Why Great Retirement Planning Takes a Team
Episode 44
Why Great Retirement Planning Takes a Team
Published on July 21st, 2026
Episode Summary
Episode 44 of Retirement Tax Matters marks the one-year anniversary of the podcast, opening with a look behind the scenes at the growth of the community. Garrett and Adam explore how consistently showing up to produce a weekly podcast shares a surprising number of parallels with navigating a successful retirement. The central focus of the conversation highlights how collaboration can be a powerful ingredient in a retirement plan, helping high-net worth retirees balance their financial planning with real life. Working with a team does not mean you have to hire a financial planner, but rather points to the benefit of opening a deeper dialogue with the people closest to you. For married couples, intentionally leaning on a spouse who may be less involved in the family financial finances can bring a healthy perspective that keeps you from optimizing a formula instead of reaching your actual family goals. If you're not married it might mean talking out loud with a child, roommate or friend. However you do it, leaning on a team framework helps retirees manage personal blind spots and navigate retirement with more clarity.
Key Tax Planning Questions
Question 1: How do I get an disinterested spouse more involved in our finances?
In a majority of married households I’ve worked with over my career, one spouse usually takes the lead on managing the family finances. My wife and I face this same dynamic in our own home, so I know firsthand that it’s common. However, for retirees in the $2M–$8M tier, navigating this communication gap can feel uniquely challenging because the long-term stakes feel high.
If you’re always managing things yourself and have built a sizable portfolio, your current retirement distribution plan might make perfect sense to you, but it can look like a puzzle to a disinterested spouse. You may have already taken the step to hire a financial planner to protect the family portfolio for your spouse if you pass away early, yet you find they still have no desire to sit through your regular review meetings.
One feeling I have is that it may be a difficult road to try and turn your spouse into a similar version of yourself. Your partner may not share your same enthusiasm for navigating financial opportunities in the federal tax code or evaluating portfolio performance, but there’s a good chance they might possess other skills to meet your lifestyle goals that are just as vital to a secure retirement.
I’ve seen personally when I’m in a meeting with a married couple, when we go through the numbers and tax planning the less involved spouse eyes can glaze over. But as soon as we drop the number talk, the less-involved spouse often becomes deeply engaged.
I have walked alongside many surviving spouses who had to step into the financial lead role after a spouse passed away, and they almost always do an exceptional job. They might not approach the family finances exactly the way their partner did, but they bring their own distinct style, virtues, and clarity to the table. Finding the right balance in retirement planning requires the unique perspectives of both partners, not just the one tracking the market.
I’m not sure there’s a golden bullet answer here on how to solve this issue. In a situation where there’s a lack of confidence, you could consider setting up a trust to control income. We did an episode a few months back where you might consider purchasing an annuity for your spouse to live on if they live longer than you. You might consider a financial planner. Or like many situations I’ve run across, a surviving spouse will rise to the occasion of managing the family finances when the time has come.
Full Episode Transcript
Adam: Good morning, and welcome to Retirement Tax Matters. I'm Adam Reed. This is Garrett Crawford, our resident CFP® professional, and we have a special episode airing today. It's our one-year anniversary.
Garrett: A celebration, fireworks. We should have confetti going off everywhere.
Adam: It's like the July 4th 250th anniversary. But yes, I think we were looking back today, and our first ever episode was July 23rd of last year. Which is funny because my son was born last year on July 23rd. And I was wondering, "How did we post this?" I guess we had posted it the week before, and then my wife went into labor and had him. So, happy birthday, Bennett. And then on the day that we are recording this, my six-year-old turns six today. So, it is a lot of summer birthdays. Happy birthday, Dawson.
Garrett: Yes, summer birthday celebrations all around. We should bring them in one year.
Adam: It is funny, they are young enough where if I show them this episode later, they are going to say, "I was on YouTube." They are going to think they are famous. I am not going to show them the view count. I will just let them think this is a big exciting video.
Garrett: In the comments, "happy birthday, Bennett" would be a great one.
Adam: There we go. Yes, blow it up. Happy birthday, Bennett. But anyway, maybe a good segue. I think as we have been building this YouTube channel and working on it, if we go back and look at that first video, we have come a long way.
Garrett: I think so, a new backdrop and some new microphones.
Adam: I like to think that maybe we are getting more comfortable in front of the cameras. It is kind of awkward that first time.
Garrett: You were always naturally comfortable.
Adam: It just feels weird though. You are just talking into the abyss, and it is cool to see that some people are following along and listening.
Garrett: I remember that feeling too. When we started this, we were looking into our camera here, and I just remember it is a black abyss out there. Who knows if somebody is watching, but we are just going to show up and faithfully do this. But I remember that feeling. Who is out there? What is in the abyss? But here we are.
Adam: As we are building this community, just for you guys, I think we are almost at 1,000 subscribers on YouTube.
Garrett: Wow.
Adam: I feel like that is a fun milestone.
Garrett: More than I would have thought.
Adam: Yes, we are over 900 now, so I would think probably in the next month or so, over 1,000. We have had a couple of videos go viral for us. Not on a MrBeast level or Dave Ramsey, but we have. And then I think on Apple and Spotify, we have a few hundred people listening every week and tagging along. So it has been a fun journey, and we appreciate you guys tagging along with us. I do not want to be too long-winded with the thank you and the excitement, but it is a cool milestone.
Garrett: I totally agree.
Adam: We are here doing it because you guys are following along.
Garrett: Yes, thanks for joining.
Adam: I think if we were still at one subscriber and ten views a video, I am not sure we would have made it a full year. So it is exciting to see some traction as we grow.
Garrett: Absolutely. And actually having real people calling us, talking to us, and getting to know them. I have told people this year that we are from Knoxville, Tennessee, but we have had to broaden our horizons. So we take West Coast phone calls, New York City, and all over the country. People are tuning in and listening, so it has been pretty fun.
Adam: This year I am thinking we go global, start taking calls from Tokyo, Berlin, Germany, and France.
Garrett: We are going to have to get an international tax expert in here for that. Maybe you could do that in your free time.
Adam: Yes. Raising three boys, I will just brush up on that while I have all these little kids in the house. But I think one of the things we wanted to discuss today is building this podcast, seeing it grow, and how it reminds us of financial planning. I wanted to hear a little bit about your background, Garrett. As we got into the podcast space, we had the end goal in mind, but there were a lot of pivots and challenges along the way. I would love for you to share about yourself as a natural DIYer, getting into this, and now working with me as a team. Just share some thoughts you have had as we reflect on podcasting and look at our daily financial planning for our clients. What are some parallels you see, or what are some things that have been on your mind?
Garrett: I think with an anniversary, even with clients, when you reach milestones, it is helpful to look back and see what you learned and what you could have done better. I think that is all part of a planning development process. One cool thing about what we are doing is that I have been in the industry now for 13 years, and our registered investment advisory firm has been around for a long time. It is not like you and I are hanging out in our garage wondering how we are going to find a new client through podcast marketing. We are coming from the opposite side where we have a stable, mature firm. Even regarding financial capacity, we could put money into this. But our feeling has been to keep it organic. Instead of doing Facebook ads and spending tons of money to try to grow this thing, we have just tried to faithfully show up every week and share these conversations that we have had with clients, and if it catches on, great.
Actually, one funny side story about my premise for doing this is from when I met Adam a year and a half ago. We were growing, and we needed to find another advisor to help support the number of clients that were coming on board. It was really just a matter of needing another helping hand around the office. When you showed up, we had no intention of doing this podcast at all. That was not on my radar. But as I got to know you, I thought you would be really good at this. The behind-the-curtain thing that I have shared with a couple of people, which I do not think I have ever shared here, was that I did not have a real formal training process and plan when you came on board. I knew we were doing this tax planning, and I thought that since Adam seems to process information quickly, what if we did a podcast? He could be the emcee, and he would have to sit there and listen to me talk about advanced tax planning for hours. That was part of the dual goal. It could be a training ground for you to learn the corporate company speak and how we do it.
What surprised me was that only a month or two in, I realized you were absorbing all this really quickly, at a much faster pace than I ever would have guessed. It turned from a training ground into something I was actually really enjoying. I think we have kept it organic in the way we are doing it. Even the behind-the-scenes stuff is organic. We do all of our video production. We designed all the cameras and the software to do this. A lot of our natural giftings come into producing this. I think outsourcing it too early would cause you to lose some of the authenticity of the messaging we are trying to give.
Adam: To color that in a little bit more, I started at a more traditional financial advising firm where they manage investments, and that is the bread and butter. I had heard of things like Roth conversions, but I never really knew the details. I had never heard of an IRMAA surcharge before I came here. It is crazy to think about being in the industry for years and missing that crucial detail. It was fun to go from seeing the broad picture to zooming in on the painting for the first time. I realized how important things like IRMAA and the NIIT are, and I wondered why nobody else was calculating this stuff. It seems like I have sipped the Kool-Aid of tax return-driven financial planning because I think it is incredible, and I feel like so many people working with a traditional investment advisor are missing out on it.
Garrett: Absolutely. Shifting a little bit from the podcast anniversary celebration back to how this relates to retirement planning, I was thinking about our first year doing this and how I operate regarding business building and relationships. Do you remember when TED Talks were a big thing back in the 2000s? I am not sure when I last listened to a TED Talk, and I am not even sure if this was from one, but I remember listening to somebody talk about Steve Jobs. They shared a quote, which I hope was from him because it really impacted me. They said, "Great things in business are never done by one person. They are done by a team of people." That was attributed to Steve Jobs at an Apple town hall meeting. I remember thinking that my default wiring, probably like a lot of people watching our channel, is based on the idea that if you want a good job done, you have to do it yourself.
Hearing that quote challenged me. Much of the impactful change in the world, whether in a financial planning office, a group of doctors, or any occupation, is achieved by people working with others, not by themselves. There are solo podcast hosts out there, and that is totally fine. But regarding bringing you on board, when you do it yourself, you have control. Nobody is going to challenge your thought process. You are in an echo chamber where you are the smartest person in the room. With my 13 years of experience compared to your three years, there could be a temptation to think I know the answers much better. But working together these past three years, the discernment you have when I talk out loud about case design is incredible. Even just yesterday, I gave an answer for a client, and you suggested proposing it a different way. I realized your way was absolutely better. Years of experience are helpful, but when working in partnership, ideas you think are great might need the different perspective that somebody else can provide. That is really valuable.
The transition from a podcast to retirement planning is similar. If I never came into this industry, I would have gone down the route of accumulating and investing for the future by picking index funds or target date retirement funds. I would have thought I could do it by myself and not wanted anyone sharing in my wealth building. But then you get to retirement and figure out things are trickier than you thought. It is like starting a podcast. We thought it would be simple, but then we realized the camera formatting, video cards, and recording software are a constant struggle.
Adam: The part that gets me every week is that we set everything up the exact same way, but somehow some setting is always different. We know how you feel as a lot of the world adjusts to new technology.
Garrett: Retirement planning and the decumulation phase are filled with moments where you realize you never thought about an issue until it came up on your tax return, like the net investment income tax. One of the virtues we have learned through doing this podcast for a year is that it is not unlike retirement planning. Doing it in partnership and having other people help you makes a really big difference over multiple years.
Adam: Everybody has biases and blind spots. Working with someone you trust is really helpful because they can ask if you have thought about a certain angle or notice if you have a bad taste in your mouth about a specific topic. You can dig deeper into things that, if left to your own devices, would cause you to miss out on opportunities or useful tools in specific situations. I think that is helpful insight. We are not saying everybody should go out and hire a financial advisor. But what would you encourage people to do regarding teaming together? We have done videos in the past about building a team with a CPA and a financial planner that does tax return-driven financial planning. Where would you leave people today? What is the call to action for the DIYers out there?
Garrett: This applies to delegators too, the people who do not want to do it themselves. I think this is universal advice. There is an important skill set in talking out loud to somebody about anything important you are doing. If you hear this and think you need a financial planner, by all means, email us. We would love to entertain a conversation about working with you. But I am not saying everybody needs to rush out and hire a planner just because of this episode.
The main point is that your teammate could be a financial planner, it could mean having a deeper discussion with your tax preparer, or if you are married, it could be your spouse. I would like to major on that last one. From the comments left by our listeners, I can tell they are really smart and interested in taxes. If you are married and talking about IRMAA surcharges, Medicare, and the 24% tax bracket, I would be surprised if your spouse feels the exact same passion for tax planning. One thing I have learned in marriage, in working with Adam, and in helping retiree clients, is not to discount the spouse who does not care about this as much as you do. They will bring a skill set to your retirement equation that is probably very different. They might remind you that life is not just a math equation, and you do not need to optimize for every single dollar. They might suggest paying some taxes to enjoy life a little more instead of solely focusing on eliminating taxes to the government.
Time and time again, when I talk to a couple, I can sense the wisdom in the less involved spouse trying to reel the more dominating spouse back in. Every relationship is different, but when you are very good at something, you can have a tendency to lower the volume of those who do not spend as much time thinking about it. A great retirement requires a team. Your spouse might be an even better teammate than you expected. Or maybe you both need help, and a financial planner would be worth the expense. If you are not married, divorced, or widowed, your team could be a child you trust to speak your goals and fears to, or just a friend or roommate. The general rule is that even if you are really great or really bad at this, having someone come alongside you in partnership will lead to accomplishing greater things as a team.
Adam: I cannot speak for all financial planners, as there are thousands out there. Some are great, some are not, just like any industry. A lot of times, it could be as simple as getting a second opinion. Sitting down for an hour to discuss things can help you realize you are in a good spot. Meeting with somebody who has the technical chops can be beneficial. I have gone back and forth on email with people asking if they are on the right track. We are not making full recommendations to non-clients, but we can help discern if it would be a good idea to sit down together or confirm that they are on the right track. We are always happy to do that, and there is no obligation. We turn away probably as many people as we accept because it is not always a great fit for the optimizations we help people do.
This was an interesting episode to reflect back on a year and realize we are glad we built a team with a long-term vision. Looking back over our last three episodes, we did a highly technical one with screen sharing, one focused on the psychology of money, and now this one focusing on building a financial planning team. Our hope is that we hit a lot of different segments. If this one does not land with you, check out another episode.
We said we were going to work on not pitching at the end every time, but here we are. Check out our website, retirementtaxmatters.com. We have our year-end tax planning checklist, which I think is the best value you could ever trade your email address for. I am constantly blown away by the content Garrett puts together and sends out. If you are subscribed to that, leave a comment below letting others know it is truly a great tool. There is always an unsubscribe button at the bottom if it is not for you, but it is worth checking out.
Garrett: I want to end this episode by saying that one year in the books has been an honor. I anticipate doing this with you for a long time. We did 44 out of 52 weeks in our first year, which is pretty impressive. We are on pace to do even better this year. It has been great seeing you work with our existing clients and getting wonderful at these things. I anticipate we will be hearing more from you in year two. I look forward to continuing this with you.
Adam: Watch out, Garrett is going to give me the keys to the podcast. Who knows where we will end up. It will be a lot of fun. We appreciate you guys following along. Like, subscribe, and follow on Apple, Spotify, and YouTube. Check out the website. We would not be doing this without you all. We are looking forward to season two. They renewed us! I'm Adam Reed, this is Garrett Crawford, and we are Retirement Tax Matters.