What if a third of everything you built disappeared on the way out the door?

Ashley Romiti underwrote more than $500 million in real estate as an investment property agent in Orange County. After nearly 15 years in commercial real estate she kept seeing the same story: longtime owners on appreciated property, worn down by management, with no idea what their exit options were. So she founded GCA 1031, where she helps retiring landlords move into passive, tax-deferred income.

In this episode, Ashley explains why a sale can hand 30% to 40% of the gain to capital gains, depreciation recapture, net investment income tax and state taxes, how a 1031 exchange defers the entire bill, why the 45-day and 180-day deadlines carry no extensions, how Delaware Statutory Trusts trade the keys for shares of institutional real estate, and the fee loads and sponsor red flags to watch for.

Chapters:

• 00:00 - A Third of Your Gains Can Vanish
• 01:44 - Millions Own Rentals and Cannot Exit
• 05:20 - What Selling Really Costs an Owner
• 07:55 - Tax Planning Before the Sale Not After
• 09:34 - How a 1031 Exchange Actually Works
• 11:18 - 45 Days and 180 Days No Extensions
• 12:53 - Delaware Statutory Trusts Explained
• 15:47 - Trading Control for Passive Income
• 17:49 - Why DST Fees Run 8 to 12 Percent
• 21:41 - Step Up in Basis and Estate Planning
• 25:45 - Value the Property and Pull the Return
• 27:36 - The Roth Mistake That Cost Me Years
• 30:44 - Layered Taxes Hit Real Estate Hardest
• 33:13 - The Third Door in the Tax Code
• 35:29 - Four Steps to Price Your Exit
• 37:41 - You Spend What Is Left Not Net Worth

Escape The Clock Resources:

📖 The Book — https://escapetheclock.com/book

⬇️ The Planner — https://escapetheclock.com/toolkit

🎙️ The Podcast — https://escapetheclock.com/podcast

🤝 1:1 Help — https://escapetheclock.com/schedule

✉️ Free Monthly Insights — https://escapetheclock.com/subscribe

Episode References & Resources:

ℹ️ Who owns America's rentals - HUD / Census (2022) https://archives.hud.gov/news/2022/pr22-242.cfm

ℹ️ Housing wealth held by age 60+ - Realtor.com and Redfin (2025) https://www.realestatenews.com/2025/07/22/boomers-now-hold-nearly-40-of-us-housing-wealth

ℹ️ Capital gains and the 25% recapture ceiling - IRS Topic 409 (2025) https://www.irs.gov/taxtopics/tc409

ℹ️ Depreciation allowed or allowable - IRS FAQ (2025) https://www.irs.gov/faqs/sale-or-trade-of-business-depreciation-rentals

ℹ️ Net investment income tax - IRS Topic 559 (2025) https://www.irs.gov/taxtopics/tc559

ℹ️ Like-kind rules and the 45 and 180 day deadlines - IRS FS-2008-18 https://www.irs.gov/pub/irs-news/fs-08-18.pdf

ℹ️ DST equity raised in 2025 and sponsor count - Mountain Dell (2026) https://altswire.com/dst-sales-surpass-8-4-billion-in-2025-according-to-mountain-dell/

ℹ️ Investors who exchange only once - Ling and Petrova (2020) https://1031buildsamerica.org/study-ling-petrova-2020/

Connect with Ashley:

🌐 Website — https://www.gca1031.com

💼 LinkedIn — https://www.linkedin.com/in/ashley-romiti-dst

📊 Free DST Guide — https://www.gca1031.com/access-the-dst-investor-guide/

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This information is for educational purposes only and not financial advice. Consult a qualified professional for personalized guidance.

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