Overview:

In this episode, Derek brings in Tracy Dombeck—his wife and longtime bookkeeper—to shine a light on a topic often overlooked by entrepreneurs: bookkeeping. They cover everything from basic financial hygiene to handling complex real estate deal structures like flips, rentals, subject-to transactions, and lease options. Packed with practical advice, this is a must-listen for real estate investors who want to protect their profits, avoid audits, and keep the IRS off their back.

📌 Why Should You Listen?

• You're a real estate investor (or planning to be one).

• You’ve been “winging it” with your books or relying on QuickBooks guesses.

• You want to avoid common tax-time disasters.

• You’re doing creative deals and don’t know how to track them.

• You’re unsure whether to hire a VA, bookkeeper, or CPA—and when.

✅ Key Takeaways

1. Bookkeeping isn’t optional. Bad habits now lead to huge penalties later.

2. Separate your business and personal finances. No co-mingling!

3. Track EVERYTHING. Small receipts matter and can reduce your tax burden.

4. Know when a 1099 worker is really an employee. Get this wrong = audit & penalties.

5. Rental vs. flip properties must be categorized differently.

6. Subject-to deals & lease options need special bookkeeping treatment.

7. Hiring cheap bookkeepers can cost you more in cleanups later.

8. Review your Profit & Loss and Balance Sheet monthly.

9. W-9s, 1099s, and correct classifications are critical.

10. TrustPoint Bookkeeping offers flexible, experienced help nationwide.

🧠 Relevant Topics Discussed

• Bookkeeping for real estate investors

• Flip vs. rental property accounting

• Subject-to financing & lease option tracking

• Payroll, W-9s, and contractor vs. employee

• Sales tax, use tax, and IRS compliance

• Hiring bookkeepers vs. VAs

• Setting up separate business accounts

• Cost expectations for professional bookkeeping

⏱️ Timestamps (approximate) Time Topic 00:00–02:00 Introduction & why bookkeeping matters 02:00–06:00 Common mistakes investors make with receipts and records 06:00–09:00 Business vs. personal finances—separate everything! 09:00–13:00 Employees vs. 1099 contractors—don’t get caught 13:00–15:00 Sales tax misconceptions and receipt management 15:00–18:00 Payroll basics and why it’s not as scary as it sounds 18:00–20:30 Interest reporting and W-9/1099 rules 20:30–23:00 Categorizing rentals vs. flips—common investor errors 23:00–25:00 Handling subject-to deals and closing statements 25:00–27:30 Lease options and how to track option fees correctly 27:30–29:30 Dangers of hiring untrained VAs for bookkeeping 29:30–31:00 What bookkeeping services cost and what to expect 31:00–32:00 Final advice and how to contact TrustPoint Bookkeeping

 

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