Behind the Numbers: The Jason Dinesen Story

What makes someone fall in love with tax law? For IOFM’s long-time speaker and compliance expert Jason Dinesen, it’s about more than numbers: it’s about people, purpose, and the power of clear, honest education.

In this engaging episode, Jason pulls back the curtain on his career, from founding his own firm to becoming one of the most trusted voices in 1099 compliance. You’ll hear about what led him into the world of tax and accounting, what keeps him up at night in today’s shifting regulatory landscape, and why he keeps coming back to IOFM year after year.

Whether you’re deep into tax season or just curious about the people shaping financial education today, this conversation will leave you informed, inspired, and maybe even laughing.

Tune in now and meet the human side of compliance.

Jason Dinesen

Jason Dinesen, EA, is a distinguished tax professional and educator with a fervent passion for demystifying complex tax concepts. Jason is the founder of Dinesen Tax & Accounting, P.C. and Dinesen Tax Advisory, LLC in the tax and accounting world. He also is founder of Dinesen Media Ventures, which provides a diverse range of media content, ranging from continuing education programs for accountants and tax professionals, to podcast production to radio and journalism content. 

Recognized for his sharp tax interpretations, Jason is renowned for promptly analyzing the latest tax updates and IRS guidance, sharing his insights with the professional community. Over his career, he has educated more than 200,000 accounting, tax, and HR professionals on various topics. Form 1099 was the very first thing he ever taught on, on April 26th, 2012, at a Sheraton Hotel next to a Lowe's in West Des Moines, Iowa. He still teaches on 1099s and around 30 other tax topics.

Grace Chlosta
Senior Content Manager, IOFM

Grace is the Senior Content Manager at the Institute of Finance & Management (IOFM), where she has led content strategy and development since 2022. In this role, she oversees all aspects of IOFM’s digital and event-based content, ensuring it remains timely, relevant, and actionable for all financial operations professionals.

Grace manages IOFM’s robust library of site content, leads the organization’s editorial and member webinar programming, and hosts IOFM’s podcast series. She also oversees a team of subject matter experts who contribute thought leadership and educational articles. In additional, Grace curates and manages all speaker content for IOFM’s in-person and virtual events, ensuring consistency and quality across every touchpoint. With nearly three years in the role, Grace brings a deep understanding of the financial operations landscape and a passion for delivering content that empowers professionals to excel in their roles.

Transcription

Grace Chlosta: Welcome to the IOFM podcast. This is a podcast for accounts payable and accounts receivable professionals who want to stay in the know with current AP and AR trends and ideas. We'll be interviewing professionals in this space on a wide variety of subjects, including automation, artificial intelligence, career growth, compliance, leadership, and much more.

00:00:30

All right, good morning. I'm here on site at IOFM Spring with Jason. How you doing today? 

Jason Dinesen: I'm good, Grace. How are you?

Grace Chlosta: I'm doing great. You had a busy day yesterday. How was certification?

Jason Dinesen: It was good. Yeah, it's an eight-hour session on 1099s, but the thing about it always at IOFM is that the audience is always -- seriously, they're happy to be here, and they're actually really excited about these topics, and it was good discussion all day long.

Grace Chlosta: Good. And I heard we had great results, so big day, but busy and really productive and great.

00:00:59

Jason Dinesen: It was great, yeah.

Grace Chlosta: Can't ask for anything better. So we're talking to you today a little bit about you, so a little bit of a different subject. You're usually in the weeds and telling us everything we need to know about 1099 and compliance. Since you're on our screens, in our ears many times a month at IOFM, I'd love to learn just a little bit more about you, how you go into this profession, and just a little bit about your background. You don't have to start from the very beginning, but give me a little bit of an intro on kind of like how you got into the 1099 world, what you're up to, just a brief intro to start.

00:01:32

Jason Dinesen: So I started long ago. When I was a kid, I was going to be a sports broadcaster. That was my dream, like Teenage Jason, and so I went to college. I actually got a communications degree.

Grace Chlosta: Me too. Yeah.

Jason Dinesen: Actually, I didn't get into sports broadcasting, but I was a news director at a small-town radio station in Iowa, in my hometown, actually. And I did do some sports play-by-play. I've done all different sports on the local access cable channel.

Grace Chlosta: I love it.

00:02:10

Jason Dinesen: That's actually a big thing in those small towns. You do the high school games and stuff. And so I did that. I'm quite a bit older than you, so that was '90s, 2000s. And eventually started thinking about the future and like, what else can I do? I always had a love of numbers and statistics, and so then it's like, I'm going to become an accountant.

Grace Chlosta: Usually those things aren't mutually -- usually -- for me, personally, as a communications major, I really hated numbers and statistics, so the fact that you could match them up and find a common ground is pretty impressive.

00:02:49

Jason Dinesen: Exactly. I went back to school, got an accounting certificate, and then became an enrolled agent, which I still am, and started preparing tax returns.

My 1099 life, I guess, started in 2012. I went back and looked. April 26^th of 2012 I was a co-presenter at an all-day seminar at a Sheraton Hotel, next to a Lowe's, in West Des Moines, Iowa.

Grace Chlosta: Wow. You've come a long way.

Jason Dinesen: I've come a long way. And, you know, that session I don't know was very good. I was very young in my career and had no expertise in 1099s at all. I was just someone gullible who said yes to this place that was calling around -- literally going down a list -- until they found enough accountants to come fill the time. But it got my foot in the door, and I've been teaching on -- I have about 30 different topics I present on, but 1099 -- anything related to that is what people have always come back to, and that's how you found me a couple of years ago.

00:03:59

Grace Chlosta: I was going to say, do you even remember how we all connected, at this point?

Jason Dinesen: I think you were looking for just more voices and you kind of stumbled across me and you just reached out in an email. And I responded to you, and here we are.

Grace Chlosta: Here we are, two years later. It's funny. We [are] always -- I've said this a million times, but looking for more speakers. It's really hard to find folks who have the subject matter expertise in 1099 and compliance, who are also willing to speak about the topic, because it's pretty intense. You have to know your stuff inside and out. Do you ever feel intimidated by this whole world? How do you feel presenting this topic in front of so many people?

00:04:43

Jason Dinesen: I don't know that I ever get intimidated in the presenting, but "Ask the Experts" -- I don't know if "intimidate" is the right word, but sometimes those questions that people ask, it's like, wow, this is hard.

Grace Chlosta: You're digging deep, trying to find -- I can understand, absolutely. I mean, now I feel like, when we're not on site -- probably the biggest part of your impact on IOFM. So if you didn't know, Jason is the one, when I say on those articles "our third-party tax expert," that's Jason. So he is answering dozens a week. Any one specifically that's ever stumped you? Or can you think of anything off the top of -- any weird, random, funny stories from IOFM so far?

Jason Dinesen: There's just these questions that come in about things that I have never even thought of. There's one that I'm still working on a response to that involves tax treaties with other countries. It's like this place in another country is doing something, but there's a server over here in VA, or something.

Grace Chlosta: Oh, my gosh.

Jason Dinesen: And it's like, you're digging into --

Grace Chlosta: And you're like, no wonder you need an expert, because I need an expert. [laughter]

Jason Dinesen: I need an expert, exactly.

Grace Chlosta: And do you find with these questions, too, that you're really kind of expanding your own knowledge and it's helping you even grow your career a little bit, like in your own knowledge with compliance?

00:06:04

Jason Dinesen: Yes. Just in the first five months of this year on "Ask the Experts," there have been certain things where it's like, "Oh, I didn't realize that." And I aways say, especially in the eight-hour certification course, "This stuff is hard. And people call me the 'expert,' but I learn new things." So it's not so much that you have to know all the answers to everything, like if you get certified. It's [that] you know how to find the answer, and you also -- the more you do this stuff, the more that things stick in your mind of, "Hey, wait a minute. We need to look this up also and see if that applies."

Grace Chlosta: Absolutely, because we have so many resources. We talk about the Master Guides all the time -- such a massive textbook, right? Like, what do I even look up to find my answer? So that can be huge and a huge resource that I know you're working on. Come summertime, we're going to be updating those. That's a big part of it, too.

00:07:01

So tell me a little bit. We're on site. What are you talking about in the next couple of days? What do you have going on? 

Jason Dinesen: Yeah, so as we record this on Tuesday, I am teaching on W-9s this afternoon and then an "Ask the Experts" session, kind of a recap of some of the top questions.

Grace Chlosta: Amazing.

Jason Dinesen: Yeah. And then tomorrow is just kind of a generic update course and then a long course on contractor versus employee, which I believe we're also going -- that, I think, is going to be our June webinar also.

Grace Chlosta: It is, yes. We should be posting that in the next couple of days here for our website, but yeah. That's going to be a long session, an hour and a half, right, on Wednesday afternoon?

Jason Dinesen: Yeah.

Grace Chlosta: We love those deep dives for folks who weren't able to come to the preconference day to still be able to get the long-form content. That's awesome. You're working so hard here. You're running around like crazy.

00:07:53

One thing I'd love to ask is: You're in these sessions. It's really dry. The topics are really complex. How do you find a way to make them approachable or even fun? What kind of questions and feedback are you getting from the attendees after your session? 

Jason Dinesen: Well, I almost (seriously) have groupies.

Grace Chlosta: You do.

Jason Dinesen: You know that. There's people who seriously --

Grace Chlosta: We want to make T-shirts.

Jason Dinesen: That's right. We should make T-shirts. There's people who go to every 1099 session that I give. At heart, I'm kind of an introvert, really.

Grace Chlosta: Me, too. Right.

Jason Dinesen: But if you sit me down with something like a microphone in front of me, or I'm standing up in front of an audience, I can put on a show for folks. That's kind of how I view when I present is that I'm not just going to read the slides word for word. In fact, a lot of times, I'll flip to a slide and I won't even actually read the words on the slide. I just kind of talk.

00:08:46

Grace Chlosta: Right. That's the best way to do it. If you can use your little bullet points -- it's the worst sometimes attending a presentation and they're just reading from the slide deck and you're like, "I could've just done this at home. I could've just ready it myself," right? You want to give them tidbits, make it fun and informational, and go from there.

Jason Dinesen: And I try to work stories in. I try to be as funny as you can be. A lot of my humor is kind of dad-joke-level humor, but, you know, it's just something to make it so that it's not so dry, like you said.

Grace Chlosta: A lot of these folks come to these events to learn about the newest updates in 1099. So they're attending your sessions. Like you said, you have groupies. WE need T-shirts.

Jason Dinesen: Right. I had a guy come up to me yesterday who was a student and he said, "You don't know me, but I know you. I follow all of your stuff at IOFM, and I love what you're doing."

Grace Chlosta: I love that. A little creepy -- no, I'm just kidding. [laughter] Like, you need a little Jason pin or something. That's so fun. Well, aside… One of my favorite fun facts to close this out (about Jason) is your current adventure with your family, which we've never really talked about on IOFM, so tell me a little bit about what you guys are up to.

00:09:55

Jason Dinesen: Yeah, well, a couple of years ago, we moved to Portugal, if you could believe that, and that's something that my wife and I had talked -- well, it's a really long story, but she has a background in the country of Spain, which is not Portugal, but we had talked, way back when we first met, that someday we'll retire in Spain. And then COVID happened and we started just kind of -- like a lot of people, we started questioning what we were doing and why we were doing it, and we were like, "Let's go on an adventure." I may be an introvert, but I have that side of me that's kind of like, "Let's do it."

Grace Chlosta: Sure, yeah, absolutely.

Jason Dinesen: You even see that, Grace, where sometimes I'll send you emails where it's like, "Hey, maybe we should do this."

Grace Chlosta: I love that. That's the best. Just keep growing. It's the best way to do things. You're never going to know until you try. More than half the time, things end up working out, right?

00:10:53

Jason Dinesen: Yeah. So we did it. We moved to Portugal. We've been living in -- we're not living in a million-dollar mansion on the Mediterranean. We live in a town of 12,000 people, inland, in Northern Portugal. Our kids go to Portuguese public school. We live in a 1,000-square-foot apartment.

Grace Chlosta: But what a great experience for you guys and for your children. That's incredible.

Jason Dinesen: Yeah.

Grace Chlosta: How do they enjoy the schools, and how do they like everything?

Jason Dinesen: They actually have fit in quite well. There have been some challenges [with] learning the language and such, but they've been embraced by their classmates, so it's been good for them.

Grace Chlosta: That's amazing. Do you think you're going to end up staying there for a long time, forever?

Jason Dinesen: Our plan is to stay there for as long as we can.

Grace Chlosta: That's amazing. That's so cool. And selfishly, I love this because Jason brought us some goodies for our staff office.

Jason Dinesen: I did, yes. Portuguese candy.

Grace Chlosta: And we're all so excited. I hid it from everyone because I need to get my hands on it first. [chuckles] Thank you so much, Jason. This was such a great conversation. So happy to have you, always, here with us at IOFM. I will let you take a little break before your busy afternoon, I'm sure.

00:12:00

Jason Dinesen: All right, very good. Well, I'm pleased to join you. I know we'll be talking again.

Grace Chlosta: Oh, we will. Thank you so much.

Thank you so much for listening to the IOFM podcast. Remember to head on over to the Member Forum to discuss today's episode and provide ideas for our next one. And to stay up to date on IOFM's current events, both in-person and virtually, head on over to IOFM.com.

Continuing Education Credits available:

Receive 1 CEU per hour of listening time towards IOFM programs:

Receive 1 CEU per hour of listening time towards maintaining any AP and P2P related program through IOFM! These programs are designed to establish standards for the profession and recognize accounts payable and procure-to-pay professionals who, by possessing related work experience and passing a comprehensive exam, have met stringent requirements for mastering the financial operations body of knowledge.

Continuing Education Credits available:

Receive 1 CEU per hour of listening time towards IOFM programs:

Receive 1 CEU per hour of listening time towards maintaining any AP and P2P related program through IOFM! These programs are designed to establish standards for the profession and recognize accounts payable and procure-to-pay professionals who, by possessing related work experience and passing a comprehensive exam, have met stringent requirements for mastering the financial operations body of knowledge.