EP 125: We’re Back: Roth Conversions, AI That Negotiated a Car Deal, and What We’ve Been Up to

After a long break from the studio, Brent, Matthew, and Josh are back—and they’ve got a lot to catch up on.

First up: Roth conversions. They’re everywhere on social media, and clients are walking in the door asking about them. But should you actually do one? The guys break down when a Roth conversion makes sense, when it doesn’t, and why paying the tax bill out of pocket changes the entire equation. Matthew shares a recent client projection that showed a million-dollar difference in inherited wealth—but it’s not a slam dunk for everyone.

Then the conversation shifts to AI—and it gets real. Brent tells the full story of how he used Claude to negotiate a car purchase entirely through text messages, landing the best price, the best rate, and catching a $3,000 paperwork error the dealership missed. Matthew talks about using AI to analyze his genetics and build a kid-friendly meal plan. And the team discusses how AI is already replacing medical scribes, editing podcasts, and doing the day-to-day work that used to take hours.

They also get into the darker side of AI and social media—bots, AI slop, dead internet theory, and why arguing in comment sections might mean you’re talking to a computer.

The episode wraps with personal updates: Matt’s reffing AYSO soccer, Josh’s son just starting T-ball on the Dodgers, and Brent’s savoring his last season as Little League president before his son ages out.

Timestamps

  • 0:00 — Intro

  • 1:00 — We’re back! What happened and why

  • 4:00 — Roth conversions: When they make sense (and when they don’t)

  • 5:00 — The social media hype around Roth conversions

  • 7:00 — Writing a check to the IRS: The real test

  • 8:00 — A million-dollar Roth conversion projection

  • 9:30 — AI beyond ChatGPT: Where things are headed

  • 11:00 — The leap from late 2025 to today

  • 12:30 — How Matthew used AI to refresh the podcast

  • 14:30 — Clients showing up with ChatGPT-generated financial plans

  • 16:00 — AI for meal plans, grocery lists, and travel booking

  • 17:00 — Brent’s car negotiation story (using Claude)

  • 21:00 — Human + AI vs. human alone

  • 23:00 — AI in medicine: Scribes replaced, blood work analyzed

  • 25:00 — AI fears vs. AI reality

  • 27:00 — Dead internet theory and AI slop

  • 29:00 — Why companies using AI are actually working more

  • 31:00 — Paid vs. free AI models: Why it matters

  • 33:00 — Personal updates: Kids, sports, and Orangetheory

  • 39:00 — Closing

Key takeaways

  1. Roth conversions aren’t for everyone—the real question is whether you can afford to write the tax check out of pocket and whether inheritance planning is a priority for you.

  2. AI has leaped past “fix my email”—it can now negotiate, analyze, plan meals, and handle complex multi-step tasks in your daily life.

  3. If you’re still using the free version of an AI tool, you’re working with technology that’s 2–3 years behind the paid models.

  4. The human + AI combo beats a human alone every time—for now.

  5. Social media drove the Roth conversion craze, and the tax cuts ended up getting extended anyway.

Links & resources

transcript

Welcome to the Retirement Plan Playbook hosted by Brent Pasqua, Matthew Theal, and Joshua Winterswyk of Evermont Wealth. This podcast dives deep into investment strategies, retirement planning, and current events, equipping you with the insights needed to craft a robust retirement playbook adaptable to any political or economic climate.

Join Brent, Matthew, and Joshua as they guide you through the complexities of retirement planning. Offering expert advice. to tackle challenges and the later stages of your journey. It's time to build your optimal retirement playbook. Now let's dive into today's episode.


Brent: All right. Welcome into Retirement Plan Playbook. Guys, it has been a very long time since we sat here together, been able to hit record, and it feels good to be back in the studio with you.

Matthew: Yeah, it feels great to be here. I’m Matthew for all you first-time listeners. Certified Financial Planner.

Josh: Joshua Winterswyk, Certified Financial Planner. It’s been way too long.

Brent: And I’m your host, Brent Pasqua. I’m an advisor at Evermont and President. We’ve been trying to get back in the studio for a long time. Our last recording was last year, I think, in the summertime. It wasn’t by design that we haven’t recorded since then. A lot of clients have been asking us when we’re gonna record again, and a lot of people have been asking us when we’re gonna record again.

Brent: But there were several things going on. As we’ve been continuing to grow, we’re just trying to find that new schedule that really allows us all three to be in here recording. At the same time, we also remodeled our entire podcast room, which is our secondary conference room. And so that threw the room off for several months.

Brent: We’ve finally been able to sit down. For the last couple weeks we’ve been trying to get in here and plan to get our next episode recorded, and we’re finally here.

Josh: We’ll have to upload some pictures to our social media of the new podcast room.

Brent: Yeah. We’ve done so much work to the office over the last six months. I feel like every time people come in, there’s something new.

Josh: We should record a tour.

Matthew: It’s a never-ending project.

Brent: Yeah. I think that I want the office to be up to the standard of what our expectations are, and there’s just little things that if I walk around, I want fixed and I want done a certain way. And so every time I see them, I’m pointing them out and wanting them to be changed. And that starts another project. I’m sure as most people who have remodeled anything like your house or any office know, once you start one thing, it leads to another thing and then another thing, and then a little project begins to have another project.

Josh: Yeah. And it’s our home. For us, it’s our home. For our clients, it’s also—to give some context—a 1950s home. So there’s always going to be projects, right? Anyone that’s ever lived in or experienced an older home, like you, Matt.

Brent: Yeah. I feel like the more work we’ve done, it’s starting to look less old though. I mean, there’s still projects here. I’ve got a list of things, as you guys know, that I still want to do. But I think it’s starting to look more modern in a sense.

Matthew: I just need to get some new furniture up here in this second conference room and I think we’ll be straight.

Josh: Podcast room, Matt.

Matthew: Second conference room.

Brent: It’s both. It’s a dual purpose. Which has been nice because since we have a lot of meetings throughout the week, we do have the secondary conference room now. When we’re double-booked on in-person meetings, we have somewhere else for people to go. Which is nice.

Josh: Yeah, it’s really nice. Helps us serve more people.

Roth Conversions — Should You Do It?

Brent: Matt, what is a big question that we’ve been talking about lately around here—some of the things that we’ve been putting in place and some of the things that are new that we’re working on with clients. What are some of the things that you want to talk about that we’ve been implementing over the last couple of months?

Matthew: I’ve been really enjoying our new tax planning software. It’s pretty cool when you actually start digging into the numbers. But my favorite tool—a lot of our new clients have been coming to us asking about Roth conversions. We’ve picked up quite a few over the last year who have been reaching out wanting to do these Roth conversions in their sixties.

Matthew: The tool works really, really well to model out those conversions. You could put their income in, all their various sources—because usually a retiree will have three or four different income sources—so you could put those in line by line and then model out the Roth conversion and get it right exactly to the top of their brackets. It’s pretty neat.

Josh: Have you been noticing the output or your recommendations being, yes, you should do Roth conversions, or more, you shouldn’t?

Matthew: I mean, it’s always client-specific. I’m kind of 50/50 so far on my clients who have said, yeah, you should do it, or no, you shouldn’t. A lot of the Roth conversion comes down to—truly, to me—not how much you’re gonna save in taxes, because what the software does is it’s really just what the rate of return of the portfolio is going to dictate how good of a deal it looks like or not. It’s really more about the wealth inheritance vehicle than anything else. So then your heirs could get that tax-free wealth.

Brent: Why do you think it’s such a big topic? I feel like so many people come to us and they’re like, oh, I gotta convert to a Roth, and they’re so passionate about it. Is it this social media push on this topic?

Josh: That was my next—yes, it is. And especially last year before the Big Beautiful Bill was passed. You saw a lot of influencers, advisors, personalities that talk about finance online saying, “You have to do Roth conversions, because if they don’t get a new deal passed to extend the tax cuts, you’ll regret it forever.”

Josh: So I feel like a lot of people and a lot of questions stem from that conversation from last year. But the tax cuts were extended. So were those Roth conversions—estimating that tax rates were gonna go up—accurate now that tax rates were extended? No. So it would just be interesting to go back on some of those projections. But yes, to agree with you, I think it’s social media.

Brent: The one thing that I’ve kind of hung onto though with conversions, and been working on with a lot of clients to help them make that decision—to me, if you’re willing to pay the tax bill by writing a check from your bank, not from the conversion, but actually physically write a check for the tax bill yourself out of your front pocket, then that’s a better consideration. But if you’re not willing to write that check to the IRS directly, you’re converting less.

Josh: You’re not gonna have too many takers with that though, because as we see, there’s not a lot of people who have that sort of comfort in post-tax dollars to write that kind of check. And to me, I just think a lot of it’s more behavioral. It’s really hard to say, I’m gonna do this for the expectation that tax rates are gonna go up in the future. I mean, yes, you can add an element of inheritance to that, but it’s hard to write that $20,000 check for that tax bill to convert.

Brent: And like we did the pod on gifting strategies and the importance of gifting and inheritance. I still think that’s not a priority to a lot of people. I agree with what you’re saying, Matt—it comes down to inheritance and maximizing inheritance really, when you get down to the nitty gritty of it. I still don’t think that many people are that highly motivated about, okay, my kids are going to inherit an additional hundred thousand of tax-free money versus taxable money.

Josh: Yeah, do you even care?

Matthew: The one projection I just did for a client was a million-dollar difference. Consistent rates of return across the board—I think I used a 6% rate of return, so it was very conservative—and it is a million dollars difference in inherited wealth for their kids.

Brent: Over how long of a period of time?

Matthew: Over the next 30 years.

Matthew: So I mean, for them, they’re probably a no-brainer. I think they’re gonna do it. It makes sense. They don’t need the money.

Brent: And I think that’s again what it comes down to. Some people are very much living off of their retirement savings. If you’re not, then that opens up that box again. But if you are, that’s a tougher conversation.

Josh: Because you’re having people reach out, clients, prospects saying, “I want to do Roth conversions,” but the affordability is not there. I think that’s a completely different question to be answered.

Brent: Yeah, and I think Roth conversions are great when they fit in that mold. It’s a perfect tool.

Josh: It’s a great tool.

Brent: It’s just social media is applying it to everybody’s tool.

Josh: Yeah, without considering all of those variables we discussed.

AI in Everyday Life

Brent: Yeah. The other thing that I think is important—over the last six months, obviously the hottest topic out there is AI and all the advancements AI is making to business and people’s lives. But I think to me, a lot of people’s perception about AI is still just, hey, it’s a tool to rewrite your email, or it’s a tool to ask questions. Matt, can you explain to people how AI is not just that—what it pertains to in so many different ways?

Josh: How much time we got? Hold on, we gotta give him a proper introduction. You are Evermont’s AI Resident.

Matthew: I just think it’s become something I’m really passionate about. When the internet came out, I was too young. I was a teenager. It was cool. I was playing on a PC, getting online to the very first websites, looking up baseball stats.

Josh: You put the CD in and load up AOL or Netscape?

Matthew: Yeah, talking to my friends on Instant Messenger. Played around with a few different websites. But it was never like a thing for me. And then the mobile boom—I don’t know how to code, so creating a mobile app was never for me. But AI is the first technological shift for my generation—let’s call it under 40—where it’s gonna make a massive impact on our daily life, and we’re at the forefront of it. We’re in the early innings still.

Matthew: But to answer your question, Brent—where this is ultimately going is AI applications are gonna start to do a lot of the day-to-day work that people have, not only in their home life, but at their work as well. Consistent tasks that are repeatable—AI can handle that.

Josh: Talk about, if you could go back—can you just do a quick summary of how fast AI went from the way we were using it, fix an email, to what you’re talking about now?

Matthew: Yeah. I think most people’s experience with AI is they heard about ChatGPT somewhere around 2023 to 2024. They tried it out. They used it like a Google search, typed in, maybe they were like, “Oh, tell me about this history,” and they got these very nice responses. Or they realized that they could create funny messages or songs with it—it’s very creative. AI’s very creative. Good at writing, did some emails.

Matthew: But really, since November, December of 2025, the advancements in the AI models—if you’re willing to pay the money for those good models—the leap to where we are today has been bigger than the ChatGPT leap from 2022 to 2025.

Brent: And those tools are basically taking tasks that you do in your everyday life or tasks that you do in your job and actually doing them for you now?

Matthew: Yeah. So for example, let’s just talk about our podcast. What I did with an AI is I created a folder and downloaded all of our podcast transcripts into it, and I gave it access to the folder on my computer and said, “This is my podcast. Please go read it and offer suggestions to make it better.” So it came back, it told me it understood. It proved to me that it understood the show. It’s like, “Brent’s the host. Matt, you’re kind of out there, edgy on technologies. Josh is the more balanced thinker.” I think that’s a pretty good description of our show.

Brent: Did it call out your Bitcoin takes?

Matthew: Yeah. No, it had all that, and it was like, “Dude, Matt is right all the time.”

Josh: You’re gonna drive people away from AI by saying that.

Matthew: But what I told it is that we haven’t done a show in a really long time, and we want to refresh our show. And so it created a brand-new outline for our show. We’re not really following it today, but in the future I see us following that more. And it takes a lot of research load off of us. So we could just come in, sit down, and record a show. Which is very valuable.

Matthew: And I think we’re gonna be at a spot pretty soon—maybe we are today, maybe in a few months—where we could just upload our show and AI will edit it for us.

Brent: Edit it, meaning clean it up, take out some of the blank time periods, or words that need to be cleaned up. If you say “you know” too many times, it’s gonna clean that all up and fix it all for you.

Josh: Yeah, because Matt was doing that before.

Matthew: Yeah. Without me doing it. And it’ll add the intro, the outro music, the disclaimer—all that stuff.

Brent: Where do you think people that listen to this show—if they’re getting close to their retirement or they’re retired, or they’re younger and planning—where are they in their everyday life if they’re not using it a lot? I think so many people are using ChatGPT for basics, but they haven’t taken that next step. Society has not taken that next step as a whole yet. What is that next step?

Matthew: Where AI is today is it’s for idea people. If you have ideas in your brain, you could talk it through with an AI and most likely get something created around that idea. For example, late last year, I started to have clients who came to me with ChatGPT-generated financial plans. These are people who I’d probably label as they would’ve been do-it-yourself investors in a previous era. They got themselves stuck in such a twisted loop where they’re like, “Hey, I need help breaking down what ChatGPT told me about my retirement plan.”

Matthew: So it’s really for people who are tinkering right now. It’s getting to a spot where you could connect your Amazon cart and say, “Hey, I need toothpaste. Load up the cart and send it to me,” and it could do all that.

Brent: Yeah. I have a feeling that in the not-so-distant future, you’re gonna talk to the AI tool, it’s gonna register, you’re probably gonna tell it your grocery list, and it’s gonna order it all for you and have it delivered. You basically have an assistant that you’re prompting what to do, and it’s gonna do all those tasks for you.

Josh: Even personally. “I want to go on a trip. Can you look up the flights and book the flights and the hotels for me? And find me the best deal.”

Matthew: We’re already there. So I took my genetic info, ran it through AI—I use Anthropic’s Claude, for people who are wondering. And it told me some things about my genetics, like things I shouldn’t be eating. I said, okay, create me a meal plan. I want to eat the same thing for breakfast, the same thing for lunch. Dinners need to be different every night. I have little kids, so it has to be kid-friendly, but I don’t wanna make two different dinners every night. And so it made me a meal plan and then created a shopping list. And the next step would’ve been go on Amazon, put it in my Whole Foods cart, and hit checkout.

Brent: Here’s how I used it. My wife needed a new car and I wanted to negotiate and make sure that I got the best deal. I called the dealership to get a salesperson, made sure that they had the exact car because I found it online. I got my live sales manager, got his number, told him to text me.

Brent: After that point, I did not talk to anybody on the phone, not one time again, until I was signing the final paperwork. Everything was negotiated through Claude. Once they said they had the car in stock, I started running all the averages against what people were getting deals on, on that specific car. I found out all the numbers—not only nationally, but locally—and so it started my negotiating process.

Brent: Every text message that I sent to them about what I wanted was generated through Claude. When they would send me a response, I would have Claude communicate with me. I got the price of the car as low as possible. I found the bottom. Then I went on to negotiate the rate. They gave me what the best rate was. I took that rate, ran it through Claude, and Claude told me where all the areas or banks are that I can easily go to get the best rate.

Brent: I went online, applied. Within two minutes, I was approved for a rate that was almost a full point less than what they were charging me. I took a snapshot of that, had Claude create me a response, sent that back to them. All of a sudden, magically the dealership was able to match the rate and actually go slightly better. So now I got the best rate nationally.

Brent: Then the third thing they want to do is upsell you on all the stuff—pre-service payments, servicing your car, you nick the rim, your tire blows out. They want to sell you six, seven, eight different service packages. So through text messages, I’m running it through Claude, looking at their numbers, analyzing what they’re gonna charge me versus the value of it. And all the numbers come back terrible. It’s not worth me paying for it. So I declined every option, but every response I gave them was literally generated by the AI system.

Brent: Ultimately at the end, I got the best price, I got the best rate, and I didn’t pay for all their upgrades. All I did was walk in there, I was in for less than 40 minutes, signed all the paperwork, and walked out.

Brent: They were almost more concerned that something was going on—like I wasn’t actually going to take the car—until I wired the money for the down payment. They were confused about how this process was going so seamlessly and I was in control the entire time.

Matthew: Yeah. We’re at a point in time where if you’re a human and you know how to use a large language model, and you’re going up against a human who is not using an AI model—the human plus the AI is gonna win every time.

Matthew: I wonder though, if in a few years if that’s gonna work, because—

Josh: Everyone’s playing on the same level playing field.

Matthew: Yeah, it’s really gonna be your AI is negotiating against the car dealership’s AI.

Brent: But then we all win, right? Because everybody right now is on an equal playing field. Knowledge-wise, I’m not a car salesman. AI is on an equal playing field with them. And I was able to be on an equal playing field where I was not going to get taken advantage of or ripped off. We now have the tools to negotiate for us.

Brent: And here’s the even crazier part—the AI tool found an error in the negotiation and in the final signing. They made a mistake by switching the county of which the car was going to be garaged at. It was the difference between San Bernardino County and LA County. And ultimately what happened was they made a mistake on the paperwork, which would’ve cost me $3,000 more in taxes.

Josh: Wow. Bye-bye car brokers.

Josh: Two use cases you just told me: efficiency, and it also saved you money. Even if you’re looking for a reason to explore this AI movement and haven’t adopted more use cases—those are two right there that are not only bringing more efficiency, but saving you money and bringing you to the same intelligence level as anyone else that you’re competing or negotiating with.

Brent: When I’ve gotten blood work done—and I know you have to be careful with medical stuff—I’ll upload that right away and have it go through a deep dive into what the results are, where my inefficiencies are, where I can become more efficient. Even some of the stuff I’ve asked the doctor about through messages—they’re literally sending an AI-generated response to me. They’re using the same tools.

Josh: Yeah, medicine’s embracing AI big time. We see that with these big medical corporations, even pharmaceutical companies. They’re all leaning into AI. Even one use case—my wife’s an ER nurse, and she was telling me that the doctors used to have scribes that would follow them in the ER to take all of their notes. The scribes are gone. AI replaced the scribes.

Matthew: So they just use a note-taker.

Josh: Correct. Same as us, right?

Matthew: Note-taking is the part that makes the most amount of sense for AI. When you explain to someone what it’s doing, they’re like, “Oh yeah, I get that use case.”

Brent: Explain to people what a note-taker does.

Matthew: They basically just record a meeting or what someone’s saying, create a transcript, and then from there you get a transcript out and it can analyze it and pull out action points. It can create a summary, recap emails. It could basically do all the follow-up work that a new college graduate would do.

Brent: I think we’re now at a point where a doctor used to—remember, they roll in their little cart with their computer on it, and they’re typing notes the entire time. There’s no reason for a doctor to be doing that anymore.

Josh: They did it, then they hired someone to do it for them, and now they don’t even need to hire someone to do it.

Brent: The thing about AI also is a lot of the feedback that I hear from people and from clients is about the fear they have with these tools, but they don’t understand the tools. A lot of what I heard on social media is, “There’s gotta be guardrails, there needs to be more guardrails,” which is extremely important. But that’s the level of what people are hearing versus what’s being applied.

Josh: Yeah. You’re only hearing about the risk, not the reward. And I think it’s just where we’re at in society. But with that being said, if you are looking at AI, there are guardrails being created. There are companies that are specifically targeting security for AI usage. We shouldn’t be only focusing on the risk because of how much reward this new technology could provide.

Matthew: I think we’ll look back in time and say AI most likely wasn’t as scary as people thought. And cell phones and social media were much, much worse for people.

Josh: But I feel like that was—even just studying and researching the internet—it scared a lot of people.

Josh: I also think that with AI, if it’s even making you nervous or you’re unsure about using it, I think it’s gonna regulate itself a little bit because it’s growing so quickly and there’s so much information that eventually—we live in a capitalistic society—it’s probably not beneficial to keep all of that information so broad and open. And then it segments and kind of regulates itself in that way.

Matthew: Yeah. I mean, we’re already at the point where most AI models know all of human knowledge and existence. Right now they’re just working on making it so they can do tasks repeatedly—which is essentially agentic work—where you could let it go work for five hours on a task and it just continually does it without human interruption.

Josh: And works in between apps and in between websites.

Brent: I think one of the biggest concerns society has now is social media and the brain rot. Getting caught up in endless amounts of Reels, stories, videos, YouTube stuff. Every generation is just wasting their brain away watching this stuff. And now you’re getting to a point where literally more of it is faker, lies, not true, than actual just pure, hey, what’s my friend from high school doing?

Matthew: Right. A lot of it’s becoming AI slop now. And it’s really hard to tell what’s true and what’s not true.

Josh: What’s real content.

Matthew: And most people—if you’re smart, you would hook up an LLM to your X account or your Facebook account or whatever your social media is of choice, and just let it go comment for you. And so then now it’s just AIs commenting. There’s a lot of people out there that call it the dead internet theory—where most of the internet is just AI LLMs talking to each other.

Brent: If you read people’s comments, whether it’s on posts, stories, or a lot of the national stuff—half of that is just bots writing it. They’re just trying to fire people up.

Josh: There was already trouble with bots. Now it’s gonna be even worse.

Brent: It’s even worse because it’s so automated, and then people are arguing with literally computers. They don’t even know it. They’re creating these opinions to just fire people up, and people are arguing with it, and there’s these big discussions.

Josh: To drive more interaction.

Brent: And all it is, is just computerized responses.

Josh: I saw something interesting with AI too. They did a study—you’d have to go back and look at the study—but the companies that are actually using AI, their employees are actually working longer. Because of how it’s motivating to do even better, learn more, work more efficiently using AI tools. I feel like we see that even with us a little bit, right? Like you’re interested—I’ve seen it a lot with you, Matt. You want to make it better, so you’re gonna continue to grind and learn and implement these new tools that AI is rolling out constantly.

Matthew: Yeah, it’s better for us. It’s easier to do your job. I can meet with more clients, I can help more families out because I have AI in the background doing tedious tasks for me that I would have to spend hours doing.

Brent: Yeah. And the ability to do it at such a high level—it’s just so efficient, so quick. It can create a spreadsheet better than probably a human. I mean, better than I can. It’s just amazing, the advancements and how technical it’s become.

Matthew: Yeah. Vibe planning—doing your planning with the AI. Create your—

Josh: It’s a 2026 word of the year here at Evermont.

Brent: What’s neat with what Matt does is you’re always pushing the bar on how we can use it, how we can apply it, what’s next with it. You’re always on top of those things, which is obviously very effective for us because as soon as you learn something cool, you’re teaching us to do it, and then we’re jumping on. To me, I mean, ChatGPT is just so far behind. I just don’t know how it actually catches up when you see some of the other tools.

Matthew: Their models are good. The thing is that the personality you get from Claude with the Opus model—it’s literally just like a human. They nailed the personality. It takes its time. It doesn’t try and spit out answers right away. It’s able to think, which is different than other models.

Josh: I’ll say this though, for anyone that hasn’t used a paid version—because now they’re testing AI models—I think the hallucinations, or the errors and mistakes from the non-paid versions of AI, are still around 50%. Meaning they’re gonna give you mistakes and wrong answers about half of the time. Compared to almost now above 90% accuracy on the paid versions of Claude and ChatGPT—only 10% hallucinations. So if you are interested, somewhat of a recommendation: definitely try a paid version versus the free version if you haven’t been impressed.

Matthew: Yeah. You have to. What they’re giving you for free is two to three years old. If that’s what you want—something that’s two to three years old—then sure, take the free version. But if you want the cutting-edge frontier models, you have to put your credit card down.

Brent: Last night as I watched the replay of the US gold medal game, I wanted to know what NHL team each USA player played on. I just typed that into chat and it gave me every player with every NHL team that they’re on. If you were trying to do that through a Google search, how long would that take you? It would take you forever. Unless there was an article that populated up. But the tools now to be able to find these things out—it’s just amazing.

Matthew: Yeah. That’s just a better Google search.

Personal Updates

Brent: All right, let’s finish out the show. As we said, we’re gonna try to pump out some really good content for everyone this year. Maybe you guys can tell listeners your Evermont recommendation for yourself, and then maybe something that’s new that’s been going on in your life.

Matthew: My daughter’s in kindergarten now, so we’ve been in the full swing of things with the school schedule. Which has been a little different, as you know, Brent—then you’re just more on the days-off schedule of the school, the same spring break schedule. It kind of changes your life a little bit. Sometimes you have to do drop-offs and pickups, so it changes your daily schedule.

Matthew: But it’s actually been nice getting used to it. I’m happy she’s in school and she’s learning a lot. We’ve been working a lot on her learning how to ride a bike, so that’s been fun. We did AYSO in the fall, so we got our toes wet with that. And yours truly was a referee.

Brent: Nice. In your yellow and black uniform?

Matthew: Yep. Yellow, black uniform, reffing. And then my son, he’s gonna be three soon. So we’re getting out of the terrible twos stage, hopefully. I think they’re both gonna do ice skating lessons, and then we’re gonna roll both of them right into AYSO in the fall.

Josh: Nice, a lot of sports.

Matthew: You have to keep them busy. Go burn that energy. You know me, I like sports.

Josh: You do. We just went to LAFC.

Matthew: Yeah. So Messi—

Josh: Just beat Inter Miami, reigning champs, three-zero.

Matthew: It was a lot of fun. Too many people there though.

Josh: A lot of people.

Matthew: 75,000.

Josh: It was fun. Doing well. Kids are growing. Daughter is just chasing her big brother. My son started T-ball, so I’m glad to put a smile on Brent’s face when I told him I was gonna sign my son up for T-ball. Brent is a big Little League guy. We had our opening day this last Saturday. It was fun. His first game’s gonna be Saturday. He’s on the Dodgers. He’s all excited.

Brent: Did you buy a Dodgers hat yet?

Josh: I’m going to. I’m just gonna go all in. We’re gonna be the Dodgers. I’m all in. I was even thinking about taking him to a Dodger game for sure. But maybe even to the new Ontario team. That’s super cool. We should go—Tower Buzzers.

Matthew: Actually Brent, the other day, Josh and I were on a walk-and-talk and we wanted to—we’re gonna do a dugout suite at the Tower Buzzers for a client event. So let’s reach out to a ticket person. And I’m just letting you know on the pod, on live air, that that’s gonna be one of our client events. Small client event.

Brent: I mean, that stadium looks great.

Josh: Yeah, I think you’d like it too. It’s baseball.

Brent: Ontario is doing amazing things. Ontario’s brilliant with the way that they run their city.

Josh: Yeah, it looks really nice. I’m excited to go. But yeah, family’s good. We’re doing good. Off to a good start. We’ve been busy here, rocking and rolling in 2026 so far. What about you, Brent?

Brent: I am in my son’s last year of Little League. He’s Little League age 12 this year, and I’ve been the president of Vineyard Little League last year and this year. I have a two-year term that I’m finishing, which will go through this summer. It’s exciting because I feel like the league is making great steps over the last couple of years. My son’s gonna be aging out. So this is a really fun stretch. I’m really looking forward to these last four or five months of coaching him and being with the kids out there.

Brent: All of this is about to kick off in the next couple of weeks. It’s gonna be such a busy stretch. But I’m embracing it and not taking it for granted, because I know once this stretch is done—as far as coaching and doing some of the things I’m doing—it’s probably on the back end. I’ll probably be done with that.

Josh: He didn’t say a hundred percent done. Did you hear that?

Matthew: Yeah. I’m just thinking about how he hasn’t mentioned that this is his final year to get to the Little League World Series and he can’t let me down.

Brent: I don’t even know if I’ll be coaching anything to do with that. But I feel like my community service has been fulfilled. I’m glad to help out the community. On the personal side, I’ve wanted to dial in my health a little bit, so I got back into Orangetheory again, which has been really helpful over the last two months. I’ve been working out nonstop—obviously as I’ve shared through the podcast, at home through Peloton and through their treadmill and strength and conditioning.

Brent: I feel like I just needed that next step. And so that has really over the last two months helped me feel like I’ve improved. Something to recommend to people if they ever want that next step—I think organized, class-structured workouts are the way to go. I’ve really enjoyed it. It’s been something that’s made me happy.

Matthew: There’s one thing I’m not doing right now, and that’s working out. But dude, I’m glad you look good. I’m glad you’re doing it.

Brent: It’s a commitment, and my kids are at different stages than yours. But when your kids are a little bit more independent, it’s easier to slip away.

Matthew: Can I give you 10 pounds?



Brent: We love to be back and creating this content, talking about important topics that are out there and things that people want to hear. I think we have some really good topics coming up and we’re great to share our opinion on those topics.

Brent: As advisors, we love helping people and that’s why we do it. If you would like more information, please visit our website at evermont.com or visit retirementplanplaybook.com for show notes. You could also call us at (909) 296-7977, and you could subscribe and leave a review on Apple Podcasts or Spotify. As always, thank you for listening.


Thank you for tuning into the retirement plan playbook. If you enjoyed today's episode and want to stay updated, please click the subscribe button for notifications on new episodes. For personalized financial guidance, or to connect with our team, you're welcome to call us at 909 296 7977, or visit www.evermont.com for a complimentary consultation. Your journey towards a successful retirement plan continues, and we are here to help every step of the way. Until next time, keep building your future. The information covered and posted represents the views and opinions of the guest, and does not necessarily represent the views or opinions of Evermont Wealth.

The content has been made available for information and educational purposes only. The content is not intended to be a substitute for professional investing advice. Always seek the advice of your financial advisor or other qualified financial service provider with any questions you may have regarding your investment planning.

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Ep. 124: Big Tax Wins, Newborn Accounts, and Why the Market’s Hitting Highs