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Founded in 2004 by Diane Kennedy CPA, was originally created as a resource for business owners and investors to get cutting edge information on tax strategy and business building.

Over the years has matured and grown its focus to include financial and wealth tools for business owners and investors in addition to its original mandate to provide the best education on tax strategy around.

We’ve recently gone through a major renovation on the site and you’ll notice many new tools to save money on taxes and grow your business.  You’ll also notice the active involvement of several of the Maui Advisors sharing fresh content on the site.

Which brings up the next question…

Who Is Maui Mastermind?

David Finkel and Diane Kennedy

Maui Mastermind® co-creators David Finkel and Diane Kennedy with their first joint bestseller, The Maui Millionaires.

Maui Mastermind is a community of successful entrepreneurs who help business owners build a business, not a just a job for themselves.

We give business owners a concrete road map that lays out the entire life cycle of their business from launch to exit.

We connect business owners to an exclusive network of experts and an upgraded peer group through our formal and highly structured Business Consulting Program.

We help business owners get to the next level through online and in-person trainings and our series of unique events, including our annual $30,000 Maui Mastermind Wealth Summit.

Maui Mastermind’s Core Story

In 2003, David Finkel, along with Diane Kennedy and two other very successful business owners, participated in a private mastermind group with each other. Twice a year they would get together in person for a full day to brainstorm ideas to scale each other’s businesses, give direct feedback on new ideas, and hold each other accountable. In less than 24 months these private mastermind sessions helped David increase his business’s net profit from $1 million per year to well over $3 million per year; they had a similar impact on Diane’s tax education and CPA businesses.

Diane Kennedy and John Jamison

Diane Kennedy with 2-time Maui Mastermind Wealth Summit graduate John Jamison and his family. Maui 2004

It was during one of these mastermind sessions when David and Diane were all commiserating about how at the average 90 minute training class they gave actually took action on what they were learning. Sure there might be 500 or more people in attendance, but only a small fraction of attendees actually applied what they had been taught.

So they asked a powerful question: “What if we were designing the perfect business workshop, what would it be like? How could we flip the numbers so that 95 percent of the attendees immediately applied the ideas they were learning to make a dramatic difference in their business and financial lives?”

Their list of answers included things like, “It would need to be over an extended period of time not just one day…” And, “It would need to be in a beautiful location and a 5-star resort…” And most important of all, “We would have to pre-qualify every person who attended to make sure they were absolutely committed to playing full out and USING the ideas they were learning…”

At first they were just talking hypothetical, but then David turned to Diane and the other two mastermind partners and said, “If you’re going to be a bear, be a grizzly bear, so pull out your calendars and let’s schedule this event right now.” They looked at him like he was crazy, but they stepped up to the challenge, and thus came to be the first ever Maui Mastermind Wealth Summit at a luxury resort in Maui.

That first year the event was sold out. Midway through the event the response was so powerful and the feedback from participants so positive they decided to make it an annual event. It’s been over 8 years now and this $30,000 week-long business owner and wealth retreat continues to be the most exclusive experience of its kind. Considering that over 60 percent of the graduates sign up to come back year after year after year, they must be doing something right!

Finkel Pahl Thompson

David Finkel with Melissa Pahl (2-tme grad) and Jason Thompson (first time participant). Maui 2009.


That event became the foundation of the Maui Community of business owners, with these super-successful entrepreneurs and the Maui Advisors “paying it forward” to the next generation of business owners by sharing with them the things that made a difference in their businesses and lives. Collectively over the past 20 years, the Maui Advisors have started, scaled, and sold over $2 billion of businesses.

Founders Donation

Event creators Peter Conti, David Finkel, and Diane Kennedy donating an additional $100,000 to 8 of the Maui charities. (Maui 2004)

To this day Maui Mastermind shares the same methodologies its top Maui Advisors have used in building and scaling their own businesses as they share with business owners around the world how they can build a business, not a job. They give business owners a complete road map through the entire life cycle of their businesses, from launch to exit.

And they remain true to the Maui vision that wealth is more than just the money—it’s about the quality of our relationships and impact we have on the lives of others. Over the past decade, the Maui community of business owners has raised over $5.1 million for dozens of charities around the world.  (To learn more about Maui’s charitable activities and see how you can get involved and impact the world, just click here.)

Thank you again for choosing to engage with and Maui Mastermind®.  We believe that together we can make a real difference in each other’s lives.