Chalkboards to Cashflow: Educators Investing in Real Estate

What happens when a teacher decides that the classroom is no longer enough to create the financial freedom they want?

In this episode, we sit down with AJ Mata, a former educator who transitioned from teaching into real estate investing and went on to build a career spanning real estate brokerage, flipping, development, appraisal, and education.

AJ shares the honest story behind his decision to leave teaching, the risks he took when getting started, and the long road to his first real estate deal.

His first wholesale deal took approximately 11 months to close and generated around $6,000, after starting with just $127 for marketing, gas, and food. He also opens up about some of the decisions he would do differently today, including spending approximately $20,000 on a real estate course and leaving teaching before he was financially ready.

Most importantly, AJ explains why teachers thinking about making the same transition should slow down before quitting. Looking back, he says he would have stayed in teaching for another two or three years while building his real estate knowledge and business.

Today, AJ is using his experience to help others navigate real estate through Thrive With AJ, a practical real estate education and mentorship platform.

IN THIS EPISODE

• AJ's journey from teacher to real estate investor

• Why financial limitations became a major concern as an educator

• The personal event that pushed AJ to reconsider his career

• The risks AJ took when getting started in real estate

• Why he spent approximately $20,000 on a real estate course

• Going six months without making money

• How AJ made his first $6,000 wholesale deal

• Why his first deal took approximately 11 months

• The reality of real estate investing as a long game

• Why AJ says he would have stayed in teaching longer

• His first house flip

• Becoming a licensed real estate agent

• Building his own brokerage

• The creation of Thrive With AJ

• Why practical experience matters in real estate education

ABOUT THE GUEST

AJ Mata is a former teacher who transitioned from education into real estate investing and entrepreneurship.

After beginning his career as a sixth-grade language arts and reading teacher, AJ became increasingly interested in entrepreneurship and real estate. He eventually made the transition into real estate, learning about wholesaling, flipping, development, and investing.

His real estate career continued to expand. He obtained his real estate license in 2017 and became a real estate broker in 2020. He also developed experience in home building, real estate appraisal, and insurance-related work.

AJ later launched Thrive With AJ, an education and mentorship platform designed to help people understand real estate through practical steps rather than theory alone.

His approach combines his experience as an educator with his experience actually working in real estate. The goal is to help individuals identify the real estate strategy that fits their circumstances rather than treating investing as a one-size-fits-all path.

Connect With AJ Mata

Instagram: @thrivewithaj

LinkedIn: https://www.linkedin.com/in/realestatewithaj/?utm_source=chatgpt.com&original_referer=https%3A%2F%2Fwww.google.com%2F

Connect With The ShowFollow Chalkboards to Cash Flow for more conversations around real estate, side hustles, and financial freedom for educators.Join the free Chalkboards to Cash Flow Facebook community and connect with teachers and everyday investors building wealth one step at a time. Enjoyed This Episode?If this episode inspired you to explore real estate while continuing your teaching career:* Follow the podcast* Leave a review* Share this episode with another educator* Join the Chalkboards to Cash Flow Facebook group* Reach out on Instagram for more information about becoming an agentBecause you don’t have to leave the classroom to start building wealth outside of it.

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 mid-term housing.

Today, she shares the real-world lessons behind her experience, including how she found tenants, what she charges, how she handles living under the same roof as renters, and what she learned from both great and challenging tenant experiences.

She currently earns $1,200/month from one room, including utilities, Wi-Fi and streaming services. She says she has experienced consistent occupancy, with every month occupied aside from time she intentionally chose not to rent.

What You'll Learn

In this episode of Chalkboards to Cash Flow, you'll learn:

• 🏠 How to turn an empty bedroom into monthly income without owning a large real estate portfolio.
• 💰 How Shauna reached $1,200/month renting out a single room.
• 🩺 How mid-term rentals work and why traveling professionals can be potential tenants.
• 🔐 How to approach tenant screening and create a safer rental experience.
• 📅 Why starting with a shorter lease can give both the host and tenant flexibility.
• 📸 How to create a rental listing that gets attention, from photos and titles to a complete profile.
• 💵 How to think about rental pricing while accounting for utilities and seasonal costs.
• 🛏️ Which upgrades can improve the rental experience, including flooring and mattresses.
• ⚠️ What can go wrong when living with tenants and lessons from a challenging rental experience.
• 👩‍🏫 How a retired teacher approached house hacking without a traditional real estate investing background.
• 🧠 Why your personality and lifestyle matter when deciding whether renting a room is right for you.
• 🚪 How to decide whether sharing your home with tenants actually works for you.

About the Guest

Shauna is a retired elementary school teacher with 36 years of teaching experience, including 25 years in the Roseville area. After her children moved out, she found herself with extra bedrooms in her four-bedroom home and began exploring how she could turn that unused space into additional income.

She eventually began renting rooms to traveling professionals through Furnished Finder, with many of her early tenants being travel nurses. Over time, she has also hosted professionals including a pilot and an anesthesiologist completing an internship.

Today, Shauna earns $1,200 per month from one room, with utilities, Wi-Fi and streaming services included in the rental price. She shares the practical lessons she's learned about tenant screening, pricing, creating a compelling rental listing, managing shared living spaces and choosing the right tenants.

Her story offers a practical look at how homeowners with unused space can explore mid-term rentals and house hacking without owning a large real estate portfolio.
Connect With The ShowFollow Chalkboards to Cash Flow for more conversations around real estate, side hustles, and financial freedom for educators.Join the free Chalkboards to Cash Flow Facebook community and connect with teachers and everyday investors building wealth one step at a time. Enjoyed This Episode?If this episode inspired you to explore real estate while continuing your teaching career:* Follow the podcast* Leave a review* Share this episode with another educator* Join the Chalkboards to Cash Flow Facebook group* Reach out on Instagram for more information about becoming an agentBecause you don’t have to leave the classroom to start building wealth outside of it.

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, unrealistic, or simply "crazy." But your environment can dramatically change what's possible.

This episode breaks down the role that education, community, relationships, and accountability have played in the hosts' real estate journey, from learning short-term rentals to exploring boutique hotels and micro-resorts.

You'll hear about three different investing communities they joined, what each one taught them, and why the right community at the right stage can be just as valuable as the property itself.

Most importantly, you'll learn why you don't have to figure out real estate investing alone.

Proximity changes what's possible.

In This Episode, You'll Learn

• Why friends and family may not understand your real estate goals

• The difference between an "impossible dream" and a series of actionable steps

• Why surrounding yourself with experienced investors can accelerate your learning

• How education can help you avoid expensive mistakes

• What the hosts learned from the Alpha Host Academy community

• Why relationships can become more valuable than the education itself

• How one real estate community eventually led to a business partnership

• What changes when you move from short-term rentals into boutique hotels

• Why hotel underwriting is different from analyzing a short-term rental

Connect With the Community

If you're a teacher, nurse, W-2 professional, or aspiring investor looking to learn real estate and connect with others on the same journey, check out the Chalkboards to Cash Flow community.

You don't have to figure this out alone.

If this episode helped you, follow Chalkboards to Cash Flow, leave a review, and share the episode with someone who needs to hear it.

You can also join the free Chalkboards to Cash Flow Facebook community and connect with other investors.

Listen, Follow & Share

Feeling like you don’t have enough time to invest, build a side hustle, or work toward financial freedom?

In this episode of Chalkboards to Cash Flow, we tackle one of the biggest obstacles teachers, W-2 professionals, parents, and busy professionals face: “I don’t have time.”

The reality is that life comes in seasons. Some weeks give you plenty of flexibility, while others—like the first few weeks of a new school year—can consume almost all of your attention. The key isn’t waiting for a magically free schedule. It’s learning how to keep moving forward when you have less time.

You’ll learn why you don’t need to analyze ten properties, attend every meetup, or spend hours every week on your investing goals. Sometimes, 30 focused minutes or one small action is enough to keep the momentum going.

In This Episode:

• Why busy seasons can completely derail your investing goals

• The danger of turning your side hustle into another job

• Why you don't need to be productive every single week

• How to recognize and work with different seasons of your life

• Why consistency over years matters more than one perfect month

• How to gradually rebuild your investing routine after a busy period

• Practical ways to make progress with limited time

• Why analyzing one property can be better than waiting to analyze ten

• The “pick one thing” approach to staying on track

• How to start again when you've fallen behind

The Big Takeaway

You probably won't suddenly find an extra 20 hours in your week.

Instead of waiting for more time, learn how to keep moving with the time you actually have.

Analyze one property. Listen to one call. Contact one investor. Attend one meetup. Put $100 into your investment account.

Something small is better than waiting for the perfect time to do everything.

Connect with Chalkboards to Cash Flow

📘 Join our Facebook Community to connect with educators and investors learning how to build wealth through real estate.

Subscribe for more conversations with investors, entrepreneurs, and financial experts helping educators and professionals build wealth, create cash flow, and make smarter investment decisions.

👍 Like, Comment & Subscribe for more episodes on real estate investing, passive income strategies, financial freedom, and building long-term wealth.

Disclaimer

This episode shares personal real estate investing experiences and educational insights. Landlord-tenant laws vary by location, so consult a qualified professional for advice specific to your situation.

Thanks for listening to Chalkboards to Cash Flow, the podcast for teachers and W-2 professionals building wealth and creating options beyond their paycheck.

You don't need to be rich to start. You just need to start.

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-bedroom, 3-bath property in Pigeon Forge and a 2-bedroom, 2-bath property in Sevierville. She also shares what it was like buying both properties sight unseen and learning the short-term rental business as she went.

Timestamps

00:00 — From teacher to short-term rental host

00:56 — Why Michelle moved away from long-term rentals

01:28 — Using a 1031 exchange to buy two Tennessee rentals

02:05 — Buying short-term rentals sight unseen

03:03 — Why Pigeon Forge is a strong vacation rental market

03:28 — Listing the properties on Airbnb and Vrbo

03:48 — Learning how to run a short-term rental

04:22 — Comparing long-term vs. short-term rental income

04:58 — The reality of seasonality

06:17 — Why short-term rentals aren't passive

07:10 — Smart locks and rental automation

07:33 — Using dynamic pricing with PriceLabs

08:30 — Automating guest communication

09:31 — Why your cleaner can make or break your rental

10:32 — Why short-term rentals can work for teachers

11:02 — Flexible cash flow and getting started with your own property

11:59 — Final thoughts and community invitation

In This Episode, You’ll Learn:

• Why Michelle decided to move from long-term rentals to short-term rentals

• How a short-term rental can potentially generate more revenue than a traditional long-term rental

• How she used a 1031 exchange to move from one rental property into two short-term rentals

• The realities of buying investment properties sight unseen

• Why seasonality is one of the biggest factors to understand in short-term rentals

• Why short-term rentals are not truly passive investments

• How automation helped reduce the amount of guest communication

• The tools she uses for smart locks, dynamic pricing, and automated guest messaging

• Why finding the right local cleaner can make or break your rental

• Why short-term rentals can be a flexible strategy for teachers and educators

• How teachers can potentially start with a room or guest house on their own property

Key Takeaway

Short-term rentals can create significantly more cash flow than long-term rentals, but higher revenue comes with more responsibility. From managing guests and cleaners to understanding seasonality and pricing, success requires systems, automation, and a strong local team.

For teachers, Michelle believes the strategy can be especially appealing because the seasonal nature of short-term rentals can align with the school calendar—giving educators an opportunity to build additional income while maintaining their careers.

Connect With The ShowFollow Chalkboards to Cash Flow for more conversations around real estate, side hustles, and financial freedom for educators.Join the free Chalkboards to Cash Flow Facebook community and connect with teachers and everyday investors building wealth one step at a time.You don't need to be rich to start. You just need to start.

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 secretly sublet the property to someone who was never screened or approved. When rent eventually stopped, California's tenant protections made it extremely difficult to regain control of the property. The situation escalated into months of lost rental income, legal expenses, property damage, stolen furniture and appliances, and a massive cleanup.

This experience completely changed the way she approached real estate investing.

In this episode, you'll learn why long-term rentals aren't always passive income, why understanding local landlord-tenant laws matters, and how stronger tenant screening and lease protections can help protect your investment. You'll also hear why this experience eventually pushed her toward short-term and mid-term rentals, where she felt she had greater tenant control and a more proactive investment strategy.

Timestamps

00:00 — The rental decision that started it all

01:45 — The tenant secretly sublets the property

02:42 — How the unauthorized occupant got into the house

02:51 — Rent stops and the landlord gets trapped

03:00 — Why removing the occupants became so difficult

04:00 — The damage, stolen property, and mounting costs

05:00 — The hard lesson that changed everything

06:17 — Why short-term and mid-term rentals became appealing

06:24 — Lessons for teachers and first-time investors

07:38 — What happened next

What You'll Learn

• Why a seemingly great tenant can still become a major risk

• The dangers of unauthorized subletting

• Why landlord-tenant laws can dramatically affect your investment

• How tenant issues can create unexpected legal and financial costs

• Why valuable furniture and appliances may not belong in a rental property

• The importance of thorough tenant screening

• Lease terms every landlord should think carefully about

• Why rental properties should be treated as business assets

• How one difficult experience led to exploring short-term and mid-term rentals

• Why real estate investing requires ongoing involvement—not a “set it and forget it” mindset

Key Takeaway

A rental property isn't simply a source of passive income. It's a business, and protecting that business requires preparation, strong systems, careful screening, and an understanding of the laws where you invest.

This story is a reminder that learning from someone else's expensive mistake can save you from making the same one yourself.

Connect with Chalkboards to Cash Flow

If you're a teacher or first-time investor considering renting out your property, this episode is one you won't want to miss.

📘 Join our Facebook Community to connect with educators and investors learning how to build wealth through real estate.

Subscribe for more conversations with investors, entrepreneurs, and financial experts helping educators and professionals build wealth, create cash flow, and make smarter investment decisions.

Like, Comment & Subscribe for more episodes on real estate investing, passive income strategies, financial freedom, and building long-term wealth.

Disclaimer: This episode shares personal real estate investing experiences and educational insights. Landlord-tenant laws vary by location, so consult a qualified professional for advice specific to your situation.

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 starting over at 44. From depreciation and repairs to furnishings and other expenses, the episode explores how an STR can become more than a side hustle—it can be part of a long-term wealth-building strategy.

Timestamps

00:00 – Welcome to Episode 20: The STR Tax Loophole

00:23 – How an Airbnb can potentially save you thousands in taxes

00:58 – What is the STR loophole?

01:42 – Depreciation, repairs, furnishings & tax deductions

02:11 – Michelle's personal wealth-building journey

02:46 – Key requirements to qualify

03:18 – The importance of average guest stays under 7 days

03:18 – Understanding material participation

03:59 – The 100-hour and 500-hour tests

04:29 – Recordkeeping and what the loophole doesn't do

05:01 – Why the strategy can be a game changer for W-2 earners

05:26 – Building wealth beyond the classroom

05:54 – Connect with Chalkboards to Cash Flow

In This Episode, You'll Learn:

• What the STR loophole is and why it can be especially valuable for W-2 earners

• How short-term rental income and losses may be treated differently from traditional rental income

• The importance of having an average guest stay under seven days

• What material participation means

• The IRS participation tests discussed in the episode

• Examples of activities that may count toward material participation, including guest messaging, cleaning, repairs, restocking, calendar management, and marketing

• Why keeping detailed records of your hours, expenses, and receipts matters

• How using a property manager can affect your ability to meet participation requirements

• What the STR loophole does—and does not—do

• Why this strategy should be approached with guidance from a qualified, real-estate-savvy tax professional

The STR loophole isn't simply about avoiding taxes or making quick money. When the applicable IRS requirements are met, it can potentially allow qualifying investors to use certain rental losses against active income. For teachers and other W-2 professionals, that can make short-term rentals a powerful tool for building wealth beyond a traditional paycheck.

Disclaimer: This episode is educational and does not constitute tax or financial advice. Always consult your CPA or qualified tax professional before implementing any tax strategy.

Connect With The ShowFollow Chalkboards to Cash Flow for more conversations around real estate, side hustles, and financial freedom for educators.Join the free Chalkboards to Cash Flow Facebook community and connect with teachers and everyday investors building wealth one step at a time.You don't need to be rich to start. You just need to start.

What does it really cost to launch a successful Airbnb?

Many investors focus on buying the property but underestimate everything that happens afterward. From furniture assembly and logistics to design execution, vendor management, and photography, the setup phase can make or break your investment.

In this episode of Chalkboards to Cash Flow, we sit down with Victor Rendon, Founder of Space Launch LLC, to uncover the hidden costs and common mistakes investors make when setting up short-term rentals—especially when investing out of state.

Michelle also shares her personal experience working with Space Launch on one of her Smoky Mountains properties and explains why having the right installation team saved both time and money.

Whether you're buying your first Airbnb or scaling a portfolio across multiple states, this episode is packed with practical advice that could save you thousands of dollars and weeks of delays.

What You'll Learn

• Why most investors underestimate Airbnb setup costs

• The biggest mistakes remote Airbnb investors make

• Why professional installation is more than just furniture assembly

• How design impacts bookings and revenue

• The importance of sticking to your design plan

• How logistics and warehousing simplify remote investing

• Why cheap contractors can cost you more in the long run

• The role of procurement in avoiding costly delays

• Why professional photography is one of the best investments you can make

• Tips for first-time Airbnb investors

  
  

Connect with Our Guest

🌐 Space Launch LLC: https://spacelaunchllc.com/

Connect with Chalkboards to Cash Flow

📘 Join our Facebook Community

📸 Follow us on Instagram: @chalkboardstocashflow

Subscribe for more conversations with investors, entrepreneurs, and financial experts helping educators and professionals build wealth through real estate.

👍 Like, Comment & Subscribe for weekly episodes on

How to buy houses below market value and profit multiple ways from one deal with Houston investor agent Eduardo on Chalkboards to Cash Flow. In this episode, Eduardo breaks down how to find off market real estate deals through wholesalers, how hard money lenders fund up to 70% of ARV including rehab costs, and how to start real estate investing with $20K using the BRRRR strategy. He also shares why design increases property value, how W2 professionals and teachers can invest in real estate part time, and the truth about passive income.

🌐 Facebook: https://www.facebook.com/p/The-Bisbal-Group-61578955659456/📱 Instagram: @investstyleco📞 Phone: (832) 586-6759If you're looking to invest in the Houston market or want guidance on finding profitable investment properties, Eduardo is happy to connect and answer your questions.Connect with Chalkboards to Cash Flow📘 Join our Facebook Community📸 Follow us on Instagram: @chalkboardstocashflowSubscribe for more conversations with investors, entrepreneurs, and financial experts helping educators and professionals build wealth through real estate.Like, Comment & Subscribe for weekly episodes on real estate investing, passive income strategies, financial freedom, and building long-term wealth.

Chalkboards to Cash Flow

Most people think retirement is the end of building wealth. Richard proves it's just the beginning.

In this episode of Chalkboards to Cash Flow, host Michelle Chavannes sits down with Richard, a former electrical engineer and longtime W2 employee who retired at 55 and transformed his financial future through alternative investments, passive income strategies, digital marketing, and real estate.

Richard shares his journey from working at Lockheed Martin to building multiple income streams through apartment syndications, assisted living investments, oil & gas projects, online businesses, and community building. He also discusses the importance of financial planning, diversification, and why retirement should be viewed as an opportunity for growth rather than slowing down.

Whether you're approaching retirement, looking for financial freedom, or simply want to create additional income streams, this episode is packed with practical insights and inspiration.

What You'll Learn:

✅ How Richard retired early at 55

✅ Why relying solely on a 401(k) may not be enough

✅ Alternative investments retirees should consider

✅ What to look for before investing in passive real estate deals

✅ The importance of due diligence and diversification

✅ How digital marketing creates additional income streams ✅ Why retirees should embrace AI and online opportunities ✅ Strategies for building wealth beyond a traditional job

Key Takeaways:

• Retirement doesn't mean shrinking your life—it can mean expanding it.

• Diversification is essential for long-term financial security.

• Passive income can help bridge the gap between retirement and traditional retirement benefits.

• Digital marketing and online businesses offer opportunities at any age.

• It's never too late to start building wealth.

  Connect with Richard

  📧 Email: [email protected]

  Connect With The Show

  Follow Chalkboards to Cash Flow for more conversations around real estate, side hustles, and financial freedom for educators.

  Join the free Chalkboards to Cash Flow Facebook community and connect with teachers and everyday investors building wealth one step at a time.