In This Episode
In this episode, host Rory Holland sits down with Levi King, the serial entrepreneur and visionary behind Nav. Levi’s story is a masterclass in building a mission-driven brand, starting with the deeply personal pact he made to secure the Nav.com domain to honor a small business legacy. The conversation moves far beyond typical fintech metrics, diving into the “brutal” 360-degree feedback exercise that transformed Levi from a boss into a leader at age 26.
He also speaks transparently about his personal journey with mental health and panic attacks, advocating for a leadership style rooted in psychological safety and empathy. From his Main Street roots, fixing electric signs to raising $100 million in venture capital, Levi provides hard-won insights on navigating the complex world of business credit and the human side of leadership.
Key Takeaways
- The Domain Pact: Levi acquired nav.com for $90,000 by promising the seller he would honor her late husband’s small business legacy, anchoring the company’s mission in human connection.
- Leader vs. Boss: A painful, anonymous 360-degree review early in his career revealed a massive gap between Levi’s self-perception and his team’s reality, forcing a pivot toward authentic leadership.
- Mental Health Advocacy: Levi shares his experience with panic attacks and therapy to destigmatize the psychological toll of entrepreneurship, viewing well-being as a critical business asset.
- Democratizing Credit: Nav was built to simplify the spaghetti of small business credit, helping owners manage financial health through automated data insights.
- Strategic Capital: Raising $100M+ required the discipline to choose clean terms and partners like Kleiner Perkins and Goldman Sachs over the highest valuation.
- Real-Time Mentorship: While books offer principles, a human mentor provides the contextual wisdom needed during specific, high-pressure professional moments.
- The AI Search Shift: Levi discusses how LLMs are fundamentally disrupting traditional search, requiring fintechs to evolve content strategies for the next generation.
- Culture as Behavior: True company culture is defined by how you treat your customers and your team, not by perks like ping pong tables.
Transcript
The Wake-Up Call That Redefined His Leadership
Levi King: And so I was mad as hell and there was silver lining like it related to strategy, steering the ship. There were things I got scored really high on, I, the things I prided myself on, I was obliterated, right? And, a lot of were friends of mine, like people I recruited that I knew and once I became friends with. And so the first thing I had was like, they’re a bunch of f*****g idiots. Like that’s why I’m in charge because they’re dumb. Like they, of course they need to work for someone like me, which is a natural human instinct that I think applies broadly in business. Even in sales, like salespeople, they want to blame the lead source or something else. Like we never want to look internally. We don’t want to get introspective and say like maybe I’m the problem. And I was not at a period of my life where that was a part of being introspective and really try to see myself objectively.
Introduction: Building Financial Confidence for Small Businesses
Rory Holland: Hi, I’m Rory Holland, CEO of CSTMR and the host of Mighty Finsights. Every year I have the privilege of talking with hundreds of financial leaders and innovators. Today, I’ve invited the founder, CEO, and chairman of Nav, Levi King. On the surface, Nav increases access to credit for small business owners, but in reality, they offer much more, including education and tools to help entrepreneurs build financial health, manage cash flow, and increase their chances of long-term success.
In this conversation, we’re going to tackle how Levi bought a three-letter domain for pennies on the dollar, why a major blind spot almost torpedoed one of his businesses, and the stigma around mental health and entrepreneurship. Mighty Finsights helps you uncover the human side of financial services and fintech, revealing the courageous choices and leaders shaping how we engage with money. Join me as we dive beneath the brands to learn what’s really happening.
Fast Cars, Risk-Taking, and the Mindset of a Founder
Rory Holland: Levi King, so wonderful to have you on the show. How are you doing, my friend?
Levi King: I’m doing well. It’s fun to come on the show, a little bit of full circle for us.
Rory Holland: Oh my goodness, I know. Um, we go back, it’s gotta be, well, close to 15 years now, but definitely want to get into the work that you’re doing at Nav and some of the history of how we got together and the work that we did together with getting Nav off the ground. We’ll talk about the original name of the company when we get going into that.
But first, you have a unique history with driving. You and I share an interest in long-distance driving, I guess I’ll call it that. I call it “windshield time,” and I think it’s a wonderful time to reflect and that sort of thing. But from what I know about you—and I don’t know the whole story, so I’d love you to maybe share a little bit about it—is your driving record. I think I understand that you had your driving privileges revoked in Australia, the EU… and was there somewhere else? I don’t know what happened, I’m fascinated.
Levi King: It’s actually across three continents: Australia, South Africa, Spain, Portugal, and because I didn’t resolve those issues, eventually the entire European Union.
Rory Holland: All right, take me back. You gotta tell… what’s the story behind that?
Levi King: I drive faster than I should. I haven’t nearly as much the last 10 years since I got arrested for speeding in Wyoming, which fortunately wasn’t an arrestable offense, so it just got dismissed. But I had speeding tickets in 22 or 23 states, I think. That was in the 2000s before the states started communicating with each other, so it was like your insurance didn’t find out.
And then my wife and I love to travel and sometimes do cross-country travel. So, drove all over Australia a couple of times, South… I… the second time we took my parents and I had to have my dad drive because I didn’t want to get pulled over and get arrested for anything, having my driving privileges previously revoked. We road-tripped a bit in South Africa and then I went “running with the bulls” in Spain in Pamplona and we drove across Northern Spain and all the way down the coast of Portugal and just… it was mainly just speeding tickets. And I thought, “Ah, what are they going to do?” And, you know, so it’s a bit of a spotty history there.
But the arrest in Wyoming definitely… I sold both of my fast cars, drove a Jeep Rubicon for a couple of years till I realized I had it under control before I bought another fast car.
Rory Holland: What cars—any favorites that you’ve owned?
Levi King: Probably my favorites are the Cadillac CTS-V, Porsche Cayenne Turbo S, Porsche 911 Turbo S Cab. I have a Tesla Plaid now, which is ridiculously fast. My favorite another one is a BMW M Coupe 2001—very unique car, not a lot of them ever came to the US. But yeah, just lots of fast and fun cars.
Rory Holland: I love it. My first car… I was a Smokey and the Bandit fan. I was born in Charlotte, North Carolina, so I got some Southern blood in me. And my folks took me to see Smokey and the Bandit. And so I made a deal with myself when I was old enough to afford my first car—old enough to drive, second, to afford a car—I bought a used, kind of a beat-up, black, gold bird on the front, Smokey and the Bandit car. It was a Detroit car, so it was a little Bondo’d—and if any of our listeners might not know what Bondo is, but the salt on the roads rusts out cars—so, I loved that car. But the same thing, I had a little bit of a problem with a lead foot watching too much Smokey and the Bandit and going fast.
Fortunately for me, with my son’s sport in Motocross, we traveled all the time, but you can’t drive fast with a trailer behind you—you can, you shouldn’t, don’t recommend it. And two, we had a Sprinter van. So, like the Sprinters only go so fast. So in a way, I had my own governor just by the type of car I drove.
Levi King: Nice.
Rory Holland: But I love the Cadillacs. Great to hear that you bought a Detroit-made car. Those are fast.
Levi King: Yeah, that was when they first came out and it was just the idea of a four-door, like 4,000 to 6,000-pound sedan that you could go 0 to 60 in four seconds was just special. And I was like 25, 26 at the time, so I was like the youngest Cadillac driver in the state of Colorado for sure.
Five Businesses, Five Industries, One Relentless Learning Curve
Rory Holland: Oh gosh, that’s so fun. So fun. All right, so before we get into Nav and the great business you guys are doing, I want to just take a minute and tell me a little bit about how you got exposed to business and finance and credit. Because you’ve had a passion for—and I know when you and I talked, I do want to take a minute to maybe talk about how you and I got connected around the concept of business credit—but tell me a little bit about how you taught yourself about business credit and finance.
Levi King: Yeah, it started… I started and sold five small businesses in my 20s that were all very mainstream businesses. The first one was—and I bootstrapped my way into it—but it was electric sign servicing, then added installation, then added full-blown manufacturing. And I had… I was like 22 or 21 when I started that company and so had no personal credit, didn’t understand anything about business credit, financing, and it was just a steep learning curve.
In that type of business, you can largely finance the growth of your business through trade credit, which is a lot easier to get than any type of business loan or business credit card. So over time, it was just being super curious and learning like, “How do third parties make risk-based decisions on this company?” And then once I got that all figured out, you know, it worked great. I started to get access to more traditional financing.
And then I sold that company and I bought a hotel. Turns out manufacturing’s a low-risk industry, a hotel is a high-risk industry, and I didn’t even know the difference. So then I had to learn it all over again. And so each of the five small businesses I started were in different industry verticals, so a different set of rules applies to each of those as it relates to credit and financing.
From Approval to Empowerment: Solving the “What If?” Problem
Levi King: Then I decided I wanted to get into tech. I co-founded Lendio, which is really focused on what type of financing can you get today. They’re partnered with, I think, 70-something lenders, hundreds of loan products, you know, so a single application and you can figure out what are all the different types of financing I’m approved for and kind of compare your options.
What we didn’t solve at Lendio, and Lendio still doesn’t solve—and Lendio, by the way, is a late-stage, profitable, like a meaningful company, probably processes more business loan applications per month in the US than anyone—I was just super passionate about the “Okay, well, what if I don’t get approved? What if I don’t like what I get approved for? What if it’s not enough money? What if I don’t like the terms?” All that long list of “what ifs.” And we at Lendio didn’t solve for that.
So I was kind of inspired by Credit Karma and what they were doing for consumers. I said, “Hey, there’s gotta be a model like this for small businesses.” The consumer mess is a mess to figure out and understand, but it’s way less complex than what small businesses face. There’s not, you know, five or six types of financing; there’s dozens of types of financing. Lenders in each type of financing, in consumer, they underwrite in substantially the same fashion—not true in small business.
And then in small business, your business credit doesn’t just apply to financing, like credit cards and loans; it applies to trade credit, which is four to five times the size of all loans and cards in the US from a credit extension perspective. It impacts the cost of your insurance, your discount rate on your merchant processing, it impacts your ability to get customers. That was another learning curve I had at my manufacturing company. So it just has a far-reaching influence on your business.
So that was the idea behind Nav: bringing the personal credit, the commercial data (which is the three main bureaus: Equifax, Experian, Dun & Bradstreet), bringing FICO’s SBSS score (which is used in SBA underwriting scenarios as well as lots of bank term loans and lines of credit scenarios), and bringing your cash flows. Because it isn’t as simple as consumer; we’ve got to educate them on multiple data sets. It’s all automated—it’s software that’s built around data. And so over the life of your business, if you don’t like your options today, you can make changes in your habits as it relates to your credit and how you run your finances so that you get qualified for cheaper and cheaper credit, but also insurance, you know, all the other things that, like I said, third parties use to make risk-based decisions—not just “Do I want to do business with this company?” but “What are the economics that I’m going to offer?”
The Rebranding Evolution of Creditterra to Nav
Rory Holland: We were… and I don’t recall specifically whether we were in a coffee shop or somewhere, but we had a conversation, I think when you were transitioning into wanting to bring business credit to market is the way that I interpreted the conversation. But that was back… was that 2011, 12?
Levi King: 2012 was when we got to work on the project, me and Caton Hanson, my co-founder.
Rory Holland: Caton, right. Okay. So I remember you mentioning it to me and I thought it was just a brilliant idea as I was coming out of my time at Credit.com and consumer credit was—after ’08 and the markets crashed—we had the subprime credit issues with the home mortgages. So much changed on the personal credit side, but business credit didn’t really get raised to the surface. For a lot of business owners, they were leveraging their personal credit to start businesses, operate, scale businesses. So I was really compelled by what you were looking to do. At that time, the business wasn’t named Nav, though. What was the name that you came out with? I would love to just talk about the story about how you managed to come up with not only come up with the name Nav but secure that domain.
Levi King: Yeah, it’s a… I think it’s a decent story. But we got to the point in development where to pass our next level of certification and compliance with the credit bureaus, we had to have an actual domain name. And at the time, we just had this placeholder domain, https://www.google.com/search?q=UIUX.com, that I paid 10 grand for and still own—wish I hadn’t paid 10 grand for it, but we knew we weren’t going to name the company that.
So it got to the point where Experian was like, “Listen, you got today. Like, you got to figure it out today.” Which is not the way you want to make a decision about what you’re going to name your company—not under duress. But we were bootstrapped because I didn’t want to raise venture capital until we had customers and revenue, so we didn’t get as diluted along the way. So we found Creditterra. We’re like, “Oh, it’s the era of credit! Let’s call it Creditterra.” Like, it was really that stupid.
Bought the domain name for a thousand bucks, moved forward. Well, as it turns out, no small business owner can remember how to spell it, don’t know how to pronounce it. So at one point, we had like a list on a whiteboard of funny ways that our customers said the name—my favorite was always “Credit Tiara.” And so we hated the name. And the last thing we had time for was to figure out how to rebrand.
But Cortera, which at the time was like the fourth or fifth business credit bureau (later acquired by Moody’s), they put the patent office on notice that they were going to sue to invalidate our trademark. And I knew the CEO, Jim Swift, and he was kind of enough to reach out and say, “Hey, I’ve raised 50 million bucks in venture capital, like this is not against you or what you guys are working on, but you know, it’s too close.” So he was super nice about it. I said, “Hey man, we hate this name. Like, period. So this is the forcing function, but I do not want to take one day or even 30 days to make this decision. So can you give us like six months?” He’s like, “No problem.” So he was super cool, always been grateful to him for that.
The $90,000 Domain Deal That Shaped the Brand
Levi King: So we went… we hired a “namer,” a brand… like a guy that just specializes in naming companies. Went two rounds with him, paid him, I think it was 5 or 10 grand a round. He came up with names like “Argyle Crocodile,” “Blue Canoe,” “Credit Fox,” like all this weird shit. But what drove me nuts is he didn’t start with “Is the domain name available?” And like small business owners, we kind of need a .com—like they don’t know all these cutesy domains like .io and things like that. And we wanted a brand that played well in tech, government circles, with small business owners, with nonprofits, you know, so it couldn’t be cutesy, right? Like SBA’s not going to take you seriously if your name’s Argyle Crocodile.
And so we fired him. And eventually, me and my co-founder, we rented an Airbnb loft—back when it was like in someone’s house, you know, it wasn’t commercialized back then—and we kind of locked ourselves up for a few days. We went through thousands of domain names. We compiled the list of our top 10 and then ran it by people we knew that were smart, like the founders of Web.com, one of which owns like thousands of domains. And everybody was like, “Nav.” And I’m like, “Okay, I think we can get it.”
Our budget was 25 grand. We’d raised our A-round from Kleiner Perkins, you know, so we had some money in the bank. And they all said like, “You’re not going to get Nav though. Like, you can’t afford it.” And I was like, “I think maybe.” And so I called the… and we called on some, like https://www.google.com/search?q=Level.com ended up being a tech company, I don’t know what they paid for it. Crux.com we looked at, Rojo.com, like just wanted something simple and concise, easy to spell, easy to remember.
And so I just called the number at the registrar on Nav.com and I said, “Hey, this is Levi King, blah blah blah.” This lady, Roser… I can’t remember her first or last name, but she lived in Florida, a lady in her 60s. And I said, “Hey, I’m interested in buying Nav.com.” And she said, “Well, let me cut you off. I get hit up by domain brokers all the time to sell this. My husband started a small business called Navigator Communications in 1990 or early 90s (I don’t remember the year). And he died a couple of years ago unexpectedly. I had to wind down the business, and I’m waiting to sell the domain to someone who will honor his small business legacy.” I kid you not, those were her exact words.
Rory’s Commentary
Rory Holland: What I love about Levi’s story is how the brand Nav wasn’t just a marketing exercise. It was a pact. When he promised Rose he would honor her husband’s legacy, it anchored the company’s mission in a very real, human way. In financial services, you hear a lot about disruption, but Nav is about navigation—helping the mainstream entrepreneur find a clear path through a credit system that’s designed to keep them in the dark.
Anchoring the Mission in a Promise to Serve Small Business
Levi King: And I said, “Hey, are you like at a computer?” “No.” “Can you go to one?” “Yes.” “Go to Creditterra.com.” Of course, I had to spell it like 17 times until she could find the right website because it was a terrible domain. And then I explained what we were out to do. And we were very early in the journey and I said, “Hey, I promise you no one will honor your husband’s legacy more than us. Like, we’re out to democratize credit and access to credit for small business owners.”
And she said, “Well, what’s your budget?” And I said—and I knew this is like a million-dollar domain, right?—so I said 100,000. Because our budget was 25 and I thought, “Well, if anybody’s mad about it, I’ll just pay the 75 out of my own pocket to get this domain.” One syllable, three digits… navigation is implicit—we don’t say that a lot, but it’s like we’re going to help you navigate the life of being a small business owner. And she goes, “How about 90,000?” And I said, “Done!”
And she was nervous, and I was nervous because it was too good to be true. So we used Escrow.com, which charged 2 grand, so it was a $92,000 expense. And at one point, I started to kind of feel guilty and I talked to her again and I said, “Hey, look, I want you to know like to the right buyer this is a million-dollar domain.” She’s like, “I know that, but we did really well, we saved our money, and I told you my motivation is I want to honor his legacy.” And so then I felt good about it, like retired lady in her 60s, I didn’t want to be taking advantage of her. I even offered to give her an honorable mention on our team—like the team page of our website—she’s like, “I don’t want any attention.” So luckily, I don’t remember her full name, so I can say she’s not getting attention.
So I thought it was too good to be true. So we waited until I’m verifying with our IT guy like, “Okay, we have full access? Like, this can’t be turned around?” He’s like, “No, it’s done.” And then we had an “all-hands” with all like 30 people at the time and kind of unveiled it and it was kind of special for our company because it was like, “Hey, a small business owner made it possible for us 30 years later to build a company around this domain and this brand.” And so it’s kind of a special piece of our company history. It’s also a great lesson on the intersection of luck and hustle. Like we hustled dozens of domains, you know, people would… no matter what email address I used to reach out, they’d figure out we’d raise 6 million bucks from Kleiner Perkins and they’d be like, “Okay, I want $5 million.” Like, I’m not kidding. I’m like, “That’s not how venture capital works. You think I want to get fired tomorrow as the CEO?” And so yeah, that’s the… and of course, it does play well in all those circles.
The funniest thing is—and I didn’t anticipate it—the impression in the market for anyone that we met from a biz dev partnership perspective, they assumed we were some big company. You know, you have 35 people, but… so that was kind of a nice benefit that I didn’t… I never thought ahead and thought like, “Oh, people are going to think we’re a lot more established on solid footing than we actually were at the time.”
The Real Cost of Capital
Rory Holland: Levi, that’s an amazing story and I remember that time because we had started work together at Creditterra, so getting Creditterra off the ground during your seed round and then the A-round came in and then remembering that transition from Creditterra and you’re right, it wasn’t a great name but it was what we had at the time. And just the luck and the hard work and however you want to call it, getting a three-letter domain at that time was pretty remarkable for the price that you got it and the background on that domain and the fact that it was a small business owner that wanted to keep that legacy going—brilliant.
And I remember being able to utilize the budget as a… with the Series A to really scale the business. So thanks for sharing that, that’s a great story. I wanted to talk a little bit about funding. You’ve raised—you know, you’ve been a mainstream business, you’ve raised money for… I’m sure tens of millions of dollars if not hundreds of millions. What are some of the biggest insights or personal reflections you can share from that journey?
Levi King: Yeah, I mean it’s very different when you talk about borrowing money, right? You personally guarantee it, so as a small business owner there’s no such thing as venture capital and angel investors. It’s “friends, family, and fools” or borrow the money or use your own resources. I like the discipline that that gave me before I ever raised venture capital.
But when you raise venture capital, there’s a permanent cost of capital—you gave up permanently part of your business, whereas with a loan, there’s a temporary cost of capital and that’s the interest and fees you pay along the way. So they’re very different. But as it relates to venture capital, Lendio’s raised about 100 million, the majority of which they raised after I left. I’ve raised at Nav 105 million. At Lendio we made some mistakes that you know, we just didn’t know what we’re doing. So understanding preferences and “smart money” and those types of things. We just… and we lucked out because some of those we got, but we didn’t realize we were lucking out at the time.
So at Nav, I was really focused on super, super clean terms, top-notch investors, a board with a very diverse voice. And you know, you get way more “no’s” than “yes’s,” so I always joke I could tell two stories of my fundraising history. One is: I raised $100 million from Kleiner Perkins, Experian, Goldman Sachs, Point72, Crosslink Capital—all these great investors. 1X non-participating, no seniority in the stack, squeaky clean. And it’s a true story.
The other story is: I got rejected like 25 times. I had… I thought the deck I went out with like “I’m raising money on this.” I ended up having to move to the Bay Area—this is all at Nav—and it was very difficult. I got lots of “no’s.” I wanted to raise money from strategic investors; Experian led my B-round, Goldman Sachs led my C-round, and that’s way more difficult to have a strategic lead your round or just invest because they’ve got so many more boxes they have to check. They’re slower. But I wanted that diverse set of voices around the table.
So with Randy Komisar at Kleiner Perkins, he’s kind of a Silicon Valley legend and he was a former operator, two big successes, big failures, and so I knew I could relate to him. I got five term sheets on my A-round and I was going to take his no matter what the terms were. He didn’t know that, luckily, so I got the best terms out of him. But I wanted to work with him. And he became the first mentor I’ve ever had and is still my mentor. So best-in-class, former operator at a best-in-class venture fund. Experian, biggest credit bureau on the earth—it was… I wanted to signal kind of “category winner” early on from a competitive perspective and amazing folks, very different voice. Goldman Sachs, they led off balance sheet so it was a bank investment, not a growth fund investment, and very different voice—a bank. And then added my independent board member that’s still with me today; she led small business at Visa for 20 years then retired and joined my board right after—that’s a network.
And so just very, very diverse set of voices and perspectives around the table and so those are things that were very deliberate. They weren’t easy. And so like I said, there’s tough parts of the story, there’s easy parts of the story, but fundraising’s never easy unless you’re Facebook—but even Facebook, or even Airbnb, they struggled to raise money in the early days because it sounded like a crazy fucking idea. And so eventually they became “hot” and it was easy to raise money, but yeah, just lots of lessons learned but I’m proud of what we’ve been able to pull off at Nav as it relates to who we’ve raised money from. They’re all in it for the long haul, they’re great advisors to the business, and like I said, squeaky clean terms and can’t ask for much more than that.
Mentorship and Learning to Lead at Scale
Rory Holland: What would you say are some of the things that you learned through that experience and when you chose to go with Kleiner Perkins and he became your mentor? What kind of maybe some lessons you learned from him in the early days? Because it’s once really hard to raise money and number two, when you bring in a strategic like that or a partner, you’re no longer… you are still a small business owner as that’s your DNA, but now you have other people to report to. You have other people’s money at the table. Like what are some of the things that he helped you through in those early days?
Levi King: Yeah, there were tons of things. You know, he did encourage us to “go big or go home” and that you can’t get that out of every investor. Kleiner Perkins is a fund that can support like “swing big.” And he pushed me to grow faster than I was comfortable with. And in hindsight, it was the right decision. It could have been the wrong decision, but fortunately we executed well.
So I got that out of him because of his experience but also because he was at a fund that could support that type of strategy. But I went to him… we met probably every other week, at least once a month, sometimes once a week for years. And he was super close to my office, so I’d go over in person and meet with them at his office.
But I… it’s a laundry list. In fact, I learned so many things from him. He’s written multiple bestsellers in kind of the venture-back space and one of them is The 101 Things That Startups Need to Know. And he had me edit—I was one of few people who got the manuscript and edited—and he gave me a shout-out I think in the intro or something. But it was funny because I went through that and I was like… like I knew I’d learned a ton, but I was like, “Holy shit, like I’ve learned a boatload from Randy” you know as I’m going through his 101 top things.
A lot of it’s strategy, like in raising money, structuring your cap table, structuring a board, how to work with strategics. A lot of it’s just leadership, like how do you lead a company? Because you can’t manage a company to scale; you have to lead a company to scale. How to recruit and retain talent—I was always slow to let go of people as fast as I should have. I’m such an optimist and I’m pretty loyal that it was like I could see the good. And so he helped round me out in that regard.
So just a lot of it was just the philosophy in how I was going to build a culture, which isn’t right or wrong for the most part, it’s be deliberate, do something that’s authentic to you. But I would say strategy, you know, all the big stuff, right? Like he didn’t come in and look at code—I don’t know how to code, so you know, he could have criticized my code. He didn’t look at designs, right? He’s a business guy. He was a commercial founder of his companies and that’s what I liked. I was a commercial founder—I didn’t have any particular technical skill set, I just knew how to take an idea, commercialize it, scale it, both as a small business owner and then later in tech.
And so I’d never had a mentor before. And this sounds silly even to myself in hindsight, but I’ve viewed books as my mentor, so I’d read tons of corporate biographies and business biographies. And I learned a ton and you get a lot of good out of that. But what you don’t get is you don’t get anything real-time and contextual for the moment you’re in.
Rory Commentary
Rory Holland: Oh, what a great insight. I like to think about what Levi is saying here as a definition of true wisdom: the perspective that is appropriate for the moment or challenge that you are facing, rather than a broad or abstract principle. Of course, using books as mentors and learning principles is important, but often the most valuable gift that a mentor can give is the words you need right in that moment. Entrepreneurship can be lonely; mentors can make it less so.
Real-Time Mentorship Beats Abstract Advice
Levi King: Beyond meeting with them in person, I mean we’ve had countless phone calls where it’s 30 seconds to five minutes where I’m like, “I’m dealing with this thing. Help me think through it.”
Rory Holland: So valuable. You mentioned strategy. I think very important obviously: what’s the strategy for growth, what’s the strategy for operation efficiency, acquisition, customer acquisition, all those sorts of things. And couple of questions I want to ask you. One, I wanted to talk about that transition from Utah to San Mateo. And you know, because I was part of that journey with you, I remember those days moving multiple children and a family from Utah to the Bay Area is not an easy step. But inside of that, you were not only building a new name and a new brand with Nav, but you were establishing a culture.
So we talked about strategy. I just want to get your thoughts and like, what was the experience like and what type of culture did have you built at Nav and how did that start? What were some of the challenges you faced in trying to establish the culture that you wanted?
Levi King: I think in the early days it’s pretty easy because you pick everyone you hire. You’re all in a small room, smallish office together, there’s plenty of whiteboard sessions, you all eat lunch together. So culture is easy, but it’s also going to happen—like you’re going to get a culture whether or not you’re deliberate about it. But if you go too far without being deliberate about it, it’s really hard to root out a bad culture. In fact, I know lots of companies that they’ve had to turnover half the company when they wanted to change their culture.
And so I knew that, right, because it wasn’t my first rodeo. So we were pretty early in establishing mission, vision, and values. Mission, vision, and values, I think my opinions on culture are: one, they will flow off—they start with your mission, your vision, and the values. And the values have to be true; they can’t just be cool things that you put on the wall to make yourself feel good. They’re not for the outside world, they may put them on your website like we do, but they’re for inside the company.
But ultimately culture, in my opinion, comes down to: how do we treat the customer and how do we treat each other? That’s what your culture really is. And so my philosophy on that is simple: you need to care about the customer, you need to care about the people on your team, it’s got to be authentic and organic to how you show up. So you can’t just say it, then it’s true. And if you have those two things, everything else is easier.
And so we were pretty deliberate about it in early days. When I moved to the Bay Area after our A-round and we started to hire people, we still hired within that value system. We would fly people to Utah once a month because that’s where most of the team was. And eventually started to realize like, “Wait a second, people in Utah somehow feel like people in California look down on them.” Which blew my mind because they didn’t—it was a perception. And so then uncovering like “Where does this perception come from? Why is it there?” Just address it head-on because we didn’t—I didn’t value people in California more than Utah. And we always had the vast majority—now we’re fully distributed, we’re in 30-something states plus Canada—but at the time, it was always like a 10 to 1 ratio at most: 10 people in Utah, one person in the Bay Area.
So there was a little bit there and then some of our values had to evolve a little bit as we grew up in our culture, where this “work fast and break things”—that works when you don’t have customers, or “move fast and break things.” When you have customers and there’s real consequences and you house PII on your servers, you can’t break things. You still want to move fast, but you can’t break things. And so bringing more discipline and order to the company and adjusting the values a little bit so we could become more of a data-driven company. Right when you launch the company there’s no data; it’s all like belief in this thing or this idea. But once you’ve got some traction and history behind you, then you need to be more mature and disciplined in how you make decisions.
So it evolves over time, but I think establishing mission, vision, and values early on is a big piece. And then like I said, I don’t care what you say they are; the way you treat the customer and the way you treat each other, that’s what your culture actually is. It’s not ping-pong tables and free lunch; those are just benefits, they aren’t culture.
Customer Advocacy as a Core Value
Rory Holland: Yeah, I love that. Talking about Nav and the brand and tying this to culture. What would you say or what would your team say about Nav as a brand? And what would your clients say? And does that align in your mind with the culture that you built?
Levi King: Yeah, one of our values speaks to being basically advocates of our customers. And so that guides our decisions on how we monetize, you know, things like: do we make it really easy for someone to cancel their Prime subscription? Or can they just do it online without talking to someone? You know, do we… when we make financing recommendations, do we let how much money we make influence that decision? Which we don’t. And you can cancel online.
But we wanted to build that brand where our customers feel like we are their advocate. They can trust us—I mean, they have to trust us just to sign up; they’re giving us their social security number, their business name, tapping us into their checking account for cash flow advice. And so it was just… we could never compromise on doing what was right by the customer. So, I mean, you can… we have like a 4.9-star review on Android and iOS for our mobile app and so we have great reviews.
There’s customers we’ve failed—we didn’t do well enough. But overall, I think our customer base would say lots of good things and they do say lots of good things about us. And I certainly hope that our team members would say the same. We do an internal survey and our eNPS is pretty high and I think people are very proud that they work at Nav and we do recruit pretty heavily through that that mission and vision. Like, so we have tons of people that work at Nav that are former small business owners, even engineers who are like, “Ah, I’m going to start a dev shop.” And they’re like, “Crap, I’m not just an engineer, I’m in sales and I’m customer service and all this other stuff.” And so they appreciate the journey and how difficult it is to be a small business owner. So that just kind of permeates our culture—is that just a deep respect for small business owners and what they put on the line to chase their dream and how absolutely miserable it is to actually get to a lifestyle business, which is what most of them want. And in Silicon Valley, people kind of look down on them—like, “Really? Like you would look down on someone that built their dream and has a lifestyle they enjoy? Like that’s the point of even being in tech, is to enjoy your life and feel good about what you’re doing—or should be, anyways.”
Rory Holland: Growing up in the Midwest and then having the privilege of living in some different cities including San Francisco and, you know, building a brand like Credit.com and getting exposed to Silicon Valley and that mindset, to be honest, was something I had never experienced. Like I grew up with parents that were small business people—my dad was a small business guy, a contractor. My brother’s the same—not a contractor but has his own small business. And I’m a small business guy and I have been since I started my career. So I really value it and I was… I found it pretty shocking, honestly, like the disconnect between that perspective and almost perception of small business. And that’s why I loved when you introduced me to the concept of Creditterra and then getting the chance to work with you in the early days at Creditterra, then the Series A with Nav and the Series B and I think we worked together almost up through some of the C. It’s just been such a wonderful journey.
From SEO to AI: Reinventing Customer Acquisition in the LLM Era
Rory Holland: I want to ask you a couple more questions and one was… I want to bring it more forward. More than a decade in business, tens of thousands of small business subscribers on the platform, continuing to expand your service offering. What would you say are some of the biggest marketing challenges you’re facing right now?
Levi King: Uh, the first is the shift from traditional search to LLMs. I mean, everybody’s dealing with it, but we historically have done very well on SEO and have done very well on SEM. And you know, historically you searched and then you clicked through to a website to get your answers, and now you just get the answers at the LLM. We are doing really well in search within the LLMs—doesn’t translate to the clicks so far, like it does, not even close on traditional search. I think that’ll evolve—I mean, it feels like a matter of time till ChatGPT and the like that they add advertising and things like that, which we welcome. Like, great! You invested tens of billions of dollars or hundreds of billions, like you deserve to be paid for that.
But that shift is happening faster than the LLMs figure out how to point the traffic external. And so it’s just moving fast, like ridiculously fast. And we can see it in our numbers like almost from the month that ChatGPT launched. And so that’s probably the biggest headwind. It appears so far that the best practices in SEO—like we never did anything “black hat,” we were super careful to always be aboveboard—and it appears that that’s all translating very well to LLMs, which not a huge surprise. So that’s one.
Two is consumer behavior is shifting. Like I’m an old guy now, right? I’m pushing 50. My daughters are all Gen Z. Everything they discover they discover through TikTok. Everything. Like that’s where they find the next shoes they’re going to buy, the bagel shop they want to try on the weekend—it’s always TikTok. And so when you’ve been really good at copy for a long time and okay at video, now all of a sudden you got to be really good at video, but man, it changes big time. Being good at video on YouTube is very different than being good at video on Instagram, which you would think is the same as TikTok, but it’s not.
So just as consumer behavior for discovery shifts, that’s another challenge that it’s hard to keep up with. And so those are two big buckets. And then we’ve long aspired to be like on connected TV, radio, direct mail—some of the other challenges we’ve dabbled but never found unit economics that we could scale. And so we’re kind of revisiting like all the technology around all those platforms continues to evolve from an ad perspective. Like direct mail can be super techy as far as highly customized pieces that are priced as if they… back in the day you had to buy like a million pieces that were the exact same. And so it’s really just customer acquisition—that landscape is changing so rapidly. It used to be what? Google updated their algorithm like once every few years, then once every couple of years, then once a year, and you were always like… even companies like us, you weren’t doing black hat, you were sweating. It was like, “Oh shit, here it comes! Like what’s it going to do to us?” Usually we would get rewarded, but we sure as hell didn’t get rewarded with the emergence of LLMs. Nobody got rewarded. They were dilutive to everybody who was getting traffic the traditional way.
Rory Holland: Yeah, I’ve had… there was a release last summer and then this fall and I’ve had multiple calls the last couple of months with companies that you know, were struggling with the same thing. And we call it “discovery optimization.” But we’ve had the benefit of doing what we do for a living and optimizing brands and SEO and performance marketing. So when ChatGPT and then LLMs and AI search started to become a thing, we already were aware of it so we augmented our strategies.
But now you’ve got this acronym soup, right? AEO, GEO, SEO… and so I spend a lot of my time explaining to folks what that means and then how do you take advantage of it. But I hear you—like that’s a big challenge right now for businesses and trying to acquire customers. And you’re totally right too about the younger generation. And as brands age and mature and continue on to grow and be relevant, we’ve got to adapt our strategies to talk to the younger audience. And you wouldn’t think that a Nav would be… that TikTok would be a relevant place for Nav, but lo and behold, it’s becoming one! And so you got to get good at creating… I can’t wait to see your videos on TikTok, by the way, Levi. I hope the team decides to put you out there because I want to watch it.
The 360-Feedback Session That Shattered His Self-Perception
Rory Holland: So I wanted to talk a little bit about something that you shared with us about your communication skills. Somebody told you once that your communication skills sucked. and I find it hard to imagine given the conversation we’re having right now, so what was that all about?
Levi King: Yeah, I can name him—he’s my brother-in-law, so he can’t, unless he wants to divorce my sister, he can’t go anywhere. But we co-founded my third company together, which was outsourced sales and marketing. We were just co-founders, nobody had the CEO title. We hired sales reps all over the country and I flew out to train a rep he hired in Cleveland. And the guy didn’t show up. I sat there for like four hours, didn’t show up, left a bunch of voicemails—this is before texting—and I left a voicemail said, “You’re fired.” And then I switched my flight and I flew back to Denver.
And my co-founder was so mad. He’s like, “That’s terrible leadership. You don’t know what happened.” I’m like, “Doesn’t matter. Like it’s his first meeting in person with someone that he’s working for—the boss, one of the two bosses—like he needs to show up.” So it spiraled into an argument about who’s a better leader. So it wasn’t actually about communication; it was about leadership.
And so we asked this guy who was later one of the co-founders at Lendio, but at the time we contracted with his company to resell his services: “How do we settle this argument?” He’s like, “I’ll do this 360 feedback thing, anonymous.” So you rate each other on all these categories—communication was maybe the most important one, and it’s like 20 different categories or questions around communication—and then all your employees, like 100 people in our org. We had him and his co-founder do it as if they were our bosses, which we were contracted with them so that was like the closest thing to the 360. And then you rate yourself, right?
I’m going through this thing—I’m like 26, 27 years old—and I’m looking at communication, it’s like, “You know, you’re never perfect, so but I’m a nine. I’m a nine. I’m a nine.” And then 100-and-something people fill this same damn thing out and when you get the results you see: well, here’s what you think and here’s what everybody else thinks.
And it was brutal. It was how many “two’s” I had throughout that thing was embarrassing. In a lot of people have to say “one” for you to get a “two,” right? And so the… there was just such a gap in my perception of myself and what was reality, objectively. And so I was mad as hell—and there were silver linings related to strategy, steering the ship, there were things I got scored really high on, but the things I prided myself on I was obliterated, right? And these are a lot of them were friends of mine—like people I recruited that I knew and ones I became friends with—and so the first thought I had was like, “They’re a bunch of fucking idiots. Like, that’s why I’m in charge—because they’re dumb. Like, of course they need to work for someone like me.”
Which is a natural human instinct that I think applies broadly in business. In sales, salespeople they want to blame lead source or something else; we never want to look internal. We don’t want to get introspective in sales, and I was not at a period in my life where that was a part of me, to be introspective and really try to see myself objectively.
So I stewed over it for like five days just mad as hell. and I just had this moment of clarity and I thought of Married with Children where the main dude, I forget his name, he would always talk about his high school football years and like his “major has-been.” And I was like, I just had this moment of clarity, I’m like, okay, I’m 26 or whatever I was, and if I don’t figure this out, I peaked. And that terrified me. It absolutely terrified me to think like, I’m never going to be better than I am at age 26. So I swallowed hard, I emailed to the whole company the results, and I said, “Listen, I don’t have any answers, but I’m going to commit to you, I’m going to figure this out and I’m going to get better.”
And that transparency was like… authenticity and transparency, that’s when I started to understand the value in that because it actually endeared people to me, to be that transparent and just own it. And then I did, I went to work. I started reading all types of books about personality style and management and leadership and just became a student of the topics and evolved over time and hopefully got better and better to the point where now I believe leadership is as simple as: care about the customer, care about your team, it’s authentic and organic to how you show up. I think it’s that simple. But it was brutal and probably a turning point in my career from a leadership perspective.
Rory’s Commentary
Rory Holland: It takes a lot of guts to email your entire company and say, “I heard you and I’m failing you.” Levi’s transition from that “mainstream grit” to becoming a leader who values psychological safety is a masterclass for any founder. We often think CEOs should have all the answers, but as Levi learned, it’s actually about being humble and the most curious student in the room when it comes to your own blind spots. Entrepreneurship can be lonely; mentors can make it less so.
Levi King: I don’t think I’d be where I am today if I would have just said, “Nope, they’re a bunch of idiots just like I thought, and I’m going to keep being who I am.” It was painful, incredibly painful, but only good came of it.
Fantasy Headhunting and Wayne Huizenga
Rory Holland: Sounds like a gift. Actually, sometimes those gifts come in weird packages, right? I have a not-so-dissimilar story: but I sold my first agency, and we got acquired by a bigger firm that merged us with another agency, and then they put the other agency in charge. And I was full of piss and vinegar back then, and, I wanted to do it the way I wanted to do it.
And I was probably like, same thing, 27 maybe. I told them what I thought of them more than once. Which wasn’t an accurate description of them, actually. It was just a reflection of my brokenness and that I was just being and being a jerk. So until they fired me and I’m like, you can’t fire me. And they’re like, “Well, we just did.” So, getting fired in hindsight was a reflective moment. I could have been… I could have just taken it as well. It’s them. It’s not me, but you know, I really did that self-reflection and did the same thing. I picked up a bunch of books and really reflected. I’m like, boy, I’m kind of a that was kind of being a jerk.
And I was wrong. They weren’t. And no wonder they fired me. And then, you know, it changed the direction of my career, and it made me realize the way that I was behaving was not appropriate. And my reflection of myself was wrong. So in a way, looking back now, gosh, most 30, 30 plus years, it’s been a real blessing. It’s sucked at the time, but it got me to then to the Bay Area to start other companies to do other things. But I did them way different as a result. And it sounds like you did too. It was. It was a it was a turning point for you in a positive way.
Okay, I want to I want to talk about something that we like to ask for guests, and it’s pick one person you’d like to come work at your company. We call it fantasy headhunting. You mentioned Wayne Huizenga. I love that, by the way. Why did you pick Wayne?
Levi King: He’s a lifetime entrepreneur. You can’t help but have entrepreneurs you look at and go “Man, that’s incredible.” Like as crazy as Elon Musk is, I’m like, “the dude’s built fintech, space, automobile, it’s crazy.” And so Wayne took, I think three companies public that are very very different. I think he started with Waste Management, but he took Blockbuster public. He wasn’t in charge when Netflix came around and it went down in flames. AutoNation. He ended up owning sports teams.
Just, like look at someone who can do things in way different categories. It’s one thing if you start a software company. You sell it. It’s a SaaS business. You’re like, “I got another idea for a Saas company,” you know the playbook. It’s substantially similar. So you do another one. Like, that’s impressive as hell, to do more than one. But to do something so different and unlike Elon Musk where tech makes it easier to do all those things. He’s doing it the old-school way, with fax machines and conference calls and traveling all over the place. Dealing with brick and mortar.
Like the complexity of the things he did were just insane. And so, he’s one of those ones. I don’t think there’s a book on him, there should be. It’s just a remarkable story from a business/entrepreneur perspective, what he pulled off in his lifetime.
Rory Holland: Yeah, I know I knew Wayne from his AutoNation days. His that was one of the companies I built was in the automotive finance and lead generation. So. And growing up in Detroit, although he was from Chicago, I think I remember, but he really made him his name for himself in Detroit. So I really respect that. And appreciate that.
Retiring to make Pizza and Beer in Fiji
Rory Holland: Okay. So I wanted to to ask you a couple more questions. And one was that you mentioned that if you could drop everything and do something else, you start a pizza shop and brewery in Fiji. That sounds pretty awesome, by the way. But tell me why that’s so appealing to you.
Levi King: It’s kinda dumb. It was true for a long time. Now it’s like true-ish.
One: I love the south Pacific. I love Fiji. And they have shitty pizza and shitty beer. And so, I thought I could live here, I could retire here, but I’ve got to have two of my favorite things and they can’t be shitty. And what cooler way to retire than to bring the gift of great pizza and great beer to fijians and tourists that visit?
So that’s the, it’s kinda silly, but that’s… I’ve been to Fiji four or five maybe more times. Every time I’m there, I think, “Maybe in a year or two. This is my destiny: open a pizza shop and a brewery right next door to each other. Right on the beach in Fiji.”
Rory Holland: When you do, call me, because I’ll come with you. So I got to ask you, Chicago style Detroit deep dish. Flat. Like, do you have a favorite pizza?
Levi King: Yeah, I’m more thin crust. Hint of sourdough in the crust. Del Popolo in San Francisco is my favorite on the planet, I think they nailed it. But yeah, more of a thin crust guy.
Rory Holland: I grew up thick crust Detroit style and I’m really grateful here in Austin now there’s a pizza franchise called Via 313—313 is the area code for Detroit. So these guys opened up, they do a deep dish but they also they do thin crust—oh my gosh, so delicious. And I have family in Chicago too so I’m nothing against Chicago pizza, but I prefer Detroit.
Mental Health and a New Definition of Strength
Rory Holland: So I wanted to ask you… you and I have had some conversations over the years and most recently a lot of life transitions for you. As we age—I think I got almost a decade on you—but we talked a little bit about the stresses and pressures of running a business, the ups and downs of that and all that sort of thing. But given the season that you’re in right now and what you’ve come from, for people to really know you, what might you want us to know?
Levi King: For years I would tell people my mind is a “steel trap,” and it was true. Nothing could get to me. Quick to anger, but like it just made me smarter—like I could think the most clearly when I was the most angry. And then it broke, man. I started having panic attacks at the end of 2018. It came out of nowhere. I had just binge-watched The Sopranos luckily, because that helped me figure out what was going on.
And I went down a path of mental health to figure out—I hired psychologists, therapists, tried different therapies. Internal Family Systems is the one where I really started to make some progress with a certified therapist in that mode. And I tried different meds, five different meds—they all had a pretty quick negative side effect. I’m not an anti-medication guy.
And I was getting better and better, but I was still having panic attacks. And then I tried psilocybin. I’ve never had a panic attack since. I eventually figured out it’s more of a medicine than a cure for me, so I gotta take a dose every once in a while to keep the anxiety away. But once I figured that out and I’m still a big believer in therapy—I still see my therapist, just not as often—then I haven’t had anxiety since for sure the end of Q1 2021, but I haven’t had a panic attack since May of 2020.
But I could have gotten ahead of that. I didn’t need to break. And now I understand so much more about mental health. If I would have taken care of myself and my mental health along the way, I wouldn’t have gotten to that point. And it was a pretty damn miserable thing to go through. So you know, as someone pushing 50, if I could do one thing different over time, like that’s a mistake I would have preferred to avoid. I mean, maybe not, because I’m really open about it inside the company and out, and so I think that that helps destigmatize it to a certain extent. But man, that was miserable to go through—probably as a collection of misery, probably the most miserable thing I’ve been through in my life, personally or professionally.
Rory Holland: Yeah, I appreciate you being vulnerable and being willing to share that. I think enough men don’t. We tend to isolate when things go sideways to try to go figure it out ourselves and then you bottle that thing up and then it comes out different ways—whether that’s anxiety or depression or you’re just a jerk to be around, or you go to drugs and alcohol, variety of other things to try to mask it and you don’t get to the root. So I’m really glad to hear that you were able to get that right side… get it under control, you got a plan and you’re able to have get some relief from it. But appreciate you sharing that—I think that will help a lot of people.
A Surprising Similiarity and Connecting with Levi
Rory Holland: Man, this has been great, Levi. If anybody wants to connect with you or find out about Nav, where should they go?
Levi King: Nav.com, and by now they should know it’s easy to remember and easy to spell. Or hit me up on LinkedIn. Fun fact: if you Google “Levi King” without Nav, my SEO is dominated by a serial killer who loves the limelight—so 60 Minutes outranks my blog. And so yeah, Google “Levi King Nav” or without Nav if you want a good laugh. But yeah, on LinkedIn, Levi King, or just go to our website and check it out.
Rory Holland: Oh, that’s funny. I gotta say, Rory Holland’s the same—there was a serial killer Rory Holland in Maine. So I’ve had people reach out to me as if I’m him. I’m like, “No, that’s not me, thankfully.”
Levi King: That’s a funny thing to have in common. It comes up professionally after the fact—like after I get to know someone, like usually at a bureau or a bank or something, they’re like, “Hey man, I gotta tell you, when I first Googled your name, I was like, ‘Holy shit!'” Like, “Oh wait, that guy’s still in prison, it can’t be the guy that I’m dealing with. Okay.”
Rory Holland: Yeah, we got more in common than we know, right? So well, thank you, Levi. This has been awesome. So nice to have you on the show and definitely I hope everybody will go check out Nav.com. You guys are doing some great work. So best of luck in the future.
Levi King: Thanks for having me.
Rory Holland: You bet.
Rory’s Closing Remarks
Rory Holland: I want to address an issue affecting a lot of entrepreneurs. As a society, we’ve come a long way regarding mental health and therapy. But far too many people hear a voice in their head saying, “Well, therapy is fine for somebody else, but it’s not for me. I don’t need it.” This attitude can be like a weight dragging you down; eventually, it could drown you. The myth of the high-performing, heroic entrepreneur or CEO isn’t serving anybody. It just pushes good people into burnout, addiction, and dysfunction. Levi King is a beautiful case study in what humility, vulnerability, and practical self-care can look like for leaders, even in a high-pressure startup environment. I hope that his story can inspire the next generation of small business owners to live healthier, happier lives and build companies that make the world a better place.
Levi’s passion for helping small business owners resonates deeply with me. I love that Nav is helping expand the world of business credit so that more entrepreneurs can reach their dreams without working as “credit ghosts” or signing away their equity. As you can tell, Levi and I go way back. It was such an honor to have him on the show and share his journey with you.
Thank you for listening to Mighty Finsights. You’ll find all of our episodes on our website, CSTMR.com, including more one-on-one interviews with fintech and financial leaders and deep-dive episodes on topics like branding and marketing. This show is produced and distributed by CSTMR, a digital fintech marketing agency. All rights reserved. Our production team includes Zac Garver, Becky Dombrowski, Brad Jerger, Romina Gomez, and Belén Ancurio. I’m Rory Holland. Thanks for listening.stening.
