Transcript

How Alex Bean Created A $2.5B FinTech Company in his 30s

From Tommy Mello · Episode page · Watch on YouTube

· 48 min · 10,051 words · 88 timestamped sections

This is the full, timestamped transcript of "How Alex Bean Created A $2.5B FinTech Company in his 30s", an episode of Tommy Mello published February 13, 2026 (48 min, about 10,051 words). It mentions 11 people, works and ideas, including Alex Bean, Divvy, Bill.com, Tandem, Factory for Good.

What this episode is about

Alex Bean, co-founder of the spend management platform Divvy, revolutionized financial management for small and midsize businesses by providing tools for proactive spend control, ultimately leading to a $2.5 billion acquisition by Bill.com. His journey highlights the importance of understanding the dynamics of money, both as a power for corruption and a driver for positive change, all while emphasizing that true happiness often comes from simple, low-cost experiences.

Key takeaways

  • Happiness might be a budget-friendly affair; often, the best joys cost little to nothing.
  • Divvy's $2.5 billion exit proves fintech disruptors can prosper from everyday frustrations—who knew receipts could be so lucrative?
  • Transforming business spend management showed that visibility can be more valuable than money itself.
  • Great ideas often come from pain points—Divvy was born from the chaos of expense reports, not a finance degree.
  • In venture capital, product-market fit reigns supreme; even the best founders can’t mask a poor fit with charm.

Who speaks in this episode?

What is discussed, and when

  1. – 5:00: Alex Bean, Divvy, Bill.com, Tandem
  2. – 10:00: Tandem, EOS, Geico
  3. – 15:00: Tandem, Jeff Bezos
  4. – 20:00: Atomic Habits
  5. – 25:00: Tandem, Factory for Good, Die With Zero
  6. – 47:59: Factory for Good, Tandem

Notable quotes from "How Alex Bean Created A $2.5B FinTech Company in his 30s"

  • Welcome back to the Mellow Millionaire.
    about Alex Bean · at
  • Divvy and Brex who just sold for $5 billion or you got RAMP, you have AMX and Capital One. All the players in the business are now basically moving their credit card spend…
    about Capital One · at
  • Money. And then they've got to give me like their one to two sentence. Here's what we do. And the best example in the history of the planet is in 15 minutes or less, save 15%…
    about Geico · at
  • So I had Cass and Mike Lazero on and they sold golf.com for $750 million and I also had Gino Wickman on several times and EOS. I'm sure you're familiar with it. Same answer I…
    about EOS · at
  • Built and now he starts work at like 11 and finishes at 2 p.m. Main decisions he makes. He built an amazing team. Do you ever think you jump back in the saddle?
    about Jeff Bezos · at
  • It's funny. This is before Atomic Habits. obviously, you've read Atomic Habits. the concept of the 1% change is life-changing. I got advice from.
    about Atomic Habits · at
  • Yeah. it's it's tough because I think we're all money driven, but at what point there's a great book I just read, Die with Zero, and it just explains like live your best life…
    about Die With Zero · at
  • If you have exited or about to exit, we have a bunch of content, a bunch of interviews, a bunch of experiences designed for you. It's all free. It's my nonprofit. We are working with.
    about Factory for Good · at

Who and what is mentioned in this episode?

People

  • Alex Bean — Person · Main guest · 2 mentions · first at
    Primary interview subject; discusses founding Divvy, its acquisition, his VC work at Tandem, and post-exit purpose/philanthropy.
  • Jeff Bezos — Person · Referenced business figure · 1 mention · first at
    Used as an example of a founder who built a team/system enabling fewer hours and focus on high-leverage decisions.

Books & papers

  • Atomic Habits — Book · Referenced work · 2 mentions · first at
    Book mentioned in the context of building good habits.
  • Die With Zero — Book · Referenced work · 1 mention · first at
    Book mentioned in the context of living life fully and giving back.

Companies & orgs

  • Divvy — Company · Business focus · 1 mention · first at
    Primary company discussed, a spend management platform acquired by Bill.com for $2.5 billion.
    Giving operators tools to control spend before it happens. That vision ultimately led to Divvy being acquired by Bill.com for $2.5 billion, making it one of the most…
  • Bill.com — Company · Acquirer · 1 mention · first at
    Company that acquired Divvy for $2.5 billion.
    Today I got Alex Bean. He's a managing partner at Tandem, the co-founder of Divvy, that spend management platform that thousands of fast growing companies rely on to bring them discipline, visibility, and control their finances.
  • Tandem — Company · Current affiliation · 5 mentions · first at
    Alex Bean's current venture capital firm.
    Today I got Alex Bean. He's a managing partner at Tandem, the co-founder of Divvy, that spend management platform that thousands of fast growing companies rely on to bring them discipline, visibility, and control their finances.
  • Capital One — Company · Competitor · 1 mention · first at
    Mentioned as a competitor in the fintech space.
  • Geico — Company · Case study · 1 mention · first at
    Mentioned as an example of clear marketing messaging.

Products & tech

  • Factory for Good — Product · Nonprofit initiative · 3 mentions · first at
    Alex Bean's nonprofit focused on helping founders navigate prosperity.

Concepts & topics

  • EOS — Concept · Referenced framework · 1 mention · first at
    Entrepreneurial Operating System mentioned in passing.

Full transcript with timestamps

So, I I call it the happiness audit. I would actually go through and I would do this. I would write down everything that makes you happy. And then I would say, "How happy does it make you?" And I would I would be honest with yourself. How long does that last? What was crazy to me? Things that brought me the absolute most happiness. Almost all of them were free or costed a $1 sign, meaning it was like anyone could really afford it.

Our guest today is a founder who helped redefine how small and midsize businesses manage money at scale. Alex Bean is the co-founder of Divi, the spend management platform that thousands of fast growing companies rely on to bring discipline, visibility, and control to their finances. I saw how money both corrupted and enabled people to do amazing things. Because of that, I just feel like I was always cognizant of the power of money as a kid.

Before Divvy, managing company spend meant chasing receipts, fighting fires in accounting, and finding out problems after the money was already gone. Alex helped flip that model on its head, giving operators tools to control spend before it happens. That vision ultimately led to Divvy being acquired by Bill.com for $2.5 billion, making it one of the most significant fintech exits in the SMB space. This one's for the business owners who are sick of sweating over team budgets. Welcome back to the Mellow Millionaire.

Today I got Alex Bean. He's a managing partner at Tandem, the co-founder of Divvy, that spend management platform that thousands of fast growing companies rely on to bring them discipline, visibility, and control their finances. So, you co-founded Divvy, and you sold it to Bill for 2.5 billion, 5 years later. That's why I love fintech, man. Can you tell us a little bit about that, how you got into that space, and um you know, where you got where you're at today?

Yeah, I mean, it's uh it's funny. We never and we didn't have a fintech background. My partner and I, Blake, we were running small businesses and and basically we had kind of that experience everyone has with expense reports where they kind of swipe their credit cards and then ask for forgiveness later. And he was running uh some pizza shops and I was, you know, running kind of a custom dev shop. And we sat down and said he actually came to me and he's like, "I got this idea. I want to dippy out my credit card." That was like his his brainchild. And we talked about it from a consumer side and from a business side. And within an hour, we had kind of mocked up, well, what if we could put it on the phone, right? Like create a Venmo for business and Apple Pay and all this stuff. And uh we talked about it for an hour. And I think we never stopped talking about it again for the next six months until we officially did it. And

uh it was it was a wild wild ride. And we got our butts kicked in some regards, we kicked butt in other regards. And uh it was it was a fun run. But it took us 5 years and it's now been about 5 years since since we did it. So it it feels like an eternity to go but also feels like yesterday.

Yeah, that's a big business in 5 years. I mean most people spend 20 years to get to that size. Um what was your favorite part about building Divvy from the ground up?

So if you really think about what we did, it was changing the way that businesses spent money. And so our our tagline was spend smarter. And we wanted everyone from like the owner and the managers to the employees to just have a little bit more visibility on how much they had in their budget and what they could spend. And to me, I think the thing I'm most proud of, banks didn't even do live reconciliation with transactions. So the idea of like an a real time budget like just didn't exist. And so now fast forward, you've got Divvy and Brex who just sold for $5 billion or you got RAMP, you have AMX and Capital One. All the players in the business are now basically moving their credit card spend towards what we came up with. You know what's funny is I think I might have been the original first customer cuz it had to be five years ago. I've been on Divvy forever and I just like the concept of, hey, I'm

going to give you your card, but it's really monitored in a different way. We've got a lot of employees with expense stabs and you know, I'm finding out private equity. There's one I have in mind that they don't really have their stuff really tight and there's I found out there's a few executives there that have paid for their golf course membership, like literally like hundreds of thousands of dollars. And it's such a big company. I don't think people realize it, but you know, my CFO loves it and it's so important. Um, what do you think being an operator of that shaped how you look at the business world today?

Well, one thing that we so like now I'm in venture capital. Okay. So now I look at a lot of early stage businesses and the thing that shaped me from my Vivby time to my lens now is like early early on I almost care about two things. One is I do care who the founders are. I'm curious their background why they think it's they're there they're there the choice. But let's get rid of that for a second. I think the most important thing at the very beginning of a company is product market fit. And I look back at the Divvy days and people say how do you know you had product market fit in the early Divvy days? And I'm like, well, I was at a job where I was actually making very very good money. We were we were kicking butt in our own right and um it was going well. And I we were flirting with this idea of Divvy and I start we took a mockup like not like not a real product at all and I started to like

call people and I said, "Hey, here's this here's what we're thinking about building and called you know CFOs and head heads of finance." And the physical response I would get from these heads of finance of like, wait, like I'd show them like, hey, you could send 10 people to Vegas and give them a budget and they would like freak out. Like their heads were exploding like wait, what? Like that's possible? And and I was like, oh my gosh, like they like really want this product. And so even when we launched the product, um it wasn't actually a great product. Like at the beginning it kind of sucked. Um, in fact, I know it sucked, but we call it the the dogs wanted the dog food even though there's a bunch of hair in it.

And uh, we had product market fit and it flew off the shelf. And so now when I look at these early stage companies, I basically ask myself, why do you think you have product market fit? Why does the uh, why do you think the the world wants what you're building? And to me that discussion and we could talk more about it but that discussion of product market fit is heavily shaped you know what businesses I would invest in what businesses I would go into you know if I started one again and and that's a big component of it.

You know I had Gary Vanderchuk on last week and he goes dude my early days of VC he goes man I got my ass kicked. He goes I figured out you know because they're all from Harvard or Stanford or Princeton. a lot of the guys we invested in. And he goes, "Now I have to see a physical product. I'm not going to invest pre anything." He goes, "I need to see it working." And that's what he told me. What are your And I love VC because you don't need to hit uh most of them. You just need to hit one home run. What are some of your best pointers?

What else do you look for? How well does that person know their who they're building for? Right. A lot of people come up with this cool idea and they're like, I'm going to build this red cup and people are going to love this red cup and they kind of get obsessed with the idea themselves and I'm like, I don't care what you think of the red cup and I don't care what your mom thinks of the red cup or your friends think of the red cup. I ask them to go through a billboard blurry. So I I basically say, hey, like these three questions and I'll have a better understanding if if they know who they're really building it for and why. So the first question I'll ask is who you building the red cup for? And they have to be very specific. So I'll just use DV as an example. And it'll be like, well, we are building for heads of finance for companies 50 to 500 people.

Like, all right, that's your ICP. That's where the billboard's for. Great. Are you saving them money, making the money, or saving them time? What do you, let's just play a fun game. What do you think is the worst answer of those three?

I would say making money. Okay. What do you think is the best answer when I ask that question?

Saving time. Okay. Uh the worst answer is when people say all three. It's like the absolute just worst answer because it's like, well, hold on, hold on, hold on, hold on. You can't just say it does everything. You need to tell me why that target market wants your product. Um ultimately though, you need to know exactly what you are. So for us at Divy, we would have said we are saving them time. Now we're also giving them control over so saving money, but we're we're we're saving them time. And so then I say,"Well, what is your uh billboard?"

The third phase of this is like, "Tell me how you're going to tell that target market how you're going to save them time or how you're going to make them money." And then they've got to give me like their one to two sentence. Here's what we do. And the best example in the history of the planet is in 15 minutes or less, save 15% or more in car insurance. I mean, like Geico knows exactly what its billboard is. And uh so yeah, we go through that uh that exercise. And to me, it's such a simple exercise, but when people can't answer their ICP and they can't answer what their motivation is, and then they can't give a credible answer as to why they're doing either of those two, then they they don't really have a company. So, to me, that's a very simple test at the beginning of of someone's uh world to say, hey, do you know what you're doing and why you're doing it?

How many companies have you invested in post Divvy? Uh 30. uh you know some personal but I would say Tandem has done around 25 and I've done a handful myself.

So I had uh Cass and Mike Lazero on and they sold golf.com for $750 million and I also had Gino Wickman on several times and EOS. I'm sure you're familiar with it. Same answer I get from everybody. This emptiness when they sell it's almost like part of their DNA and a lot of entrepreneurs. There was a guy recently that sold this company for $3 billion and I don't remember who the podcast was but he bumped the the the guest I had on bumped into this guy and he said I'd give back the $3 billion in a heartbeat two years later to get my company back. Well, it's this emptiness because you want purpose, I guess. What are your thoughts on that?

Yeah. So, it's funny you say the uh you get you you I used to say I used to joke my wife would have would press the button and when I me you remember those old staple easy buttons, those little red like you know buttons, you know, and I'm like it was for a while and it's probably changed now, but like for a while my wife would have pressed the button to just go back to the way things were. But it's not just her, it's me, too. And what I felt was so we sold in June and like when I we sold like June fourth or fifth or something like that and I was gone like the next day, right?

So we sold I left. Summer was great. Honeymoon phase for sure. Trips, time of family, detox, all that stuff was great. Come school, my kids I have four young kids. My kids go back to school. Um my friends are still at Divvy and it was probably like October at this point. And I remember like in bed at night with my wife and I said, "Uh, Megan, I'm going to tell you something that just s that sounds crazy, but like obviously I you know, you're my wife. If I can't tell you, I can't tell anyone." And um I said, "I'm jealous of my friends in the rat race." And she was like, "What are you talking about?" And I'm like, "No, no, no. know how that sounds cuz I the grass is greener on the side of of money, but I'm like I I'm going to bed and I didn't feel like I earned my sleep today. I didn't feel like I built anything. I mean, like I played golf, I had lunch, but like I didn't I didn't build something. And to me, it was it

was a fascinating realization that uh although I I'm super grateful for the situation my family's in. I was jealous of my friends that had the like every day they had to wake up and then they went to work and they came home and they had this feeling of like I put food on the table. I worked hard today. I did what I was supposed to do. And it was just um it was more empty than I thought it would be uh in that scenario. And I was like I needed something. I needed purpose again as you said. And so it took me a while to figure out what that was. And it was kind of shocking frankly to to find myself in that position.

Yeah. I So I sold half of the company at the end of 2022 and luckily they kept me as the CEO and I'm still somewhat in charge. They could trump certain things but rarely do they do that with a founder. And uh you know my fiance said, "Well, what's the plan?" I'm like, "I'm going to roll again on the next turn." I'm like, "This company's got so much growth potential." But I always think about, you know, I could probably do golf and do the beach for a couple months, but I just hear these horror stories like you could only do that so long, especially if you're like the the slim 5% of entrepreneurs that just need to continue to go go. U would you would would you go back? I mean, would you continue to ride it out? I mean, I know that's a really tough question.

I would actually say no. I'm glad that we sold and I'm happy that we sold. And if I were talking to another entrepreneur, I would say I'm not my what I'm telling people is not, oh, you can't sell or or don't cash out. What I would tell them is like just know you're gonna have to go find another mountain to climb. And it might be in the nonprofit space. It might be in a religious space. It might be in the capital like business. I I don't care. But you're not just going to go from like crazy, you know, energy and and and motivation to all a sudden like, oh yeah, I'm just going to I'm just going to take a, you know, time off and do nothing. So to me, I'm glad we did sell.

I missed it. But after the evolution of like, you know, it took me about eight months to find what I was going to do next and eventually started uh Tandem, the venture capital firm, and then eventually started, you know, I started writing the book. And I had to go through some uh iterations to figure out what I wanted. But I'm glad I did it. But it still was a very it was still a long process to get to where I wanted to be. And now I'm I love what I do and I feel very, you know, purpose driven and uh but it's not at the same pace that it was at DBY. So it's been a nice trade-off now to like still have purpose but not have to run at the same, you know, stress levels that we were running in.

I think about Jeff Basos of what he built and now he starts work at like 11 and finishes at 2 p.m. Main decisions he makes. He built an amazing team. Do you ever think you jump back in the saddle? So, people ask me this a decent amount and they said, "Is it easier to be the investor or the operator?" And I'm like, "That's honestly like a dumb question. The answer is an operator is so much harder." Um, the stress is just constant. Uh, as an investor, as you said earlier, you don't have to hit every bet. You're not trying to hit a quota every single month. You can you can place your bets and and and and go.

Um, I've thought about it. I think if I were to do it, it takes a lot of energy and ultimately like what it, you know, you'd have to go build a great team. So, it's possible, but honestly, I don't know if I have the energy to do what we did at Divvy again, just the the the speed of which we were running and the effort we were putting in. I know I don't have that in me right now. So, um maybe if it was a slightly different industry that wasn't as competitive and as big of an opportunity, then they'd be like, "Oh, I can go build something."

But not that. Again, I don't I'm not that that good. Yeah. Did you see that interview with Alex Ramoszi and uh Tony Robbins?

Yeah. Where he's just like, "Dude, you just work." He's like, "You don't enjoy it. You're just living to work." And that's who Alex is. And I think about that and I'm like, "Man, I love my life." You know, there's so many fun things we do. I think when you're in the heat of building something special, it is a lot of work. I mean, there's no there's no denying that. But what's the happy balance for you? Uh obviously, you got four kids. you're happily married. Uh what was that like and where do you think the like how do you balance that?

When I was at Divy in the heat of it, I my schedule was like this. I anything before 8:00 I considered my time. Meaning if I wanted to work out or play golf or any hobby, I did it before 8 o'clock. I'd get to work by 8 o'clock. So, you know, get to work at 8, uh, work till probably 5:36, but I'd be home for dinner by call it 600 6:30 and uh, yeah, call it 6:00 to 9 was family time. So, eat dinner and play with the kids and then usually by 9 kids were back asleep and I'd be working again from 9 to probably midnight or 1 and then, you know, uh, do it again. So, um, that was just my schedule and, you know, it worked thought I had a little bit of me time. I had some family time slotted in and obviously a lot of work, but um that's that was the schedule I ran when at Divvy for the most part.

I want to ask you three repeat questions, but I'm going to add a fourth one here. Uh if you go talk to yourself, call it right before you started Divvy, what advice would you give yourself? I I ended up kind of having a phrase at the end of Divvy and I and I think it's the the advice it's the advice I give a lot of founders and it's the advice I would have given myself. Um and it was things are never as good as they seem and they're never as bad as they seem. And in a startup it's like constantly true. And the way I would explain that is like there are days I would come home and I'd walk in the door and I just look at my wife and be like we've done it like we are we are going to be huge. This is awesome.

day or two later, I'd come home and be like, "It's over." Right? Like some compliance thing or some, you know, whatever thing. And um the highs were pretty high and the lows were pretty low. And I would just I I would I would say to myself that and be like, "Enjoy the process of of going for it. just enjoy these moments because eventually it the cat gets out of the bag and it's like just a whole different feeling and more and more people and it's great but it's also totally different. So enjoying the process for every stage that you have and um trying not to to to go crazy with the emotions but

or what's one piece of gamechanging advice you wish you knew in your 20s? So, I got advice. You know, it's funny. This is before Atomic Habits. Like, obviously, you've read Atomic Habits. You know, the concept of the 1% uh change is life-changing. I I got advice from someone actually my my business partner's dad before we were business partners. Um we knew each other back in Seattle and I was interviewing about about my career and I said, um you know, what advice would you give me? And he said, "Good habits go a long way." And what he's saying is the atomic habits message which is just like build in some good habits and just slowly start stacking better good habits good habits and good habits and eventually you've built someone who's you know efficient goal oriented um with the right processes in place to keep getting better and I would say I'm okay at it like I'm not the best in the world at it

but it was phenomenal advice and to me going back into my 20s I and I I I have a bunch of nephews and nieces and you know I work with a lot of young entrepreneurs and I think that that advice still holds true which is just stack good habits and keep making yourself better and better. 20s has nothing to do with making money. It has everything to do with stacking capabilities, learning art skills and learning good habits. The money will come in your 30s, 40s, 50s if you if you do that.

I agree. Uh, if you had to start over with 10 million tomorrow, where were you putting the 10 million? Per

personally, if it was like, okay, if I had 10 million and I was like trying to, you know, go back and and create uh a different level of wealth than that, I I would start a business. I would probably take I mean, I'm a risky person by nature. I don't want to say I have the exact idea, but I'd be like, "All right, there's a few phone calls to make." I'd call a few a few people I know and be like, "Come to my office tomorrow. We're gonna figure this out. Uh we're going to spend a solid 70 to 80% of what we have in this bank account to see what what business we can go create." Cuz if you're going to create wealth, you do it through creating a business. Like to me, you got to go create and build something. And uh so we'd start from scratch.

What's your biggest professional dream at the moment? So I'm I'm money motivated for sure. Sure, I don't want to we're going to get into some of this nonprofit stuff and I don't want to uh anyone to think that I'm like anti-money or I'm against that motivation because it was my motivation for a long time and I'm not against the motivation. I think it's a good motivation. I remember driving in the road with my partner Blake and he was kind of giving me the like what's your number speech like what's your profess what's your what's your mountaintop and I gave him this number and it seemed not crazy but it seemed like wow if I could hit that number that that'd be unbelievable and um you know fortunately with Divvy we we we surpassed the number and and that was great and and so now I look at it I'm like well what's my my professional goal is no longer like oh man I want to go hit this number, I got

to get this big. Like I I think I've been able to get past that kind of mindset. And now to me, like I started Tandem, this venture capital firm, because I was like, if I can go help 10 other entrepreneurs have a divy- like experience here in Utah or uh around the US, that to me is a professional goal. Like, if I could go find 10 more entrepreneurs to sell unicorn companies, I would I would love it. Like give them my playbook, have them go be 10 times bigger than me, that would be awesome. So, um, I don't really have like a own personal mountain I'm trying to climb other than, you know, maybe help a few other entrepreneurs along the way and work with great people and and do what I can to to build some companies.

Yeah. I mean, it's it's tough because I think we're all money driven, but at what point there's a great book I just read, Die with Zero, and it just explains like live your best life when you still can. Don't wait to give it all away when you die. You know, give along the way. Start charities, start 5013c's, do the trips, do the family trips. Uh I don't have any kids yet, but I'm going to have kids. And I heard days are long, but the years are short.

Yes. So, let's talk a little bit about postexit life. You you wrote the book Factory for Good. Uh it came out of a very personal place. Obviously, you decided the definition of success had changed and uh you want to help other entrepreneurs, but it sounds like you really want a lot of the stuff I think you talk about is what happens after the money comes.

I wrote the book I I grew up I had a successful great-grandfather and a successful grandfather. They were entrepreneurs in their own right. Awesome, you know, entrepreneurs and business people up in Seattle, which is where I'm from. And uh so I grew up around it. I grew up around watching wealth being created and jobs being created and um without going into the the personal details, I just I saw the positives of money and the and and the community things you can do and the people you can help and and my own father was helped because of this. But then I also saw the negatives of money and and all the things that come with that and and um I remember watching uh my you know I just remember watching my grandpa who was like one of my idols. I mean he's just the man. He had everything. But I realized that money wasn't just the secret to success or secret to happiness and there had to been something else. So, you know, when

the money came and it hit the bank account and I was processing it, it was like, wait a minute, how do I make sure I end up over here and not over here? And I I make sure the good things happen and this is a positive thing for my family and not a negative thing. And so that that just like hit me like, okay, hold on. What are the small decisions I can make? And so I started interviewing hundreds of people of just like, what have you done to navigate good and bad the roads of prosperity? And from that came a lot of really cool stories and a lot of uh help in understanding like yeah what do you do when the money comes and and uh I learned a fair amount from those interviews.

You know I had a mentor we kind of did everything we could together. I was his last client but Dan Martell buy back your time and he he got me to look through a different lens a lot about money but he's like you got a chef right? And I'm like dude no I'm a blueco collar guy I don't have a chef. He said, "Well, do you like to cook?" I'm like, "No, no, I order Uber Eats." And he goes, "You got a driver, right? You drive." We went over this whole thing we went through and he's like, "You drive 11 hours. You got a driver, right?" I'm like, "Dude, a driver. If I showed up to work with a drive," but he's like, "That's selfish." He's like, "Think about all the Zoom meetings and the things and how much gratitude and you could tell people how great they're doing on those on the car rides." And he really got me to look through a different lens and just about doing things for so many people that I care

about. So, I made a list of every single person, a lot of family, a lot of other people, and I don't want to give them anything, but I want to give them opportunity. Like, I'll invest in them if they got good ideas. How do you feel? Because Kevin Olirri once said, "If you need money, you get one time. I'll get I'll cut you a $50,000 check. You could never come to me again for money." How do you deal with that?

Actually, what Kevin said, which I think is interesting, is let's use a fake number, but like someone says, "I need a 100,000." He would give them like 130 or 150. He gave them more than they asked for but said this is your one time. And I I actually uh I love that that thinking because you know look I get it like there's a lot of people like in your world that are going to say I need help. I need help. I need help. And and a lot of people are well-meaning and they need help and you give it to them and they go execute and they they get on their feet and and it's a win-win and it feels great to give and they are happy to receive and get back on their feet.

But there's a fair amount of times where that's not the case, you know, where someone just kind of wants to to grab what they can and it it can be difficult to um parse the difference. And one of the things that stinks, my my brother who helps me run a family office kind of said, "Does it is it going to change Thanksgiving dinner?" And that's one of the things that stinks is like sometimes you can give money to a loved one and then when they don't do what they said they were going to do or if they lie about it or if they basically throw it all away, you're like, "Well, now like this was a relationship we had and now it's kind of like totally disrupted because you just took the money and and didn't do what you were going to do." So is it's way more emotional than people think. And I think that that caught me off guard. I think it it felt like, oh, I could just give money over here and it

wouldn't affect my personal life and and it has a decent amount. But I actually like the Kevin Olri strategy and I I've I've done it a decent amount and I think that that's that's that's one I'd recommend for sure. By the way, I do love the die with 0ero2 because I'm I I was talking to my dad who, you know, he has he has some money but nothing crazy and I'm like, "Dad, don't wait till you die to give it to, you know, a kid that's struggling or, you know, someone else that you want to give it to. like go look at go give it to him and talk to him about it and like don't wait till the trust and and so it's been fun to watch him trying to learn how to like no let's let's spend it not just constantly save it and I think most people that are inclined to build look at their net worth and they they want to see it constantly do this and the thing about dive zero that I like is he's like hey it's okay if that number starts going

down for whatever reason whether it's experiences or nonprofits or you know what have you and uh I I think that that's a good notion for all of us to have.

How do you feel about possessions? I mean, you know, I'm building a really nice house in Idaho and I took my dad up there and and the deal is my dad went up there and he's walking around. It's a massive house. He goes, I never want you to feel guilty about your success. He goes, you're not using this to say, "Look at me. You're building kind of a melting spot for us all." And I know that's you. You're never gonna have a day alone on this lake without family, friends, co-workers. But what are your thoughts?

You will have haters no matter what. I mean, no, it doesn't matter what you decide, you'll have it. But uh okay, there was a book I read called Thou Shalt Prosper by a Jewish rabbi Daniel Lapen. So, I'm not Jewish, but this um this um rabbi wrote the book and it's actually I love some of his thinking and some of his his me his messaging, which was God wants us to prosper. He want money is a facility a facilitator of buying things what things that we need like food but also experiences and shelter and safety and um that changed a lot of my opinion on like the the blessings and purpose of of money. I really like that book. And then how I try to play that out is look, I do think that things can take over and people can get um um caught up in consumerism and like what car what car can they get, how many cars can they get or how many houses and and I think it's it's more of a I'm not against those, but I'm like, hey, are

you building a place for memories, right? Like I I'm with you. I we have you know actually here here's how I would respond to that. I did hundreds of interviews with people with money and I asked them what's the number one thing you've done with money that you would definitely do again that you absolutely love and the number one answer almost every single time was basically buy a cabin or go on trips with my family the because it was like I'm creating memories with the people I love the most and I get to experience things with them and it was just like every single time.

Um, now there's a fine line, a fine line between that and just, you know, like I'd say the difference between rich and wealthy is, you know, if someone's on a a private plane by themselves, that's rich. Wealthy is the person that's on the plane with family and friends and and and have those relationships. So, make sure that you are actually maintaining and bringing in those relationships and you're not doing it for yourself. And if you can balance those two, then I'm like, yeah, go for it. That's great. What emotional challenges around money do most founders never talk about publicly?

I didn't put this in the book um but but it's it's it's it's a very it's a good example of the emotions of wealth and I'll give you two things. First thing is like okay so who's the most important person in my life? my wife, right? Like she's everything to me, I'm everything to her. And um what was fascinating is we'd been married for 14 years when we exited Divvy. Great relationship. I think we both had give it like an A+ where it's great spot. But when the money hit, I was like, "Let's go this way." And she was like, "Let's do this." Like I said, she would have pressed the easy button of like, "No, no, no. Let's go back.

Let's not do anything different." And I'm like, "Let's go get a cabin." All this stuff. And for the first year after divvy, it was probably the second hardest year of our marriage outside of the first year because we just the emotions of money hit us so differently and how we handle it, how we handle family, how we handle giving to people, how we handle responsibility of it, how we talk about it, how do we raise our kids. And it created a lot of conversations that we just uh I didn't realize that they that we were so we were so different. And um it took us a long time to to see each other's side and process it. And to me it was kind of odd that we found a divide from the money. So that was very emotional and took a long long time to work through.

I think the listeners I think a lot of them have healthy exits coming and I think your life partner is one of the most important people to discuss that with on how it's going to be spent maybe before the transaction. But I'd love to hear a little bit more about that.

Yeah. So, I'll give you like a I'll give you a practical example of what I'm talking about. Um, we lived in a nice house, you know, a reasonable house, uh, starter homeish, but we loved it and our kids loved it and the kids had friends and we lived next to family and it was great. Um, but, you know, you get money and you're like, "Oh, we should go build maybe a bigger house and this bigger house could have some fun things like a basketball court or whatever." A pool in the backyard. There's a pool. And um I'm like, "Well, let's go do that." And she's like, "I don't want to change anything. I want to be next to family and I want my kids to stay at their school and I I want I don't want change.

I want my kids to grow up in this environment." And I'm like, "Well, but I want to go have this environment." And they were very different environments. And so for us to have to con constantly talk about what was right, what was wrong. And by the way, there is no right or wrong really. It's more of like we got to just be together and figure out what's best for us and our and our family. And so eventually it was like, you know, we actually bought property, but we didn't end up building on it for a while, but eventually we were like, okay, let's start building. And these were just, you know, they're they're seemingly small. you think, oh, you just go buy a house and because you can now afford it, but it was actually like the ripping of our kids out of their school to go to a new place and yes, we are in the new house and it's great and our kids have new friends, but it it was a big discussion and a lot of uh

questioning from my wife and you know the kids, is that the best thing? And so, um it's not as easy as just go buy the house and enjoy the pool.

I'll never forget December 2022. It was Christmas day and the money had got wired to my Goldman account and I called Joe, the guy at Goldman, and I go, "Dude, this is a weird feeling." Like, I'm looking in my Goldman account, and I go, "Dude, I could never imagine being able to spend this much money." And he goes, "Dude, I know you. You'll spend it." I mean, a lot a lot like you. I I like to invest in things and like to see things and to grow and just be part of stuff. So when you thought about real estate, you got venture capitalists, you got hedge funds, you got conventional private equity, you started a family office, there's Bitcoin, there's the S&P market, you know, and they say get diversified, have slow money, have long money, have your money that you want to kind of experiment with. How did you land on your strategy? My my brothers actually helped me run, they were running a wealth management firm, so now

they kind of run my family office. So, it's amazing to have older brothers that that can I can trust. They basically handle call it third or 70%. Um, and there's about 30 maybe 20 30% that's um that's more so I handle the private equities. I handle kind of the investments into things like you venture capital and private equity. They handle public equities and real estate and kind of like the traditional we'll call it long money. So, um, we just kind of come up with that balance 7030, 8020 of you guys, make sure that my family is good and, you know, I'm not going to get too risky, but I am going to take some of of the slice and play with it and get my hands dirty and and, you know, test my stuff. So, that's largely what we've done. You know, there's certain things I'm much heavier in than others, but I'm not saying my way is right. It's just how we go about it.

I think the largest thing when you get a lump sum of money is uh, how do you beat taxes? I mean, literally, that's like it's long-term strategy with trust, real estate, accelerated depreciation. Um, you know, one thing I really, this is a selfish question, but you know, I'm thinking about my future kids and I'm thinking about, man, I didn't have a pot to piss in. I mean, we went shopping in fall for clothes. It's not like I didn't have clothes or food, but I mean, we lived in a small house. Mom worked three jobs. I mean, and I think that's what made me.

So, by the way, the reason my wife and I are very different is my wife grew up in a similar situation. Mom, single mom working, you know, all the time and and six kids and, you know, it's like I grew up in a different scenario where we were upper upper middle class and, you know, we had a pool in the backyard. So we had different backgrounds and uh I see this all the time and in the interviews of people be knowing like hey I had to work when I was 14 and that's what made me but now my kid only lives in a certain lifestyle only stays at the four seasons like what what's what's going to turn of him and honestly it's um it is complicated. I don't have a right answer. I will say in that world of we'll call it trust fund kids or or kids that grow up with wealth, I see a ton of kids that get screwed up and I see a ton of kids that are some of the best kids I've ever met. And usually I I tell them

if your kid ha has responsibility towards budgeting or towards making money and they just learn a healthy relationship with finances and they realize it's not their money and they have to kind of build something on their own, then that's that's the blessing you can give them and give them opportunities to go try to create a business and try to learn and try to grow. But if you just give them everything like a car at 16 and and they don't have a responsibility for gas or insurance or something, yeah, that that that can get them in trouble pretty quick.

You know, founders and entrepreneurs are always looking to push for more. I mean, there's a great book called Driven and it explains me in a nutshell. How do you know you kind of discuss this, but when's enough enough? I mean, my mom always asked me when's enough enough? I will say like okay so the three pillars in in the book that that I I would an use to answer this question are one purpose like everyone has to maintain or find their purpose and you have to wake up in the morning and know what you're building okay two relationships that's usually your family your really close friends don't want to nothing should your purpose should be very very powerful but it it shouldn't be in sacrifice of those relationships because if if you sacrifice those then the purpose wasn't worth it. And the third thing though was legacy and legacy is like a long word. What does it mean? Um a lot of people can think of like you

know how much money can I give away when I die? There's no definition for it. But for me I'm like if I have the capacity to still be a good father and husband and and and spend time with my family, but I can go build something that allows me to create more wealth. And that wealth I can give away now. I'm not waiting till I die and trying to give away as much as I can right now. And I can see the fruits of investing in in that business and giving away to that charity and helping out those single moms, then like to me that's this fortuitous loop that I love. And so to me, I'm like, let's keep building businesses to create more money so that I can give to my nonprofit and others.

And uh for me that that's that's enough is like well if I can keep that loop running then let's keep expanding that loop. If I'm going to sacrifice family because I'm trying to hit a certain number then then yeah I need to reme-measure and make sure that I'm in a good spot.

You know you remember the guy Robert from Shark Tank? Robert Dakovich or what I

the Yeah. You know, he said, "My biggest problem when I started to make money is I look at my friend's plane or I look at their car or I look at the new house they bought." You know, I've always said pro part of my strengths is why not me when it comes to faith, when it comes to fitness, when it comes to finance. Do you have any tips when it comes to that? I would just, by the way, I'm very competitive as well. Um, you know what I would say though is like that example I shared about me being jealous of my business partner was affecting my happiness level to be jealous cuz he has a bigger XYZ bigger house or a plane or whatever he has. And um I had to sit there and say, "Wow, how stupid is that that I'm like losing happiness because I'm comparing myself to this person."

And I had to learn to be content with like, "Well, what do I want?" and I'd be like, "Well, I want this and I want that and I want those and I want that." I'm like, "Well, I have that." So, I want to keep building those things like family and, you know, like a fun house and be together. And so, to me, you've got to really digest. So, I I call it the happiness audit. Uh is it's the first pillar of of the book. I would actually go through and I would do this. I would write down everything that makes you happy, not your goals, makes you happy.

Write it down. So, I wrote down 186 things when I did this uh on on my own. And then I would say, "How happy does it make you?" 1 to 10. So, some things are a four, some things are a seven, some things are a nine or a 10. Everything from like eating an ice cream cone to like hugging my daughter to watching a football game. Just everything that brings you happiness. Okay. The third column is I would say, "How long does that happiness last?" And I would I would be honest with yourself. How long does that nice meal last? How long does the ice cream last? How long does the feeling of sex last? Does it matter? Put it down. Short, medium, long. Okay. Then the fourth column, I said, um, how much money did it cost me? Okay, so a lot of money, you know, for this trip or a little money or no money. Going for a walk with my wife, no money. Uh, flying to Hawaii, you know, some money. Um, all the stuff. So, I wrote it down. Then I

ran a filter. And what was crazy to me is when I did the filter, the things that brought me the absolute most happiness and lasted the longest, almost all of them were free or costed a $1 sign, meaning it was like anyone could really afford it. And that was like a great way of being like, "Yeah, what what are you talking about? These are the things that really matter." And so to me, it was like the smack in the face of like, "Well, then focus on those things. Those are the things that you really care about."

I mean, when most people do that, they need time. And I think they're kind of stuck at work. Uh for most people, you didn't have to work after you sold.

I did that when I was at DBY. And did you figure out because you said, well, look, I mean, I got the hours here. You know, you you were with the family from 6:00 to 9.

I did that on a plane ride when I was going to a work call, flying from, you know, point A to point B. And I just I had it 30 minutes. It didn't take me forever.

No, no. I'm going to do the exercise for sure cuz I wanted to know by the way if money was going to change is money going to make me happier was like the question and what I realized is like oh money coming or not coming is not going to change the outcome of my happiness then then let's go play with a little bit more risk because it doesn't really matter. All right two more questions and then we'll get you out of here. So, if you could tell most people that are in a founder position, what's a couple examples you would say uh that you've learned through, you know, building a massive company of things that most founders should be thinking about?

Replace yourself. Like, if you're the smartest person in the room all the time, you're only going to get so far. So, you have to be willing to be like, "Okay, how do I replace myself over there and over there?" even where you think you're just the man. At some point, if you want to have scale, you need to have smarter people than you that are like owning it and running. And we uh we typically would hire people that had done whatever we wanted them to do. It's like we needed someone to scale revenue. So, we found someone who'd already gone from from 10 million to 100 million. So we said great, you know, and it didn't have to be the number one at that company, but it had to be someone who was in the car, number two, number three, someone who knew the playbook and yeah, you pay them and you recruit them and you tell them to come over and do that at your company and you'll be probably be in a pretty good spot if you

do it correctly. When you're searching for VC funds, how important is do do you have a lititness test for competitive?

Yeah. No, we had a guy in yesterday um from out of town and you I asked it differently. and basically asking like what's what's the exit plan. What's the goal? What what do you want this to be? And you can get a sense of like what they're trying to achieve and what they consider failure and what they consider success. And it's that same competitiveness coming out. That's always a good indicator of someone who's like, "No, I'm not just you don't fall backwards into building a billion-dollar company. It doesn't just happen. You have to like you have to run through walls to make this stuff happen. So, you know, you're looking for people that have a little bit of fire that have a chip on their shoulder and they're like, "No, I'm I'm going." Like, we're going to go do this thing. And, you know, if you can pair that with a good business model and a and a billboard theory, then hey, let's go.

What's the wrong thing to say that you're just like, I'm out. Like, they could keep talking, but you've already decided in your mind, I'm done.

Yeah. I think when someone says, well, I want to build this and sell it in two to three years. like they're just like their plan is to sell it that quickly. I'm like, look, you might sell it that quickly, but if that's your plan, then you then you're not making the decisions. You're not in it for the long haul. I usually would be like, hey, I I'm not going to invest if your goal is to sell this thing in two to three years. You've got to have a bigger vision than that. And if we have happen to sell it by then, great. But I I that I would usually be out.

Uh if people want to learn more and connect with you or join the Factory for Good community, how do they do that?

Yeah. So, uh, my my my plug for factory is like, um, it's factoryforgood.com. If you have exited or about to exit, we have a bunch of content, a bunch of interviews, a bunch of experiences designed for you. It's all free. It's my nonprofit. We are working with uh founders that have exited and want to learn how to do philanthropy. We kind of build a family office for that side of things and uh, love it. So, come find us at factoryforgood.com. We have a newsletter and if you're looking for investment on the venture side, uh, come check us out at tandem and that'd be awesome.

And then finally, just close us out, Alex. Anything on your mind? Maybe we didn't discuss, but just one last message for the audience.

I really miss building Divvy. It was such a fun time. It was stressful. It was hard. It was long. And looking back, it's easy to be fond because there were not always fond memories in the moment. Um, but for those that are still like in the middle of that hike, just keep going. Like, buckle down. It's not always going to be easy, but if you en if you can learn to enjoy some of that pain, you will miss it. Best of luck. I think growing companies or building a company from scratch is one of the coolest things on the planet. So, um, go get it.

Alex, I really appreciate you. I want to jump on a call with you and discuss some things. I really, really got a lot out of this. And, uh, maybe I'll be out in Utah soon. We go visit you and Todd.

Hey, let's do it. I appreciate you very much for taking the time today, brother.

Thanks so much for listening to this episode. Like always, we're going to close it out with the Tommy truth, which is a little slice of wisdom from me to you that can help guide you in whatever you're striving towards right now. When you start a business, you're really focused on revenue and profit is kind of like what's in the bank right now. And so many business owners, they spend more than they make. If you got a great CPA, but you don't have a CFO or a controller, they'll say, "Spend all your money at the end of the year cuz you're going to owe too much in taxes." But now you got no money in the bank to grow next year. You need to know your known financial position and have enough money to handle the growth. Marketing, capital expenditures, hiring. Once you get serious about profit, all the things start going in the right direction and you create true wealth. And that's it, guys. We'll talk to you next week.

Questions about this episode

Who speaks in "How Alex Bean Created A $2.5B FinTech Company in his 30s"?

Tommy Mello (Host), Alex Bean (Guest).

What is "How Alex Bean Created A $2.5B FinTech Company in his 30s" about?

Alex Bean, co-founder of the spend management platform Divvy, revolutionized financial management for small and midsize businesses by providing tools for proactive spend control, ultimately leading to a $2.5 billion acquisition by Bill.com. His journey highlights the importance of understanding the dynamics of money, both as a power for corruption and a driver for positive change, all while…

What is mentioned in this Tommy Mello episode?

11 people, works and ideas are mentioned, including Alex Bean, Divvy, Bill.com, Tandem, Factory for Good, Atomic Habits. Each one on this page links to its own page with every episode that mentions it.

How long is "How Alex Bean Created A $2.5B FinTech Company in his 30s"?

The episode runs 48 min; the transcript is about 10,051 words in 88 timestamped sections.

More from Tommy Mello

About this transcript: the episode's spoken words as captioned on YouTube, split into timestamped sections. Reclip.Me locates every person, work and idea in the text, keeps the time it is first named, and quotes the words around it verbatim. Last updated February 14, 2026.