Sam Parr profiles Bradley Jacobs, a largely under-the-radar entrepreneur who has built five companies valued at over a billion dollars each — spanning oil brokerage, waste management, equipment rental, and logistics. Sam walks through Jacobs’s repeatable playbook: find a fragmented industry, acquire mom-and-pop operators, add salespeople, build systems, and scale rapidly. The episode closes with reflections on what drives Jacobs and lessons Sam takes from his approach.
Speakers: Sam Parr (host), Andrew (co-host)
Introducing Bradley Jacobs [00:00:00]
Sam: So the guy I’m going to talk about today — his name is Brad Jacobs. Bradley Jacobs, I think he goes by, but we’re going to call him Brad Jacobs. This person is super interesting because he has started five companies that have either gone public or are worth over a billion dollars. He started at age 23; he’s 64 now. Google him — Brad Jacobs. He’s worth somewhere in the range of three to five billion dollars.
Sam: He’s bought — or rather, he doesn’t invest passively like a venture check. They buy companies. And he’s bought something like 600 to 700 companies. He’s done it across a variety of industries, using the same strategy over and over again in different industries. It’s incredibly interesting. This guy is very fascinating to me for a variety of reasons that I’m going to explain.
Sam: Andrew, have you heard of this guy? Brad Jacobs — do you know anything about him?
Andrew: I don’t know anything about him.
Sam: That’s kind of why he’s cool. He’s kind of under the radar. If you Google him, he’s got a bald head and he looks like a finance guy — he wears a tie, he’s pretty well-spoken. You think he’s just a private equity person. And I guess maybe he is, but he’s really an entrepreneur. He’s very entrepreneurial and far more interesting than a lot of the typical New York hedge fund types.
Business 1: Amerex Oil Associates [00:01:30]
Sam: So I’m going to give you a quick story about his background. He started five things that have been quite meaningfully sized.
Sam: The first was called Amerex Oil Associates. He started it when he was 23, and it was an oil brokerage firm — which I’m not entirely sure what that entails, but I imagine it just means connecting folks who created the oil to large businesses who are buying the oil. Within a very short amount of time — only about four years — remember, he started this when he was 23, so by the age of 27, Amerex, his oil business, was doing $4.7 billion dollars in gross oil bookings. Meaning that’s how much oil they were buying and selling. Now, I imagine his company kept a tiny percent of that — like one or two or three percent — but incredibly impressive for a young guy.
Sam: After a few years he sells that business for a billion dollars.
Business 2: Hamilton Resources [00:03:15]
Sam: Then, only a couple months after that, he starts this thing called Hamilton Resources. He starts it out of England. He convinces a French bank to give him a billion-dollar line of credit — which was pretty remarkable even though he was already quite successful, and crazy young. But he made it happen.
Sam: Here’s what he said: “We moved physical cargos of oil from one place to another. The ’80s turned out to be a great time in the oil business, and I built Hamilton up to about a billion dollars in revenues and did business in dozens of countries before I moved back to the States in 1989.” So between ‘83 and ‘89 he started this business, and it was also huge. I believe he ended up selling it for north of a billion dollars. That’s business number two.
Business 3: United Waste Systems [00:05:00]
Sam: Business number three is a little bit of an odd one: waste management. I don’t think there’s anyone doing brand-new waste management right now, but there were a ton of companies that started in the ’70s, ’80s, and ’90s — like Waste Management, the company — and what they did was go out and find tons of mom-and-pop waste management companies. Because back then, that’s how it was.
Sam: He started this thing called United Waste Systems, which eventually became the fifth largest solid waste business in America. It had a very simple business plan: buy landfills in small markets, buy many of the local trucking companies serving those markets, optimize the truck routes, maximize pricing, get margins up, achieve size so that they had the capability to scale. They did that and the strategy worked really well. In just five years, earnings compounded annually at 55 percent. He took the company public about eight months after starting it, and the stock price went up roughly 50 percent every single year for about five years.
Sam: Oh, sorry — I just gave you the numbers for his next business. The waste management company grew to $2.5 billion dollars in revenue and sold to Waste Management. Nuts, right?
Andrew: That’s crazy.
The Four Types of Entrepreneurs [00:07:30]
Sam: One of the most interesting things about this is — I always think there are like four different types of entrepreneurs. Let’s take Chipotle as an example. There’s the innovator — the guy who rolled the first burrito and was like, “Oh, this tastes really good.” Then there’s the remixer — the person who creates Chipotle, who takes the burrito, packages it up, creates a brand around it. Then there’s the scaler — the person who scales Chipotle to 100 locations. And then there’s the optimizer — the person who just sits on top, makes sure it doesn’t blow up, and gets as much juice out of the lemon as they can.
Sam: This guy’s a great example of a scaler. Someone who takes something that already works, that’s already proven, and just does a much better job of it — rolls it out, makes it scalable, and builds something massive.
Sam: What’s sexy about this guy is actually how boring the businesses are. They’re so basic. These are things that are essentially undisruptible. When you build them it’s like a hundred-year business — which I think is really cool. Whereas what we do, you’ve got to think in five-year chunks.
Andrew: I completely agree.
SEC Document and the Fund-Raising Strategy [00:09:30]
Sam: If you scroll up to this document we have open and click “source” — the source I’m using for a lot of this is so interesting. So we’re on business number three; I’ll get to four and five in a second. But one of my lessons from this guy — and I’ll say it right now — is that he raises money like a madman. It’s not a ridiculous amount. I mean, saying you’re raising tens of millions of dollars — for the average show, yeah, that is a ridiculous amount — but he’s got a track record and he turns those millions into multi-billion dollar things. So tens of millions is not that much money relative to the outcome.
Sam: If you click that source thing — what does that take you to?
Andrew: To the SEC.
Sam: I found this file on the SEC and I don’t even remember how I came across it, but this is what interested me. It’s a Q&A session — he’s written it out — and he basically lays out the strategy of his fourth and fifth businesses. It appears to be a Q&A that he prepared and showed to a ton of potential investors and potential banks, and they decided to invest in him. I think this was before the company even started.
Andrew: So you’re saying this is what he raised on? There’s no deck, nothing — it’s just this document?
Sam: I’m not entirely sure, but I think that is part of it. It’s called a Schedule 14A. I’m not an expert in SEC filings — I believe that’s something you have to answer before a board of directors at a publicly traded company raises money — but I’m not entirely sure. What’s interesting is he writes in wonderful, straightforward, simple English. You could read his entire strategy, which I’m going to go through in a second.
Business 4: United Rentals [00:12:00]
Sam: So he started two oil brokerage businesses, then he started a waste management business. His fourth one is called United Rentals.
Sam: If you pay attention now — and if you’re listening to this and you live in America — go on a drive downtown wherever you live and look at the big box trucks and rental equipment. Look at the Caterpillars, the Bobcats, the construction equipment, the porta-potties — anything involving construction or heavy equipment. I guarantee you on a lot of them you’re going to see “United Rentals.” That is the fourth company that he started.
Sam: He started it with the same idea as waste management: find a massive industry that was highly fragmented by small businesses that were profitable and great but didn’t have enough capital to grow and were kind of bad at sales. That’s what he did.
Sam: In just five years, it grew to $4 billion in revenue and $1.2 billion in EBITDA.
Andrew: Is he growing via acquisition or is he just rolling this out and crushing competition across the country?
Sam: We’re going to talk about that, but what he said was: “We got there partly through acquisitions, partly through organic growth by developing greenfield locations. We grew by using the same strategy we used at United Waste — we bought about two-thirds of the branch locations and cold-started another third from scratch. I actually prefer cold starts,” is what he said.
Sam: The business plan for United Rentals was to become the largest equipment rental company in the world and leverage their purchasing power, branding, and other advantages of size. Within 13 months they became number one, leapfrogging Hertz — which had been the number one equipment rental business since 1965.
Sam: Another thing they did was go fast. They went public fast. They formed the company on Labor Day weekend and were trading on the New York Stock Exchange by December. Merrill Lynch said it was the fastest IPO they had ever seen.
Sam: He stepped down from United Rentals in 2007 — only about five years after starting it — to start the next company. And when he stepped down, if you look it up now, I believe United Rentals’ market cap is $25 billion. He spent five years on this company and it’s worth $25 billion.
Andrew: Crazy.
Business 5: XPO Logistics [00:16:30]
Sam: Listen to what he did after this. He wrote: “After I stepped down I began looking for my next big thing. I studied tons of industries and ended up concentrating on transportation and logistics. It’s larger and more fragmented than the industries I’ve previously been involved in. It’s a $13 trillion dollar industry.”
Sam: And here’s what this guy does — at this point he’s already a multi-billionaire. He basically spends three months reading tons of industry reports, and then he calls a hundred experts in each industry and just sits down with them and asks questions. It might as well be a podcast. That’s how he learned.
Sam: So he’s this multi-billionaire, big shot, done all this amazing stuff — and he calls these people and just sits down and listens. That’s all he does. It’s pretty amazing.
Andrew: Yeah.
Sam: And then he started his new thing — it’s called XPO Logistics. Have you heard of this?
Andrew: I have heard of this. I think it’s a delivery and logistics company — like a competitor to FedEx, at least that’s my understanding.
Sam: We’ll put this in the show notes, but in that document up top — the one from where he was raising money for XPO Logistics — in plain English he explains what they did and his reasoning for getting into it. He basically says: I studied loads of industries, this one seemed interesting, I went and interviewed a hundred people who were experts on it, I hired really good people, and we’re going to do X, Y, and Z. And that X, Y, and Z is exactly what he’s done in his previous businesses.
Bradley Jacobs’s Playbook Explained [00:19:30]
Sam: Now I want to wrap up by giving you the incredibly detailed strategy on what he does.
Sam: The first thing he does: he looks for huge industries with lots of fragmentation — small businesses that are profitable and great but don’t have the capital to scale. Here’s what he says: “In a nutshell, this is how you ramp up. You buy a brokerage or some type of small business with $30 million in revenue and you add 30 to 40 bodies to it and you double revenue in time. I’ve looked into companies that have executed this plan but most of them don’t have the capital to sustain it. I try to find those businesses and I bring all the capital to do it.”
Sam: The second thing he does: he hires salespeople. He says: “I like to hire hungry, talented salespeople at a low base but big upside for incentives. I fund their training for a few months and it’s not that hard for the winners to build a million-dollar book after a year or so. It’s a business where you have to make 99 calls a day and do one or two deals. So you have to hire people who are psychographically tested high on the need-to-win scale and low on the need-to-be-liked scale. A salesperson will have a base of $25,000 to $35,000 but can make many times that amount through a really good incentive program. Once you get the right people in the system and integrate them on the right IT, it can be really powerful.”
Sam: And finally, speaking of IT — when someone asked him what was the best acquisition he ever made, he said they made a powerful software acquisition with a politically incorrect name called Rental Man, and they used that to integrate all of their rental businesses. “We rolled everything up into that company. We couldn’t have made the hundreds of acquisitions we did without Rental Man.” That was his best acquisition of all time.
Sam: And that, my friend, is Brad Jacobs.
What Drives Brad Jacobs? [00:22:30]
Sam: I both love and find these guys kind of mysterious. I wonder — what’s missing in all this? What keeps him going? What’s his purpose? How does he use his money? Why does he do this? What’s the driving force?
Sam: I researched him and the guy looks like a Wall Street stiff. Did you look up what he looks like?
Andrew: Yeah, he looks kind of like a character actor — like a generic nerdy, Steve Ballmer-looking kind of guy.
Sam: Yeah, he looks like he would be in Biden or Trump’s cabinet. But I’ve actually seen interviews with him and he’s very endearing. I don’t think he’s actually just a stiff Wall Street guy trying to milk all the numbers out. I actually think he just loves to build. He constantly talks about integrity. He goes: “The common denominator of everything we buy is that the people we buy from have to have high integrity. And one of our moats is we take care of the people who work at the businesses we’re inheriting. In fact, the biggest risk of our plan is that the people we buy companies from will leave — so we treat them all really, really well.”
Sam: So I don’t think this is all just cold finance. When I got his energy from interviews, I actually believed that he was a good dude and this is just his art.
Sam: What do you think though? What do you think he does with his money? Is that kind of public? Does he do any philanthropy or anything? Because I always find it so interesting. I mean, there are two ways to look at doing good in the world. It’s like: okay, you do capitalism — you employ a whole bunch of people, you make an industry more efficient, you add to global GDP, good things happen because he does this. But on the flip side — what’s driving making more money? Maybe it is just continually, maniacally going industry by industry and improving and optimizing them. That’s his gift or whatever.
Andrew: Yeah, I don’t really know what he does with his money.
Lessons from Bradley Jacobs [00:25:00]
Sam: I can wrap this up by sharing a few things I’ve learned from this person.
Sam: The first is taking the red pill — or whatever you want to call it. When you look at what this person is capable of doing, or when you read what he’s done, if you didn’t know it was true, you’d say, “Well, that’s impossible. No one can do that.” But the person has done it repeatedly over and over again, and he seems pretty nonchalant about it. What I’m learning from him is that you can create these amazing things and it’s hard, but maybe it could be kind of simple.
Andrew: It’s so inspiring, right? You basically go find an industry that has — let’s look at the restaurant industry in general. Restaurants are disorganized, very difficult businesses, very low margin. People have done this essentially in restaurants by building fast food chains. You go in, you build systems, you do training, you incentivize people the right way, and you can make a lot of money doing that. But you can’t make a lot of money usually in an individual restaurant. So what he’s done is gone out and found these fragmented, disorganized industries — like waste management or logistics — and said, “Okay, I’m going to do the fast food chain version for that industry.”
Sam: Yeah, and it’s really cool.
Andrew: It’s really really cool.
Sam: The second thing I learned: he actually does the same thing that I do — though I actually don’t know your numbers, but I bet they’re similar. He likes to buy companies between five and ten times earnings. That’s his number.
Andrew: Yeah, I’d say I love to buy businesses at that valuation or close to it. But the problem with buying a business at that valuation is that you’re buying kind of a crappy business often.
Sam: Exactly what he’s doing. He’s kind of building a platform where it’s like: I just need one so I can build the systems, and then I can go and acquire a whole bunch more.
Sam: The final thing — and then we can move on — is that the guy loves debt. And oftentimes that ends badly. But I personally have zero debt in my life; I’ve never really had debt. And I actually think that not having any leverage is kind of silly. I’ve read articles about him and he talks about debt very unemotionally. He seems like a really charismatic, emotional guy, but when it comes to debt he’s like: “Yeah, look — this makes total sense. I can grow this business at 30 percent, therefore the cost of capital math says I should allocate capital this way.” And I hear that and I’m like, yeah, everything you’re saying makes total sense. I’m just fearful. And it’s really cool that he doesn’t seem to have that fear.
Andrew: Yeah, and I think debt goes back to not having potentially fatal blow-ups in your life. I was talking to a guy — super rich — and he goes, “I’ve paid off my house in full. I never have a mortgage.” It just gives him that sense of security. Maybe this guy has so much money from previous wins that he can take a little more risk, or he knows how to structure debt. But you hear both things. And the problem is you only hear the stories about the guys who levered up and did really well. There may be a whole bunch of other Brad Jacobs types who went out, levered up, hit a speed bump, and lost everything.
Sam: Oh yeah. And the interesting difference between what we do and what this guy does — this guy is essentially starting a new business every time. What we like to do is find a business that’s already working, leave it alone, maybe plug in a new CEO, and not mess with the DNA. This guy is modifying the DNA. He’s doing CRISPR on these businesses — warping them, transforming them. He’s working really hard.
Andrew: I get really excited when I hear about people like this, but then I’m like, “Oh my god, this is a big lift. I don’t want to do it.”
Sam: It’s a big lift. But it does seem cool. It’s like cornrows or sleeve tattoos — I think they’re cool, I just don’t want them. They’re cool for certain people and it works great for them.
Andrew: Exactly. Not for me, but pretty sick that someone else has it.
Sam: Totally. And I do think again — going back to this — this guy makes the world better. He employs a lot of people in industries where people aren’t getting laid off because of him. Because he’s managed the businesses better, he can probably pay people better, give them more opportunity, not lay them off because he’s got this global business. It’s very positive.
Sam: But what I would want to understand is — what’s the guy do with the money? What’s driving him? Is he like a sad, empty hole where he feels like he has to keep doing this all the time? Or is he donating it all to charity, or does he view this as super philanthropic in and of itself? I’m super curious about that.
Andrew: I don’t know. The only thing I saw is that he has a good Glassdoor rating.
Sam: Which I actually — everyone dismisses Glassdoor, but I’m like, yeah, there is a signal there. I got made fun of for bringing that up on the Michael Saylor podcast. But I’m like: it’s not hard facts, but there’s something to it. Glassdoor is basically people only go on there when they really hate you. So it’s the voices of the people who hate you most — and if even those people are saying good things, or at least okay things, that’s a really good sign.