No More Tenants, Trash and Toilets: Ashley Romiti on DSTs and the 721 UPREIT

Ashley Romiti is the president and founder of GCA 1031, where she works primarily with retiring real estate investors who want to reposition their portfolios. Most of them have held their properties for a long time, and the hard part isn't the tax code. In her words: "The big thing they're giving up is control."

Ashley defines the 1031 exchange, the Delaware Statutory Trust and the 721 UPREIT, then walks through how she decides which one fits where an investor is. If you're still in growth mode, she'll tell you so: "I will be the first to tell a client, 'This is not for you.'"

What Ed and Ashley get into:

• How a 1031 exchange, a DST and a 721 UPREIT differ, and how they work together
• What an investor gives up in a DST: control and liquidity
• Why like kind is broader than most investors think
• Why a net lease property's value can drop as the lease term runs down
• The traditional DST's five to seven year hold, and the 721 DST's move into a REIT
• OP units, and the point where liquidity becomes a taxable event
• How DST debt can replace the loan you paid off in an exchange
• What 100 cold calls a day taught Ashley about rejection

Also in this episode, at 25:35, Questions from the Underground: The Personal Guarantee. An investor named Ronnie called Ed about a four-unit in Connecticut with six partners, none holding more than 20%, and his position was that nobody has to sign. Ed explains why that doesn't work, why the guarantee is really about how you responsibly use leverage, and why being worried about signing one is a warning sign.

This episode is general education on how these structures work. It is not tax, legal or investment advice. DSTs are illiquid and returns are not guaranteed. Talk to your own CPA and advisor about your situation.

Learn more about Ashley and GCA 1031 at gca1031.com.

Chapters:

• 00:00 Cold open: don't let one person have that much control over you
• 00:59 Welcome, Ashley Romiti of GCA 1031
• 01:56 Who Ashley works with: retiring investors repositioning a portfolio
• 03:12 Definitions: 1031 exchange, DST and 721 UPREIT
• 06:40 Like kind is broader than you think
• 06:59 What you give up in a DST: control
• 11:34 Growth or preservation: matching the vehicle to where you are
• 15:16 How the 721 UPREIT works
• 20:23 Debt replacement in a DST
• 23:35 1031 for growth, DST to land the plane, 721 for the estate
• 25:35 Questions from the Underground: The Personal Guarantee
• 30:07 Lightning round and where to find Ashley

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Additional Resources:

• Clark St Capital -> Passive real estate investments for busy business owners and executives
• Elevista -> AI SaaS for real estate investors
• Clark St Academy on YouTube -> Learn how to invest in real estate

Social Media:

• LinkedIn -> Ed Mathews (President at Clark St and Elevista)

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