in a short-term rental?

This episode will shake you out of indecision and challenge everything you thought you knew about market timing. Kenny Bedwell, founder of STR Insights, goes straight to the heart of opportunity cost, showing how hesitation can quietly devastate your wealth, your tax savings, and even your freedom.

Packed with frank, numbers-backed stories and actionable logic, Kenny breaks down why waiting for “the perfect market” is an investor’s biggest mistake and how missed months equal missed thousands. If you’re tired of guru hype and ready for practical data-driven education, tune in now. The longer you wait, the more you lose.

Listen today to avoid costly inaction and gain exclusive insight no algorithm or “expert” will give you. This episode is your wake-up call.

[00:00] – Why “timing the market” is just a myth (no crystal ball needed)

[00:02:42] – The shocking truth about real estate crashes and market cycles

[00:05:07] – The finite supply of “good deals” and how STR seasonality affects your shot

[00:07:18] – Real-life regret: Kenny’s confessions about not acting faster during COVID

[00:08:33] – How opportunity cost quietly steals your cash flow every missed month

[00:12:42] – Tale of two investors: Who wins and why taking action fuels exponential growth

[00:16:47] – “Ugly” puzzle properties: Why complexity signals massive upside

[00:22:17] – The secret to unlocking deals others fear (and how Kenny found a jackpot)

[00:23:30] – Kenny’s final brutal advice: Only act when you really have the means

1. Goldman Sachs – Market rate forecast reference
2. Proper, Steadily – Insurance companies for STRs
3. Watkins Glen lottery system (STR permitting example)
4. Bonus depreciation (tax strategy for STR buyers)

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.