Trapped by the Win: How to Keep the Gains and Take the Exit with Ashley Romiti

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 Vanish01:44 - Millions Own Rentals and Cannot Exit05:20 - What Selling Really Costs an Owner07:55 - Tax Planning Before the Sale Not After09:34 - How a 1031 Exchange Actually Works11:18 - 45 Days and 180 Days No Extensions12:53 - Delaware Statutory Trusts Explained15:47 - Trading Control for Passive Income17:49 - Why DST Fees Run 8 to 12 Percent21:41 - Step Up in Basis and Estate Planning25:45 - Value the Property and Pull the Return27:36 - The Roth Mistake That Cost Me Years30:44 - Layered Taxes Hit Real Estate Hardest33:13 - The Third Door in the Tax Code35:29 - Four Steps to Price Your Exit37:41 - You Spend What Is Left Not Net WorthEscape 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/subscribeEpisode References & Resources:ℹ️ Who owns America's rentals - HUD / Census (2022) https://archives.hud.gov/news/2022/pr22-242.cfmℹ️ 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-wealthℹ️ Capital gains and the 25% recapture ceiling - IRS Topic 409 (2025) https://www.irs.gov/taxtopics/tc409ℹ️ Depreciation allowed or allowable - IRS FAQ (2025) https://www.irs.gov/faqs/sale-or-trade-of-business-depreciation-rentalsℹ️ Net investment income tax - IRS Topic 559 (2025) https://www.irs.gov/taxtopics/tc559ℹ️ Like-kind rules and the 45 and 180 day deadlines - IRS FS-2008-18 https://www.irs.gov/pub/irs-news/fs-08-18.pdfℹ️ 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/Support the podcast:⭐ Leave a rating & review📣 Share this episode with others✉️ Join the newsletter at https://escapetheclock.com/subscribeThis information is for educational purposes only and not financial advice. Consult a qualified professional for personalized guidance.#EscapeTheClock #EscapeTheClockPodcast #DanielCRodgers #1031Exchange #DelawareStatutoryTrust #RealEstateInvesting #PassiveIncome #CapitalGainsTax