A man and woman pose outdoors with a black and white dog, with green grass and mountains in the background.
People riding horses outdoors with mountains and cloudy sky in the background.
Group of people smiling and posing together in a living room, some making shaka signs, with a man wearing a baseball cap and a woman in a red shirt in the center, and children in the front row.
Two smiling people, a man and a woman, on a sailboat holding the steering wheel, with a body of water and multiple sailboats in the background.
Group of six men in Brazilian Jiu-Jitsu gis standing side by side inside a martial arts gym, smiling and making the shaka hand gesture. They are in front of a wall with framed pictures and a large circular logo reading 'Relson Gracie Academy'.

As a Certified Financial Planner® (CFP®) and Enrolled Agent (EA), I help individuals and families plan confidently for retirement and navigate the complexities of managing their wealth throughout life. My approach integrates investment management, tax-efficient strategies, and comprehensive financial planning to help clients make informed decisions that align with their long-term goals and values.

With a focus on retirement income planning, tax minimization, and risk management, I guide clients through every stage of financial life from accumulation to distribution and legacy planning. Whether it’s structuring investments, addressing insurance and long-term care needs, or developing multi-year tax strategies, my goal is to bring clarity and confidence to each financial decision.

I also host the Hawaii Retirement Show podcast, where I discuss a wide range of financial planning topics and interview distinguished guests from Hawaii and across the country, sharing insights to help listeners make informed choices about their financial futures.

I believe that true financial success isn’t just about building wealth; it’s about creating a plan that supports the life you want to live, now and into the future.

Personal:

  • I was born and raised in the suburbs of Philadelphia. It was there I met my wife, Jacy, and followed her back to Oahu in 2008. After spending one year in Lahaina, I have called Kaneohe my home ever since.

Hobbies:

  • Traveling, sailing, and longboarding small waves.

  • Playing Fullback/Center-back for the Ohana FC men’s 35+ soccer team.

  • Going for walks/hikes with my border collie daughter, Toba girl.

  • Learning and training in Jiu-Jitsu with the great people at TeamHK.

  • UH Baseball games at Les Murakami & traveling to watch the Phillies.

Education:

  • May 2015 - BA, Business Administration - University of Hawaii

  • December 2018 - AAS, Applied Trades - Honolulu CC

  • May 2013 - AA, Liberal Arts - Windward CC

Certifications / Licenses:

  • CERTIFIED FINANCIAL PLANNER® ("CFP®")

  • Enrolled Agent (EA); admitted to practice before the Internal Revenue Service.

  • Electrician (Ship & Boat), U.S. Department of Labor

  • Electrician, U.S. Department of the Navy

Professional Experience:

  • June 2022 – Present: Financial Advisor, Toba Financial LLC

  • May 2023 - Present: Host, The Hawaii Retirement Show

  • Jan. 2024 – Dec. 2025: Budget Analyst, State of HI – DOT – Airports

  • June 2024 – July 2024: Financial Planning Extern, Amplified Planning

  • Sept. 2021 - May 2022: Client Services Specialist, Summit Financial Advisors

  • May 2016 – Aug. 2021: Electrician (Shop 51), Pearl Harbor Naval Shipyard

Certificate indicating enrolled agent status, with text 'Admitted to Practice Before the IRS' and 'Enrolled Agent'
CFP logo with yellow background and black border containing the letters CFP in black text.

Retirement Planning & Investment Management.

I established Toba Financial in 2022 out of a passion for fee-only financial planning and my desire to help friends and family align their capital with their goals and values. My focus and expertise are in Retirement Planning, Tax Planning, and Investment Management.

Toba Financial
Logo for Hawaii Retirement Show featuring a map of Hawaii islands, a wave illustration, and the event name in black text.

Providing Financial Education to the State of Hawaii

The HI Retirement Show is a podcast focused on retirement and financial planning topics for those living in the State of Hawaii.

If you have a question or if there is a topic you would like us to discuss on the podcast, email us at: aloha@hiretirementshow.com.

HI Retirement Show

www.jasoncutitta.com