Glenn Gow, The Scaling Executive Coach and host of The Scaling Executive Podcast, sits down with Levi King, CEO and chairman of Nav, to surface the self-reflection practices that King credits with every meaningful leadership breakthrough in his career. King’s core claim is direct: CEOs who instinctively externalize blame in hard moments will plateau, and the ones who turn that instinct inward — asking how much of the problem they are creating — build the kind of team loyalty that compounds over time.
Nav is a financial health platform serving nearly two million small businesses, backed by Kleiner Perkins and Goldman Sachs. King built it from a firsthand experience of being a small business owner who could not understand why his only financing options were subprime despite running a profitable company. Before Nav, King co-founded Lendio and ran five other small businesses across industries from manufacturing to hospitality to retail financial services. He sits on five additional venture-backed boards and writes regularly for Forbes and Entrepreneur. The perspective he brings to this conversation is not theoretical. It is the product of a public, humiliating 360 review at age 26 that he chose to own rather than dismiss.
This episode is for CEOs of scaling companies — particularly those building through the $50M to $250M ARR range on Glenn Gow’s Scaling Executive Podcast — who suspect their own blind spots are slowing growth and want a concrete framework for self-inquiry that strengthens team trust instead of eroding it.
Key Takeaways
- CEOs who externalize blame in hard moments (“they’re the problem”) undercut team alignment. Levi King, CEO of Nav, holds that ruthless self-inquiry — asking how much of the problem you are causing, not just encountering — is the discipline that keeps leadership credible and people close.
- Public disclosure of a brutal 360 review — Levi King emailed full results including comments to his 100-person company — produced loyalty rather than contempt; the team members who gave the lowest ratings began actively rooting for him.
- People failures are the most common reason companies stall between $50M and $250M ARR, according to King, who observes the same mismatch pattern — founders loyal to early hires who have outgrown their roles — across five venture-backed boards.
- Nav team members are completing 2 to 10 times the work per person after a company-wide AI adoption mandate, with no resulting layoffs — productivity gains directed into growth rather than headcount reduction.
- Treating all feedback as useful data — even when it is painful or wrong — is what converts self-reflection from a threat into a competitive advantage. King, who has applied this discipline across five pre-tech businesses and Nav, credits it with every meaningful leadership breakthrough in his career.
How CEOs Learn to Stop Externalizing Blame When Growth Gets Hard
Levi King, CEO of Nav, identifies the instinct to externalize blame as the single most dangerous leadership reflex in a scaling company. “The human instinct is always to look externally in hard times and say, they’re the problem — I’m not the problem. But we’ve got to get over that and really be honest with ourselves about how much of the problem am I causing,” King says.
King’s frame is precise: he distinguishes between being the problem and causing the problem. Both require ownership. A CEO who asks “how much of this problem am I causing?” stays in a position of agency. A CEO who asks “whose fault is this?” loses it. The discipline King advocates is not self-flagellation — it is ruthless, ongoing self-inquiry that keeps leadership honest and keeps the team close.
His evidence comes from a 360 survey he ran at one of his five pre-tech businesses in his mid-to-late twenties. He and his co-founder asked 100 employees to rate them anonymously across five categories of communication. King rated himself a nine. The team rated him a two. His first reaction was textbook externalization: “They’re all idiots. That’s why I’m in charge of this company and they’re working for me.”
He held that position for a week. Then he made a different choice.
“I decided that if I didn’t accept the truth in it and go on a journey to understand myself and other people, that I peaked. And that terrified me — to think I’m 26 or 27 and I peaked.”
King emailed the full 360 results — comments included — to the entire company. He did not have answers. He made one commitment: “I’m going to get better.”
What followed was counterintuitive. “People who just ate me alive in a review all of a sudden were rooting for me. Like they wanted me to win.” The transparency that King expected to damage his authority instead built it. It was the moment he began to understand that authenticity and public accountability are not liabilities for a CEO — they are the fastest path to genuine team alignment.
The reframe King uses to sustain the habit: “All information benefits me. If I don’t like it and it hurts, it’s still in my best interest to have all information.” This converts self-reflection from a threat into a tool.
How CEOs Diagnose People Problems Before They Stall the Company
Glenn Gow asked King directly what he sees derailing CEOs trying to grow from $50M to $250M ARR across the boards he sits on. King’s answer centered on people — specifically, the tension between loyalty and objectivity that every founder-CEO must resolve.
King, who serves on five venture-backed boards in addition to leading Nav, sees the same pattern repeatedly. Founders care deeply about the people who helped them get to scale. That loyalty is a good default. But a company can outgrow a person, and the scope of a role can expand past what someone is able to carry. When that mismatch goes unaddressed, it becomes the actual growth ceiling.
“I think it’s a good trait as a CEO to be loyal by default, but to really try to be objective about who can still row hard enough.”
King rejects the phrase “it’s just business” — not as sentiment but as logic. “Somebody at some point made that up because it was an excuse to be an asshole and then it caught on because it is catchy. But the truth is businesses only exist because people show up for work, even in the age of AI. You may need less people, but you still need people. And we only serve people. So how is business anything but personal?”
His diagnostic framework is simple. If problems are showing up in a company, look at the people in the seats before looking at strategy or market conditions. “You can’t control macroeconomic issues. But you can control who you choose to put on your team and keep on your team. You’re going to live or die by those folks.”
The hard call — moving a loyal early team member out of a role they have outgrown — is not cruelty. In King’s framing, delaying that call is the real failure. A CEO who holds on to the wrong person in the wrong seat out of loyalty is not protecting that person. They are protecting themselves from discomfort. That is externalization in a different form.
How Nav Uses AI to Multiply Team Output Without Cutting Headcount
Levi King returned as CEO of Nav nearly two years before this interview. One of the first signals he noticed: team members scheduling one-on-ones to confess they were using AI to do ten times the work — and paying for the tools themselves. King’s response was not concern. It was recognition that something in the culture was miscalibrated.
“First of all, we should be paying for that. Second of all, this isn’t a confession — thank you that you proactively said, how can I do 10 times the work?”
Nav now runs an “AI Wins” channel in Slack where team members post productivity gains. King describes it as a mandate as much as a channel: “If you’re not figuring out how to be more productive with AI, then you’re going to become antiquated.” He has not used AI efficiency gains as a trigger for layoffs. Instead, Nav has directed productivity gains into growth. “I’m not looking to let anybody go. Instead we’re just way more productive as a company in every part of the business and we have growth opportunities ahead of us. Why would I get rid of smart people?”
This is not a passive position. King frames it as an expectation — people at a technology company should be excited about technology. The productivity gains from AI, 2 to 10 times per person across functions, create capacity for growth rather than justification for reduction.
On the product side, Nav has graduated its machine learning capabilities to AI entirely. The original model was: start with data, let software wrap around it, so every small business gets a customized experience regardless of industry, geography, or stage. AI flips the interface: instead of the product surfacing relevant data to the user, the user now asks anything and gets the answer. “It just simplifies the interface,” King says.
The Principles Levi King Uses to Scale Leadership and Companies
| Principle | What it means in practice | Named evidence from this interview |
| Self-inquiry before external blame | When problems surface, a CEO’s first question must be “how much of this am I causing?” — not “whose fault is this?” | King’s one-week hold on a defensive reaction to a devastating 360 review, followed by his decision to own it publicly, established the self-inquiry discipline he credits with building every company since — including Nav’s growth to nearly two million small business customers under Kleiner Perkins and Goldman Sachs backing. |
| Public ownership converts critics into advocates | Sharing weaknesses transparently with a team — before having answers — produces loyalty faster than projecting competence | After emailing full 360 results including brutal comments to his 100-person company, King found that the same people who gave low ratings began actively rooting for him to improve. |
| Loyalty is a default, objectivity is a discipline | CEO loyalty to early team members is appropriate until the scope of the role exceeds the person’s capacity — at which point holding on becomes a choice to protect yourself, not them | Across five venture-backed boards, King identifies the same outcome: companies that act on people mismatches move through the $50M–$250M ARR range; companies that delay the call stall there, with the unaddressed seat becoming the growth ceiling. |
| AI multiplies people rather than replacing them | When AI adoption is framed as a productivity mandate with no layoff threat attached, teams embrace it rather than fear it | Nav team members went from paying for AI tools out of pocket to posting 2–10x productivity gains in a company Slack channel — after King reframed adoption as expectation, not confession — with headcount held flat and the gains redirected into company-wide growth initiatives. |
| Accept all feedback as data | Painful information is still information. Knowing how others perceive you — even when their perception is wrong — is in your best interest as a leader. | King has applied this reframe across five pre-tech businesses and Nav, each time surfacing perception gaps he would not otherwise have access to. At 26, accepting a professionally humiliating 360 rather than dismissing it set the trajectory for a career that now spans co-founding Lendio, leading Nav to nearly two million customers, and board service at five additional venture-backed companies. |
Quotes from This Episode
- “First of all, we should be paying for that. Second of all, this isn’t a confession — thank you that you proactively said, how can I do 10 times the work?” — Levi King, CEO and Chairman, Nav
- “People who just ate me alive in a review all of a sudden were rooting for me. Like they wanted me to win.” — Levi King, CEO and Chairman, Nav
- “I think it’s a good trait as a CEO to be loyal by default, but to really try to be objective about who can still row hard enough.” — Levi King, CEO and Chairman, Nav
- “All information benefits me. If I don’t like it and it hurts, it’s still in my best interest to have all information.” — Levi King, CEO and Chairman, Nav
- “Businesses only exist because people show up for work, even in the age of AI. You may need less people, but you still need people. And we only serve people. So how is business anything but personal?” — Levi King, CEO and Chairman, Nav
Frequently Asked Questions
How do CEOs build a self-reflection habit that actually improves leadership performance?
Levi King, CEO of Nav, built his self-reflection habit from a forced moment: a 360 review at age 26 in which 100 employees rated him a two out of ten on communication while he had rated himself a nine. Rather than dismiss the results, King reframed how he processed feedback entirely — deciding that all information is useful regardless of whether it is painful. He emailed the full results to his company and committed publicly to improvement with no answers yet in hand. The team responded with loyalty, not contempt. King credits this single episode with establishing the discipline of honest self-inquiry that has carried through every company he has led since.
What people mistakes cause companies to stall between $50M and $250M in revenue?
The most common growth ceiling between $50M and $250M ARR, according to Levi King — CEO of Nav and board member at five venture-backed companies — is a people mismatch: founders who are loyal to early team members and delay acting when a person’s capacity no longer matches the scope the role now requires. The delay is not loyalty; it is avoidance. King’s rule is to be loyal by default but objective about who can still perform at the pace the business now demands. The companies that get stuck are usually the ones where a CEO knows a mismatch exists and waits too long to address it.
How should a CEO introduce AI to a scaling team without triggering fear of job loss?
Levi King reoriented Nav’s AI culture after discovering that team members were paying for AI tools out of pocket and scheduling meetings to confess they were using them. His response was to reframe AI adoption as expectation, not exception. Nav now has a dedicated Slack channel called “AI Wins” where team members post productivity gains. King has not cut headcount as AI productivity has increased — he has directed the gains into growth. His framing: smart people at a technology company are excited about technology, and if they are not figuring out how to use AI to multiply their output, they are falling behind. The result at Nav is 2 to 10 times output per person across functions with no layoffs attached.
CEOs Work with Glenn Gow to Scale Their Companies by Scaling Themselves First
Glenn Gow is The Scaling Executive Coach — he coaches ambitious executives into the CEO seat and CEOs into successful exits. With 25 years as a CEO and 5 years in venture capital, Glenn helps leaders scale their companies by scaling themselves first. If this conversation was useful, you can apply for executive coaching with Glenn Gow or apply to be a guest on The Scaling Executive Podcast.
