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
2. Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df
3. Instagram – @kenny_bedwell
4. YouTube – Cash Flow Positive
5. 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.