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

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 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.

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🎧 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