Teaching Tax Flow: The Podcast

In Episode 166 of the Teaching Tax Flow Podcast, hosts Chris Picciurro, CPA and John Tripolsky break down the often-overlooked Secure 2.0 Act and explain why it plays a critical role in retirement and tax planning—even if it doesn’t get the same headlines as the Tax Cuts and Jobs Act or the OB3 Act.

Dubbed the “middle child” of tax legislation, Secure 2.0 introduces sweeping retirement changes beginning in 2025. Chris and John walk listeners through how these updates affect business owners, employees, and taxpayers approaching retirement age. From automatic enrollment requirements to expanded catch-up contributions, this episode highlights how Congress is actively nudging Americans toward better retirement behavior.

With relatable analogies, practical examples, and Chris’s personal milestone of turning 50, this episode turns complex legislation into actionable planning insight—helping listeners understand not just what changed, but how to use it strategically.

Key Takeaways:
  • The Secure 2.0 Act modernizes retirement planning rules and fills the gap between major tax reforms.
  • Taxpayers ages 60–63 gain access to enhanced catch-up contribution opportunities.
  • Beginning in 2025, most new 401k and 403b plans must include automatic employee enrollment.
  • Long-term part-time workers benefit from expanded retirement plan eligibility.
  • The introduction of PLESSA accounts allows limited penalty-free access to retirement funds.

Episode Sponsor:
REPStracker
www.repstracker.com/affiliate/teachingtaxflow (CODE: IFG)
  • (00:01) - Exploring the Secure 2.0 Act and Its Impact on Retirement
  • (05:25) - Turning 50 Brings New Tax Benefits and Pickleball Opportunities
  • (08:25) - Age, Music Preferences, and Tax Topics Discussed
  • (09:49) - Secure 2.0 Act: Enhancing Retirement Plans and Accessibility
  • (16:06) - Making Tax Planning Accessible for All Income Levels

Creators and Guests

Host
Chris Picciurro
Founder, Teaching Tax Flow
Host
John Tripolsky
VP of Marketing, Teaching Tax Flow

What is Teaching Tax Flow: The Podcast?

Welcome to “Teaching Tax Flow: The Podcast”, the show that’s all about demystifying taxes and helping you keep more of your hard-earned income in your pocket.

Hosted by tax experts from the Teaching Tax Flow team, this unfiltered (but clean) podcast is designed to empower you with the knowledge and tools you need to confidently navigate the world of taxes. We’ll cover everything from understanding tax laws and regulations to maximizing deductions and credits.

In each episode, we’ll break down a specific tax-related topic in a clear and accessible way, providing practical tips and strategies you can use to optimize your tax situation. We’ll also answer listener questions, share the mic with amazing guests, and share real-world examples to help illustrate key concepts.

Whether you’re a freelancer, small business owner, real estate investor, or just looking to understand your taxes better, this podcast is for you. So tune in, take notes, and start building your confidence in taxes today.

Produced and hosted by Teaching Tax Flow.
www.TeachingTaxFlow.com

John Tripolsky:

Hey, everybody. Welcome back to the Teaching Tax Flow podcast episode 166. Doing things a little bit different because we know you listen to every single one of these episodes. But today, we're gonna talk about the secure two point o act. So if you haven't met me, I probably haven't met you yet.

John Tripolsky:

John Trepolski from the Teaching Tax Flow team, and I am joined here by my esteemed cohost, Chris Pacquero. How's it going, Chris?

Chris Picciurro, CPA:

It's going well. How are you doing today?

John Tripolsky:

Doing good, man. I'm excited to jump into this one because I think we can I wouldn't say debunk something, but when we talk about secure two point o or the secure two point o act, secure actually stands for something? Right? It's kind of an elongated abbreviation acronym or something. Right?

John Tripolsky:

What are we looking at here?

Chris Picciurro, CPA:

What does this mean? So the secure two secure act of 2019 was the OG secure act. It stands for setting every community up for retirement enhancement. So remember, one of the laws of teaching tax flow, that tax agencies are your involuntary business partner. Tax laws are written to encourage and discourage financial, social, and economic behavior.

Chris Picciurro, CPA:

One of which is the government wants to encourage taxpayers to save for their own retirement because of it because the strain that's been put on to our Social Security and Medicare system due to our aging population and people are living longer. So there was a secure act of 2019, the secure two point o act came into the fray, in 2022. And we're gonna talk about now even though that act was was signed in the law in 2022, a lot of the provisions affect the 2025 tax year and a lot of what, you know, I just came off being on the road. I had the honor of of teaching one more time tax season updates to tax professionals for continuing ed, and we talked about the secure two point o act. I described the secure two point o act as the middle child act.

Chris Picciurro, CPA:

So if you are listening or to this, and you you will and you have a middle child, you probably are gonna chuckle. If you're watching on our YouTube, I want you to comment right now if you have a middle child or if you are a middle child. I'd love to hear about that because most middle children most middle children like to get attention and they sometimes they feel lost. You know, you've got the Tax Cuts and Jobs Act of 2017. That's like the older child.

Chris Picciurro, CPA:

You've got OB three, one big beautiful bill act. That's the younger child. That's that's the one that everyone think thinks is cute and, like, to your tax cuts, the oldest child's usually the one that's the rule follower. And then you have that middle child that that's always saying, hey. Look at me.

Chris Picciurro, CPA:

Remember me? Give me some attention even if it's not always the best attention. And, you know, you know, if you're a middle child or have one, you know what that means. So the security point o act is kinda like that tax act that said, hey. Remember me?

Chris Picciurro, CPA:

I know I've got overshadowed by Tax Cuts and Jobs Act and OB three, but I'm important, and there's a lot of things that are changing here in 2025 or that have changed, and and that could affect actually end of year tax planning implementations based on this act. So, yeah, we're gonna dive into some of the changes that affected 2025 under the secure two point o act, which, again, I believe it was in December, December 29. Oh, a day after my wedding anniversary of 2022.

John Tripolsky:

Awesome. And, yeah, we'll we'll dive into this here. And, yeah, Chris, on what you said. I think if anybody has any questions on this, I mean, again, we're kinda just scratching the surface. Drop some comments in there.

John Tripolsky:

Even if you're not watching this on YouTube, you can get on YouTube with a couple clicks. We'll put some links in the show notes. Get on there and comment back. I mean, we do do a lot of corresponding back and forth with people. So as we get into this one Chris, I love that you explain that, where that came up with or why you call it the middle child.

John Tripolsky:

Right? Because I would agree a 100%. The one big beautiful bill actor, OB three or OB three a, regardless of what people are calling this thing, that one's getting all the attention right now, I think. Right? That that's the newborn baby that everybody wants to hold and and get used to.

John Tripolsky:

So let's, let's discuss this secure two point o or secure act a little bit more.

Ad Read:

This podcast is sponsored by Reps Tracker. Are you a real estate investor who is bogged down with the huge tax burden? Real estate investing can open the door to powerful tax benefits. Reps Tracker can streamline the process of accelerating these opportunities. To take advantage of a special TTF community discount, go to teachingtaxflow.com backslash reps, r e p s, and use the code I f g.

Ad Read:

Better yet, click on the link below in this episode's show notes to go directly to the reps tracker sign up page.

Chris Picciurro, CPA:

Well, some one of the things that occurred this year, and you know if I'm playing pickleball oh, by the way, if you play pickleball, yeah, drop in the comments. I wanna hear from you. I can't tell you. I've had the pleasure of speaking with people in the teaching tax law community recently as I work in our private CPA firm, and they they realized that I do like pickleball. So we talk a little shop sometimes, talk some paddles, talk some venues, and I got to actually, I got to go out and play in Florida when I was there in Jacksonville on my on my last taxis and update runs.

Chris Picciurro, CPA:

I got to go to the very cold Queens, New York and then to Jacksonville. And in both places, I said, hey. I had a big year this year. When I'm playing pickleball, the score is seven five, I always say, hey. Good year.

Chris Picciurro, CPA:

First of all, I'm happy that I'm winning, but the because the score is seven five, but that was my birth year, meaning I turned 50. So turning 50 in the tax code when it comes to the tax code means that I can do the Heinz retirement contributions. You might say, what the heck are you? Is Heinz ketchup a sponsor? You should be, but the you get the ketchup contribution.

Chris Picciurro, CPA:

So people that are over 50 years old can make an additional contribution to their retirement account. So I just call it the Heinz ketchup instead of just ketchup. And but what happened is oh, by the way, turning 50 comes with other benefits. One, I can now stroll through, what you affectionately call Wally World or Walmart. I found out there are no Walmart.

Chris Picciurro, CPA:

Jen, there aren't Walmarts in New York City. Because and, an attendee came up and said, you know why? Because New York City is a union shop town, and Wally World doesn't employ union workers. I said, okay. So if you're scrolling running around Wally World or one of your major grocery stores and you take a one a day vitamin, I now have the pleasure of buying Centrum Silver.

Chris Picciurro, CPA:

So this is a big graduation, for the common person like myself. So Centrum Silver and I can compete in those 50 or senior pickleball tournaments and do the Heinz ketchup contribution. So those are all the benefits of turning 50. But guess what? The middle child act or secure two point o act said, hey.

Chris Picciurro, CPA:

We're gonna reward people for turning 60. 60 is the new 50. Right? That's what I heard, I guess. So, starting in 2025, we have enhanced Heinz retirement plan contributions or enhanced catch up contributions for anyone ages 60 to 63.

Chris Picciurro, CPA:

So for the ten twenty twenty five year, if you are 60 to 63 years old, you can make larger retirement contributions in your four zero one k or four zero three b or four fifty seven plan, and those are significant. They're a 150% of your regular catch up contribution. That's it's quite a so and and then the thought was, well, this is interesting. Why is it just ages 60 to 63? And I don't I couldn't figure out why.

Chris Picciurro, CPA:

A couple attendees in the courses said, you know what? Since the the, full retirement age for Social Security increased by a few years, maybe the federal government thought, okay. Well, let's then give people extra three years to make larger IRA or rather IRA four zero one k, four zero three b retirement plan contribution. So very interesting. So the point is is if you are, contributing your four zero one k and you typically just max your your, employee contribution, you will notice that you put more in this year than you've ever been able to put in in previous years.

Chris Picciurro, CPA:

So there's there's that. So it's pretty interesting that that that there's just foot that's just for the age 60 63 taxpayers. But guess what? 60 is the new thing. John, I've heard you had a big birthday this year.

Chris Picciurro, CPA:

Yeah. I'll always I'll always be behind you. I'll start. So what else I've heard is 40 is the new 30, so congratulations.

John Tripolsky:

That's you know what? That's that's what they say. And and apparently, according to Spotify in my year wrap up, my listening age is 19. So I don't know if I

Chris Picciurro, CPA:

get Mine was 28. So I don't know

John Tripolsky:

if it's, like, too much Taylor Swift going on there or what what's going on, but, you know, something.

Chris Picciurro, CPA:

We haven't talked about you being a huge Swiftie in quite a few episodes, probably over a year, but that that's alright. Maybe we'll revisit that next year. You know, Taylor's kinda washed as the kids like to say. Right? She's although she had a new album, but, you know, what what are you gonna do?

Chris Picciurro, CPA:

I I she's got other things going on. She's, you know, dating football players or getting married Tom, and that sort of stuff.

John Tripolsky:

Yep. Lot lots of activity. Kind of in the similar to the tax world. Right? I mean, we got we there's so much stuff going on.

John Tripolsky:

I think it's it's important that we do topics like this, right, and dive in on on something that's a little bit more specific that some people kinda tend to forget about because right there, everybody kind of gravitates to the new exciting news that's gonna impact them now, not necessarily what's gonna impact them in the future. So, again, I I love that you refer to this too as the middle child. Right? Like, know

Chris Picciurro, CPA:

the exist.

John Tripolsky:

Don't you? You forget about it sometimes. So it's a So It's a it's a good thing.

Chris Picciurro, CPA:

Exactly. And we don't know if Taylor's a middle child. She does have some catchy tunes. Alright. Let's talk about the next thing with Secure two point o is mandatory automatic enrollment in new 401K and 403B plan.

Chris Picciurro, CPA:

So this is interesting. Right? Now if you have a new plan in 2025, either a four zero one k or four zero three b, employers have to automatically enroll eligible employees, which is really interesting because before, you know, before an employee might forget that they're eligible or not be notified, not really understand they're eligible. So employees must now the employee can opt out at any time, but I think, you know, this is obviously a provision that's that's not just encouraging people to contribute to retirement. It's enrolling them in their retirement and saying, you can opt out.

Chris Picciurro, CPA:

So this is like the bonus depreciation of of retirement. You got it, but you get a lot out of it. There are businesses, smaller businesses with less than 10 employees, new businesses that are less than three years old, some churches and government plans that are exempt. But for the most part, new four zero one k and four zero three b plans. If you're eligible, guess what?

Chris Picciurro, CPA:

You're in the plan, and then you can you can elect out if you want. So congratulations.

John Tripolsky:

It's a great way. I mean, if they're trying to accomplish that, right, of trying to, eliminate the, I don't know, ignorance is bliss or or or anything like that, like, you can't by by that being the case, you can't say, oh, I wish I would have did this a while ago. Like, you have to make a conscious effort to say, no. I don't want this. Right?

John Tripolsky:

So they're making it I mean, in my opinion, I think it's it's pretty good. You know? Mhmm. I think it's a smart move for the most part.

Chris Picciurro, CPA:

Well, we know if you don't see it, you can't spend it. So it's probably better for new to you know, especially younger people to contribute to retirement, coming have it come right out of their paycheck. Now, again, we wanna encourage you. Remember, legally and ethically reduce the tax you're paying your lifetime. So if you're not if you're in a lower to moderate income household, really focus on working with your tax professional and financial adviser to determine if you should be a contributor to a Roth or a traditional retirement account.

Chris Picciurro, CPA:

And and again, you might have questions. So like John said, post any questions right in our YouTube chat. We go through a little behind the curtain. We go through a multiple times per week and answer questions and and and some that ending within our private Facebook group, which is defeatingtaxes,defeatingtaxes.com. We're we're answering questions all all week long, but we love it Because here's what happens.

Chris Picciurro, CPA:

Those questions drive our content. So And, Chris, maybe maybe we

John Tripolsky:

can have some fun with this next year and really put you in the hot seat. Maybe maybe if somebody comments the most and we start to identify some trends of, you know, somebody really being active, maybe we'll let them come on a podcast with us and just grill you on some stuff.

Chris Picciurro, CPA:

Probably not, but maybe. You never know. Number three. Law so what do we have? So a reduced We have two more provisions.

Chris Picciurro, CPA:

There's a there's a new concept called the long term part time worker, LTPT. Oh gosh. Another another acronym. Ultimately, we there were people that were excluded from an employer sponsored retirement plan that were long time and yet part time workers. So let's think about that person that works maybe as a as a seasonal team member at as a full time person for half the year.

Chris Picciurro, CPA:

Maybe they're at a golf course. Maybe they're a lifeguard. Maybe they work during the holiday season. So if you are a long time part long term part time employee or worker, you could be eligible for a retirement plan now where you wouldn't before. You just have to work at least five hundred hours per year for two consecutive years to be eligible, which which would make sense.

Chris Picciurro, CPA:

I mean, what if you were you could easily do that if you were working a holiday season for twelve weeks full time. So that is that's really, I think, gonna help those long term part time workers. And and it's important because remember, usually four zero one k's and four four four three b's and employer sponsored plans come with a match. Then you wanna pick up that match. At least put money in there to to pick up your employer match.

Chris Picciurro, CPA:

The fourth and final secure two point o act provision that we're gonna talk about is another acronym. Now, John, you've been slacking. You wanna throw me under the bus. I'm gonna throw you under the bus now. You had a little jingle.

Chris Picciurro, CPA:

You had a little you had some some fancy pants stuff going on when we had an acronym, and I I

John Tripolsky:

get like a cowbell. Yeah. I like the the the SNL skit.

Chris Picciurro, CPA:

And I didn't hear that little that little jingle. So I'm I'm expecting it by for this one. But a new one called a Plessa, pension linked emergency savings account. So this is something where an employer can, may offer a a savings account linked to their defined contribution plan, meaning their retirement plan contributions. They're made after tax like a Roth.

Chris Picciurro, CPA:

They're only they're capped at $2,500 with their index for inflation, and you can withdraw up to five times per year penalty free. The reason this is in play is for lower to moderate income households, that have employer match money in the retirement account. Instead of taking a distribution, which is taxable, which is and subject to a 10% penalty, it allows people to in in those situations that have an emergency to be able to take a withdrawal without the 10% penalty. So it it again, we're we're seeing you know, they have to have a hardship. But what are we seeing here with these last two?

Chris Picciurro, CPA:

We're seeing the theme of, hey. Let's make retirement plans available for maybe moderate and and lower income households, people that don't work part time. And then the first couple, let's let's make actually, the last three and the automatic enrollment. And then the first one, let's increase the amount that taxpayers could put into retirement in those typically preretirement years of 60 to 63. So that's your summary.

Chris Picciurro, CPA:

Secure two point o, the 2025 provisions. And guess what? There's gonna be some new stuff in '26 and '27. We're gonna talk about either on our podcast or or on our on the teaching cash flow YouTube channel in the future.

John Tripolsky:

I like it. I like it. So, hopefully, if if somebody was aware of this, we dove a little

Chris Picciurro, CPA:

bit deeper. Of course, there's

John Tripolsky:

a lot more to go into on how things connect. And and, Chris, I would say this, and I'll with this exactly. Right? As we're talking about, you know, this this middle child act. Right?

John Tripolsky:

There's a lot of things here that are are I wouldn't say forcing people to plan for the future, but they're again, they're putting the the effort on them to opt out, not opt in, which I think is fantastic. And the greatest thing about this is is it's it correlates, I think, directly with the way that we always talk about tax planning. Right? Like, our job at teaching tax while we're talking about tax planning, we wanna make it accessible to as many people as possible, even low to middle income families, household types of businesses, all this stuff. And I think this is kinda going in the same way.

John Tripolsky:

So if anything, it kinda solidifies the trend of trying to take things that people think is only up here, you know, if you're making a million plus or whatever and making it more accessible. So I'll kinda leave it at that. Look forward to next episode with everybody again. Different day of the month, same day of the week, completely different topic here on the teaching tax flow podcast. Have a great week, everybody.

Disclaimer:

The content provided is for educational purposes only. We encourage you to seek personalized investment advice from your financial professional. For all tax and legal advice, please consult your CPA or attorney. Investment advisory services are offered through Cabin Advisors, a registered investment advisor. Securities are offered through Cabin Securities, a registered broker dealer.

Disclaimer:

The content of this podcast does not constitute an offer of securities. Offerings can only be made through an offering memorandum, and you should carefully examine the risk factors and other information contained in the memorandum.