Are you stuck waiting for the “big crash” to finally buy your dream short-term rental? What if that crash already came…and left you behind?

In this radically honest episode of Cash Flow Positive, host Kenny Bedwell brings on industry powerhouse Avery Carl for an unfiltered look at the post-pandemic real estate landscape. Avery Carl pulls from 10+ years and 5,000+ deals to reveal why smart investors are thriving while others are paralyzed by analysis, hype, and old strategies that simply don’t work anymore. If you want no-BS answers on timing the market, dealing with stubborn sellers, navigating high-interest rates, and finally making offers that actually win, you’ll find them here.

Don’t miss this straight-shooting, numbers-backed conversation with actionable takeaways for buyers AND sellers. Listen now to avoid the pain of missing out (again), capitalize on this rare window, and sidestep the false promises dominating today’s real estate noise. The market’s moving fast, and this episode is your roadmap to real victory.

[00:00] Startling confessions: Why the crash you’re waiting for already happened

[00:02:31] The brutal math on home prices—what truly stops them from falling

[00:03:39] Are you “catching a falling knife?” The secret cost of waiting for perfection

[00:07:51] How the offer game has totally changed (and hacks for today’s market)

[00:11:04] Real talk for sellers: Tough love, tough comps, and the biggest mistakes to avoid in 2024

[00:17:16] Stop buying ugly houses: Emotional pitfalls and winning tricks for higher resale value

[00:20:25] Beach access, views, and “turds with sprinkles”—what REALLY draws cash flow (and what kills it)

[00:26:48] The amenities arms race: At what point does “over-improving” backfire?

[00:33:36] Who’s buying next? The ignored risk that threatens every STR investor’s exit

1. Smarter Short Term Rentals – Facebook group
2. STR Scale Summit
3. BRRRR Strategy by David Greene
4. BiggerPockets

Avery Carl is the CEO and Founder of The Short Term Shop, the nation’s largest short-term rental-specific real estate brokerage. With more than 5,000 vacation rental transactions and 250+ personal investment doors, she’s a leading voice on how to think—AND act—smart in today’s unpredictable market. Avery’s blunt, data-backed advice and “own what works” mentality make her a must-follow for anyone serious about building wealth through real estate.

🔗 LinkedIn | Website

1. Want us to find the deals for you? https://strinsights.com

Are you sick of recycled guru advice and worried about making the wrong move in today’s wild STR market?

Kenny Bedwell cuts through the noise with brutal honesty and stark data, giving you the freedom to say no to hype and yes to cash-flow-positive deals.

In this punchy solo episode, he dives into the real state of the industry for 2026: how incentives twist advice you hear, why copycat “hotspots” will cost you big, and the practical innovations it takes to own your future profits. From dissecting shady vendor deals to revealing why being different is safer than ever, Kenny Bedwell arms you with rare, actionable insights.

Don’t get taken for a ride. Listen now to dodge avoidable disasters and seize proven, data-driven strategies you won’t find in the TikTok echo chamber. This is your unfair advantage, before the market leaves you behind.

[00:00] — The explosive problem with industry advice everyone ignores

[00:01:06] — Why “I just want to help” usually hides a dollar sign

[00:04:13] — The hidden motives that can quietly sink your next deal

[00:05:50] — Who’s selling short-term rental hope… and who’s selling hype?

[00:07:16] — The low-rate loan trap: what most investors miss before it’s too late

[00:10:04] — Realtor myths exposed: why those “best markets” rarely are

[00:11:01] — Overhyped markets vs. overlooked goldmines: what really works in 2026

[00:17:02] — The real shortcut to stand-out STR success (hint: it’s not more decor)

1. DSCR loans / second home loans
2. Airdna (indirect mention: short-term rental data providers)
3. STR Scale Summit
4. STR Wealth Con
5. ChatGPT (tool for creative brainstorming)
6. Wayfair (STR furnishing and amenity sourcing, referenced in context)

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

When’s the last time your calendar made you real money? Most hosts set their pricing, cross their fingers, and hope the bookings roll in… all while leaving thousands on the table and letting holidays sabotage their revenue.

In this actionable episode, Kenny Bedwell sits down with powerhouse educators Annette Grant and Sarah Karakaian from Thanks for Visiting to unpack how “mom and pop” operators can finally run their rentals like strategic businesses.

Packed with real-world tactics, this episode exposes costly blind spots in operations, team structure, and revenue management you can fix now. You’ll get proven approaches for transforming your calendar into a cash-generating asset, especially with high-risk holiday traps looming in 2026.

Listen now to skip overwhelm, outmaneuver your market, and grab the edge most hosts will miss. Wait, and you risk another year of margin-sucking mistakes… These battle-tested strategies are the difference between surviving and thriving, and you won’t hear them anywhere else.

[00:00] “You’re not running a business…you’re bleeding money”—the surprising mindset shift every STR host needs

[00:05:37] How to build your dream STR team (hint: it’s way more than a cleaner and remote lock)

[00:12:40] Panic pricing exposed! Why most hosts sabotage their revenue—and the wild fix you need

[00:16:05] The “Nashville hack” for algorithm dominance—how to rewrite your listings like a pro and win more visibility

[00:18:16] The untapped event strategy: Why a board game convention can outperform the Arnold Fitness event and what it teaches about true demand

[00:19:35] Squeeze every dollar from existing bookings—transforming “dead space” in your calendar into pure profit

[00:26:33] 2026’s high-risk holidays decoded: How a Friday July 4th or Christmas can kill (or skyrocket) your revenue if you’re not prepared

[00:32:36] Why revenue managers alone won’t save you—and the critical questions smart owners must ask to beat the competition

1. Thanks for Visiting Bootcamp
2. PriceLabs Market Dashboard
3. Airbnb
4. VRBO
5. Dynamic Pricing Tools (e.g., PriceLabs)
6. Arnold Fitness Expo
7. Board Game Convention (Columbus, OH)

Sarah Karakaian and Annette Grant are co-founders of Thanks for Visiting, the revered short-term rental education brand helping thousands of hosts maximize profit and hospitality through operations excellence. As STR investors, property managers, and top trainers, they’ve coached hosts...