Introduction
Sean Kim was collecting aluminium cans for pennies before he had a business card. By the time he was cooking Korean food at home and selling it to colleagues at his first office job just to cover New York rent, the pattern was already set: find the uncomfortable thing, do it anyway, learn what it teaches you.
That pattern took him through Experian, DirecTV, Amazon, TikTok, and now Kajabi, the platform that helps creators turn content into a business. On this episode of Everyday Leadership, Sean sits down with Sope Agbelusi to trace how a habit of choosing discomfort, not avoiding it, became the throughline of a career spent inside some of the biggest product and leadership decisions in tech. Along the way: the Amazon email that changed how he leads forever, why he tells his team failure is the job, and what actually happens to founder mentality once the company outgrows the founder.
From collecting cans to coding a startup
Sean's entrepreneurial instinct didn't start with funding rounds. It started small: selling things at school, collecting cans for spare change, buying toe socks in bulk in Korea and reselling them to classmates for a few dollars a pair. When he moved to New York and found the cost of living punishing, he started making Korean food at home and selling it to his own office.
"I have no shame, it's like, hey, you gotta do what you gotta do," he says. Looking back, he doesn't regret any of it. Those early hustles taught him something no course could: what people are actually willing to pay for, and how to build the best possible customer experience around it. He later taught himself HTML and JavaScript to build Seal Munch, an early Yelp-style local listings and coupons site, going door to door to sign up restaurants himself. It wasn't scalable. It was, in his words, "a really good way to build grit over time."
Choosing corporate as a means, not an end
Given that entrepreneurial start, the obvious question is why Sean went into corporate roles at all. His answer is pragmatic: each company was a deliberate learning bet, not a retreat from ambition.
At his early roles he learned email marketing and how to deliver service to Fortune 500 clients. At Amazon, he learned how to deliver value at genuine scale. What he carried between every one of those jobs was the same entrepreneurial urgency: "It's important to have that entrepreneur mentality even if you're working at these big companies, so you can be scrappy and have that sense of urgency to make sure you're delivering the best experience for your customers."
That urgency is also what let him move through the ranks quickly, and what he's learned to watch for in others: the people who treat a corporate job like it's their own business are usually the ones rising fastest, and usually the ones other teams find hardest to keep pace with.
The Jeff Bezos email that redefined "deep dive" leadership
Sean's biggest lesson from Amazon wasn't a strategy framework. It was a single email.
He had launched a campaign on the Amazon homepage. Buried in the legal fine print was a spelling error. Jeff Bezos found it, took a screenshot, and sent it down the chain with nothing attached but the image and a question mark. "I was scared shitless," Sean admits. He didn't get fired. But the moment stuck: a leader running one of the largest companies in the world had taken the time to read the fine print on a homepage banner and catch a typo.
"That's the level of detail that's expected," he says. "I loved it. It's like, deep dive, it's a leadership principle." He took it to heart, and now expects the same from the people he leads: no job beneath you, no detail too small to understand end to end.
He's careful to draw the line, though. Leadership shouldn't be reviewing every email that goes out every day, that isn't scalable. It's about knowing when to be involved, on the initiatives that matter, before they launch. "For really big initiatives, the go-to-market, how we represent the product, the leadership team should be involved. And then once it's out the door, we get a lot of data to understand how we can make it better. The teams can start optimising, iterating, executing."
Founder mentality doesn't disappear at scale
Sean saw the same pattern play out at TikTok. The company's founder, Alex Zhu, would sit in the room reviewing user experience designs directly, giving feedback down to where a button should sit. On the biggest launches, he was personally in the review, not receiving a summary of one.
Sean calls this "the founder mentality": no matter how large the company gets, if you started it, you stay involved in everything about the business. "That mentality has never gone away," he says, pointing to what Amazon itself calls Day One thinking. It's a level of care that's harder to instil in people who didn't build the thing, but it's the recognition that this extra step always exists, and the best leaders keep reaching for it anyway.
Failure is the evidence you're swinging big enough
Sean tells his team plainly: failure is part of the job. "If everything works all the time, it definitely means that people are not taking big swings, they're just iterating and optimising on things that will work anyway."
His process for big bets is deliberately lean: talk to customers, understand the real problem, build the smallest version that tests one core assumption, and validate fast. "We try to validate the solution quickly, so we fail fast if it's not working." Early in his career, his mistake was the opposite: assuming an idea would work and spending months perfecting it before launch, only to find out no one wanted it. Now the discipline is to build the MVP, test the one functionality that matters, and only invest further once it proves out. If it doesn't, iterate or move on.
And stepping outside his comfort zone hasn't stopped costing him something. Public speaking, podcasts, keynotes in front of thousands of people, none of it came naturally. "I was not comfortable at all," he says. "What if I say the wrong thing, what if people see how nervous I am." The fix wasn't confidence arriving on its own. It was treating it as a skill: fumble, make mistakes, get better slowly, and keep going.
Building culture takes longer than you think
Managing a larger team brought a different kind of discomfort: building the processes and culture that let people collaborate well, not just execute individually. Sean describes it as working out the different personalities of the leaders around him, getting everyone aligned on mission and purpose, and giving people the flexibility to make their own decisions inside a clear vision.
"I heard somewhere that it takes at least a year to change culture," he says. There's no shortcut: get the right people in the right seats, give them a clear vision, build the collaboration mechanisms, and let the alignment compound over time.
On staying grounded amid competitors copying his work, his answer is consistent with everything else: keep the focus on the customer. "What is it that we could potentially do to make our customers' lives easier? That's number one." He's watched that competitors tend to avoid the hardest problems, which is exactly why solving the hardest problem is the differentiator. "If it's easy, everyone's going to do it. There's no shame in the copy game, but if you're always looking at your competitors, you're always second, you're always following."
Modelling rest without making it a rule
Asked how he looks after himself while being this invested in the work, Sean is direct about the balance he tries to model rather than mandate. He doesn't set fixed hours for his team: "You don't have to work eight hours today, or nine, or twelve, whatever it might be." Instead, he looks for people who are genuinely passionate about the work, gives them the flexibility to set their own pace, and makes it explicit that nobody should feel like they're on call permanently.
What he models personally: taking real time off, coming back and telling the team how much fun he had, sharing pictures, normalising sick days without guilt. "It's really important, when you take time off, you reset, clear your brain, come back with more creative thoughts and ideas." The expectation isn't rest instead of hard work. It's rest as part of what makes the hard work sustainable.
What leadership actually means
Asked to define leadership in one answer, Sean lands on three things. First, setting the vision, mission and purpose. Second, empowering teams to actually meet that vision. Third, and this is the one he emphasises: being humble enough to know what you're good at and what you're not, and having the right people around you to close that gap.
It's a definition that ties his whole story together. The can-collecting kid, the Amazon deep-dive discipline, the TikTok founder mentality, the fail-fast product process, all of it sits underneath a leader who knows his own edges and builds a team to cover them.
