Ashley Romiti serves as Founder and President of GCA1031, who specializes in helping long-term real estate investors navigate the often-overlooked side of investing: the exit. With nearly 15 years in commercial real estate underwriting and advisory, Ashley saw too many retiring landlords and business owners sitting on highly appreciated assets, facing management fatigue and major tax exposure—without fully understanding their options. She breaks down how 1031 exchanges and Delaware Statutory Trusts (DSTs) actually work, how to evaluate risk and income beyond headline returns, and how to transition from active ownership to passive income while preserving capital and deferring taxes. If you’re a seasoned investor thinking about selling, scaling back, or building a smarter long-term wealth plan, this conversation brings clarity to one of the most important (and misunderstood) decisions you’ll make.

In this episode, you will be able to:

• Understand how a 1031 exchange works an...

From studying tax law at just 14 years old to landing her dream job inside the IRS, Carlotta Thompson seemed destined for a lifelong career in government. But once she stepped behind the curtain as an IRS auditor, she discovered something shocking: countless business owners were leaving hundreds of thousands of dollars on the table in missed deductions — and the system wasn’t built to help them. 

Realizing she was “on the wrong side,” Carlotta walked away from the IRS to pursue a bigger mission: help entrepreneurs pay the least amount of tax legally possible. Today, as the Founder & CEO of Tax Strategists of America, she leads business owners through her signature Pathway to Zero™ program — a proven framework that uncovers hidden deductions, maximizes tax strategy, and empowers owners to keep more of what they earn. 

In this episode, Carlotta reveals the truths she learned inside the IRS, the most common (and costly) mistakes business owners make, and the practical steps entrepr...