From VC to Chief Business Officer: Art Levy on Transitioning to Operating and the Beginners Mindset

As a prolific networker, skilled strategist, and customer-focused leader, Art Levy has the blueprint for building a well-connected career path. I sat down with the Chief Business Officer at Brex, the company offering the financial stack you bank on, to unearth learnings across his career.

In an extended conversation which you can watch in full here, we walk through making cold email intro’s frictionless, why meeting in person is still one of the quickest ways to develop partnerships, and how his father’s work in biotech inspires his work in fintech. Here are some highlights.

Let’s start with your move from VC to working at a startup. What made you decide to move?

There's a book by Annie Duke—Thinking in Bets—where she explains the pitfalls of Resulting - equating the quality of a decision exclusively on its outcome. Before Brex, I spent some time at a startup called Teespring, which lets people create and sell custom t shirts. The company did not succeed but there was an incredible talent density there, including Keith Rabois, Delian, Sam Altman, Justin Wenig, Matt Hayes, and my friend Jack Altman—all were at Teespring. Folks from there have gone to be major CEOs and executives at well funded companies including Open AI, Coursedog, and Lattice.

Coming back to Annie Duke and Resulting, the way I decided on joining Brex was similar to my decision to join Teespring: I wanted to go to a company that had tailwinds, operated in a massive market, and where I’d have mentors looking out for me at the company. Unless you're the Founder, it can be very hard to come in as a new person at a good company and have your voice be heard without a mentor. Those three decision points were true about Teespring and also true about Brex. I remember when I decided on Brex, my mom was like, "You went from hawking t-shirts to hawking credit. What are you doing? You're really going back to your roots."

What was it about Brex’s founders, Henrique and Pedro, that stood out to you? Why did you want to bet your career on those two people?

When you meet Henrique and Pedro for the first time, you’re immediately impressed with their presence and vision. At the time, I was still at the VC firm working for an “experienced” team. Everything there was about experience, experience, experience. But when I met Henrique, he was telling me, "Here's what we're going to do this year, next year, and the year after, and how we're going to build a hundred billion dollar global payments company.” He was calm. He had the vision. Obviously I knew it wasn't going to happen exactly like that, but to see someone talk so clearly about how and why they believe that their company will be successful, it really struck me.

In the first meeting, I asked, “Why do you think this is going to work?" He paused and said, "Look, the U.S. has ~20 banks with a market cap of $10B+. It's a very fragmented market. I believe we found a niche and we're going to run with it, but we're not talking about going up against one behemoth. We're talking about a messy fragmented market."

That's such an informed insight—going after absolutely massive markets that are fragmented. I bet you guys looked at those other companies and knew there was a monster gross profit pool you could steal share from with a 10x better product.

Absolutely. What’s been most interesting to me is to help shape Brex's positioning in the market. In the beginning, it was easy. The first billboards said, "Brex, the card for startups." People were like, "I've never heard of this company, but I'm a startup. Maybe I'll take a look at the website." But once we started serving bigger companies, we needed a software product and then our positioning had to change. Each segment has its own needs.

I really recommend this book called Positioning by Jack Trout, which Henrique told me to read a few years ago, on how to find and market a niche. While I love to read, I do my best learning by meeting in-person with people. I’ve been told I have a really good ability to just sit with a subject matter expert for 45 minutes and intensely understand what they are best at - taking a true beginner's mindset.

I actually think that's the leading indicator for success. The best founders or operators I've met aren’t afraid to bring a beginner's mindset into their conversations. They’re constantly on the hunt for more information. I worry whenever I meet people who don't do that. Why are they not reaching out? What's holding them back?

Yeah. You need to be willing to get your hands dirty. While at Brex, I’ll be visiting the dentist and say, "Hey, what are the tools you use? What’s your buying method? Do you want another credit card?" Jokes aside, I know it’s not as sexy as being the armchair advisor to the CEO but I love it. I'm on construction sites, hawking credit. It’s exhausting, but it’s rewarding.

One of the Gundo founders recently tweeted about making a big career change. He advises folks to just go to a Founder they respect and ask them, “How can I help you? How can I join your team? Throw work at me. Let’s do this." It’s very different from "Hey, let's have a conversation about transitioning and career paths and all that." When I went to Henrique, I said, "Hey, I want to join. Here are my strengths. What can I do?" It wasn’t, "Hey, I'd love to review the JD again. I have these edits in red. Can we get on the same page?" Founders want to know that their employees are fine with their roles changing seven times in the first year.

I think some of the things that make me a good operator made me not as talented a VC. The bias for action and desire to make progress, iterate, and do something every day Ieads me to be highly impatient. I don't think that’s a good character trait for an investor.

In your own words, what is a Chief Business Officer?

At Brex, the Chief Business Officer is in charge of revenue-based partnerships, corporate development, M&A, and fundraising. It's a role and title that allows you to be extremely external. I can go to a conference, speak on panels, meet with our biggest investors, while simultaneously needing to broker partnerships with large companies. I haven't seen a CBO hold a revenue number like a CRO, but I'm sure it could.

How do you really balance being blunt and being effective?

I’d actually say our culture at Brex is to be very direct - there isn’t time to waste. I tend to form deep personal relationships with my cross-functional counterparts, which allows me to be blunt over time. I'm not going to be that direct with someone I don't know well at the company, and I'm not going to be blunt with someone who's not as senior as me, because I don't want them to feel that I'm attacking them, but for someone my level (or above), I'm going to come with a direct punch to the face.

So at the start, you build trust and psychological safety. Maybe that’s also about meeting outside the office and bringing a sense of curiosity—not judgment—to the conversations in the early days. Eventually, you earn the right to be blunt.

Yes exactly. I realized early on that internally, people also want to be brought along for the ride. It’s another type of partnership. If someone asks me, "Why are we doing this partnership instead of building this improvement to the card control?" I will explain the decision again. Leaders don't do that enough. They write a document, maybe they meet with the CEO, and then they just assume the information trickles down to all the people working on the project. In partnerships, you don’t have that luxury.

That's a skill that most VCs don't have: handling bureaucracy thoughtfully and finding the stakeholders they need to win over and get the job done.

It’s a key tenet of Brex. Leaders need to operate on all levels. Over time, I teach my people to explain, "Hey, here's what we're doing. Here's exactly how it should go. Do you have questions? Here's why it's important to Brex," and not just, "Hey, when you see this type of company, do this." Because people want context.

I did a similar thing with an early partnership with JetBlue to transfer miles to our cards. We needed to get the tech resources to learn how to transfer miles. I'm not going to send a message to an engineer or even the engineering manager; I'm going to sit down and say, "Look, here's why JetBlue and Brex is one plus one is three. Your team building this integration will be the key. Will you sign up for this journey with me? We are going to have glory on the other side. Let me take you with me on this ride." They often respond with, "All right, I'm buying what this guy's selling, and now I'm going to support him."

You sometimes reach out to a company for a partnership or opportunity, and if they reject you, you'll go back but through a different department to get the same deal done a few weeks later. How do you know when to keep pushing versus finding another company to talk to?

I think there’s a fine line between being pushy and being persistent. Number one, I never send more than two emails to someone. At first, it’s a, "Hey, should we do this?" After that, I send a reminder, like: "Hey, not sure if you saw this." But that's it. Because let’s face it: if that person ignores two emails from someone who seems like they had a good, thoughtful email, then it’s time to move on.

They're ghosting you.

They're ghosting you. And you just have to keep rowing forward. And honestly, I don't go to another department often, because it can blow up in your face. When I do, I say, "Hey, not sure if you're the right point of contact for this, but I'm trying to build this partnership and here are two sentences on why," and then see what they say.

Sometimes they loop me back to the same person. That obviously kills it. But sometimes they’ll say, "Oh, you actually need to talk to this other person instead." I don’t assume these companies have great communication between all departments. I see it all the time. I believe it’s better to let the right person make the decision.

How does Brex come up with new products and decide what to launch and move into? And how do you validate your hypotheses?

We meet the customer where they are. What are our customers asking for? What are they already using even though it's not a perfect fit? When we launched our software product with enhanced controls and global issuance, it was because there were companies bigger than our “core customer” that were already asking about it, even though our positioning thesis and my branding wasn't “meant” for them.

Even though we were a card for 500-person startups, we had the controls that 10,000-person companies with offices in Mexico and London needed. So when we moved from product to platform, we built with our customers. We kept asking, "What do you need…now?"

Being customer obsessed and constantly in communication trying to figure out what they need in order to make a 10x better product.

Exactly. Like many others, we look at Amazon as a company to emulate. For one, we take anecdotal evidence very seriously. So if a CEO texts me and says, "Hey, I'm having this problem with Brex, what the heck?" or even "I don't like this experience,” I bubble it up to the right team. We don't need to change our Roadmap because of one anecdote, but you have to constantly be gut-checking yourself to meet the customer where they are.

A few years ago, your father passed away, Stuart B. Levy. He’s been called the father of antibiotic stewardship. What are some of the lessons that you learned from him?

He's my biggest inspiration. I have a photo of him in my office that I look at every day. It's from Time Magazine when there was a cover story on him and his work in antibiotic resistance. He was a risk taker, deeply passionate about combating the risk of antibiotic-resistant bacteria. He wanted to make sure people didn't abuse medicine and then built a public company around his advocacy, Paratek Pharmaceuticals.

The first lesson I take from him is be persistent. The second is take risks. The third is bring people along. He was most involved in the science part of Paratek than the business, which led to decisions I think he would have disagreed with. That’s why I build cross-department partnerships so I can build trust and then weigh in on what matters.

How do you bring the community together? And how do you help other people become successful? Is it karmic?

Yes. I will meet with anyone for 15 minutes. I even meet with people who send me a cold LinkedIn message when it’s thoughtfully written and isn't just like, "Hey, let's speak." I will take 15 minutes and say, "Here's my number, call me at this time." It's almost a test. I usually have those 15 minutes on the way back from the airport or commuting to the office or an event. And the serious people actually take me up on it.

If you were to start a company tomorrow, what book would you make people read, and why?

I'll give you something that I've read recently, called Never Eat Alone by Keith Ferrazzi. Keith mentions how networking was always viewed as a negative thing until recently. It’s now “ok” to be authentic and purposeful about who you reach out to. People may say, "But you have an agenda, which means you're disingenuous." But the way I do it, I’m always genuine and out in the open, and people appreciate that.

At the end of the day, I think humans are attracted to genuine people, and in turn want to help them. I think it ends up leading to a lot of shared success, especially as we get older.

Absolutely.

I think one of the best decisions you've made over the course of your career was jumping over to Brex. How did you end up over there?

I decided to befriend all of the VCs in New York City. My thesis was, "Hey, I'm not sure this investing thing's for me, but I want to join a company and these guys have been doing investing longer than me. I think they're going to know good company." I became friends with people like you, Ryan Shmeizer from Thrive, Neil Shah from Greenoaks, and others.

I put the word out that I was looking to join a company in a utility role. It turned out to be from a longtime acquaintance of mine, a guy named Michael Tanenbaum, who you know, that actually flagged Brex and wanted me to meet the founders, Henrique Dubugras and Pedro Franceschi. I flew to San Francisco the next day – again back to showing up. One of the things I take very seriously is getting on a plane and meeting someone at a moment's notice.

It’s so important.

It’s the way I run my meetings: I make myself available based on the other person's schedule. I do that even if I think I'm the more tenured person, because I’m just trying to get the deal done.

So with Brex, Henrique responded on a Friday and wanted to meet in San Francisco Monday. Great. I went out there and pitched them on my network. I've towed the line between investing and operating and wanted to jump into Brex. The first role for me actually came directly from my experience at the VC firm, which was quite ironic. It was hey, get every VC firm to refer Brex to their portfolio—incentivize them and start a channel sales motion.

Did you consider any other options besides Brex?

I looked at a few companies, yes. But never got to the point of crafting the role as I did with Brex.

When you and I first got into venture, the industry was tiny. There were probably 50 of us that worked in venture work in New York. We used to all have dinner with each other and share deals and networks. Today, we go to these events and there's a thousand plus people in the New York tech ecosystem, just in venture at the junior level alone. I believe a shakeout is coming in the next couple of years. Either people are going to leave because they don't want to be investing and go through the hard times, or they'll be forced to leave. What advice would you have for somebody that wants to leave and go operate? Should more of these investors go and operate?

It's a great question, and I totally agree with you. It was amazing to go to your NYC Primary summit this year. I was blown away by the number of people there. Some of the people we grew up with are now some of the biggest GPs in New York. However, for these young investors who've gone into VC because it's a great job with optionality. I think the earlier they know whether they want to do this as their life's work or not, the better. And if it's not their life’s work, I don't think they should stay in VC longer than it takes to find a good company. Don’t think, "oh, I want to get to the principal level and then jump to a company." They should do what I did: meet as many founders as they can, do their day job of finding the best investments, and think, "Hey, would I join any of these companies?"

How do you think about competition? How do you get your staff to tactically, and internally, think about competition?

We always want to understand what other people in market are doing and why they’re doing it. We were first to market with our startup card and startup bank account, but now there's a bunch of very talented teams operating in the space. Our competition has made us better because of this.