Jacob Tally | Prospero Wealth

Josh Hile: Welcome back to the Advisor View Podcast. I’m Josh Hile, CEO of Citizen Mint, and today I’m joined by Jacob Tally at Prospero Wealth. Thanks for joining us, Jacob.

Jacob Tally: Yeah, thanks, Josh. It’s great to be here.

Josh Hile: So maybe you can start us and talk about your background and your path into wealth management.

Jacob Tally: Yeah, I’d be happy to. So my first job out of college was actually at Fidelity Investments, placing client trades in a call center. So in a way, I started in this industry, I took a long detour and kind of came full circle. I’ll spare the details of the detour, but just say that several years after my MBA, my wife, who I had met in grad school, she and I moved to Seattle because she’s from the area, and I kind of hit reset on my career, which had been focused on corporate finance up until that point. And starting in 2014, I then spent 10 years working at VC-backed startups, mostly on the consumer side of things. And what I learned at those startups is that I really love building. There’s nothing better than going from 0 to 1 kind of alongside a high-performing team.

Josh Hile: Yeah.

Jacob Tally: Right? Like, especially when there’s real camaraderie and you’re kind of sharing a vision. And so it was a lot of fun, but, you know, in 2024, after 10 years of startups, a couple different ones and no big exits. I was kind of asking myself like whether I had another decade of that in me and I felt like I did, but that energy needed to be directed into something more of my own. And I realized it didn’t need to be a business with a trillion-dollar TAM, you know, or something that was going to 100x every year.

Josh Hile: Yeah.

Jacob Tally: And so I wanted something more durable, long-term, and kind of personal. And I was also at a stage in life, and I know a lot of my peers were in ours too, where the personal finance questions were becoming more difficult. I think you accumulate wealth up to a certain point, and then the questions start to become more difficult. It’s like, should the next dollar go into my retirement account?

Josh Hile: Yeah.

Jacob Tally: What if I want to be work optional early? How do I become more tax efficient now that I’m entering my peak earning years? And researching those questions and working through them kind of made me realize that’s really what I wanted to do as a career. It’s really what I had wanted to do all along. And so kind of like the proverbial, the best time to plant a tree was 20 years ago. The next best time is now, right? So yeah.

Josh Hile: And so how’d you find Prospero and, um, like your relationship with Eric, who— yeah, who runs it.

Jacob Tally: I mean, very, very fortuitous, kind of serendipitous. Um, you know, so I made this decision that I wanted to pursue this as a career, right? But what I was unsure of was kind of like the how. Um, I was like, do I do this like totally solo, go out on my own, like never really having done this before? And there’s a lot of, that’s way more feasible today than it was 10 years ago. There’s lots of good, you got XYPN, a lot of good platforms and companies and materials out there. But I also knew I’d really benefit if I could find an established RIA that I could work with, that was aligned, who’d give me what I needed from an autonomy standpoint and things like that. The question was, could I find that fit?

Josh Hile: Yeah.

Jacob Tally: And so, you know, I’m like doing all my homework. I’m perusing like subreddits and listening to Kitces podcast, right?

Josh Hile: Yeah.

Jacob Tally: And so this was late 2024. I’d kind of decided to go out on my own ’cause I hadn’t found a good fit. Yeah. And I hear Eric Franklin on the Kitces podcast. Here’s this guy, career switcher here in Seattle area. I was like, you know what, I’m just going to reach out to this guy, tell him how much I appreciated his podcast and bounce some ideas off of him. And he was like, hey, yeah, we should grab coffee. And one thing led to another and he was like, I want to expand the Prospera Wealth practice. I’m trying to bring advisors on board. I think you’d be a great fit. And learned a little bit more about what his vision was and it just felt like a good fit. And I’m immensely thankful that I that things worked out the way they did because I’ve— now that I’m like, you know, a year or two into it, I’m like, I don’t know, like, I just— it sped up the education and the ramping so much. Like, there’s so many things I didn’t have to figure out on my own because Eric had kind of gone through a lot of those learning curves.

Josh Hile: So yeah. Yeah, no, definitely having somebody do that and like understand like where not to do it or even like Building a tech stack for a wealth management firm is incredibly challenging. Yeah.

Jacob Tally: Building the tech stack and cultivating the relationships, right? Like, I mean, we’ll get more into it, but it’s kind of like, here’s a given strategy, right? Whether it’s long-short or custom indexing or whatever the case may be. And there’s all these different providers, right? And products and services. It’s like, how do you know which one to like work with or what the pros and cons of each of them are? And he had done a lot of that homework. And so it just made things so much easier.

Josh Hile: Yeah, yeah, definitely. What about just how your kind of former career leads into like how you go about your business? So being, you know, tech startup employee kind of like, and I know Eric has a big background on the Amazon side. And just how does that also lead to who you really focus on? And maybe you can talk about your focus areas of like clients.

Jacob Tally: Yeah. And so, I mean, we focus on kind of mostly tech and to a lesser extent, kind of with my background, startup employees, it’s kind of like a Venn diagram that overlaps pretty heavily, right? And what they have in common is heavily equity comp focused.

Josh Hile: Yeah.

Jacob Tally: And with that equity comp comes complexity and kind of uncertainty from the client side. And so the honest answer of why is kind of like, it’s just because that’s who we are, right? That’s where our relationships and our credibility exists and already lives. And so I think that’s sort of the surface level answer, but I think the deeper thing behind it is kind of like, I think a lot of tech employees are really skeptical of financial advisors.

Josh Hile: Yeah.

Jacob Tally: All of us were as well, like when we sitting on the other side. And so I think that kind of gives us a level of kind of credibility and having sat in the shoes of a lot of our clients, it just helps us build rapport and gives us a little bit deeper credibility with them, right? So we’ve sat through vesting cliffs and layoffs and all sorts of tech changes and things like that, and we know the mechanics of equity comp. And so I think that’s the big thing on the client side, but it also candidly kind of affects how we run our firm too, right?

Josh Hile: Yeah.

Jacob Tally: operations. So you mentioned like tech stack and, you know, I think we’ve been through like 3 AI note takers in 2 years.

Josh Hile: Yeah.

Jacob Tally: We’re always, you know, kind of thinking through like what are, you know, the best products and services we should be using, like what’s best in class. And, you know, we really think about it like a product team would think about their tech stack in a, you know, in any other organization. So So there’s that piece. And then also just, you know, we’ve branded our process Agile Financial Planning. So anyone that’s worked with an engineering org, you’re familiar with, you know, agile planning and tech sprints and things like that. So, you know, we’re less about delivering this big 40-page financial plan and more like, what are the 3 to 5 most important things that we can be working on? And let’s just kind of like knock those out piece by piece, right?

Josh Hile: Yes. Yeah. What about just how, um, and maybe this is part of what you just said about the agile planning, but how Prospero approaches wealth management differently and approaches clients differently. And, um, you know, you mentioned RSUs and just all the equity comp, and maybe that’s like really a huge differentiation, which I think it is because that can be incredibly different across companies and how people get Yeah.

Jacob Tally: I mean, so do you mean more of like the—

Josh Hile: I mean, how are you going to market and saying, hey, versus these other 5 wealth managers you might be talking to or thinking about, here’s how we’re going to work with you differently.

Jacob Tally: Yeah. So I think on one hand, the good planning is kind of the same everywhere, right? Like, what are the client’s goals and what are the best vehicles and strategies to get you to those goals or achieve those goals? And so I think any good advisor starts that way. I think the difference is really kind of on the inputs. Equity compensation arrives as all these vests on a calendar. And a good generalist, like advisors kind of exist on a spectrum, right? Like a good generalist might be able to build a plan for that, but maybe tech clients aren’t really the bulk of their book.

Josh Hile: Yeah.

Jacob Tally: And so for us they are, and I think that familiarity compounds a lot, right? And so It’s familiarity with the tools that one uses for equity comp, whether it’s, we’ve mentioned long-short, custom indexing, exchange funds, 351 exchanges, list goes on. But we have familiarity with that. And then I think from the goals side of things, there’s a difference too, right? Because a lot of our clients are not necessarily planning to work until age 65. Maybe they are just for personal reasons, but they want to be work optional or or maybe take a sabbatical. And if you’re sitting on a lot of fast-growing tech wealth or a really healthy portfolio, you might be work optional years before that. And it raises these other questions of how do you fund health insurance for 5, 10 years before Medicare, or what accounts do you draw from? These types of clients that we work with just have different problems where it’s like, if you’re not used to working with a lot of these kinds of clients, you’re just not gonna be as familiar with those strategies. And so I think, you know, a big part of our positioning is just like a familiarity with these strategies. We’ve used them, we have lots of clients that use them, you know, and I kind of touched on this a little bit before, but it’s kind of, it goes back to the, some of the partners and providers we work with, right? Of like, We’re not just scrambling like, hey, let’s figure out how to do long-short. It’s like, here’s 3 different long-short managers that we could set up SMAs with. Here’s when and why you would want to use each of those, because they each have pros and cons perhaps.

Josh Hile: Yeah.

Jacob Tally: And so I think that that’s another part of our positioning of how we do things differently. It’s not just like, here’s the strategy. It’s like, being able to speak to it at a little bit deeper level of authority.

Josh Hile: So yeah. And how are you all going about, you know, finding those clients? Like what’s kind of the main strategy? Is it referrals? Is it, you know, going to tech conferences? How do you actually like find these individuals?

Jacob Tally: Yeah, so this is where I’ve had a lot of fun because my background in startups included several roles kind of more on the marketing side and digital marketing side. Yeah. And obviously, the world’s changing so fast with AI. I mean, the bulk of our referrals and clients has largely come from our networks, right? Our team, which is I think 6 advisors now, we all have this kind of like career switcher background, generally speaking. So we all have deep networks in these different firms. So that’s been helpful. But where I think we’ve started to get a lot of traction now is building out content on our website. I’m really trying to think about AI engine optimization, AEO, and things like this to drive traffic. And we’ve had some really good success in those areas. Also just doing things like these podcasts and talking to people like you. I think one of the things you really see on the marketing side is I think PR is going through kind of like a renaissance almost of like, because everyone’s focused on LLM citations, like the way you get that is through, you know, place, external placement, right? And PR can be a great way to do that. We’ve had some good success there too.

Josh Hile: Interesting. Yeah, that’s, that’s so in, and that would be from a geographic perspective, that means that it’s gonna go beyond the Seattle area and go beyond, like, more geographically the whole US.

Jacob Tally: Yeah, exactly. I mean, that’s one of the big, I think, strengths of, like, we’re a 100% virtual firm. We don’t have a physical office. Yeah. Um, and we have advisors kind of spread up and down the West Coast, so we have a West Coast bias. Um, surprisingly, just given our client focus, right? But, um, we are 100% virtual, so that makes, makes things really easy, and our clients like that too, right? I think especially post-COVID, most people don’t want to have to drag their butt to the financial advisor office and sit there through presentations.

Josh Hile: Yeah, no, definitely. Maybe you can just talk, and I think this will be interesting to a lot of the listeners, but just managing a concentrated stock position for your client and how you think about risk, taxes discussion, because even What I’ve seen in the past when I’ve been working with clients and especially like tech clients, you know, who we had a lot of, like, and this goes back a while, but we had a lot of early Microsoft employees and they were so attached to that position within the company. And so how do you detach them from that position to be like, let’s take risk off the table?

Jacob Tally: Yeah. I mean, this is such a hard question that is so unique to each client, right? And it’s kind of like you’ve got your— the easy part is kind of like the destination. Like, here’s the model portfolio, here’s where we want to get you to. And then it’s kind of like there’s lots of ways to skin a cat and get there.

Josh Hile: Yeah.

Jacob Tally: And so, you know, so what are the client’s goals, right? So I’ve got a client, he’s got a lot of RSUs with Amazon, and in his case, right, he’s got a home renovation or home purchase he wants to make for his family. Like that creates a liquidity need that would be very different than a client in the exact same situation that doesn’t have that same liquidity need. Right. And so, you know, goals, risk tolerance. I think risk tolerance is a funny one too, because it’s like you could have 2 clients at the same company and they sit in different departments and they could have totally different outlooks. Right.

Josh Hile: On the company.

Jacob Tally: On the company’s prospects, right? So it’s kind of like if you’re in, like, if you’re at Amazon again, like, in your, like, on the maybe the marketplace side, that could be totally different than if you’re an engineer on the AI side, like, right? And so, which isn’t to say, you know, you wanna take those factors into account, but it’s, which is to say their unique perspective on the risk. But the questions are the same, right? Let’s think through the, behavioral kind of, what if the stock goes up 50%, down 50%? How are you going to feel? One of the nice things I think is behavioral finance has come so far along now. It’s kind of well-established, right? Like the loss aversion, the feelings of loss are much stronger than the feelings of gains and things like that.

Josh Hile: Yes.

Jacob Tally: Right? And so You know, thinking, but, but again, like to bring it full circle, like it’s kind of like, there’s not a one-size-fits-all. We talk through these things and it’s kind of like, what are the goals? What are the different levers we have to pull and how do, how do we get there?

Josh Hile: Yeah. So yeah. What about, what about just navigating the differences and like, how do you work through that with clients? And I, I’m thinking about differences of like, maybe you can, cuz this is a broader audience, like What’s an RSU versus an ISO versus an NSO and liquidity events and how do you navigate those differently?

Jacob Tally: So it’s changed even just in the time I’ve been doing this. What’s changed is candidly the client side and LLMs and AI, right? So I think before, because it is so complex and there are so many different tools, I think it behooves us as advisors, we have to go a lot deeper in modeling these things out because you can’t— it’s not as simple as just like, hey, here are options A, B, and C, and D, and we’re recommending option A. The client wants to model out, and especially our clients, especially they’re going to— if we don’t model it out and kind of show them, they’re going to go do it on their own. They’re going to bring it back to us and be like, why did you choose this?

Josh Hile: Yeah.

Jacob Tally: And so You know, for RSUs, it’s kind of like, well, what’s the, what’s the count, what’s the best calendar look like and how often is that happening? And what does it look like based on top of their other compensation and tax brackets and future expectations about how or whether those things potentially change? So, you know, it might be like you’ve got this big concentrated position, we can afford to just hedge what you have, sell future RSUs as they vest, and that’s kind of how we’ll go forward. That would be very different than someone who’s maybe pre-IPO at one of these, whether it’s SpaceX or Anthropic or whatever, and that position’s like 80% of their net worth, right? Those are 2 very different scenarios. So we’ve done this now enough that I think we’ve seen kind of model scenarios, right? Whether it is that big IPO coming up or whether it’s someone sitting at a more established company doing RSUs. Those are the 2— I feel like RSUs are pretty common now.

Josh Hile: Yeah.

Jacob Tally: the general tech industry’s kind of settled on that largely as like the primary vehicle of equity compensation. But, you know, we do see some really early employees at some of these startups that have, you know, QSBS and ISOs, incentive stock options and things like that, that come into play. And those have their own playbooks too. So I think we have kind of established playbooks for each of these scenarios. But it’s just a matter of kind of like walking clients through the tax implications because the clients, it’s very easy to look at things pre-tax and say, this strategy seems most advantageous. What is less, what’s a lot more difficult is what is the after-tax impact, especially as it relates to other portfolio options, right?

Josh Hile: Yes.

Jacob Tally: if there’s money or liquidity to be deployed in some other strategy, it might be able— it complicates and might be favorable to the overall tax picture, whether that is a private investment, whether that’s, again, taxable long-short and harvesting losses. Each of those things can affect the overall tax picture. So to get back to the question of how it’s really just It’s modeling out scenarios for clients and making it personal and unique to their situation to show them what that can look like.

Josh Hile: Yeah. And what mistakes do you often see that create maybe unnecessary tax bills?

Jacob Tally: Yeah, I don’t think there’s not any one thing. I think what we generally see is kind of a lack of conviction again of what that after-tax picture looks like. So, you know, if I— but I guess if I was going to pick 2 places where I see things bite the hardest, like first is on RSU withholding, right? So supplemental income, like an RSU vest, is typically withheld at 22% federal until you cross, you know, the threshold of $1 million, and it just jumps to 37%. And so a lot of tech employees live in that in-between of depending on what their marginal rate is and things like that. And so especially if RSUs are kind of new to them, that can often come with a surprising tax bill. And then the second we kind of touched on is ISOs, and that calls into question like AMT, alternative minimum tax. And so that can be a big one too. I mean, right now the AMT threshold’s a lot higher than it used to be in years past, so it’s not quite as much of an issue, but it still can be, especially if you’re at one of these firms with really high growth trajectory. So both of those ISOs with their holding periods and really specific timing with the exercises and holding, you want to make sure you’re not going to mess those up and get yourself into a tax problem.

Josh Hile: Yeah. What about Maybe you kind of touched on this, but just that behavioral bias of really getting to the client and being like, hey, you’re going to actually need to sell some of this stock. And even if the company’s going parabolic, it’s like, hey, you should probably be taking chips off the table. What does that conversation start like?

Jacob Tally: Yeah. So I think one of the questions I like to ask, because again, it’s usually RSUs.

Josh Hile: Yeah.

Jacob Tally: And so it’s kind of like RSUs is really just cash comp in stock form, right?

Josh Hile: Yeah.

Jacob Tally: And so if you were to ask a client, like, if those RSUs had actually been issued all in cash, would you have taken all that cash and put all of it and bought stock in your employer, right?

Josh Hile: Right.

Jacob Tally: Like, probably not. You would’ve allocated some percentage of it maybe to your employer stock or more likely maybe to the sector as a whole if it’s like the Q’s or something like that. And so it’s kind of like, what is the right ratio to hold that? Again, a lot of our clients have built their wealth on the backs of a single stock and a single concentrated position. So you don’t want to my role is not to come in and be like, oh my gosh, you have way too much. We need to sell all this over the next couple years because this is way too risky. I actually think our firm is much more understanding of that desire to hold that upside. But yeah, I mean, we want to let our clients continue to have some of that upside. It’s more about what fits for you and let’s have rules in place for whether it’s tracking some moving average or percent of net worth or some combination of that. Let’s agree on rules upfront and thresholds so that we don’t find ourselves trying to make an emotional panic-driven decision in the future.

Josh Hile: What about just thinking about private markets, your clients’ interest in private markets? Obviously they have concentration sometimes in a private stock, sometimes in a public stock. How do you think about that and where that fits into a portfolio for some of your clients?

Jacob Tally: Yeah, so I’m going to get really nerdy and wonky here, but I actually take it all the way back to modern portfolio theory and capital asset pricing model, right? And the CAPM portfolio is never the S&P 500 or even all public equities. It was built around the idea of a basket of all the investable assets in the universe, and a significant share of investable assets are private. And so on pure theory—

Josh Hile: It’s actually gotten bigger too.

Jacob Tally: Right.

Josh Hile: Yeah.

Jacob Tally: The share of private as the overall has only gotten bigger, right? And we’ve definitely seen this in the States as the number of public stocks has declined.

Josh Hile: These companies have stayed longer, private longer.

Jacob Tally: Yeah, exactly. And so I think on pure theory, there’s a place for private markets in a portfolio, all else being equal. Now, the other part of that, all else being equal is doing a lot of work in that statement, because the same theory is built around no transaction costs, no taxes, all these things. And so that’s where the work comes in is because in practice, for a lot of private investments, fees might be higher. The structures can vary very widely.

Josh Hile: Yeah.

Jacob Tally: There’s often investment minimums. And so it becomes a real conversation only once a client crosses a certain level of wealth, because you want the position to be small enough that illiquidity or a total loss doesn’t move the entire plan. And so minimums can set a floor for what that can be or how much it can look like. Because if the minimum’s like $100K and that’s like 10% of their portfolio, that’s very different than if it’s 1% of their portfolio.

Josh Hile: Yeah.

Jacob Tally: So I think all those factors come into play. And then again, just the diligence burden is a little bit different. because obviously public stocks are not all the same, but they are standardized and kind of like there’s a price, dividend, well-known ratios, trading mechanics, um, like liquidity profile is generally the same. Um, and with private assets, that’s just not the case, right? So every deal has its own structure, its own fee stack, liquidity terms. And it’s, you know, it’s not a reason to avoid it. It’s just like the selection matters a lot more in a very different way. And you know all these intricacies better than me, right?

Josh Hile: Yeah.

Jacob Tally: Then you’ve got private equity versus private credit. And so I think the lack of standardization is something that a lot of clients and prospects maybe don’t fully appreciate. They think like, okay, yeah, I want a slice of my portfolio in privates. It’s like, okay, why? Say more. to what extent? Is it just to have that as part of your portfolio? Is there a specific sector you’re thinking you need exposure to? Let’s talk through that. So I mean, to get back, kind of bring it full circle, yeah, there’s a place for privates in the portfolio, 100%. It’s just kind of like, we want to make sure that tail’s not wagging the dog, that sort of a thing.

Josh Hile: Sorry.

Jacob Tally: No, I’m good.

Josh Hile: Yeah. So, and then that totally makes sense. And I think that’s actually this question I start with when we talking to like some of our clients, we’re like, hey, what are you actually trying to achieve here for your clients? Is it some level of diversification? Is it growth? Is it a replacement for something else in their portfolio that you Or like, and usually we try to find like, you know, non-correlated assets that are very differentiated from what they’re going to get elsewhere. And that’s like really the goal is to reduce that volatility for clients to not make behavioral errors when the markets turn over, which is really an incredible value that advisor usually provides. And it’s like, we’re here to make you so that when the markets go down 30%, you’re going to not start doing stuff that’s going to like really impair your future financial future. Yeah. Right.

Jacob Tally: Yep. 100%. Yeah. And again, every client’s different, but it’s kind of like if they have— it might be they want passive income or something like that. And there’s passive income in the functional sense of interest and dividends, but some of them actually maybe have passive income from a tax sense. And it’s kind of like if we can— if there are certain investments truly generating passive income, maybe there’s private opportunities in real estate that could offset that.

Josh Hile: Exactly.

Jacob Tally: Right. And things like that. And that’s a totally different opportunity and picture.

Josh Hile: Yeah. And I think that’s— we can get into this as the next topic, but I think that’s where the industry’s going is instead of like, hey, you’re just a 50/50 allocation, like 50% equities, 50% fixed income, or a 60/40 or a 70/30, which is traditionally how people have done it. It’s more personalization to the client’s very specific financial goals and their liquidity needs.

Jacob Tally: Yep.

Josh Hile: Which I guess that kind of goes into like, where do you think the industry’s headed over the next 3 to 5 years? How is AI going to play like a huge portion of that? So.

Jacob Tally: Yeah, I mean, that’s a really, like, I’ll take it in the bite-sized pieces and we can like get really maybe more broad and yeah. But I’d like to piggyback on what you were talking about of asset liability matching, goals and asset matching.

Josh Hile: Exactly.

Jacob Tally: It’s kind of like, I think up until really recently, all the focus has largely been in this world has largely been on investment allocation and 60/40, 70/30, 80/20. And I put just as much focus for clients on your tax location. between tax-deferred, tax-free, your Roth HSA stuff versus taxable brokerage accounts, what does that ratio look like? Because I think there’s a lot of value in having diversification even amongst those different tax locations because who knows what the tax rate profile picture looks like in 10 years after whatever legal political changes, right? And so having diversified tax locations matters too, right? And, you know, kind of going back to the, like, are you hoping to maybe retire early, right? Like, if so, like, a common thing we see is like, yeah, I want to be able to retire early. And then you look at their portfolio and it’s all in a tax-deferred 401. And it’s like, well, I have some good news and bad news. Good news, you’ve socked away a lot of savings and retirement investments. Bad news is you’re going to be paying a penalty if you try to access any of that before 59 and a half, right?

Josh Hile: Yeah.

Jacob Tally: In most cases. And so it’s like, all right, this is going to seem counterintuitive, but we actually kind of need to build assets up that are taxable potentially, right? Or look at Roth conversions or things like that. And that, and that’s like where the value add is of like doing planning and, you know, having done this for clients before and things like that. But you can kind of— it’s, it’s almost like, you know, it’s just another aspect of lifestyle design, right?

Josh Hile: Yeah.

Jacob Tally: It’s kind of like, where do you want to be? And do you want to move to a low-tax state? Or, you know, if you retire, maybe you just don’t work for a year or two, and then we can do some Roth conversions. And, you know, oh, you want to live abroad? Well, here’s how that complicates your tax situation, right?

Josh Hile: Yeah.

Jacob Tally: And these countries are going to tax ETFs like this, or, you know, whatever the case may be. So AI can— so I don’t know, I could pause there and then we could pontificate about like how AI is or might change it. But like, that was kind of— I wanted to build on kind of what you were referencing there, like this goal and asset and allocation matching. I do think that personalization, level of personalization is like where everything is moving. Oh yeah.

Josh Hile: Because I think that’s what clients expect. It’s like, they’re like, if you’re, I’m going to pay you, I want it personalized to my specific situation and just not be in another bucket across your firm.

Jacob Tally: Exactly. And I think, you know, yes, that’s what they’re looking for. That’s the real value add because I mean, it’s been the case for a while now. If all you want is the investment allocation, like robo-advisors, things like that are, you know, can do that piece pretty well. Like, yeah, part that can’t really be out-of-the-box standardized is that customization and matching it to your goals and understanding you.

Josh Hile: Yeah.

Jacob Tally: And I think that is an area where like AI is kind of changing the game, but even then, you know, it’s still so sycophantic and inclined to tell you what you want to hear. And I’ve even had this kind of with some client engagements where it’s like, where we’re going back and forth on recommendations and they’re coming back with questions to me that I can tell are very much driven by an LLM.

Josh Hile: Yeah.

Jacob Tally: And, you know, And, and, and they’re perfectly legitimate questions. But, you know, maybe skepticism about the recommendation and, and, and proposal of like, well, why not this, right? Or what about this? And I’m like, that’s certainly an option on the table. Like, here’s the pros and cons of that and why I didn’t recommend this, right? And bringing up issues maybe that their LLM didn’t think to surface or want to surface, right?

Josh Hile: Yeah.

Jacob Tally: It ran maybe counter to their narrative or where the chat was going, right? Yeah. So yeah, I don’t know. It’s a new world. It’s a fun one, but yeah. Yeah.

Josh Hile: Okay. And maybe just to kind of like close this out, because I always like to ask this question. So what’s one thing that people don’t know about you or one hobby that you have?

Jacob Tally: Ooh, okay. So I’m probably the only person in America who’s smoked a Japanese A5 Wagyu brisket twice. So—

Josh Hile: Okay, tell me about, tell me more.

Jacob Tally: So one of my startup stops was at a company called Crowd Cow, where I was like the first full-time employee. I joined Joe and Ethan there, and Crowd Cow started off all about sourcing meat from small independent farms and ranches and making it available, like ship it straight to your door, right? And so my first job there was like going to find these farms and ranches and setting up the supply chain and all that. And we then added on Japanese Wagyu. One of our co-founders, Joe, he spoke Japanese, like went to Japan and cultivated some of these relationships with some of the Japanese Wagyu producers and companies. And so we sourced like Japanese Wagyu and, you know, so I got to do all these like photo shoots and eat all this Japanese Wagyu beef. Like there was a point in time I was probably eating, I don’t know, like more Japanese Wagyu than anyone else in America. It was just like, crazy. But what the market didn’t have was like, you could always get the like strip loin or ribeye or filet, right? Like the kind of popular, call them like the Hollywood cuts that you’ll find on any steakhouse, but you can’t really find Japanese Wagyu in these other cuts, right? And so I’m from Texas, and so I love, I’m all about like smoking meat and brisket and stuff.

Josh Hile: Yeah.

Jacob Tally: And I was like, we should try to source Japanese Wagyu briskets. And we did. And we started, you know—

Josh Hile: And why is that? Why can’t you source that specific, like, what do they use that for, like hamburgers or what do they use it for?

Jacob Tally: Yeah, it comes down to the fact that like meat is so different by country, right? In terms of like how they value these different cuts.

Josh Hile: Yes.

Jacob Tally: And so the general thinking is that like an American would never pay X dollars per pound for these briskets.

Josh Hile: Yeah.

Jacob Tally: And so like the, so people just don’t do it. And then the other aspect of it is kind of like the way they prep it and cut it. ‘Cause like if you look at, you know, if you go to like a butcher shop, you’ll see the little cow diagram and it’s like, here’s the way they break it down. Like that’s also different for like country to country, right? How they break it, break a cow down. And so in Japan, what’s kind of funny, so We imported some of these briskets, and this is a special type of Wagyu called Olive Wagyu, which I could go on about. But these briskets, Josh, were like 30 to 40 pounds. For American listeners, if you’ve not bought a brisket before, a packer brisket is going to run generally 10 to 15 pounds. Once you’re getting 14, 15, 16, that’s pretty big packer brisket.

Josh Hile: Yeah.

Jacob Tally: These were like 30 pounds, sometimes bigger. And that’s just because, like, again, the way they broke it down, it was much bigger than just like what we do. And so it was a whole thing actually in terms of like creating—

Josh Hile: I mean, that’s a lot of brisket to cook at once.

Jacob Tally: Oh yeah, no, it’s a lot. Yeah, it’s a lot. And I mean, it was, look, it was delicious. No regrets. Yeah, I could never have afforded to have bought one of those briskets myself, but getting to do it and create the content for the company was a lot of fun.

Josh Hile: So that’s incredible. Yeah. Well, that’s a good way to end it. That’s, that is the most unique one I’ve had. So here we go. Um, well, thank you so much for the time and really appreciate all the conversations. Super interesting. I mean, like on the tech side of things, it’s just incredible like that. It’s such a complicated market for that. Uh, it is all those equity compensations. So yeah.

Jacob Tally: Yeah. Terrific, Josh. Well, thank you so much, Josh, for the opportunity. It’s been a lot of fun chatting with you.