Are you really leveling up or just running in circles with your real estate deals? If you’ve ever raced through a 1031 exchange, felt stuck chasing “passive” income that never arrives, or lost sleep over looming capital gains taxes, this episode is your game-changer.

Host Kenny Bedwell sits down with Brett Swarts, renowned capital gains tax strategist, for a blunt, numbers-driven masterclass on using Deferred Sales Trusts (DSTs) to crush the limitations of traditional 1031 exchanges and unleash truly passive income. Together, they dismantle common myths, reveal jaw-dropping case studies, and map out the step-by-step moves to reclaim your time, freedom, and cash flow.

Stop letting taxes and deadlines push you into the wrong deals. Listen now to discover how DSTs can hand you ultimate flexibility and real peace of mind. This exclusive episode is packed with proven strategies and insider tactics you won’t find anywhere else. Tune in now before you overpay for your next deal!

Timestamped Highlights

[00:00] – The moment that launched Brett’s obsession with beating capital gains taxes

[00:04:07] – Why “chasing 1031s” is making investors poor (and what to do first instead)

[00:07:45] – The “no-shoes, no-shirt, no problem” blueprint for replacing active headaches with true passive income

[00:09:19] – The killer move: How to actually “sell high, buy low” (and why 1031 jail kills your returns)

[00:12:39] – When you must set up your DST (miss this window and the tax man wins)

[00:15:31] – The shocking truth about 1031 “boot,” negotiation power, and not overpaying

[00:21:45] – Passive income math: The exact steps to multiplying your cash flow (with no toilets, trash, or termites)

[00:29:44] – How to reinvest, defer, and build wealth—without the dreaded time crunch

About the Guest

Brett Swarts is the founder and lead trustee at Capital Gains Tax Solutions. A nationally recognized expert in capital gains tax deferral strategies, Brett Swarts specializes in helping high net worth investors unlock growth, time freedom, and generational wealth through Deferred Sales Trusts. His practical approach has made him a trusted advisor to real estate entrepreneurs, business sellers, and anyone ready to escape the tax treadmill for truly passive income.

🔗 LinkedIn | Website

Resources Mentioned

Building a Capital Gains Tax Exit Plan (book by Brett Swarts)
Build it to Billions and Give More (podcast by Brett Swarts)
Cash Flow Quadrant (concept from Rich Dad Poor Dad)
Marcus & Millichap
Point Loma Nazarene University
William Jessup University

Important Links

Want us to find the deals for you? https://strinsights.com
Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df
Instagram – @kenny_bedwell
YouTube – Cash Flow Positive
LinkedIn – Kenneth Bedwell

Cash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.

Part 2: Brett Swarts - Preparing For A 1031 Exchange The Right Way