In this episode of Properties to Profits, I sit down with Randy from OWIC CPA, a seasoned CPA and entrepreneur who’s reimagining how small businesses and real estate investors approach taxes. We unpack the growing CPA shortage, discuss how his firm is cultivating new talent and providing exit strategies for retiring professionals, and explore the sweeping impacts of the new tax bill signed in July.
We also dig into powerful tax-saving strategies that benefit everyone from tipped employees and overtime workers to high-income professionals and real estate investors. Whether you’re just getting started or scaling your portfolio, this conversation offers essential insights into how to keep more of what you earn, reduce tax liabilities, and build lasting wealth through community, strategy, and smart investing.
Episode Highlights
[0:00] - Introduction to Randy and his CPA firm’s mission to serve real estate investors and business owners
[3:47] - Why the CPA industry is facing a massive labor shortage and what Randy’s doing to solve it
[5:09] - Succession planning for small CPA firms and why most lack an exit strategy
[6:12] - Innovative talent development and acquisition strategy to support retiring CPAs
[7:33] - Importance of peer collaboration and building a support network in the tax space
[9:16] - Leveraging community to fund larger real estate deals and build long-term wealth
[12:22] - How real estate operators can capture value by holding, not wholesaling, deals
[13:06] - Where most business owners struggle—bookkeeping, taxes, and operations
[16:09] - Highlights from the new tax bill: tax breaks for tipped employees and overtime workers
[18:07] - How marginal tax rates make these tax breaks so valuable
[23:03] - New permanent tax benefits for business owners: bonus depreciation and QBI
[25:11] - What QBI means and how it saves business owners thousands
[27:16] - Why 100% bonus depreciation is a game-changer for equipment and real estate
[30:17] - Cost segregation studies: how they work and why they’re powerful
[32:09] - Alternative to 1031 exchanges using accelerated depreciation
[35:52] - Rising interest rates and their impact on multifamily and commercial real estate
[38:03] - How high-income individuals and married couples can still unlock major tax benefits
[40:00] - Active vs. passive losses and how to qualify for real estate professional status
[43:15] - Short-term rentals and other carve-outs that help high earners deduct losses
[47:12] - Real-life tax strategy for dual-income households with different income levels
[48:14] - Why it’s crucial to diversify between tax-deferred, tax-free, and personal assets
[49:46] - Who Randy works with—and how his firm helps eradicate entrepreneurial poverty
[54:13] - The complexity of real estate books and how Randy’s firm handles it for investors
5 Key Takeaways -
The CPA profession is facing a critical talent and succession crisis—Randy is working to bridge this gap by training new CPAs and acquiring firms lacking an exit plan.
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The new tax bill provides significant savings for tip earners and overtime workers, offering real opportunities for average Americans to boost their savings or invest.
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Real estate investors and business owners can now benefit from permanent bonus depreciation and expanded QBI deductions, creating massive tax reduction potential.
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Cost segregation and bonus depreciation can be more effective than 1031 exchanges, especially when timing or deal quality is an issue.
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Strategic entity structure and role designation (active vs. passive) are key for high earners to leverage losses and dramatically reduce their overall tax burden.
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