HeyJaredChalkboards to Cashflow: Educators Investing in Real Estate
🎙️ Welcome to: Chalkboards to Cashflow! 🏠📚- The podcast for educators ready to build wealth through real estate.
- Indexed episodes, last 90 days
- 9
- Latest publication
- Sep 22, 2026
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- Earliest in this view
- Jul 9, 2026
Latest episodes
She Turned Empty Bedrooms Into $1,200/Month (opens the original)
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What if the empty bedroom in your house could generate $1,200 a month? In this episode of Chalkboards to Cash Flow , we sit down with Shauna, a retired elementary school teacher who discovered a way to turn the unused bedrooms in her four-bedroom home into monthly income. After her children moved out, Shauna realized she had extra space sitting unused. She began renting rooms to traveling professionals through Furnished Finder , primarily serving travel nurses and other professionals looking for
The Biggest Mistake New Real Estate Investors Make (opens the original)
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What if the biggest mistake new real estate investors make has nothing to do with buying the wrong property? In this episode of Chalkboards to Cash Flow , we explore one of the most overlooked advantages in real estate investing: getting in the room with people who are already doing what you want to do. When you start investing—or decide to move from short-term rentals into larger assets like boutique hotels—it can be easy to listen to friends and family who think your goals are too risky, unrea
How a Teacher Turned Rentals Into Bigger Cash Flow (opens the original)
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What happens when a full-time teacher realizes her long-term rental properties could generate significantly more cash flow as short-term rentals? In this episode of Chalkboards to Cash Flow, Michelle shares how she transitioned from long-term rentals to Airbnb and VRBO hosting—and built a short-term rental strategy around her career as an educator. Michelle walks through how she sold a California long-term rental and used a 1031 exchange to purchase two short-term rentals in Tennessee: a 3-bedro
One Tenant Changed How I Invest Forever | Ep 21 with Michelle kavan (opens the original)
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What happens when a seemingly perfect tenant turns your rental property into a legal, emotional, and financial nightmare? In this episode of Chalkboards to Cash Flow , we hear the personal story of a real estate investor who learned this lesson the hard way. After moving into a new home, she decided to rent out her previous California property. The tenant appeared ideal—good credit, polite, quiet, and consistently paying rent. But behind the scenes, the situation was about to unravel. The tenant
The Secret Tax Advantage of Owning an Airbnb (opens the original)
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What if your Airbnb could do more than generate extra income—it could potentially help reduce your taxable income? In Episode 20 of Chalkboards to Cash Flow , we break down the Short-Term Rental (STR) loophole and explain how teachers and other W-2 earners may be able to use short-term rental losses to offset active income when they meet the IRS requirements. As a full-time public school educator, Michelle shares how she personally used this strategy while rebuilding her financial future after s
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