The Mr. R Show Chris Picciurro and John Tripolsky

About the Guest:
Natalie Kolodij is a seasoned Enrolled Agent (EA) specializing in real estate taxation. She is the founder of Kolodij Tax and Consulting and serves as an educator and consultant for tax professionals. She offers an in-depth understanding of short-term rentals (STR) and the intricacies of real estate tax strategies. Natalie is also the creator of the Certified Real Estate Tax Strategist (CRETS) program, which provides comprehensive education and continuing professional education (CPE) for tax professionals.
Episode Summary:
Welcome back to the Mr. R Show, where we dive deep into the world of real estate taxation with premier tax strategist Natalie Kolodij. Chris and John engage Natalie in a riveting discussion that explores the critical aspects of short-term rentals (STRs) and their tax implications. As STRs have surged in popularity, they bring unique tax complexities that can be strategically leveraged for significant benefits.
In this episode, Natalie breaks down fundamental concepts such as the 7-day and 30-day rules, material participation, cost segregation studies, and the nuances of Schedule C versus Schedule E. The dialogue also ventures into substantial services, real estate professional status, and vital planning opportunities, providing tax professionals with actionable insights to optimize their clients’ tax scenarios. Whether you are veteran or newcomer to the tax profession, this episode is a comprehensive guide to mastering the short-term rental loophole.
Key Takeaways:
Understanding STR Definitions: Clear distinctions between average stays of seven days or less and 30 days or less with substantial services are essential for correct tax treatment.Material Participation: Key to unlocking non-passive loss treatment; typically achieved through the 100-hour rule where the taxpayer's involvement exceeds others.Cost Segregation Studies: Crucial for accelerating depreciation and maximizing tax benefits. Can apply retroactively to properties placed in service in prior years.Compliance with IRS Guidelines: Taxpayers must distinguish between operational and investor hours, ensuring appropriate logs and substantiation.Real Estate Makes for Strategic Tax Planning: Real estate investors can significantly benefit from strategic annual testing, cost segregation studies, and proper entity structuring.Notable Quotes:
"There has to be a verb. If the verb didn't happen while the guest was renting the property, we don't have a substantial service." - Natalie Kolodij"If you have a short-term rental and meet this loophole, they can offset other types of income, most likely high w-2 wages." - Chris"Anyone listening, if you have clients who have short-term rentals, or where they might need rental losses for any reason, if it's been five years or less, I would look at it [cost seg study] with consideration." - Natalie Kolodij"For material participation, it's typically going to be any of the hours required for the day-to-day operations." - Natalie Kolodij"Understanding the common expenses and what is a capitalized renovation versus an expense, those are where I see the most errors related to rentals." - Natalie Kolodij
Resources (Explore):
Kolodij Tax and ConsultingREPStracker (DISCOUNT CODE: IFG)Resources (Listen):
Natalie Kolodij’s PodcastTeaching Tax Flow PodcastResources (Learn):
Certified Real Estate Tax Strategist (CRETS) ProgramTax Pro 2.0 Mastermind (Now Open)Engage deeply with this episode to enrich your understanding of short-term rental taxation and expand your tax planning arsenal. Tune in for more expert insights that can revolutionize your practice on the Mr. R Show.

FREE CPE (1 credit) via EarMark: https://bit.ly/4baSg5P
Episode Summary:
In this enlightening episode of the Mr. R Show, hosts John and Chris dive deep into the transformative power of AI in the tax and accounting industry, featuring industry thought leader John Higgins. Against the backdrop of returning from a brief hiatus, they explore the future of tax practices and the significant role of artificial intelligence. John kicks off the conversation emphasizing the necessity for harmony between work and life while achieving profitability, a central theme of the show.
John Higgins sheds light on his journey from traditional CPA roles to becoming a tech and AI strategist. With the rise of AI, particularly generative AI like chat GPT and Microsoft Copilot, John discusses how tax professionals can leverage these tools to improve efficiency and client advisory services. The conversation touches on concerns about AI causing intellectual laziness but overwhelmingly favors the positive impacts on the industry. They share practical insights on using AI to automate Excel tasks, enhance tax planning, and even streamline PowerPoint presentations, emphasizing the substantial time savings and improved quality of work.
About the Guest (John Higgins): John Higgins is a well-regarded figure in the accounting and CPA profession, with a career spanning several decades in technology and professional education. He began his career at a local CPA firm in Michigan before founding Computools, focusing on accounting systems and local area networks. John later worked with BDO as a national partner and co-founded CPA Crossings, providing CPE programs on technology. In 2020, he sold CPA Crossings and started Higgins Advisory, where he continues to educate and consult on emerging technologies like AI. He's an ice hockey enthusiast and engages actively in sports like golf and pickleball.
Key Takeaways:
Leveraging AI in Tax Practices: Tax professionals can use AI tools like chat GPT and Microsoft Copilot to automate routine tasks, enhance advisory services, and improve client interactions.Generative AI Explained: Generative AI analyzes massive datasets to predict and generate content, facilitating tasks from creating tax planning recommendations to automating Excel macros.Evolving Technology Landscape: The shift from traditional on-premise software to cloud-based solutions is accelerating, with newer tech firms innovating and incorporating advanced AI functionalities.Embracing Technology and Overcoming Resistance: Older and more traditional firms need to overcome resistance to change, understanding the ROI and productivity gains from incorporating advanced technologies.Opportunities for Young Practitioners: Emerging tax professionals starting fresh have the advantage of building a tech-forward practice, leveraging cloud-based and AI-driven tools right from the start.Notable Quotes:
"Is AI going to replace tax practitioners? No, but tax practitioners who use AI will replace tax practitioners who don't." - John Higgins"Chat GPT can be a great tool for automating your Excel spreadsheets." - John Higgins"Your practice is going to run exactly how you've engineered it to run. If you don't like something, you're in control of how it occurs." - Chris"The quality of my presentations has gotten better by using AI. It's not about replacing expertise but augmenting it." - John Higgins"For many firms, the value proposition for cloud technology is strong. It's mainly an education issue when there’s reluctance to adopt it." - John HigginsResources:
Higgins AdvisoryStandford Tax: An emerging tool for document organization in tax practices.Microsoft Copilot: AI tool for enhancing productivity within Microsoft 365.Chat GPT: OpenAI's generative AI tool used widely for content automation and productivity. Dive into the full episode to gain deeper insights into how AI is revolutionizing the tax and accounting landscape, and stay tuned for more enlightening content from the

In this episode, we are joined by Chase Birky, founder of Dark Horse CPA, who shares his journey from accidentally starting his own firm to creating a platform CPA firm that supports and empowers other tax professionals. He discusses the difference between growing and scaling a practice and the importance of client selection, pricing, and setting expectations. Chase also highlights the value of collaboration and the need for tax professionals to focus on their core strengths while leveraging technology and strategic partnerships to enhance their services.
Key Takeaways:
Scaling a tax practice requires setting clear expectations with clients, getting pricing and scoping right, and focusing on providing value.Client selection is crucial for building a successful practice, and it's important to say no to clients who are not a good fit.Collaboration and leveraging technology can help tax professionals streamline their processes and provide better service to clients.Private wealth management and specialty tax services can be valuable additions to a tax practice, but strategic partnerships may be necessary to provide these services effectively.Niche specialization can be a powerful way to differentiate and grow a tax practice, but it's important to consider market size, vulnerability to regulation changes, and potential risks.
Quotes:
"If you don't set expectations with clients, they're going to run your practice for you.""Everything bad in a practice stems from getting the pricing wrong, getting the scoping wrong, or not setting appropriate expectations with clients.""Being a generalist is harder to provide value to an individual client than if you know that client's needs inside and out.""Collaboration over competition is essential in the tax and CPA world.""The tax pro-CPA financial advisor relationship is crucial for providing comprehensive financial services to clients."- - -
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In this jam-packed episode of the Mr. R Show, we venture into the realm where the worlds of cybersecurity and successful tax practices intersect. As technology continues to advance at an unprecedented pace, the challenges of safeguarding client data and records in the tax industry have become more pronounced than ever. Join us as we unravel the complexities of this crucial topic and shed light on the latest developments.
Our special guest, Brand Messner, a seasoned expert an leader in the field, guides us through the nuances of cybersecurity and its direct implications for tax professionals. The Internal Revenue Service (IRS) is now placing stringent requirements on firms, compelling them to prioritize the security of sensitive information. We delve into the details of what these requirements entail and how tax practitioners can navigate this evolving landscape.
One key aspect we explore in depth is the Written Information Security Program (WISP). What is a WISP, and why is it of paramount importance in the current digital age? Brand shares valuable insights into the significance of implementing a robust WISP, offering practical advice on how tax practices can enhance their security measures.
Whether you're a seasoned tax professional or just starting in the industry, this episode provides essential information on safeguarding client data and staying compliant with the latest IRS mandates. Join us for a compelling conversation that will empower you to secure success in your tax practice.
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FREE CPE (1 credit) via EarMark: https://www.earmark.app/course/521c210f-81d8-44be-89e7-b16168bd1c3e
In this jam-packed episode, we sit down with Chris Picciurro, CPA, MBA, PFS, ARA, a seasoned tax professional and founder of the Monthly Recurring Revenue Institute, who has transformed his private practice by embracing a revolutionary concept - "Subscribing to A Better Firm." Join us as Chris shares his inspiring journey of modernizing his operations, regaining control of his life, and enhancing client relationships in the process.
Many tax professionals grapple with the constant challenges of staying current in a rapidly evolving industry while managing their practice efficiently. Chris’ story is a testament to what can be achieved when one dares to break free from the conventional and embrace innovative ideas.
In this episode, Chris walks us through the transformative idea of "Subscribing to A Better Firm" and explains what it means for tax professionals like himself. He details the trials and tribulations his team faced while implementing this concept and how the benefits far exceeded any worries that may have initially held them back.
Discover how Chris overcame the hurdles of change and adopted modern strategies that not only improved his practice's efficiency but also allowed him to reclaim control over his own life. By embracing new technology, streamlined processes, and a client-centric approach, he was able to redefine his firm's trajectory.
Chris’ journey is a compelling reminder that innovation and adaptability are essential for the continued success of any business. Tune in to this episode to gain insights into how modernization can positively impact your practice, rekindle your passion for tax work, and, most importantly, deepen your client relationships.
Whether you're a seasoned professional or just starting out, this episode is sure to provide invaluable guidance for navigating the ever-changing landscape of the tax industry.

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Welcome back for another episode! Today we jump into the world of tax planning for foreign investors, featuring Angie Ortega, the founder of CEO Accountant. In this discussion, we'll explore a range of real-world client examples that shed light on effective tax strategies for international investors.
What does tax planning for foreign investors entail, you might wonder? It's a crucial aspect of financial management for individuals and businesses with cross-border interests. With Angie's wealth of expertise, we'll demystify the complexities of this field and show you how to optimize your tax situation as a foreign investor.
Throughout our conversation, we'll explore common misconceptions and pitfalls that foreign investors often encounter. Discover the truth about tax planning for international investments and how it can help you maximize your financial returns, regardless of the scale or nature of your investments abroad.
Don't miss out on this opportunity to gain invaluable insights from Angie Ortega, a seasoned professional who has assisted countless investors in navigating the intricacies of tax planning for foreign investments. This episode is sure to offer valuable information for future growth in your practice or help identify the best strategic partners to whom you might be looking to refer clients to.
Tune in and get ready to kick into high gear, your knowledge of tax planning for foreign investors!