financial life. You know, I don't know anyone who wouldn't love to have a spreadsheet that lays out in excruciating detail their net worth, their expenses, their retirement plan, their investments, their, their, their project to buy a new home and the progress they've made toward that new home. Those are things that we present to clients in very clear and digestible terms. It's not a lot of financial jargon, it's not a lot of gobbledygook. And we don't push any products, we don't sell anything. We just provide advice. And that combination of ethos really resonated with partners like Giddy Gotti. And so those partnerships really work well for us. And we've done others. One with Anthony o', Neill, one with Caleb Hammer. We've done a number of partnerships. We had one with Cody Sanchez. Those partnerships have really worked well for us. And that's how we sort of got.

Our initial interesting cl. I like that. I like that. And the advisor. Buying the advisor business, that's, that's. Yeah, that's smart. Okay. The. So actually now, now that we're on this topic, you have sold a number of companies over the years. I know this was a small acquisition that you purchased, but you, you've, you've sold a number of companies over the years and I'm curious your take on what that process is like. I think probably right now in the market, there are a number of companies out there that are later stage, that are struggling, that are, you know, maybe looking for a home. And I've talked to some of these CEOs and they're like, oh, I'm going to reach out to these 20 companies and I'm going to talk to all their corp dev teams and like, one of them is going to buy me. And is that how it works? So let me ask you, you having been through this many times, is that how it works?

Not in my experience. I've never really gone out and tried to sell a business. I just wake up and operate a business. And if you do that well enough and you make enough progress and what you're doing is of value enough to the marketplace, somebody will knock on your door. And that's typically how companies get bought in the startup realm, at least in my experience, is you are busily going about your work and some strategic stumbles across what you're doing and says that's really valuable. That would work well within Our business, we want to own that thing. Much more powerful of a dynamic to have than you scratching at the door of some corporate development team member, begging them to buy you. So, you know, we just tend to go about our business and try to build things that are of value and, and the rest sort of works itself out.

Do you take the calls? You know, I'm sure, you know, again, you, you go out there, you launch something, it's out there, it's public, people see it. I'm sure you get calls quickly, you know, not just at this company. Clarity at message one, like do you take those, every one of those calls or, or you know, all the time and kind of build those relationships. Or I know some people who say take every call even if nothing's going to happen, and other people who say just ignore them. You know, just ignore them until you're kind of further down the road. Like what, what is your stance on that?

Yeah, you can waste a lot of time with partnership discussions and, you know, corporate development people. And I tend to try to limit the amount of time I spend on things that don't have an immediate impact on the core KPIs that we're focused on within a given quarter. Right. And so one of the things I love about KPIs is that it really focuses your time and attention. Is the thing I'm doing right now contributing directly to one of our key performance performance indicators. Does it drive One of the OKRs we have for the quarter? If it does not, remove it from the calendar right now as it comes to, as it relates to, you know, strategic acquirers and having those conversations, most of the time those stem from some commercial relationship that you already have with a partner. And obviously if those can, you know, increase your revenue, increase your access to clients, give you access to a technology that will help power the thing you're trying to do. All those things are super important to pursue. And we obviously have lots of partnerships at Domain Money. We have service providers who are technology providers, we have distribution partners who are third party RIAs. So we have a lot of partnerships at play at Domain Money. And so I do the ones that, that speak to what my OKRs say for the quarter.

What is your. You've seen a lot, you know, over all the years. Again, as an investor, as an operator, you've seen the dot com boom and bust, you've seen, you know, the rise of SaaS, Cloud, you've seen crypto. Like you've seen all of this. What, what is your view on AI?

Oh my AI is quite a tectonic shift in technology. It is something that is evolving much faster than the Internet evolved. The infrastructure in place that enables its proliferation is massive. The dollars flowing into fueling these experiments is unprecedented. I don't think there's ever been this many dollars aligned to specific projects in such a short period of time. The velocity of it is just incredible and the utility of it is amazing. I think back to the first times I used OpenAI and what it was like last month and what it was like this month. Similarly, things like deep research, which is one of the features on ChatGPT where it walks you through the reasoning. I asked it a very complex research question and using the deep research function, and it gave me 26 pages of reasoning and walked me through all the things it was doing. And, you know, each one of those queries takes about five to seven minutes. And it's much more substantive than just your typical, you know, chatgpt response. And reading through the reasoning that it was doing in real time and watching it go through, go down a rabbit hole and get kind of stuck and then reverse course and try something else and explain that to me as it was doing it. To me, that was just an incredible light bulb moment of just how powerful and creative AI is. And it's to me, you know, bigger than the Internet and bigger than just a technology opportunity, because it really does represent an alien species that is evolving rapidly in our, in our world and will have profound impact on pretty much everything, whether it's personalized education, teaching you calculus and understanding where your pitfalls are in your, your canon of calculus knowledge, and reinforcing those areas in a way that is unique to your learning style. And we've talked about personalized education for a really long time, but AI makes that real to the way you peruse a bookstore. I went to the bookstore a couple weeks ago and I had my little air pods in and I was having a conversation with Gemini and I said, summarize this book for me. And she did. And then I said, well, we're go a little deeper. Give me the 10 most popular anecdotes from this book. And she did. And then I said, well, let's talk about number two, which happened to be related to the topic of infinity. And we have like a 15 minute conversation about infinity. And she knows more about that topic than anyone you could ever meet at any conference anywhere in the world who was an expert on infinity. Because this, you know, AI agent knows everything that was ever written about infinity, everything that's ever been published, everything's been researched, everything that's ever been studied, you know, and it's all accessible instantly to her mind and able to distill it in a format that I can then digest. And that is just a profound shift in the way information is synthesized and accessed by anyone in the world. And so I, I couldn't be more excited about AI. I know I'm giving you a long answer, but it, it warrants one. And as it relates to our business, you know, we really have found enormous efficiencies utilizing AI in the back office functions of what we do. And we only think that gets better as these models get a more refined and more useful.

Do you think you could build this company the vision you have for it? Everything. Could you do it without AI?

Not as efficiently, no. I mean, the business model is predicated on our ability to efficiently do financial planning. And so without AI, we couldn't do that.

What, what is the not in the product about maybe the, the actual operations of the business? What do you think today is the most useful use of AI, whether you're doing it today or you're seeing other companies doing? Like, I'm curious, where is it really moving the needle in today's world, in your view, like operating a business in.

Wealth management, in our business specifically, or just generally?

Generally, like in a technology company, you know, like if there's a place you would go use AI to run the business, where is that? Where is that?

Well, I mean, it's interesting because I would almost ask the inverse of that, which is like, where is it not being used? Right. So every engineer is using AI to help them code, every marketer is using AI to help them generate copy. Every operations person using AI to generate, you know, you know, emails for, you know, reaching out to prospects or client, you know, there's, there's just an unending list of things that this technology is being used for. I encourage our teams to use it as much as possible. At the same time, it's very important that we deliver a personal financial planning solution. Clients want to sit over, sit over, zoom, or meet with someone in person like we are now and talk through the nuances of, well, if I contribute the max to my retirement accounts this year, we'll have less to renovate the house. We want to renovate the house. And those competing forces really do require, you know, a nuanced conversation about values and timing and the impact of deferring those contributions and to make some real decisions about what is most important to a person around their money. And you know, AI is really good at things like, okay, we've aggregated all your accounts, we've extracted all the data, we've put it all into financial model. We can show you what scenario 1, 2, 3 and 4 look like. If the markets go way up, way down, stay the same, go up, go down a little bit. You know, all the different scenarios you could map out. AI is pretty good at that. But the nuance of values and priorities is something that a human, I think really requires or wants in financial planning. And so we focus on the pieces of the process that technology and AI can do well and we try to give more time to clients with human facing interaction with advisors because that's something they really care about and value. And so empowering the advisors with AI and giving them more time to spend with clients is really core to what we're trying to do.

You say that it's interesting because I had this conversation with my kids the other day. They're 9 and 11. And I was basically saying to them when they were born, my dream was that they would learn how to code, because I never learned how to code. And I thought like, that's the thing that I wish they knew how to do and that would help them, you know, as they go on in their lives. And now I told them actually really the thing to do is just put your phone away, put your iPad away, don't, you know, and just learn how to be a human being. You know, learn how to be face to face, learn how to. Because that's going to be the last remaining thing. That's not, that's not a, able, you know, it's like having actually that, that personal relationship, having that, that understanding of, of, you know, the eq having that, that's going to be the, the last remaining thing for, for, for humans to do it. I mean, to some degree, you know, it's, it's like. So when you say that, because I literally just had that conversation with them, I'm like, let's, let's focus more on being with, you know, talking to people, being with people, doing all that stuff and the other stuff, by the time you're old enough, you'll just be able to tell it to code something. I mean, already now, right now, I mean. So let me, let me ask you what, what do you, what is the big, I mean this, this company has been around not so long. So like, maybe this question is, you could take it more broadly, but what is the biggest challenge? Like truly the biggest challenge, you know, you've you've faced at Domain Money or, or broadly, like, what. What is that? That. That thing that sticks out in your mind? That's like the hardest moment in time you've had, and how did you overcome that?

Man, there's been so many. I don't even know where to start. Well, within. Within the context of Domain Money, certainly the pivot was the hardest thing that we've gone through. You know, there were moments when I really didn't know what the right direction of the business was to take during those experimentation periods. And it's really hard to suspend conviction, right, to be disciplined enough to say, I don't know. We're trying to figure it out. We're going through this experiment. It's designed to be objectively measurable, so we can determine if this is worth pursuing. Because it's really easy to just jump to an answer and get bias and conviction behind it. That's what the brain naturally wants to do. You know, if you ask somebody, do you like Coke or do you like Pepsi? They are instantly in a position where they feel as though they need to have an answer. And the brain wants to come to the feeling of comfort having produced that answer, regardless of whether or not that is, in fact, the answer. And there's a bunch of research that's been done on psychological preferences that confirms that people's need to have an answer outweighs their ability to objectively respond to a question. And that gives you, I think, an insight into how hard it is to remain objective as you're going through something as monumental as a pivot. When you have a team of, you know, were at 53 people, we took it down to 13 people. And even those 13 people are looking around the table going, adam, what. What are we going to do? You know, what's the plan here? How's this all going to work? And it's very tough, as the CEO, to, to say to them, I don't know, we're working on it. You know, that's not an answer that you want to hear from your employer. And yet that was the right answer, which is we need to go through a period of experimentation to figure out what is the right path. And that's. That's hard to do, especially when you have a team of people who come from traditional financial services businesses who aren't used to startups, aren't used to pivots, aren't used to the tumult of a startup. And I have to, you know, be grateful and, and, and humbled and, and thankful that you Know, many of my team members start with me through that tumultuous period and helped us get to the other side. And it's not for everybody. And you know, I'm sure I could have, I'm sure there were days when the pressure and the intensity got to me emotionally and I could have been more level headed about going through the pivot, but, you know, these things are part of the journey and you do the best you can and you, you try to figure it out. I have an enormous amount of personal pride and personal responsibility that I feel to my investors, to my employees, to my, to the clients to figure this out and make it work. And despite, you know, the prior successes that I've had as an entrepreneur, none of those really matter in the context of make listing work. We're either going to succeed or we're not. And I'm waking up every day trying to make that happen.

Did you have a group of people around you, not employees? Like, did you have anyone, let's say, to lean on, vent to, you know, brainstorm with, like, when having been through some of these moments, it's, you know, you can't maybe expose everything to the, to the team, you know, did you have people like that?

Absolutely. I mean, I am incredibly fortunate to have people like Jeremy Levine from Bessemer, who's one of our investors, Bill Gurley from Benchmark, who's a longtime friend and a close colleague, my brother Michael. These are all people that I've leaned on heavily at times of, you know, tough moments during a pivot that have really helped me think through different business models. We were contemplating how to manage the team's expectations. All of those dynamics are at play in the middle of the pivot, and I'm super grateful that I, that I have those resources to lean on. It'll be very hard to do it without that support system.

Yeah, it's very lonely. You know, it's so lonely that it's kind of, I tell people, you know, you, you need, you need those, those people who you can speak to fully, openly and on, you know, like just even just for venting purposes.

Like, yeah, yeah, your, your team has no conception of how lonely it is to be the CEO and how, how hard it is to navigate the, the optimism and the, you know, focus that you need to have in a startup, while at the same time, as I said earlier, being transparent and honest with them. It's a very hard thing to do. You don't want to mislead people. You don't want to them, you want to give them the honest truth. At the same time, they need to feel as though they're on a ship that's going to go somewhere meaningful. And once again, I have a little bit of an unfair advantage there because of my track record. Right. I am quite certain that there are people who have backed me and who works with me at Domain Money whose primary thinking is, well, this guy has figured it out a few times and he'll probably figure it out again, you know, I guess time will tell.

Yeah. Yeah. Well, let's. Where is domain money in three years? You know, it's 20, 28. Where, where are you at that point?

Yeah, we've built the best AI financial planning solution on the market and we've found a distribution approach that is unique and highly scalable. And I think we're quite far down that path already. We've, we've made some significant investments in technology to enable financial planning to be done in as much in an automated way as possible. And we've come up with a distribution approach for serving clients and accessing clients that's quite unique. There are 15,000 independent RIAs in the country. Many of them have investment minimums. Hey, if you don't have half a million dollars of investable assets outside of your taxable account, outside of your retirement accounts, excuse me, we're not going to take you as a client. Some, some firms have a $2 million investment minimum. Some of them have a million dollar investment. A lot of the leads that come into those firms are basically sent away. We're able to help those RAs serve those clients in a very technology efficient way and in a way that really delights clients. You know, we, if you were to ask 100 people, hey, tell me about your financial planning experience with your ria, they would not smile with delight. They would shake their head and say, ah, they gave me this 60 page plan. It had a bunch of sharp ratios and Monte Carlo simulations and charts and figures, most of which I didn't understand. What I really want to know is how much can I spend on vacation this year and should I buy or should I continue to rent a home? You know, those are, those are fundamental things that people have questions about, particularly in the segment of the market we're targeting, which is, you know, referred to as mass affluent. And so we've got a really valuable and unique solution that really does speak directly to the needs of the mass affluent segment. And we think we can use that technology and approach to power a big chunk of the industry. And so that's what Domain money looks like in a few years, and we're marching toward that goal.

Awesome. Let's just quickly transition. I want to transition to your background. Where are you from originally?

I grew up in Texas.

Did you always know you wanted to be an entrepreneur?

I wouldn't say that. I, I knew that I liked new ideas and starting things and, and doing things that was appealing to me, but I didn't know the term entrepreneur when I was a little kid. I was, you know, very fortunate in many ways, through luck of birth, to have the parents I had who were economically minded and at their core, intellectuals. And so our household was filled with copies of the Economist and discussion about the yield curve and interest rates and, you know, as a kid, yeah, it wasn't filled with talk about football and, and, and things of that nature. And so I was very fortunate to be steeped in a, in a, in a house filled with ideas and, and thinking. And I was also very fortunate to be the brother of the guy who founded Dell. You know, Michael opened my eyes to the expansiveness of what entrepreneurship can be and what it can achieve. And, you know, I marvel at how much Michael has achieved in his life and how many lives he's impacted, how many communities he's transformed.

Is he older or younger?

Michael's five years older than I am. Yeah.

Okay, got it.

So I was very fortunate to have that, that, the indoctrination of that at a young age. And so that, that opened my eyes to entrepreneurship and I couldn't be more thankful for it.

Did you have, like, was there someone, is, is it Mike, like, in terms of a role model, someone that you kind of looked up to, you know, I mean, is that, is that who it's been, you know, throughout your career?

I mean, you know, I'm very, very lucky to have two really lovely brothers, both of whom I'm, I'm very tight with and talk with a lot. You know, if you, if you're lucky enough to come from a good family and have love and support of your family, you're, you're lucky enough. Right. So I, I, in that regard, I've been very lucky. You know, I've had a lot of folks over the years who have been mentors and helped me along. John Mumford from Crosspoint, legendary entrepreneur and venture capitalist who really taught me the venture business and really taught me the entrepreneur gig. That's probably who I learned most directly from. Just, you know, roll up sleeves in the room with, with him. He really taught me how to, how to create companies. And so I would, I would credit John Mumford as being my most direct mentor, impacting, you know, how I go about starting companies and, and, and how that all works. But Michael's certainly been, been a great, you know, a great resource and I'm very thankful for both my brothers.

What, what, what drives you like at your core? Because at this point you've been successful multiple times over and I mean, you don't need to do it for the money. So like, what, what is the, what is the thing that drives you like at your core?

I like solving puzzles. I like creating things that delight and build value. To me, that's a fun thing. You know, it's very rewarding to be in the foxhole with a small group of people and conspire to figure out how to do something great. You know, it's just a, it's kind of a revolutionary act to band together with a small group of individuals and try to upend an entire industry. It feels very, you know, like we're gonna bust the machine and do something that, you know, most thought we couldn't. That sort of underdog mentality very much resonates with me and I find that to be very fun. I also feel, as I mentioned earlier, pressure to do a good job for my investors and my, my, my employees and, and our, our clients. You know, you take on this enormous responsibility when you start a company. You know, people have, you know, devoted their professional careers to domain money and I want to make sure that that pays off for them. Investors have given me lots of dollars to, and entrusted me with shepherding those dollars into something that is a cash flow generating machine and is of great value. And I take that responsibility really seriously. And that challenge to me is an exciting one.

So, so one, one last, I'm curious. You know, you spent, you grew up in Texas, you spent time obviously there in your career, but now you're in New York and you've built these businesses recently in New York. What, how would you describe the New York tech scene?

Well, I mean, I think what's remarkable to me is, you know, when I started back in 97, which is a long time ago now, you know, the Valley was really the epicenter of all things technology and innovation. United States and the proliferation of technology centers, particularly, you know, Raleigh, Durham, Austin, New York has been a, an incredible thing to witness. And you know, it, it used to be that you needed the, the concentration of the engineering talent in Silicon Valley, coupled with the risk culture and the venture capital community to have a cauldron of creation in the Valley, that unique set of ingredients was, you know, for a long time considered something that you couldn't replicate, at least not at scale. And what we've seen now is with the proliferation of technology beyond Silicon Valley, you know, it used to be that when there was some innovation in the valley around networking, you know, three engineers with pocket protectors would jump up and down and nobody would hear about it other than that little small cadre of people, you know. Now technology is so pervasive in our, in our society and impacts so much that innovation can happen pretty much anywhere. And so New York, being a financial center and a place that has a lot of highly motivated, ambitious, intelligent people with access to capital, it's become a real hub. And obviously, you know, all the major firms are here. There's now a massive ecosystem of entrepreneurs, including yourself, who are, you know, second, third time entrepreneurs, who have fueled money back into the ecosystem with angel investing and helping young entrepreneurs along in their journey. And so there's just a robustness to the New York ecosystem that is, you know, better than it's ever been. When I came here in 2000, you know, it was Fred Wilson and used Bird Ventures and Stuart Ellman and RE and Jeremy Levine, a Bessemer. And that was kind of it. Now there's, you know, pretty much every major venture firm in the country has a presence here. You know, I was over at A16 offices and you know, it's like, I think they have like people or something. Great office. And I think that's just incredible to see and awesome for the, for the community in New York.

Yeah. All right, last question for you is knowing everything you know today, what is the one piece of advice you'd go back and give yourself before you started your first job ever?

I would have held onto the Apple stock that I got from my bar mitzvah. Had I done that, you know, that would have worked out pretty good. I probably still would have done the things I've done as a startup guy right there. That would have been good advice. Honestly, the one thing I probably.

Would.

Do a little differently or wish I knew earlier is, you know, when you're working with people, you know, pretty quickly whether or not this person is going to be a, you know, a home run employee or partner, mediocre home run, you know, mediocre employer, partner, or a bad one. And there's a tendency in the mind to rationalize things and hope for a better outcome. And that's a mistake, you know, pretty early with people and partners. Whether or not something's going to work out well. Now, there are things that do require some nurturing and it takes time to find your footing with both people and partners, but it happens quicker than you think. And I think there's a tendency to string things along and push the can down the road, hoping that things will get better. And that's something I wish I had learned earlier and wish I had avoided at times.

That's really good advice, really good advice that I think people need to hear and internalize because I, I think even if, you know, actually, even if you know that that's true, you still have to remind yourself of that all the time because you always, you're, you're always hopeful and it's hard to part with people and it's hard, you know. So that, that's, that's really good advice.

Yeah. You spend a lot of time rationalizing in your mind, oh, well, we spent all this time recruiting this person and they have the right background and wow, the industry really respects that person. And you know, this is going to be a great thing. And then you find yourself in a spot where you realize it's not ideal. And that can happen with partnerships. You know, you spend all this time trying to close a partnership. You get them all spun up, you get through compliance, you get the agreement signed, you have the financial entanglement between the two entities, and then you realize, hey, this is not a good deal. You spent all this time and energy on it. You don't want to toss that away. That's backward thinking. All that time is sunk. All that time is gone. What matters is right now, what does this yield for again, the okrs for the quarter.

Adam, thank you very much for doing this with me. I love every time I get a chance to talk to you. So thank you for doing this.

Great to be with you, Daeder, and thanks for the time.

Awesome. I hope everyone enjoyed a lot to go through in this episode. So I hope you enjoy it and if you did, please share with your networks and we'll see you for not next episode of Not Another CEO Podcast. That's a wrap for this week's episode of Not Another CEO Podcast. Thanks for joining. For show notes and more, please Visit not another CEOPodcast.com we'll see you next week.