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Inspiring Conversations with Jake Wingo of Simplicity Financial Planning

Today we’d like to introduce you to Jake Wingo.

Jake, we appreciate you taking the time to share your story with us today. Where does your story begin?
I came into the finance world after working for several years in communications and sports production. I decided that I wanted my work to have a direct impact on other people’s lives. Being able to reduce the stress and anxiety that finances cause for so many people quickly became my main focus. I love talking to clients who are passionate about education in order to empower them to make informed decisions. The feeling of certainty that comes with making informed financial decisions is both unique and powerful.

We all face challenges, but looking back would you describe it as a relatively smooth road?
So far, it has actually been a fairly smooth road. I got licensed and went straight to work without too many setbacks to this point.

As you know, we’re big fans of Simplicity Financial Planning. For our readers who might not be as familiar what can you tell them about the brand?
We built Simplicity Financial Planning on the belief that money should bring clarity, not stress. We take a holistic approach that integrates investment management, tax planning, retirement solutions, and personalized budget coaching into one seamless process. Our philosophy, “Simple Process. Detailed Results.”, reflects our commitment to making financial decisions transparent and empowering. Whether we are helping individuals achieve financial independence or designing retirement plans that reflect a company’s culture, we are known for simplifying complexity and giving clients confidence in their financial future.

What sets us apart is our dedication to generational impact and true partnership with the people we serve. We take pride in crafting strategies that foster long-term stability, respect, and growth, ensuring benefits that extend beyond today. Our vision resonates broadly: financial planning should feel freeing, not overwhelming. We want clients to know that we offer more than services. We offer clarity, confidence, and a trusted relationship that helps build a secure financial future.

How do you think about luck?
I was lucky to be born into a financially responsible family that focused on my future. My mother was an accountant when I was growing up and saved money to send me to college. Leaving college with no debt was lucky for me, but intential and methodical by my parents. I have also been lucky to have good mentors in both my career and personal life that I can go to for advice whenever I need them.

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