Levi King does not talk about leadership like it is a highlight reel. He talks about it like a discipline. One that forces you to confront what you would rather avoid.
Levi is the CEO and chairman of Nav, a financial health platform serving nearly two million small businesses. He has raised capital from firms like Kleiner Perkins and Goldman Sachs. He also sits on multiple boards and writes frequently for Forbes and Entrepreneur. That combination gives him a useful vantage point. He sees patterns across companies, not just inside one.
His core message is direct. If you want people to follow you, you must start by interrogating yourself.
“The human instinct is always to look externally… and say, like, they’re the problem… but that’s human instinct and we got to get over that.”
The Hardest Leadership Work Happens Inside Your Own Head
Levi described something every CEO recognizes and most avoid. Criticism triggers defensiveness. Under pressure, the easiest move is to point outward. The harder move is to examine your own role in the mess.
He framed it as a ruthless inquiry.
“Really be honest with ourselves about how much of the problem I am causing or I am the problem, versus causing the problem.”
That inquiry does more than improve results. It changes how people experience you as a leader.
“It draws people closer to you because they can see that you’re trying your best to be the best version of yourself every day.”
That is the point. The goal is not self-blame. The goal is earned trust.
Scuba Diving Is a CEO Reset Button
Levi is an advanced open water diver. He described diving as the most isolated environment he knows. He also described it as a mental release.
- No distractions.
- No noise.
- No conversation.
“I love the silence of scuba diving. Can’t talk to someone. You, there’s nothing to distract you.”
He then zoomed out even further. A shipwreck reminds you how temporary everything is, including your company, your achievements, and your ego.
“The odds of anyone giving a shit now or in a hundred years are very, very little.”
So what matters? Impact on the people around you. This is a grounding mindset for CEOs who feel trapped inside daily chaos.
The Real Scaling Skill Is Closing the Perception Gap
When I asked what he wished he had mastered earlier, Levi did not talk about fundraising or strategy. He talked about perception.
Two people can look at the same event and walk away with different realities. If you do not close that gap inside your team, execution breaks without you noticing until it is too late.
Levi described the goal clearly.
“Really trying to see how other people perceive us… so that we’re all rolling in the same direction, not think we’re rolling in the same direction, really be rolling in the same direction.”
That is leadership in practice.
- Not intent.
- Not narrative.
- Actual alignment.
Loyalty Can Become a Growth Constraint
Levi sits on five boards. He sees one recurring failure when companies try to scale. People. Not because founders do not care. Many care deeply. That care can become a trap when the business outgrows early team members.
He said it in a way that forces the dilemma into the open.
“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.”
This is not cold logic. It is painful human math. Some people grow with the company. Some do not. Avoiding the truth delays the inevitable and drags the whole organization down. Levi also gave a line I want every CEO to remember.
“You’re going to live or die by the people you have.”
Business Is Personal, Even When People Pretend It Is Not
Levi dislikes the phrase “it’s just business.” He sees it as a permission slip to mistreat people.
He explained why he rejects it.
“Businesses only exist because people show up for work even in the age of AI… we only serve people.”
Then he asked the question CEOs rarely ask out loud.
“How is business anything but personal?”
- You manage risk.
- You set the strategy.
- You allocate capital.
Yet the outcomes still depend on humans choosing to do great work for you.
The 360 Review That Broke His Ego and Built His Leadership
Levi’s self-reflection did not start as philosophy. It was forced on him in his twenties.
He argued with a co-founder about who was the better leader. They ran an anonymous 360 survey with roughly 100 employees. Levi rated himself high. The team rated him brutally low.
He gave an example of the shock.
“I’m a nine and I get it back and a hundred people say you’re a two.”
His first response was denial. He even held onto it for a week.
“They’re all idiots… that’s why I’m in charge of this company and they’re working for me.”
Then he felt something worse than embarrassment. The fear that he peaked at 26.
“It terrified me to think like I’m 26 or 27 and that peaked.”
That fear pushed him into a new operating rule.
“All information benefits me… it’s still in my best interest to have all information.”
Transparency Turned Critics Into Allies
After receiving brutal comments, Levi emailed the entire company. He did not defend himself. He made a commitment.
“I don’t have any answers for you, but I’m going to get to work on this.”
He expected reputational damage. He got the opposite.
“It would actually endear people to me… now are rooting for me.”
CEOs miss this. Ownership does not make you look weak. It makes you credible. People follow leaders who tell the truth about themselves.
Why He Built Nav After Lendio
Levi’s motivation started long before tech. In his early twenties, he built a small business fixing electric signs, then moved into installation and manufacturing. His customers were mostly small businesses. He struggled to understand business credit and financing, then later learned that industries carry different risk profiles.
His takeaway was painful but useful. Small business owners often get denied or pushed into bad financing without understanding why.
That frustration shaped his move from Lendio to Nav.
“If all I could qualify for is subprime… I have a real business… why in the heck is this my best option?”
Lendio helped solve immediate financing. Nav focused on improving the underlying data and conditions over time so owners could escape subprime traps.
“Let’s help you understand the data, improve the data over time so that you’re not stuck in the misery of today.”
Fragmentation Is Not a Problem. It Is the Strategy.
Levi does not view small businesses as a uniform segment. He views them as deeply varied across geography, industry and lifecycle stage.
He used a concrete example. Landscapers in Maine often do snow removal. Landscapers in Florida do not.
“I’ve always viewed small businesses super highly fragmented.”
Nav’s product design followed that insight.
“We had to start with software that wraps around data.”
Start with the truth. Let content and product adapt to the reality of each customer.
AI Makes the Interface Simpler and the Team Faster
Levi described how AI changes a product like Nav. Traditionally, the product tells you what the data means. Now the user can ask anything and get answers without hunting through a maze.
“Now ask us anything and we have the answer, except you don’t have to go hunt for it.”
Internally, AI changed behavior too. When Levi returned as CEO, he discovered employees quietly using AI tools to do far more work. They were paying for the tools themselves. That signaled a cultural problem. AI was being treated like a guilty secret.
He flipped the framing.
“This isn’t a confession… thank you for proactively saying, how can I do 10 times the work?”
Nav created an “AI wins” Slack channel to share productivity gains. He also made the expectation explicit.
“If you’re not figuring out how to be more productive with AI, then you’re going to become antiquated.”
His goal is not layoffs. His goal is scale.
“I’m not looking to let anybody go… instead, we’re just way more productive as a company.”
Early Stage AI Depends on Design Partners
A CEO asked me recently how startups can use AI without enough first-party data. Levi offered a practical approach. Find design partners who will share data and benefit from building the solution with you.
“Usually the best way to do it is to find design partners.”
You reduce dependency on a single dataset by finding multiple partners. That creates a stronger model and reduces the risk of overfitting to one customer’s edge cases.
Final Takeaway
Levi King’s leadership framework starts where most CEOs avoid looking. In the mirror. Self-reflection is not therapy. It is operational. It protects culture, strengthens execution and creates a level of trust you cannot fake.
If you want to scale, stop asking who is wrong. Start asking what you are contributing.
I am Glenn Gow. I coach CEOs who want to scale by becoming sharper leaders, not louder ones. On my podcast, I break down how self-reflection and disciplined people decisions build real trust.
Listen to the full episode of The Scaling CEO with Levi King for a candid conversation on self-inquiry, people decisions, building trust and using AI to multiply your team.
