Navigating Medicare: Expert Tips and Strategies | Dan Pascone with Tom Caress | Podcast #02

Medicare is complex, emotional, and extremely personal so Tom Caress built an agency that makes it simple and human again. In this episode, Dan talks with Tom Caress, founder and CEO of the Caress Insurance Agency, about how he helps people across the country navigate Medicare plans, costs, and coverage decisions. Tom explains how helping his own mother sparked his Medicare career, why he believes everyone needs a trusted advisor (not a 1-800 number), and how his 240+ agents partner with doctors, pharmacies, HR teams, and wealth managers to make sure seniors get the right plan, good access to care, and fewer financial surprises. They also discuss the coming wave of retirees, the shortage of Medicare agents, and practical advice for people approaching 65 or supporting aging parents.

• Tom’s origin story: it started with his mom.

  • About 18–19 years ago, Tom’s mother moved in with him. She was on a Medicare plan paying $400/month and only receiving $800/month from Social Security.
  • She didn’t know what she had only that Tom’s late father told her “don’t get off this plan.”
  • Tom got licensed with Aetna and UnitedHealthcare, reviewed her options, and moved her to a Medicare Advantage plan where she kept the same doctor, saved $400/month, and effectively doubled her income.
  • That “light bulb” moment seeing the impact on one person’s life convinced him there were many more people who needed help, and he shifted his focus fully to Medicare.


• Who Tom serves today. The Caress Insurance Agency primarily helps:

  • Individuals 65 and older who are:
    • Moving from employer coverage to Medicare
    • Leaving individual ACA or marketplace plans
    • Retiring and unsure how to transition
  
  
  • People who are already on Medicare but:
    • Don’t understand their current plan
    • Are unhappy with costs or access
    • Need to change plans during annual enrollment
  
  
  • He also runs a large agency with 242–243 agents across the country, helping them build careers in Medicare while serving their local communities.
  
  


• Education and “Medicare translation” are core to his process.

  • Most of Tom’s clients are very successful NFL coaches, legislators, judges, world-class musicians, business leaders but don’t understand Medicare because they’ve always been on group plans.
  • He breaks Medicare down into simple, understandable choices and lets the client decide.
  • He starts by asking: “What’s most important to you low monthly cost? Maximum doctor choice? Access to specialists? Simplicity?” and then tailors recommendations.
  • Tom refuses to just “pick a plan” for people; he believes the happiest clients are the ones who choose their own plan with proper guidance.


• Choosing between Medicare Advantage and Medicare Supplement.

  • Tom works with all major types of Medicare plans:
    • Medicare Advantage HMOs / PPOs / HMO-POS
    • Medicare Supplements (Medigap) plus standalone drug plans
  
  
  • Key factors he uses to guide people:
    • Whether they have adoctor they really like or need to find one
    • How important it is to go to any doctor nationwide without referrals
    • Their willingness to trade higher premiums for broader access vs. lower premiums and more managed care
    • Health status, prescription needs, and budget
  
  
  • He often sees couples where one spouse is on a Medicare Advantage plan and the other is on a supplement, because their needs and preferences differ.
  
  


• How clients find Tom & his agents.

  • Tom’s agency generates business through:
    • Direct mail flyers (especially to people turning 65)
    • Community presentations and educational events
    • Doctor offices and medical groups referring patients for help with Medicare
    • Pharmacies, dentists, optometrists, and other providers who see seniors struggling with coverage
    • Wealth management firms that want Medicare help for their clients
    • Radio and TV in select markets
  
  
  • Because Medicare marketing is highly regulated and they can’t cold-call seniors, direct mail and referrals are critical.
  
  


• Referral partners: where the synergy is.

  • Tom collaborates with:
    • Wealth managers and financial advisors he helps their clients with Medicare; they help his clients with investments, income planning, life insurance, and long-term care.
    • Property & casualty agencies especially former Farmers agents who needed new revenue streams.
    • Employers and HR teams helping 65+ employees transition off costly group plans to Medicare, often saving both the company and the employee money.
    • Counties and cities where his agents help public-sector employees shift to Medicare when eligible.
  
  
  • He emphasizes long-term relationships where everyone wins: the client, the advisor, and the agency.
  
  


• Scaling an agency to 240+ agents.

  • Tom started by recruiting Farmers Insurance agencies whose commissions were being cut, helping them add Medicare as a product line.
  • Today, over half of new agents come from insurance company referrals because carriers know Caress Insurance supports and trains its agents well.
  • Tom reinvests heavily in:
    • Marketing support (mailers, leads)
    • Systems and CRMs to manage books of business
    • Training and coaching so agents can build sustainable, residual-income careers
  
  
  • His philosophy: spend the upfront money on the agent; if they get in front of enough people monthly, everyone’s long-term residuals grow.
  
  


• Where the industry is headed.

  • Before COVID, there were more Medicare agents than there are today.
  • At the same time, the number of people becoming Medicare-eligible is projected to increase by nearly 300% over the next decade.
  • This mismatch means:
    • Access to good advice is becoming a bottleneck.
    • Agents must become more efficient, especially during Annual Enrollment (Oct 15–Dec 7).
    • Software, automation, e-apps, and CRM tools are critical to serve large client bases well.
  
  
  • Tom sees automation (e.g., online applications, survey tools, plan-change alerts) as the key to handling growth while maintaining service.
  
  


• Biggest personal challenges & lessons.

  • Biggest life challenge: family raising four children, now 16 grandchildren, and keeping everyone close despite “diverse views.”
  • He and his wife intentionally spend one-on-one time with each grandchild to mentor and support them.
  • Biggest early-career challenge: being drafted during the Vietnam era at 18 and suddenly made commander of 90 men his first experience in leadership.
  • Later, in corporate life with Toshiba, a consultant told him he was a micromanager and taught him to delegate by championing others’ ideas. That shift dramatically improved his leadership and business success.


• Lightning round themes.

  • Neither coffee nor tea (but leans dogs over cats).
  • Favorite non-phone tech: his golf cart he owns two, including a “Jaguar” cart.
  • Favorite saying: “Don’t fix the blame, fix the problem.”
  • Simple money rule: spend less than you make.
  • Bucket-list: playing Royal Dornoch in Scotland (his favorite course), and he’s played almost every top course except Augusta and Pine Valley.
  • Financial milestone: aims for a private jet.
  • Lesson learned: don’t buy stocks on leverage.
  • Advice to younger self: start saving earlier.


• How to connect. Tom gives out his direct number 760-413-9749 and email caressinsurance.comtom@gmail.com (as shared on the show), inviting calls or texts from:

  • Individuals needing Medicare help
  • Agents wanting to learn the business
  • Advisors looking for a Medicare partner

  Dan notes that Tom’s contact info will be in the show notes.

• 00:02 – Sponsor & opening. Tailored Wealth is introduced as the sponsor, helping business leaders live their version of a rich life. Dan welcomes listeners and restates the show’s mission: help people make smart, confident money decisions.
• 00:36 – Dan sets the stage. Dan reintroduces himself as founder and CEO of Tailored Wealth and frames the episode as a deep dive into Medicare solutions.
• 01:00 – Meet Tom Caress. Dan introduces Tom Caress, founder and CEO of the Caress Insurance Agency, noting that Tom and his team help people nationwide find effective Medicare solutions.
• 01:20–02:11 – How Tom got into Medicare (helping Mom).

  • Tom shares that his mother moved in with him 18–19 years ago after his father died.
  • She was paying $400/month for a plan she didn’t understand, while only receiving $800/month in Social Security.
  • He got licensed with Aetna and UnitedHealthcare, evaluated her plan, moved her to a Medicare Advantage plan with the same doctor, saved her $400/month, and effectively doubled her income.
  • He realized there must be many more people like her who needed help.


• 02:11–03:34 – Transition from corporate to Medicare specialist. Tom explains his background:

  • Worked in computers and ran parts of Fortune 100 companies in Europe (Toshiba, Samsung).
  • Sold to businesses and trained teams to work with big corporate clients.
  • Liked the idea of residual income (inspired by Warren Buffett), which drew him to insurance and eventually Medicare.
  • Being able to change individual lives and see tangible results felt more rewarding than big corporate deals.


• 03:34–04:24 – Finding purpose in helping individuals. Tom describes the emotional reward of helping people get better coverage and access—many clients hug him or cook for him because of the impact on their lives.


• 04:24–05:12 – Ideal clients & what he does for them. Dan asks about Tom’s ideal client; Tom explains most of his clients are:

  • Professionals (judges, legislators, musicians, NFL coaches, athletes, etc.)
  • Experts in their own field but unfamiliar with Medicare.
  • Tom helps them understand the basics, compare options, and choose plans that fit their priorities.


• 05:12–07:03 – Tom’s philosophy: educate, don’t dictate.

  • He walks clients through what’s most important: low-cost vs. maximum access vs. simplicity, etc.
  • He presents the pros/cons of Medicare Advantage vs. Medicare Supplement + drug plan.
  • He refuses to decide for them; instead, he explains until they can pick confidently themselves.
  • Couples often end up on different plan types because their health and preferences differ.


• 07:03–08:10 – The need for a primary doctor & proper guidance. Tom emphasizes the importance of having a primary doctor or clinic who can:

  • Help coordinate care and referrals
  • Advise on lifestyle changes (e.g., weight management) rather than jumping straight to specialists
  • Work within the plan’s structure to get patients what they need


• 08:10–09:18 – How clients typically find Tom.

  • They use direct mail extensively, especially for people turning 65 (the post office has even commented on their volume).
  • They host community meetings, 1:1 calls, and Zoom sessions.
  • They partner with doctor groups, pharmacies, dentists, and optometrists providers refer patients who need Medicare advice.
  • They also receive referrals from existing clients and from wealth management firms.


• 09:18–11:01 – Compliance & why you can’t cold-call seniors. Tom explains that Medicare rules prohibit unsolicited phone calls to Medicare prospects:

  • Prospects must call the agent or explicitly consent before discussions.
  • This makes direct mail and referral-based marketing even more important.
  • Insurance companies also feed leads to his agency when they see how well his team services clients.


• 11:01–13:29 – Working with wealth managers and employers.

  • Tom partners with multiple wealth management firms who send him clients turning 65.
  • He and his agents help reduce costs for companies and older employees by shifting them from expensive employer plans to Medicare when appropriate.
  • This is especially powerful for cities, counties, and mid-sized employers with many older workers.


• 13:29–16:27 – Building & supporting a 240+ agent team.

  • Tom describes recruiting Farmers Insurance agencies early on to add Medicare as a line of business.
  • Over time, many new agents have come via referrals from carriers impressed with how well Caress Insurance supports its people.
  • He focuses on long-term residuals, investing heavily in agent marketing and tools, so they can build durable books of business.


• 16:27–18:22 – Industry outlook: fewer agents, more seniors.

  • Tom shares conference insights: fewer agents today than pre-pandemic, but a huge increase in Medicare-eligible people coming.
  • He talks about the challenges of annual enrollment (Oct 15–Dec 7) and the need for office staff and software to manage thousands of clients.
  • He highlights how e-apps, CRMs, and survey tools allow his agency to proactively notify clients of plan changes and options.


• 18:22–21:01 – Tom’s biggest challenges: family & early leadership tests.

  • He shares that his biggest life challenge is keeping family close-knit across four children and 16 grandchildren.
  • He and his wife decided to invest in individual time with each grandchild.
  • He recounts being drafted during Vietnam, unexpectedly put in charge of 90 men because he’d played college sports a jarring leadership baptism.


• 21:01–23:12 – From micromanager to delegator.

  • At Toshiba, after being promoted, he was shadowed by an industrial psychologist who told him he was a micromanager.
  • Tom learned to ask for ideas, pick good ones, and assign them back to the person who suggested them, empowering them to own execution.
  • This shift transformed his management style and remains central to how he runs his agency today.


• 23:12–26:44 – Lightning round. Tom answers rapid-fire questions:

  • Coffee or tea? Neither.
  • Cats or dogs? Dogs.
  • Favorite tech: his golf carts (two, including a Jaguar-themed one).
  • Favorite phrase: “Don’t fix the blame, fix the problem.”
  • Biggest money rule: spend less than you make.
  • Bucket list: playing Royal Dornoch in Scotland; he’s also played many top courses worldwide.
  • Financial milestone: wants a private jet.
  • Money mistake turned lesson: don’t buy stocks on leverage.
  • Advice to younger self: start saving earlier.


• 26:44–27:53 – How to connect & closing.

  • Tom gives his direct phone number and email and invites calls or texts from anyone needing help or advice.
  • Dan thanks him for his time and insights and closes the episode, encouraging listeners to keep building wealth and enjoying life.

In this episode of Making Sense of Your Money, Dan sits down with Tom Caress, founder and CEO of the Caress Insurance Agency, for a candid and practical conversation about Medicare, retirement healthcare, and how one decision can dramatically change someone’s financial and physical well-being.

Tom’s journey into Medicare started at home. Nearly two decades ago, his widowed mother moved in with him and was spending $400 per month on a Medicare plan she didn’t understand, while only receiving $800 per month in Social Security. Following his father’s instruction, she had never questioned it. Tom got licensed with Aetna and UnitedHealthcare, studied the options, and moved her to a Medicare Advantage plan that allowed her to keep her doctor while eliminating that $400 premium. With one change, he essentially doubled her spendable income. That experience opened his eyes to how many people were overpaying and under-served—and it became the catalyst for his Medicare-focused career.

Before Medicare, Tom’s background was in computing and corporate sales. He ran regional operations for major companies like Toshiba and Samsung, hiring and leading teams and selling to large organizations. He was drawn to the power of residual income and admired Warren Buffett’s philosophy of building streams of cash flow that arrive every month. But what he found in Medicare was even more compelling: a way to combine residual income with tangible, life-changing impact on individual people.

Today, Tom’s agency has grown to over 240 agents nationwide. They specialize in helping people understand Medicare, make the right enrollment decisions, and adjust plans as life changes. His clients range from former NFL Super Bowl coaches and legislators to world-class musicians and everyday retirees. The common thread: they are experts in their own fields but largely unfamiliar with the intricacies of Medicare. Many have always been covered by employer plans and are now facing a confusing mix of Part A, Part B, Medicare Advantage, supplements (Medigap), and prescription drug plans.

Tom’s philosophy is simple: educate first, then let clients decide. He doesn’t believe in simply telling people, “Here’s your plan.” Instead, he breaks Medicare into understandable pieces and focuses on the three things that matter most: doctors, drugs, and dollars. Do you have a doctor you love and want to keep? Is nationwide access with no referrals crucial to you? Are you healthy and mainly concerned with low premiums and gym benefits? Or do you have complex conditions where consistent access to certain specialists or medications is the top priority?

Using those answers, he explains the trade-offs between Medicare Advantage plans (HMOs, PPOs) and Medicare Supplements plus drug plans. Some clients prioritize cost and are happy with an HMO or PPO that includes extra benefits like dental and vision. Others insist on travel flexibility and the broadest possible provider access and are willing to pay higher premiums for a supplement. Tom often sees couples where one spouse is on an Advantage plan and the other is on a supplement because their health, preferences, and risk tolerance differ. His measure of success is whether the client feels informed, confident, and in control.

On the business side, Tom explains the challenges of Medicare marketing and compliance. Agents cannot cold-call seniors; prospects must call them or explicitly consent to being contacted. That’s why his agency relies heavily on direct mail campaigns, educational workshops, and warm referrals from doctors, pharmacies, dentists, and optometrists. Many seniors walk into a provider’s office with a bad plan or drug coverage that isn’t working; those providers, knowing their limits, send them to Tom’s team for specialized help.

Another major referral source is wealth management firms. Financial advisors often provide comprehensive retirement planning but need a Medicare expert to complete the healthcare side of the puzzle. Tom sees this as a natural fit: his agency doesn’t handle investments, and advisors don’t manage Medicare enrollment. Together, they ensure clients have both their money strategy and their healthcare strategy aligned.

Tom has also built deep partnerships with employers and HR teams. Many businesses including counties and cities have older employees on costly group health plans. By counseling those employees on when and how to transition to Medicare, Tom can often help them get better coverage for less money, while also reducing the employer’s healthcare spend. In some cases, he’s helped set up ongoing relationships where HR departments send every approaching-65 employee directly to his team for guidance.

Scaling to hundreds of agents didn’t happen overnight. Early on, Tom and his son proactively approached Farmers Insurance agencies across California when Farmers cut commissions, offering Medicare as a new, residual-based product line. He trained them, provided marketing support, and showed them how to integrate Medicare into their businesses. Over time, the agency’s reputation led major insurance carriers UnitedHealthcare, Aetna, Humana, Blue Shield, Cigna, Mutual of Omaha, and others to refer agents to Caress Insurance because they saw how well Tom’s team supports and retains agents.

Tom sees the future of the industry as both challenging and full of opportunity. There are fewer licensed Medicare agents now than five years ago, but the number of people entering Medicare is about to spike as more baby boomers hit 65. This imbalance makes efficiency and technology crucial. His agency uses electronic applications, CRM systems, and survey tools that automatically collect client information, flag plan changes, and streamline annual reviews. This allows agents to serve large books of business while still delivering personal touches.

The conversation also delves into Tom’s personal development and leadership journey. Drafted during the Vietnam era, he found himself, at 18, suddenly in charge of 90 men because he was one of the few with college experience and sports background. Later, in his Toshiba role, a consultant bluntly told him he was a micromanager—he asked for input and then told people what to do anyway. That feedback pushed him to change his management style: now he listens, highlights others’ ideas, and lets them own execution. This shift from control to empowerment has shaped how he leads his agents and staff today.

In the lightning round, listeners get a lighter glimpse into Tom’s life. He’s passionate about golf (especially Scottish links like Royal Dornoch), loves his custom golf carts, adheres to the core rule of spending less than you make, and warns against buying stocks on margin. If he could talk to his younger self, he’d say: start saving earlier and let compounding work in your favor.

Dan closes the episode by underscoring how crucial Medicare planning is to a strong retirement plan. Healthcare costs and coverage decisions can make or break a retirement budget, and having someone like Tom in your corner can significantly reduce stress and uncertainty. Tom invites listeners, prospective agents, and other advisors to call or text him directly if they want help navigating Medicare or exploring a partnership.

Announcer: Brought to you by Tailored Wealth, helping business leaders live their version of a rich life.

Announcer: Welcome to another edition of the Making Sense of Your Money podcast, where we cut through the financial noise and help business leaders to make smart, confident money decisions.

Dan: All right, welcome to another edition of the Making Sense of Your Money podcast, where we help you take control of your finances, minimize uncertainty, and maximize your wealth potential.

Dan: I'm your host, Dan Pasone. I am the founder and CEO of Tailored Wealth. And today I am excited to have a very special guest. I've got with me Tom Caress. Tom is the founder and CEO of the Caress Insurance Agency, and Tom and his team help individuals throughout the country to find effective Medicare solutions.

Dan: So, I'm excited to get a chance to have you on today, Tom. Thanks for joining us.

Tom: Hey, thank you. Thanks for having me.

Dan: Yeah, you bet. You bet. This is going to be a lot of fun. We've got a lot to cover. I'm really fascinated with your business and what you've been able to build, and I know our audience would love to get your expert take on some key topics.

Dan: So let's jump right in. First and foremost, can you just give us a quick 90-second overview of your business—what it does—and then tell us a little bit about how you got into it?

Tom: So Dan, what we do is actually, my mother moved in with me about 18–19 years ago, and I was involved with another product called AFLAC, which was indemnity insurance. I looked at her Medicare plan. My dad had died, and I thought, “Wow, she's paying $400 a month for a plan.” She didn't know what it was; she just said my dad told her not to go off of it. And she only made $800 a month in Social Security, and I said, “You know what, this can't be right.”

Tom: So I went out and got licensed with Aetna and UnitedHealthcare, looked at their plans, put her on a Medicare Advantage plan same doctor she already had saved her $400 a month, and doubled her income. And I thought, you know, if I can do that for my mom, there are a lot of people like this.

Tom: I started marketing to people over 65 and was super successful in helping people first understand Medicare the basics like when it started (1965), who wrote it, what the components are, whether they wanted to see certain kinds of doctors, whether they were very healthy or very unhealthy and helping them navigate and find a plan that was good for them. And you know, after 65, what's more important than your health and your wealth?

Tom: Even if you have a lot of wealth, you can't buy your health. And I have people hug me and want to fix me dinner because I put them on plans that give them access to the things they want to do and help them get it quicker. That's how I got into it.

Tom: My background was computers before this. I can't spell, but I'm really good with numbers. After I got to a certain point, I was put on a national advisory board with UnitedHealthcare one of 10 agents nationwide out of 160,000 agents so I must have been doing something right.

Tom: From that, I saw especially when I was able to see what the insurance companies do, how they lobby, how they go to Congress that anybody who didn't have a Medicare trusted advisor, an agent that would help them openly, and tried to make decisions themselves just didn't have enough information to make a good long-term decision. It could cost them money and time, and that's what I try to help my customers with.

Tom: From there, UnitedHealthcare came to me and said, “Hey, you've recruited some of the best agents by telling them about this. Why don't you become an agency?” My son and I decided to do that. We started with five agents; now we have around 242 or 243 agents contracted.

Tom: Most of them it's the 80/20 principle but we have a lot of people who have either organically come into the business or come from other walks of life and are enjoying the fruits of their labors, making a wonderful living and helping people in their own markets.

Dan: That's very cool. I love that. I'm always fascinated by people's stories, Tom, and what motivates them to get into their business. Was it that experience with your mom that prompted you to build what you've built today?

Tom: Yes. Before that, when I ran a Fortune 100 company in Europe for Toshiba and then worked for Samsung, I sold to big businesses. I was really good at it hiring people, understanding what kind of people could integrate with big business, teaching them how to present, train, and help others use computers.

Tom: When I decided to get into this business, the residual income from a business standpoint was intriguing to me. I listened to Warren Buffett talk about residuals basically getting something that pays you every month and I thought, “I want to do that.”

Tom: With AFLAC, I wanted to sell to businesses, not individuals. Until my mom moved in with me, I never really wanted to sell to individual people. But this ended up being the most rewarding thing I'd ever done in my life because I could see that I was physically changing people's lives.

Tom: Every year we have annual meetings for all of our customers, either as a group or individually, and a lot of times they're tear-jerkers. People come and tell me stories of what they were able to get done and how they didn't have to pay any money and got the best access to doctors.

Tom: In fact, I had a guy last year who was dying who called me and said, “I want to tell you you helped us 15 years ago get on these plans, and it saved me a fortune. I've had the best access. I know I'm going to die, but you've been a wonderful advisor, Tom.”

Dan: That's amazing. I love hearing those success stories. And we've only been chatting for a few minutes now, but it's clear how passionate you are about what you do and who you do it for.

Dan: So tell us, Tom, a little bit more about your ideal client. Who do you and your team ultimately help, and what do you help them do?

Tom: Most people I have ex-NFL Super Bowl coaches, athletes, running backs, judges, legislators, world-class musicians, on and on but most of them are really good in their area of expertise and know nothing about how to navigate Medicare because they've always worked for a company.

Tom: I'm able to break it down and make it simple for them, and I let them make the decision. I let the light turn on for them. I do not tell them what to do. If I haven't been able to figure out a way to educate them so they understand what's actually going on, then I probably haven't done my job.

Tom: I usually ask, “Tell me the most important thing you want out of this. Do you want a low-cost plan with great access? Or do you want to be able to go to any doctor in the country without a referral, and money for the premium is not an issue?” Then we discuss what's important to them, give them the choices, and they pick.

Tom: The people who pick their own plans with enlightenment are the ones who are the happiest. And of course, we also tell them how to get on Medicare if they don't know how.

Dan: That's very cool. I think I've picked up on a couple of things, but I want to hear it from you. What makes you and your firm unique in the way you help your clients figure out the best Medicare solution for their lives?

Tom: I think the biggest issue for most people is they either have a doctor they really like or they don't. I tell everyone the key to any plan working whether it’s a Medicare Advantage HMO, a Medicare Advantage PPO or HMO-POS, or a Medicare supplement (Medigap) with a prescription drug plan is that you have to find a doctor or medical clinic or staff that you have access to when you need it.

Tom: You never know when you’re going to need it. If you don't have that, then you need to find one. Then we need to find something that covers you while you're in that path and doing what you want to do.

Tom: I have many couples where one of them is on one type of plan and the other is on another. They have completely different needs and wants. Sometimes they argue, “We ought to both be on the same thing,” but usually I can get them to understand what's most important for each individual. Once you find that out, that's when they're happy.

Tom: In the last few years, there’s been disruption change and turmoil in the insurance market. We just had a big change in administration. People want to know, “What can I do if I want to change?” They want to be reassured that there's a path, and I tell them about that.

Tom: We have a monthly newsletter. We take every phone call. We have office staff. If somebody has a bad bill or can't get access to doctors, I know where to go in their doctor group to push a button and say, “Hey, this doctor’s got a stack of referrals and they're not escalating them.” I help them do that.

Tom: I tell our clients, “Call me first. Don't call an 800 number where you'll get one of 40,000 people. Call us we know you. We can help you. We know most of the doctors in the networks, and we will find a path to get you the best service.”

Dan: That makes a lot of sense. And that's how I want to be treated too. I want somebody to take care of me whether it's my wealth management, my golf game, or my travel. I want somebody who can help me, and I think that's how you treat everybody.

Tom: Exactly.

Dan: Well, I know someone who might be able to help you in the wealth management space, but if you find someone who can truly help me with my golf game, I would love to be connected with that individual.

Tom: That's a whole different story. I got a great tip yesterday, but that's beside the point.

Dan: I love it. I love getting a new tip.

Dan: Tom, what are the biggest challenges that your clients face?

Tom: The biggest challenges, I think, are understanding. There’s a group of people who are very healthy and want to keep that lifestyle. They want simple. They want access to gyms, they want to be able to go to the doctor when they need to, they want extra benefits, and they don't want to pay a whole lot.

Tom: Then you have people who have money and want access to everybody when they need it, and they're willing to pay for it. And then there are others who don't really know or care they actually want us to pick, which we won't do. I try never to pick for anybody.

Tom: So we're able to help them no matter which category they're in. Twenty years ago, Medicare Advantage plans had a very small percent of the market. Now they're like 60% of total enrollments nationwide and around 75% of new enrollments.

Tom: There are people in the federal government who are for and against them in every market. For some people, Medicare Advantage is exactly where they need to be. They need somebody talking to them; they need a quarterback before they get handed off to a specialist. Otherwise, they'd be going to specialists they don't need and using the system incorrectly.

Tom: For a lot of people, they need a primary doctor that's what I'm trying to say so they have somebody who can analyze things, look out for their best interests, and say, “You know what? See a therapist,” or, “You don't really need that; what's causing those issues might be something else. Maybe you ought to go on a weight management program.” Most people don't want to hear that, but that may be the best thing they need.

Dan: Sure. And it's clear there's a real need for what you and your team provide. How do your clients typically find you, Tom? You've built such a big agency across the country now how do they find you?

Tom: There’s a myriad of ways. When someone wants to become an agent organically, they have a past history of people they've dealt with. When I first started, we did flyers. We actually have our own in-house marketing program that we send out.

Tom: We’re the number one sender of flyers in Riverside County, California we’ve been told that by the post office. And it's for agents all over the country. We specialize we know who's turning 65, when they’re turning 65, and we market to them.

Tom: If you send out a thousand flyers, you're going to get about 10 to 15 people who respond. That's because they're interested. They want to know six months out, four and a half months out that’s the key market. They’ll contact us and come to a community meeting, or they’ll want to come on a Zoom or a phone call. That's how we get people started.

Tom: Also, there are doctors who need patients, and we team up with doctor groups or doctors’ offices. We have an agent who works directly with them so that when somebody comes in and says, “I have a terrible prescription drug plan, can you help me?” the office can say, “No, but we have an agent who can.”

Tom: Same thing with pharmacies, dentists, optometrists those providers don't really understand the Medicare market. They understand how to get paid as a provider, but we can help them actually get more customers and get the right customers to them in the marketplace.

Tom: Same thing with wealth management. We have many wealth management companies. I'd say a third of our agents are teamed up with two or three wealth management groups that feed them leads of people turning 65.

Tom: We also have maybe seven or eight agents who have figured out that they can go to HR people in markets where there are companies with 100, 150, 200, 300 employees and they have people turning 65 or already 65 on company plans. The company has to pay a fortune for them and can't push them off, but those employees would be better off on a Medicare Advantage plan. They’d have better insurance and it would cost both the company and the person less money.

Tom: In those cases, we have agents who even work with counties and cities that we do this for. Those agents are unstoppable. They usually end up hiring two, three, four, six, ten agents underneath them to help.

Tom: So it's a myriad of ways of getting leads. Locally, I also do radio and TV in my market. It's not affordable in every market, but it is in certain markets in the country.

Tom: We've tried every form of marketing. It's amazing seniors still open their mail. And you can't call them; the Medicare business doesn't allow you to call anybody directly. It's illegal. They have to call you as the customer, and then you can talk to them, and they have to agree to the relationship.

Tom: That's a big part of it. And then there are two other huge pieces. Once you start helping UnitedHealthcare, Aetna, Humana, SCAN, Blue Shield, Mutual of Omaha, Cigna, Blue Cross, and you start selling their product in a market, they come to you and say, “We have more leads for you.”

Tom: We get people who come to us, and we get them connected with the insurance companies. And then, once you get a certain book of business, we have a unique way to help agents manage their books of business both through CRMs and marketing so they can double their business if they have two or three hundred customers, just from referrals.

Dan: Got it. That makes sense. You're talking my love language there, Tom, so I can definitely relate.

Dan: You mentioned a couple different referral partnerships, and we always like to highlight that here because we've got a lot of folks in different aspects of the financial services and health industries that tune into our content. Tell us a little bit about how you or your agents collaborate with referral partners. You mentioned wealth management that's my business, so it's near and dear to my heart but tell us a bit more about how those partnerships form.

Tom: Yeah, I have two wealth-management groups I've been with for a long time that’s where I park my own income and assets. I didn't start out that way, but they came to me and said, “Listen, we have people turning 65,” and they send me customers.

Tom: When we do newsletters, people come to us and say, “Tom, what other insurance do you sell? Do you sell life insurance? Do you sell long-term care?” They start to trust you as an adviser, and then we refer those people to the wealth-management firms. It becomes a great relationship.

Dan: Yep. We've seen that work in our business as well, so I totally get that.

Dan: Tell us a little bit about the agents you've hired. You mentioned over 200 across the country. How have you built up your team? Getting clients is one thing, but building a team is a different challenge. How have you been able to do that successfully?

Tom: When we first started, my son and I went out and found out that Farmers Insurance was cutting their commissions, and it was becoming a struggle for the agencies. So in California, we wrote to every agency and ended up signing up about 15–20 of them. Most of them are still with us.

Tom: We went and talked to them, and it was the right thing for them to do to add a product. Now, most of our new agents are family referrals either from customers or people in the industry. I'd say over half of our new agents right now come from insurance companies. When people go to the carriers and say, “Who should I talk to?” they say, “You’ve got to talk to Caress they actually take care of their agents.”

Tom: I had a person who runs Southern California for a major insurance company say to me yesterday, “Tom, I'm amazed. Your agents I know what you do, and you do more than any other agency.”

Tom: We try to help them. We're not worried about the upfront money we make; we try to spend it on the agent. My thought is: if I can get an agent in front of 30 people a month, within two or three years even if all the money I make off them goes into that they'll make more residuals, and ten years from now we'll all be making more money.

Dan: Well said. That's a good perspective playing the long game.

Dan: Where do you see your industry going in the next 5–10 years, Tom, and how are you staying on top of that? There are obviously interesting demographics across the country, and what you do is such a big need. What are the biggest challenges you see?

Tom: It's interesting. I just came back from a conference in Nashville last month. It was freezing they had the worst cold spell, and of course I hit it perfectly.

Tom: Two things came out of that. Before the pandemic, they listed how many agents there were nationwide. There are fewer agents licensed today selling Medicare than there were five years ago. And in the next ten years, the number of people who will be Medicare-eligible is going to go up by almost 300%.

Tom: So the problem is efficiency. At the end of the year, during open enrollment, when you need to meet with people, there have been all kinds of talks by the federal government about changing things. It used to be you could change on your birthday month on certain plans. Now, basically, there's an open enrollment period from October 15th to December 7th when people can change, unless they move or have a special election period, which you need to know in every market.

Tom: What's happening is that you have to figure out how to deal with those customers annually. When you have two, three, or four thousand customers, you have to have an office staff, and we teach agents how to do that. Then there’s the software.

Tom: My background is computers, and we have the latest software components. When I first started, every time you enrolled somebody, it was a paper application and you faxed it in.

Tom: Yesterday I had a unique day here at the end of March, we had eight enrollments, eight applications, all done over the phone. I think all of them were referrals to me personally, and we were able to give them whatever they wanted some were changing plans. It's easy to do with the right software. You put the information in, they look at it, they get to review their own information, approve the application, and then submit it. It goes straight to CMS, and they're in.

Tom: Automation is key the same thing for customer service. We have survey software that goes out in August or September: “Has anything changed?” If it has, it goes back into the customer database and updates it.

Tom: So when open enrollment comes, we can run a list: “Hey, this company is pulling out of a market in Missouri.” Everybody we have in that market we can contact them October 1st and say, “Your plan is ending or changing. Let's set up a time on the calendar to discuss what your choices can be and what you want to do in the coming year.”

Tom: So: automation, efficiency and then you still have to take the time with the customer. The people who don't do that. A lot of younger agents, or agents who haven't succeeded, basically just want to enroll people. They want the upfront money and don't really want to handle customer service. They refer clients back to the insurance company, and then you might get somebody in the Philippines, or a brand-new hire who gives you the wrong information. That's a shame.

Dan: Makes a lot of sense. Thank you for sharing that.

Dan: Okay, we're going to shift gears a bit and talk about you now. But I have one more question before we get to our lightning round, which we have a lot of fun with.

Dan: What's the biggest challenge you've faced in your life to this point, Tom, and how has that shaped the way you do business?

Tom: The biggest challenges to me are family, if that's what you're talking about. My goal is to keep my family together. I have four children, and now I have 16 grandchildren. All of them are tied to the business one way or another. They saw that I was successful and said, “Hey, how do I get involved a little bit?” or their spouse did. That's been comforting, because they're all doing quite well.

Tom: I didn't ask them they just wanted to do that because they could see it was something I enjoyed. But I think getting a family to stay together is probably your biggest challenge and responsibility handling that, especially when you have diverse views on politics and way of life.

Tom: My wife who is probably my best adviser and I decided a long time ago that we need to spend time with every grandchild individually. We ask what we can do to help them with life and talk to them one-on-one. So challenges are mainly family things like that.

Tom: Business-wise, my biggest early challenge was something I didn't see coming. I was drafted when I was 18, during the Vietnam War, and I didn't know what was going to happen. I’d played football in high school and was going to play football at junior college, and I played tennis. I was drafted, and they said, “Who has gone to college?” Maybe seven of us raised our hands out of 90 guys. Then they said, “Who has played college sports?” I raised my hand I was the only one.

Tom: They made me the commander of the 90 guys. I’d never been in leadership before in my life from that standpoint, and a lot of them were older than me. I thought, “Uh-oh.” That was probably the most challenging time for the first few weeks because I had no idea what to do.

Tom: The same type of thing happened when I decided to get into the computer business. I went to work running small dealerships, and a guy named John Rayfield who just passed away and Phil Burton were looking for a regional manager for Toshiba in 1984. They had one product at the time a printer. They ended up hiring me, and I had one employee, and I had to fire that employee after the first two weeks. They asked me to, and that was an interesting challenge because I had to face things I’d never done before.

Tom: Both the military and Toshiba turned out to be wonderfully successful experiences. I found out in the service that I was really good at math. I wanted to be a helicopter pilot, but they wouldn't let me because they said I scored too high on the math test. They put me in nuclear missiles instead, which kept me out of Vietnam and off helicopters 50% of those were shot down so there was a bit of divine intervention.

Tom: Math has always been my strong point. At Toshiba, after a couple of years doing really well, they put an industrial psychologist with me for a week a major consulting firm wanted to see how I managed.

Tom: After a week, he took me aside and said, “You’re a micromanager.” I said, “What? I'm not a micromanager.” He said, “Yes, you are. When you're with a group of people and you ask for their ideas, you do a good job. But then you tell them what to do when you’re done.” I said, “Well, isn't that what a manager does?” He said, “No.”

Tom: They changed my way of thinking about delegation. He said, “If you’ll just take the ideas, and when you see an idea that's like yours or a really good one, say, ‘I love that idea. Can you do that? Can you make that work?’ and then tell that person to go do it. It’s their idea, and they'll do everything in the world to make it work.”

Tom: I went from a micromanager to a delegator, and that's how I've run my life ever since. I've been way more successful because I find people who value what they do, we agree on goals, and they're willing to do anything to be successful because they told you they could do it.

Dan: I've had similar experiences earlier in my career, and I couldn't agree more. That shift from micromanager to delegator is an absolute game-changer in business and in life. We're on the same page on that one.

Dan: All right, Tom, we're going to finish here with what we like to call the lightning round. I'm going to give you a question, and I want you to give the first answer that comes to mind. You ready?

Tom: Yes, sir.

Dan: We'll start easy. Coffee or tea?

Tom: Neither.

Dan: Neither, okay. Cats or dogs?

Tom: Neither… actually, dogs.

Dan: Dogs, okay. This one's right up your alley, so I'm interested to hear your thoughts. What's one tool or technology other than your computer or phone that you can't live without?

Tom: My golf cart.

Dan: Your golf cart. All right. I love that. Do you have a customized golf cart?

Tom: Two. I have one in Wyoming, and I have a Jaguar down here.

Dan: I love it. I'd love to check that out sometime you'll have to send me a picture.

Dan: Favorite quote or phrase about money or success?

Tom: You know, John Rayfield taught me one thing about people “Don't fix the blame; fix the problem.”

Dan: I love that. Favorite book on finance or business?

Tom: Favorite book on finance or business? I don't have an answer on that.

Dan: Do you have a personal productivity, finance, or business hack some sort of best practice you use?

Tom: Spend less than you make.

Dan: Okay, love that. One bucket list item you've already accomplished?

Tom: I wanted to play Muirfield in Europe, and I got to play that a couple of years ago. I've played almost every golf course except Augusta and Pine Valley in the world that I've wanted to play.

Dan: I'm going off script here what's your favorite golf course that you've played?

Tom: No doubt about it: Royal Dornoch in northern Scotland.

Dan: I've heard great things. Have you been to Augusta?

Tom: No. I only want to go if I can play.

Dan: I've been to Pine Valley, so I'm lucky from that perspective. I haven't played Augusta, but I've been to the Masters and I've played Pine Valley those are treats for sure.

Dan: What's one financial milestone you're still working toward?

Tom: Private jet.

Dan: I love that. What's one financial mistake you've seen turn into a valuable lesson?

Tom: Don't buy stocks on leverage.

Dan: Love that. We often have to advise our clients on that. And if you could give one piece of money advice to your younger self, what would it be?

Tom: Start saving and putting money aside earlier.

Dan: Yep, that's a common one for sure.

Dan: All right, that's great, Tom. Finally, if our listeners want to connect with you, get information on your firm, or if there's an aspiring agent out there who wants to learn more about your agency, where can they find you?

Tom: I'm a simple guy. I have lots of phones but only one main number. They can reach me at 760-413-9749 call me or text me. Or email me at caressinsurance.comtom@gmail.com. I answer every phone call and every text. I'd be glad to help anybody whether they want to work for somebody else or with us. I'll just give them advice. I've been very blessed, and I don't mind helping other people. I've had great mentors in my life, and I'm willing to help others.

Dan: Very cool, Tom. That's a great perspective to have. We appreciate you sharing the personal info. If you're okay with it, we'll put that in the show notes as well.

Dan: This has been great, Tom. I really appreciate your time today. Thanks for sharing your time, your insights, your stories, your lessons with our group.

Dan: This has been another episode of the Making Sense of Your Money podcast, this week with our guest, Tom Caress. Tom, thanks for being with us.

Tom: Thanks, Dan. Appreciate it.

• Caress Insurance Agency: Tom’s Medicare-focused agency helping individuals and training agents across the country.
• Medicare overview: For official explanations of Parts A, B, C, and D, see government resources such as Medicare.gov.
• Annual Enrollment Period: Typically runs from October 15 to December 7 each year, allowing enrollees to change Medicare Advantage and Part D plans.
• Agent & marketing rules: Medicare and CMS rules strictly regulate how agents can contact beneficiaries and advertise plans.
• Tailored Wealth: Dan’s firm, which integrates Medicare, Social Security, and healthcare costs into broader retirement planning.

• Tailored Wealth – Work with Dan and the team
• Making Sense of Your Money – Podcast Archive
• Resources for Business Owners & Professionals
• Contact Tailored Wealth

If you or someone you care about is approaching Medicare age, consider:

• Mark your calendar: Note when you (or your spouse/parent) will turn 65, and start planning 6–3 months beforehand.
• Clarify your priorities: Make a short list of:

  • Doctors and specialists you want to keep seeing
  • Current prescription medications
  • Your travel patterns and where you might need care
  • Your budget and risk tolerance (low premium vs. broader access)


• Attend an educational session: Join a Medicare 101 webinar or meet with a local agent for a high-level overview before making decisions.


• Coordinate with your financial plan: Work with a firm like Tailored Wealth to integrate Medicare premiums, supplements, and out-of-pocket costs into your retirement projections.


• Connect with a Medicare expert: Reach out to an independent broker such as the Caress Insurance Agency for personalized guidance, plan comparisons, and ongoing support.

To keep sharpening your decision-making around healthcare and finances, explore more episodes of Making Sense of Your Money or connect with Tailored Wealth to build a coordinated strategy for retirement, investments, and benefits.