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!

[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

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

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

Are you scared of losing tens of thousands to the IRS on your next property sale? Wondering if a 1031 exchange is really the secret weapon for building unstoppable cash flow… or just a headache waiting to happen?

This episode, Kenny Bedwell, no-fluff educator and the data-driven mind behind STR Insights, breaks down exactly how to prepare for a 1031 exchange the right way—using numbers, timelines, and real investor mistakes. From crushing the fear of tax bills to unlocking hidden strategies for short-term rental success, Kenny’s frank approach is full of hard truths and simple steps.

Listen now to sidestep costly errors, dodge timeline traps, and discover insider tactics you won’t hear anywhere else. Miss this episode, and you risk making one of the most expensive mistakes in real estate. Tune in while the stakes are high and every dollar counts!

[00:00] The hidden 1031 pitfalls that even experienced investors miss

[00:01:14] Why “waiting until closing” could wreck your 1031 dreams

[00:02:12] The shocking impact of capital gains—the numbers that matter now

[00:03:16] How to use the IRS rules to your advantage (and avoid a nightmare)

[00:05:13] The #1 reason most investors lose money on STR furnishings

[00:07:37] The uncommon truth about 1031 down payments and boot traps

[00:11:03] Kenny’s proven equity audit method: Should you sell or wait?

[00:14:04] Mapping your cash flow and equity for a powerful portfolio move

[00:16:50] When you should start hunting for your next market (spoiler: it’s not what you think)

[00:20:46] The 60-day strategy no one is teaching for stress-free 1031 shopping

[00:22:03] The risky world of reverse 1031 exchanges—what you must know

1. STR Scale Summit (event)
2. STR Insights software
3. IRS Section 1031 (1031 exchange rules)
4. QI / 1031 Intermediary services
5. Return on Equity (ROE) audit

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

Are you terrified of sinking your cash into a dying market or worse, following the herd off a financial cliff? In this masterclass episode, Kenny Bedwell rips the lid off his 2026 Top STR Markets Report, arming you with the real numbers, raw pitfalls, and hidden opportunities no one else will dare mention.

You’ll hear the unbiased, hard-hitting truth: where data says to buy, where strict regulations ruin even the prettiest towns, and razor-sharp strategies to squeeze maximum ROI in a landscape rocked by new rules and unpredictability. Kenny reveals not only the top 10 investable markets, but exactly why they’re worth your attention (and why some previous darlings are falling off).

Do not wait. Miss this, and you’re risking real money, real time, and watching your freedom slip away, while others secure the deals that change their financial destiny. This episode gives you numbers, biases called out, and actionable steps you won’t get anywhere else.

[00:01] – Why most “top STR market” lists are wrong (and what everyone’s missing)

[00:10] – The wild, thrilling impact of new regulations and market shakeups—this year’s biggest surprises revealed

[00:23] – Kenny’s ultra-candid red light, green light analysis: Where you really should be scared (and where to pounce)

[00:46] – The shocking climb of Mohican State Park and the overlooked cash cows in rural regions

[01:13] – Dirty little secrets behind high-grossing mountain and lake towns (and why access and permits matter more than hype)

[01:38] – Are you sitting on cash? Kenny reveals the uncommon ways budget transforms your deal-finding lens (with 4 ROI-driven categories)

[01:57] – How to beat city restrictions with region plays and advanced location hunting—no more bureaucratic land mines

[02:15] – The final, blunt warning: What happens if you listen to influencers over the data... and why you can’t skip this download

1. STR Scale Summit (event)
2. Airdna (STR market data)
3. BiggerPockets
4. Interview reference: "Part 2: How to make over $500k on one STR with Jeff Usner” episode, August/September 2024

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