Wendy Jestings


Wendy Jestings

Growing Up Young

I grew up on the east coast in a blue-collar family as the oldest of three girls. I earned the right to challenge my thinking and others would say the status quo early on in my life. I grew up way before my time. I was a child living in an adult body. I created new identities for myself between the ages of 11 and 16 so I could fit in with my peers. Now, of course, I see that having years’ worth of street smarts helped me be the woman I am today. I wouldn’t change those trials and tribulations and life lessons for any amount of money or prestige today. I embrace my uniqueness, as it is my greatest gift.


I got denied from following a traditional 4-year college path due to my lack in financial feasibility and my real-life struggle to embrace traditional education. I ended up getting married young, thinking that that would give me the stability and structure I was looking for. It did not, but it did give me two beautiful children, who today are in their early 20’s. I went on to go to school at night while running my business during the day. I continued to build my life resume. At the age of 22, I had my oldest daughter Haley and simultaneously had a childcare center with 12 full-time teachers and 6 part-time assistants.


I got my first job at the age of 10, a paper route, which taught me discipline and hard work. When I was 13 years old, I got my first job at a retail store in a pet department because they thought I was 15 years of age at the time. I choose to work instead of attending parties or playing sports. I wanted to be on a team so very badly, but it wasn’t in the cards for my family to meet the responsibilities of getting me to and from practices. I peaked in the 11th grade when I realized I hated school, and I was able to graduate High School on the East coast a year early and open my first business at the age of 19 years old.


A crazy dream of mine? Running a financial firm, raising two small children by myself. Where do I begin? I felt like life handed me the tough card, the ones without the rules and directions, that said…. Go figure it out. Your personal and professional intellect is what you have to give, go use it and capitalize on the rewards of your talents.


I fired myself from the childcare industry after frustration with retaining good help and being able to be profitable so that I could pay our teachers a livable wage. After going through a tremulous divorce, I recreated myself and entered the financial services industry. I had a passion for enterprise and helping others be in control of their own financial decision making. I had learned early on never to put your own personal and professional worth in the hands of someone else. I was shamed into thinking that I needed a man in my life to be the provider. After having one of the lowest days in my life, I realized I was never going to allow someone to control or own my personal and professional intellectual capital again.


As a financial advisor, I wish that the things that I learned were instilled in me from when I was young. I was grateful for the lessons of saving what you earn and do not spend more than what you make, but I had to go into debt in order to make it. I took my love of teaching and wanted to share it with other young people so they could have the confidence and the financial freedom to make their own tough decisions in life. There is no free lunch, but with mentorship and good role models, anything is possible. Take your life hardships and turn them into life victories; every single thing that didn’t go my way ended up being the catalyst to the next level of personal and professional growth. I empathized with young professionals all the time that they need to get their own house in order first so that they can be open to dealing with whatever life throws at them.

That began my passion for helping my clients achieve their own life of financial significance. I helped them take control of their financial lives.

It was the start of a beautiful relationship with my clients and advisors that trusted and believed in me enough to grow together.

My first client, I remember so vividly. book, soon, my confidence took on a life of its own. I used my divorce and financial hardships as teachable moments with my clients. I help clients take everything they have ever learned about money and turn it on its side. I began making regular appearances at industry events and firms as a public speaker sharing my experiences.
At the same time, I began coaching advisors who were struggling to get their start in this amazing career.


Money isn’t just dollars and cents it’s the freedom to do what you want and flexibility to invest in yourself and others. After losing all of our family’s savings during my long recovery, I was thankful that I was in the industry where I was taught to take care of life unforeseeable outcomes.

I am deeply passionate about money. With or without it, it can be destructive.

It’s not enough to walk into someone’s home and ask them to change their relationship with money and savings. The courageous conversations and the level of intimacy that is shared transform the way we help our clients. There will always be psychological, mental, and emotional barriers that prevent us from taking action around our finances and financial health.

As I developed this whole new way of talking about financial wellness, earning potential, money, and relating to people around their finances, my career matured. The types of issues I have faced and stared down has given me permission to attack anything life throws my way.

I was no longer just “the woman who helps you with a financial budget.” I was a trusted professional who will always tell you what you need to hear and not necessarily what you want to hear.

I began helping people take control of their personal and professional financial lives so they can live their best life. The power of financial freedom is significant, and life becomes more comfortable when you use it for good.

And my audience and I are still figuring out how to balance everything, now that I have continued to evolve.

I am never content; I always want to expand my wings, grow and challenge myself to take on new things.


At the age of 21, I was over $100,000 in debt. I made a decent living, but I had this insatiable appetite for more. Being a teacher, I soaked up mentorship. I surrounded myself we good people and teachers and paid the price of admission through learning and listening and applying fierce skills to real-world experiences. Those early years involved lots of borrowing food, gas money and four for a dollar pasta. But it was worth it. Because, as I slowly climbed out of debt and into the best years of my life. It was the price of admission and knew it was my job to prove that I had earned the opportunity to share my knowledge and intellectual capital with others.


In 2012, I almost had a life-ending career-ending tragedy.

Life has a funny way of throwing curveballs at you when you least expect them.

It was just a typical beautiful Vermont summer on the lake. It was a Saturday, August 4, 2012.

We spent the day on the beach with friends and then went to dinner as a group. We returned to the lake after dinner to sit and watch the sunset, and you can't help to think about how beautiful our state is, we are so lucky to live here. I slipped off a dock in two and a half feet of water headfirst. I broke my next in three places and almost drowned in the water before I could gasp for air. Life was getting really good at throwing me challenges to overcome. I was told that I would never walk again. Against all the odds and many doctors, I did regain my ability to walk again. I spend the next 24 months in a Spinal institute, out in outpatient rehab and learning how to do essential functions for myself again. The lesson I walk away speaking about today all over the country is that we control very little in our lives. One thing was for sure; we do have a choice in how we react to these challenges. Our attitude determines our outcome. That is when I developed my first hashtag #BDR Behavior -Drives -Results. What are your daily actions that are within your control that you can focus on each day? Do you measure your daily results?


I’ve fallen in love again.

Most importantly, I teach myself daily how to love and accept myself.

I’ve gotten re-married.

I have three beautiful children, two of my own and a fantastic stepson in the middle between my two.

I’ve become a mentor

I have become a trailblazer

I don’t have to prove to anyone that I have earned a seat at the table

I am an advocate for others

I have an enormous amount of gratitude for life in all its glory…. The good the bad and the ugly.