You’re Not As Diversified As You Think | Dan Pascone with Rob Petrozzo | Podcast #19

Posted on June 20, 2025 by Dan Pascone

Answer Box: TL;DR

Your portfolio is probably more concentrated than you think — even if it “looks” diversified. In this episode, Dan Pascone talks with Rob Petrozzo, co-founder and Chief Product Officer of Rally, a platform that turns museum-quality collectibles into fractional shares you can buy and trade like stock. They discuss why wealthy families have long used assets like classic cars, fine art, rare cards, and even dinosaur fossils as part of their wealth strategy, how Rally sources and securitizes one-of-a-kind pieces, and what role these “alternatives to the alternatives” can play alongside traditional investments. Rob also shares his personal lessons on money, hustle culture, and why doing what you actually care about can be the most powerful financial decision you make.

Key Takeaways

Most investors are diversified on paper, but concentrated in practice. Many high earners have portfolios dominated by public equities, their employer’s stock, and maybe some real estate. Alternative assets like collectibles can behave differently through economic cycles and add another layer of diversification when used thoughtfully.
Collectibles have quietly been a wealth tool for the ultra-rich for generations. Museum-grade cars, art, watches, sports memorabilia, rare documents, and even dinosaur fossils have long been bought, held, and sold by wealthy families and institutions. Historically, access was limited by high prices, relationships, and auction-house gatekeeping.
Rally essentially creates a “stock market” for unique items. Their team acquires or partners on high-end assets (Honus Wagner cards, Stegosaurus skeletons, classic Porsches, etc.), places each in an LLC, completes an SEC-qualified Reg A offering, and issues fractional shares that investors can buy, hold, and trade via an app with minimums as low as ~$10.
Valuation is a blend of data, expertise, and relevance. For one-of-one or very rare items, Rally uses auction comps, insurance values, expert input, and a detailed checklist (rarity, provenance, cultural relevance, historic returns) to set an IPO range — much like pricing a traditional company going public.
Sellers can get liquidity without giving up the entire asset. An owner might sell 50–80% of a trophy item into an IPO while retaining a meaningful equity stake. They unlock capital today yet still participate in any future upside alongside a community of collectors and investors.
“Alternatives to the alternatives” are emerging as a real category. As institutions expand beyond stocks and bonds into private equity, real estate and traditional alts, a next layer is forming: tangible, finite collectibles with long price histories and passionate global followings. The key is focusing on blue-chip, historically resilient pieces rather than speculative fads.
Emotion, when paired with expertise, can be an investing edge. Rob argues that deep, long-standing passion for certain categories (vintage Porsches, specific watches, iconic cards) can help investors “see around corners” — as long as they combine that emotional connection with research, patience, and a portfolio mindset.
Hustle without boundaries has real costs. Rob’s own journey building Rally involved years of nonstop work, fundraising cycles, and emotional whiplash. He’s now more intentional about making weekends “real weekends” and cautions younger professionals not to sacrifice health and relationships chasing money alone.

Key Moments

00:29 – Introducing Rob and Rally. Dan welcomes co-founder & CPO Rob Petrozzo, whose company turns fine art and collectibles into fractional investments.
01:43 – “A stock market for collectibles.” Rob explains Rally at a high level and distinguishes museum-grade assets from the stereotype of “cards in the attic.”
03:57 – How do you value a Stegosaurus skeleton? Rob walks through their valuation framework using comps, expert networks, a 24-point checklist, and cultural relevance scores.
06:36 – Building the sourcing network. The long game of flying to meet collectors, auction houses, and brokers worldwide before ever asking for deals.
08:34 – Why some sellers prefer Rally over auctions. Certainty of execution, ability to retain partial ownership, and avoiding big auction premiums and exclusivity periods.
10:22 – Turning a Honus Wagner card into shares. Rob breaks down their use of Reg A, LLC structures, SEC filings, and IPOs inside the app so hundreds of investors can own a slice.
13:53 – Who actually owns the asset and where is it kept? How Rally secures items (like the Wagner card) in specialized facilities, puts them on “roadshow” when possible, and still treats them like financial instruments, not timeshares.
18:11 – Why collectibles can belong in a portfolio. Rob traces the evolution from “equities are too risky” to REITs, crypto, and now alts-on-alts — and why finite, tangible items appeal in an increasingly intangible world.
22:08 – Should you just follow your passions? Rob’s nuanced advice: start with what you deeply understand, but target blue-chip, historically resilient examples (the “firsts,” the best grades, the true one-of-ones), not just whatever looks cool.
23:28 – Gen Z’s love for max variance. A contrast between younger investors who chase 30–40x outcomes and are oddly okay with losing everything, versus wealthier, patient investors gravitating toward compounding blue chips.
29:06 – Fighting the 24/7 hustle trap. Rob talks candidly about never really taking time off, how fundraising and layoffs take a toll, and his current goal of making weekends sacred again.
31:36 – Advice to his younger self. Why chasing what you think will make money is less powerful than going all-in on what you genuinely care about — and letting that become a business.

Episode Summary

In episode 19 of Making Sense of Your Money, host Dan Pascone sits down with Rob Petrozzo, co-founder and Chief Product Officer of Rally, to explore a surprising blind spot in many high earners’ portfolios: the world of high-end collectibles. While most professionals think in terms of stocks, bonds, private equity, and maybe some real estate, Rob’s firm gives everyday investors access to the kinds of assets that used to live exclusively in private vaults and museum collections.

Rob describes Rally as a “stock market for collectibles.” The company sources museum-grade items across categories—classic Porsches, rare Rolexes, first-edition sports cards, dinosaur fossils, historic documents, even premium domain names—and turns each asset into its own mini-company. Using SEC-qualified Regulation A offerings, they place the asset in an LLC, issue shares, and run an IPO inside their app, allowing investors to buy pieces with relatively small minimums. Afterward, Rally operates a secondary market where shares can trade, offering liquidity that traditional collectors often lack.

Valuing one-of-a-kind items isn’t as simple as pulling up a ticker symbol. Rob details the process: auction and insurance comps, a structured 24-point checklist, expert input from specialists and auction houses, and a “relevance score” that captures cultural heat and long-term interest. A Stegosaurus skeleton, for example, may have only a handful of historical comps, but it also taps into a lifelong fascination shared by millions. That blend of data and narrative is key to pricing and investor appetite.

Dan presses on how Rally fits into a broader wealth strategy. Rob argues that collectibles can be seen as “alternatives to the alternatives” — a tangible, finite complement to private equity, real estate, and other non-traditional holdings. He emphasizes that the goal isn’t to speculate on every fad; it’s to focus on blue-chip examples that have weathered multiple cycles and show persistent demand, like iconic sports cards, cornerstone vintage cars, or historically important watches. For sellers, Rally offers a hybrid: they can sell part of their stake to unlock liquidity while keeping a meaningful equity share that participates in future upside.

The conversation eventually turns personal. Rob shares how an early fixation on money led him into hustle-at-all-costs mode, building Rally through intensive fundraising rounds and emotionally taxing decisions like layoffs. Over time, he realized he’d sacrificed weekends, relationships, and mental space. His advice to his younger self—and to ambitious listeners—is to avoid chasing opportunities purely because they “might make money,” and instead go deep on what you care about and are good at. With today’s tools, he believes passion plus competence can become a powerful business, and the money often follows.

Full Transcript

Dan Pascone: Brought to you by Tailored Wealth, helping business leaders live their version of a rich life.

Dan: Welcome to another edition of the Making Sense of Your Money podcast, where we cut through the financial noise and help business leaders to make smart, confident money decisions. Welcome to another episode, episode number 19 of the Making Sense of Your Money podcast.

Dan: I am your host, Dan Pascone. I am the founder and CEO of Tailored Wealth. And each episode features a trusted voice in the financial world, someone who works directly with high-level professionals to simplify the complex and turn strategy into action.

Dan: And I’m really pumped about today’s guest. We’ve got with us Rob Petrozzo, who’s the co-founder and Chief Product Officer. And Rob and his team deal in fine arts and collectibles. So I’m really interested to learn a little bit more about this space. Thanks for joining the Making Sense of Your Money podcast, Rob. Pumped to have you.

Rob Petrozzo: No, likewise, man. There’s no one I’d rather be talking money and collectibles with than you on this beautiful day in New York.

Dan: Very good. I love it, man. I love it. My last guest had a Yankees hat on. So hopefully the Yankees can start playing a little bit better, but that sounds good.

Dan: So, we’ve got a lot to cover. I know our audience wants to hear all about what you do, and this is a really, really interesting space. So if you don’t mind, just give us like a 90-second overview of what you and your team at Rally do, who you serve, and maybe a little bit of background on how you got into the space.

Rob: Yeah. So, at its most basic level, Rally is essentially a stock market for collectibles. And when we think about collectibles, we’re not just thinking about the baseball cards in the attic. It’s everything that you would kind of see in a museum— all the museum-grade, investment-quality collectibles that we really treat as assets.

Rob: They’re all the things that the wealthy have been buying and holding on to and making money on for generations, but they really have been kind of behind the velvet rope for the majority of the people who care most about it—for retail investors, for high net worth investors, for everybody who’s not buying it in bulk and doesn’t have the connections to get it.

Rob: So what we do is we take individual assets—everything from classic cars, which is where we started, up through watches, wine, whiskey, sports memorabilia, game-worn jerseys, up to dinosaur fossils, even intangible assets, things like four- and five-letter domain names. We’ll take those, we turn them into stock, and we run our version of an IPO.

Rob: We do that all within the app. We do that with hundreds of thousands of investors, all age groups. We do that with minimums as low as $10, but we also have investors who will invest tens of thousands of dollars in any individual asset. We do that pretty regularly.

Rob: And then we run a secondary market for all those assets where you can kind of trade your shares and get liquidity. Along the way, we’ll do things like—we had a museum pop-up here in New York, we’ll sell individual assets at auction, make sure they can kind of realize gains along the way.

Rob: But really our main focus for the better part of the last seven years has been finding the most interesting, most valuable assets in the world and opening up real equity, real access to those assets to the people who really care about them and love them.

Rob: And now with, you know, over 400 individual assets on the platform, a bunch trading in all different directions—things that go back as far as a Declaration of Independence all the way up to, you know, the NFT craze. We had a bunch of the best NFTs on Rally as well. So whenever you have a market that really cares about something and an asset that represents that group, that’s something you’ll typically find on Rally and be able to sell, buy, and trade the same way you would stock.

Dan: Super, super cool and interesting. All right, so I’ve got a ton of questions, so let’s dig right in.

Dan: First off, tell the audience a little bit about the valuation process on these assets, right? I mean, our audience understands how stocks and bonds are valuated, but tell us how some of these sort of rare pieces are valued and then ultimately what’s the trading process like on your platform?

Rob: Yeah, so when we do valuations early on, when we’re first acquiring an asset, it’s not that dissimilar from the standard IPO process. Typically we’ll have a bunch of auction comps, we’ll have insurance comps, we’ll have a range that we’re comfortable in for an individual asset.

Rob: A lot of times we’re finding one-of-one assets, so it’s a little bit harder. At that point what we’ll do is—we have a huge network of experts in our space, every auction house we’ve dealt with along the way, every broker, every dealer, international buyers and sellers. We always have a good feel for a market that we go into.

Rob: Once we find an individual asset, outside of just those comps and the auction results, we have a little bit of a relevance score that speaks to whether or not that asset’s in conversation. And we apply kind of a 24-point checklist that we have for every asset that has everything from the rarity, the provenance, the individual comps, auction sales, insurance-adjusted values, and then we add on those layers of relevance scores.

Rob: And that’s whether or not it’s in a liquid conversation, whether or not that asset class is something that’s withstood the test of individual sort of economic ups and downs along the way.

Rob: So when you look at something like a Stegosaurus skeleton, which is something that we have that we just IPO’d relatively recently—it was still in the ground when we found it—and we’re working with some of the best paleontology and geologists in the world, finding that asset, acquiring it, mounting it, and bringing it to auction. There’s only been probably seven or eight individual Stegosaurus sales over the course of the last, call it, decade. Most of them are in museums; very few were in private collections.

Rob: There was a $44 million sale, the most recent one at Sotheby’s that went to Ken Griffin from Citadel. And that’s something that kind of set the benchmark of Stegosaurus skeletons. That was a little out of whack, so that one is something that even though it’s part of this IPO process and part of the valuation, it’s one that we treat as an outlier the same way you might if you were valuing an IPO and seeing individual comps in the space that were trading at some crazy number relative to book value.

Rob: So we’ll take all these kind of metrics, but something like a Stegosaurus, which is in conversation now because of that sale—bones and dinosaur bones in general are part of this polarizing conversation between the science community, museums, and individual collectors. It’s something that we learn about when we’re in fifth grade. You think about it, it keeps popping up throughout the course of your life. That’s something that has a value, and that relevance score for a Stegosaurus, as an example, is very high relative to other dinosaurs and especially to other asset classes.

Rob: So we’re factoring all those individual pieces. We’ll get this formulaic approach, we’ll layer on some intuition, and we’ll layer on that relevance score, and it leads to a range for an IPO in a very similar way that you might price an IPO of a company.

Dan: Super interesting. All right. So let’s talk a little bit about the process and the mechanics behind all of this. How does Rally—how does your team find maybe a Stegosaurus skeleton—might be a bad example because that’s super rare—but how do you find these types of assets or how do the owners of these assets find you?

Rob: Yeah. So we’ve developed a really great relationship with the collector community and with a lot of the biggest auction houses in the world. And I think early on, when we were kind of raising money early and thinking about how we were going to build this platform out with these assets and how we were going to find them, we were kind of just coming to the table with money and grit and just showing up at auctions, trying to make as many relationships stick as possible and talking to as many sellers and buyers as we possibly could to really not just understand the space, but to get the ins into where these assets came from.

Rob: As we started building out our advisory board, some of the brokers that we work with, we really kind of mobilized a team of people who are really well known in each space and brought them into the company. And whether that was through advisory deals and a little bit of equity or whether it was just establishing relationships where we took a real interest in some of these asset classes, we made sure that the relationships were extremely strong before we started asking for things.

Rob: So it really took two or three years to build out a lot of these relationships before it was time to find an asset in a specific vertical with a group or with a person that was really comfortable with us at that point too. And that kind of paid dividends. As we built out these individual verticals one at a time, starting with cars, we were literally flying all over the world meeting as many people as possible who really wanted to show us the vehicles they had and talk through it.

Rob: I think that was kind of the keystone in the way we developed those relationships. We went into asset classes that we really cared about. We weren’t just showing up and thinking about it as a binary outcome where it’s pure finance—we’re just trying to make as much money as possible. It was things that we cared deeply about. They were stories that we really cared deeply about, and there were people who wanted to tell those stories to us who happen to have the inroads to the best examples of the stuff we were looking for.

Rob: So now, six, seven years later, we’re at a point that those relationships have come full circle. We’ve done business in every single asset category with all the biggest names. But we also have something that’s very interesting to some of these asset sellers, who now come to us where instead of going to an auction platform, paying a 20% premium, doing something where you’re signing a one-year deal where you can’t shop it anywhere else, hoping that the right people show up at auction—we’re in a position to price that IPO and tell you exactly what we believe it to be worth.

Rob: We have all of our investors in the app kind of lined up to make that purchase so you know it’s going to sell. And then at the same time, if you want to keep some of that equity—which a lot of our asset sellers and consignors do—you can maintain 20 or 30 or 40% on the books for yourself so that as the asset continues to increase in value, you got some liquidity out of it, but you didn’t have to get rid of and sell every single share or every piece of the equity that you own in it.

Rob: So we’ve done that with some of our biggest assets. We have a Honus Wagner card, which is one of the most famous baseball cards on Earth. It’s never sold for less than it was purchased for. So when we got ours, it was a $600,000 deal, which now is—you know, that was four or five years ago; now you’re not touching anything for less than 1.5 million on that card.

Rob: The owner had had it for a long time, made a bunch of money on paper, but wanted some liquidity. So he maintained 50% of the card. We bought the other 50%, securitized it through the SEC, ran the IPO, and now it’s trading close to $2 million. So he still participates in the upside with the community that cares about it most.

Rob: So those dynamics have been really interesting and really attractive to a lot of asset sellers and consignors as well.

Dan: Super interesting. So, I happen to know a little bit about this—my son and I are baseball card collectors. So I happen to know about the Honus Wagner card story and I’ve watched a few programs and seen a little bit about how that works.

Dan: Who’s the guy that has a show on Netflix and it’s all sports memorabilia?

Rob: Yeah, exactly. I watch his show a little bit.

Dan: So let’s use that example. It’s super interesting that you can kind of get some liquidity but still keep ownership and securitize. So walk us through the mechanics of that. I own a Honus Wagner card. I come to you and I say, “I want to sell 50%.” Are you then splicing that other 50% into shares that other people can buy? What does that look like?

Rob: Yeah, funny enough, that card—that actual card—came from an introduction from Ken Goldin. So that’s actually a good example to use.

Rob: That card, as an example, was something that checked every single box for us in terms of the relevance, value, something that has a history of returns. We knew that that was a card we wanted and we were going to launch the trading card vertical on Rally with that card.

Rob: So when we found it, it took a little time to explain to the owner what we were actually going to do with it. What we do is we essentially take that card and through what’s called Reg A—it’s an SEC-compliant method of kind of creating a stock out of an asset. It came out of the JOBS Act, which was really pushed toward crowdfunding.

Rob: So we do it in a way where the IPO is kind of similar to a Kickstarter or an Indiegogo—raising money from a group of people for an asset. So what we’ll do is, we’ll take that card, we essentially incorporate it; it becomes an LLC. So now it’s Honus LLC.

Rob: Within that LLC, it owns and operates one asset, which is that card. We take that whole thing, submit it to the SEC with a price on it, a value range that we’re going to do the IPO at, a number of shares that we’re going to issue for that asset, and then we open it inside the app where we go through the same thing you would if you were investing in a new brokerage app.

Rob: You go through the know-your-customer KYC, AML, you give us name information. That all goes to our third-party broker who kind of does the quick “you are who you say you are” check. Then you’re in, and it’s very much at that point a financial instrument. It becomes the equivalent of a share in the company that owns and operates that one asset.

Rob: And throughout the course of the life of that asset when it’s on the platform, we go through all the same accounting, all the same compliance submissions, everything you would for a regular company. It kind of looks and feels—if you go to the SEC website, you could search for Rally and see all 400 of these assets. They’re all individual stocks that live through the SEC site. You could see every detail about it. It’s got every instance that could affect the value of that card. It’s got the trading values.

Rob: It’s got every sort of—quarterly, we’re required to submit all this information and we do that in such a way that it really does mimic everything you would see from an equity from any asset that would go public, any stock that would go public and trade on an exchange over the period of anywhere from a couple of years to in perpetuity.

Rob: We’ve done that in such a way that was kind of very unique when we started this, and we did kind of create a blueprint for a lot of other companies who fractionalize assets to follow. Because once we did it once that first time, even though it was very unique, now it’s very templatized in such a way that we’re really plugging in the asset, the value, the number of shares we’re issuing, and a date range of when it’s going to go public. From that point forward it trades very much like a stock would and we’re required to submit all the information that a regular company would that trades on any normal stock exchange.

Dan: Super cool. Couple questions on that. Conceptually, how many individuals can have ownership in a Honus Wagner baseball card?

Rob: Yeah. So the one that we have, I believe there’s 600 owners right now. And that’s everything from an 18-year-old who was collecting with his dad when he was younger and put 100 bucks into it, all the way up to individuals who have tens and 20 and $30,000 positions that they’ve developed over time.

Rob: So that’s kind of the beauty of what we’ve tried to build, and the concept around democratization of assets and democratization of finance, which everybody has used as kind of a buzz term forever. In our mind it meant that somebody who knows every single detail about this card, but isn’t in a financial position to spend a million dollars on it, can have the same access as somebody who really collects these equity slices more as an investment than as a collector but cares maybe just as much from their own position.

Rob: And I think that for us has always been the really important part of it, and that’s why you get this really diverse mix of people on Rally, and sometimes thousands of individuals in an asset who all care deeply for their own reasons, but they’re all kind of pooled together. We’re doing something really different and really unique.

Dan: So this may be a stupid question, but where is the card? Who has the card?

Rob: Yeah. So that’s actually the best question. That’s the one that, when we first started, I thought more people were going to ask: “Where is the card and prove to me that it’s real.”

Rob: But I think part of us having to do this in a way that’s not like crypto and it’s not memecoin—it is a real thing that has real compliance and is attached to a real submission with the SEC and real qualification—was the check mark that it really exists.

Rob: And I think that for us, that card in particular has been on a roadshow essentially for three or four years. We had it in our museum in Soho for the better part of a year last year. We’ve had it on display in LA at different conventions and different events. That card kind of lives at all times in our warehouse in Delaware, where it’s under 24-hour lock and key with a lot of our other really high-value assets in a purpose-built facility where a lot of really expensive art and other collectibles live as well.

Rob: But these are assets that whenever we can bring it out and show people, especially investors, what it is, let them hold it, have a conversation around it—we always try and do that whenever possible. And we’ve been really lucky that, with cards in particular, it’s not like moving a car around or the Declaration of Independence that we have, too, where it requires—it’s huge and it requires a very specific type of security and a very specific type of insurance.

Rob: That card is portable enough that in the right setting we can kind of bring it to life and do some really good storytelling around it at events and in person.

Dan: So, for the average investor that wants to invest—and we’ll stay with the example of the Honus Wagner card because I know how big of a deal that is—if I own $500 worth of that Honus Wagner card, what do I get other than being able to tell the story, which I get is pretty cool? What do I actually get from that? Is there a certification or what goes into that?

Rob: Yeah, with that card actually there was a full stock certificate. We’re trying to mimic what the stock market was. I think when I was younger, we’re trying to do something like—when I was a kid, I don’t know if my grandma or someone gave me like a share of Disney, and there was no E-Trade, Robinhood, Public; none of those apps existed obviously at that point.

Rob: So it was reading the price in the paper the next morning in like the ‘90s. But getting that stock certificate did mean something. It meant that I was part of something. And I think that we tried to mimic a lot of that with all different merch and collectibles that go with it. We’ve minted a lot of stuff from scratch for that card in particular. We’ve done a bunch of real tangible pieces that go with it.

Rob: But we also want to make sure that we’re keeping it real too. We’re not in a situation where we’re going to do a timeshare with the card. We don’t want to have that be in somebody’s house outside of security, outside of the construct of what we’ve built. So we do want to treat these—as much as they are museum-quality collectibles—we want to treat them as the financial instrument that they’ve become as well.

Rob: So our goal is to maintain and to own the best examples of these pieces. A lot of times that means it’s going to live in your portfolio, but not necessarily in your pocket ever. It’s something where—Honus is a tough example because it is such a one-of-very-few. There’s only 50 or so in the world.

Rob: But when you think about something like Michael Jordan rookie cards or some of the stuff that’s a little bit more populous, we might have the PSA 10 highest-graded, most pristine example on Rally. But that doesn’t preclude you from owning a lower-quality version or something similar that’s part of your personal collection that you have in your hand, that you could take out of the drawer and hold and have.

Rob: So we’ve always looked at what we’re building as the best examples, the ones that truly are investments that we need to maintain for future generations. Those live on Rally. There are similar examples, lower-graded examples or ones that you can have without having to spend hundreds of thousands of dollars that a lot of times our investors do have in their personal collection, but they know that this one’s maintained in their portfolio. They see it digitally in their portfolio, but it’s something that’s part of an investment thesis for the future.

Dan: Got it. Okay, let’s continue on this thought. We’ve got a lot of listeners and viewers that are comfortable and come to us to learn about investing and growing their wealth, and they’re familiar with investing in stocks, bonds, and even maybe private companies.

Dan: Help our listeners and viewers understand what makes a collectible-type investment a good investment, and how do you actually build your wealth? And then maybe we can start to get into the conversation of how does something like this potentially fit in an overall portfolio.

Rob: Yeah. I think that a big part of it is what I personally, myself and my partner Chris, we talked about early on. When we were growing up, we were kind of taught that investing is very much this zero-sum game. It’s just make money and take emotion out of it as much as you possibly can.

Rob: But in my mind, and the way I’ve seen the new generation of investors develop, emotion is a tool. And I think that emotion doesn’t just mean I see something and I have a snap judgment; I care about it immediately and I want to grab it and hold on to it and then I don’t care afterwards. It’s not just this moment.

Rob: It means that you have a deep passion and most times a deep understanding of what this asset and what this thing actually means. That to me is an advantage, where if you can see around a turn and have a real emotional connection to something where you’ve paid attention to it from the inception—the first time you saw it, the first time it came out—all the way to now, where maybe you have a little bit of money stashed away, maybe you have index funds, you have a 401(k), but you’re not necessarily looking to pick stocks. You want to pick the things that you know best.

Rob: I think this is the place that you inevitably end up. And we want to get ahead of that by creating a world that celebrates that and allows you to put your money where your mouth is.

Rob: So when we think about the future and I think about where assets are now, there was a time when equities were looked at as too risky for a portfolio. And then REITs were looked at—“No, don’t invest in REITs, that’s way too risky. It’s this alternative asset.”

Rob: Then we saw it recently with the cycle of crypto that we’ve been in for the better part of the last 10 years, where you had people like Jamie Dimon and others coming out and saying, “This is magic dust. It’ll never happen.” And now they all have trading desks and it’s all part of a huge portfolio that their individual investors and LPs and everybody asks for. So at a certain point you have to do it and have to open it up.

Rob: We’re trying to get ahead of that with alternatives, where it used to be 1 to 2% of your portfolio. Now you’re starting to hear 5%—even up more, certain managers are saying allocate more money toward alternatives. We’re trying to find the alternatives to the alternative.

Rob: Not just real estate, not just art. The next tick up for us is going to be these assets that have— you know, they meet all the investment criteria you want: a very finite amount that exists, they’re not making any more; a tangible asset, something that’s akin to gold. Even though gold doesn’t necessarily back the dollar anymore, it’s still something where you see it right now—that’s what people think about as the hard asset. But all of these we look at as hard assets as well.

Rob: It’s something that we feel has the ability to grow and outpace funds and outpace individual indexes, which a lot of these have proven to do, both individually and as a basket of assets over the course of 10, 20, 30 years.

Rob: So I think that we’re at that inflection point right now where everybody’s looking for something a little bit different. And also you have enough data on a lot of these assets that goes back 20, 30, 50, sometimes 100 years—like the Honus Wagner card—to say that it’s proven itself to this point enough for me to put this into a portfolio.

Rob: And we think about where the future is going. In my mind, it’s going towards intangibility. I think there is something nice still about having a real something where it’s not just backed by an idea. There’s an element, there’s an asset, there’s something I can actually hold and trade.

Rob: And it also has that bit of nostalgia too, which sometimes isn’t always—you know, it can be toxic. It’s not necessarily the best thing to use as an investment thesis, but it checks all the points and has that nostalgic, good feeling about it. That to me is a place that I’m comfortable putting my money, and I’m comfortable having my money there through periods of uncertainty or volatility that you might see in the equities.

Dan: Love it. You know, we talk to our clients a lot these days about investing in alternatives and where they have a fit in the portfolio, but I love your concept—I’m going to use that. These are the alternatives to the alternatives. I’m going to use that. That’s a great phrase.

Rob: We’re trying to see around turns, man. Everybody’s trying to find the next thing. And sometimes it’s right in front of you. Sometimes it’s something you remember from childhood and you know it so well.

Rob: We have 17- and 16- and 15-year-olds who used to come to our museum space. They would walk in and see a 1955 Porsche Speedster—it was the first that we had. They would know every single detail about that car, and it’s a car that came off the assembly line 50 years before they were born.

Rob: That means that they have a well-formed investment thesis that they’re about to really get into without even realizing it in three or four years when they’re starting to put their money together.

Dan: On that note, would your advice be to—let’s put ourselves in the shoes of an individual who’s got money in different markets, they’ve got a well-diversified portfolio, they’re high-income individuals like a lot of the folks that follow our content and a lot of our client base, and they want to start to invest in, let’s call your phrase, alternatives to the alternatives.

Dan: Would your recommendation be: follow your passions and invest in the things that you’re most interested in? Or how would you go about that thought process?

Rob: Yeah. I mean, my lawyers would say never say this is financial advice, but I’ll give a little bit of it.

Rob: I think it’s easy to look at something and fall in love with it and want to own it. And like a Porsche is such a perfect example. A Porsche, Rolex, a bottle of like Petrus—like you think about these things that truly are the trappings of wealth. And when you get to a certain point and it’s new money especially, those are typically the first things you go for.

Rob: But I think that we’re at a point now that, especially with the high net worth individuals on Rally, they have something that I think the younger generation doesn’t, and that’s patience. And I think that with patience and the ability to compound over time, you look at kind of the blue-chip things a little bit more.

Rob: Those are things like the first of the 1955 Porsche Speedster or the first Rolex Daytona with the Zenith movement. There are all these pieces that—you can look at the thing you care about, and then if you do deep enough research, that information is so available now about what the best version is, the earliest version, the one that’s done the best over time throughout multiple market cycles.

Rob: Because I think that what those individuals have, and we see it so much on Rally, is that Gen Z right now prefers highest-variance outcome. They’re completely okay losing every single dollar and getting some of the financial clout out of posting that on Reddit or putting it on Instagram and showing “I just lost my life savings in a day. Haha. All right, I’ll get it back.”

Rob: And they’re okay doing that if they 30x or 40x once. I think that as I’ve gotten older, I’ve realized that having that patience that comes with a higher net worth is something that I want to get to earlier in life. And I think some of the smartest Gen Z kids are starting to get to it a little bit earlier too.

Rob: You find that in these blue-chip assets. There are things like dinosaur fossils in the best condition that are 80% bone volume, or the 1955 Porsche—that’s the first example that led to the modern Porsche that every new-money individual chases now and wants to get. When you find those, that’s a place to not just park money, but that has the opportunity to show outsized returns if you have a little bit of patience. The blue chips, the first versions of, and the ones that truly are one-of-ones.

Dan: Super interesting. Very cool. That’s fascinating stuff. Thanks for sharing that.

Dan: All right, we’re going to switch gears a little bit. We’re going to get to know Rob a little bit more. So I’ve got a good idea of your business. Now we’re heading into what we call the lightning round, all right?

Dan: The lightning round’s a lot of fun. Only premise here is: just give us the first thought that comes to your mind. Could be a one-word answer, could be a drawn out thought, whatever makes sense.

Rob: Dude, story of my life. Unfortunately, I talk before I think most of the time, so you got me.

Dan: We are likewise in that regard for sure. All right. Coffee or tea?

Rob: Coffee. At this point too, as you get older, it becomes more—it becomes darker and darker and darker to the point that it’s just like black cold brew at this point. Like, you become an older, callous individual. It’s always been coffee.

Dan: You’ve got to eat one meal every day for the rest of your life. What is it?

Rob: Oh man, I mean like pasta’s in my DNA, so there’s always some form of pasta. Particularly there’s one from a restaurant called Frankies in downtown Brooklyn. I actually had this conversation two nights ago. That’s my last meal. It’s a cavatelli that they do that nobody else does. But pasta for breakfast I could do if I really need to.

Dan: Yeah, with a name like Petrozzo that checks out.

Rob: Yeah, I’m wearing it on my sleeve, man. Unfortunately I take it with me.

Dan: Another thing we have in common there. All right. What’s one tool or piece of technology—it could be hardware or software—other than your computer or your phone that you can’t live without?

Rob: Man, other than computer, phone that I can’t live without… You know what, I’ll be honest. I think there’s analog cameras—are something that I’ll always gravitate towards. And I think that there’s also even the newer Leicas that are digital. There’s a world where I feel like that’s always going to exist and I always, every three or four months, go back to it and just walk outside and take pictures.

Rob: I’ve realized that I’m more connected to—even though it’s not truly technology—I’m more connected to analog cameras than I ever have been over the course of the last two, three years. I don’t think they’re going anywhere.

Dan: Super cool. Favorite quote or phrase about money or success?

Rob: Oh man. You know, this is an Eric Hoffer—he’s like a workman philosopher—quote, but it’s one that translates to everything. It’s a saying I’ve always used for creativity and I overuse it, but for finance in particular, kind of what we were just talking about, is that “learners inherit the earth, while the learned find themselves beautifully equipped to deal with a world that no longer exists.”

Rob: And there’s nothing that’s ever been more true, especially right now. As we move towards AI, as we move towards more digital methods of communication, as you see kids on their phone all the time. I remember when I was younger and email was kind of new and there was a whole group of people who were like, “Nah, I don’t send emails. That’s stupid. I do it in person.” Those are the people that get left behind, and I don’t mean that in a negative way. It just means that you’re not going to be open to new things that are happening around you and you’re going to miss the opportunity to find something new that really intrigues you and makes you happy.

Rob: So I think that’s a big one for me.

Dan: Learners lead. Love it.

Dan: Do you have a favorite book on finance or business?

Rob: Do I have a favorite book on finance? I don’t think I do. There’s a book that’s finance-adjacent that I haven’t read in a long time. It’s super thin and people should read it. It’s called The Fred Factor, and it’s about a mailman who found so much joy in the day-to-day and having these conversations with all these people from different walks of life and having it lead him down kind of a pathway that he didn’t expect to go down.

Rob: That to me is part of my financial thesis lately, especially—I’m talking about the last four or five years and after COVID and kind of through now. You’re not going to find out what’s happening around those turns unless you have different conversations with different people. Because if you get stuck in the same conversations, the same bubble, it becomes that echo chamber and you do miss, especially when it comes to finance, you miss those opportunities.

Rob: So when I think about alternative assets and the world we work in, I was never thinking about anything like investing in domain names as a thing. That to me was like, when I was younger, I was trying to buy a bunch of domain names—like I might make money one day, but no one makes any money. But you start talking to people in that space and they’re so deeply passionate about it and they have so much knowledge to unlock.

Rob: So that to me is a book I read when I was like 12, 13 years old that unlocked that idea.

Dan: Do you have a personal hack you can share?

Rob: You want to know one? This is so ridiculous. I actually had to explain it to somebody two days ago. Every time I start something new, I do like a little bit of a countdown in my head like I’m in a gym. That goes from everything—from getting out of bed to jumping on a call to jumping on this call.

Rob: It’s like, “All right, it’s like a 1, 2, 3 and it’s like, all right, go.” And then in my mind that triggers this kind of sprint towards an end goal that I’ve accidentally used in every situation that requires a restart for the last decade. I’m trying to actually do less of it because I feel really corny even telling you that.

Dan: I like it. I think I’m going to give that one a shot. I like it.

Rob: That’s been my hack. I’m pretending everything is like a sprint and I’m sort of in the gate about to start, and then after the countdown starts I have to go the same way I would be at a gym if a trainer was yelling at me.

Dan: Shotgun goes off and we’re ready to sprint. I like it.

Dan: What’s one milestone personally or professionally that you’re working towards?

Rob: Man, I’m trying to find a way to make weekends weekends. I think that what happens when you’re head down on a business—and we’ve been doing it at Rally for the better part of seven years. I did one actual vacation in 2018 or 2019 after we raised our Series A because it felt like there was a way to breathe out for that moment. But even on that vacation, there was no way to stay away from email or computer or whatever.

Rob: I think finding time on weekends—the hustle culture was so glorified pre-COVID especially, and it turned into something where it takes over your life if you let it. Then your only purpose, your only identity is tied to your work. I found myself doing that and I’ve still found myself doing that for the better part of half a decade.

Rob: I’m trying really hard to find some peace and get away from it and have weekends actually be weekends. That’s—when you’re a young founder, when I was in my 20s, it was a little bit different and you could just power through weekends and open a computer at 7:00 in the morning and still sort of get some of your day back.

Rob: There’s a time and a place for hustle. I’m just trying to find peace at this point. I think everybody—a founder in my shoes who’s gone through a bunch of rounds of fundraising, a bunch of ups and downs along the way—you know, building a team, laying off a chunk of the team, building the team again, it really does weigh on you. I’m starting to realize that it affected so many relationships in my life.

Rob: So I’m trying to get some time back to get away from it and actually leave work at work on some weekends.

Dan: Well said, man. I can relate to that for sure. I think any entrepreneur can.

Dan: What’s one bucket list item that you’ve already accomplished?

Rob: Man, you know what? This is a little bit of a cheat and it’s a broad stroke, but there’s a lot of people that I worked with in a past life or really respected a ton. And when we were raising money the first couple times around, I was able to connect with those people, have them what I felt like treat me like a contemporary and like someone that was kind of on their level.

Rob: These are people that in business and music and a bunch of different places I just always held on this pedestal. To be able to have those type of conversations about what you’re working on and see those people excited about it and have them kind of put their money where their mouth is and invest in what you’re working on and invest in you was something that was almost shocking the first couple times that happened.

Rob: And now I look back at our cap table and think about some of the relationships that I’ve developed over the last six or seven years, and they all came from this place where I was able to have real conversations with people that I was idolizing and I put on this pedestal, who cared enough about what I was doing to kind of put their money where their mouth is.

Rob: That’s a little bit in contrast to what I just said about leaving the business behind and having regular relationships in real life, but it was something that at the time, and even now, is still shocking to me that that was able to happen.

Dan: I love it. That’s probably a good segue into my last question, which is: what advice would you give to your younger self?

Rob: You can’t take anything too seriously. That question is one that I thought about—I think about myself when I was like 20, 21. I was getting out of school and money was all that mattered. And even now, to a certain extent, I think about everything in terms of money.

Rob: But what happens is you start doing things that you think are going to make money and not things you actually care about, when in reality the byproduct of doing things that you care about is that you’re able to turn it into a business and make money. I think I really messed that up early on in life and made a little bit of money and was able to kind of parlay it into a real career.

Rob: But in reality, so much of that stuff wasn’t necessarily contributing to my health, my happiness, my relationship with my friends and family, the people around me. Doing the things that you care about, especially when you’re younger, opens up the door to whatever your career will be.

Rob: And especially now, where creating—and you know this as good as anybody else—the business side of your business is only going to go as far as your ability to sort of tell the world about it and do it in a unique, entertaining way. A lot of times that’s going to contribute to the outcome in a really significant way.

Rob: When you see all these kids come out of school or these kids just start making content, designing stuff from scratch, building out clothing lines, doing stuff that I never dreamed about doing when I was younger—they have all the resources to do it. You’ve got to really care about what you’re doing. It will turn into a business.

Rob: I think I was chasing a lot of like, “All right, I’m going to do X, Y, or Z because it’s going to make me some money at some point. I could turn it into a business,” instead of saying, “I really care about this. I’m pretty good at it. I should go down that pathway.” I think that was a little bit of a mistake that I was able to correct.

Dan: Great advice for any young entrepreneurs out there, for sure.

Dan: All right, and then finally, Rob, if our listeners want to connect with you, collaborate, follow you, get involved with Rally, what’s the best way to reach out to you and what’s the best way to find you and your team?

Rob: Yeah, we’re @rally on Instagram and most platforms. We’re on RallyRD, and then you can go to rallyrd.com, rallyroad.com. I’m @robpetrozzo on every platform, and any concept, any idea, anything that we’re talking about, any feedback—I’m always down to have that conversation through DM.

Rob: Half the platform on Rally—half a million users—have my cell phone number. They text me all the time. We talk about what their needs are. So I’m always down to have that conversation. Would love to talk to any of your listeners, anybody who has an idea about what the future of finance looks like. Those are the best conversations.

Dan: I love it. I’m sure you’ll get some of our audience that takes you up on that for sure.

Dan: So thanks so much for sharing your time and insights today. This was a super cool conversation.

Dan: That’s it for the episode. As always, keep your strategy sharp, your goals clear, and your money working as hard as you do. Cheers everybody.

Resources & Citations

Modern Portfolio Theory & Diversification. Foundational frameworks on risk, correlation, and why adding low-correlated assets can improve a portfolio’s risk/return profile.
Academic work on collectibles as investments. Studies examining long-term returns of fine art, classic cars, wine, and rare stamps/cards compared to equities and bonds.
Overview of Regulation A Offerings. SEC guidance on how Reg A and Reg A+ allow companies to offer fractionalized ownership of assets to a broad investor base with specified limits and disclosures.
Alternative Investments & Portfolio Construction. Practitioner guides discussing appropriate allocation ranges and liquidity considerations for alternatives within high-net-worth portfolios.
Behavioral Finance & Emotional Investing. Research on how passion, familiarity, and overconfidence can both help and hurt investment decisions—and how to channel emotion productively.

FAQs

How much of my portfolio should be in collectibles or “alts on alts”?

There’s no one-size-fits-all answer, but many high-earning investors start with a small slice—think low single digits of net worth—allocated to collectibles and experimental alternatives, especially when liquidity and pricing are still developing. The exact percentage should reflect your risk tolerance, time horizon, total net worth, and how secure your core plan (retirement, emergency reserves, tax strategy) already is.

What are the biggest risks with investing in fractional collectibles?

Key risks include valuation uncertainty (especially for unique items), liquidity risk (your ability to sell shares quickly at a fair price), market sentiment swings, platform risk (the health of the company facilitating the investment), and concentration risk if you put too much into a single asset or niche. Unlike broad index funds, you’re often betting on specific pieces and on the long-term demand for that category.

How does Rally decide which assets to bring onto the platform?

Rally looks for museum-grade or investment-grade pieces with strong provenance, limited supply, and a documented history of collector demand. They use auction comps, insurance values, expert input, and a structured checklist to evaluate rarity, condition, and cultural relevance. The goal is to focus on “blue chips” within each collecting category rather than speculative or fad-driven items.

Do I ever get to physically hold or see the assets I invest in?

Investors don’t typically take assets home (they’re stored in secured, insured facilities), but Rally periodically exhibits items through pop-up museums, events, and conventions. In those settings, investors and the broader community may be able to see key pieces in person, similar to viewing a company’s product in the real world even if you only own its stock.

How are gains on collectible shares taxed?

Tax treatment can be nuanced and may depend on factors such as holding period, the structure of the offering, and your jurisdiction. In many cases, profits may be treated as capital gains, and higher rates can apply to certain collectibles under U.S. tax rules. Because situations vary, it’s wise to involve your CPA or tax advisor before committing significant amounts to these assets.

Is it better to follow my passion or stick to “blue chips” I don’t care about?

Ideally you do both: start with categories you genuinely understand and enjoy (cars, watches, cards, art, etc.), but within those categories aim for the pieces that have stood the test of time—first editions, best grades, historically important examples—rather than chasing every shiny new trend. Passion can help keep you engaged and learning, but discipline and patience are what turn excitement into long-term results.

Disclaimer

This episode and page are for educational and informational purposes only and do not constitute financial, tax, legal, or investment advice. Investing in collectibles and alternative assets involves significant risk, including potential loss of principal, illiquidity, and pricing uncertainty. Always conduct your own due diligence and consult qualified professionals—such as a financial planner, tax advisor, and attorney—before making decisions about portfolio allocation, participating in private or fractional offerings, or changing your investment strategy.

Next Steps

If you’re a high-earning professional or business owner, there’s a good chance your “diversified” portfolio is still heavily tilted toward a few familiar asset classes. Take 30–60 minutes this week to map out your true exposures—public markets, real estate, private equity, employer stock, and any existing alternatives—then ask where carefully chosen, tangible collectibles might complement what you already own rather than replace your core plan.

When you’re ready to think more strategically about alternatives—how much, which types, and how they fit into your broader tax and retirement roadmap—explore more episodes and guides at Making Sense of Your Money, or see how Tailored Wealth partners with equity-rich professionals and entrepreneurs at yourtailoredwealth.com.