George Dimov, CPA, shares the biggest tax mistakes real estate investors make, why proactive planning matters, and how to build smarter portfolios.

In this episode of RealDealChat, Jack sits down with George Dimov, CPA and founder of DimovTax.com, to discuss proactive tax planning, common mistakes investors make, and why accounting + real estate go hand in hand.

George shares his journey from immigrant beginnings to building a tax practice that serves thousands of clients nationwide. He explains why he invests heavily in real estate himself, how tax strategies like cost segregation and 1031 exchanges really work, and why many accountants fail to guide clients beyond tax season.

Here’s what you’ll learn in this conversation:

• The biggest lie real estate investors tell themselves about appreciation
• Why many accountants don’t help with tax planning year-round
• Common investor mistakes: emotional purchases & ignoring due diligence
• How CPAs view real estate vs other asset classes
• The hidden risks of ignoring property management in rentals
• Why proactive planning in July beats rushing in April
• Three underutilized tax strategies for small business owners & investors
• The truth about short-term rentals, real estate professional status & audits
• How to pick the right business structure (LLC, S-Corp, C-Corp)
• Why AI won’t replace accountants but will make relationships more important

📌 Learn more at DimovTax.com

💡 Want help scaling your real estate business with AI and automation?

Schedule your free strategy session today: https://realdealcrew.com

Call to Action:

Learn more at https://realdealcrew.com

00:00 – Why accountants love real estate as an asset class

01:00 – George’s background & immigrant story

03:00 – From back-office accounting to CPA entrepreneur

04:00 – Why real estate was his first personal investment

06:00 – The conservative nature of accountants & real estate investing

07:00 – Biggest challenges: property management & finding reliable help

08:00 – Common investor tax challenges explained

10:00 – Why most clients wait until tax season (and why that’s too late)

12:00 – Inside scoop: why many accountants don’t do planning

14:00 – The Go-Giver mindset & educating clients proactively

16:00 – Three underutilized tax strategies for business owners

19:00 – Balancing tax savings vs audit risk

21:00 – Short-term rentals & real estate professional rules

23:00 – Why most tax tips on social media are dangerous

24:00 – The importance of licensed pros with real estate expertise

25:00 – George’s biggest business mistake & lessons learned

28:00 – AI vs accountants: why human touch matters more than ever

30:00 – Rapid fire: lies, advice, books & time-saving tools

#RealEstateInvesting #TaxStrategy #CPAAdvice #DimovTax #RealEstateTaxes #PassiveIncome #RealDealChat #CostSegregation #1031Exchange #ShortTermRentals #BusinessStructure #ProactiveTaxPlanning #RealEstateAccounting #GenerationalWealth #AIAndAccounting

RealDealCrew.com

We empower real estate investors by optimizing your business processes through customized automation and system integration. From lead management to deal closure, we help you build a scalable and efficient operation. Learn more at RealDealCrew.com

LIKE • SHARE • JOIN • REVIEW

• Website
• Apple Podcasts
• YouTube
• YouTube Music
• Spotify
• Amazon Music
• Facebook
• Twitter
• Instagram

SUPPORT THE SHOW!

• If you are new to Wealthfront, and open a Cash Account, you'll get a 0.50% APY boost for 3 months.
• Open an Automated Index Investing Account or Automated Bond Portfolio, you'll earn $5,000 managed for free.
• Get $10 and Reduce Your Business Costs by Shopping at AppSumo • https://bit.ly/reiappsumo
• Get $10 Towards Your First Purchase at Drop • https://drop.com/?referer=3DC729