Broker Check
Kimo Middlesworth, RFC, CFS, MSFS

Kimo Middlesworth, RFC, CFS, MSFS

Financial Advisor

After finishing college, I started my career in education, teaching children to read.  Shortly after accepting a dorm advisor position at Kamehameha Schools, I bumped into an old high school friend who was in the financial industry.  We sat down to catch-up and he shared basic financial concepts like “paying yourself first”, the Rule of 72 (compound interest) and the importance of investing to pursue your financial goals.  The conversation left me amazed and honestly, a bit frustrated!  Some of the concepts seemed so simple and obvious, yet I didn’t know them! I remember thinking to myself, “I’m in my late twenties, a college graduate and have been working a few years… How is it that I’ve never seen, heard or been taught any of this!?” I became obsessed with learning and immersed myself into as many books, financial news and magazine articles I could get my hands on.  I felt the need to share the concepts I had learned and realized that I could continue my role as an educator by becoming a financial advisor and teaching people about their finances.

Reflecting on 30+ years of being an advisor, it’s moments like when a client retires, buys their first home, pays off their mortgage or is able to send their child to college that makes me love what I do.  I genuinely enjoy the process of putting together a plan, implementing it, and the years of hard work it takes to bring it to fruition.  Being an advisor brings me a great sense of joy and see it as a lifelong journey.  I believe that people value an advisor with experience, but it’s also important to have an advisor who will be there for you to see the plan through (with experience comes age!). I currently work on a team with Kylen Yamakawa and Cole Yamakawa, who have proven to be equally trustworthy, knowledgeable, and passionate about helping people with their finances. As a team, we can assure clients that they will be taken care of throughout their financial journey.


You are excited to map out your path to financial wellness. Regardless of the level of your understanding, you are interested and open to learning more. You are looking for a financial advisor that believes in strong communication and is looking out for your best interests. As updates present themselves from both a client’s and/or advisor’s perspective, keeping in touch will allow the financial plan to stay on track.


My investment philosophy in action:

“Making the simple into complex is easy, true genius is making the complex into simple.” – Charles Mingus, the great jazz musician.


Masters of Science in Financial Services, The Institute of Business and Finance, California

B.A., University of Hawaii Manoa

Kailua High School


CFS, Certified Fund Specialist

RFC, Registered Financial Consultant

Series 6, 7, 63, and 65 securities registrations

Life, Health, Property & Casualty insurance licenses

Five rules I live by:

  1. Practice Kuleana (responsibility) with family, friends, clients, and others as best as and as often as possible.
  2. Every day is a blessing.
  3. Take the time to laugh, but be serious and focused when needed.
  4. Discipline is the bridge that links goals to accomplishments.
  5. The early bird gets the worm or the dawn patrol surf.

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.