Entrepreneurship Still Belongs to the Exceptions, Content Creators

Living in Hawaiʻi is its own stress test, especially for business, innovation and creative entrepreneurs. By most accounts, Hawaiʻi is one of the most expensive states, with the highest rent- and mortgage-burdened households, rising healthcare premiums, and virtually no safety net for early-stage risk. Layer onto that one of the lowest-ranked and least diverse innovation economies in the U.S., and the outcome is predictable. Even compared to other tourist-driven, extractive recreational economies, we are…lacking. 

Hawaiʻi is not short on ideas or talent. We never built a system-level investment, a would-be viable path for a scalable, high-growth company to emerge and recycle capital, talent, and experience back into the ecosystem. In an outsized way. As a result, very few businesses reach scale without being exceptions; high-growth founders rarely get to the point where they can send checks to the next generation and keep building. We have yet to create meaningful interventions, pathways, or economic conditions that prioritize a diverse economy. (We know this intuitively and definitively.)

Last year our local venture group handed out an “intrapreneur” award…to a bank employee, as it often does. (I’m sure this person is excellent at their job.) But this kind of recognition tells you everything about the fabric of early-stage building. It regresses toward safety and incumbency and not risk, nor new value creation. Hawaiʻi’s ecosystem, largely, is designed to filter out and sideline early-stage entrepreneurs quietly. And when that happens, durable, locally anchored impact weakens. We feel it. 

The clearest bright spots are emerging outside the traditional economic development ecosystem entirely. Creators are opting out. They earn globally, build audiences directly, and don’t require permission from local gatekeepers. They control distribution, own their narrative, and create optionality beyond Hawaiʻi’s capital constraints. Many are multi-threat talents and exceptional because they learned to bypass systems that were never built to support them anyway.

Jamie O’Brien may be the King of Pipeline, but his real leverage comes from the 1.3 million subscribers who have watched him surf, work, and build in public for over a decade (and now, have a baby, too). In 2026, he launches Funday Surf with boards, apparel, and gear. It will be an “overnight success” built on years of audience trust and distribution ownership. Shar Tuiasoa, aka Punky Aloha, followed a similar arc, turning design talents into global reach: a Disney partnership, a two-book deal with HarperCollins, and clients including Apple, Target, and Amazon. (And Bretman Rock, another content creator, who came back home.)

Their success can feel almost heroic, but it’s also diagnostic. Creators who combine craft, audience, and distribution seem to outperform Hawaiʻi’s traditional economic development models, not because they are favored by the system, but because they learned to work around them. In 2026, look for more Jamie O’Briens and Punky Alohas to emerge. The system will not suddenly change, but the most capable talent now has relatively new and more proven distribution models to force the issue.

…

Back to 2026 Predictions