In this insightful interview, Bill and Amy Betts share how they transitioned from life on a sailboat to building a successful Medicare business in Southwest Florida.
After over a decade in the industry, they decided it was time to retire—but not without ensuring their clients would continue to be well taken care of.
Bill and Amy talk candidly about the emotions involved in leaving their clients, how they chose the right partner to take over, and why they resisted staying part-time.
If you’re an agent considering retirement, this story shows how you can feel confident passing your business on to a team that values your clients as much as you do.
Transcript:
Bill: We are Bill and Amy, and we're sailors. Our life’s ambition was to go sailing. In about 2007, we sold everything we owned—we sold the house, we sold everything in the house. In fact, we had a closet in Amy’s dad’s home that he let us have for storage, so we compressed our entire lives into one closet. Then we moved onto our sailboat and sailed literally around the globe. It took us seven years to do it, and it was an amazing adventure. I cannot tell you what a life experience it was.
When we returned, Amy’s stepmother had been selling Medicare Advantage plans. In Southwest Florida, a Medicare Advantage plan is a ton of health insurance at zero cost. As a salesman, when you tell me, “Okay, I want you to sell this product, it pays a pretty good commission. What does the product cost the consumer? Nothing.” That’s hard to believe, right? But it’s the truth. It sounds like a pretty easy sale, doesn’t it?
John: Absolutely.
Bill: And in our experience, if we get in front of a prospect, we close over 90%. So, it has been a wonderful sale, and it’s been a wonderful career for about 11 years now as Medicare specialists in Southwest Florida, which is frankly a target-rich environment.
John: How old were you when you ended your sailing adventure?
Amy: I had my 50th birthday in the middle of the Atlantic. So, that means he was 58 when we got back. We were about 50 and 58 when we got back to Florida.
John: So, you came back to Florida, and you were looking for careers?
Bill: Yes. I’d been in radio broadcasting for 35 years before we left. Amy’s a mechanical engineer. I’ve got to brag about Amy. She developed part of the fuel delivery system for the Space Shuttle. She also invented the thing that makes a Ranger bass boat metal flake, which is the even sparkle you see on those boats. So, when we came back to Florida, we were looking for jobs, but there wasn’t much opportunity for a mechanical engineer or a radio guy in our town. That’s when Amy’s stepmother introduced us to Medicare Advantage.
Amy: We didn’t know where it was going to go, but we thought, for about $1,500, we can find out. It’s not the hardest business to get into, so we did the training and licensing and started looking for jobs.
John: So, you got into the senior market, focused on Medicare Advantage, and did that for about 10 or 11 years. What brought you to the point where you’re thinking about getting out now?
Bill: Tomorrow is promised to no man. We got into the business when everyone we worked with was 65. Ten years later, they’re 75, and it’s pretty dramatic watching people age. Now I’m 69, and I look at myself, too. As you watch others age, you also see people pass away. That becomes heavy on someone who’s 69, and Amy’s young at 60, but it’s heavy on her too. So, we thought, during these years between 65 and 75, you’re still active, you can do whatever you want to do. You can travel anywhere, you can do anything. The tether between you and a physician is long and loose. But in five years, we don’t know that it will be.
That was the number one thing—watching our clients age and knowing we were aging with them. The second thing is, the older you get and the more experience you have in a business, the less tolerance you have for discrepancies, for things that don’t go exactly as you think they should. You become frustrated with some of those changes, and I found myself asking, “Why does it have to be this way?”
But I’m 69, Amy is 60, and our portfolio is where we need it to be. So, number one: tomorrow is promised to no man. Number two: we’re resisting the temptation to stay in it. Because in Southwest Florida, a target-rich environment, the commissions keep going up and up. It’s tempting to hang on, but we’ve drawn a line in the sand. We are done.
John: It’s hard to quit when the fishing is good, isn’t it?
Bill: Exactly. We go to the grocery store, and we see our clients. We drive to the grocery store, and we pass by three or four clients’ homes. We’re in a very targeted community. And as I said, it’s a target-rich environment for a Medicare salesperson. So, we’ve really grown in the community, and we’ve enjoyed it. But we’re resisting the urge to hang on.
Even you, John, have said to me, “Well, you can keep your license and work part-time. You can take the ducks as they come in.” But no, we’ve drawn that line in the sand, and we’re done.
John: How was the process of leaving the business?
Bill: It was easy working with you, but it was less easy working with insurance companies and prior uplines as we began to leave. I was surprised to learn that I needed a separation agreement from my prior upline. I’ve always considered myself an independent businessman. We take the risk ourselves, we absorb the expenses, we are independent. But then, as we separate from our prior upline, we needed what amounted to permission.
That phone call got testy. We have a great relationship with our prior upline, but that conversation was tough, and we didn’t end on the best terms. Since then, we’ve both apologized, and we’re still good friends, but it was a surprising experience.
John: How has it been working with us?
Bill: It’s been great. You’ve always been accessible. When I call, if you don’t answer, I get a text saying, “In a meeting. Can I call you in 23 minutes?” And at 23 minutes and a second, you call. You’re a great businessman in that respect, and your whole staff has been fantastic.
Broderick, who’s taking over our list, has been the consummate professional. I send him an email with a question, and I get a quick response. If one of our clients calls me, I send the details to Broderick, and he handles it right away. That level of professionalism has made this process much smoother.
John: Part of that is because you and Amy really care about your clients, right?
Bill: Exactly. We’re morally good people. As we sell our book of business, we’re not selling out our friends. We’re talking about 1,200 people who are Medicare eligible, who work with us every day, or who have worked with us in the past. We don’t just want to drop them off in someone’s lap and say, “Good luck with that guy, hope he’s a good one.” We care about these people, and we want them to be taken care of.
I tell everyone who contacts me: “We haven’t sold you off to a call center. Joe Namath's cronies aren’t going to be calling you up and trying to push something on you.” The people who are taking over know you, they have your file, and they’re not just a faceless phone room. I think our clients take comfort in that. They know we truly care about them, and we’ve handed them to someone else who truly cares about them.
Amy: Yes, you only have a few options. You can either continue working, or you can ghost your clients, which is just not answering the phone once you retire. I can’t do that. I won’t ghost my clients—because that’s rude, just to the bottom of my heart, that’s rude. So, the last option is to sell your book of business to someone who’s going to at least care about it as much as you do. And that’s what we did.
Interviewer: What’s next for you both?
Bill: Well, we have way more guitars than we know how to play, and we have a garage full of bicycles. There are entire parts of this continent that we haven’t explored yet, and we intend to explore them on our bikes.
Interviewer: Thank you both for sharing your story. I really appreciate it, and I’m sure other agents will find inspiration in your journey.
Other interviews in this series:
- Sell Your Medicare Book and Keep Selling: with John Knepper
- Selling Your Medicare Book of Business: An Interview with Debbie Deane
-
Selling Your Medicare Book of Business: An Interview with Steve Cooke
Conclusion
Bill and Amy’s experience shows that transitioning out of the Medicare business can be done with integrity and confidence, ensuring your clients remain in trusted hands.
If you’re considering retirement and want to learn more about how to sell your book of business while maintaining peace of mind, schedule a discovery call with us today.
