Shows
The Next Tour podcastEpisode 26 – Transition Decision: Part 2In this episode of The Next Tour, Ian and Andia meet with Jason Medsger to follow up on his transition journey, first highlighted in Episode 4. Almost a year ago, Jason was contemplating the retirement decision and preparing to “push the button” to apply for retirement.Now that he has an approved retirement date, we revisit the questions we asked the first time around, such as what gives him anxiety ahead of closing this chapter in his life, what his career exploration journey has looked like thus far, and the impacts of transition on the family now that a re...
2025-12-0131 min
Accounting in the WildW-9, 1099-K, and the Tax Benefit Rule: What Every Accountant Should Know (Fall 2025 Update)In this episode, Jason Dinesen breaks down three big updates affecting accountants, tax preparers, and small business owners in Fall 2025:🔹 1. Draft W-9 ChangesThe IRS has released a draft of Form W-9 that could significantly change how sole proprietors and single-member LLCs report their Taxpayer Identification Numbers. Jason explains:What’s in the draft (and what’s not official yet)Why sole proprietors might soon be required to use their Social Security NumberHow to keep tabs on the official IRS W-9 page for updates🔹 2. 1099-K Thresholds and the “B...
2025-10-1725 minAccounting in the WildOvertime Deduction, Trump Accounts & 1099 E-Filing — Big Beautiful Bill UpdatesJason’s back with a grab bag of timely tax and accounting updates pulled straight from his teaching sessions and client questions.In this episode of Accounting in the Wild, you’ll hear about:Big Beautiful Bill (BBB) — the brand-new overtime pay deduction, how “qualifying overtime” is defined under the Fair Labor Standards Act, and why W-2s aren’t changing in 2025 (but employers still have new reporting duties).Trump Accounts — what they are, how they work, and the unanswered questions around the $2,500 employer contribution rule.Electronic filing of 1099s — the difference b...
2025-08-1227 minAccounting in the WildSummertime Tax Moves, Expiring Credits, and That Big Beautiful BillIt’s summertime... but there’s still tax planning to do.In this solo episode of Accounting in the Wild, Jason Dinesen breaks down what tax professionals (and taxpayers!) need to know right now — before key deadlines and credits disappear.In this episode:⚡ Energy credits are going away — EV, solar, appliances, and more✉️ IRS will no longer accept paper checks after September 30🏕️ Day camps and the daycare credit: what counts?💸 Overtime and tip deductions — where do they go on the return?🚗 Also the new deduction for certain car loan interest deduction -- where does it go?🧾 Written...
2025-07-2925 minAccounting in the WildData Security for Accountants, with Nick Mullen of Entoo SecurityIn this episode of Accounting in the Wild, Jason welcomes Nick Mullen, Chief Advisor at Entoo Security, for a critical conversation about cybersecurity for tax pros and accounting firms.***DISCOUNT*** Mention Accounting in the Wild when you sign up for services with Entoo Security and they'll give you a 50% discount on your onboarding fees!Topics:Why “just don’t click the link” isn’t real protectionHow hackers use DocuSign, QuickBooks, and even deepfakes to target small firmsWhy antivirus is no longer enoughMFA: what works, what doesn’t, and how criminals get around itHow to s...
2025-07-1543 min
The IOFM PodcastBehind the Numbers: The Jason Dinesen StoryWhat 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.
2025-07-0212 minAccounting in the WildUnlocking Tax Savings: Cost Segregation and Section 179DIn this episode of Accounting in the Wild, Jason is joined once again by Randy Eickhoff of Acena Consulting for a real-world discussion on two powerful tax strategies for real estate investors and building designers: cost segregation and the Section 179D deduction.They explore:What Section 179D is and who qualifiesHow cost segregation works and when it makes senseIRS audit considerations and Form 3115 catch-up strategiesThe surprising connection between 179D, cost seg, and the R&D creditWhy these strategies are about more than just tax savings—they’re cash flow toolsWhether you...
2025-07-0130 minAccounting in the WildThe Big Beautiful Bill: Major 1099 Reporting Changes Explained (Plus an Update on the IRS FIRE System)In this solo episode, Jason Dinesen dives into the proposed 1099-related changes in the so-called Big Beautiful Bill. From raising the reporting threshold to resetting Form 1099-K rules, this episode covers what’s really in the legislation—and what it means for you.Topics covered:Proposal to raise the $600 threshold to $2,000 starting in 2026Return of the 200 transaction / $20,000 rule for Form 1099-KNew reporting form for auto loan interestThe planned phase-out of the FIRE system by December 20261099 history trivia to impress your tax friendsWhether you're an a...
2025-06-1726 minAccounting in the WildCompliance to Advisory: Mike Grinberg on Building a Purpose-Driven FirmIn this episode, we explore how to build a business that truly works for you — not the other way around. Mike Grinberg, a growth consultant for professional services firms, shares his insights on:✅ Defining your owner’s intent – why you need to be crystal clear about what you want from your business✅ Moving from transactional work to high-value advisory – how to make the leap and deliver real impact✅ Using frameworks and methodologies as your unique IP – how to stand out and charge premium rates🔑 Key takeaway: It’s not just about making money. It’s about building a...
2025-06-0352 minAccounting in the WildWhat Is IOFM? Inside the Must-Have Resource for AP & AR ProsJoin host Jason Dinesen live from the IOFM Spring Conference in Orlando as he sits down with Jess Scheer, Executive Editor at the Institute of Finance & Management (IOFM), to explore why IOFM is the go-to resource for Accounts Payable, Accounts Receivable, and financial operations professionals.🎧 In this episode:What IOFM is and who it servesThe power of the "Ask the Expert" feature (and how Jason fits in!)Certifications for AP, AR, and 1099 professionalsThe value of benchmarking and performance dataUpcoming IOFM events and how to attendWhy IOFM membership often pays for itself—fastWhe...
2025-05-2011 minAccounting in the WildExit Planning with Herb Cogliano: Strategy, Leadership, and the Accountant’s RoleExit planning isn’t just for business owners nearing retirement. It’s a proactive strategy that strengthens your business today, while preparing you for a successful transition in the future — whether that’s selling, passing it on, or scaling down.In this episode of the Accounting in the Wild podcast, Herb Cogliano of Aspire Growth Advisors joins us to break down why exit planning should be top-of-mind for all business owners — no matter their current stage.Guest Bio:Herb Cogliano is the founder of Aspire Growth Advisors and a Scaling Up Certified...
2025-05-0635 min
The IOFM PodcastMastering Payment Reporting: Why CPRS Certification Matters with Jason DinesenStaying compliant with payment reporting regulations is more critical than ever – so how can finance professionals ensure they have the knowledge and skills to do it right? In this episode, IOFM Content Manager Grace Chlosta sits down with returning guest and expert trainer Jason Dinesen to discuss the Certified Payment Reporting Specialist (CPRS) certification. Jason breaks down why this certification is essential for finance professionals, what attendees can expect from the CPRS training at the upcoming IOFM Spring Conference & Expo, and how certification can enhance career growth and organizational compliance. Whether you're considering certification or just looking to...
2025-03-2020 minAccounting in the WildMental Health During Tax SeasonLife coach Andrea Millar joins us to talk about how accountants and tax pros can maintain their mental health during tax season.
2025-03-1842 min
Whistle the FeastIsak Dinesen - Babette's FeastExcerpt from the film Babette's Feast read by Jason Jaspersen.All rights reserved to Gabriel Axel and Josi Konski.What is Babette's Feast?Babette's Feast Critic's Picks Videohttps://www.goodreads.com/book/show/10104532-babette-s-feast Host - Jason Jaspersen Co-hosts - Norah Kratz, Claire Marcus, Silas Gawrisch Producer - Jaksyn Graham Music Provided By: Renee Geving If you have any feedback for the show, or have any questions you can reach the podcast at feastreaders@gmail.com Whistle the F...
2025-03-0401 minAccounting in the WildWhat Exactly is "Offshoring"?In this episode, we talk to Chris Rivera from myCPE One about offshoring. What is it? Is it something to be scared of? How can it create growth onshore and lead to more jobs being created here?
2025-02-1821 min
The IOFM PodcastSetting Yourself Up for Success: 1099 Compliance and E-Filing Tips for 2025 As we kick off 2025, we're diving into one of the most crucial topics for financial professionals: setting yourself up for success this tax season. This episode features our compliance expert, Jason Dinesen, who shares actionable strategies to simplify your 1099 reporting and e-filing processes. Whether you're navigating the latest IRS requirements or looking to avoid costly penalties, Jason's insights will help you streamline operations and ensure compliance. Discover practical advice to start early, stay organized, and make 2025 your smoothest tax season yet.
2025-02-0516 minAccounting in the WildEpisode 2: 4 Things You Can Do Now to Make 1099 Season Better Next YearNow that most businesses have filed their 1099s for the year, what can you do now to make next 1099 season (January of 2026) better? Jason flies solo on this episode to give 4 tips.
2025-02-0413 minAccounting in the WildEpisode 1: The Research and Development CreditOur guest is Randy Eickhoff with Acena Consulting. Randy gives us a nice overview of the research and development credit: what it is, what's changing for 2025, and why a tax pro (or a business) wants to work with a specialist when making credit claims.
2025-01-2128 min
The Next Tour podcastEpisode 4 - Transition DecisionEpisode 4 – Transition Decision In this episode of The Next Tour, Ian and Andia meet with their friend of more than 20 years, Jason Medsger. Jason is an Air Force Colonel and is the Security Force Officer Career Field Manager. Although still active duty, he is getting ready to “push the button” for retirement and plans to retire effective August 2026. In this first installment of our time with Jason, we explore his questions leading up to his separation, including job prospecting, decision-making, and the impacts of transition on the family, both good and bad. Stay tuned for more installments of Jaso...
2025-01-1541 min
The Next Tour podcastEpisode 2 - Transition and a QuestEpisode 2 – Transition and a Quest In this episode of The Next Tour, Ian and Andia chat with Jason “Jay” France. Jay retired after more than 31 years in the Air Force finishing his career as the Command Senior Enlisted Leader at United States Transportation Command. At the culmination of his tremendous career, he took to the wilderness and hiked the Pacific Crest Trail (PCT), a childhood dream of his. Jay shares his transition story, his desire to have a quest on the PCT immediately following his transition out of uniform, the family dynamics impacting him during his journey, and the...
2025-01-1539 min
Accounting in the WildIntroduction -- Podcast Coming Soon!Jason Dinesen describes what this podcast is about, in this brief introduction.
2024-07-1800 min
The IOFM PodcastWhat to Know About the New IRS Form W-9In March 2024, the IRS quietly released a new version of its Form W-9, "Request for Taxpayer Identification Number and Certification." Although this revision had been pending for some time, the actual update was introduced with little fanfare. We spoke with tax expert Jason Dinesen to get a better understanding of how the form has changed and what it means for organizations that must collect this information. In this podcast, Dinesen answers these key questions — and more: How has the wording on the form changed and what's the impact? Do I need to collect a new form fr...
2024-07-0223 min
As the Dinesens TurnSeason 2, Episode 7: Tax Season RecapWe talk about how tax season went -- it went pretty well. We also talk about how there are clearly things that need to change in the future.
2024-04-1622 minAs the Dinesens TurnSeason 2, Episode 6: One Year in PortugalHard to believe for us, but we've been here for 1 year now.
2024-03-2223 minAs the Dinesens TurnSeason 2, Episode 5: Burnout RecoveryWe were both horribly burned out before we moved to Portugal. Burnout, in fact, is really our "why" as to why we moved. We've talked about it before, and we talk about it again here.
2024-03-1522 min
The IOFM PodcastCorrecting 1099s — What You Need to Know IOFM receives a lot of questions about the process for correcting 1099 filings, and even whether a correction is necessary in the first place. In this podcast, we speak to Jason Dinesen about the circumstances under which it might be necessary to issue one. What if the recipient's name was spelled wrong? What if the dollar amount or a TIN number was incorrect? What if a check was never cashed? And what should your approach be for correcting a 1099 if the recipient simply requests it? Jason also explains the importance of filing a correction by the deadline, and...
2024-02-2920 minAs the Dinesens TurnSeason 2, Episode 4: Super Bowl Watch PartyYes, we stayed up to watch the Super Bowl, til around 5 am our time.
2024-02-2817 minAs the Dinesens TurnSeason 2, Episode 3: Illness, Healthcare in PortugalWe had to take a few weeks off because we've all been battling colds and such. Tracy and Jason talk about having a cold in Portugal, going to the doctor, the costs (or lack thereof compared to America) of everything, etc.
2024-02-2322 minAs the Dinesens TurnSeason 2, Episode 2: How Tax Season Will WorkJason is still in business as an accountant. We talk about how that will work.
2024-01-2419 minAs the Dinesens TurnSeason 2, Episode 1: What the New Year Holds in StoreBack in the swing of episodes for season 2. We talk about the holidays, moving around Christmastime, and what 2024 holds in store.
2024-01-1714 minAs the Dinesens TurnEpisode 22: December AlreadyWe've been off for a few weeks in large part due to technical difficulties (we had 2 episodes recorded that got lost in a computer crash). Anyway, we are back with an episode about December in Portugal, what the holidays here look like, and what holiday plans are.
2023-12-0613 minAs the Dinesens TurnEpisode 21: All About Fall in PortugalThis episode is about fall, Halloween, and what life in general is like when the days get darker -- and very, very, very rainy!
2023-11-0111 minAs the Dinesens TurnEpisode 20: Goodbye Honeymoon, Hello RealityWhen one moves overseas, whether it's moving your home like us, or it's a semester-long study abroad or such, there's a honeymoon period. For us, this period lasted about 6 months. Now, the honeymoon is over and we're in the "this is the real world" phase of living here. Not necessarily bad, but a definite shift in the vibe.
2023-10-1329 minAs the Dinesens TurnEpisode 19: 5 Things, Part 2Jason and Tracy continue their discussion of 5 things they wish they knew before they moved to Portugal, and 5 things they have discovered they are glad for. In this episode:
Things they wish they knew:
--Don't be naive about language
--It can be oddly hard to find certain things such as green onions and jalepenos, and delivery drivers have a bizarrely hard time finding you
Things we are glad for:
--Services available
--Time, people's relationship to time and working to live
2023-10-0415 minAs the Dinesens TurnEpisode 18: Things We Wish We Knew, Things We Love, Part 1In this podcast, we start talking about the 5 things we wish we knew about Portugal before moving, and 5 things we have discovered we love. In this episode, we cover the first 3 things, and next week we will cover the final 2 items.
3 Things We Wish We Knew:
--Driving in Portugal is utter and complete chaos
--Red tape, bureaucracy
--The cost of day-to-day living is not necessarily lower than in the U.S. -- do not move to "save money" because it might not work out that way
3 Things We Have Discovered We love
--Work-life balance and people's attitudes toward life
...
2023-09-2920 minAs the Dinesens TurnEpisode 17: CareersJason and Tracy discuss having U.S. jobs in Portugal, and how Tracy is joining Jason on the dark side and becoming a tax preparer.
2023-09-2023 min
The IOFM PodcastCompliance Alert: What to Know About Major IRS E-Filing ChangesThe IRS is making some significant changes to e-filing requirements. While it used to be that you could choose to file 1099s in paper form as long as you didn't have more than 250 of any one type, that is no longer the case. In fact, the threshold for 2024 reporting of 2023 amounts has been reduced to an aggregated total of 10 forms of all types, and that includes more than just 1099s — it applies to W-2s and certain other forms as well. In this podcast, IOFM Managing Editor Royce Grayson Morse talks with Jason Dinesen of Dinesen Tax about...
2023-09-2028 minAs the Dinesens TurnEpisode 16: Jason and Tracy on School StartingSchool starts soon (September 15th). Last week the boys talked briefly about their thoughts on school starting, and how the summer went. This week, Jason and Tracy talk more about school starting.
2023-09-1316 minAs the Dinesens TurnEpisode 15: Boys Get Ready for SchoolIn this short podcast, we talk to the kids for as long as we could (**8 minutes!) about getting ready to start school next week.
2023-09-0607 minAs the Dinesens TurnEpisode 14: Language Learning, Does Duolingo Help, Taking Portuguese ClassesJason and Tracy cover a lot of ground on language learning. Jason talks about his philosophy when he was in school -- get B's because people leave you alone, getting A's is a lot of work with no real tradeoff, but getting C's means people hassle you. Plus does Duolingo work? And Jason tells the story about the first time his dad "took them outside the U.S." on vacation.
DETAILS:
0:32-1:55 Jason on his philosophy towards school — get Bs; getting As is a lot of work without a lot of great payoff; getting Cs means people hassle you, so...
2023-08-3020 minAs the Dinesens TurnEpisode 13: Burnout RevisitedOur journey of recovering from severe professional (and personal) burnout continues. We talked about this subject a few episodes ago, but our views on burnout continue to evolve -- and we have a lot to say about this topic -- so here is another episode! Tracy also talks about pottery, and how working with clay has helped her mental state.
2023-08-2327 minAs the Dinesens TurnEpisode 12: Vacationers in Our Town, Driving in PortugalAugust is vacation month for a lot of folks in Portugal, and our little town has lots of visitors. We also talk about driving and how it is (to an American) absolute chaos on the roads (always, even when vacationers aren't around).
2023-08-1728 minAs the Dinesens TurnEpisode 11: All the People in Portugal Who Have Helped UsWe've had a lot of help from people here in Portugal, and we seem to get what we need, when we need it.
2023-08-1113 minAs the Dinesens TurnEpisode 10: BurnoutTracy and Jason try to put burnout into words. They will be talking about burnout periodically, because their relationship with burnout, and ability to put it into words, changes daily.
2023-08-0121 minAs the Dinesens TurnEpisode 9: Residency Cards!Tracy and Jason received their residency cards last week. This podcast discusses what that means, and what the process was.
2023-07-2513 minAs the Dinesens TurnEpisode 8: Jack's Big School Trip, Plus Learning PortugueseJack recently got back from an overnight field trip. He didn't want to talk on the podcast, so Jason and Tracy talk about his trip. Plus we talk about taking Portuguese classes, and whether Duolingo is helpful or not in learning a language.
2023-07-2028 minAs the Dinesens TurnEpisode 7: Work SchedulesHow does it work, working for U.S. clients while living in Portugal? How on earth did a move during tax season actually work? We discuss in this podcast.
2023-07-1413 minAs the Dinesens TurnEpisode 6: Vacation, Weather and MoreWe took our first vacation in Portugal recently, and recap where we went. Plus, we talk about the weather, regional differences we have observed, and we talk about trying to break the consumer mentality of "let's go to the mall and buy stuff."
2023-07-0729 min
As the Dinesens TurnEpisode 5 -- Talking with TylerTyler (age 11) joins us to discuss his thoughts on Portugal as we are now past the 3-month mark living here.
2023-06-3011 minAs the Dinesens TurnPodcast, Episode 4: All About SchoolThis episode is all about school. Our kids attended public school the last 3 months of the school year, and we talk about how we got them enrolled and what their experiences were.
2023-06-2320 minAs the Dinesens TurnEpisode 3We are now official tax residents of Portugal! This podcast is all about the paperwork and the process.
2023-06-1624 minAs the Dinesens TurnAs the Dinesens Turn, Episode 2Living in 300 square feet in Portugal, versus living in 3,000 square feet in the U.S. That is the topic of Episode 2 of As the Dinesens Turn.
2023-06-0214 min
As the Dinesens TurnEpisode 1 -- IntroductionThis is our first episode, an introduction to who we are and what we're up to, and a preview of what future podcasts will be about.
2023-05-1922 min
Well-ReadWell-Read Episode #94 -Book PairingsThanks to a fabulous listener suggestion (hi Rikke!), we’re pairing books that inform each other or benefit from reading them back-to-back. What books would you pair up? As always, we’ll end with what we’re reading this week.
Books and other media mentioned in this episode:
Pride and Prejudice by Jane Austen (buy from Bookshop)
Bridget Jones’s Diary by Helen Fielding (buy from Bookshop)
My Dark Vanessa by Kate Elizabeth Russell (buy from Bookshop)
Lolita by Vladimir Nabokov (buy from Bookshop)
Ann’s picks:
The Seducer’s Diary...
2021-05-0852 min
Financial ReconHere Comes The Tax Man....Conversation with Jason Dinesen EA, LPA on tax law changes impacting you in 2020 & 2021, what to look out for, and how to stay on your tax preparers good side during tax season!Twitter: @dinesentaxWebsite: https://www.dinesentax.com/ Hosted on Acast. See acast.com/privacy for more information.
2021-01-2633 min