Craig Fuller — founder of FreightWaves and Firecrown Media — explains how he got fired by his father (twice), built a $20M freight data company, then stumbled into buying niche print magazines starting with Flying Magazine. Three years in, Firecrown owns 54 titles across aviation, boating, and astronomy and is doing $60M in revenue at 20% margins. Craig walks through the content-to-commerce playbook: buy undervalued audience-first magazines, fix the cost structure, raise subscription prices, and build Commerce businesses (aircraft financing, real estate, e-commerce) on top of deeply loyal audiences.
Speakers: Sam Parr (host), Shaan Puri (host), Craig Fuller (guest, founder of FreightWaves and Firecrown Media)
Introduction: Craig Fuller and Firecrown Media [00:00:00]
Sam: All right, my friends. Today’s episode is special for me, and it’s going to be special for anyone out there who’s a creator or who owns a media company.
I’ve got this friend named Craig Fuller. Craig runs this company called FreightWaves — it’s a data business, but they have a media arm. It’s a huge company. They’ve raised tens of millions in funding and they make tens of millions in recurring revenue.
However, on the side he ended up buying a bunch of magazines — including flying magazines, a bunch of boating magazines. Very weird of him to do that, and I wanted to do a podcast about that. Turns out he’s bought all of these niche magazines for a very small amount of money, and he’s only about three years into it. The company’s doing around $60 million in revenue and $12 million in profit. And it’s his prediction that by 2030 he’s going to do a billion in revenue — which is insane. A, that’s someone’s side project, and B, I wanted to learn all about it.
The model he’s doing: basically buying these magazines and then selling the audience different products and services — including building an airplane hangar and selling space in that hangar for flying magazine readers. So if you have an audience, if you want to build an audience, if you want to build a big business on top of that audience, this podcast is for you.
Meet Craig Fuller: FreightWaves and the Trucking Dynasty [00:01:30]
Sam: We’re live — this is just how we get right into it.
Craig: Love it.
Sam: It’s not often that someone’s side hobby becomes almost cooler than their main thing, particularly given that your main thing is this massive hit. You’re Craig Fuller. You’ve got this thing called FreightWaves — it’s a data business, but you guys also have a popular media arm. You display most of your financials online, almost like you’re a publicly traded company. I don’t know what the revenue is, but it’s somewhere in the high tens of millions in recurring revenue. And you’ve raised — what, $90 million for that?
Craig: $65 million in venture capital, but we raised some debt on top of it, so total it’s a little bit over $80 million.
Sam: And then your latest “side project” — which is not really the size of most people’s side projects — is Firecrown Media, where you’ve bought dozens of magazines and parlayed that into turning Flying Magazine into like a country club for flying enthusiasts. You’ve bought thousands of acres of land, built an airport, and you’re buying even more properties. And I think what Firecrown does — $50 million this year in revenue?
Craig: $60 million run rate is where we’ll finish this year.
Sam: Golly. What I didn’t realize when I was doing research: trucking kind of runs through your family, right?
Craig: Yeah. My father started what became the fifth-largest trucking company in the US — he sold the business last year. And my uncle started the eighth-largest.
Sam: So your uncle and your father were competitors?
Craig: Oh yeah. Pretty die-hard competitors. But they’re much better now — they do get along — but there was a period where they just absolutely hated each other.
Sam: Are they tight? Are they good family members nowadays?
Craig: Much better. But there was definitely a period where they just couldn’t stand each other.
Sam: My family is in produce brokering, so I grew up with truckers. It’s an interesting industry because the people who own the businesses can be pretty wealthy, but they’re still kind of blue collar — rough, even if they’re quite wealthy. Was your dad like that?
Craig: I mean, he’s a blue collar guy. He could look presentable in a suit and hold his own talking to Wall Street investors — he’s not going to embarrass himself. But ultimately, in trucking you’re operating a business with single-digit margins — 1 to 3%. You’ve got to know how to operate. It’s an owner-operator type business. He’s definitely an operator.
And he eventually sold that business — I think you know this — for around $800 million.
Sam: That’s right.
Craig: He merged it into Knight-Swift, which is the largest trucking company in the US. It was the second-largest trucking merger in history. The company did about $2.5 billion when it sold for $800 million.
Getting Fired Twice — By His Own Father [00:05:00]
Sam: And you were working for him. I read that you started working for him at a young age, kicked ass, but butted heads with the executive team, got fired — I think in your late 20s or early 30s — and then started what I can’t believe you did: day trading. And then you were like, I’ve got to build something. So at 36, or 34, you wanted to do almost like day trading but for freight. Is that right?
Craig: I got fired twice, actually. I got fired from my father’s trucking company, US Xpress, in 2005 — it was actually my older brother who became the CEO of US Xpress who had to fire me in 2005.
Sam: Dude, your family is a bunch of… I love them, but this is a family tradition.
Craig: You fire each other and go start your own business. After that they had a payments company — a fuel card company that they had incubated — that I took over, scaled up, and then we sold part of it to US Bank. We were doing both fleet card processing and debit card processing.
Sam: What’s a fuel card? I know truckers have them but I don’t entirely understand what they do or how they make money.
Craig: When truckers want to buy fuel — figure 200 gallons if they’re truly topping off their tank — that’s $1,200 to $1,400 in one fill-up. And what a fuel card does is fraud management. Think about it: US Xpress had 9,000 truck drivers, and you’re essentially giving them all an expense account. They’re buying fuel, but they’re also doing over-the-road maintenance — tires, breakdowns, which could be $10,000 to $20,000 on a breakdown situation, or thousands in tires. A truck driver is responsible for probably $6,000 to $8,000 of expenses per month total. So you have a lot of fraud that can happen. Fleet cards manage that fraud both on the fuel spend and on all the maintenance.
Sam: Got it. I never knew what those did.
So you grew that payments thing, it was working out fine, and then you got into FreightWaves. How long did it take to get into the tens of millions in revenue?
Craig: About a $20 million business in two or three years, something like that.
Sam: How did it grow that fast?
Craig: The timing was great — there was a lot of venture capital being invested in the space, and you had this digitization taking place where companies were trying to digitize the supply chain. And then I had relationships. It’s funny: my dad didn’t put any money in the company — he told me I’d be a bad CEO and refused to invest — so I had to go raise venture capital.
Sam: Are you and your family close?
Craig: Oh yeah. My dad and I talk. Now, after he sold US Xpress, he’s my largest investor in Firecrown. We’re actually really tight.
Sam: I’ve been following you for a while, and when I think of a good media CEO, you’re one of the people I think of. What attributes did you have that made him think you’d be a bad CEO?
Craig: I had run a payments business — they fired me in 2014 because it was a tech business, and tech businesses, while they generate a lot of margin and scale, actually burn a lot of capital. Trucking is a cash flow business. He didn’t understand that a tech business as it scales would actually consume capital. He got really mad, didn’t want to raise any money, and fired me because he didn’t think I could run a profitable business — because that’s not how technology companies typically work in their early phases.
What’s funny about that business is it’s now one of the most valuable assets in the family’s portfolio. It just got a $500 million valuation last September. So it’s done well. But I’ve been out of that business for many years.
How Craig Discovered Niche Magazines [00:12:00]
Sam: All right — this is the main thing I wanted to talk about. There’s this blog I love called Flashes and Flames. Maybe 10,000 people a month read it. If you’re a fan of media businesses, it’s my favorite blog on the internet — it’s written by this guy named Colin Morrison, based in England. He wrote this article called something like “Why Magazines Are the New Trophy Asset.” And I read that you saw that article and thought, I’m going to go buy magazines. Is that right?
Craig: Yeah. The piece was essentially about trophy assets — he was using the example of Marty Bandier buying Time Magazine and others. It was really interesting, and I was thinking about it. I had just taken up aviation, taken up flying, and I was reading Flying Magazine and feeling pretty uninspired. So I thought, it would be cool to own an aviation magazine. Flying Magazine would be my trophy. I’m a pilot, and that’s something I’d love.
So it inspired me to reach out to the owners of Flying Magazine and ask if they’d sell. They said it’s not for sale, but we’re happy to talk. I made an offer, and they ended up selling it to me.
It started off as a side hustle. I didn’t actually intend for it to become what it is — I thought print magazines were dead and that dinosaurs read print magazines. I was skeptical of the whole model. But when I bought it, I fell in love with not just the content but the value print brings to an audience. What I found is that these print magazines are completely undervalued. Nobody will touch them because they share the same philosophy I had — they’re dying — yet they own these fantastically great communities and audiences that have been around for decades.
Particularly as you get into older populations who grew up with magazines, they still have these really important connections to the brands. That’s a really interesting opportunity.
Sam: Were you liquid when you decided to buy it, or were you thinking, if the price is in the millions, I’m going to have to get money from someone else?
Craig: I had enough money to pull it off. I mean, it was a meaningful amount relative to my liquidity — in terms of my total net worth, not significant, but I have a lot of paper net worth. So relative to liquidity, yeah, it was a big number.
Sam: Then what was the thinking? Like, I’m going to have to buy this and spend some hours per week making sure it doesn’t lose money?
Craig: It was profitable. It was generating about half a million dollars in EBITDA as a standalone entity — about $2.5 million in revenue. So it’s a small business. We buy businesses at three to five times EBITDA typically. We’re not talking about a huge capital outlay. It came to about $3.5 million total when you look at cash and some deferred expenses and deferred payments — $2.5 million up front and $1 million deferred.
Sam: But then you’ve got to deal with journalists. A lot of times I think of hiring journalists and I’m like, I’d rather be a beekeeper. I’d rather go for hikes. This seems like the worst possible side hobby.
Craig: Look, FreightWaves had 40 to 50 contributors who qualified as journalists. I knew what the rodeo was going to look like running teams of journalists. What was different with magazines, though, is these are different from younger digital-native journalists. Magazine journalists don’t do it because they make a lot of money — they do it because they love the content. And there’s a sense of defeatism that exists across all publishers.
Across the multiple acquisitions we’ve done, I’ve seen this: the editorial teams feel like the owners don’t love them and aren’t willing to make investments. They almost look at you as liberators of their business. They love the content, they love the subject matter, they have the relationships — these people are micro-celebrities in their own community, the old-school influencers. And yet they get no love from corporate.
What’s happened is the whole magazine business model collapsed in the last ten years. The internet destroyed the way magazines used to make money. Rather than digitizing or evolving their model, publishers just started cutting costs as a way to fend off the inevitable. At some point the value to the community is diminished, and these things just spiral. So we come in, buy them, and in some ways liberate them from that inevitable decline. They feel encouraged by that.
We upgrade the paper, upgrade the quality, make investments in the editorial team. Flying’s editorial team went from three people when we bought it to 30.
Sam: Wow.
Craig: You have three primary full-time employees and then contributors submitting once a month. It may be an airline pilot, a flight instructor, someone who really knows the jet market — subject matter expertise. Writing is secondary for them; it’s a side hustle to make a little money. What they’ve also not done is invest in print quality, online assets, any of that.
Fixing the Business: Raising Prices and Growing Revenue [00:20:00]
Sam: How much revenue did you do in the first year of owning it?
Craig: In 2022 I think we were about $6.5 to $7 million in revenue.
Sam: Oh — so you aggressively grew it? How?
Craig: We invested. A couple of things we did: we invested in the magazine and we raised the price. The magazine was generating $8 in revenue per subscriber per year. And it cost them $15 to fill that subscriber.
Sam: Wait. The average yield per subscriber was $8 a year?
Craig: That is the revenue — the topline number. Not revenue minus hard cost. They were losing $7 per subscriber per year, and had been since as far back as our data went — since 2006.
Sam: So Flying Magazine was losing $7 per subscriber per year? That’s insane.
Craig: Yeah. They were losing $7 per subscriber. So our communication to the sales team was: you’re going to raise the rates on advertising, and on subscriptions we basically said if somebody’s not willing to spend $30 or $40 a year, they don’t really care about the content.
Think about this: to buy an airplane you’re going to spend a minimum of $50,000. Most of our audience is buying $250,000 to $1 million aircraft, and some of our audience is buying $75 to $100 million planes. If they’re not willing to spend $30 or $40 a year for a subscription, they’re also not going to buy the advertised products.
Sam: How many subscribers did you have?
Craig: When we bought it, about 108,000 subscribers. When we raised the price — we raised it to $30 initially — it actually went down to 32,000 subscribers.
Sam: No way. You bled it out?
Craig: But that’s okay — we wanted that. There were a lot of what we call freeloaders. Basically people who had subscribed through like a school fundraiser and didn’t actually care about the content. I basically said I don’t want any of them. I want people who actually care. And we were very successful at that. Subscriptions grew substantially in terms of actual full-paid subscriptions and subscription dollars — we basically doubled subscription revenue over the course of a year while having a third of the subscribers.
We’ve been down to 32,000; we’re now about 45,000 and we’ve grown it since.
Sam: Are you able to manage this growth off the cash flows of the business, or did you have to put more capital in?
Craig: I put more capital in — I wanted to put more capital in, even though I could’ve run it tighter.
Sam: How much total?
Craig: Total, we’ve invested about $40 million in the business — but that’s across all the acquisitions, not just Flying. I haven’t raised outside capital. My father invested when he sold US Xpress — he’s my only outside investor, other than two brothers who were early Freight Waves investors who got 15% of Firecrown for $500,000.
Sam: So you grow it to $7.5 million — how much profit?
Craig: About break even at $7.5 million, because we weren’t optimizing for profitability — we were optimizing for growth.
The Aviation Campus: Buying 1,500 Acres [00:27:00]
Sam: So around the end of 2022, I think you were like, “holy crap, I might have hit on something interesting” — and either thought to buy more magazines or came up with the crazy idea to buy all that land.
Craig: I bought the land in 2021 — about 1,500 acres. Originally I didn’t plan on being in real estate. What we actually wanted was to build a media center connected to a runway. Because for the aviation audience, people care less about the pilot and more about the airplane — this is no different than a car magazine where you’re looking at the Lamborghini or the Ferrari. We wanted to create a video center connected to an airport.
The problem was none of the regional airports around Chattanooga were willing to work with us. You have to get approval from the municipality, the state, and the FAA to build a media center. So we decided to build our own headquarters.
I was looking for about 50 acres, came across this piece of land with 1,500 acres, priced at $3.65 million. I drove up there and it reminded me of this resort in East Tennessee called Blackberry Farm. My wife absolutely loves it — it’s sort of back-to-farming, agricultural. I showed up and thought, this looks and feels a lot like Blackberry Farm. That was the original inspiration: create a fly-in community with a runway and home sites connected to the runway, with that Blackberry Farm-inspired experience.
Sam: How much did you pay for it?
Craig: $3.6 million. I borrowed it from the bank.
Sam: I need to understand your psychology here, because your net worth is significantly higher than mine — your business is bigger — but I’m more liquid. And even I’m scared to make some of these bets. You seem way more offensive. Why? What gene do you have that makes you think these wacky ideas are going to work?
Craig: Data. My experience suggests that it will. But it’s also taking more shots on goal. Like, I put $3.5 million into a real estate investment — if it goes to zero, I still own $3.5 million of land. At the end of the day the land has value.
Sam: But that’s still a huge project to get into. You didn’t know anything about real estate.
Craig: But you can bring in teams to run those things. It’s a matter of scaling businesses and hiring teams. Yeah, it’s risk — but real estate isn’t like building a SaaS business. The risk is actually lower because you own the physical assets at the end of the day.
Sam: I think the risk is lower for software because you can start with significantly less money.
Craig: True. But I own the land. That 1,500 acres at $2,400 an acre — if it was subdivided, those acres might go for $50,000 to $60,000 each in that community. So we knew the land had underlying value. We just didn’t know if there would be demand from pilots.
We advertised in January 2022 — we took out ads in our own magazine to test the market. The ad was written as if my wife were the target audience — the Blackberry Farm audience. We wrote a story about building a resort. We didn’t focus on the aviation aspect, which is what you’d expect. We focused on the amenities and the experience we were going to build.
We didn’t expect a lot of response. We got over 300 inbound inquiries from that one ad in our own magazine. People signed contracts to reserve their spots. We knew then we had a winner.
Sam: Did you make a joke about being new to this, or were you more professional?
Craig: We were transparent, but we recruited people who actually had experience — master planning, development. There are groups that take on a lot of the burden. You’re not going to do 1,500 acres yourself — you bring in airport planning consultants, development consultants, people to deal with zoning and environmental and engineering. I have a team that manages all the different pieces.
People wrote in and said, if you’re able to build this, count me in for a lot on that property.
Sam: What’s the price?
Craig: The lots are $600,000. The homes are probably $2 to $3 million.
Sam: And what did they give you as a deposit?
Craig: $20,000 per lot. We got up to about $28 million in total reservation deposits. But we thought we’d get through environmental and zoning approval quicker — we thought we’d break ground by the end of ‘22. So we had some churn. We’ve refunded some money because these are fully refundable deposits. We’re at about $15 million in total reservations right now.
The Content-to-Commerce Playbook [00:37:00]
Sam: This project is awesome on its own. But then it gets even crazier — you’re like, all right, this worked for Flying Magazine, what happens if I go out and get more titles and do this whole content-to-commerce thing?
Craig: Not initially — I was doing all of this with my own money. My father invested when he sold his trucking business. I was using bank debt, frankly, and liquidating my portfolio. I felt like I’d rather invest in myself than invest in the S&P.
I think the difference between us isn’t necessarily that I’m willing to take more risk — I’m willing to take more shots on goal. The fundamental asymmetric mindset I have is: I may lose, let’s say the real estate project goes to zero, I’m going to lose $3.5 million. That sucks. But you know what? My dad cut me off, fired me in 2014 — I basically had nothing. I was on my own at the bottom. I had to figure it out. I’ve done that before. So I’m not afraid of losing it all, because I know I can get it back.
We apply that rule to everything. We make acquisitions under the philosophy that it’s asymmetric risk. Say we buy a magazine for half a million or a million dollars and it goes to zero — we’re completely wrong about our thesis, and the thing is just a dog. We write off that half-million or million dollar investment. But if we’re right and we get a 3x, 5x, or 10x multiple, that creates an enormous amount of value. Bank debt is also frankly pretty cheap.
Sam: The way I think about it: as a private company entrepreneur, if most of my net worth is illiquid, any liquidity I get — whether from annual cash flows or selling a company — I take all of it and put it somewhere safe. “This doesn’t exist. I have enough, forever.” Then I use a much smaller sum to start more companies and live off the income. If they sell, great. If not, I still have that other thing. What you’re doing is different — bolder, probably more fun if it works — which is: even though your main company is doing quite well, you’re piling your liquidity into potentially risky things.
Craig: FreightWaves at some point will sell. That’s the nest egg for my long term. I know it’s going to sell; who knows what it sells for. But there is fundamental tangible value in the business. It’s totally de-risked. I have a salary too — the board takes care of me. So for me, that asset will set my family up for at least a generation. But diversifying my risk through all these other projects actually enhances my long-term returns — particularly if I’m using my balance sheet to borrow money from banks at relatively low cost.
Sam: What about diversifying your time?
Craig: That’s what teams do for you. Preston Holland, I think you know him — we brought him in to initially run Flying; he’s now running an aircraft financing business we’ve built. Reese is running our real estate project. I fired myself from almost every functional role I had at FreightWaves. I have Spencer Pand who’s my CFO and COO running most of the day-to-day. I’m working on strategy and thinking about the long-term prognosis of the business — so I can run deals and look at additional ways to lever this up without getting caught up in the minutia.
Scaling to 54 Magazine Titles [00:44:00]
Sam: How many titles has Firecrown acquired at this point?
Craig: About 54, I think.
Sam: Did you buy them in batches?
Craig: In the magazine business, it’s hard to get scale with one title because there’s a finite audience. Typically a publisher needs multiple titles. Here’s the thing about magazines: only about 25% of the cost structure is the editorial product or photography — that’s the only part a customer actually experiences. The other 75% is audience development, magazine production, layout, infrastructure. You need a lot of infrastructure to run a successful magazine operation.
I mean — and Sam, you’d know this — when we think about The Hustle, you could have had three people on editorial and the rest of the company was infrastructure: people selling ads, managing ads, making it grow. Three people bringing all the value is just how media businesses work.
Sam: Yes. When I ran The Hustle, we had three people on editorial and 37 people selling and managing ads. Three people bringing all the value — it’s crazy how these media businesses work.
Craig: So when we buy a magazine, we’re buying a portfolio — not just one title but three or four that come along with it. We’ve done maybe 20 different acquisitions that make up the 54-title portfolio. Some have been really big. We bought Bonnier, which is the largest publisher in Sweden — sort of the Rupert Murdoch family of Sweden — and they owned a bunch of boating titles. We now own Boating, Yachting, Sailing World, Salt Water Sportsman, and others. We have a large aviation portfolio and a large marine portfolio. And we just recently bought model trains — a bunch of railroad titles — and astronomy titles.
Sam: So whatever 12-year-old Craig is into — boats, planes, RC trains, space. It’s almost like a five-year-old boy’s dream: boats, airplanes, trains, and space. Pretty magical.
Craig: What we’re buying are audiences that love the content. By owning the magazine — which we finance through the P&L of the magazine itself, subscriptions and advertising — we make money in media. But ultimately we’re buying the audience to offer them some other product or service.
The Playbook: Audience, Intent, and Commerce [00:48:30]
Sam: Let’s walk through the playbook. Step one: acquire customers profitably through a media arm that generates its own profit via subscriptions and advertising. Step two: make sure the audience will spend money on something. Is that right?
Craig: Essentially — but if they’re enthusiasts and if the category is big, the answer is pretty much always yes. Think about it: these are magazines that have been around for decades. Some over a hundred years. They’ve survived multiple wars, multiple pandemics, the Great Depression. The audience truly cares enough to subscribe. If these magazines have survived multiple phases of the internet age, they’re going to be around for many more years. We’re buying them because the audience cares deeply about the content, and they will naturally buy another product or service.
Sam: And then step three is raise prices and sell ads better?
Craig: We don’t look at it in steps exactly. We have a media business that runs the media operation. Then, as we go find commerce opportunities — say, aircraft financing — we find a CEO who can run that business through its own P&L, separate from the media business.
What you’re doing well is looking at it from the perspective of the spend opportunity of that audience. If you’re reading Flying Magazine, you’re either a pilot, an aspiring pilot, an aircraft owner, or someone who wants to own an airplane. A student pilot is going to spend $10,000 on flying lessons. If they’re going to be a career pilot, they’ll make $15 million over their career — a lot of opportunity to help them along that journey. An aircraft buyer is going to buy insurance and financing too, and they’ll have a lot of expenses throughout the life of owning that aircraft.
So we’re optimizing the magazine and its advertisers based on intent, not based on raw reach. We explain to advertisers: wouldn’t you rather reach the 100 people who are going to buy your airplane than 100,000 people of whom 99% are never going to buy your products? We get into intent data through digital — print is just one aspect of what we do, but it’s driving intent data to demonstrate real value to advertisers.
Sam: That’s a very good pitch. And then you hire people to build commerce businesses on top of those audiences — airplane financing, classified ads for planes, the real estate project. How much do you invest in a new business before it needs to become profitable?
Craig: We’re patient — it depends on the business. If it’s growing and hitting its KPIs, we’ll continue to support it. Every business is different. The real estate business hasn’t broken ground yet, so that will take many years to generate profit. The aircraft financing business is a brokerage — it should reach profitability much quicker.
We also own six e-commerce businesses now. We own the largest NASA merchandise store on the internet — it’s called The Space Store. The aviation nerds and the space nerds have a tight Venn diagram. You want a model of a rocket or a patch from a mission — SpaceX or NASA — we can sell you that.
Sam: What are you going to do with boating — build a harbor?
Craig: No. I don’t think we’ll do real estate for boating. The arbitrage in aviation is that you’re taking a beautiful piece of land that isn’t next to a body of water — and you’re arbitraging it by putting a runway there. Pilots want to be there, and the runway creates the value. With boating, lakefront or oceanfront property is already priced for that value. The market’s already priced it in accordingly.
For boating, we’re looking at financing, e-commerce, and other categories where we think we can be successful.
The Numbers: $60M Revenue, 20% Margins, Billion-Dollar Goal [00:55:00]
Sam: I think you said $40 million total invested across all of Firecrown?
Craig: Yeah, between my own capital and my father’s investment — that’s been predominantly through M&A. We haven’t used outside capital otherwise.
Sam: And you’re going to do $60 million in revenue this year. On the tweet you said 10 to 15% profit?
Craig: Profit in March was 18%, and we think we can sustain 20%. We think ultimately it levels out around 30%. So $60 million in revenue, a little bit over, at 20% margins.
Sam: What would that be worth?
Craig: If you look at public comps, probably 12 to 15 times earnings. But our goal is to get to a billion dollars. I have no plans to sell this business. I love cash flow, Sam. It’s not just taking risk — I actually love cash flow.
Sam: It’s funny as a venture-backed founder — you get jealous. I’ve heard this; we’ve talked about it on this podcast before. You get jealous of the cash flow guys.
Craig: The cash flow guys get jealous of the valuation, and the venture guys get jealous of the cash flow. Almost every founder I know is super jealous of the cash flow guys — like, wait, we built this fantastically high-valued business but we don’t see any of that money until exit.
Sam: But you have both at this point. So on $12 million in profit, 10 times is $120 million?
Craig: 10 times is fair for a private trade. So the business is worth at $60 million run rate — maybe $120 to $180 million. We started this in 2021. That’s pretty good for four years.
Sam: And you said by 2030 this gets to a billion in revenue?
Craig: That’s our goal — through both organic and inorganic growth. There are 4,500 magazine publishers in the US, and there’s no exit for these guys. Either they’re owned by large corporations that want to divest their print products, or they’re family-owned businesses that have been running for multiple generations and don’t have an exit.
We’re doing a deal right now — a business with about $1.5 million in revenue, about $600,000 in contribution after owner expenses. We’ll pay less than one time for that business. There are just not a lot of buyers in this category. And ultimately you’re buying the audience — that’s really what it’s all about.
Yes, we generate profit and cash flow — that’s great. But I like to say we’re a private equity business meets venture capital. VCs want the asymmetric 100x return. We’re going to incubate businesses that can potentially bring those high-level returns, using the audience we already own. E-commerce is never going to hit that mark, but an aircraft financing business or a real estate project very well could. We’ll find other business models as we grow.
The Hearst Comparison [01:01:00]
Sam: You’re basically building a Hearst-style company. Have you read The Chief — the biography of William Randolph Hearst?
Craig: I have not.
Sam: You should, man. It’s awesome. So William Randolph Hearst — his successful father was a miner, and in a gambling bet he won the San Francisco Chronicle. He goes to his son and says, “William, you’ve got the Chronicle. You’ve got a year to make it not lose money.” So he does that — by creating what’s called yellow journalism, which is basically clickbait from the late 1800s and early 1900s. He kicks ass, he crushes it. He starts buying another thing, and another thing, and another thing. He buys all these titles, kills it. This is like a cable business before cable — recurring revenue, subscriptions, massive margins.
Then they get so big they do a bunch of other things. One, they invest in this new sports network called ESPN. Hearst owns something like 30% to 50% of ESPN — they’ve made a billion off that. Then they buy Fitch Ratings, which is a data business, which is exactly what you’re in. At this point, Hearst is owned by the family. It’s one of the largest family-owned businesses in America. They own this massive building right in the heart of New York City. They own a ranch in Wyoming. They own everything. It’s been around for a hundred years.
Craig: Hearst is amazing — $10 to $12 billion in revenue, no debt. What’s pretty astounding about Hearst is they have a very large venture capital portfolio as well. They’re an investor in FreightWaves, by the way.
Sam: Oh, so you know all about them.
Craig: I met with them — I forget who I met with there, but I learned a lot about them. They’re like older guys, they wear suits, very Mad Men era. It would have been a bad fit. But yes, that’s what we’re building.
Look, I think media businesses are underappreciated. What we’re seeing now is this: if you own a strong media asset and you can build products on top of that audience — that’s the playbook. These audiences love the content, they’re paying for a print magazine or a digital experience, they’re already there. We can offer them products and services they naturally buy anyway.
Sam: When you say that, I think yeah, that’s so obvious. But a lot of people have tried this and few have succeeded. Hinckey I think is succeeding. But when BuzzFeed says they’re going to do it — it never works.
Craig: I think BuzzFeed and a lot of other publishers sold out to programmatic and relied on the platforms — the Facebooks and the Googles. Nobody really loves BuzzFeed. The difference is we’re buying magazines that have been around for decades, where the audience’s father and grandfather read Trains Magazine or Model Railroader or Flying. It has real affinity. We just have to find the services that naturally sit on top of that.
How Craig Operates: Hours, Goals, and What Drives Him [01:07:30]
Sam: How many hours a week are you working?
Craig: I don’t count my hours. From when my kids wake me up at 6 AM until midnight, I’m pretty much either with my kids or working on the businesses. But this isn’t work to me. This is a game in some ways.
Sam: You’re still in grind mode, though. It’s not like you’re on a beach.
Craig: I do it to myself. I end up getting overwhelmed and then I’m like, I only have myself to blame.
Sam: What’s your goal? You want to be a billionaire? You want to do cool stuff? You want to create something that lasts a hundred years?
Craig: One of the reasons I love media businesses is you’re always learning something new. You get intellectually stimulated by a new challenge — a new audience, a new product. I don’t know, it’s… you don’t want all the power and fame that comes with owning Space Magazine.com, and Trains Magazine is going to give you an enormous amount of power.
Sam: Yeah, model railroaders — huge power brokers.
Craig: It’s not that at all. It’s not even the wealth. It’s more the chase. It’s putting up the score in some ways. Solving problems. Learning about a different industry.
I have a business I paid $10,000 for — it’s called Aero Swag, an e-commerce business, a print-on-demand T-shirt shop for pilots. It’ll do $100,000 this year. I spend more time on that business proportionately than any other one just because I think it’s cool. I genuinely enjoy the tinkering.
Sam: I bet it feels awesome to make your dad regret firing you.
Craig: It was fun proving that I could make it work. But most successful people have a similar story — a girlfriend or boyfriend that broke up with them, a parent who said no, someone who made one rude comment. In my case there was also a media executive who said in passing, “Man, these newsletters will never make more than a million dollars a year.” And I was like… you son of a…
Sam: And you thought about that every day?
Craig: Every day.
Sam: I see this guy sitting at floor seats at the Knicks and I’m like… you son of a… I would say the best thing you can give a founder is an enemy.
Craig: At FreightWaves I had a guy — the CEO of our largest competitor — who really pissed me off. He told me I couldn’t compete against them. I woke up every day thinking about him. But he got fired, and I tell you, the motivation wasn’t as fun anymore. I needed him to be the guy. All of a sudden the company became nice to me and I was like, no — please go back to being difficult, because I wake up slightly more motivated every day with an enemy.
Sam: I was like that with the founders of Morning Brew. I was like, I want to kill you. But now they’re like family to me — they’re some of my best friends. And now I’m hosting a podcast on their platform, so.
People say, “Don’t be hateful toward this person.” And in my head I’m like, dude, rage is the greatest fuel ever. Someone once told me: “If you got hate in your heart, let it out.” I’m like, no — I’m burying that deep. That’s fuel. I need that.
Craig: It’s also good for the team. If they share the hatred of the enemy, they’ll fight harder than if they don’t.
Sam: I love that. It’s like a sport — once the whistle blows, anything goes. But once the game’s over, it’s all love and respect. While we’re between those lines, though, we’re getting after it.
Craig: Exactly.
Sam: Dude, thanks for doing this.
Craig: Enjoyed it.
Sam: Craig Fuller — that’s the pod.