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

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

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.

Episode 12: Real Estate Isn’t Passive… But It IS Worth It

In this episode of Chalkboards to Cash Flow, we’re breaking down one of the biggest myths in real estate investing: passive income. If you’ve ever been told real estate is an easy path to overnight wealth, this episode is your reality check. From managing tenants and repairs to building long-term equity and freedom, this conversation dives into what investing actually looks like behind the scenes, especially for teachers balancing full-time careers. The truth? Real estate isn’t passive, and it’s definitely not a get-rich-quick scheme. But for those willing to play the long game, it can become one of the most powerful wealth-building tools available. In This Episode, We Cover: * Why “passive income” in real estate is often misunderstood * The work that goes into investing while working full time * Why real estate is a long-term wealth strategy * Building cash flow slowly and sustainably * Equity, appreciation, and tax benefits explained simply * Why teachers are uniquely positioned to succeed in real estate * The emotional ups and downs of investing * Staying committed to the long game Key Takeaways Real Estate Is Not Passive Successful investing requires active effort: * Researching deals * Running numbers * Managing tenants or guests * Handling repairs and turnovers * Tracking finances and taxes Wealth Is Built Slowly Real estate rewards consistency over speed. You build: * Cash flow over time * Equity as tenants pay down mortgages * Appreciation through long-term ownership * Financial freedom through patience Teachers Already Have the Right Mindset Educators naturally think long term through: * Lesson planning * Goal setting * Structure and consistency That same mindset can translate powerfully into investing success. Freedom Over Flash This episode focuses on sustainable freedom, not flashy lifestyles or overnight success stories. Memorable Quotes “Real estate is not passive.” “This isn’t crypto or scratcher tickets.” “You build cash flow $200 at a time.” “Real wealth in real estate often comes from holding, not flipping.” “It’s not passive. It’s not fast. But it is powerful.” Connect With The Show Follow and connect with Chalkboards to Cash Flow for more conversations around real estate, financial freedom, and investing for educators. Join the free Facebook community for teachers and everyday investors building wealth one step at a time. Enjoyed This Episode? If this episode helped you rethink real estate investing: * Follow the podcast * Leave a review * Share this episode with a friend or fellow educator * Send a DM to the show on Instagram Because you don’t need to be rich to start. You just need to start.

Episode 11: Think You Missed the Boat Investing Later in Life? Think Again.

In this episode of Chalkboards to Cash Flow, we’re talking directly to educators and everyday professionals who feel like they started investing too late. If you’re in your 40s, 50s, or even 60s and wondering whether real estate investing is still possible for you, this episode is the encouragement and practical guidance you need. From leveraging home equity and retirement accounts to partnering with family members, this conversation breaks down realistic ways to begin building wealth later in life. The message is simple: you did not miss your chance. In This Episode, We Cover: * Why it’s never too late to start investing * The financial realities many teachers face approaching retirement * Starting over financially after major life changes * Advantages older investors actually have * How educators can use stability and experience to their advantage * Practical ways to start investing later in life * Using HELOCs, retirement accounts, and partnerships * Why taking the first step matters more than timing Key Takeaways You Haven’t Missed the Boat Many people believe investing is only for younger generations, but starting later in life still creates opportunities for long-term wealth and financial freedom. Educators Have More Advantages Than They Realize Older investors often bring: * Better credit * More financial discipline * Home equity * Retirement account options * Career stability and life experience Small Steps Create Big Change The first property may not change your life overnight, but over time, consistent action can completely reshape your financial future. Practical Strategies Mentioned Tap Into Home Equity Use existing equity through: * HELOCs * Cash-out refinancing Leverage Retirement Accounts Explore: * Self-directed IRAs * 403(b) rollover opportunities Partner With Others Collaborate with: * Adult children * Friends * Other educators This can help combine: * Credit * Capital * Experience * Energy Memorable Quotes “It’s never too late to start.” “You didn’t miss the boat.” “That first property changed everything. Not overnight, but over time.” “You’re not behind. You’re just getting started.” “You don’t need to be rich to start. You just need to start.” Connect With The Show Follow Chalkboards to Cash Flow for more conversations around real estate investing, financial freedom, and building wealth as an educator. Join the free Facebook community and connect with other teachers and everyday investors taking action toward financial independence. Enjoyed This Episode? If this episode gave you hope or a fresh perspective: * Follow the podcast * Leave a review * Share it with another educator * DM the show on Instagram * Join the Chalkboards to Cash Flow Facebook group Because no matter your age or starting point, the best time to begin is now.