I built a billion dollar company in 18 months

- August 20, 2025 (7 months ago) • 49:19

Transcript

Start Time	Speaker	Text
00:00	Sam Parr	Can you build a billion-dollar company in only 18 months? Today's guest is Eric Lyman, a buddy of mine who started a company called Ramp. He and his co-founder asked themselves this question before they started the company: they wanted to get to a billion-dollar valuation in only 18 months, and they reverse-engineered it. I'd heard him tell this story before, but he didn't give a lot of details. I thought it was amazing that they were this bold—and that they actually pulled it off. The company is worth something like $20 billion now, and they're only, I think, 6 years old. Give this episode a listen and let me know what you think. Again, Eric Lyman of Ramp is on today's episode of My First Million. You said something that was pretty crazy. It was: "I wanna... I wanna build a billion-dollar company in 18 months."
00:49	Eric Glyman	In eighteen months, yeah.
00:51	Sam Parr	And that was kind of shocking, because that's like—great. I mean, that's crazy fast. Is that really what happened? You guys had that conversation? </FormattedResponse>
00:58	Eric Glyman	Yeah, that's a real conversation.
00:59	Sam Parr	That you guys didn't have—were you and Kareem on the same page?
01:02	Eric Glyman	We wanted to go fast for sure. I think the world is moving faster than ever. We had already sold our first company, and we were definitely comfortable — neither of us came for a whole lot. We had already proven a couple things and, in some sense, had left very good setups. I was a 26-year-old senior director at Capital One, and he was the youngest person at that age. So we knew that if we were going to leave, we wanted to make this company big and either make it huge quickly or fail really quickly. Kareem really did have that conversation. I think he had it with Calvin, which cracked me up later when we finally did become a billion-dollar company. It occurred in 2021 — less than two years after the company's incorporation.
01:53	Sam Parr	No shit. Wait—two years after incorporation? Yeah, that's insane.
01:57	Eric Glyman	Yeah, it was crazy. A lot — a lot — of magical things happened in 2021, but it really did happen. And Calvin said, "Look, sometimes it's best not to know the odds." If I had looked it up and known, I would have seen that there was no company in New York's history ever that was worth $1 billion within 18 months, or 2 years, or 3. But yeah.
02:16	Sam Parr	What was your revenue when you...?
02:17	Eric Glyman	I did that. I mean, in 2021—jeez—that was... you've got to remember, this was like peak excitement in the market. I think we started that year maybe around $10 million in revenue, probably less. </FormattedResponse>
02:31	Sam Parr	Which, six months into the company, you're at a $10,000,000 run rate.
02:34	Eric Glyman	So, let me back it up.
02:36	Sam Parr	Yeah.
02:36	Eric Glyman	We incorporated the company in March 2019. We launched it publicly in February 2020. The pandemic hit; things slowed down, then the ramp started really accelerating. I think that year revenue grew something like 70 times year-over-year. [To be clear: that was from a very small denominator.] We had hit—it was approaching $10,000,000 a year—before the company was even out for a year. By 2021, I think the multiples really hadn't changed too much, but the company ended with an $8,100,000,000 valuation, and we were coming up to—but hadn't yet crossed—$100,000,000 a year in revenue. It was a crazy year.
03:17	Sam Parr	So, how many years until—how many months until a 100 million run rate?
03:22	Eric Glyman	We were one of the fastest ever. I mean, if you go back to it, I think we announced it in March 2022. Paki McCormick has covered the company deeply and become a very good friend. I think she wrote an article about it, mentioning the $8.1 billion valuation. I believe that was in March of 2022. We launched in February 2020. I think we hit our first million run rate sometime in the spring, maybe by early summer. If you look at the traditional charts—it's now become a bit of a meme about time from a million to $100 million in revenue—our chart is actually wrong. It's measured from incorporation. I want to say it was about fifteen to seventeen months from a million to $100 million. It was explosive.
04:12	Sam Parr	"That's insane. I don't even know—I don't know anything about the finance industry, or anything about your guys' business model other than that I use it. Yeah. I know everything about personal finance apps; I'm a huge nerd in that. I don't even know how—like, you take a percentage of spend, I imagine—but I don't understand. Explain to me how that works."
04:32	Eric Glyman	You know, I didn't know anything about it either until I sold my last company to Capital One and learned the business model. In financial services — particularly in the card space — there are two basic business models.
04:45	Sam Parr	Credit cards.
04:46	Eric Glyman	Credit cards. There are two basic ways that they tend to make money. Number one is a transaction-based model, where there's this thing called interchange. Every time a card is swiped, there's a series of payments. The merchant, rightfully so, gets the lion's share. Then the folks involved in moving the money take a little bit. A little bit goes to, let's say, the merchant processor — the people who accept the cards, route the payments, and deal with all...
05:07	Sam Parr	"Who's an example of that company?"
05:09	Eric Glyman	That would be like Stripe or Square—maybe Shopify.
05:12	Sam Parr	And they take a huge percentage, right?
05:13	Eric Glyman	So, they collect it, but they don't keep a huge percentage. </FormattedResponse>
05:16	Sam Parr	Got.
05:16	Eric Glyman	[Explanation of card payment processing fees] You might see headlines on some of these sites like "2.9% + 40¢." At the end of the day, their net take typically varies anywhere from about 1% to 5%, but the gross is much higher because the processor is collecting and then paying the networks. There are several parties involved. First, there's the merchant bank. The payment is deposited to some bank—maybe you keep it there, or you move it to your business's bank account. The processor will keep a little—maybe 10¢. Visa or MasterCard will also keep a bit—call it roughly 1% to 4%. The remainder generally goes to the issuer and the issuer's processor. These are typically the names on your card—examples include Chase, Ramp, Capital One, or Wells Fargo. The issuer traditionally keeps most of that interchange, and the reasons make sense when you think about it. Especially with credit, the issuer is taking on the credit risk. They're effectively saying to the merchant, "We will pay you," even if the customer doesn't pay them back. When the merchant accepts the payment, they are getting paid; if the customer later defaults, that loss is on the issuer. The issuer also bears the operational costs of standing up and running card programs. Historically, these rates used to be much higher. Many of the early rates came from department stores in the early 1900s, when a bank would set up shop inside the store. Interchange could be as high as 5% or 6%.
06:54	Sam Parr	Eighteen months in, at $100,000,000 in revenue, how many employees did you have?
06:58	Eric Glyman	Somewhere between 100 and 200, maybe 200.
07:00	Sam Parr	Dude — that just boggles my mind. My company is, I think, two years old. We're small; it's a bootstrap company and we own the whole thing. I think we have 15 or 18 people. But when you're doing everything yourself as a bootstrap company, getting one or two hires a month is hard. I'm sure at Paribus you were feeling the same thing — the logistics of bringing on that many people. Just the day-to-day: does everyone have a computer? That's incredibly challenging. So if it's 10 people a month you need to handle that, yeah… it's kind of challenging to understand how fast that is.
07:38	Eric Glyman	I mean, now we're over 1,100 people. There can be single, two-week periods when we have 40 to 50 people start. I totally agree with you: you definitely need great software. Even with what you said earlier — like you use Ramp but don't totally understand exactly how it works — there is so much complexity in starting a company, operating it, and scaling it. I think there's an entire class of tools that tend to be great business models. Some of the fastest-growing companies in the last few years have actually been in that space. For example, look at Ramp in the card space: it allows you to scale up and down with full control and full visibility. All your expenses are managed, your accounting is managed — done. You don't need to think about it. In HR and payroll, Rippling is a great example. I think they're eight years old. I think their last round at Rippling... Rippling, you know, in HR they're...
08:30	Sam Parr	"Only 8 years old."
08:31	Eric Glyman	They're eight years old. They started.
08:32	Sam Parr	That's crazy. In, I was one of the first customers, I mean.
08:34	Eric Glyman	They're maybe 2016, maybe '19 — but, you know, they're not that old. I think their last round, I want to say, was at $17 billion. That's insane, right? There are a lot of these tools. HubSpot, you know — you mentioned them — they're an incredible company that takes what used to be lots of little paper cuts you generally need to deal with as a business owner, and abstracts those away. So I think kind of these boring business models can actually be very good.
08:58	Sam Parr	I think I've been able to grow into some of my success a bit because this happens a little bit slower. When you're 32 years old or whatever and you have 200 people, or you have this valuation or whatever, it can still feel a little overnight. Did you have weird feelings of self-actualization? Like, "Oh my God — all I wanted is actually here this fast," and I don't know if I'm actually ready to step into that position or have this responsibility.
09:26	Eric Glyman	There's always impostor syndrome. I would say there are a couple of things. From early on, we designed the company explicitly around velocity. If you step back and look at the particular industry we're playing in — not a joke — most of the founders of the companies we compete with actually wore top hats. They lived in the 1800s: James Pierpont Morgan, Henry Wells. You look at the people who started Amex, Citi, Chase. Nothing wrong with these businesses — in fact, there's a lot to love about them. They're enormous businesses. But a lot of their fundamental edges were long-time enduring brands, unbelievable distribution, risk and underwriting, and the benefits of scale and of time. All of them move very slowly. An analogy I like to use is: imagine you wake up one day and have to use the computer, or the cell phone technology, or the tools that your parents used when they were your age. You couldn't do this podcast. It would be very hard to run your business that way. But if you woke up and had to use their bank account, or their credit card or debit card, you probably could — not too bad. I think that's proof that not too much innovation has happened and that the products haven't fundamentally evolved over the past 30–40 years. We went from no phones to flip phones to computers that can think. So a lot of our view early on was that we needed to count the days, move at incredible velocity, and be designed to ship things faster. Today we're 2,310 days old — six years old. </FormattedResponse>
11:03	Sam Parr	Yeah, that's insane. By the way, you just said that, you know, the day. I mean, that's just, like, a radical thing.
11:08	Eric Glyman	It's... I remember in the early days — when you go back to that eighteen-month period you were talking about at the beginning — we were hell-bent. We set aggressive timelines: within 45 days we wanted to be approved by the network; within 60 days we wanted to be approved by your bank; within 70 days we wanted to be funding our first transactions. We wanted to get this product in front of customers as fast as possible. So a lot of what we were trying to do was just move very quickly. We had set goals to grow the company 10% a week — and once you've got the scale, 20% a month.
11:41	Sam Parr	So, does that do it—burn people out?
11:43	Eric Glyman	It's very intense.
11:45	Sam Parr	"You don't have this typical personality type. Usually, people who succeed as fast as you have are very, very high on the disagreeable scale. You seem pretty easy to get along with, and you're very calm. I don't understand how that personality type has been able to grow this."
12:02	Eric Glyman	My view is: I'm not trying to find folks who are low cost and push them to an extreme—burn them out. I would rather find people who find extreme joy in their craft and set them up so they can be doing just that as much as possible, all the time. But I think that if you want to move quickly, you can't do everything. There are only one or two things you can pick. You try to have extreme focus as a company on those, and every day try to ask, "What are the things we can do to optimize just this one function?"
12:35	Sam Parr	Alright, so I've built a few companies that have made a few million dollars a year, and I've built two companies that have made tens of millions of dollars a year. So I have a little bit of experience launching, building, and creating new things. I actually don't come up with a lot of original ideas. Instead, what I'm really, really good at — what my skill set is — is researching different ideas, different gaps in the market, and reverse-engineering companies. I didn't invent this, by the way. We had this guy, Brad Jacobs — we talked about him on the podcast. He started, like, four or five different publicly traded companies worth tens of billions of dollars each. He actually is the one who I learned how to do this from. So with the team at HubSpot, we put together all of my research tactics, frameworks, and techniques on spotting different opportunities in the market, reverse-engineering companies, and figuring out exactly where opportunities are — versus just coming up with a random, silly idea and throwing it against the wall and hoping that it sticks. So if you want to see my framework, you can check it out — "the link is below in the YouTube description." What businesses were you going to start instead of Ramp? You had just sold Paribus — is it Paribus? Yeah. Have you ever said how much money you made off that?
13:43	Eric Glyman	We even — I mean — talked about it publicly, but it was mid-eight figures.</FormattedResponse>
13:46	Sam Parr	You each walked away with that. </FormattedResponse>
13:47	Eric Glyman	No, that was the total deal.
13:48	Sam Parr	The total.
13:49	Eric Glyman	But we hadn't raised very much. I mean, we had... there's
13:51	Sam Parr	Three of y'all.
13:53	Eric Glyman	It was really Karim and me. We had raised about $2,000,000 at the time, so there were some investors, but most of it went to founders and employees.
14:02	Sam Parr	So it was enough that you're like, "I'm good—potentially good forever, depending on how I live," but I have enough. So you're sitting around at Capital One, doing your thing. What was your list of ideas that you guys were scheming on? Were you like, "It could be this. It could be this"?
14:16	Eric Glyman	"What if it was this?"
14:17	Sam Parr	And this angle—like, was that list? I think everyone has a list.
14:21	Eric Glyman	Exactly. You go through all these different phases. In the first year, we were just dead-set on these people — they had just changed their lives. We wanted to make sure that they felt incredibly good about this deal. So the first year, we actually didn't spend too much time at all. We wanted to make sure there wasn't a "failure to launch" — that we didn't get crushed by the weight of joining this 50,000-person company, and that... yeah.
14:43	Sam Parr	"You're just being a good seller."
14:45	Eric Glyman	Yeah, which I think is good, but it's sort of underrated—the value of integrity and relationships, sure. You know.
14:52	Sam Parr	That was important to me when I sold, too. At 100%, I remember thinking, "I think they got the better of the deal," this or that. But I was like, you know... I'm happy, but I'm also—I kind of want to have a reputation as someone who... yeah. It was a "we all won, we all win."
15:07	Eric Glyman	Exactly right. And I am more flaggative [unclear word]. Like, for folks who are young, you know the value of a great reference—of people saying, like...
15:14	Sam Parr	The world's small man.
15:15	Eric Glyman	It's so small. That was the first year. I think the second year we started saying, "Okay, this is interesting," but I missed the speed. I felt like I was on a cruise ship versus a small speedboat when it came to going and starting a company. I think I did what a lot of entrepreneurs do, which is try to come up with ideas in the abstract. We went on a journey of bad ideas until eventually it came back to good ones. At the time, I was looking at places in New York and they were all kind of bad. We wondered, "Why are they bad?" Cars are manufactured, planes are manufactured—these products are low-cost, affordable, and wondrous; anyone can afford them. Why aren't homes manufactured?
16:01	Sam Parr	So you're going to—you're interested in manufactured... When I was a kid, a bunch of my poor friends and my grandparents lived in what we just called "mobile homes." Yeah. I guess that's what they're called now. The nicer term is manufactured houses.
16:16	Eric Glyman	They're manufactured houses. I mean, there was also — you know — one of the places that is extremely populous, the biggest city in the world, and yet housing isn't so crazy unaffordable is Tokyo. If you go to Japan, it's because most of the home builders are home manufacturers and things are very standard. The cost of a new home build is not that expensive. I think there are all sorts of issues in the States related to this, and we thought, "Wow, we should look into manufacturing homes." I still buy them and think that there's...</FormattedResponse>
16:49	Sam Parr	I've invested in a few of them, yeah. They're...
16:51	Eric Glyman	They're very hard.
16:52	Sam Parr	It was very popular right around when you were starting in Ramp. Yes — I invested in two or three. That space interested me, but none of them have completely taken off.
17:03	Eric Glyman	And ultimately, we decided not to do this for a couple of reasons.</FormattedResponse>
17:06	Sam Parr	So hard.
17:07	Eric Glyman	One — actually, I had no business doing it. I rented an apartment in New York; I never owned a home or manufactured anything. There was no connecting story to it. But the more you read about it, the constraint — the bottleneck — was not around manufacturing at all. It was all the zoning. You could manufacture a house that was zoned to go nowhere unless you could go and see it, too. There were a lot of complex problems. By the way, I hope someone solves a lot of this. I think that there's...
17:36	Sam Parr	"You think that's still interesting?"
17:37	Eric Glyman	I think it's still interesting. My view is it's like the manufacturing is part of it, but the zoning question is very real. It's: how do you actually get...? It can show up in all these funny ways — like which way does the house face? How far back does it have to be set? What are the proportions?
17:51	Sam Parr	Joe Kebbe is doing something in this space.
17:53	Eric Glyman	I think if people crack this, it's an enormous opportunity, but it's a big slog. This is one of those businesses where you're not going to 10x for a while—you'll be growing 10–20% compound. There's a great business to be built there; it's just too expensive.
18:09	Sam Parr	So that was on the list: like a tractor-trailer — I don't even know what you call it. My friends' homes, and my grandparents' home, were delivered on a truck.
18:19	Eric Glyman	Yeah.
18:20	Sam Parr	Yeah — okay. That's the interesting space. What else was on the list?
18:24	Eric Glyman	So that was on the list. There were various, like, random crypto things we were—Kermit and I had been interested in this stuff probably going back to like 2012 and routinely. So we spent a little bit of time around that space. We spent some time helping out different friends who were starting businesses. We were close with Z at Rogue, who started the direct-to-consumer kind of healthcare business, and with folks at Candid. So we spent some time in that world. Then I think where it got interesting again is we came back to the things that we actually knew—back to a bit of our roots. There were almost two variants of what eventually became Ramp. Variant number one is what turned into Ramp, and we can come back to that at some point. The other was this view of, in the card space, which feels almost voodoo from the outside. It's unclear how you start these things or how the business model works, but we knew this because we had spent a bunch of years inside Capital One, studied the models really deeply, knew the history well, and had some credibility in the space. We were also very interested in the partnership business and the co‑brand business. So, let's say you go to Best Buy and at the very end someone asks if you'd like to open a Best Buy credit card—someone is doing that. There are people powering those business models.
19:38	Sam Parr	Who are they? Who's the big one?
19:41	Eric Glyman	You know, Synchrony is a really big name in it. Capital One had a large co‑brand business. Amex — I mean, the large banks.
19:50	Sam Parr	And those are huge—tens of billions of dollars. Barclays. My biggest: Synchrony. I've never heard of it.
19:55	Eric Glyman	MBNA — tens of billions of dollars. I haven't looked up their...
19:58	Sam Parr	In revenue.
19:59	Eric Glyman	You know, that is as well—certainly in market cap, for sure—huge businesses. The basic premise of that is: we had a side of our business at Paribus where we worked very closely with retailers. All of these stores have strong customer loyalty, and credit cards are great products, but they're very hard to sell. So the basic business model was: if you could add—if you're a store with customer loyalty—and you could convert even a tiny percentage of these customers to take on a new credit card, that was it. You would make a little bit of interchange; you would lower your costs when they were shopping with you, and you could also make a little bit back at all the other places that customers went and shopped. The whole question was: could you build a product that was standard enough, simple, and modifiable enough that you could convince lots of different stores? As this was going on, the online boom was happening. Shopify was opening up new retailers and stores everywhere; creators were getting big. We thought there was a chance to have a modern card for businesses and creators. And MBNA was a big company—they figured out, when you look at university credit cards, that's a huge business. Dara Murphy—he's here in New York—his business is doing really, really well.
21:21	Sam Parr	Imprint. I've heard of them — Imprint.
21:22	Eric Glyman	They're doing very well. These take a long time. Even in the cases where they're the fastest ever, you're going to be building these businesses for many, many years. You have to ask yourself: do I want to be working on this for decades? I thought it was crazy that the largest credit card companies on the planet were working really hard to get customers to spend a little bit more than they thought. Then, once they did, they would work really hard to convince people that the points they got were worth a lot—and then devalue them in the background.
21:51	Sam Parr	"It was pretty funny. You said, 'I read so many books on the banking industry,' and you're like, 'I spent weeks doing it.' I'm like, "Oh — I would have thought you would have spent five years." You're like, "You must have read a shitload of books in a very short amount of time." Did you learn about any of the weird or shady stuff that the banking industry does for consumers, or the history of credit cards and things like that? I remember reading about— I think it was Bank of America — was that the first credit card? Yeah. And how, I believe, what they did... Well, first of all, one of them started as a dining-club card. But then another one, what they did was they just handed out credit cards to farmers in Central California — something crazy like that, right?
22:32	Eric Glyman	So the history: it started with a guy named A. P. Giannini. I think it was Bank of Italy — basically Bank of Italy, which became Bank of America. It was started by a very poor Italian immigrant; that's functionally how it got started. His first big opportunity really was the earthquake of 1906 in San Francisco. He was working and kind of supporting and lending to grocers, immigrants, farmers — folks who would come into San Francisco and trade. After the earthquake there were fires everywhere; a huge portion of the city burned down. Supposedly the story goes that he set up a table out in the middle of Market Street and started making loans then and there on the spot. He went from this tiny bank to effectively expanding everywhere. His history is pretty interesting. It was kind of a bank to merchants and then eventually to consumers. In the early 1900s, Woodrow Wilson was supposedly encouraging lots of different banks to go and lend to small businesses and the emerging middle class. This is the thing you hear about: Americans buying their first car, their first washing machine, all that kind of stuff. He was big on it and was famous for setting up franchise banking — little branch banks in all sorts of small cities. They sort of took over what used to be the local lending arrangements, and this is relevant when you get into the history of credit cards. One of the most common places people would take loans was in department stores. If you wanted to buy, say, a washing machine for a dollar, you would walk out after making a 10¢ down payment and pay them back. The banks would say, "We'll take over that Macy's" — you don't need to underwrite each customer; we as the bank can do that for you. And that was the start. Also, you may know that Sears was the parent company to Discover [credit card] in that lineage. </FormattedResponse>
24:40	Sam Parr	"Of it? What would they do if you didn't pay?"
24:42	Eric Glyman	You know, it was a loan, so it was whatever banks normally do. Maybe they could go and take the goods, but it just was...
24:49	Sam Parr	Ah, did credit bureaus exist then?
24:51	Eric Glyman	This was before credit bureaus.
24:52	Sam Parr	And so, what do you do if someone didn't pay?
24:54	Eric Glyman	I think that was why they had the local bankers. You know, they would go and work and try to collect for a lot of years. But that was like early 1900s banking. By the time I was getting to, I think Bank of America was the biggest—certainly the biggest bank in the U.S., and it might have been the biggest bank in the world. It was just enormous, enormous scale. I think the town was Fremont, and this was in the 1950s. It was something like 60% or 70% of everybody who lived in this town were customers of Bank of America. If you were going to a department store, they had a branch that you could go to. But if you were going to any random hard-goods store, you couldn't get a loan for it. So they took this bet: "let's get the rest of the town, let's get everybody." They mailed everyone in the town a card — it was like a four- or five-digit card — and you could go use this and say, "put it on my card," and you would go and pay the bank back later. It just exploded. Almost everyone in the town became customers, and people were using it all the time. Once people got access to credit, they started being able to afford more things. It was good for merchants too: merchants who couldn't access a branch could start to compete with the large department stores that could. It gave rise to the BankAmericard. The initial credit card was the Bank of America card. Once they showed it was successful, they went to competitor banks or regional banks and said, "We will run this program for you. We can issue Bank of America cards for the Commerce Bank of Seattle. You can issue it to your customers and we will deal with the operations — collecting from the stores, paying, doing the underwriting, all that kind of stuff." It was a franchise model; it wasn't the model that it is today.
26:49	Sam Parr	Was that—is credit, like, a uniquely American thing?
26:53	Eric Glyman	I think there's a good argument to say yes. Some of it goes back to that early 1900s lineage. During that time, you saw the birth of the American consumer: department stores, cars (automobiles), and financing for the emerging middle class. I would say, in Europe, even to this day you see very different behavior — where, if they...
27:19	Sam Parr	For example, they don't — they put way more down when they buy a home. And this is exactly it: Americans are very accepting of borrowing and debt.
27:27	Eric Glyman	You know, and I think that's the — that's the perverse way to say it. I think the non-polite way to say it is: in Europe, if you're rich you can borrow, and if you're not, paying cash is all you can do. I think it's actually much harder for people who aren't in the middle class — who are poor — to borrow. In the U.S., there's this view that you can "pick yourself up by your own bootstraps." You can go and borrow for that car, or for that farm equipment, or that laundry machine, so you can build your business and get into it. I think there's a lot of good that comes with it. Obviously, sometimes there's some bad — people can get into credit issues — but I think, on net, for most businesses the startup costs are real, and once you get going you can build an extraordinary business.
28:15	Sam Parr	I listen to founders all the time. I was listening to the Lizotica episode, and I'm really fascinated with building a company that can last for 50, 100, 200 years — something where, God willing, my children want to get involved in some capacity and it could last beyond me. Typically, I think businesses that do that are not the fastest-growing companies, so I actually agree with that.
28:44	Eric Glyman	Like the basic physics of what I think David and the Founders Podcast studies, and what you're getting at too: if you get down to the core of what makes great businesses, it's not about who grew 100% or 200% or whatever this year. It's which businesses can grow 30% for 30 years. If you do that, you will be a giant business. That's not what you did. Our view is that we can. The crazy part is we've grown extraordinarily quickly — we're still about doubling each year at enormous scale. I think we are roughly 1.5% of the corporate and small-business card market in the U.S. So if you just look at the physics of it, even if we were to massively decelerate and start growing 30% for decades, it's physically possible — the market is so big.
29:39	Sam Parr	You're sort of like hanging out with, like, the Illuminati a little bit — where it's these old-money families. That's what a lot of the banking industry is made up of, yeah, because they've been around for 200 years. They've been dealing with money forever. Have you noticed or found anything that you are shocked by, where you're like, "If the consumer knew that this is how this setup is, they would be infuriated"?
30:01	Eric Glyman	There's a lot there in what you're asking. So, one—these families, I think, are focused on doing simple things well and doing them for a very, very, very long time, consistently. A lot of these families just don't sell; they don't fight or interrupt the power of compounding. You want to find a business where you can just compound for a long time. I would say, when you're just starting out—or if you're building and you're terrified of losing money or things going sideways—you have real costs: family, friends, things to take care of. And so you don't interrupt the... [transcription unclear]. You want to—when things get risky—you sell. But I think a lot of these families just stayed in for a long time when there was huge— I mean, classically you'd see a significant recession in the U.S. every seven to eleven years, consistently. A lot of people will sell out at the bottom because they can't take any more pain or they can't take the risk of it going even further. I think the difference with a lot of these families is they would figure out, "How could you avoid it? How could you go and stay in?" You know, obviously none of my family had anything like this, and so I, too, I think as a kid was very skeptical of people who grew up with a lot of money and...
31:20	Sam Parr	One of my favorite biographies is Titan by Ron Chernow, about John D. Rockefeller. Ron Chernow — who's the author — also wrote one on J.P. Morgan, which I'm going to get to. It's fun reading about these old banking families because they're full of stories, and they're typically nutty. You're gonna be an old banking family now — that's kind of crazy to think about.
31:41	Eric Glyman	"It's... you know, does."
31:44	Sam Parr	That messes with you.
31:45	Eric Glyman	I think that a lot of the families of the past have done a great job of being involved civically. I think that a lot of them have been more upstanding—I wouldn't say all of them have been. But I do think that, you know, I'm in my mid-thirties, and I don't know if I thought that far ahead in terms of legacy. But yes, Ramp, as a company, is getting very valuable. All my stock is in Ramp; it's just a certificate. It's only become valuable because we've built something that makes a lot of people a lot better off. My whole obsession is: how do we keep doing that for a very long time? And, you know, maybe the money comes with it, but that's not why I do it.
32:25	Sam Parr	"What was the reason why you did it?" </FormattedResponse>
32:27	Eric Glyman	So, the first company we started was definitely around... I remember when we were down to one month—or like a few weeks—of savings, and that was it. It's the worst. Dude, it's the worst. A lot of it is...
32:40	Sam Parr	Well, usually. But you probably felt that way the whole time — yeah, like that burden. I remember I felt that burden for four years.
32:45	Eric Glyman	"And you're just working your ass off."
32:47	Sam Parr	The worst.
32:48	Eric Glyman	Every weekend, it's hard to relate to her. People—it's like, it's like I remember. </FormattedResponse>
32:52	Sam Parr	In college I had a girlfriend who cheated on me. I remember her saying she was sorry, but I couldn't accept it — it was horrible. She would go out, and I had anxiety all the time. It really bothered me. Then, when I started a business, I found myself constantly checking the bank account.
33:11	Eric Glyman	And I'm like, "I had that same anxiety." I'm like...
33:13	Sam Parr	"I don't want—look, I don't want to go. I just want to bury my head. I don't want to know. I don't want to be part of this." "Yeah, I felt that way for four years."
33:20	Eric Glyman	I'm curious if it changed for you too. After the sale, suddenly you have security, right? Your bank account looks a little more flushed. You move it out of the student checking account to something more secure — now you're good. And then, at some point... I don't know, hedonic adaptation — you get used to it and it's just like a number or an account. Then you have your same anxieties, your same...
33:44	Sam Parr	You have the same shit.
33:45	Eric Glyman	The same stuff — all that kind of stuff.
33:47	Sam Parr	It's better, though—it's better, it's better. But you have similar anxieties. It's not existential... or it is sort of existential, but it's not like the baseline happiness of knowing that you're not going to be on the street. It makes, like, the baseline go up. I agree with all this. Half the time I listen to founders and I'm like, well, every time I listen to founders I think I'm gonna—I'm gonna own this for 50 or 100 years.</FormattedResponse>
34:13	Eric Glyman	Yeah.
34:15	Sam Parr	And then during the day, when I'm having a "pain in the ass" issue come up, I'm like, "We're going to set this up so we can flip this thing." It always changes, right? Your mood... your emotions are powerful. Do you think you'll run this or have equity in it 50 years from now, or would you sell in five or ten years if it was a no-brainer deal? I hope this is...
34:43	Eric Glyman	The last company I'd ever work on. You know, I really—yeah, really, you know, I...
34:47	Sam Parr	"Your partners feel that way."
34:49	Eric Glyman	Yes. Yeah. You know, it's one of these things, too. I remember—even in the early days of going through it—there was deep pain. If you're growing this quickly, what certainly got you here won't get you there. I think some of what Karim is saying is, "Look, if I'm going to go through all this pain like he has..."
35:07	Sam Parr	But it doesn't seem like he went through that much pain if I'm, like, looking at you guys from the outside. Of course it's always more challenging—much harder than it looks. But when I'm like, "I don't know, $100 million in revenue in eighteen months"—like, yeah. Even though it's hard, you're still winning, and that momentum... it's really all about dopamine. It makes you feel good.
35:26	Eric Glyman	Agree with you. So some of it was not planning for downside and not solving problems until they hit us in our first business. In our first business we had a day when we lost 75% of our revenue overnight—vaporized. There were risks we knew about that we didn't properly manage. One of the things in Ramp that we resolved to do is: Kareem and I, and others, are going to beat the shit out of each other all the time—worrying about problems that are three to six months to a year out in the future. If you look at Ramp's trajectory, it has been kind of nonstop growth—fairly consistently up and to the right—in terms of revenue, cash flow, profitability. Those metrics have been consistently good, but it's because inside of it there is so much agony that we spend over things like: this metric that's going to affect how we perform in three months from now—is it going the wrong way? Is it going the right way? What are we doing about it? So it's a lot of internally beating each other up. Often, I think the analogy is an athlete. You look at Wimbledon over the weekend: Sinner and Alcaraz—each of them looked like they're playing effortlessly and can pull off these shots. You don't imagine it's because there's been years and years and years of, when you're not looking, they're just obsessing, practicing, trying these shots. So when it counts, they're able to do it. I think there's a lot of similarities there. For Kareem it was amplified. He has three kids now; he got started earlier than I did, and he's like, "Look, these are some of the most valuable hours I'll ever have." If we're going to go through this, it's going to be because the ambition is real, and if we have a problem we're going to confront it right away. What do you like to read? I like to read. It's part of why I like The Founders Podcast so much—biographies of other founders. I also like reading about design.
37:22	Sam Parr	"What are you, a designer?"
37:24	Eric Glyman	I really like it. So, the first company, ParaBiz, I had design and product report to me, and I had to spend a lot of years thinking about the principles of it — what makes products great. I love it. I would probably get booted off our design team; I don't think I have quite the level of talent in crafting, but I definitely spend a lot of time thinking about it. In terms of biographies — favorites, what am I reading — I think I probably read about 15 biographies of Steve Jobs. As great as people think he is, I think he's still underrated for what he was able to do and how consistently he was able to do it. I also think that he changed a lot over the years. He gets kind of typecast as this "brilliant asshole," which I think he was at the start of his career, but I think he got much more interesting and cared about people in a much deeper way than comes across. Some of that is because people like conflict and controversy, but they forget to look at his career as he softened over the years. I think ultimately that's when he built Apple into the powerhouse that it is today. I've been struggling
38:36	Sam Parr	To find biographies in which I admired the subject's entire life.
38:39	Eric Glyman	Yeah. Have you read— I mean, just on Steve Jobs—have you read Becoming Steve Jobs?
38:44	Sam Parr	I don't remember. I've read about two or three of them; I forget the titles. I did the Walter Isaacson one.
38:50	Eric Glyman	That one is good, but I think that one is more kind of like pop-culture Steve Jobs.
38:54	Sam Parr	It was not. When I remember reading that, I'm like, "I don't want to be this person. I don't like him." Yeah — he was very unlikable.
39:01	Eric Glyman	Yeah.
39:01	Sam Parr	In that book, but what was Becoming Steve Jobs?
39:04	Eric Glyman	So the central question of it was examining who he was over the course of his life. Effectively, these were journalists — people who covered him for about forty years and knew him from when he was a 20‑year‑old kind of wunderkind to, you know, the end of his life. It came out, I think, a few months after the Isaacson [biography], and they felt similarly that so much of who he was portrayed as was this "brilliant jerk." Instead, they were trying to focus on how he changed over the course of his life. I think it's an amazing, amazing read because it focuses much more on him — the lessons and the things that shaped and changed his style. I would say I really highly recommend that book. There are other great ones too on other aspects. I love Insanely Simple. I love Insanely Great — Steve Levy's is a lesser read but a wonderful book, just about, just like...
40:01	Sam Parr	There are 15 of them. Yeah—wow. So ChatGPT has become my life coach. There's a prompt that was like—I forget exactly what it was—but it asked, "Everything you know about me, boil it down to one word." I think I phrased it as, "Tell me my issue or my flaw," so it was going to be negative. I think I said two words: the first was jealousy and the second was fear, which are very similar emotions, actually. I think it was rooted in comparing yourself to other people. In New York City it's so easy to do that, for sure. It's like dialed up to a 10. You're strange to me because you seem... you are so successful at such a young age, and also you seem emotionally stable. Those things typically are the same, you know what I mean?
40:48	Eric Glyman	Little, little out there, yeah.
40:49	Sam Parr	"Yeah, you know what I mean. Yeah, I find that unique and interesting about you."
40:53	Eric Glyman	Look, I'll compete very aggressively in things that I believe in. Don't get me wrong, but when you look back and you're having a shit day, you're like, "Alright, I had a bad morning—what does this affect my afternoon at all?" I've got half a day left. Do I want to make it count or not? I just think the ability to stop, catch yourself, and reset is really important. It's increasingly hard as you get older, but it's super important. I think some of it came from early experiences. My older brother, growing up, would have really strong mood swings and all kinds of things would go on. He had different kinds of learning difficulties and he would take medicine that would radically change his mood. I remember as a kid that was so jarring and weird—someone could feel a certain way and then suddenly feel differently. It was strange to see. As a kid, I don't think I fully processed it, but I remember I'd get really mad too, or I'd be going to sleep angry about something and think, "Why am I mad? Maybe I could not be mad. Does being mad help me or not?"
42:05	Sam Parr	That's an interesting, very, very introspective philosophical question to ask: "Why do I feel this way, and do I have to?"
42:11	Eric Glyman	Yeah, yeah. I think my brother and I would get in all sorts of fights. I remember one—he threw a fork and it went into my leg. When you have three boys in a house, they're probably not as fun as little girls. They do more... interesting things. Our parents—my mom was really good. She'd say, "Alright, I'm gonna sit both of you down. You're gonna have to go and explain." You would listen to your brother as he says why he was mad. You'd get pissed and want to say, "Whatever," but she'd make you say it back to him. Then you'd say your side, and he'd say it back to you.
42:51	Sam Parr	It's a super intentional thing to do. It was really interesting. My parents never would have—they would have been like, "You guys, just shut up."
42:56	Eric Glyman	Yeah, it drove me off the goddamn wall, but after long enough...
43:01	Sam Parr	"Is your mom—like, was she a hippie? That's strange." "No, that stuff wasn't like that. That stuff's popular now with us." "Yeah. That's probably how I'm gonna parent my kid." "Yeah, but that's, like, some gentle-parenting, hippie-dippie shit, which I buy into." "I mean, what was her job—teacher, therapist, or something?"
43:17	Eric Glyman	No — she sold telecommunications. That's interesting telecom stuff.
43:21	Sam Parr	"It's very forward."
43:22	Eric Glyman	It's a way to parent — good parenting, I guess. It teaches you to consider the other side a little bit and to calm down. You see the complexity of things. Later on, when you see something chemically change other people, it's hard to do, but it forces you to start wondering: "Is it me, or is there something going on in my head that's making me feel this way?" I think sometimes stress is good; other times it's not. I think Ramp is a big company — there's a lot of pressure that is natural. If you step back, how you act and how you feel can really impact how you think about things. I think now I'm much more trained, but you spend a lot of time...
44:10	Sam Parr	Do meditate.
44:11	Eric Glyman	What is the headspace? I don't regularly...
44:13	Sam Parr	How are you? This, well-balanced.
44:16	Eric Glyman	I mean, it's a little more trite now, but it's funny — I like Ryan Holiday's work. He wrote Trust Me, I'm Lying, but then he got very into Stoic philosophy, reading Meditations and stuff like that. I think you pick some of that up. I try to have a day where I just hang out — I don't know — go on a run, do different things.
44:35	Sam Parr	To you.
44:35	Eric Glyman	Clear my head, yeah.
44:36	Sam Parr	What day?
44:37	Eric Glyman	Usually Saturday, yeah—usually. Then on Sunday I'll pick stuff back up. But I also think, during your week—especially with other founders—as life goes on, you were probably really good at something and you did it a lot, and that's what allowed you to build this company. Then suddenly you're running the company and you don't have time to do the thing you really liked anymore.
44:57	Sam Parr	Yeah.
44:57	Eric Glyman	I think that a lot of people lose control over their own week, and they don't actually audit: "Am I spending time on things that I'm good at or want to be spending time on?" I pretty regularly try to blow up my calendar and ask myself, "Alright, I actually love doing this thing — am I spending any time on it?" Often the answer is no. I promise, if you spend too many weeks in a row doing something you hate, you're going to be miserable and stressed out. So I redesign my weeks or months pretty regularly. I do. That helps. </FormattedResponse>
45:30	Sam Parr	The question I've been asking myself a lot is: "Where's my weakness now?" What do I need to really work on? Whenever I do reference checks with people, one of my little tricks is I'll ask, "What's this person—one out of ten?" They're always going to say eight or nine; everyone says that. I'm like, "Cool. What makes them a nine?" Okay. Now, to get that extra—what do they need to work on?
45:52	Eric Glyman	"I like this question."
45:53	Sam Parr	"That's where you hear, like, 'weaknesses.' That's the only polite way I've been able to get someone to talk shit on someone. Yeah, which is important, and you're like, 'yeah, yeah.' A lot of those weaknesses they have — I'm like, 'I could put up with that. Yeah, whatever.' Like, if someone's like, 'well, they're really not patient,' I'm like, 'oops, okay, that sounds good to me, whatever.' What flaws or weaknesses do you have now that you think you have to overcome to get to where you want to be in a decade or two?
46:19	Eric Glyman	So I'll slightly critique the question. If you're a one-person company, this is exactly the right question: "How can I change in order to get better?" But if you're a 10-person or a 1,000-person company, or whatever, you're on a team. You can change, or you can change how the team is constructed. I think that's the more interesting way to think about it. One of my big flaws — which is probably very surprising given Ramp's scale — is this: I don't know if there are 100 things to do that are very important to get done. The way my mind works is I'll start with a blank sheet of paper and ask, what are the top five or ten things? I'll write them down and then forget about the rest and not do them. That's fine early on, when there's one or two things that matter. But it will blow up the company if you're consistently not dealing with 90% of the issues. One of the things I do to cope with and compensate for that is surround myself with people who are operationally unbelievable — people who are incredibly good at triaging, at handling cascading issues, at getting things done, and at making things move. What I would say is: it's actually totally fine to have huge flaws. You can decide to fix them, or you can design your life or the company to be performant in that context. A lot of folks look for what they're good at and what they're bad at, and then try to identify all the problems. It's good to know about them.
48:10	Sam Parr	Well, what I'm referring to is, for example: I'm a very emotional person. A trick I've been learning is don't go to the grocery store when you're hungry. Don't make a big decision when I'm feeling pissed off about something, or really happy about something. Don't make decisions then. I have to wait. When someone tells me something I don't like, don't react. Just say, "Okay, let me think about it." My big thing is emotional regulation and impulse control. That's my big flaw, and I have to improve that to be a better person. I'm not even referring to just business, but that will impact it positively as well.
48:56	Eric Glyman	"Yeah, I totally agree with you."
48:58	Sam Parr	Thanks, dude. That's the pod.
49:00	Eric Glyman	Thanks a lot.

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I built a billion dollar company in 18 months

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