We spoke to Rob Walling in this week's episode of Moneywise.
Rob is a successful SaaS entrepreneur who has built and sold multiple companies, including Drip, an email service provider and marketing automation platform that he exited in 2016. He's also the co-author of "Exit Strategy," a book about the emotional and financial aspects of selling a company.
Like all Moneywise episodes, Rob breaks down his net worth, income, portfolio, and monthly expenses and then I, your humble host, pick it all apart.
We also went deep on: how he's diversified his wealth into collectibles, particularly rare comic books, and why he believes they're both a sound investment and a source of personal joy.
Below you'll find my summary of the episode along with the entire transcript.
And by the way...this podcast, the concept of it came from Hampton. Hampton is a private, highly vetted community for high-net-worth founders. Some of the stuff we talk about on the show is stuff we actually talk about in the forums, on calls, and at in-person events at Hampton. Highly recommended if you liked this conversation or want to have conversations like this with people like Rob. The Hampton community is made up of around 1,000 amazing founders and business people. There are around 100 events each year. If you're a CEO, founder, or business owner, check this out. New Moneywise episodes come out weekly.
Now, below are the notes and the full transcript.
Rob's journey to financial independence came primarily through building and selling software companies. Before his major exit with Drip in 2016, he ran a SaaS company called HitTail that netted him $350,000 annually while working just 10 hours per week.
"That's a hell of a business. You know, it's a lifestyle business. And that was great," Rob shared. But it was Drip that represented his biggest success, growing to "ten employees, a few million in revenue" before the acquisition.
The exit process was extremely challenging emotionally. "Very stressful. One of the most stressful things I've ever done in my life, but totally worth it at the same time," he explained. This experience prompted him and his wife to write "Exit Strategy," focusing on navigating exits without personal implosion.
"It's like, yay, I'm gonna make $20 million, and then I'm gonna get divorced the week after because I've completely torched my relationships. Like, this is not an uncommon story," Rob warns other entrepreneurs.
For Rob, collecting rare comic books serves dual purposes: portfolio diversification and personal fulfillment. His interest in comics dates back to childhood, when he and his brother ran a small comic reselling business in junior high and high school.
"When our net worth was $400,000, I didn't want $40,000 sitting in some asset that wasn't doing work because we needed it to do work," Rob explained. "You get an eight-figure net worth and you can have half a million, a million... sitting somewhere and it doesn't need to do the work. If that makes you happy."
Rob's approach to collecting is strategic. He focuses on proven properties like Spider-Man, Batman, and Superman rather than trendy collectibles. "I buy things that are proven properties," he noted, adding that his initial strategy was to diversify across Silver Age comics as a sort of "index fund" approach.
Most notably, Rob views his comic collection as a luxury that brings genuine joy: "Not a week goes by that I don't go through and look at the covers of almost every comic that I own... and it's really fulfilling to me."
Rob's collectibles strategy focuses primarily on comics that have demonstrated enduring value. He explains the hierarchy of comic book eras: "If you go back to the Golden Age, that's where the books are a lot more rare... getting into the Golden Age is more expensive, but I actually think they hold their value better."
His approach isn't just random collecting - he's leveraging decades of knowledge about comics: "The reason I went with comics is I have some type of advantage because I have this background. I have 20 or 30 years of knowledge of it."
While Rob estimates his comic investments are up 25-30% overall (down from 50-60% at their peak), he acknowledges they haven't outperformed the stock market or crypto. "The volatility of collectibles I'm now learning is more than... the stock market," he shared, noting that the collectibles market as a whole dropped 40-50% from its peak.
Some purchases have been particularly meaningful, like his first appearance of Spider-Man: "I bought a higher grade than I really wanted to, but I just saw a good deal come up and spent $50,000 or something on it. And I remember that was the most expensive book I owned at the time... heart palpitations."
While Rob approaches his collection analytically, he admits the emotional component can sometimes override pure investment logic: "If you enjoy something, you can sometimes convince there's emotion there. And so it's like, 'oh, well, I want to buy this book. Is it because it's a really good investment or because I just want it?'"
This emotional connection creates practical challenges too. Rob stores his most valuable comics in a bank safety deposit box and keeps others in a home safe. "The amount of money you have to spend on insurance and safety deposit boxes or a safe... it's a physical thing. It's kind of a pain in the ass," he acknowledges.
For those considering collectibles as investments, Rob advises avoiding trends and focusing on items with proven long-term value: "Think about the value of Superman number one or Action Comics number one that has been valuable now for 80 plus years... to me, it's the difference between gambling and investing."
Ultimately, Rob's approach to wealth reflects his values: "The reason that I got into entrepreneurship was 100% about freedom. It wasn't about getting rich for getting rich's sake. It wasn't money for money's sake. It was so I'd have enough money that I could work on whatever I wanted to for the rest of my life."
"I'm not a crypto bro or anything, but after I sold drip in 2016, you get this big pile of money and it's like, I'm going to diversify into a bunch of things."
"We value experiences way more than stuff, so we don't buy a lot of stuff. We have nice cars. I drive a Volvo, but it's like we get them used."
"There was a certain thing about some of these books when I hold them up... this is when I know I've made it is holding this thing because this means so much to me."
"At one point I realized autographs are actually shockingly inexpensive. You can get a Picasso autograph... I think I got it for like $2,000 at auction."
"I think 3 to 5% is probably where I'd prefer to be [with collectibles]. Yeah, let's just say it's 10 to 12% somewhere in that range... part of it is a little lack of self control, if I'm being honest."
"I know people who bought Bored Ape and all that stuff... if you do that with comic books or art, where it's this recent thing that's run up really quick, think about the value of that versus Superman number one that has been valuable now for 80 plus years."
[00:00:02] Rob Walling: I've had a couple books where people have flown here, and I've met them at the airport and they've handed it to me.
[00:00:08] Sam Parr: That's Rob walling. And even though that sounds like a spy movie plot, he's talking about comic books. He's a collector. And for him, his collecting serves two purposes. One, it's a way to diversify. And two, it's bloody fun. I'm Harry Morton, and this is Moneywise, a podcast. Not about how to make money, but how life changes after you already have. In this episode, we're talking to Rob about the emotional and financial case for collectibles. Nerds. Get ready. And really quick. The podcast is a show for Hampton, Sam Parr's highly vetted private community for high net worth founders. Go and check it out at join Hamptons.com. Collecting. We kind of do it as a kid, naturally. Pokemon cards, baseball cards. Action figures, stuffed animals. We're almost collecting collections at that point. And while the Beanie Baby bust may have turned some of us away from collecting for investing as adults. It's actually not a bad diversification strategy, with some caveats, which we'll get to. But that's not the only reason Rob does it. It also brings him a lot of joy, which is really what you should be using your money for anyway.
[00:01:12] Rob Walling: It is a luxury that I've granted myself when our net worth was $400,000. I didn't want $40,000 sitting in some asset that wasn't doing work because we needed it to do work. You get an eight figure net worth and you can have half a million. A million, you know, you can have a lot of money sitting somewhere and it doesn't need to do the work. If that makes you happy. That's at least my take on it. Like, why did I make this money if I'm not going to spend it on a few things that I like? Because again, like, we don't buy sports cars, we don't buy other quote unquote frivolous things or stuff that people might consider frivolous. But I do think that giving yourself permission to own some things that maybe don't make sense, I had to do that myself, because everything I, everything I owned growing up had to make sense because there was just only so many dollars to go around. And so I kind of had to go through an evolution after selling that last company of like, you know, give yourself permission to be a little, um, I don't know, irrational or illogical with it if it makes you happy.
[00:02:06] Sam Parr: Of course, this is provided you can afford to have a few million in bobbleheads sitting around with the potential that you'll never see a dime of that money back. Rob, can.
[00:02:14] Rob Walling: I have an eight figure net worth? Low eight figures. I don't know that it matters if it's. What is it? Ten, 20, 30 million. Like, at that point, it's all kind of the same, I think. And I am we we, my wife and I have probably a third of our net worth in public. Equities, stocks and everything else is spread around in there's a bit in crypto. I'll tell you what. There's more in crypto than I would like because it went up so much. It's one of those weird things where it's like, I'm going to put 3% of my net worth, and then you look and you're like, oh, 30% of my net worth is now in this super volatile thing, right? So I've obviously been selling a bit of that over the years. Some real estate, some metals, some angel investments. And collectibles.
[00:03:00] Sam Parr: We'll get into just how deep Rob's gone into collectibles in a bit. I will hint that it's enough that he even sometimes questions if he overdid it. But first, let's get some context about where his money's come from. Can you walk me through then? Like running your first big company? Because I know you launched a bunch of, like, projects, and it was sort of a stair step approach that you've talked about. But what was that first big company?
[00:03:20] Rob Walling: I mean, it depends on how you define big. You know, at one point I was running a SaaS company called Hittail that I had acquired, and it was just me, and that was the goal. I had like six contractors that I worked with and it made. How much did that business make? Probably netted me $350,000 a year. And I worked ten hours a week on it, you know. And so to me, and that's not a big company by definition. But to me, that's that's a hell of a business. You know, it's a lifestyle business. And that was great. And then drip was after that. It was an email service provider and a marketing automation platform. That's the biggest company I ever built, which grew to what do we have? Ten employees, a few million in revenue. And then I sold that in 2016.
[00:04:06] Sam Parr: So what was that exit like in 2016?
[00:04:09] Rob Walling: Very stressful. One of the most stressful things I've ever done in my life, but totally worth it at the same time. My wife and I actually just wrote a book called Exit Strategy, and it is all about that process. It's about thinking through your exits. It's about processing the exit and dealing with it and not imploding as it's happening. Not accidentally divorcing, getting a divorce, or pissing your spouse. It's like, yay, I'm gonna make $20 million, and then I'm gonna get divorced the week after because I've completely torched my relationships. Like, this is not an uncommon story. It's really, really hard. And then we talk about the after. What do you do next? You know, how do you not rush into the next thing?
[00:04:45] Sam Parr: So is that where the majority of your money has come from then was that exit in particular?
[00:04:50] Rob Walling: Yeah, I actually did a podcast episode on my On My Own podcast and the number one way that I have made money in my life, the way that I got to the point where I don't have to work anymore, is selling SaaS companies, like selling them. And then number two, a little sad, but it's crypto. I'm not a crypto bro or anything, but after I sold drip in 2016, you know, you get this big pile of money and it's like, I'm going to diversify into a bunch of things, right? I'm going to buy some obviously quite a bit of a, you know, index funds and such. I'm just a pretty boring investor. But should I put three, 4% of my net worth into metals? Sure. Should I put three 4% of my net worth into another asset class? Oh hey crypto is this thing. So in like fall of 2016 I start dollar cost averaging into Bitcoin and Ethereum. Just like it's going to go to zero or it's going 100 X was my bet. I figured it was like an angel investment. You know obviously that paid out. So the number two way in my life is crypto. And then the number three is Angel investments. And I put money into WP engine in the first year and a couple other things. And that's that's a power law where it's like, I have 20 angel investments and, you know, one of them. One of them made millions, basically. And the rest are, you know, breakeven or less.
[00:06:01] Sam Parr: And roughly how much do you spend per month? What's your kind of family. Monthly burn.
[00:06:05] Rob Walling: Mhm. Mhm. I'm usually really good with numbers. I'll be honest I don't actually I mean ten grand like we don't have a house payment right. We paid cash for the house I did. So I went to buy a house and they wouldn't give me a loan because I didn't have a job, because I had sold my company so they wouldn't give me a loan. So I was like, I guess I'm paying cash for this. Seven figure, seven figure sum. Nothing I ever thought in my life I'd be able to do, you know? So without a house payment, it's just, I don't know, ten grand a month on stuff?
[00:06:34] Sam Parr: Yeah. What do you spend your money on? Like, what else are you spending on?
[00:06:38] Rob Walling: We like experiences. I mean, we value experiences way more than stuff, so we don't buy a lot of stuff. We have nice cars. I drive a Volvo, but it's like we get them used. So I'd pay 40 or $50,000 for, you know, a car and drive it for 5 or 10 years. That's just how I've always done it, right? I don't I'm not. My wife likes sports cars a little more. But even then, it's weird when you hit the point where it's like, oh, she said, I might want to buy a Porsche. And I was like, okay, go do that. And she's like, you're not going to disagree. If you want it, go buy it. You know, I don't. What is it, 80 or $90,000? Like? I know this sounds like a lot of money. It feels weird for me to say it's just not anymore. You just write the check for it. So as a result, we don't have a ton of stuff. We have a nice house because we spend a lot of time in it. We both work from home. We have two kids, um, we pay up for travel. And so, you know, if I'm going to go somewhere, I'm going to fly Delta Comfort+ or maybe even spring for first class. At a certain point, if I don't get upgraded and we stay at nice, nicer places than we used to, that's probably the biggest expense in a given year.
[00:07:36] Sam Parr: Yeah, I love that.
[00:07:37] Rob Walling: And then stuff. You know what else is crazy expensive? Is insurance, insuring this house, insuring, you know, we have not a ton of cars. We have several cars. I think we have four cars. Just insurance on that alone is crazy. That's probably the number two expense, I'm guessing in terms of a monthly or an annual burn for us, which is just stupid.
[00:08:00] Sam Parr: After the exit or a big liquidity event, there's always that question what do you actually do with your money? How do you turn those big numbers in your bank account into something that actually brings happiness and meaning? For Rob, collecting wasn't just about owning rare sought after stuff. If that were the goal, it would never have brought him any fulfillment. What does make it a fulfilling investment strategy is that it ties back into something he's been passionate about since he was a kid, and lucky for us, the origins of his love for comics and his journey into entrepreneurship happened to overlap nicely.
[00:08:31] Rob Walling: I naturally was drawn towards entrepreneurship. I like to say I grew up working class, which is like my dad was an electrician. My mom didn't work while we were young and so we never went without food. But we had there was no extra money, you know, and I drink powdered milk. As a kid sometimes when we didn't have enough to buy real milk. Right. So for any type of anything that I wanted, it was like birthday, Christmas or I had to make money. And we lived out in the country. There was no getting a job somewhere. Like I couldn't just get an hourly job so I would buy candy in bulk from Costco or Price Club. And I remember paying $3 for a big tub of Now and Laters. That's a US candy. I don't even know if they have them elsewhere in the world, but it was $0.03 per pack of now and later, and I could sell them for $0.25. So I had an eight x markup and I would turn $3 into $25, you know, over the course of a month or something, which was a tremendous amount of money in the in the early 80s, I could buy a lot of batteries for my Walkman and I could buy comic books. And in fact, my brother and I ran a little comic book business. We never had a storefront, but we, um, in junior high and high school would, uh, resell comics. There was a big boom in it, and we were being entrepreneurial. So I've always had a love for them as a medium.
[00:09:47] Sam Parr: Now he's just doing the same thing that he did as a kid, but instead of having a couple of bucks, he's got millions. And instead of the comic books being worth $0.50, well, they're worth tens or even hundreds of thousands of dollars, but the satisfaction is all the same. So tell me which ones are your favorites?
[00:10:01] Rob Walling: That's so interesting because it's like, which of your investments are your favorites? You know, how do you think about that? I mean, I guess, I guess realistically, I really like Spider-Man. And so a lot of like, I have his first appearance in like a mid grade because his first appearance in high grade goes for millions of dollars. Right? And I'm not willing to, you know, to put that much money into to something like this, a piece of paper that can be ruined in a fire or get stolen, like I even I have my limits. But first appearance of Spider-Man, one of my favorites I have. I would love the first appearance of Batman and Superman, but they're also too expensive even in the lowest grades. So I have I have Batman number one, and I have Superman number one. Those are not their first appearances, for whatever reason. But, uh, you know, in low grade, those are quite expensive and they're neat books. And probably my other one that, you know, one that I wanted as a kid and I couldn't afford was Teenage Mutant Ninja Turtles number one, the first sprint and it was like hundreds of dollars single digits back in 1985, and I couldn't afford it. And so I got a really high grade copy of that. And that book was worth six figures on its own. And that was a moment. There was a certain thing about some of these books when I hold them up or when I, you know, when I bought them and I thought, this is when I know I've made it is holding this thing because this means so much to me.
[00:11:11] Sam Parr: Yeah, I love that so much. And by the way, when you're touching them, are you like putting gloves on and shit? Like, how seriously does one take comic book preservation? I don't know this. This is not my world.
[00:11:21] Rob Walling: So they are encased in plastic. So you could, you know, I don't have gloves on because it's just a piece of plastic. So there's a third party grading company that grades them. And if you're going to do investment grade collectibles, that's what you do. Like, if I were to buy I don't own any, like trading cards or baseball cards or any of that. But like you send it to a grading company and they kind of they say it's a 1 to 10 scale, right? And they say like this is an 8.5. And so you kind of know what it's worth. So yeah. No. If these were not graded and encased in these, they call them slabs or encased in the plastic. Oh, you. I would be so nervous to even touch them. I would 100% of gloves on. You're talking about, you know, whatever. A $50,000 piece of paper that's 90 years old. 80 years old. Like there's a lot of danger.
[00:12:03] Sam Parr: Yeah. Wow. That's amazing. It's so funny to me is like to separate the joy and the passion for the thing and wanting to, like, enjoy it and, like, interact with it, because that's what ultimately it's for. But then you can't. It's like I remember, like for some reason, this stuck with me when I was watching the, um, maybe it was Toy Story or something, like basically the idea of keeping something box fresh. I'm like, ah, like, I get it. I understand why collectors need to keep it in the box, but it's also like, this is the thing that I've been dreaming of since a kid. Like, I want to hold it in my hands and like, enjoy it. It's hard for me to divorce those two things.
[00:12:33] Rob Walling: It is. And there are a lot of collectors that don't like to have their stuff graded. You don't have to have your stuff graded. It's really if you're going to sell it, it confirms that it's authentic. It's not restored because that drops the price. You know, someone colors something in with a Sharpie RB, and it really confirms the grade for books that I really like. I will buy a graded copy to me, that is investment grade that I expect to go up over time, be able to sell, and then I'll buy a ratty restored, you know, cheap copy of it. I mean, you can have a book that's worth $50,000 in a high grade, that you can get a ratty copy of it for 500 bucks or $1,000.
[00:13:09] Sam Parr: Yeah. As cool as it could be to own a ninth grade copy of some super famous comic. Owning something that valuable and fragile, something you'd be afraid to breathe on the wrong way, is likely to add some unnecessary stress to your life. But there is some level of stress Rob is willing to take on, not just because these are cool things for him to own, but also because at the end of the day, this is just an investment strategy tailored specifically to his interests.
[00:13:32] Rob Walling: Once I sold the last company and I was looking at ways to diversify, what I really was trying to go after was, I want to decouple, right? I want things that are not correlated with the public markets. And I thought that collectibles, metals and crypto would not be correlated. It turns out when we saw the big crash in 2022, everything went down anyway. So I throw my hands up at this point and be like, I don't know, I don't know. It's diversification, you know? But I don't know that it's not correlated. But I was drawn for those two reasons of like, oh, it's just another asset class, and it's an asset class that I have an advantage in because I do know the comic book world, you know, and me re-entering it 5 or 6 years ago, as probably when I did, I realized, oh my gosh, I might actually, it might be cool to put a few hundred thousand dollars into this asset class and kind of just it's like a hobby slash way to diversify is how I think about it. I enjoy it more than owning index funds, which cuts both ways, right? Because if you enjoy something, you can sometimes convince there's emotion there. And so it's like, oh, well, I want to buy this book. Is it because it's a really good investment or because I just want it, you know. So you do have to weigh that.
[00:14:38] Sam Parr: Rob's not just collecting for fun, but the fact that he loves what he's collecting gives him an edge that most investors don't have. Collecting purely as an investment strategy without that is a much riskier game, which is good news for all you comic book nerds. Your brain, full of seemingly useless knowledge, might actually pay off. After all.
[00:14:54] Rob Walling: If I could have my druthers, I would collect cards rather than comic cards are smaller. They're easier to store. They're easier to ship, they're less likely to get damaged. But I don't know anything about cards, right? I don't have an advantage. Much like the same reason 20 years ago I was trying to make money or to become financially independent by investing in real estate in Los Angeles. It's where we lived at the time, and I realized I had no advantage, no advantage. I was just like everybody else, and that's why I got into software and started building SaaS companies is I had an advantage because it's hard to do. And I was a developer and then I learned how to market, right. Similar. The reason I went with comics is I have some type of advantage because I have this background, right. I have 20 or 30 years of knowledge of it, and I collect it as a kid. But all things being equal, I would I would go for cards. They're just they're simpler.
[00:15:42] Sam Parr: That's not to say Rob doesn't dip his toes in other collectibles. He's just not relying on them for the same kind of return.
[00:15:48] Rob Walling: I've dabbled in other things. I own a few pieces of original art, like Eastman and Laird, who, you know, created the Teenage Mutant Ninja Turtles. I have some pieces of theirs from the first 3 or 4 books, but art is expensive and it's one of a kind. And I'm always like, it's hard to value. I do own a bunch of signatures. At one point I realized autographs are actually shockingly inexpensive. I say, shockingly, compared to a lot of things, you know, you can get a Picasso autograph. So I have like him writing something in, I think it was in Spanish and then signing it. And I have this little card and I think I got it for like $2,000 at auction. And it's just neat to me that Picasso signed that. I have a I have a tattoo of one of Picasso's, like, a guitar on my arm. And so it's like, meaningful. I got an Alexander Hamilton signature for like 4 or $5000, and that's neat. Like, it's a piece of paper that he wrote on in the 1817, Seven late 17, early 1800s. That's neat. I got a Napoleon signature for $1,200. Like, think about that. It's so neat, you know. And so I view those as just. It's cool. I have maybe 10 or 15 signatures. Maybe they'll be worth more later. But there's also a neat factor of owning something that does. It does retain its value. These things are not going to zero. It's not like I it's not like I bought a brand new car and drove it off the lot, you know? But I don't view those as much as investments. The comics that I buy, I view like, oh, these should go up. Otherwise I'm not making a good decision with my money.
[00:17:14] Sam Parr: What percentage of your net worth is in collectibles right now?
[00:17:17] Rob Walling: I can tell you what percent I wish was collectibles. I think 3 to 5% is probably where I'd prefer to be. Yeah, let's just say it's 10 to 12% somewhere in that range. Okay. Part of it is because of appreciation, you know, because things have gone up. And I was like, oh, you get an attachment to them. And it's like, well, I don't want to sell that one because I believe long term in it. And part of it is a little lack of self control, if I'm being honest.
[00:17:42] Sam Parr: A lot of people think about collectibles as sort of as fun rather than like a serious investment. So what's your argument for it? This is hard to divorce the passion piece from the fact that you have the unfair advantage that you talked about. But I'm interested in this idea of like, would you still buy into them if you weren't a fan, but you did have that sort of knowledge somehow without being a fan?
[00:18:03] Rob Walling: I probably would, because even before I got back into comics, because it just kind of occurred to me one day I was like, I wonder what comics are do. I haven't even thought about comic books in 20 years. I wonder what they're doing. But even before that, I was already buying little things that I enjoyed. Like Bill Watterson, right, is the guy who created Calvin and Hobbes, and he's just a great artist. He didn't sign very much. He's just kind of a curmudgeon and he's still alive. But his. As a result, like anything he signs is worth a lot of money. And I had before about comics. I had a little Bill Watterson signed thing that I was hanging on my wall, and that was neat to me. And I did view it as like, oh, I bet that'll go up in value. But I can also justify it because I enjoy it. And that one funny story I got at an auction for like $4,000, maybe 5000, and then a year later it was auctioned. It was it went for like 15 or 20,000, and I sold mine because I can't justify hanging something on my wall that's worth that much.
[00:18:55] Rob Walling: That's crazy talk, right? So I just I up and sold it. I'm not sure that I answered your question, though. Your question was, would I do it if I didn't enjoy it purely as an investment? Yeah. And my answer is yes. I think I would have because I really wanted the diversification. The difference is I probably would have invested. There are like these micro like almost private equity funds or these private investment funds where they make the investment decisions. And if I didn't know it, I probably would have put, you know, a small amount, again, two, three, 4% of my net worth into one of those funds and let them manage it and make the decisions is how I would have handled it, similar to how I allow Vanguard or T Rowe Price to kind of just buy indexes and this and that. Right. I'm not going to I don't buy individual stocks at all because I don't feel like I have an advantage.
[00:19:38] Sam Parr: No. Same. That makes total sense to me. And by the way, what's the most expensive collectible you own? Is it the turtles? What did you say? Turtles. Number one.
[00:19:45] Rob Walling: Turtles. Number one. I think it's Superman number one or Batman number one, I think, are the two that I think are even worth more than the turtles. Took a big hit. They spiked way up in 2021, and then they took a big dive in 2022. And so I think the number one is worth less. Now. This is that thing of it's a short term versus long term bet to me too right.
[00:20:05] Sam Parr: That's so interesting to me that they fluctuate in that way. That is kind of fascinating to me. Is that because of like the cycle of the movie, like because obviously there's been a couple of the turtles movies, like, is that what spiked it? Or like they're super interesting that suddenly it goes out of favor.
[00:20:19] Rob Walling: It was the asset bubble, the, you know, everything that happened to, you know, the money getting pumped in in 2020 and 2021, that again, that's where I was thinking, well, comics are not or collectibles in general are not going to be correlated with because what happened? Stocks went up, startup valuations went up, crypto went up, kind of. Everything went up. Collectibles did too. And then what happened in 2022? It all came crashing down. And that that was a big thing. The difference with turtles, the reason turtles has crashed so hard is it is more of a modern comic. It's made in 1984. There are more copies in higher grades. So there's a there's still demand, but there's a lot of more supply compared to Superman number one, where they have a census of how many of them are graded. And there's only 77 in the world that are encased, you know, graded. Now, people think that there are another 30, 40, 50 that are ungraded in the world, maybe up to another 77, but that's it. That's the total population of that comic in the world. And so if you want to buy it, it's just not going to fall that far. The other weird thing is valuing these things.
[00:21:22] Rob Walling: It's not like a stock where you can just go and say, well, how much is this worth? Because the stock is traded hourly every minute, every microsecond. You know, I mean, a popular stock, right? You know, the value of it. You know, the bid and the ask spread. What about a comic book that in that grade only sells every two years? What is the value today if a copy hasn't sold for 12, 18, 24 months? You know, so it it gets, the rarer you get. It does become a little more I won't say a guessing game, but you do have to kind of use some judgment. You know, so it's not an efficient market, if that makes sense. It's not as liquid as a stock or crypto that I could sell today if I wanted to sell one of my expensive books. I can set it as a buy it now, and it might take months and months and months to sell, or even if I want to sell it via auction. There's only so many big auctions in any given year. It's not like eBay where everything's coming up. If you're going to sell a $50,000 book, you don't put it on eBay, right?
[00:22:16] Sam Parr: What's your experience like being selling it? Like, are you just sitting there watching the numbers tick up and hoping to God you don't lose tens of thousands of dollars?
[00:22:23] Rob Walling: Yeah, that's usually what it is. I mean, I've sold a lot fixed price. Basically, when I find myself either thinking it's not a good investment or when I don't enjoy owning it anymore. You know, when I look at it and I'm like, why do I own this? This is a waste. Then I'll usually start by trying to do a fixed price sale, because that's the safer way to go. And when that sells, it's like, oh good, I'm getting rid of something. It'd be like, you know, if you have an old pair of shoes or a bunch of books and you're like, when you sell them, it's like this feeling of a little bit of freedom that I'm getting rid of this stuff. But putting them up for auction is stressful, and sometimes it goes over what you think it is. But in my experience, most of the time it goes for less than I think it's worth and it's super frustrating.
[00:23:02] Sam Parr: Do you personally have a rule for how much you'll spend as well?
[00:23:05] Rob Walling: I probably should, and I used to have this mental rule of like, well, I'm not. I just can't bring myself to spend more than $10,000 or $15,000 or $20,000. But then the further I got into it, I started realizing, you know, there's some according to me, there are some really good investments in some older books. The first wave of of books was Golden Age. It's when DC was big, right? So Justice League, Superman, Batman, Wonder Woman versus Marvel took over in the Silver Age, which was I think started in 1962. And that's when like Fantastic Four, Spider-Man, Hulk, Avengers, Iron Man, they all came out. Got it. So if you go back to the Golden Age, that's where the books are a lot more rare because you imagine a book being printed. I mean, these were newsprint and they were just for kids and people would throw them away. The fact that there's even 77 grade copies of Superman Number One is actually quite a testament. Are there 77 copies of of the newspaper that came out the day, you know, the New York Times that came out the day Superman number one did? I don't think those exist. So it's kind of, you know, an interesting thought process.
[00:24:02] Rob Walling: But what I realized was that getting into the golden Age is more expensive, but I actually think they hold their value better. And I think Silver Age holds its value better than the the Bronze Age is what it's called, you know, and Bronze Age better than moderns and moderns are like the last 20, 25 years I think is what it is. So I started realizing, you know, I want to have a hard portfolio like diversification percentage limit. But on any individual book, as long as I can get it insured and store it in a safety deposit box, I'm willing to flex on that. And so that is when I started moving into ones where, man, you're sitting there bidding, you know, it's online, it's a live auction. There's a there's an auctioneer and you're just sweating because you're like, I cannot believe I'm hitting this bid button. And then when do I stop? When someone outbid me by $2,000 on a 50 or $100,000 book. Am I willing to pay 2000 more? Well, maybe. Maybe I'll justify. Maybe I'll go over mine, you know. So it does. This is where if you're not into it, if it's not fun, don't do it because it's time consuming.
[00:24:59] Sam Parr: Yeah, well, see, I, I sweat over like, a pair of shoes on eBay. So, like, you know, I'm sitting there like the last 30s like, okay, this is my number. Yeah. Do you go in with a number? And it sounds like maybe there is some flex there, but like, how do you stop yourself? Because I think about this when I'm watching, like the big art auctions when they happen and like, you know, some record breaking number is sold at auction and it's you kind of watch the clip on the news. I'm wondering what's going through the psyche of the people that are bidding on this thing, and at what point are they going, no, this is silly. Now I can't go any higher.
[00:25:29] Rob Walling: It depends on how badly you want the thing and it depends on how often it comes up for auction. That's it. So there are some things where I'm like, that'd be nice to have. And so I think it's worth $10,000 based on previous comps and other grades around it or whatever. I'd be willing to pay 9500 for it if or 9000, you know, or something some or even ten. And then if it goes past that, I'm like, that's okay. And then there's others where it's like, this only comes up for auction every I mean, there's books I see that are up for auction every two years, every three years in a particular grade or in a way that's affordable. And those ones get tougher because then you're like, well, I think this is worth 30 grand. But it's like, if I miss it, I need to wait a very long time to get it again. And so those are the ones that I think there's a bit more flex. And so when you've seen Dorothy's ruby slippers from The Wizard of Oz, those just got auctioned for 30 something million dollars in the last few months or wasn't there. There was like a declaration of Independence. I believe there's only like 10 or 11 known copies. And one of those came. There's three in private hands and one of those came up for sale. Man, all bets are off then. Or DaVinci, like any type of DaVinci thing, like there are certain things that are just so rare. It's like I think a billionaire is just like at all costs. They don't even care, right?
[00:26:43] Sam Parr: Yeah. I mean, there's only so often a banana gaffer taped to a wall comes up, right? So you've just got to act fast. It's true.
[00:26:50] Rob Walling: Oh, boy. I watch things like that and I'm like, oh no. Oh, don't do that. Yeah, no I would, I don't buy, oh I buy things that are proven properties. You know, it's like everybody I name Spider-Man, you know Batman, Superman. It's like you can go to Google or ChatGPT and just type in like, what are the top ten most valuable Silver Age comic books, and what are the top ten most valuable Golden Age comic books? Right? And it'll give you a list. And frankly, the ones that are most valuable right now in those two eras, it's all the first appearances of everybody. We'd say it's Avengers number one, you know, it's Spider-Man's first appearance. And so diversifying that, my initial thing was I'm just going to diversify across the Silver Age ones because you can get those relatively inexpensive. Expensive. And I got the top 5 or 10 and just was like, cool, that's my index fund.
[00:27:32] Sam Parr: Yeah, sure.
[00:27:33] Rob Walling: That's how I think about it.
[00:27:34] Sam Parr: Yeah, that makes total sense.
[00:27:35] Rob Walling: If I had used my head. This is the thing where when it's a hobby versus an investment, I kind of knew, like Spider-Man is super, super popular. And so Amazing Fantasy 15 is his first appearance. And if I had just put all the money into a bunch of copies of Amazing Fantasy 15 because there are thousands that are graded, I probably would have done better than anything else. But instead I said, well, I'm going to diversify one, because that's what you do with investments, I guess. And two, because it's more fun, because owning ten copies of one book is just kind of boring, you know? And instead I bought a bunch of Superman Batman Turtles, and it's more fun for me. Do I think it's returned as well as it probably could have? No. And I think that, you know, there's this again where it is, this balance of like, hobby versus a true pure investment play.
[00:28:23] Sam Parr: The best investments don't just grow your net worth. They make your life richer. That's why that balance is so important to Rob, and that emotional return he gets also helps offset some of the annoyances from investing in such fragile assets.
[00:28:36] Rob Walling: The the amount of money you have to spend on insurance and safety deposit boxes or a safe or whatever. Like it's a physical thing. It's kind of a pain in the ass, you know, it's not a passive investment like a stock or a bond.
[00:28:48] Sam Parr: Do you keep anything of value at home, like in a safe or whatever, or is it purely you kind of outsource that side of things?
[00:28:54] Rob Walling: I outsource the expensive books that I'm not willing to lose in a fire, basically. So the cheaper books, I do have a safe here at the house, and I stick them in there, and we have an alarm system and and I have insurance on everything, you know, for the full value. So I would get the money back, which is, which is fine. Um, but what's interesting is I didn't think about this when I was like, hey, I'm going to buy some comics and put some net worth in. And then I started having these. They were just sitting on a shelf in a cabinet, and my wife was like, how much are those worth? Like just these things here that, like, the cleaners could knock over, you know? And I was like, oh, all of those together. I don't know, $100,000. And she's like, what, like, store these somewhere else, you know? And it was this realization of like, oh yeah. And I guess I probably need to insure these because, like, homeowner's insurance doesn't cover them. And even if you put them in a bank, like in a safety deposit box, banks in the US, they don't insure that stuff. It's on you. If there was a fire or it got robbed. My understanding anyways is that I think if it's like cash, they'll reimburse it. But if it's like collectibles or something, they won't. So you really need third party insurance on this stuff.
[00:30:00] Sam Parr: Yeah. Okay. So it's not like come around your house isn't like visiting a drug baron with like, all these big, expensive sculptures, like, everywhere out on show.
[00:30:07] Rob Walling: No.
[00:30:07] Sam Parr: And it's like, it's all kind of put away. Does that remove any of the joy, by the way of, like, having to kind of hide them away a bit?
[00:30:12] Rob Walling: It's not bad because I am able to open a closet and see, you know, enough of them that I'm like, oh, it's still my hobby. You know, this is a neat thing. I do miss the more expensive ones. Those are the fun ones to look at. And I got to drive to a bank to look at them. So yes, that does. I wish I could justify keeping them here. You know, I own some pieces of art and I don't hang them because a the, the light, just light from the window will slowly bleach all art over time. And so that feels weird. I do have a Beatles gold record that was for Abbey road, so Abbey road's been platinum 30 times, and so they've issued 30 gold records to all four of the Beatles. Right. So 120 of these gold records. And I have one of them. And it's like, I think I got it for four, 4 or 5000. I do hang that on my wall because it's I don't think it's worth I don't even think I have insurance on that one, actually.
[00:31:06] Sam Parr: Overall, aside from the amount of joy it brings him to have these items and spend his time seeking them out, it's also been a pretty decent investment purely from a financial point of view. How much do you think you're up on your investments on these things?
[00:31:18] Rob Walling: You know, you never know until you sell.
[00:31:20] Sam Parr: Sure.
[00:31:20] Rob Walling: But, you know, I have a spreadsheet, of course, with what I think are the values, and I think I'm probably up about 30% overall, 25 to 30%. That's not annual, that's total. But at one point I was up 50, 60%, you know what I mean? And then I put money into it and 2021 and then it dropped. So it's like it's fine. It has not outpaced the stock market. You know over the time of that I've been invested for sure.
[00:31:51] Sam Parr: Have they performed better than like gold for example?
[00:31:54] Rob Walling: Yes. They perform better than gold. They have not performed better than crypto or the stock market. Originally they did. So when I started buying these. Maybe it was 2017 or 18. For the first few years they were moving faster than the stock market, and then they had this huge run up in 2021 and 2020 during the asset bubble. And then when they came down, though, they came down hard. The volatility of collectibles I'm now learning is more than the that I think than the stock market, although I guess the stock market had its big crunch right in the financial crisis. 0809 this is kind of like an equivalent of that in collectibles, where things the market as a whole from its peak is probably down 40 or 50%, you know. So the reason, the only reason I'm ahead is because I did start buying in 17 and 18 as it ran up, you know, so they're not they're back down to like 2020 levels basically in terms of a lot of pricing.
[00:32:48] Sam Parr: Of course, not every bet pays off.
[00:32:50] Rob Walling: I have several that have tanked because they're volatile when they don't come up for auction very often. If there's not enough demand for that particular book at that particular time, they'll just drop. So you get a 20, you pay 20 grand for a book, and in next auction a year later, it sells for 12 grand. And it's just like, oh boy, that was not a good choice. So I have a few nine nines that did that. That's just never going to happen with a Superman number one or a Batman number one. Someone's going to backstop that book. They're not going to let it lose half its value. Like I would step in if I saw, you know, I already own a copy of those books and I would buy another copy. That's how confident I am in the value of it. So yeah, I've definitely made mistakes.
[00:33:26] Sam Parr: Have you got any any that have turned into a surprisingly good investment?
[00:33:30] Rob Walling: I'll be honest. Buying Amazing Fantasy 15 first prints of Spider-Man. When I bought it, which was 6 or 7 years ago, people were saying, oh, that book has nowhere left to go. It's already, you know, if you looked at the past 15 years, it's already just run up, run up, run up, and is way more expensive than it used to be. And there's no way it can go higher. So you don't know. I mean, I'm like, well, I'm betting on Spider-Man, that he'll continue to be popular. And so that one has gone up. I bought a higher grade than I really wanted to, but I just saw a good deal come up and, you know, spent $50,000 or something on it. And I remember that was the most expensive book I owned at the time. And it kind of heart palpitations, you know, that type of thing. And I was like, I can't believe what I just did. Am I going to regret this? And then that's that one's worth significantly more just because it is because Spider-Man keeps going.
[00:34:15] Sam Parr: Some people dream of like flying private jets or buying lambos, and you know, your wife wants to buy a Porsche or has bought a Porsche. Why was this your version of like a dream purchase?
[00:34:26] Rob Walling: I think because the reason that I got into entrepreneurship was 100% about freedom. It wasn't about getting rich for getting rich as sake. It wasn't money for money's sake. It was so I'd have enough money that I could work on whatever I wanted to for the rest of my life, because I love building shit, but I don't like building shit that other people tell me to build. So as a software engineer at big companies, it was agonizing that I was just like someone else's agenda. And the politics were bad too, but like, it wasn't interesting work. And so for me, the whole thing around being a founder, being a maker, being an entrepreneur was, I want to own my own time. So when I get to that end and it's like, cool, now I have freedom. The goal, I don't know. The money wasn't to buy luxury. Now to that point, though, my wife did a good job of saying, look, I want to buy a nicer house because in a big house, you know, we live in Minneapolis. It's not that expensive. And I resisted that a bit. I was like, ooh, like a, you know, a house would cost seven figures. That's like, I can't imagine that I would ever live in a house like that, you know? But she convinced me, like, let's make the splurge. I think it will feel better. Just our life will be better. And you know what? She's right. I have no regrets about owning this home. I don't view it as an investment at all. I don't think it will go up, but that is probably one of the luxuries that she convinced me to do that I was resistant to, that I have enjoyed. And another one was frankly buying a Volvo. Volvo again, it's I always drove just cheap ass Chevy Blazers my whole life. Right. These very.
[00:35:53] Sam Parr: Entrepreneur mobiles. Yeah.
[00:35:55] Rob Walling: Exactly. Right. And I drove the I bought a salvage title, one that had been totaled and repaired, and I paid like eight grand cash for it and drove that for 15 years. I just don't care about luxury. But here's the thing. You live in Minneapolis. It is cold as balls in the winter, and so having remote start and heated seats and steering wheel, that's a luxury that I actually do appreciate. It's bougie or it feels that way, but it's like, you know what? Just do it, you know? So there's a few things that I've fallen into. But look, I don't begrudge anyone. If you have money and you want to buy a sports car, do that if that's your thing. I'm a guy buying fricking, you know, decaying pieces of paper here. Spending 40, $50,000. So I'm not one to, you know, to judge anyone's tastes and how they spend money.
[00:36:36] Sam Parr: There's something special about owning a piece of history, whether it's a comic, a Beatles gold record, or a start up with massive potential. It's a connection to something bigger and something that feels meaningful. And for Rob, that feeling is just as important as the investment itself.
[00:36:49] Rob Walling: Well, you're tracking it because you're like, I know this is insured as it's being shipped, but you are just nervous and you want to be there and you have to sign for it and show ID, you know, and sometimes, I mean, look, I've had a couple books where people have flown here and I've met them at the airport and they've handed it to me. And then I take them out to drinks and dinner, you know, and take them out at a certain point, it's it just makes sense to do that, you know, when a book is out. Expensive. But no, I've had multiple moments where I walk out and I have this box and I think to myself, this could be a $10 dishtowel that I bought on Amazon. But no, I know exactly what this is. And yeah, right in go in the kitchen, you open this thing up and there's all this packaging and you pull it out and I give it just a solid look of like, is it the grade they say it is? That's always.
[00:37:33] Sam Parr: The first.
[00:37:33] Rob Walling: Thing. But then the other thing is just look at the majesty, you know, holding it in your hand. It really is a tangible feeling of like joy and accomplishment. And not a week goes by that I don't go through and look at the covers of almost every comic that I own.
[00:37:51] Sam Parr: That's cool.
[00:37:52] Rob Walling: There's only 50 of them. I just flip through them and they're in a box. You know, I go to the bank for the expensive ones. I have the cheap ones that, you know, if they. I wouldn't want them to die in a fire. But if they did, I could deal with it. And it's really fulfilling to me.
[00:38:09] Sam Parr: Collecting isn't just about making money, it's about an emotional attachment to things that bring you back to that childlike joy. The financial side is just an added benefit. And if it's something you're interested in, here are a few things to remember. If you're going to invest in collectibles, you need to be into the thing you're collecting. Otherwise, the time, the research, the risk probably aren't worth it. Rob isn't just throwing his money at random stuff. He's leveraging decades of knowledge to make smart buys. And don't get caught up in chasing the hype. Buying just for value without understanding the long term demand, like a banana taped to a canvas or a Bored Ape NFT is a fast track to losing money.
[00:38:44] Rob Walling: I know people who bought Bored Ape and all that stuff. That was a hot thing. We didn't know where it was going. Maybe you were in on the ground floor. But if you do that with comic books or art, where it's this, it's this recent thing that's run up really quick. Think about the value of that versus Superman number one or Action Comics number one that has been valuable now for 80 plus years. To me, it's the difference between gambling and investing, I guess a little bit, you know. So I think that's a mistake you can easily make is seeing something that's running up feeling like, well, it's hot. Everyone's investing in that now and usually that stuff, everyone forgets about it and then it's once it's cold, it's hard to sell.
[00:39:27] Sam Parr: So if you found this interesting and you want to have more conversations with other founders who are exploring some of these interesting alternative investment strategies, you've got to go and check out join Hamptons.com. It's a highly vetted private community for founders and CEOs, high net worth individuals, and we're having these kinds of conversations all the time in private around how we're managing our money, the things we're investing in, how we're growing our startups. If that's the kind of thing that interests you, definitely go and check it out. Join Hamptons. And finally, I want to plug the production company that makes this podcast. It's called Lower Street. It's my company. Check it out at. If you're listening to this and you're thinking, I want a podcast just like this, for my company or for my personal brand. Awesome. We'd love to chat to you. Head to Lower Street.