Commercially Speaking

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 headachesWe 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-makingThis episode is not tax or legal advice. It’s a practical, honest conversation about options most investors don’t hear until it’s too late. The information discussed in this podcast is for informational purposes only and does not constitute investment advice or an offer to buy or sell any securities. Investing in real estate and 1031 exchange replacement properties may not be suitable for all investors and may involve significant risks. All opinions expressed are those of the speaker and are subject to change without notice. Listeners should consult their own financial professionals before making any investment decisions. Ashland Pacific is a branch office of DFPG Investments, LLC. Securities offered through DFPG Investments, LLC. Member FINRA/SIPC. Investment Advisory Services offered through Diversify Advisory Services, LLC. Ashland Pacific is not affiliated with DFPG or Diversify. Thanks To Our Sponsors ​💰🏙️ CRE Investor Coach: No Guess Work, No Wasted Time — https://cre-investor-coach.mykajabi.com/a/2148133410/9YMWzNXy​🤖 Superpowers HQ – Need a CRE executive assistant? Get one here: superpowershq.com/commerciallyspeaking🎧 Learn more about Taylor: ​https://shepherdingyourwealth.com​https://ashpac.com​Instagram: @taylordesmondashland📺 Subscribe for more conversations on real estate, investing, negotiation, and buying back your time. And yes, Barbara Corcoran… still standing by. 00:00 – The 45-Day Problem With 1031 Exchanges Why rushed timelines force bad decisions 05:30 – Why Investors Overpay in 1031s Incentives brokers love and sellers hate 10:40 – What Is a Delaware Statutory Trust (DST)? Plain-English explanation 18:30 – How DSTs Qualify for 1031 Exchanges Beneficial interests, not partnerships 27:00 – Passive Real Estate Without Management No tenants, no toilets, no calls 34:45 – Loss of Control & Liquidity (The Real Risks) Why DSTs are not for everyone 42:20 – Using DSTs as a Supporting Actor Solving “boot,” debt replacement, and leftover equity 52:10 – Why Brokers Don’t Get Paid on DSTs The incentives nobody explains 01:01:30 – Emotional Decision-Making in Investing Why numbers alone aren’t enough 01:12:00 – Who a DST Is Actually For Ideal scenarios and red flags 01:22:30 – Final Takeaways More options, better decisions