Tier One Interview: The Cowarts

This month, Jay sits down with Michael Cowart and Michael Cowart, Jr., partners at The Cowart Group, the Mobile, Alabama executive benefits firm now doing business in 28 states. The Cowarts argue that most advisors get executive benefit planning backwards, leading with the funding vehicle when the only question that actually matters is whether the plan design will move the people it's built for. They walk through what that looks like in practice, including why a SERP that vests at 65 won't retain a 35-year-old key executive no matter how good the numbers look on paper. They also discuss how family-business friction has to be surfaced before any planning can begin, and the good-cop/bad-cop dynamic that makes their father-son partnership work. Plus, the infamous restaurant question. Read on to learn more!

JAY:  This month, I am turning my attention to the executive benefits space and am thrilled to have the opportunity to catch up with two experts who excel in this market and are as busy as ever. For reading clarity, I am going to refer to Michael Cowart as Michael and Michael Cowart, Junior as Michael Junior. Obviously, you are a father and son team whose firm, The Cowart Group, is based in Mobile, Alabama and has customers throughout the South. Tell me more about your firm and your roles in the organization.

MICHAEL: Thanks, Jay. We were touched to be asked to participate in the Tier One Interview Series  Yes, you are correct, we are an executive‑benefits firm focused on consulting, designing, implementing, funding, and administering executive benefit packages for business owners and key leaders. That’s our core work, but once you start advising owners, the conversations naturally expand. They come to us with everything from business‑transition questions to management succession, acquisitions, family dynamics, and eventually estate planning.

My son, Michael, and I are partners, and we really do divide and conquer across the whole business. Marketing, staff leadership, shaping the firm’s vision, driving growth – we are both involved in all of it, which keeps things fun. For a long time, we were mostly a regional firm, but we have been fortunate to grow nationally. At this point, we’ve done business in 28 states.

MICHAEL JUNIOR: It's been fun to look back at where we started versus where we are today. When I came home and joined my father in 2017, he gave me the flexibility to learn all the different parts of the business and figure out where I could add the most value. It didn't take long to figure out that finding a niche was better than trying to be everything to everyone.  Calling on business owners and CFOs also turned out to be a much more natural fit for a 28-year-old than calling on high-net-worth individuals. So, we kept narrowing our focus until executive benefits became the core of what we do. As for how we operate now, we're partners. We coordinate our calendars so that most of the time, if there's a client meeting, we are both walking in the door.

JAY:  My company has a solid network within the high-net-worth life insurance industry and there has been quite a bit of buzz about the way both of you offer solution-based planning to corporate clients. I am curious how each of you found your way to the life insurance industry. Michael Junior, it may seem apparent that you simply joined your father…but wasn’t the case, was it?  You actually planned your education with an eye on the life insurance industry.

MICHAEL JUNIOR: I was fortunate to spend time working in dad’s office for a couple of summers growing up. At the time, I really had no idea what he did – I just knew that it was finance and life insurance related. I also admired the discipline and professionalism that he brought to work every day. I could have gone to school with a goal to work in any career path, but I knew I always wanted to come home and work alongside him.

I experienced four fantastic years at the University of Alabama that came with a few football national championships. Coincidentally, their business school was enhancing many of their programs. Aside from having the option to major in Finance, they had a risk management specialization available specifically for the life insurance industry. I studied that specialization because I know that it would help me in my path to joining Michael Sr.

Coming out of school, I knew I did not want to go home immediately, so I was able to find a job as a wholesaler with Jackson National in their Nashville office. This was a great opportunity, in that it provided a path for licensing and sales training. On the internal sales desk at that time, every Friday you had to participate in a “smack down”, in which you had to give a two minute speech on a pre chosen topic to the floor – like a fund selection, or planning technique, and the team voted on a winner, and critiqued you. Activities like this really helped my growth.

After a few years, Michael Sr. and I had a routine where every morning on my 30-minute commute, we'd talk. Life, Alabama football, golf, work. And one morning he said, “I know I told you whenever you're ready… but it might be a good time.”

MICHAEL: My path was a little different. Coming out of college, and after a lifetime of competitive sports, I knew two things about myself: I wanted to compete, and I wanted to own my own business. The life insurance and investment world was one of the few places where you could build something without needing bank financing, so that’s where I headed.

I started in the career‑agency system with National Life of Vermont, got my training and licensing, and jumped right in. National Life does a lot of work with business owners, especially around creative ways to use the corporate checkbook to fund selective, personalized retirement strategies. That’s where I first learned about deferred comp, Section162 executive bonus plans, split‑dollar planning — all the tools that eventually became the foundation of what we do today.

Pretty quickly, though, I realized something important: no single carrier can be everything to every client. If you want to be a true advisor, you must represent the client, not the company. That pushed me to start my own firm and build a team around that philosophy.

And honestly, if you’re going to work in the business owner marketplace, you need to be a business owner yourself. You need to understand what it feels like to make payroll, provide benefits, deal with growth challenges — all the things your clients are living every day. That experience has shaped how I approach planning and how I relate to the people we serve.

JAY:   Michael, you are undoubtedly a seasoned professional when it comes to implementing executive benefit programs. I will ask more about the specific solutions later but, first, it is important to hear the types of problems clients are asking you to solve.

MICHAEL: For sure, Jay. Whether we’re talking about executive‑benefit planning, business‑succession work, or estate planning, the starting point is always the same: we have to understand what the client is really trying to accomplish. What are their goals? How important is this to them? What obstacles might get in the way of that vision?

Once we get clarity on those pieces, then we can determine whether we have the right solution to help them get where they want to go.

JAY:  When we spoke recently, Michael Junior, I wrote down a phrase you used when describing the optimal outcome you want for a client. You said, “We want our clients to have a solution that is impactful and affordable.” I found this succinct and insightful. Talk about that some more and give me an example.

MICHAEL JUNIOR: When we look at any benefit package, the work really comes in three phases: designing the plan, funding and financing it, and then the ongoing implementation and administration. What we've found is that if the design isn't truly impactful to the participants and the organization, the other two phases don't matter. That's why we put so much emphasis on getting the design right first.

In practice, that means we try to spend more time on the why behind a plan than the how. What are the owner's goals? What matters to their top people? Those two things have to be aligned, or the plan won't work the way anyone intended. You can design something that looks great on paper like a big contribution with a solid structure, but if it doesn't connect with what a key executive actually cares about at this stage of their life, it's just noise to them.

A good example is vesting. Business owners almost always push back initially on shorter vesting schedules. It makes sense, they want the retention hook to last. But take a 35-year-old rock star and design a SERP that vests at 65, and ask yourself honestly: is that really going to keep them around? Retirement is a lifetime away. That person is thinking about college tuition, their kids, their mortgage, not what life looks like in 30 years. So, we spend as much time as it takes walking ownership through those details, because what they build has to be impactful for the whole team, not just the owner's vision of what impactful means.

Once the design is solid, the financing conversation becomes a lot more fluid because now we know the why. When we get to what we call the hedging asset, we let the client drive that decision. Some prefer taxable securities. Others, once we walk them through it, find their way into the institutional world of COLI and the tax efficiencies that come with it. The majority of our clients do end up there, and the way we tend to frame it is pretty simple: here's a way for you, as the business owner, to use your corporate checkbook to fund executive retirement plans with no limits on contributions, growth that's tax-free, access that's tax-free, and full cost recovery that's tax-free. For most clients, that's a hard conversation to walk away from.

JAY:   I shared with you that when I entered the life insurance business, I implemented executive benefit solutions as a member of an M Financial Group firm.  When dealing with a closely held business consisting of family members, it seemed to me that there was always some friction between those family members that needed to be addressed before planning could start. Do you find that to be the case and how do you address these issues?

MICHAEL: Absolutely, Jay. Most closely held family businesses tend to wrestle with a similar set of issues. You tend to witness business‑transition challenges, management‑succession questions, acquisition decisions, executive‑compensation and retention concerns, family conflict, and overall risk‑management gaps.  So, yes, we run into this all the time.

A common example is when the father is the owner, and the son is assumed to be the heir apparent… but the team doesn’t respect him, he’s not the right fit, and everyone quietly knows the non‑family key executive is the real leader. That’s a tough conversation to have with an owner, but it’s necessary.

You must bring conviction, integrity, and a little toughness to those discussions. At the end of the day, you’re doing it for the good of the company and the family, even if the truth is uncomfortable.

JAY:  Speaking of family friction, it doesn’t appear that you have any in The Cowart Group.  In fact, you both have distinct skills that, when put together, really benefit your company.   Did I hear correctly that you can play good cop / bad cop with clients sometimes?

MICHAEL JUNIOR: Good cop bad cop might not be the best way to describe us to our clients! Michael Sr. has a few more cycles around the sun than I do, and with that he has seen and been a part of many different types of events in supporting our clients. I would say that Michael Sr. has a more emotional approach in our conversations with our clients.

I feel I have a more analytical approach in understanding the problem, versus the emotional touch that Michael Sr. brings to connect on a personal level. Maybe after another 25 years of working with clients, I will be able to communicate at the same level.

I tend to focus more on identifying the problem and the client’s goals, what are the roadblocks that are preventing the business or individual from achieving those goals, and how then working to provide a path get here.

JAY:  Michael, do you feel the same way as your son about the dynamics of your relationship?

MICHAEL: Absolutely!  We really are a lot alike in many ways, which makes working together natural. But what helps us even more is that we have different strengths. There are moments in meetings where we’ll both answer at the exact same time with the exact same response - that’s how in sync we are.

But we also balance each other out. Michael Jr. is more creative and more consultative in how he approaches planning. I’m a little more “touchy‑feely,” and I’m quick to pull out the bright, shiny solution - the vehicle where the money grows tax‑free, comes out tax‑free, and the company gets full cost recovery.

I think my son appreciates the experience and perspective I bring to the table, and I’m grateful for his people skills, his drive, and the advisory style he brings into every meeting. When you put those together, it really does create a good‑cop/bad‑cop dynamic when we need it, but in a way that serves the client and keeps the conversation productive.

JAY:  This may be in bad form for our readers, but I am going to share part of the answer you gave me, Michael, about one of your pastimes outside of work. You told me that you know it sounds cliché but that you really enjoy golfing. Then, you said one of your favorite things to do is to golf with your son. A collective “AWWW!” could be heard around Life Insurance Strategies Group when I shared your response.   I believe that was the first “mic drop” moment in the history of the Tier One Interview Series!

In addition to golfing with your son, what other interests do you have away from the office, Michael. The same question to you, too, Michael Junior.

MICHAEL: I love to run. It just makes me happy. Endorphins are real and when you finish a run, you feel like a different person. But for me, it’s more than exercise. It’s thinking time. On a run, I can practice a presentation out loud, work through a problem I’m facing, rehearse a speech, listen to a podcast about something I’m trying to improve, or just let my mind wander. Sometimes I pray. Sometimes I dream. And sometimes I’m just out there rocking to the Rolling Stones or Led Zeppelin.

I also really enjoy quiet time, especially early in the morning when everything is still. No noise, no distractions. There’s something special about sitting in an empty church when no one else is around - it’s peaceful in a way that’s hard to describe.

And of course, I love the beach. White sand, beautiful water, a chance to relax and a couple of ice‑cold beers doesn’t hurt either. But above all, I love spending time with my family and my four granddaughters. That’s the good stuff.

MICHAEL JUNIOR: We do share a lot of the same hobbies, especially growing up playing sports. And as you mentioned, Jay, we both love golf. It checks a lot of boxes at once; competition, exercise, mental toughness, and just being outside regardless of the conditions. But honestly, some of my favorite rounds are the ones with Michael Sr. There's something about being out there together. Unfortunately, the work conversation does not take a break, so we typically get some of our best work done on the golf course. I'll let him tell you who wins more often!

Running and walking are also a part of my routine, something I try to do daily. It's as good for my head as it is anything else.

We're also fortunate to live on the Gulf Coast in south Alabama, which means there's no shortage of ways to get outside. I've always loved being on the water, the beach, the boat, it doesn't matter. And now with my wife and three daughters, those are the moments I look forward to most. On any given weekend you can probably find me on the water, on the golf course, or somewhere in between with my family

JAY:  This has been such a treat!  Thank you for doing this.   We have reached our famous restaurant question. I want to hear from both of you.  Without naming a steakhouse or a steak dish, recommend some restaurants I need to visit and tell me what I should order when I do.

MICHAEL JUNIOR: My wife is going to be very disappointed I am not going to name some type of Japanese or Asian cuisine.  She is definitely the foody of the household and favors those restaurants.

My advice is to check out Clancy’s Restaurant in Uptown New Orleans. The best approach is to order several appetizers for the table: fried oysters with brie, deviled eggs, crawfish beignets, and honesty anything else you cannot go wrong. For the entree, it is hard to go wrong with the fried softshell crab.

MICHAEL: My wife, Cissy, is an outstanding cook. She’s from New Orleans and can whip up some of the best Louisiana cuisine you’ll ever taste, so most restaurants tend to be a little underwhelming for me.

But if I had to pick a favorite, it would be Glenwood Yacht Club in Mobile. It has an incredible vibe and energy, and the trout meunière is as good as it gets.