🎙️ Introduction
On this episode of The Best Ever Show, host Joe Fairless sits down with Anna Myers, Vice President at Grocapitus Investments and a master underwriter who brings 20+ years of tech and business experience into multifamily investing. Anna shares her real estate journey—from early mistakes in remote single-family investing to scaling up into multifamily, where she now helps acquire and analyze properties nationwide. With her data-driven approach and underwriting superpowers, Anna delivers invaluable insights on evaluating markets, avoiding pitfalls, and building strong partnerships.
📌 Key Takeaways
✅ Lessons from Early Mistakes – Anna’s short sale taught her the importance of strong job markets, multiple data points, and not investing in isolation.
✅ Teamwork Matters – Real estate is a team sport; partnering with others balances skillsets and reduces risk.
✅ Underwriting Superpowers – Anna excels at spotting formula errors, analyzing deal structures, and evaluating partnership terms like catch-ups in pref structures.
✅ Rent Comps Are Critical – Incorrect comps can sink a deal; always verify with multiple sources and walk the competition.
✅ Market Fundamentals Trump Cashflow – Jobs, income, and demographics (“the emperor”) matter more than short-term cashflow (“the king”).
✅ Creative 1031/121 Exclusion Strategy – Anna converted a Bay Area primary home into $500K tax-free plus a high-cashflow Airbnb through smart tax structuring.
⏱️ Chapters
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01:45 – Anna’s Background – From tech career to multifamily investing.
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06:30 – Early Mistakes – Short sale lessons from Mississippi.
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12:50 – Power of Partnerships – Why teaming up changed her trajectory.
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18:40 – Underwriting Superpowers – Spotting errors, analyzing structures, and asking the right questions.
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28:00 – The Importance of Rent Comps – How to verify and avoid faulty assumptions.
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34:25 – Market Fundamentals – Key criteria Anna looks for in cities and neighborhoods.
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44:15 – Best Deal – Turning $620/month cashflow into $500K tax-free + $6K/month Airbnb.
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52:40 – Lightning Round – Books, mistakes, and giving back through teaching.
