In today's episode, Ryan Zauk is joined by Art Levy, Chief Business Officer at Brex.

🎧Brex CBO Art Levy: The Partnerships Playbook, How Brex Went Founder Mode, and Why You Always ‘Get on the Plane’

Podcast Episode · This Week in Fintech’s Podcast · 04/23/2025 · 45m

Apple Podcasts

Brex is the modern finance platform that empowers growing companies to spend smarter and move faster — in 120+ countries. Brex combines global corporate cards, expense management, banking, and travel. Their platform is trusted by over 30,000 companies including ServiceTitan, DoorDash, ScaleAI, and Wiz.

Brex has been at the epicenter of fintech since its founding in 2017 by 2 Brazilian wiz kids, Pedro and Henrique. They were last valued at over $12Bn in 2022, an incredible rise in just a few years.

Art has been at Brex since its "early" days in 2018, joining to help launch their BD function. Over the last 6 years, he has been on an incredible ride building several new functions at Brex, leading M&A, IR, hiring, opening offices, and forging new partnerships like their recent one with Navan.

You can learn more about the Navan/Brex partnership here in our conversation with Navan Expense CEO Michael Sindicich.

In this episode, Art and Ryan discuss:

2:23 - The exact decision making framework he uses (and we all probably should) to assess career opportunities in tech, including the "Five F**k Ups Rule"

4:50 - The 3 things that gave him confidence in Brex after assessing dozens of companies a week as a VC...and the role Michael Tannenbaum + Sam Blond played.

8:28 - His definition of what a CBO does, how he tracks himself, and his 'CBO Role Model'

10:37 - Brex's specific positioning in this massive, ultra-competitive global market and the types of customers Brex serves

14:54 - How his team balances product decision-making tactics across building their own roadmap, responding to competitor products, and listening to customers

16:25 - His Partnership Playbook and why "Rabbits Deer and Elephants" are a common north star. How to think about value maximization vs. long-term partnership. Lessons from negotiating with the NFL while at Teespring

23:56 - What it would take for Brex to buy (or partner with) your startup

30:48 – Brex, Pedro, and Henrique going 'Founder Mode' and why it was the perfect movement for Brex in 2024

35:20 - Filling your team with 'spikes'

36:48 - Why you must always get on the plane

39:18 - An all-time rapid fire round including who he would box in fintech, his skincare routine, why he invested in Bridge.xyz (acquired by Stripe), his favorite apps, Brex team shoutouts, and more.

Enjoy the show.

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Brex is the modern finance platform that empowers growing companies to spend smarter and move faster in 120+ countries. By combining the world’s smartest corporate card and high-yield banking with intuitive software for expenses, bill pay, accounting, and travel, Brex enables founders and finance teams to accelerate operations, gain real-time visibility, and control spend effortlessly. Brex’s AI-powered automation and world-class service eliminate manual expense and accounting tasks for customers, freeing up 11 million hours of employee effort for higher-impact work. Over 30,000 of the world’s best companies, from startups to enterprises, run their finances on Brex — including ServiceTitan, Anthropic, Wiz, Robinhood, Five Guys, and Sonos. Learn more at brex.com.

Art Levy is the Chief Business Officer of Brex leading business development, strategic partnerships, and M&A. Over the past six years, Art has led Brex's key partnerships with companies like Navan, Coupa, Apple, AWS, Zoom, and JetBlue and its M&A deals across the US and EMEA. Arthur started his career at Centerview Partners in tech investment banking and has spent the last 15 years operating and investing. Art is a cum laude graduate of Princeton University.

Ryan Zauk is the Host of the This Month in Fintech Podcast and Bay Area lead for the broader This Week in Fintech platform. In his day job, Ryan is an investor at OMERS Ventures, the direct investing arm of one of the world’s largest pension plans with over $130Bn in net assets. Prior to OMERS, he worked in Morgan Stanley’s Tech Investment Banking team focused on M&A and capital markets. He is based in the Bay Area. You can find him on Linkedin or Twitter.

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Transcript

[00:00:00] Ryan Zauk: [Disclaimer] The views expressed in this podcast are the speaker’s own and are not the views of This Week in FinTech or any other person or entity. The content provided in this podcast is for informational purposes only and should not be construed as legal, business tax, or investment advice or recommendation, solicitation endorsement, or offering by me or anyone else for the sale subscription or purchase of securities, or for investment advisory services of any kind.

[00:00:31] This episode is brought to you by Newline by Fifth Third. Are you ready to grow your FinTech with scalable API enabled payments backed by a leading financial institution. New line empowers enterprise companies to effortlessly launch and scale payment card and deposit products with Fifth Third Bank.

Drive your FinTech forward with the embedded finance platform designed for Enterprise FinTech. Discover how Newline can transform your financial services. Learn more at Newline53.com. Credit products are subject to credit approval and mutually acceptable documentation, deposit and credit products offered by Fifth Third Bank National Association member FDIC.

[00:01:09] Ryan Zauk: Hello everyone and welcome to today's episode of the This Month in FinTech podcast. Listeners, you are in for a great one today as I sit down with Art Levy, chief Business Officer of Brex, one of my all time favorite and probably most entertaining episodes I've done in a long time. Art has been at Brex for six plus years and was just a great guest today.

[00:01:28] In this episode, he and I cover what his career decision making framework is. How that framework plus Michael Tannenbaum convinced him to join Brex. Why a failed partnership with the NFL? Taught him the rabid deer and elephant framework for partnerships, negotiating the big nvo deal and mistakes. He avoided what you need to look like to get noticed and potentially acquired by Brex.

[00:01:49] How he balances roadmap, focus, and competition in such a tough space. The hard changes Pedro made going founder mode to get Brex back on the right track. How his life mantra get on the plane has led to some big wins for Brex and a lot of fun. Ones like big name drops, his best management books, his skincare routine.

[00:02:08] Who'd he'd want to box in FinTech? What drew him to investing in Bridge before they were acquired by Stripe? What a chief business officer even does

[00:02:16] and so much more. Let's jump in. Hello, and welcome to this month's episode of the This Month in FinTech podcast recorded at Brex. It's beautiful San Francisco office.

[00:02:26] So I'm joined today by Art Levy, chief Business Officer at Brex, where he spent the last six years starting as their first BD guy, helping reimagine how businesses manage their finances, and so much more art. Welcome to the show today. Thanks. Really, really excited to be here. All right. So I don't always love jumping into backgrounds.

[00:02:43] People can find this stuff on LinkedIn, but I do like. It's hearing how people think through transitions. So you started at a common career starting point for a lot of people in this industry in investment banking, then ended up jumping to private equity and VMG for a year and then hard pivot out to, uh, Teespring t-shirts or Yeah, sling and t-shirts.

[00:03:04] Pretty wild Free Fish Co. From what I remember from those days. What was your logic at the time, making that jump from professional services finance, the grind into startup world and T-shirts?

[00:03:14] Art Levy: Absolutely. So. My father, my late father was an entrepreneur, so it had always been on my mind to start a company or join and build something.

[00:03:24] But while I was at Princeton, I think I got kind of swept up in the finance.

[00:03:30] Ryan Zauk: Yeah.

[00:03:30] Art Levy: Uh, world and kind of doing what everyone else was doing. Luckily, that led me to San Francisco to take the VMG job. And while I was there, you know, meeting a lot of people, talking a lot of folks, and I realized that it was really a golden age to get into tech.

[00:03:47] And so I was thinking, all right, I need, I want to get into and finally take a leap and join a company. Which company should I join and why would it end up being a schmatta company? Right. And the, the way that I thought about it was I actually had a framework that I came up with. It was essentially three things I was looking for.

[00:04:05] I wanted to make sure there was someone there looking out for me at the company that could help me in my new challenges. New job, new role. So think like mentor. The second was big market. I wanted to go to a company that I thought was attacking a space that we could make. Five Fuckups and still potentially be a good company.

[00:04:24] And three, a company where there was a lot of strong momentum. And so essentially I spent around six months talking to folks and when Jack Altman, who was a friend of mine from Princeton, heard of him. Yeah, heard of him, uh, you know, a nice little name drop in there. He called me and said, Hey, we're re-imagining e-commerce.

[00:04:43] I think there's a role for you on bd. Why don't you take the leap. I thought it was a no brainer and I decided to to jump in.

[00:04:50] Ryan Zauk: So you did that then a stint in VC followed, and as a vc, if you're halfway decent at the job, you're meeting four or five founders a day at least, sometimes a lot more. Eventually, you come across these guys at Brex, two pretty unproven trailblazers from Brazil trying to build in FinTech.

[00:05:08] What was it about those guys and what you saw in Brex at the time that made you want to take the leap of faith and join this company?

[00:05:14] Art Levy: In short, it was really their. Audacious vision and also the talent density of the people there. So, in fact, the way that I met Enrique and Pedro was actually through an acquaintance named Michael Tanenbaum.

[00:05:29] Oh,

[00:05:29] Ryan Zauk: who? Another Brex,

[00:05:30] Art Levy: uh, another Was he at Brex at the time

[00:05:32] Ryan Zauk: already? He

[00:05:32] Art Levy: was at Brex at the time. Okay. Basically. And how did you know

[00:05:35] Ryan Zauk: him?

[00:05:35] Art Levy: I knew him in when we, we both grew up in Boston, we're similar ages. He's a bit older, looks a lot older, but just a little older. And we were not in the same friend group, so we kind of knew of each other.

[00:05:47] Yeah. And we reconnected in San Francisco. Call it in the early 2000 and tens, and he actually called me in 2018, and that was right after he joined Brex and told me, Hey, I joined Brex. It's really interesting. I told him, I'm not so sure about this. You're joining two teenage Right Kids like, let's see how it goes.

[00:06:09] Yeah. And then he called me again six months later and told me, Hey, we just signed this deal with First Republic Rest in Peace to be their preferred corporate card provider. And in my head I remember thinking, huh, this is a $15 billion public financial institution who is picking a 1-year-old startup. To be their preferred corporate car.

[00:06:33] Right. And at the time I had done a stint in partnerships. I know how hard partnerships are to build and cement. That to me, was enough to really, that's a good signal. Yeah. Wanna dig it? So after hearing that, I flew to San Francisco and I met with Enrique and Pedro for an afternoon and I was really just blown away with their.

[00:06:53] Vision for the company and the clarity of thought, like at that time, this is late 2018, they already had a vision of a five-year vision of the company. Now that vision has changed a bit, but actually not that much in the past seven years since then. And just seeing two young guys who just, you knew what they wanted to build.

[00:07:15] To me it was again, just really, really interesting. And I remember at the end of that meeting, one of the things that Pedro said to me is. There's 50 banks in the US worth more than $10 billion. And so it's sort of like we're attacking a space. It's a new company. But back to my earlier point, I again use the same framework.

[00:07:35] Mm-hmm. Which is, I think in career transitions, you really should have a framework on how you think about decisions. Mm-hmm. Um, I really like this poker player named Annie Duke, who has a book, how to Decide Thinking and Bets. Thinking and Bets. Yeah. Yeah. Think that's right. Essentially, again, I had, when I joined Brex or was thinking about it, a mentor in Michael Tananbaum.

[00:07:55] Huge market, right? Global financial services. One of the longest. Yeah. As big as it gets. As big as it gets and momentum, right? This was, I joined right before the Green Oaks round, so that was like, I. Right as Brex was really taking off. Mm-hmm. We had just launched and back to the talent density point, you know, I had the chance to meet Sam Blonde.

[00:08:14] I spoke to other folks who had worked with him. Cosman had just joined from Stripe. The talent density. Yeah. Along with the framework that I had around having someone looking out for me. Momentum in market. Just made a lot of sense.

[00:08:28] Ryan Zauk: These are some heavy hitters that have been coming through the Brex Waltz over the years.

[00:08:32] . So I do want to dig in on your role. So you did six years and maybe we'll cover the rise later, but now you stand as Chief Business Officer. Be honest. It's a little bit of a nebulous role. Seems everybody is kind of a business officer of sorts. Agree. What exactly do you do?

[00:08:47] I, uh, I do business. Business. Yeah. I'm a man doing business. I'm businessing things. Yes. As I used to hear. I was a kid. How is success defined for you, I guess is, is the question I'm trying to get at? What are your. Goals and remit for the year.

[00:08:59] Art Levy: It's a, you know, great question. When I, when I get often, I think, like you said, the CBO role, it's more common in the Valley than other places.

[00:09:06] Right. But, uh, still fairly nebulous and uncommon. At Brex. My remit is partnerships, specifically generating revenue through partnerships, not brand partnerships or mm-hmm. Product integrations, corporate development. Mergers and acquisitions and fundraising. So the way that I would think about it is my role is about generating money for the company.

[00:09:29] Mm-hmm. Um, through these partnerships, through raising money, through acquiring companies. Um, essentially it's an extremely external role, right? So meeting with our largest customers and partners, investors. I am at conferences. I'm talking at conferences. I'm going to meet clients all over the world. In terms of my KPIs, because it's so external and because of the audacity of the partnerships that I'm working on, audacity is not the right word because the long-term nature of them, it's a good spin.

[00:10:01] I am. Judged on a 12 to 18, sometimes 18 months. Okay. Uh, cycle in the sense of, Hey, I have this vision for, for example, one of the things I've done in the past, you know, 12 months is Brex embedded, right? Worked on with the team where it's embedding our card and spend solution inside of other platforms. You know, that was a vision that took time to get momentum and then started compounding with the Navan partnership, Coupa some of the others.

[00:10:26] And so things like that, it sort of. Every quarter I have a view on, Hey, I'm gonna launch this and then we're gonna generate revenue from this, or we're gonna raise money. Like there are tactical goals, but they are viewed on a longer term horizon.

[00:10:41] Ryan Zauk: Got it. So Brex, obviously household name now in the Valley, but there's so many products that have been launched, a very competitive landscape.

[00:10:49] I wanna give the listener a clear idea of what Brex exactly offers today. And what is the positioning when you're out in market? We are Brex. We do X, Y, Z for A, B, C.

[00:11:00] Art Levy: So Brex, our goal, our vision, is to make every dollar count. And so what that means is we serve startups and larger enterprises with a suite of financial products.

[00:11:13] Mm-hmm. Depending on your size and scale, you might use 1, 2, 3, 4, 5 of our products. Those products are corporate card. Mm-hmm. Business bank, account spend, management solution. Bill pay solution and travel management solution. Got it. And so. At the smaller end. As a startup, we want to get you as a customer, right?

[00:11:38] When you incorporate, we wanna get you on the card and the bank account. As you start growing and hiring employees, you go on the spend management. Maybe you use travel and bill pay. Then you get really big, like a scale ai, which has Right. Been with us since they were two people. Really? And then, yeah. Oh wow.

[00:11:57] Yeah. Nice. Um, shout out Alex Wang. Another name drop for you. And now you decide, hey, you know, we're a global company. We need the best global card, which remains Brex, but actually I'm gonna use Nvo for travel. So now I'm using Nvo for Travel, and Brex has an embedded card spend solution for that. And then let's say I'm gonna use Coupa for procurement because again, I'm a.

[00:12:17] 3000 person company, we have a Coupa Pay solution for that. And so I think the global card and spend management is the product that snakes through all segments, right? And then depending on your size and scale, you'll use some of our other products.

[00:12:30] Ryan Zauk: And so let's actually get to that competitive landscape.

[00:12:33] My turn to name drop, I had, uh, Nick Colo from the R Word company.

[00:12:38] Art Levy: What, what company is that? I haven't, haven't heard of them.

[00:12:40] Ryan Zauk: Yeah. And then we had your buddy Michael Sinic from Nvo. Great guy. It's very good. Both on the show, uh, at the end of the fall. It's a huge market as we talked about. And then from outsiders, ruthlessly competitive.

[00:12:53] We see the product launches back and forth, some of the friendlier, unfriendly jabs online, and yet bx. Has still maintained strong positioning. Seems to still be a winner. It's still growing. How does Brex still win in this competitive market? What's been the secret sauce in positioning?

[00:13:10] Art Levy: I think that the secret sauce in our positioning is, I know this is gonna sound cliche, is that we really listen to our customers.

[00:13:18] It's cliche. Cliche. All right, well

[00:13:20] Ryan Zauk: if it, if you mean it,

[00:13:22] Art Levy: let me, it's powerful. Yeah. We're building what they want us to build. Mm-hmm. So. Scale ai, one of our first customers, they're grow as they're growing. They're saying, Hey, we want Bill pay functionality in your product, or we're gonna move to@thetimebill.com.

[00:13:36] Mm-hmm. Hey, we now need better spend management capabilities. I have employees all over the world, or we're gonna move to, you know, other competitors. And so I think that what we've done well is we started with a beachhead in digitally native. Startups, but we've been able to maintain our positioning with that cohort and grow and scale with them so that at this time we have companies like Robinhood, like DoorDash, Coinbase Wiz, a lot of high growers on Brex.

[00:14:05] And so I think the key is staying relevant with our. Initial cohort. I think a lot of companies slip when they launch a second product that doesn't tie nicely with the first one. Right. In a way that it continues to serve their beachhead customer. I'm sure I, I know you went to business school, so you've read Crossing the Chasm.

[00:14:27] It's another chief business officer favorite. Oh yeah. It's

[00:14:30] Ryan Zauk: probably on your desk. It didn't,

[00:14:32] Art Levy: it's on my bedside table.

[00:14:33] Ryan Zauk: Yeah. Under the pillow.

[00:14:34] Art Levy: Under the pillow. Like you need to maintain with. With your beachhead as you, as you use that to cross the chasm to, for us, would be like the larger enterprises, right?

[00:14:43] Like for example, Wiz Robinhood. We didn't acquire those companies when they were small. We acquired them because we've built the functionality that for let's say, scale as it was growing up, that now is relevant for those customers,

[00:14:55] Ryan Zauk: right? But then. How do you stay focused and heads down? What is the balance between, I need to look outward and see what banks, software companies, mercury, whoever else, what they're building, versus this is what we believe, this is what we're hearing from our customers, this is what we should build.

[00:15:12] Art Levy: Yeah. I think it is a, a challenge that we've wrestled with over the years. It's gonna be tough

[00:15:16] Ryan Zauk: and if you're online, if you're on LinkedIn, whatever. On LinkedIn, you have I all day, let's

[00:15:20] Art Levy: just call them helpful investors sending you, yeah. Says so helpful. You, uh, text like, Hey, did you see, uh, this person launched this today?

[00:15:28] Yeah. It's like, oh no, I can't see it. Um, thanks. I think this is where Pedro comes into play. You have to have a really strong and dogmatic CEO that has a vision so that he says, because he's talked to hundreds of customers, talk to a customer every day. Hey, this is what our customers want. I want to continue building down this path.

[00:15:46] So for us, it was digitally native customer. We need to serve it and maintain, make it so that global, digitally native companies continue to use Brex. We need to do that. Now, when you're doing that, does that mean you're serving every domestic company as well as you could, right? Maybe. Maybe not you. There are always sacrifices that you make, but it has to be in the service of your larger.

[00:16:08] Vision. Right? And so the challenge and problem is when you start shifting your vision back and forth, because I think what Brex has done a good job of, of is compounding, right? We're doing, we're doing this, we're serving digitally native global customers. We're moving up market build for that. If you whip saw back and forth because of what competitors are doing, right, that's where you lose, right?

[00:16:28] Ryan Zauk: And so I want to. Dovetail on that a little bit. When you think about products to do next, and like you have this build by partner scenario that you're constantly thinking about. Yes. Especially in FinTech partner, whether that's a great partnership with Nvo and Art actually has sneakers on right now that say Brex and Nvo on the back.

[00:16:47] Or it can be partnering with banks, cross-selling products, infrastructure partners, and the like. How do you approach the build buy partner framework for new products that you're getting

[00:16:56] Art Levy: into? Brex has a really interesting partnership mantra, which is that we actually like to build most of our own infrastructure.

[00:17:04] One of the reasons that large global businesses use us is because we have this global infrastructure that's not really relevant to a 20 person, domestic only company. Yeah, right. But it is relevant to a DoorDash or Coinbase, other one of our competitors. Partner for infrastructure to be able to go to market more quickly.

[00:17:24] We actually like to build our own infrastructure, but then we like to partner on the distribution side. Mm-hmm. And so the partnerships I mentioned with Nvo, we have a great one with Stripe Atlas. Mm-hmm. Around newly incorporated startups, new products.

[00:17:37] Ryan Zauk: Yeah.

[00:17:37] Art Levy: And with a Coupa are all about distribution. How do we get Brex in the hands of as many companies as possible?

[00:17:44] When you think about buy, build, partner, speed to market is really important. But then the counter to that is defensibility. Mm-hmm. And so we did spend a long time building out some of that infrastructure, which did let other competitors move into our space. But now we have a very large moat. Right. And if they want to build that moat.

[00:18:06] That moat has to show up in customer features. Otherwise, no one really cares about it, right? If it's just an economic moat from a margin perspective, especially in heavily funded vc, that's not enough to move the needle. It has to be that you. Own your infrastructure and so you can deliver local cards in right.

[00:18:25] Many more countries, for example, which is one of the reasons we win.

[00:18:27] Ryan Zauk: And I remember, so Michael from Nvo mentioned that a lot that they went on their own journey of, you know, maybe trying to issue cards in many, many geos and then exactly, you know, learned what your capability was there and it was just incredible and just made so much sense to partner.

[00:18:40] And when you're approaching a partnership like that. How do you think about setting up negotiations and it's not necessarily an m and a deal where it's one and done, maybe you're sharking for the best terms. Yeah. And then it's over partnership. You're gonna be, you know, living with each other for a long time.

[00:18:54] But there's also the mantra, same pillow, different dreams for partnerships,

[00:18:58] Art Levy: same pillow, different dreams. I've never heard that. Oh,

[00:19:00] Ryan Zauk: that's

[00:19:00] Art Levy: classic.

[00:19:01] Ryan Zauk: Shout out to

[00:19:01] Art Levy: Michael Grimes. Uh, wow. For that one. Yes. That makes sense. Michael Grimes love him.

[00:19:05] Ryan Zauk: Yeah.

[00:19:05] Art Levy: Wow. Okay. Great, great. So I noticed you said living with like not married.

[00:19:10] Correct,

[00:19:11] Ryan Zauk: because you I'm

[00:19:12] Art Levy: It's a partnership. Yes, it's a partnership. Domestic partnership. Domestic partnership, no matter. I like that. I like that.

[00:19:15] Ryan Zauk: So how do you think about it? Are there tenants you stick to? I know you just mentioned a few there, but maybe using Nvo as an example.

[00:19:21] Art Levy: Yeah, and I'm glad I got to go second after you interview Michael, so I can, you know, debunk anything he said, but.

[00:19:27] I think, excuse me. The Navan partnership was particularly sweet because I actually approached them and he mentioned this about partnering in 2019, where it's like, Hey, you guys will be, our preferred travel will be your card. And at the time we, frankly, they said that they wanted to build out their own, uh, first party card and spend solution.

[00:19:46] And so we had to go our separate ways. And so it was great to reconnect in early 24 when he reached out to build this. Bpay for Navan product for the enterprise. That has had a ton of traction so far. We already have hundreds of customers using it, which is really exciting. That's great. Um, I think when you're doing a partnership like that, that you want to be long term, you actually, you nailed it.

[00:20:11] Can't negotiate too hard in the sense of you need to think about it as a win-win, or at least that both sides think that they want. Right. My favorite negotiating book is, is a book called Never Split the Difference. Mm-hmm. By Chris Voss. It's a big CBO book. Big CBO book. Yeah. That's in the other pillow.

[00:20:28] That's under my wife's pillow actually. 'cause you know, like there's just too many books under the pillows. Essentially, you need to set it up for long-term success. And so when I was negotiating the partnership with Michael, it can't be that we don't. Incentivize his reps right to sell the card at all, because then they're just not gonna sell the card and it's just gonna be an integration that doesn't lead to anything and vice versa, he needs to make our team excited about the travel solution so that we go to market together.

[00:20:55] So I think it's about understanding your partners key desires, not negotiating too hard, and actually sometimes. Pushing for things that help the other side. There were a few times where I actually was going to bat internally for the partnership, and I know Michael was doing the same, where at this point it's, we're so excited about it and we do think one plus one is gonna be five.

[00:21:17] Yeah. That we talk to our CEOs, our CROs about, you know, things like ROE or when and how uh, we, we structure the partnership and we do it in a way that actually. Benefits the other side,

[00:21:30] Ryan Zauk: right? And it's a healthy way to go about it. I rarely see in tech where a bulldozer maximizing negotiation tactic really works.

[00:21:37] In the long run, especially when it's two ecosystem players who are going to keep innovating and growing together, versus Apple just beating the shit out of Foxconn or invent tech or any of suppliers. There needs to be that win-win mentality. So Nvo for now seems like a preliminary win, but winding back to clock, what key mistakes did you make in the past that maybe informed your view coming in?

[00:22:00] Art Levy: I think the key on partnerships is, and this is true about Navan, is you need to have a good culture fit of the two organizations. So when I was green to partnerships and one of the partnerships I did at Teespring, for example, yeah, and by the way, I, I do wanna shout out Teespring, that there was a lot of talent there.

[00:22:18] Jack, I loved Sam Altman was on the board. Keith Rabo was on the board. Deion worked there. Name drop, name drop name, drop name drop, like, you know, it was a classic example. That's of good team, but poor execution. Anyways. Um, shifting back, you need to make sure that the culture fit is there. So at Teespring we did a partnership with the NFL, where we were really excited about selling t-shirts that we're custom.

[00:22:44] With NFL logos and on the surface it sounds like a really good partnership. But the truth is when you're working with a huge global organization Yeah. And there's a power dynamic mismatch that's messed up, it's usually not gonna be set up for success. Right. Mark Sester has a good blog post about partnering and like he calls it like rabbit, deer, elephants, and saying, as a startup, I've never heard this one.

[00:23:06] Oh yeah, it's great. He's saying you wanna partner with deer. Okay, that are big enough to move the needle on your revenue, but they're not gonna move so slowly or require as much customization or be as much trouble as the elephants. And I would take it a step further in that it needs to not only be I. A similar size company, but also a probably a similar sized company that moves at the same speed as you are.

[00:23:30] Mm-hmm. The other big learning for me is you really want to partner with companies that have a similar view of go to market, because especially on the revenue generation side, you need to have a really tight joint go to market for a partnership to work. Mm-hmm. And so if that last, what we call last mile go to market isn't.

[00:23:51] Seamless. Then the whole thing is usually, again, this is for distribution partnerships going to fall apart.

[00:23:57] Ryan Zauk: Okay. That's, that's a new one for my, uh, CBO toolkit. Okay. Great. And then last one on this topic I do wanna talk about m and a. You come from a deal background. How do you think about m and a for Brex and private to private m and a I feel like has been all of the rage is there's.

[00:24:11] Interesting venture-backed companies that haven't found their footing, but have a great team or a great product. Then we've seen big buzzer private to private m and a, like a mosaic getting bought by Databricks. Yeah. What is Brex X's general m and a strategy? What's gonna pique your interest as something to buy?

[00:24:26] Art Levy: Sure. So we've done a little bit of m and a. Yeah. At Brex, we've done a handful of acquihires and then two or three kind of larger acquisitions over the years. I think that for private to private m and a, the acquirer needs to be extremely sure about its strategy.

[00:24:43] Ryan Zauk: Yeah.

[00:24:43] Art Levy: Before making an acquisition.

[00:24:44] Because when you're making a bet on. An acquisition, you're usually for us looking at buying something that is adjacent to what you're building, something you're not gonna build for the next 12 to 18 months, but will then really help your suite of products. And it requires a really robust and granular view of the next 12 to 18 months.

[00:25:07] And I think frankly, for most startups and for most companies under call it 500 million of revenue, they don't usually have. That concrete of a view. Yeah. So unless it's a company like Nvo where they're just buying up travel agencies to Right. It makes sense. Very compliment. Like it's it's very complimentary.

[00:25:26] It's helping their kind of, uh, highest enterprise tier Yeah. That needs white glove service. See it on the slide already. Yeah. Sense. Makes a lot of sense. Yeah. But for. You know, I, we get a, I get a lot of calls as I'm sure you imagine it. It's gotta be insane. Yeah. I get like 15 a week of companies that, yeah.

[00:25:40] And all

[00:25:40] Ryan Zauk: your old VC buddies, you gotta check this one out. Yeah, exactly. This one's different. Hey man, like

[00:25:44] Art Levy: as my friend, please buy my portfolio company. I shameless. Um, I won't, uh, I won't name names, but you've been warned. Yeah. Maybe me soon. Exactly. Exactly. Yeah. I think we, we get a lot of calls and so I have to be very thoughtful and I think the way that we've thought about m and a is the bar just has to be super high.

[00:26:01] Ryan Zauk: Yeah.

[00:26:02] Art Levy: And I think, like I was just reflecting on this with our EVP of product, Erica Dorfman, about when the Navan deal came across our desk, or when Michael met with us, the first meeting, the whole company was immediately like. This is something we need to figure out how to do this. Figure it out. Art, go do the business thing.

[00:26:19] Be a business guy. Yeah. Make it happen. Because it was in we, we felt like it was such a no brainer from a customer perspective. Customers had been asking us about the integration, et cetera. We have a thousand mutual customers at the time. Probably more now m and a. I think it has to be the same way. Yeah.

[00:26:35] Where I can, as A CBO be pushing the deal through. I need product, other evangelists. That being said, I think. My job as CBO is to take, to be kind of the VC arm of Brex. Right. And think about big bets. Emil Michael is, you know, the Uber, he, he made the CBO title rule. Um, he's one of my mentors. Oh, interesting.

[00:26:57] But he. Is really good about pushing me around, like pushing the envelope. What are the biggest things you guys could be doing and at least surfacing that to our leadership team to say, Hey, like here is a direction we could go. Especially at Brex now we're we're growing very rapidly. Again, things are going well.

[00:27:17] That is sometimes the time to take a chance, but I think the thing with m and a is the stakes are. I think a little bit higher. There's a great book called The Outsiders. Have you read that?

[00:27:28] Ryan Zauk: Oh, that's an old one about

[00:27:29] Art Levy: capital Allocators. Yeah, capital, yeah. There's eight

[00:27:31] Ryan Zauk: companies that they spotlight.

[00:27:32] Exactly. Exactly. Oh my God. I'm older than I

[00:27:34] Art Levy: look, you know, the Sun, the LA Sunshine keeps me young, but it talks about that m and a should just be another capital allocation strategy. The thing is that. There just always is more scrutiny on m and a because I think it involves a lot more teams. If it doesn't go well, it has to be unwound and board members know about it.

[00:27:50] It's just a little bit different than if you just start a skunk team of four engineers and you start to build a product that feels less risky. That being said, I do think that companies that are less than 500 million should be extremely judicious and have a really high bar around m and a.

[00:28:05] Ryan Zauk: So how do you source, how do you triage opportunity?

[00:28:08] Like are you still going to events? Are you in TechCrunch every morning? Are you. Having teams build market maps.

[00:28:14] Art Levy: So for MA specifically, I am talking to my product leaders. Mm-hmm. And. Across all of our teams. So whether it's finops or our BillPay team or our travel team or our spend management and understanding what they're building and then thinking through, okay, like what would you want to build but you can't build right now or like what is not on the roadmap, but you would like and our.

[00:28:35] Our CTO, James Reggio and I have a really strong relationship where I'll, at our one-on-ones, just ask him how he's thinking about what he's building and what are some things he wished he could build, but he can't. And then I go out and find those companies. I text all my VC friends saying, Hey, like. What interesting thing, right.

[00:28:52] Do you see, I don't wanna show my hand just yet, but I think some of the partnerships that we'll do this year that we'll announce mm-hmm. This year come from that sort of conversation where there is a gap, we wanna solve it, and I'm just going out and talking to people. The way I like to learn is really through talking to people versus, you know, I think Warren Buffet.

[00:29:14] Joe Warren Buffett says that he likes to read 10 Ks all day long. Right. I like to get out there and, and like call 10 VCs and say like, Hey, what's the best, what's hot? AI powered? But not even what's hot? 'cause that Well, sorry.

[00:29:27] Ryan Zauk: Yes. What? Not What's hot in the VC sense? Yeah. What's like, actually,

[00:29:30] Art Levy: yeah. What, what's hot?

[00:29:32] And in AI powered compliance tooling. Right. And then there's, oh, that's it. Buzzy space Buzz thinks, but it's like, okay. Then I get a list of 10 companies and then I, I email them and say, hello. I'm the CBO of Brex. I think Michael Tananbaum likes to remind me, probably gets, uh, a lot of replies. Yeah. That Michael Tananbaum, who's now, he's, he's moved off from Brex.

[00:29:48] He's the figure seat. He likes to remind me that if I leave Brex, then I'm like nothing again and I have to reveal myself. So, you know. So true.

[00:29:55] Ryan Zauk: Uh, friend. Yeah. Good

[00:29:56] Art Levy: advice.

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[00:30:45] Now I want to talk about ano speaking of KYC for AI buzzy, uh oh wow. Valley topic. I actually wanna jump to a 10 times more Buzzy Valley topic, which is founder mode.

[00:30:55] Okay? Yeah. Think you've heard of it. Early last year, Brex leadership tweeted about going founder mode. I have some stats here. Pedro said earlier this year, we made changes to increase intensity, quality and speed, and that led to revenue growth acceleration, NRR expanding 15 points burned down by 70%, better sales efficiency and the like.

[00:31:16] Can you compare 2023 Brex to 2024 Founder mode, Brex,

[00:31:21] Art Levy: and I think that, uh, burn number is now 90% down, so. Oh wow. Okay. Yeah. Night and day I would say. 23 and 24. I think that what Pedro spearheaded in 2024 was really amazing, this move to founder mode and essentially it was really a return to what I remember the earliest mm-hmm.

[00:31:41] Moments from Brex from my twenty nineteen, twenty twenty, I'll call them the glory days, where. We're too young to start talking about glory days, or maybe you're older than you'll like. Yes, exactly. No comment. Which is really all leaders are getting their hands dirty. Like even as a CBO, I'm still doing 30, 40% IC work.

[00:31:58] Like I'm taking meetings by myself all the time because that's just the mantra of Brex. And so Pedro reset the culture where it was like, Hey, this is what we're doing. If you want to do it, stay. And here's a great reason to, here's a great team. And it worked really well. Honestly, it worked. Better than or faster than I thought it would.

[00:32:17] I've always had huge conviction in Brex. People, you know, over the years have been like, oh, why are you still at Brex? And it's like, 'cause I think we're building a general classic Valley culture. Yeah. Classic valley. We're building a generational company. Yeah. I never doubted it, but we had to make some changes and that was about cutting out middle management, doing, you know.

[00:32:34] Meta did it best. Right? Right. If at that scale they can Insane, insane. What did three, four X stock price at that scale in, in the public markets. Right. Just by going back to Brass Tack, we obviously should be able to do the same, so there's more accountability, less meetings. Cutting out middle management.

[00:32:53] And then I think that the hiring bar went way up because a lot of what I said is a bit cliche, but I think we now know and I now know, and now every leader here knows what type of person can be successful. Mm-hmm. In founder mode, Brex, because it's not every person and it's not the type of person that'll be successful running a 50,000 person award.

[00:33:09] Totally. I Google totally. It's a person that wants to build. We have a lot of ex founders who are here, one of my closest counterparts on the product team, Dinesh. He's amazing and he's started two companies in the past. Like that's the type of talent you want to do with stint, Brex, and hopefully you hold onto them for as long as you can because those are the people that are very cross-functional, communicate well and just want to build and win.

[00:33:33] Ryan Zauk: And then I do want to ask one more follow up on this because there's a lot of founders that we all talk to that want to instill a similar culture into their company and want to do this big shift, big culture change, but it's hard. What did Pedro do to lay out this vision? Anything tactically the leadership team did to make this transition easier?

[00:33:52] Like did he send around the Paul Graham essay with three slides? Did he do in all hands? How did he lay out this pretty scary vision?

[00:33:59] Art Levy: Yeah, I think Pedro's a really great writer, and so we did a few things. So number one, uh, he sent around a Brex 3.0 doctrine. Mm-hmm. That had certain. Frameworks, but number one on there was Brex 3.0 is a place where folks operate on all levels.

[00:34:18] And immediately when we announced that, we also announced some changes to the management team that showcased some of those values. So it was, Hey, Brex 3.0 is a place where you operate on all levels. James Reggio is now our CTO. Matt Bango is now our chief design officer. They've both been here for five, seven years, and we are promoting them because they're the type of person that can not only do a Figma Jam, but also run a large organization.

[00:34:46] Yeah. So he talked about things that then he immediately. Said he was doing. And then it was like, whoa, we're already doing these things. Let's just keep doing it. And then that's, that snowballed a lot because my biggest takeaway at BX for the past seven years is promoting from within and grooming talent is, I think, the best way to get the best result.

[00:35:06] I mean, I know Keith Ra was, it was pretty controversial. I think you said a few weeks ago, under 30, generally attack, just lay out over 30. Uh, again, I won't comment on my age. It was a like. A little funny, but I think he's right in. Right in the The spirit. The spirit of it. Yes, exactly.

[00:35:22] Ryan Zauk: We'll jump to that one quickly on hiring.

[00:35:24] Yes. You have to hire an org. And it's a bit of a weird role sometimes biz dev, 'cause you have consultants, bankers, you have sales folks, you have product folks potentially looking at this role. Do you have any talent hiring philosophies that you've kept over your last six years?

[00:35:38] Art Levy: Yes. And actually kudos to again, Emil Michael for this advice on my team, on my BD team.

[00:35:44] 'cause you know bd, there's Corp Dev on the BD team. I like to hire what I call spikes, which is people that are really, really good in one area of the, what I would call the BD skillset. So what I mean by that is you hire an ex-consultant because he's gonna be good at contracting work and financial modeling.

[00:36:02] Then you hire an ex product founder that wants to learn more of the commercial side, and then maybe you hire or have hired an ex lawyer or someone who went to law school who wants to get into business development because then you can create. A team where you have all the skills that you need and then of course you need to coach and mentor people across the board.

[00:36:22] But that way you can have diverse thoughts in meetings where like, I like to run my meetings where it's brainstorming where, hey, we're at this point with Nvo, like what should we do? Let's talk about it. And my teams are not big, so it can be more of a conversation. And so I think when you have. Three people or four people with different levels of expertise and different skills that are all somewhat relevant to what you're doing.

[00:36:44] It can lead to really interesting outcomes and be a 10 x team.

[00:36:49] Ryan Zauk: And then last question here before we get to the rapid fire round. You're a big travel guy yourself. I saw 85 flights last year. Flighty. Great app by the flight. Yeah. Shameless plug for flighty. I, I've, I've got a lot of friends trying to get me on the app.

[00:37:03] Maybe this will be the, the final straw took 85 flights last year. That's a flight every four days. Including holiday, weekends and all 52 weeks. So probably more in terms of your working. Yeah. Weeks. Yeah. Where are you going? And we have Zoom. You have offices. Why are people not coming to you at this point or just doing Zooms?

[00:37:21] Art Levy: Yeah, it's a great question. I think that I. My mantra in life is really the idea of get on a plane. I think that time kills all deals, and I think that to be successful, you should just have the meeting, go see the person, and frankly, I'm a big proponent of in-person meetings. As obvious from my flight, right?

[00:37:42] I can't tell you the number of times this year where I took an 11 hour flight to have a breakfast with someone. That was very important, and then structure a whole other business day or two around it. But where during that meeting suddenly I. Found out something about the partnership that hadn't been clear from the last three months of Zooms or something transitioned, a partnership transitioned to me, or there was a tough moment where it always makes more sense to be in person.

[00:38:10] There is a partnership that I reignited after three years of being quite dormant because I just sent them an email saying, Hey, looks like we should really. Talk again. Here's all the progress. When are you free next week? And they're like, oh, well I live in Palm Beach, Florida, or I'm in Palm Beach, Florida on vacation.

[00:38:26] I said, great, how's I see you? There's Who's day breakfast? And then from there, three months later there's real traction, right? So I can't, I can't vocalize enough how much I think meeting in person is important. And then why don't they just come to me? That's a great question. I think the idea is I'm always solving for speed.

[00:38:43] So yes, if we're both in San Francisco, let's meet. There's no reason to fly. But I think that. If it's gonna delay things for two weeks, one week even, it's always better. I think. Frank Sluman, who's another writer, legend. Legend, I mean obviously Legendary, CEO, but he's written a lot of Amp it up, right? Amp up Up, exactly.

[00:38:59] Yeah. Is if someone tells you that it can be done in a week, say, why can't it be done tomorrow because it's done tomorrow, then he's gonna pass it to you tomorrow, and then you're gonna have comments and it's just gonna keep moving. And I think that deals are very much the same way and. Being in person just speeds things up even more, like for all these deals, when you sit in a room like we all used to do mm-hmm.

[00:39:19] Negotiations happen faster.

[00:39:21] Ryan Zauk: Yeah. All right. Now with that are, you've made it to the final part of the interview, which is the rapid fire question round. Okay. We got some good ones here. Okay. Are you ready? Yes. So each one, like five to 30 seconds depending on how you feel, uh, answer. Alright. First one, we're, we'll go deep here.

[00:39:37] You run into your 22-year-old self and you've got about 10 seconds to speak. What do you say? And this can be like life advice, a mantra, career decision,

[00:39:46] Art Levy: I would say, or lean into what you're good at. Do not listen to what everyone else is doing and spend more time with your parents because you don't know how long they'll.

[00:39:58] I hear you are an immature boxer of sorts.

[00:40:01] Ryan Zauk: Is this true?

[00:40:02] Art Levy: I mean, I, I do, I spar once or twice a week. That's correct. Oh,

[00:40:05] Ryan Zauk: once, twice a week. Okay. Yes. And this isn't like rumble. No, no. It's

[00:40:09] Art Levy: not fancy. Like you bake fancy. No, no. This is like real

[00:40:12] Ryan Zauk: head gear. Gnarly gen. Gnarly, yeah. Yeah. Champion or whatever the, the brand is.

[00:40:16] Okay. You get to fight two people. One in tech slash FinTech, one in general life. Who do you pick?

[00:40:25] Art Levy: Michael at Nvo.

[00:40:27] Ryan Zauk: Oh, total. Yeah. Oh, alright. Right. Yeah. Was it just some anchor from the partnership negotiations? You know, I think it'd just be fun. He's like also like a big,

[00:40:34] Art Levy: I

[00:40:34] Ryan Zauk: was gonna say he's a pretty

[00:40:35] Art Levy: thick guy for remember himself.

[00:40:36] Like it would definitely test my fair, fair point. My acu. Yeah. And we're talking like gloves, everything fair? Yeah. You know, referee, I imagine like a crowd there. Um, so it's, it's uh, very kosher.

[00:40:47] Ryan Zauk: Wow. Okay. This could be a great FinTech fundraiser down the road. And then what about non FinTech General life?

[00:40:53] Probably, uh, mark Zuckerberg.

[00:40:55] Art Levy: Oh, yeah, that is a great

[00:40:57] Ryan Zauk: answer. Yeah, he's, he's a big juujitsu guy now. Big jujitsu guy. Allegedly.

[00:41:00] Art Levy: Allegedly. And I don't think he's, like, toned his boxing yet, so, okay. Maybe I could stand a chance. Uh, that's a

[00:41:05] Ryan Zauk: great answer. I'll, I'll have to send this to him now. A little more serious.

[00:41:09] Or, you're an angel investor. You've had some good wins. Most notably Zach at Bridge, which

[00:41:14] sold to Stripe for a billion plus. What was the 10 22nd thesis on writing this check?

[00:41:20] Art Levy: Zach was. Amazing, uh, chief Product Officer at Brex. The biggest takeaway for me about him was laser focus. The thing I remember the most was I would come to him with a bunch of crazy partnership ideas and he would just say, no, I'm not building any of them.

[00:41:34] And at the time, I was mad about it. Right, right. But I realized he just. Super focused on his vision. And so when I heard his vision about stable coins, I don't know, stable coins, like I'm just being dead serious. So like I love the honesty 'cause most people feign some things. No, no. But now I have stablecoin expert on my LinkedIn.

[00:41:52] Oh there we go. Of course. Um, right. But he was like, this guy's going to build and he's going to make it successful. Like of course if the market flops, it's not gonna work out, but Right. I believed in him.

[00:42:03] Ryan Zauk: What are two traits that make you stand out as Brex CBO, and why you think that you got here?

[00:42:08] Art Levy: I think that related to some of the things we've talked about, I'm pretty spontaneous, so I'm willing to drop everything and go hard after a problem.

[00:42:17] I. A partnership, whatever it is. There've been times where I've got, again, back to the plane theme, I've gone on a plane two hours after a call because it just needed to be done. That's great. I think I have pretty good eq. Um, and honestly it's not, it hasn't always been this way as you know, people from probably my high school or college days to tell you.

[00:42:36] Hopefully you're not in touch with any of them. But I think, I think you can be learned and I think when you meet someone and you really think about, hey, like. What do they want? That's the thing. People a lot of times are just yapping away about, here's everything I want. Here's why you should, I should, you should buy this from me, right?

[00:42:51] It's like, no, think about what this person wants. How can I help you? I think really being empathetic in that way is very important, so I think that has helped me get to be moderately successful. And I think the last one, even though you asked for two so we can slice it, is I have a lot of energy. I think part of the reason I love boxing, part of the reason I I pumps through in the interview,

[00:43:11] Ryan Zauk: there's a lot of energy.

[00:43:12] Yeah, good.

[00:43:12] Art Levy: I'm very energetic. I like, you know, my wife yells at me 'cause I like jump out of bed every morning. Yeah. And jumping in on planes. She's gotta drive her nuts. You never around. Yeah, exactly. No, I, she just doesn't mock me around. It's actually a good thing.

[00:43:23] Ryan Zauk: Yeah. Yeah.

[00:43:24] Art Levy: We've been married six months, so you know.

[00:43:25] Ryan Zauk: Oh, okay. Oh, congratulations. Thank you. Alright, next one. This is one of my favorite parts of the episode, teammate at Brex that you'd love to shout out for a job well done the last few months,

[00:43:35] Art Levy: Ashish. So Ashish is our VP of VD and he's just an absolute force. He came from Microsoft, Facebook and then been at Brex for over three years.

[00:43:46] Just incredible.

[00:43:47] Ryan Zauk: Alright, last question. This one has also come up a couple times on age. I think you're like four or five years older than me, but you might look at least two years younger than me. What is the personal health stack? Skincare routine supplement stack that you have to share with our listeners.

[00:44:02] Art Levy: Yeah, I get this question a lot. Um, so humble. Yes. So, um, look, here's the stack. So number one, eight, sleep with a consistent bed. Bedtime of, okay, what is it? 10:00 PM Okay, 10:00 PM up at five 30.

[00:44:17] Ryan Zauk: How much do you break, or how often do you break that time rule? Um, up at five 30. So you're getting hours back in the day?

[00:44:23] Art Levy: Yeah. Okay. But still, so I try to really be regimented about it when I'm not traveling. I

[00:44:28] Ryan Zauk: was about say, 'cause the travel time zones, do you stick to that rule? You getting six hours? Yes,

[00:44:32] Art Levy: I'm getting like seven, try to get seven hours a night. Okay. Um, time shifter, another great app that I use a lot. Okay. I don't know, um, oh, it's for jet lag and for like keeping you on a time zone.

[00:44:41] It's really helpful. Okay. Supplements. I, I like a little magnesium, L-theanine. Oh. Uh, from a skincare routine, you know, I use some, a brand called Tata. Tata, Tata Skincare.

[00:44:54] Ryan Zauk: Okay. Is it, it's like a

[00:44:56] Art Levy: women's brand.

[00:44:57] Ryan Zauk: I was about to say, I've heard of most of the men's, like,

[00:44:59] Art Levy: yeah, no, I think, I think the, you know, as my wife tell me, the women have been gatekeeping the skin.

[00:45:04] Yeah. Skincare, rash regime. Yeah.

[00:45:05] Ryan Zauk: All right. Tata, you heard it here first. If you want to age gracefully, that's what we've got. I The Brex customer.

[00:45:09] Art Levy: Sorry, I had to, I had to.

[00:45:10] Ryan Zauk: Oh, is it? Oh, okay. All right. Good plug. Well, art, thank you so much for coming on today's episode of the This Month in FinTech podcast.

[00:45:17] This was a ton of fun, one of our most fun conversations in a while. Thank you for coming on.

[00:45:21] Art Levy: Yeah, this was great. Thanks,

[00:45:22] Ryan Zauk: man. Thank you for listening to today's episode of the This Month in FinTech podcast. If you enjoyed today's episode, please like, follow, subscribe, or rate us across your preferred podcast and social media platforms.

[00:45:37] Lastly, I'd like to thank our editor Evangelo Marco for his great work on our episodes. Signing off. I'm your host, Ryan Zauk.