This season’s tax strategy: invest in small business

Yahoo Finance Video

Fri, February 27, 2026 at 5:00 AM GMT+9

In this video:

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Listen and subscribe to The Big Idea with Elizabeth Gore on Apple Podcasts**, Spotify, or wherever you find your favorite podcast.**

This tax season, your investment could pay off quite literally for you and your local businesses.

In a special segment from this week’s episode of The Big Idea with Elizabeth Gore, Elizabeth is joined by H&R Block Small Business Tax Director Jody Vanarsdale to discuss how investing in small business stocks can benefit both investors and local entrepreneurs. From capital gains tax relief to supporting community businesses, Jody explains how this opportunity helps grow cash flow, strengthen P&Ls, and turn tax season into a strategic investment moment.

Yahoo Finance’s The Big Idea with Elizabeth Gore** takes you on a journey with America’s entrepreneurs as they navigate the world of small business.**

This post was written by Lauren Pokedoff

Video Transcript

00:03 Speaker A

Howdy y’all, I am so excited. I have an extra special guest today that you’re going to want to hear because you might get cash flow out of this. We are so excited to introduce Jody van Arsdale. He is the small business tax director at H&R Block. Jody, thank you so much for coming on the show.

00:26 Speaker B

Oh, thank you Elizabeth. I am excited and and delighted to be here.

00:30 Speaker A

Hey, tell me before we get too deep in the weeds why you love small business.

00:36 Speaker B

Well, um although I am the director of small business tax at H&R Block, I’ve had a handful of companies that I I’ve started with with a business partner. So I’ve been a small business entrepreneurial resource, um and and it’s very passionate. I’m so passionate about this space.

00:54 Speaker A

And is there, um is there a I mean this is like asking who of your favorite kids, but is there a type of small business that you love the most?

01:03 Speaker B

You know, I I would say yeah, when I started in the small business space, I I my business partner and I, we jumped into franchise. So we were a little afraid, right? We we wanted to know an operating model and it was a great business, but what I was passionate about is when we had an idea and we built it ground up. Like the concept of starting from nothing and taking it somewhere. Um that was so exciting. It was a little more frightening because you don’t have that kind of that operating model that’s kind of cookie cutter that says if you do X, you get Y, right? So it was a little more it was a little more um um intimidating.

01:41 Speaker A

I want to go back to um again, what tell me the benefit in buying small business stock.

01:53 Speaker B

Yeah, so there was really two benefits. Like if I think about it as Jody Van Arsdell, the the everyday person that doesn’t own a business, I can invest in my community. I can invest in the people that we’ve talked about, right? And after five years, I’m allowed to receive 100% relief on the gains of that stock.

02:22 Speaker A

Uh-huh.

02:23 Speaker B

The exciting part for me as well is the benefits to the small business community, right? It’s a way for them to increase cash flow. It’s a way for them to to go to that next operating model and and strengthen their business PNL. You know, as as we’ve talked about like cash is king, right? And and it’s hard to get to cash when you’re a small business owner, you’re worried about everything, logistics, operations, etc, etc. And so it’s a really good way to allow people to support their small business while also growing their stock portfolio.

03:00 Speaker A

There is not a business owner alive who’s not worried about cash flow. And you know, the other thing I kind of like is uh if I can have Jody, not just buying my stock, but but you advising me and being become of my being part of my small business family, right? That’s also a lot of people think of big venture or other things. And to actually get someone in my community who cares about me, they’re invested in me. I mean, it’s super exciting. Tell me about um, what are the requirements?

03:34 Speaker B

Yeah, so for the requirements, um currently through July, July 4th of 2025, you have to hold that stock for five years. It has to be a C Corporation. Their gross assets must be 50 million or less.

04:00 Speaker A

Mhm.

04:01 Speaker B

You have to be um the recipient of the original issue, which means I’m not buying it from a second party, right? I have to be an original issue from the small business. And I cannot sell back more than a de de minimus amount of my stock within two years.

04:22 Speaker A

Got it. Got it. So I like that because you you’re you’re sticking around, right? You’re helping this business owner, but then there’s just so many incentives to do this. Um and and you once owned a small business, right?

04:41 Speaker B

Yes, I did.

04:42 Speaker A

I mean, is this something that you would have cherished as a small business owner?

04:45 Speaker B

W- without a doubt. I will tell you, um, there were definitely points in times when I was borrowing from friends and family to to make payroll in some of those harder months. You know, that unfortunately for small business, you don’t just come out of the gate generating the revenue that you want to We always wish for that. access to cash was was critical along our journey.

05:12 Speaker A

Jody, why was this rule originally implemented because it’s so exciting.

05:16 Speaker B

Yeah, so it was really implemented for one, I as an investor in the small business community, it allows me to invest, infuse the small business if you will, but I also get if I meet the requirements, I get 100% relief from the capital gains. So the effectively the rise in my stock, I get to keep. So it’s a it’s a great investment.

05:43 Speaker A

Well, and it’s people literally investing in each other, right? Which is the coolest thing, right? I mean these are your coffee shops, they could be your dry cleaners, your local grocer. I mean, think about your neighbors here. It’s so exciting.

06:01 Speaker B

Yeah, I love how you said that, right? Because if you think about it, a lot of these are your neighbors who are starting a business. So you you know, you’re you’re you’re getting behind that person leading the business, but then you’re also getting an opportunity to understand the business, like what business model they’re in, and you get to help infuse that small business in your neighborhood. I love it.

06:22 Speaker A

That’s why we’re glad to have you here to explain a few really cool opportunities that have come out of the big beautiful bill.

06:30 Speaker B

Yeah, there I I would tell you the biggest thing. So as I alluded to earlier, right, the the the holding period, um one of the requirements on on the current legislation if you will, was the holding period, you had to you had to have that stock for five years, um before you could get the 100%. So it was a big ledge if you will. You had to own it for the entire five years. The new law from one big beautiful Bill Act came out and if you purchase any stock, business stock after July 4th, they’ve now done ledges, shelfs if you will. So if you hold that stock for three years and it’s seen explosion of growth, you can you can um save 50% on that capital gains if you will. Four years, it’s 75% and it’s still 100 at five years, but what that allows me to do is redeploy those gains if I want to do investments in other small businesses or whatever I’d like to do with those funds.

07:35 Speaker A

Well, Jody, I am so grateful for all this advice, um and I’m so excited that there’s this opportunity for all of us. Thank you for coming on the big idea and teaching both the business owners and the potential uh investors or acquiers how to do this.

07:54 Speaker B

Well, I appreciate the time and I um, like like I said, very passionate in this space. So I love what you’re doing and I love the segment. So thank you very much for having me.

08:05 Speaker A

Thanks, buddy.

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