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I Made Millions In Real Estate…It Wasn’t Worth It. — Key Takeaways

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I Made Millions In Real Estate…It Wasn’t Worth It.

Graham Stephan19mJul 8, 2026

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Raise rent to the maximum allowable every year on rent-controlled properties — Graham's failure to do so cost him $100,000 in lost sale price on a single property.

Key takeaways

Skipping annual rent increases under rent control destroys sale price

Skipping annual rent increases under rent control destroys sale price

  • LA rent control caps future increases on the lower base — one missed year compounds into permanent shortfall; 6 years of skipped 3% raises cost ~$100K on sale price.
  • Below-market rents directly suppress investor valuations since income-based pricing penalizes any landlord who 'plays nice.'

Real estate returned only 4-5%/yr after true expenses — matching T-bills

Real estate returned only 4-5%/yr after true expenses — matching T-bills

  • After backing out repairs, vacancy, insurance, utilities, and maintenance, actual annual return was 4-5% — same as risk-free Treasuries.
  • Appreciation was the headline number, but illiquid equity is worthless until sold; index funds matched returns with zero hassle or liability.

Depreciation recapture taxed at 25% federal + 10% CA state on exit

Depreciation recapture taxed at 25% federal + 10% CA state on exit

  • IRS claws back all depreciation deductions at 25% upon sale — early tax savings are a deferral, not a benefit, for anyone fully exiting real estate.
  • California adds 10%+ state tax on top, making total exit tax burden potentially 35%+ for CA landlords who don't 1031 exchange.

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In this video

  1. 1mReal Estate Investing Wasn’t Worth It
  2. 1mHow I Purchased Properties
  3. 3mNot Raising The Rent
  4. 6mImportance Of Good Credit
  5. 8mIncreased Repairs
  6. 10mAnnualized Returns
  7. 12mSelling Everything
  8. 13mPaying Taxes
  9. 14mThe Hassle Factor
  10. 16mBuying Real Estate In 2026

“what you're really buying is customer service with property taxes”

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