Kevin Dias doesn’t think he’s funny. He’ll tell you he’s the Michael Scott of his own company: hilarious in his own head, less so out loud. But in this episode of Humor in the C Suite, Kate Davis sits down with the founder of Ambiki to talk about something harder than being funny: building a fully remote startup where everyone else gets to be. From his home in Oyama, Japan, Kevin talks about jokes flying in the Zoom chat, the moment a teammate told him he’d crossed a line, why humor has to start one-on-one, and the annual hackathon that keeps turning play into product.
Key Takeaways:
- You don’t have to be the funny one to lead with humor. A leader’s job is to create an environment where other people feel free to be funny.
- Humor builds one relationship at a time. Trust has to be earned one-on-one before jokes land in a group setting.
- On a remote team, side jokes in the meeting chat can be the only water cooler there is. Treat them as connection, not disrespect.
- Laughing at a situation and laughing at a person can look identical from the outside. Listen when a teammate says a joke missed.
- Self-deprecation isn’t low confidence. Naming your own weak spots early lets people focus on your ideas.
- If a team only jokes about the lows, humor turns into cynicism. Save some of the comedic energy for the wins.
“Worst case scenario, you can laugh at my cringe LinkedIn posts.”
Humor in Leadership: Making Room for Levity on a Fully Remote Team
Startups swing hard. Kevin describes days that open with the highest of highs, like landing a new customer, and close with the lowest of lows. For a team spread across time zones that never shares a hallway, humor is one of the few tools that can carry people through both. But as Kevin’s conversation with Kate shows, building a culture of levity takes more intention than telling a few jokes.
You Don’t Have to Be the Funny One
Kevin is upfront about where he fits. “I don’t think I’m funny, but I wanna work in an environment that allows for that fun,” he says. He has deep respect for comedians because the craft takes “a lot of intelligence and empathy,” so rather than trying to be the source of the humor, he makes room for it.
Kate calls it knowing your lane. A leader doesn’t need to land a punchline to have a sense of humor, and some of the most effective leaders clear space for their team to bring their full personalities to work. On an innovative team especially, that freedom is part of what keeps people creative.
Humor Starts One-on-One
When Kate asks how relationships get built on a team that never meets in person, Kevin’s answer is specific: not in the group first. “It would be tough to inject humor in the group setting first,” he explains. “It’s building that trust one on one.”
As he gets to know each teammate’s personality and style, the jokes start in those individual conversations. Once enough of those relationships exist across the team, humor in a group setting stops feeling risky. It’s a practical model for any leader trying to build psychological safety: trust scales from the individual up, not from the all-hands down.
The Zoom Chat, the All-Caps Email, and Knowing the Line
One tradition grew at Ambiki without anyone planning it. During the weekly all-hands Zoom call, teammates started trading jokes in the chat while others were presenting. Kevin admits his investment-banking instincts flinched at first, since it could read as rude. Then he reconsidered. “We can’t be too stiff. This is our one chance a week to have fun together.” As long as everyone understands the jokes aren’t coming from disrespect, the chat becomes the office banter a remote team would otherwise never get.
That doesn’t mean humor always lands right. Kevin shares a time a customer sent an email written entirely in capital letters, and the internal chat lit up with jokes about being yelled at. A teammate later came to him and said making fun of customers wasn’t professional. Kevin agreed. “I wasn’t viewing it as making fun of that customer, I was viewing it as making fun of the situation. But you have to understand how different people can view things different ways.”
It’s one of the most useful moments in the episode, because it models what healthy workplace humor needs: a team where someone feels safe enough to raise a concern, and a leader willing to hear it.
Self-Deprecation as a Confidence Move
Kevin recently released The Problem-First Method, and he’s candid about the imposter syndrome that came with writing it. His solution was to open the book with self-deprecating humor. “If I can make fun of myself first,” he says, readers can set the credibility question aside and judge the ideas on their merits.
He uses the same approach at work. When he started posting on LinkedIn to build brand awareness for Ambiki, he didn’t pitch it to his team as an expert with a guaranteed plan. He pitched it as a theory worth testing, with a built-in fallback: at worst, they could laugh at his cringe posts. It’s a balance of enough confidence to move toward a vision and enough humility to admit you might be wrong, and it’s a large part of what makes authentic leadership believable.
Joke About the Wins, Too
Kevin’s biggest caution for startup leaders is about where humor points. “If you’re always joking about the negative, it can become this vicious cycle of a negative culture,” he warns. Venting through humor is natural, and it helps teams survive the hard days. But when the jokes only ever land on the lows, cynicism becomes the culture.
His fix isn’t less humor. “You gotta use humor in the right moments to bring levity to the tough situations, but you also wanna joke a lot about positive things.” For leaders focused on employee engagement, it’s a simple test worth running: are the wins getting as many laughs as the losses?
Hacks: Play That Ships
The episode title comes from Ambiki’s annual hackathon, which was happening the week Kevin and Kate spoke. The team splits into four groups, each tackling a prompt Kevin sets, and spends two days working with teammates they don’t usually get to collaborate with. At the end, everyone presents to judges, and the winners walk away with trophies and t-shirts.
It isn’t just a team-building exercise. Almost every year, something built during the hackathon has made its way into the main product, and in past years customers have served as the judges. Kate connects it to a study where one advertising agency was asked for its best campaign ideas, and another for its worst, and the “worst” ideas came out funnier and stronger. Loosening the rules for two days is often where the best work shows up.
For a fully remote team, the hackathon does double duty: it’s the closest thing to meeting a new coworker in the hallway, and it’s proof that play at work can end up on the product roadmap.
About Kevin Dias
Kevin Dias is the founder of Ambiki, an EMR and practice management platform built for pediatric speech, occupational, and physical therapy practices. He previously served as CTO of Sidekick Therapy Partners, where he helped build them a bespoke practice management system that supported Sidekick’s growth from about 70 to more than 180 clinicians in three years. His career has spanned investment banking, English teaching in Japan, translation technology, and healthcare software, but the common thread has always been solving messy, real-world workflow problems. In April 2026, he released The Problem-First Method, a book about helping teams avoid building solutions in search of a problem. Kevin lives in Oyama, Japan with his wife and three sons.
Connect with Kevin:
– Website: https://www.kevinsdias.com/
– Ambiki: https://www.ambiki.com/
– The Problem-First Method: https://problem-first-method.com/
– LinkedIn: https://www.linkedin.com/in/kevin-dias-ambiki/
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