DST vs 1031: The Tax-Deferred Option No One Explains | With Taylor Ashland

DST vs 1031: The Tax-Deferred Option No One Explains | With Taylor Ashland

From Commercially Speaking Podcast- Commercial Real Estate Investing That Entertains by Bo Barron, CCIM | Timmy Barron, ADHD

February 3, 2026 · 1h 20m · Season 4 · Episode 4

About this episode

This episode discusses the advantages of Delaware Statutory Trusts as an alternative to 1031 exchanges for tax deferral in real estate investing.

If you sell an investment property and want to defer taxes, a 1031 exchange is usually the answer. But there’s a problem no one likes to talk about: You only have 45 days to identify a replacement property. That pressure often leads investors to overpay, settle for deals they don’t love, or rush into more active management when they were actually trying to slow down. In this episode of Commercially Speaking , we sit down with Taylor Ashland , founder of Ashland Pacific , to explore Delaware Statutory Trusts (DSTs) as a 1031-eligible alternative. DSTs allow investors to: ​Defer capital gains and depreciation recapture taxes ​Invest passively in institutional-quality real estate ​Avoid the 45-day scramble to identify a property ​Eliminate active management and tenant headaches We break down: ​How DSTs actually work inside a 1031 exchange ​Why the 45-day window creates bad incentives ​When a DST makes sense (and when it doesn’t) ​Loss of control, lack of liquidity, and real risks ​How DSTs can be a full exit strategy or a “supporting actor” ​Why brokers don’t get paid on DSTs (and why that matters) ​The emotional side of money, taxes, and decision-making This episode is not tax or…

More episodes of Commercially Speaking Podcast- Commercial Real Estate Investing That Entertains

Explore listener stats, chart rankings, contacts and more on the Commercially Speaking Podcast- Commercial Real Estate Investing That Entertains podcast page.