Episode 8: Should You Start With Long-Term or Short-Term Rentals?

Why This W2 Employee Ditched Corporate for Real Estate | Ep 17 with Richard Dias

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: Richard@dailypaywithrich.com 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.

Ep 16 Make More Money With What You Already Own | with Jennifer Mead

What if the land, home, garage, or even driveway you already own could become a source of income? In this episode of Chalkboards to Cash Flow, host Jennifer Mead shares creative and practical ways educators and everyday homeowners can generate income through real estate—without necessarily buying more properties.Jennifer explains how co-living works, why it helps solve housing challenges, and how renting individual rooms can dramatically increase cash flow. She also shares lesser-known opportunities for making money from land, garages, driveways, storage space, RV parking, recreational leasing, and more.Whether you're a teacher looking for a side hustle, a homeowner with unused space, or someone interested in real estate investing, this episode is packed with actionable ideas you can start exploring today. In this episode: Jennifer Mead shares how she transitioned from business ownership and substitute teaching into real estate investing, explains the co-living strategy that's helping create affordable housing while boosting cash flow, and reveals creative ways to generate income from extra rooms, garages, driveways, RV spaces, and vacant land. She also discusses the importance of networking, finding the right business partners, leveraging local real estate communities, and taking action with the resources you already have to start building wealth through real estate. 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. You don't need to be rich to start. You just need to start.

Ep 15: From STR Owner to Community Builder – How Anastasia Built Multiple Short-Term Rentals

What if one short-term rental turned into multiple, and then turned into a movement? In this episode, we sit down with Anastasia, who went from a Google employee with zero tax deductions to owning 7 short-term rental properties across Orlando, Hawaii, and Broken Bow, Oklahoma, with plans to hit 9 by the end of the year. Anastasia shares how a tax textbook changed everything, why she was initially resistant to mentors (and why that almost held her back), and how she built a remote team of cleaners, handymen, and inspectors to manage properties she doesn't live near. She also opens up about her toughest lessons, including her first STR purchase during COVID, and the emotional guest story that reminded her why she does this work. We also talk about how she's now building a community to help other investors, especially those in tech, learn the tax strategies and systems she wishes someone had taught her years ago. In this episode: * How a single book sparked her real estate journey * Building remote teams across multiple states * Comparing guest expectations across different markets * Why she was scared to start a community, and did it anyway * Her advice for first-time STR investors Follow Anastasia on Instagram: https://www.instagram.com/root_investmentsEmail - anastasia@rootinvestmentproperties.comJoin us in the Chalkboards to Cash Flow community and follow us on Instagram @chalkboardstocashflow

Episode 14: Why This Nurse Quit Flipping Houses to Buy Hotels Instead

Lorenzo, a full-time nurse at Stanford, found out the hard way — title issues, maxed-out credit cards, a hard money loan coming due, and buyers who backed out at the last minute. But instead of quitting, he used the lessons from 3 flips to pivot into something bigger: boutique nature hotels. In this episode of Chalkboards to Cash Flow, Lorenzo breaks down exactly what went wrong, why he quit flipping for good, and how a W-2 nurse is now raising capital to buy his first hotel in California. In this episode: Why Lorenzo blew all his money before getting serious about investing The $100K loss on his first flip — and what caused it The title company mistake that nearly destroyed the deal Why flipping doesn't build wealth as fast as you think How to partner with the right people (and why it's like marriage) Why he quit flipping after just 3 deals His hotel buy box: 10–20 rooms, nature-focused, under $5M How he manages real estate while still working as a nurse The power of community and masterminds for W-2 investors Connect with Lorenzo: Instagram: https://www.instagram.com/lorenzo.mercado_ Website: LorenzoMercado.com | SolvarraGroup.com  Podcast: https://podcasts.apple.com/us/podcast/the-lo-down/id1764777761  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. You don't need to be rich to start. You just need to start.

Episode 13: Teacher By Day, Realtor By Night

In this episode of Chalkboards to Cash Flow, we sit down with Lindsay, a full-time first grade teacher who has successfully balanced a career in education while working as a licensed real estate agent for more than two decades. From juggling lesson plans and client calls to using commission checks to support her family and retirement goals, Lindsay shares the reality of managing two careers at once and why becoming a real estate agent can be a powerful side hustle for educators. If you’ve ever wondered whether you could build a real estate career without leaving the classroom, this episode is for you. In This Episode, We Cover: * How Lindsay became a real estate agent while teaching full time * Balancing education, family life, and real estate * Why teaching skills translate well into real estate * The realities of earning commission-based income * Using real estate as supplemental retirement income * Challenges of managing two careers * Building trust with clients while working in education * Why educators may have an advantage in real estate Meet Today’s Guest Lindsay has spent nearly 40 years teaching first grade while also building a successful side career in real estate. After earning her real estate license in 2004 during a teaching job-share arrangement, she spent over 20 years helping clients buy and sell homes while continuing her work in the classroom. Key Takeaways Teachers Can Successfully Build Side Hustles Lindsay’s story proves that educators can pursue additional income streams without giving up teaching. Real Estate Can Supplement Retirement One major theme of the episode is using real estate income to help offset the realities of teacher retirement benefits. Trust Is a Superpower Teachers naturally build trust with people, which can become a huge advantage when working with real estate clients. Systems and Support Matter Lindsay discusses the importance of: * Good brokers * Transaction coordinators * Reliable people on your team Trying to do everything alone makes balancing both careers much harder. You Can Handle More Than You Think One of the most inspiring moments of the episode centers around discovering personal capacity and learning how to manage multiple responsibilities successfully. Topics Discussed Becoming a Realtor While Teaching * Getting licensed * Passing the exam * Starting with mentorship and support * Building business gradually Balancing Two Careers * Working during summers and breaks * Managing paperwork around school schedules * Setting expectations with clients Financial Benefits * Supplemental income * Paying for weddings and college expenses * Supporting retirement planning * Using commissions strategically Lessons Learned * The importance of ethics and trust in real estate * Choosing the right people to work with * Managing burnout and exhaustion Memorable Quotes “Teacher by day, realtor by night.” “You can do more than you think you can.” “I’ve always told people upfront, I’m a teacher first.” “There’s always enough hours in the day to switch gears.” “It’s great as a supplemental income.” 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. 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 agent Because you don’t have to leave the classroom to start building wealth outside of it.