Lessons from Art Levy

Art Levy, the Chief Strategy Officer at Brex, has shared numerous insights on career development, business strategy, and the fintech landscape. Having transitioned from venture capital to a key operator role at one of fintech's most prominent companies, his perspective is highly valued.

Career and Personal Growth

On the interplay of skill and fortune: "With most people life is like backgammon. half skill and half luck." [1]
On choosing which company to join: "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." [1][2]
The necessity of mentorship: "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." [1][2]
On the transition from investor to operator: "The desire to want to make progress and like iterate and try to like do something every day that pushes things ahead leads me to be highly impatient, which I don't think is a good character trait for an for an investor." [1]
On networking to find opportunities: "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.'" [2]
On being proactive to seize opportunities: When Brex's founder responded on a Friday and wanted to meet on Monday in a different city, Levy's response was "Great." He advises to always "get on the plane." [2][3]
On making yourself available: "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." [2]
On networking with authenticity: "I'm being authentic...I think a lot of times people say oh like you have an agenda and you're disingenuous. and it's like no you're out in the open." [1]
On being open to unsolicited messages: He believes in being open to cold outreach because "'no's are free.” [1]
On the influence of family: "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." [3]
Advice for young VCs: If you realize venture capital isn't your life's work, you should meet as many founders as you can and find a company to join rather than staying just to reach a higher title. [1]
On evaluating decisions: He references the book Thinking in Bets by Annie Duke, which cautions against "Resulting"—the mistake of equating the quality of a decision with its outcome. [2]

Strategy and Business Growth

On Brex's core vision: "Brex, our goal, our vision, is to make every dollar count." [3]
The secret to effective positioning: "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...We're building what they want us to build." [3]
On the importance of focus: Levy admits that one of the hardest lessons for Brex was trying to "do too many things at once." The company regained its trajectory by focusing on fewer products and being more deliberate about customer segmentation. [4]
On scaling with customers: "It is more natural to go upstream in markets where companies grow fast, because...you can scale with your customers, listen to what they need as they grow and ship some of those features." [5]
The challenge of moving downmarket: Levy notes that moving downmarket requires a different approach to marketing and positioning, which companies often underestimate. [5]
On when to introduce a second product: "I think you certainly should not be adding a second product under $10M of revenue because then in my opinion you don't really have product market fit." [5]
The importance of strategic timing: "If we had waited until the current macroeconomic environment turned against tech to start building our spend product...we would be in a bad situation. Here we were lucky enough to invest in leading indicators." [5]
On enterprise sales strategy: "If you're trying to sell an all-in-one solution, sometimes that can slow down the sale rather than accelerate it." [6]
On the "land and expand" model: "With Coupa, we're landing with the P-card, and with Navan, we're landing with the global T&E card. At that point, my client sales team can sell that customer the rest of our suite." [6]
On the importance of positioning by segment: "You have to really think about your positioning by segment and what's that niche that you want to go after." He recommends the book Positioning by Jack Trout. [1]
The power of a clear initial message: In its early days, Brex used billboards that said "Brex the card for startups," which was a very effective and targeted message. [1]
On what defines the best founders: Levy believes the best founders have a unique drive and are incredibly resilient. [1]
The value of an audacious vision: What made him take the leap and join Brex was the founders' "audacious vision and also the talent density of the people there." [3][7]
On the path to IPO: Key milestones for an IPO include achieving market understanding and a positive perception of the company's business model. [7]
On competition: He advises focusing on executing your own plan rather than being overly distracted by competitors. [1]

Mergers & Acquisitions (M&A)

On the key to successful M&A: "On deals that have gone well, the selling founder and I have been super open and honest with each other on what matters and what it would take to get a deal done." [8]
The goal of M&A is synergy: "The focus has been on 1+1=3, why Brex is the right platform for the founder to take his product and company to the next level." [8]
Founder retention is a sign of success: "In our more successful M&As, the founders have all stayed 3+ years at Brex, which is hugely impactful." [8]
For acquired founders, the role matters more than the price: "The longest conversations in the process are never about the price, but rather about what the founder's role will be inside of 'this big company.'" [8]
On attracting entrepreneurial talent post-acquisition: To convince founders to join a larger company, you must cultivate a culture that is entrepreneurial. Levy cites Databricks' co-founder telling people, "If you're entrepreneurial and want to change the world … don't go to one of the giants." [8]
On the current M&A landscape: "I think we're entering an age of massive consolidation where the bigger players are just getting bigger." [7]
Why small "tuck-in" acquisitions often fail: "That doesn't usually work because it's usually not just a product problem... there's a reason why their products...haven't had the adoption of a Brex." [7]
How to attract an acquirer: "You don't want to be showing up in like you know traveling salesman you want to say oh like would love to do a partnership with you because you can bait the acquirers." [9]
When selling your startup, you're selling the vision: "You're selling the dream. You have a product you have the beginnings you have what I like to call green shoots...you need to be like saying look this is going to be a redwood tree." [9]
For founders, the decision to sell is personal: "Really think about your personal situation and don't necessarily listen to investors and advisors who aren't in the trenches every day and who have a hundred bets whereas you're spending all your time building this one." [9]
A deal isn't done until it's signed: "Until you have a signed [deal] you don't have a deal." [9]

Partnerships

The purpose of the Chief Business Officer role: "At Brex, the Chief Business Officer is in charge of revenue-based partnerships, corporate development, M&A, and fundraising... my role is about generating money for the company." [2][3]
Persistence in partnerships pays off: He recounts approaching the travel company Navan for a partnership in 2019 and being turned down, only to successfully forge a key partnership years later. [3]
Partnerships should enhance the partner's product: When partnering with companies like Navan, the goal is "making their product better by incorporating Brex into it." [6]
Building internal buy-in for partnerships is crucial: "I'm not just going to send a slack to an engineer...I'm going to sit down and be like 'Look. here's why JetBlue and Brex. your team building this integration is the key here.'" [1]
Brex's first channel sales motion: Levy's first role was to get VC firms and accelerators to refer Brex to their portfolio companies, a strategy he modeled after Bill.com. [7]
Embedded finance as a customer acquisition tool: "Brex Embedded can serve as a first interaction for an end customer...many of those end customers end up...saying, 'Okay, I've used this Brex card inside of Coupa or Navan. I like the experience; it's a delightful product.'" [6]

Company Culture and Leadership

On the culture of communication at Brex: "I'd actually say our culture at Brex is to be very direct - there isn't time to waste." [2]
How to be direct and effective: "I tend to form deep personal relationships with my cross-functional counterparts, which allows me to be blunt over time." [2]
On earning the right to be blunt: In the early days, building trust and psychological safety is key. Over time, you earn the right to be more direct with colleagues. [1]
The importance of in-person connection: Levy is a strong proponent of in-person meetings as a way to build relationships and get things done. [1][2]
In large companies, don't assume departments communicate well: When trying to partner or sell, it's a mistake to assume that different departments within a large company are in sync. [1]
The importance of every piece of the puzzle: Quoting a character from The Wire, Levy emphasizes a key principle of strategy: "We're Building Something, here...We're Building It From Scratch. All The Pieces Matter." [5]

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