Broker Check
Kylen Yamakawa, CFP®

Kylen Yamakawa, CFP®

Financial Advisor

When I was 21, I won my first “big prize money” in a pro surf contest. I was stoked! Before that point, I’d never really had any money. What I didn’t realize, however, was how quickly money could evaporate. I didn’t go out and blow the money on a new car. But I did use the money to travel to participate in more contests. And, of course, if you don’t win, the pot doesn’t fill back up. At the time, my physical trainer was the none other than Kimo Middlesworth! Kimo taught me about paying myself first, and compound interest. If I allocated a portion of my winnings to an investment, and that investment grew, then the money that my--money--made could supplement my cash flow. (Crazy concept at the time!) And, if I wasn’t so worried about my cash flow, then maybe I wouldn’t feel so much pressure to win. And if I didn’t feel so much pressure to win, then maybe I would actually start winning again.

Lo and behold, Kimo was right. With my cash flow in check and the pressure off, I started making heats again. The sponsors took notice, and things took off … until it didn’t anymore. But I was OK with that, because the other thing Kimo taught me was the importance of having a backup plan. So, what do you do when your surfing career comes to an end? For me, the answer was to be a financial advisor.  Now, I get to spread financial wisdom to friends still in the surfing world and beyond.

I currently work on a team with Kimo Middlesworth & Cole Yamakawa. We take a collaborative approach when helping our clients. Together, we embody a blend of experience, longevity, and dedication.


You probably like to surf, fish, or dive. But even if you don’t, what’s important is that you are passionate about life and your hobbies. Because if you’re passionate about life, you likely recognize the importance of properly managing your cash flow and investments so that you can spend more time on the things that make you feel alive.


My investment philosophy in action:

Do something today that your future self will thank you for. 


B.A., Finance and Entrepreneurship, University of Hawaii at Manoa

‘Iolani School



Series 7 & 66 Securities Registration

Life & Health Insurance Licensed

Five rules I live by:

  1. Exceed expectations.
  2. Motivation fades, habits are forever.
  3. People may not remember what you did, but they will remember how you made them feel.
  4. A big house with a million dollar view means nothing if you have no one to share it with.  
  5. There are only two people in this world you need to make proud: The 8-year-old version of you and the 80-year-old version of you.

Ready to take the next step?

Please visit our calendar link: to book a phone call, zoom or in-person meeting. We start with a casual conversation – where do you stand now financially, and where would you like to be? Are you just starting out and want to ensure you’re making smart money moves? Or, perhaps you’re ready to enjoy your hobbies full-time, and want guidance on how to generate sufficient investment income.

If we truly feel we can help you, then we can take it from there. No pressure, no pitches. Just honest financial advice. Regardless of whether or not we end up working together, we are confident that we can help you better understand your current financial situation and point you in the right direction.