Tax Smart Real Estate Investors Podcast
Hall CPA
The Tax Smart Real Estate Investors Podcast is a show that focuses on tax, accounting, and finance tips for real estate investors and business owners. We bring on guests to talk through complex topics and we break it down into bite-sized chunks of knowledge for our listeners.
Our episodes generally run 30-60 minutes of no-nonsense, hard-hitting information. We know your time is valuable so our goal is to save you thousands of dollars per episode.
Hall CPA, PLLC is a CPA firm that exclusively serves real estate investors and real estate business owners. We work with syndicators and developers closing multi-million dollar deals, as well as small investors building a portfolio from scratch.
Check us out at www.TheRealEstateCPA.com/Podcast for more free content and information.
Enjoy!
The Tax Smart Real Estate Investors podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests. Any mention of third-party vendors, products, or services does not constitute an endorsement or recommendation. You should conduct your own due diligence before engaging with any vendor
Our episodes generally run 30-60 minutes of no-nonsense, hard-hitting information. We know your time is valuable so our goal is to save you thousands of dollars per episode.
Hall CPA, PLLC is a CPA firm that exclusively serves real estate investors and real estate business owners. We work with syndicators and developers closing multi-million dollar deals, as well as small investors building a portfolio from scratch.
Check us out at www.TheRealEstateCPA.com/Podcast for more free content and information.
Enjoy!
The Tax Smart Real Estate Investors podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests. Any mention of third-party vendors, products, or services does not constitute an endorsement or recommendation. You should conduct your own due diligence before engaging with any vendor
Episodes
Mentioned books
Nov 5, 2026 • 33min
From Losing Everything as an LP to Owning 1,500+ Apartment Units with Gary Lipsky
Gary Lipsky, founder of Break of Day Capital and a former education-company entrepreneur, shares his journey from losing everything as a passive investor to owning 1,500+ apartment units. They explore multifamily strategy, specializing in Tucson, operating through staff turnover and flat NOI, AI in property management, the dangers of short-term debt, 1031 exchanges, retirement accounts, and evaluating investment sponsors.
15 snips
Nov 3, 2026 • 25min
402. The $512K Tax Cap Most High-Income W-2 Earners Don’t Know About
High-income W-2 earners using real estate professional status or short-term rentals may encounter a surprising $512,000 excess business loss limit. The discussion covers how excess losses become NOL carryforwards, how bonuses and stock compensation affect timing, and why multi-year modeling matters. Real estate, passive activity, basis, participation, and AI-related pitfalls all get a closer look.
16 snips
Oct 29, 2026 • 36min
From $70M in Personal Guarantees to Debt-Free Investing with Joel Friedland
Joel Friedland, founder of Brit Properties, has spent decades investing in Chicago-area industrial real estate. He shares his journey from lawn sales to syndications, why $70 million in personal guarantees changed his view of debt, and how debt-free properties can deliver strong returns. They also explore cost segregation, sticky tenants, investor liquidity, deal-by-deal ownership, and the risks of inexperienced syndicators.
12 snips
Oct 27, 2026 • 36min
401. Dave Meyer Returns to Score His 2024 Real Estate Predictions (and Makes New Ones)
Dave Meyer, BiggerPockets’ chief investment officer and a leading housing-market analyst, returns to revisit his 2024 forecasts. He explores the housing market’s “great stall,” the lock-in effect, and where investors can still uncover value. The conversation also covers AI infrastructure, bond yields, commercial real estate distress, short-term rentals, and building a portfolio designed around patience and freedom.
10 snips
Oct 22, 2026 • 41min
$100B+ in Deals After Thinking She’d Get Fired at Morgan Stanley: Deb Smith
Deb Smith, co-founder and CEO of CenterCap Group, has advised on more than $100 billion in real estate deals. She traces her journey from an Australian dairy farm to Morgan Stanley and launching a firm during the financial crisis. Topics include AI’s impact on real estate, the splintering of traditional property categories, emerging niches such as wellness and senior housing, and how sponsors can attract institutional capital.
17 snips
Oct 20, 2026 • 41min
400. The Core Tax Strategy Blueprint: The Plan We Give Our Top Clients
A practical year-end tax strategy blueprint for real estate investors and high-income earners. Topics include real estate professional status, short-term rentals, grouping elections, cost segregation, bonus depreciation, 1031 and 721 exchanges, Buy-Borrow-Die planning, S corporations, the Augusta Rule, hiring children, home offices, and oil and gas investments.
26 snips
Oct 15, 2026 • 50min
Investing by Gut Feeling? Why Data Beats It “by a Million Miles” with Neal Bawa
Neal Bawa, a technology entrepreneur, real estate investor, and multifamily data expert, explores why supply data can overturn market hype, including his decision to pass on Huntsville. He discusses multifamily rent and value trends, Claude-powered underwriting, emerging markets like Boise, and his strategy of acquiring retiring CPA firms. The conversation also examines agentic AI’s impact on accounting and white-collar work.
38 snips
Oct 13, 2026 • 36min
399. Thinking About a 1031 Exchange? 5 Key Questions to Consider with Julia Fritzlen
Julia Fritzlin, an investment advisor specializing in 1031 exchanges and passive real estate, joins the conversation on planning life after selling property. They explore exchange deadlines, debt boot, Delaware Statutory Trusts, investment risks, illiquidity, and alternatives such as syndications, funds, and oil and gas. A practical look at preparing for a tax-conscious real estate exit.
18 snips
Oct 8, 2026 • 28min
Claim Denied: The Insurance Mistakes That Could Cost You
Real court cases reveal how undisclosed short-term rentals, LLC or trust transfers, and outdated replacement estimates can derail insurance claims. The discussion explores flood coverage gaps, lender-placed policies, soaring premiums that kill deals, insurer withdrawals from risky markets, and the importance of umbrella protection when liability lawsuits exceed property limits.
18 snips
Oct 6, 2026 • 31min
398. 4 Ways Your Short-Term Rental Occupancy Tax Can Go Wrong with Serena Verma
Serena Verma, a real estate investor, private lender, and founder of HostVisors and Monterra Tax, reveals how an audit uncovered $250,000 in short-term rental tax exposure. She explores four costly failure points: over-collection, under-collection, over-remittance, and under-remittance. The discussion covers Airbnb and OTA errors, zero-dollar returns, PMS setup problems, years of booking reviews, and tax due diligence before portfolio sales.
