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  • Writer's pictureJay Judas

Tier One Interview: Madison Chaney

This month, our CEO, Jay C. Judas, sits down with Madison Chaney, Project Manager at Legacy Planning Partners. The pair discuss being part of, and working with, multi-generational businesses, how to grow the ranks of LGBTQ+ people in the life insurance industry and where to eat in Perkins, Oklahoma. Read it all below!

Jay: Madison, thank you for participating in this month’s Tier One Interview. When I met you at this year’s Finseca Advanced Markets Conference in Washington D.C., I immediately put you on the list to interview. Then, when I ran into you at another life insurance event in Dallas in September and learned you are a third-generation producer, I knew this conversation couldn’t wait another month. Get us started by talking about your firm in Oklahoma City, Legacy Planning Partners, and your work there.

Madison: Thanks Jay, I appreciate this opportunity. As you mentioned, I’m the third generation here at our firm. We help our clients focus on two primary planning areas: legacy and succession. One of our competitive advantages is our family’s combined experience of 95 years working with family businesses. Through the years, we have firsthand experience that a lack of planning in either concept can be equally detrimental to their family and employees. Everyday we strive to help entrepreneurs build an intentional and effective legacy and succession plan to impact several generations.

Jay: When I ask most of our interviewees to talk about how they found themselves in the life insurance industry, it was rarely by planning to be there. This was not the case with you. Am I correct in saying that you wanted to help people through life insurance since you were 10 or 11 years old? Tell us about this and your upbringing that led to this precocious decision.

Madison: Yes, that is correct...well, mostly correct. I wasn’t sure what exactly my dad and grandfather did for a living, but I knew I wanted to be a part of it. Often, my dad would take me on weekend appointments to see his ranching clients. After we’d leave the client’s house, I’d start drilling dad with various questions in an attempt to learn more about the business. I was intrigued by the different ways life insurance can help solve family issues - from providing liquidity in the event of untimely death, family income to maintain financial independence or equalizing the estate for those that aren’t staying involved in the family business or the ranch.

Fast forward a few years, I wasn’t giving up on working alongside my dad and grandpa. They finally agreed to allow me to interview for a summer internship with their company. The internship consisted of the old fashioned person-to-person cold calling. I think they were trying to run me off, but I truly had the time of my life that summer. Here I am six years later, loving the difference we get to make with our clients.

Jay: That’s incredible, Madison - that for three generations, your family has worked with entrepreneurial business owners with both business and personal life insurance needs. With many of your clients, their business is their largest asset, so you have to plan for some sort of business exit of the patriarch or matriarch and then incorporate this into an estate plan. You don’t just conclude your planning work with the first generation, you go further and insist on open and honest communication with G2 and G3. What does this look like?

Madison: Right, I think our firm found through the years that our clients and their entrepreneurial spirit created the wealth and the thought of it being squandered really disturbs them. We spend a great deal of time talking through what their hopes for their legacy and succession will accomplish within their family. Often, family unity and community are on their list. When we talk about substantial wealth transfer, one of the most important notes is the education and responsibility of future generations. Our team trains and mentors G2 and G3 to empower their decision-making skills, involve them in the philanthropic processes and talk through the family’s values and vision for the future.

Grandpa Mike Chaney has two favorite sayings that fit our multigenerational planning focus: First, “A successful baton pass is not accomplished by handing up the baton from the grave,” and, second, “I’ve sold life insurance for 55 years, you can’t hurt my feelings.”

Jay: Maybe I should interview Grandpa Chaney! The extra steps you take with your family clients is a sign of your high level of service. This includes insisting that some financial discipline be placed on younger generations, especially those who will be living off the wealth created by their parent or grandparents. Why do these younger family members need this and how do you work with them?

Madison: I think this where our clients benefit from our firm’s many years of experience. People who get something for nothing often are the most unhappy people. It is our belief that we feel a sense of accomplishment by what we are able to achieve and not by what our last name is or what our family did to make its wealth.

We spend a lot of time going over this with each generation. The majority of our clients have no desire to let their next generation “live off their wealth”. It’s more of a mind set of “how can my wealth launch them further than I ever got”. Accordingly, we focus heavily on financial education with strategies like savings matching, inter-family business loans and encouraging the creation of business plans.

Jay: Let’s shift the conversation to discussing an area that is both a weakness and an opportunity for the life insurance industry. There is almost a complete absence of LGBTQ+ forward facing producers working in the affluent area of the market. When we spoke a few weeks ago, I told you I would be interested in obtaining your thoughts about growing this number. You flipped this around and had, not only thoughts on how to grow LGBTQ+ involvement, but a way to make other marginalized groups in our industry successful. Plus, you have a business plan to do so!

Madison: I think this is a tough subject when it comes to our industry. Being from Oklahoma, I have always taken the stance of “what’s my business is my business”. As I have matured in my career, I’m not so certain of that stance anymore. When we spoke a few weeks back regarding this interview, I wasn’t too keen on speaking to this issue.

When originally asked about the LGBTQ+ producers across the industry, all I could think about was the fact that there are probably more producers than we realize. Many of us hide who we truly are, me included. I think that is unfair to our peers, clients, and family. The fact is that our industry has been dominated by white men serving white men.

On a positive note, I believe that this is changing. Many more advisors of various ages, races, and genders are joining this wonderful profession and are able to service a more diverse clientele. Why are we all still hiding who we are in our clients’ eyes? My sexuality is never the first topic of discussion with my clients, but as my relationship with my clients grows and I get to know more about their family and family dynamics, its only human nature that in return they want to know mine.

And I’m working hard on being as transparent with them as possible. As far as being a woman in this business - I’m not a big fan of excuses and I don’t subscribe to the “I’m limited because I’m a woman.” So, when you asked why our industry has an absence of LGBTQ+ and women advisors, I believe they could be intimidated by our industry and don’t realize the impact they can make.

It is a challenging industry to thrive in with no team or substantial infrastructure. In my career, I want to bring those individuals into our industry, give them a track to run on and to financially support them until they have built up their own client base. My hopes are, in doing that for them, they will, in turn, do that for someone else. The world as we used to know it is changing. People are starting to see each other as people - not as male, female, gay, straight, etc.

Jay: I completely agree with you, Madison. If producers sell only to clients who look like them and have shared the same experiences, it limits not only who is receiving professional life insurance advice, but also the talent pool our industry needs to expand and to serve clients with diverse backgrounds.

As much as you clearly love helping people with their life insurance and planning needs, you and your wife, Kasey, do like to do other things outside of your company. How do you spend your free time?

Madison: My wife and I are avid sports fans. Of all sports. Whatever is playing in season you can bet that we are keeping up with the games religiously! However, our favorite team to root-on are the Oklahoma State Cowboys & Cowgirls - GO POKES!. We really enjoy traveling and camping with our two dogs, Samson and Poppy. In the summer, we enjoy taking our boat out on Oklahoma lakes. My passion, outside of helping families solve problems, is hands down fishing. One of my favorite sayings is a bad day of fishing beats a good day of anything else!

Jay: It has been a treat speaking with you, Madison. You have such a bright future ahead of you and it makes me happy knowing the life industry is in such good hands for decades to come.

We have moved to our restaurant question which, for you, as a former rancher, will be either very easy or quite difficult. Without naming a steakhouse or a steak dish, tell me about a few restaurants that I absolutely have to visit and what I need to eat there.

Madison: Thanks again for allowing me to speak with you on these topics that I am passionate about. When it comes to food, the Chaney philosophy is “some eat to live and our family lives to eat!” If you or any of your readers find yourself in Perkins, Oklahoma you must go to El Mexicano and order the Papa Poblano It is to die for! I’d say when it comes to a dish from a common restaurant your readers could more easily visit, I’d have to go with Capital Grille’s Lobster Mac and Cheese.


Since its inception, Life Insurance Strategies Group has solely focused on the individual high net worth life insurance market. We do not sell products. This allows us to offer unbiased, pragmatic advice. Visit us at

1 Comment

Nov 16, 2022

I’m so proud of my little former 3rd grader, Madison Chaney! She was such a positive, fun-loving girl! I’m fortunate to have met her at 8-9 years old! What a great person! Love you, Maddie!🧡

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