A big real estate sale can create an even bigger tax bill, and that’s where Ashley Romiti steps in. She walks through how investors use a 1031 exchange to defer capital gains and depreciation recapture, what the “45 days to identify and 180 days to close” timeline really feels like in practice, and why many long-time owners eventually trade hands-on management for passive ownership through Delaware Statutory Trusts (DSTs). Eugene and Ashley also explore the gray areas developers run into, why investor intent matters, how DST restrictions shape risk and return, and what due diligence looks like when picking sponsors and properties. 

Guest Bio

Ashley Romiti is the founder of GCA 1031 and works with real estate investors who want to transition from active ownership into passive real estate investments using tax-deferred 1031 exchange strategies. She frequently uses DSTs as a fractional-ownership structure that can help investors pursue capital preservation and income while deferring capital gains and depreciation recapture. Ashley is a registered representative affiliated with a broker-dealer relationship through which these offerings are made. 

Episode Highlights and Chapters

00:00 Ashley’s niche: helping investors move from active ownership to passive investments using 1031 exchanges and DSTs 

02:54 A plain-English definition of the 1031 exchange and why taxes can be so painful on a sale 

06:01 The core timeline: 45 days to identify replacement property and 180 days to close 

06:27 What happens at death and how step-up in basis affects long-term strategy 

07:09 Development and 1031 exchanges: where the gray areas appear and why CPA guidance matters 

10:50 What a DST is, how fractional ownership works, and why “Delaware” is about the trust structure 

12:49 Why DST properties often concentrate in landlord- and tax-friendly states 

14:32 DSTs versus syndications, including how ownership and economics differ 

19:11 SEC framework and disclosures, including how offerings are presented and documented 

21:05 Sponsor incentives, exit decisions, hold periods, and DST rules that shape operational flexibility 

24:03 Where DSTs can fit for developers, including “takeout” concepts and solving for leftover exchange boot 

26:17 How Ashley screens deals: sponsor track record, fundamentals, structure, and investor goals 

30:20 Common DST asset classes today and why office remains challenging 

32:07 Typical minimums, accredited investor requirements, and diversification across multiple DSTs 

35:51 How to reach Ashley and where to download her 1031/DST ebook 

Contact Information

Ashley Romiti / GCA 1031 
https://gca1031.com
Free ebook available.
949-235-5606   

Host

Eugene Gershman / GIS Companies
https://giscompanies.co/

If you’re a developer or investor evaluating a deal, download Eugene’s free Feasibility Study Checklist to pressure-test assumptions, costs, timelines, and returns before you commit capital. If you’re interested in being a guest on the show, visit the podcast page to connect and apply.

https://giscompanies.co/podcast/

 

Ashley Romiti offers securities through Concorde Investment Services, LLC (CIS), member FINRA/SIPC. GCA 1031 is independent of CIS. Concorde is headquartered at 3909 Research Park Drive, Suite 200, Ann Arbor, MI 48108. This podcast is for informational purposes only, does not constitute as investment advice, and is not legal or tax advice. Please consult the appropriate professional regarding your individual circumstance.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.