Sprinkle Kindness and Play the Long Game: One Founder’s Three-Transition Journey

What happens when you realize that 100% ownership of your company might actually be worth less than a small stake in something much bigger?

Mark Richards spent more than four decades building a career in advanced planning and life insurance for ultra-high-net-worth families. Along the way, he went through three major transitions: launching his own firm, merging into the Madison Group, buying out the founder during a financial crisis, and eventually rolling his equity into Winged Keel Group, which has since become the leading distributor of private placement life insurance in the country.

Mark’s story touches on almost every challenge business owners face when thinking about what’s next. A compensation model with zero recurring revenue. A founder who overvalued the business for years. A credit line that got converted into a loan with no capital access. And an advisory board of volunteers who told him, respectfully, that he was running out of runway.

But what makes this story worth hearing isn’t just the obstacles. It’s the decisions Mark made along the way. He built a volunteer Wisdom Council of five people who met quarterly and held him accountable. He brought his daughter Lily into the business through a structured training program. He joint-ventured with Winged Keel for 20 years before merging with them, building trust one deal at a time. And when it came time to approach the CEO about a merger, the opening came over dinner in New York from a relationship that started with buying two strangers lunch in Hanoi decades earlier.

The result? His small ownership stake in Winged Keel is now 470 times what his full ownership in the Madison Group was worth.

In this episode, you’ll learn:

• How Mark navigated three transitions across a 45-year career and what each one taught him

• Why a business model with no recurring revenue creates a valuation challenge that many owners don’t see coming

• What happened when a founder’s emotional attachment to valuation collided with a financial crisis

• How a volunteer advisory board (the “Wisdom Council”) changed the trajectory of Mark’s business and his transition

• Why Mark brought his daughter into the business through a training program instead of handing her a role

• How 20 years of joint ventures and one act of kindness in Vietnam led to the partnership that changed everything

Chapters in this episode:

01:00 — Welcome and Meet Mark Richards
02:27 — What Winged Keel Group Does and Why It’s Different
04:10 — How Mark Got Into the Industry (and Why He Stayed)
06:34 — The Madison Group: How It Started
07:08 — Three Transitions in One Career
09:00 — The Business Model Challenge: No Recurring Revenue
11:14 — The Founder Problem: Greatest Asset, Greatest Liability
12:39 — The Crisis: When the Bank Converts Your Credit Line
13:40 — Never Waste a Crisis: Buying Out the Founder
15:06 — What the Buyout Taught Mark About Transitions
16:08 — Building the Wisdom Council: A Volunteer Advisory Board
20:29 — “You’re Running Out of Runway”: The Board’s Honest Feedback
21:00 — The Winged Keel Connection: 20 Years of Joint Ventures
22:30 — Lunch in Hanoi: How a Small Act of Kindness Planted a Seed
23:10 — Dinner in New York: The Conversation That Started the Merger
24:08 — The GTCR Investment and What It Meant for the Platform
26:01 — How Private Placement Life Insurance Solved the Business Model
27:27 — Where Winged Keel Is Headed
30:45 — Mark’s Advice: Sprinkle Kindness and Play the Long Game
32:00 — 470x: The Math That Proves the Philosophy

Connect with Mark Richards:
LinkedIn: Mark Richards | LinkedIn
Website: https://www.wingedkeel.com/

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Sprinkle Kindness and Play the Long Game: One Founder’s Three-Transition Journey Transcript

Elizabeth Ledoux:
Hello everyone and welcome back to the Business Transition Roadmap. I’m Elizabeth Ledoux and today I am so excited to be joined by Mark Richards. He is a principal with Winged Keel Group and he’s the leader of their Denver office. He and his team, they are so sophisticated and they focus on life insurance based solutions for ultra high net worth families, family owned businesses and also

privately held companies. Mark and I have known each other for quite some time through a couple of different connections. And I’ve just appreciated him for many, many years. He’s got more than three decades in this advanced planning world and nearly 40 years with what was his company called the Madison Group. So today he’s here to talk to us about his experience.

⁓ with the Madison group, how he built and grew that, and then how he went through a transition that, in my opinion and from my perspective, has been so successful. So today what I want to do is help us all to gain some wisdom from Mark. So Mark, welcome, and I’m so happy you’re here.

Mark Richards:
Thank you, Elizabeth. Yeah, my hope is that I can share something that someone else can use and find valuable.

Elizabeth Ledoux:
That’s great. Well, thanks. So Mark, ⁓ how about, why don’t we start with you just telling us a little bit about ⁓ Winged Keel. And then I’d like to, once you do that, we’ll go into your journey from the Madison Group over to where you are today.

Mark Richards:
Thanks, Elizabeth. Yeah, Wing Keel is ⁓ unusual in that ⁓ we are the first national multi-generational ⁓ life insurance distribution platform that serves the ultra high net worth marketplace. ⁓ And that description might

⁓ not have a lot of sizzle to it. So we are the leading distributor of life insurance ⁓ among every one of the life insurance carriers distributing private placement life insurance. And we are ⁓ the largest firm within a already elite national distribution platform called ⁓ Financial, which is a

broker dealer and distribution firm. And perhaps we’re in 17 markets now. ⁓ And perhaps most importantly, we’re just getting started. Over the next five years, I would be surprised if our employee count or revenues, ⁓ every metric hasn’t doubled.

Elizabeth Ledoux:
That is so exciting. Let’s go back into how did you get started here? You’ve got this incredible company that is running well and has some incredible potential in front of it. Let’s go back. How did you get here? What’s this journey look like for you?

Mark Richards:
Well, you were kind in your dating of me, your carbon dating of me. I actually began in 1980 in this field and had left a position on Wall Street coming out to Denver to ski. It goes 25.

⁓ At that time, I hired on with a firm that said they were doing financial planning and it wasn’t until later that I learned that that was code for life insurance. And then by that time, I had given up my position in New York. I was committed to living in Colorado and I said, well, I’ll give it a try, but I didn’t like the idea of life insurance. so I really focused on the financial planning part. The evidence of that is the…

five or six designations I now carry. But I recognized in doing what I was doing over time that while all the planning was valuable, ⁓ most of what you do in planning is subject to all the real life happenings and ends up being somewhat ⁓ misguided.

because you’re thinking linear and life happens in a random sequence. ⁓ but what remained as very valuable to our clients was the insurance that we placed. So as time went by, I began to narrow my focus and ⁓ upgrade the market focus to the ultra high net worth, which today we define as a hundred million and above.

And we have at Winged-Keel over 750 centimillionaire clients and over 350 billionaire clients. I just saw recently that there’s 3,500 billionaires in the United States, so have 10 % of that.

Elizabeth Ledoux:
Wow, wow, that’s incredible. when you tell me a little bit about the Madison group and how you started, how that came about, and then, and you know, you did make a transition. So I want our audience to know about that transition, how you got in, how you merged in what happened with Winged Keele, and also talk a little bit about your family. So let’s start with this journey. How did you?

what were you doing when you started thinking about transitioning?

Mark Richards:
Yeah, I’ve had three transitions in my career, which literally over that period of time is not so many.

But the first was moving from the firm I hired on with into my own independent firm, the MJ Richards Company. The second was merging the MJ Richards Company into the Madison Group. And the third was Madison Group into Wayne Keele. And actually, there’s probably a fourth, which was me becoming the sole owner of the Madison Group. So when I joined the Madison Group, ⁓ I was… ⁓

recruited by the founder and it made sense to me because I was spending a lot of time on the business side instead of the client facing work and I wanted to focus more of my time on the client facing work. So that was the promise when I joined the Madison Group. In our business, as in many businesses like this where you have individuals responsible for generating revenue,

If you are successful in that job, then you automatically kind of get ⁓ put into a position of management and ownership over time because of the value you represent to the firm. And that doesn’t mean you’re good at either management or ownership. It just means that that’s what happens. And in my case, I don’t think I was particularly good at either one of those.

And I don’t think I was particularly interested in either one of those. really wanted to focus on the client work. I had lots of ideas about the business, but I wanted somebody else to execute. when we got to when we got to win keel, that was critical. and now I’m where I want to be. But that took, you know, 45 years. So the big issue at the Madison Group was that we had a we had a business model challenge and we had a founder problem.

and then we had a crisis. So the business model challenge was that our business, life insurance, in the traditional side, and I’ll differentiate that between the non-traditional side ⁓ as we go through this, but the traditional side has a compensation model that’s been around for a long time, designed by the insurance companies, which is to pay a heaped commission upfront and really nothing thereafter.

There’s some trails on some products, but if you say it’s nothing thereafter, you’re more accurate ⁓ in making that comment. ⁓ So that’s the business model challenge, right? Because you have service requirements. If somebody buys an insurance policy from you, they expect to be able to call you up and ask for ⁓ something to be done and have it done. And they expect you to report on how that policy is performing and inform them if there’s a change that’s needed, et cetera.

And that requires staffing, of course, it requires ⁓ training and systems. And so ⁓ it’s difficult when your revenues don’t match your liabilities. You have this long tail. It could be 50, 60 years, a lifetime of the insured with no revenue. And you can’t do repeat business with clients if you’re not providing service.

meeting commitments, you know, and making it a good experience when they acquire the insurance. you do the servicing, but you have to then generate enough revenue from new policy sales to be able to afford the staff and all of that. So that’s the business model challenge. And also part of that business model challenge is what is the value of a business where all the revenues have to be renewed every year, there’s nothing recurring, and you have a big tail of liability on the service side.

So, you I would argue that that model has a zero enterprise value or even a negative enterprise value. And so that’s a big challenge. And then there was a founder problem. The founder was a gentleman who was, you know, obviously we’re all aging. He had been a very successful agent with a lot of, at the time, innovations that he brought to the Madison Group.

Elizabeth Ledoux:
That’s a big challenge.

Mark Richards:
The group was nationally recognized as one of the preeminent providers of life insurance to the ultra high net worth marketplace. But the medicine group focused really only on the traditional marketplace. So it had all those issues I talked about. And the founder had as many founders, had a, ⁓ as I used to say, he was our greatest asset and our greatest liability. ⁓ So ⁓

Personality wise, it was difficult ⁓ to ⁓ attract and retain the key people and ⁓ his production, his ability to ⁓ generate revenues ⁓ was declining. He was on a pretty steep decline. ⁓ And ⁓ so that was causing firm revenues as mine were growing to be ⁓ either static or declining overall.

And so this reality was beginning to dawn on everyone but the founder. And so it took years before we got into a crisis mode. And the crisis mode was that we were no longer making enough money to pay down our credit line. And the bank turned that credit ⁓ into a loan to be amortized. So we had no access to capital. ⁓

Elizabeth Ledoux:
Hmm.

Ouch.

Mark Richards:
And so at that point the founder so there’s a saying it goes something like never waste a crisis at that point the founder ⁓ Wanted it up till then one of the issues in planning succession and I was an owner in the business but he had a His focus his motivation was you know the markets they say are driven by greed and fear He was in a greed mode. He felt that the value of the firm ⁓

was much greater than any financial justification would give it. ⁓ But now he went from greed mode to fear mode because of the liabilities. And once he went into fear mode, it was much easier to get to a reasonable valuation. And I was actually on my way out at that time. I was creating my own firm. ⁓ But that, you know, it accentuated the fear because he knew he couldn’t keep the firm afloat without me.

Elizabeth Ledoux:
Mm.

Mark Richards:
And our COO brought that reality to his attention and said, Mark is the firm. He’s 95 % of the revenue. you know, without him, there is no firm. So my attorney who was helping me set up a new company said, let’s just make a proposal. And I said, well, it’s going to, I don’t want to do that because we’ll spend a lot of time on it. And at the last minute, he’ll change all the terms of the deal, which I’d been the MO. And, ⁓ but this, said, we’re not going to negotiate.

just make a proposal. And by this time he had an attorney and his attorney was able to point to him and say, look, in order to negotiate, you have to have something to negotiate with. You don’t, you you either take this or leave it, but I would recommend you take it. And he did. And so we were able to, and it was a fair deal. And it actually turned out to be very profitable for him, but it was based on, wasn’t making any commitments. didn’t make sense at the time. It was giving him a participation.

Elizabeth Ledoux:
Good.

Mark Richards:
in the future, ⁓ which turned out to be extremely profitable. ⁓

Elizabeth Ledoux:
Good for him and good for you. You know, it’s interesting. Thanks for sharing that story. And then the next thing I want to do is go through your next one and your daughter’s included in that. So I want to make sure that we put in that family piece as well. isn’t, I would say, isn’t it interesting? Because one of the big things that I talk about is trying not to make, you know, if you have a strategy, you work together, you don’t get at.

you know, opposed with maybe an employee or a person, a partner, another partner wanting to leave. And that it doesn’t become just an event because you wandering all the way up to that time, I’m sure there was a lot of struggle and a lot of challenge even relationally between the two of you because you’d probably worked well together in prior times and all of sudden now we’re not. And ⁓ yeah, pretty tough time.

Mark Richards:
It wasn’t something I want to repeat, ⁓ but it was all necessary to ⁓ get to the blue skies we have today. ⁓ I had about a five-year period of ownership, of sole ownership in the company. One of the first things I did was to ⁓ recruit an advisory board, and this was five people who agreed to serve on a board basis.

Elizabeth Ledoux:
down.

Mark Richards:
⁓ although not a formal board. And ⁓ we called it the Wisdom Council. It was comprised of a retired trust in the state attorney who had been the leading trust in the state attorney in the ultra high net worth marketplace, the previous head of JP Morgan Private Bank. And it was ⁓ also joined by my COO and a woman who was ⁓

kind of the mover and shaker at our broker dealer and distribution platform, M Financial Group. So she was probably the most important person there and she was on the board. And then we had a fifth, which was a client who we had worked with, who represented kind of the perspective of a client, what was important from that perspective. He was also a very good businessman. He turned out to be an incredibly helpful board member.

Those five, which was a board that worked in a total volunteer basis, I would say to your listeners, Elizabeth, don’t assume that you don’t have friends who will do this just out of the goodness of their heart and because they believe in business and succession and especially with retired folks who had high-powered jobs, many of them just want to have a hand in it. They just want to…

be involved and use some of the experience that they’ve had. They don’t need the money. ⁓ It was an incredible board and we met quarterly and we reported to them quarterly. gave them full transparency on our financials. We had initiatives that we would report on every quarter. And one quarter, about three and a half years into this, by this time I had hired Lily. So Lily is my daughter and Lily, ⁓

still lives in West Hollywood. She went to school at Emerson and ⁓ graduated with an education based on ⁓ writing ⁓ for screenplays and acting. ⁓ it turns out, and David Brooks points it out in his book, How to Know a Person, that that is actually a very good background for ⁓ sales.

I did not know that at the time. was looking at it as my daughter is ultimately going to have a problem in her income. And so I wanted to ⁓ give her an opportunity to have a dual track in her career. And so I asked if she was interested. ⁓ We had a training program sponsored by Financial at the time. And so I asked if she wanted to join the training program and learn how to be a CRM or a Client Relationship Manager.

⁓ She jumped on the chance which surprised me. I thought she was just so into the entertainment business that she would say no This is my passion to keep doing this but she she didn’t she said I would love that and ⁓ And then she was a star in what they called a magna star program. It was a training program was called magna star and I’m sorry. It was called magnet magnet and she was a star

in that program. They tapped her as one of the people who had the most potential. And then when, you know, not to get too out of sync here, but when Winged Keel, when we merged there, they looked at every employee and hired them independently, but they also tapped Lily as someone with a great deal of potential. anyway, back to the advisory board. About three and a half years in, the advisory board said, Mark, we appreciate that you’re trying to create

your succession organically. had not only Lily but I one other CRM writer, both women, and ⁓ they said, but we think you’re running out of runway, which was a kind way of saying you’re getting old, and we want to come back with a plan B. So one of the things when you ⁓ have a volunteer board and they are providing you great counsel, your responsibility

Elizabeth Ledoux:
Aww.

Mark Richards:
is to do whatever they ask, right? I mean, you’re not going to

Elizabeth Ledoux:
Absolutely to listen, to listen

and act. Yeah.

Mark Richards:
So at the time, was obvious, everybody in Financial knew that the most successful firm within Financial was Winged Keel, headquartered in New York. And ⁓ I had ⁓ worked with Winged Keel over the past 20 years. Whenever I had a private placement life insurance policy ⁓ scenario, I would joint venture with them.

because they were the experts in that area and they were the pioneers in that area. So we had a few mutual clients and we had experience in working together and so we had trust and we had knowledge of one another. And also this turns out the CEO of Winged Keel at that time managing partner but now CEO. I had met on a, ⁓ used to do this thing called a sabbatical cruise.

and we’re in Vietnam on a stopover and ⁓ Petra ⁓ had picked out a lunch spot, probably the most expensive restaurant in all of Hanoi. It was a kind of a diplomat ⁓ setting, very much like Rick’s Cafe and the ceiling fans and the palms and ⁓ the white coated waiters.

very different than everything else in Hanoi. So anyway, I’m having lunch and the bill comes and it’s like New York City pricing. And I’m like, my gosh, now look over, these two young guys who are on the ship and I didn’t know them very well, but I saw that they were dining here and I thought, my God, there’s no way they’re gonna be able to pay their lunch bill. So I told the waiter I wanted to pick up their tab. So I bought their lunch, they came over and thanked us and that was…

just a little sprinkling of kindness. ⁓ then 20, 30 years later, that turns into when I talked to the, I called the CEO and I said, Hey, Eric, I’m going to be ⁓ back East. And I wondering if you had time for a dinner. And so we had dinner in New York and I was, I was struggling with how I was going to broach this subject. And

Elizabeth Ledoux:
Sure.

Mark Richards:
We ⁓ were just about 20 minutes into dinner and ⁓ I said, so you’ve been really expanding your platform. And he’s quite happy about it. He says, yeah, we have Boston and we have, at that time they didn’t have Atlanta, but we have Richmond, we have Dallas, we have San Francisco. And ⁓ I said, yeah. And it just kind of came to me as we were talking. I said, that’s why you need something in the middle.

And he said, I couldn’t agree more. That’s what I was hoping dinner would be about. So we had an immediate good start and then we agreed to sign NDA and we just kind of proceeded from there, which went without a hiccup into ⁓ a sale to Winged Keel where I rolled my equity ⁓ in Madison Group into Winged Keel. And then it wasn’t

Elizabeth Ledoux:
⁓ Isn’t that fantastic?

Mark Richards:
for it was only two years later that Winged Keel successfully ⁓ attracted a large investment from a prestigious private equity group called GTCR. And they really were interested. They had in the past, ⁓ they were a financial and technology focused, financial technology focused private equity group.

And they were interested in finding a way to ⁓ invest in a pure life insurance play. And ⁓ especially in the ultra high net worth marketplace, because we’ve all heard the terminology of a K economy that has been, you know, I’ve always been in that space, but that space seems to be the ⁓ most attractive space today. so. ⁓

That put a value on Winged Keel and also took care of a founder problem that Wayne Keel had. So we were able to accomplish both of those with that investment and also gave us great insight and ⁓ ability to have synergistic partnerships ⁓ that expanded beyond Wayne Keel’s relationships and connections. So they’ve been a great partner.

Elizabeth Ledoux:
Nice.

That is.

Mark Richards:
You know, the board meetings with GTCR and the direction they give us has been phenomenal. We doubled our EBITDA in the trailing 12 months following that investment. So they’re very happy with us. We were the highest, I think we still are, highest performing asset in their portfolio. Although I think we’re also the smallest. And back to the formula, the challenge.

Elizabeth Ledoux:
now.

Mark Richards:
of the business model. Winged Keel had solved that 20 years before, and it took that kind of a time frame by ⁓ pioneering into the private placement life insurance. And that had a different kind of compensation system. It did not have any commission embedded in the placement of a policy. It had a placement fee that we structured, and it had an ⁓ asset ⁓ administration fee.

And so based upon the cash values, the investment growth of the portfolios, and so very much like an AUM model. that’s recurring revenue, and that has value both for Wall Street and also it provides the ability for a firm to make investments because we know we have X dollars coming in over the next 12 months. So we’ve been able to really double down on our infrastructure.

Elizabeth Ledoux:
Yeah.

Mark Richards:
and all the things that really differentiate us. have professional management. ⁓ You know, we were able to think beyond tomorrow and really focus on the future and where we want to be. And so it’s for me, having started in this business so long ago and over time, recognizing what the business challenges were to be on the side of the fence where we solve those.

Elizabeth Ledoux:
Hmm?

Mark Richards:
and we’re just distancing ourselves from all our competition is very gratifying at this stage of my career. It feels very fortunate.

Elizabeth Ledoux:
I am so excited for you. And just to pull on, you said so many things. I’m just going to try to pull on a few of those. ⁓ the concept of one, understanding your business model, two, navigating. you have put a lot of thought in, and I’ve noticed that about you. You always do put a lot of thought into ⁓ taking care of others, understanding what the risks are.

identifying paths forward that make sense. ⁓ Again, that board bringing that on and, you know, not just listening, but also acting and valuing outside input. ⁓ So many entrepreneurial people play the Lone Ranger game. When I see them sometimes, they’re just, you know, they they’re playing the Lone Ranger and ⁓ really utilizing the assets and the people and the friends that you have around you.

to help to navigate a great business and also a great life. In The Transition Strategists, which is our company, the focus for me, and this is just my life focus anyway, is for people to live their best lives. ⁓ Great decisions help to do that. You really have pulled this all together and created a great outcome for you, employees, clients, and your daughter as well.

Mark Richards:
you.

And thank you for saying that Elizabeth. And I would say looking back, know, a lot of it is values based, right? I’ve been complimented by people from all angles of the business in my ⁓ differentiation from everybody else they’ve worked with in that I’ve never valued a single transaction. A lot of folks in our business

will work on a large transaction, maybe the largest they’ve ever done, and they will try to maximize the compensation and use that as a way to create financial freedom. I’ve always ⁓ made sure that whatever we were doing, it was the client first. And as a result, for instance, ⁓ in the private placement space, I recognized that I didn’t know what I didn’t know. And rather than try to ⁓

keep all the revenue at the Madison Group, from every one of them I ever did, I joint ventured with Dwing Keele. And ⁓ that was because I knew that they had the expertise, I knew that the client would be better served if I brought them in, and I knew that they were willing to come in as a partner on a 50-50 basis. So that turned out to be just a client-centered approach that ultimately had a big impact

on the ability to ⁓ create this succession and now have a platform, be part of a platform that is ⁓ leading the industry into the future.

Elizabeth Ledoux:
It’s incredible. So ⁓ as we, this has been great. The time always goes so fast and I’m very grateful for you to have shared so much with us today. ⁓ What things, Mark, ⁓ as our audience walks through their transitions and they walk through thinking about them, strategizing around them, planning for them.

What things would you recommend they keep in mind?

Mark Richards:
⁓ I’m not sure this is a great answer ⁓ to your question, but I would certainly say, know, sprinkle kindness, you know, make sure that your competition doesn’t preclude friendship because that might be, you know, who you actually end up, you know, being partners with. And and I and I would say that don’t focus on having, you know, a large

percentage of either a transaction or a business, my small ownership in Winged Keel, and I did this calculation just before I call Elizabeth, is now 470 times what my 100 % ownership in the Madison Group was.

Elizabeth Ledoux:
Wow, that’s incredible. Wow, that, you know what, that’s incredible. ⁓ Those are incredible numbers ⁓ and also great wisdom because sometimes I think we do get too focused on the dollars and not as focused on the outcome and the people side. I think the people side, the value side is so important in this. Wow. Congratulations, Mark. I’m so excited for you. Yeah, live in your best life.

Mark Richards:
Thank you, Christian. Happy Memorial Day.

Elizabeth Ledoux:
Mark, thank you so much for being on the show today. I so appreciate you and know that this wisdom that you have and also that what you’ve shared with us will give people an idea of what a journey can look like and what a successful journey can look like because we’ve got one right here. So many times we hear the ones that don’t work. Well, this is a great example of one that was absolutely you hit it out of the park, Mark.

Anyway, thanks again for being here.

Mark Richards:
Bye, Lizarder.

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