Building Big from Island: Conversation with Hawaii Tech Founder Tyler Shaeffer

While many founders still believe that serious tech companies must grow in San Francisco, New York, or Austin, Hawaii-based entrepreneur Tyler Shaeffer is quietly proving otherwise. Fresh off another successful funding round for his AI therapy startup, Tyler shares what it really looks like to build, scale, and lead a high-growth tech company from the islands—and why Hawaii may offer more advantages than most investors realize.

Meet Tyler Shaeffer: an outdoor enthusiast and founder of Mental, a psychological health app geared towards men.

Raising Capital from Hawaii: Network Over Location

Asked about fundraising challenges as a Hawaii-based founder, Tyler is quick to flip the narrative.

“I actually think it’s mostly about network, not geography,” he explains. “If you’ve done something impressive and other impressive people trust you, I don’t think VCs are picky about where you live.”

Before moving to Hawaii, Tyler spent years building a strong career and network in San Francisco. That foundation has paid dividends. But he’s confident that founders don’t need to be in Silicon Valley to be taken seriously. What matters is credibility and relationships, not zip codes.

The Talent: Hiring in San Francisco, Living in Hawaii

Is talent the #1 bottleneck for Hawaii tech companies? Tyler answers honestly.

“I’m hiring my engineers in SF for three days a week in the office, while I live in Hawaii. If I was exclusively hiring engineers in Hawaii, that would be tougher.”

For high-growth tech teams, hybrid geography is becoming normal. The key is knowing where certain roles need to be based and where founders can live while still running an elite team effectively.

Go-to-Market from Hawaii: Less Impact Than You’d Expect

For a digital product like Tyler’s AI therapy platform, location simply isn’t a constraint.

“Our go-to-market isn’t impacted by me being in Hawaii at all,” he says. The product is digital. The customers are distributed. The playbook doesn’t change with the time zone.

Founder Lifestyle = Better Decision-Making

When asked what mainland investors misunderstand most about Hawaii startups, Tyler doesn’t hesitate:

“The power of lifestyle.”

He breaks it down simply: founders make hundreds of small decisions, but only 2–3 big decisions a month actually change the trajectory of a company.

“Going in the ocean every day, staying fit, living aloha, having a laid-back community—those things make me better at my most important job: making the big decisions.”

It’s not about working less. It’s about working clearer.

Brain Drain & the Mainland Temptation

Tyler admits he’s considering a temporary move back to San Francisco—but not because Hawaii is holding him back.

“If I move, I’ll miss Hawaii like crazy and probably move back after my company exits,” he says. “The company will be successful either way.”

It’s a refreshingly grounded perspective: Hawaii is home, and the company’s future isn’t dictated by its HQ address.

High Cost of Living vs. High Quality of Living

Tyler rejects the idea that Hawaii makes founders complacent.

“You could be living in Palo Alto making slow decisions. Those are states of mind.” And he puts the tradeoff bluntly—and effectively:

“Should I live in a shitty unpleasant place just so I work a few more hours a week out of sheer misery? Why?”

Productivity, he suggests, comes from discipline, not suffering. Hawaii’s environment simply removes the noise.

On Exits

With his latest raise behind him, Tyler is clear-eyed about where a future exit might come from.

“No, the chance of a Hawaii exit was never in the cards. Our exits are IPO, or acquisition by a big healthcare payer or a large tech firm.”

It’s pragmatic and consistent with how most high-growth ventures operate globally.

Local Lessons: What Hawaii Taught Him About Leadership

One of Tyler’s most impactful insights comes from the ocean.

“The paddling community I’m part of taught me the power of synchronized pushing. When the canoe moves, it’s because all six of us are in sync and pulling our weight.”

That mindset: alignment, teamwork, shared power, guides how he builds and leads his company.

Looking Ahead: A Vision for Hawaii’s Tech Future

Tyler doesn’t pretend to know exactly where he or his company will be in five years. But he knows one thing:

“I want to encourage more local tech entrepreneurship however I can. I gave a guest lecture at UH and the students were incredibly engaged. I’d love to help build more ambitious tech founders in Hawaii.”

Final Thoughts

Tyler Shaeffer represents a growing wave of founders proving that Hawaii isn’t a barrier to world-class tech innovation—it’s an advantage. With the right network, discipline, and vision, life on island can empower sharper decisions, stronger teams, and more balanced leaders.

If the next generation of Hawaii tech founders follows the wake Tyler is carving, the future of our tech ecosystem looks incredibly bright.