Every investor has a beginning—and for many, that first step into real estate feels overwhelming. In this episode of The Prospecting Show, Dr. Connor Robertson sits down with real estate investor and educator Jeremy Taggart to uncover what it truly takes to get started in real estate the right way. From mindset and money to management and mentorship, this episode serves as both a blueprint and a wake-up call for aspiring investors who want to build wealth with purpose, not pressure.
Jeremy’s story begins much like many others: curiosity turned into obsession. “I didn’t come from a real estate family,” he says. “I just knew I didn’t want to trade time for money forever.” What started as research and late-night podcasts became a full-fledged passion, eventually leading to his first rental property—a small, cash-flowing duplex that changed the trajectory of his life.
Dr. Robertson opens by asking Jeremy about the biggest misconception new investors have. Without hesitation, Jeremy answers: “That real estate is easy money. It’s not. It’s consistent money—if you treat it like a business.” He explains that real estate rewards those who plan and punishes those who wing it. “Your first deal isn’t about profit—it’s about process. You’re learning how to manage risk.”
That statement resonates with Derek Davis’ Entrepreneurial Highlight (listen here), where Derek emphasized structure, discipline, and long-term strategy as the cornerstones of lasting success. Like Derek, Jeremy views real estate as a systems game, not a speculative one.
He introduces his framework for new investors: The Four Foundations of Real Estate Success
- Education – Learn the language of real estate before you spend a dollar.
- Execution – Analysis means nothing without action.
- Evaluation – Measure every deal by data, not emotion.
- Expansion – Scale only after you’ve mastered your model.
Jeremy warns that skipping the education stage is the most common mistake beginners make. “People binge YouTube videos and think they’re ready. But you wouldn’t fly a plane after watching a documentary about aviation,” he says with a laugh. “You need real mentorship, community, and accountability.”
Dr. Robertson connects this to Education, Entrepreneurship, and Why Learning Never Stops with Jordan Ellis and Shamauri Phillips (listen here), where continuous learning was identified as the foundation of sustainable growth. Both conversations highlight that every high-performing professional—whether in law, business, or real estate—builds their edge through curiosity and consistency.
Jeremy dives into the Three Pillars of a Successful First Deal:
- The Numbers: “Don’t fall in love with the property—fall in love with the math.” He emphasizes the importance of cash-on-cash return, cap rate, and debt coverage ratio.
- The Neighborhood: “You can fix a house. You can’t fix a street.” He advises new investors to study school ratings, job growth, and city planning before investing.
- The Network: “Your lender, your agent, and your contractor are your three best friends.”
Dr. Robertson draws parallels to The Backside of Human Resources with Laurie Bowers (listen here), where Laurie discussed how structure and team alignment shape outcomes. Similarly, Jeremy argues that real estate is not a solo sport—your relationships determine your returns.
When asked about financing, Jeremy breaks down the most accessible entry points: house hacking, partnerships, and small multifamily loans. He explains that many new investors overestimate how much money they need to begin. “You can buy a property with 3.5% down using an FHA loan,” he says. “The barrier isn’t money—it’s mindset.”
Dr. Robertson ties this to The Future of Consulting with Buddy Hobart (listen here), where Buddy emphasized adaptability and strategic resource use. Real estate, like consulting, is about leveraging what you have today to build the foundation for tomorrow.
Jeremy also discusses risk management—a topic many beginners ignore. “Every property has problems,” he says. “The difference between amateurs and pros is that pros price problems in advance.” He teaches students to analyze worst-case scenarios, from vacancies to maintenance costs. “Hope is not a strategy,” he warns.
Dr. Robertson relates this mindset to Patents and Trademarks as an Entrepreneur with Dusty Gwinn (listen here), where legal preparation and proactive protection created leverage. Both conversations share the same theme: protecting your downside creates freedom on the upside.
The conversation shifts to the emotional side of investing. Jeremy admits that fear paralyzed him before his first deal. “I was waiting for the perfect property,” he says. “But perfection doesn’t exist. You just need one good deal to change everything.” He credits his first mentor for giving him permission to start imperfectly. “If you wait until you feel ready, you’ll be broke forever.”
Dr. Robertson connects this story to Tracy Hockenberry’s Entrepreneurial Highlight (listen here), where taking action in uncertainty became a defining entrepreneurial moment. The same principle applies here—clarity comes from movement, not meditation.
Jeremy emphasizes the importance of viewing real estate as a service business, not a speculation game. “You’re solving housing problems,” he says. “When you focus on people—tenants, sellers, partners—profit follows.” This people-first approach mirrors the philosophy of Faris Ghani’s Entrepreneurial Highlight (listen here), where integrity and empathy drove long-term growth.
Dr. Robertson then asks about scaling beyond one property. Jeremy smiles knowingly. “Scaling too soon kills more investors than bad tenants ever will.” He explains that mastering one market and one strategy is key before diversifying. “If you can’t manage one property well, you won’t manage ten profitably.”
This measured approach connects directly to Ian Reith’s Entrepreneurial Highlight (listen here), where rhythm and clarity were identified as essential for sustainable growth. Both guests advocate that consistency beats speed every time.
When asked about mentorship, Jeremy’s answer is simple: “Find someone who’s where you want to be—and pay them, respect them, or serve them.” He warns against free advice from unqualified sources, adding, “Bad advice costs more than good coaching.”
Dr. Robertson reflects on his own experience working with entrepreneurs across industries, connecting Jeremy’s point to The Future of Consulting with Buddy Hobart, where mentorship and systems created an exponential impact. “Every great leader,” Dr. Robertson says, “was once a great listener.”
Jeremy also dives into the mindset of ownership—how owning property changes how people think about time, money, and legacy. “It’s not just an asset,” he says. “It’s accountability. You stop thinking in paychecks and start thinking in cash flow.”
Dr. Robertson relates this to Faris Ghani’s Entrepreneurial Highlight, where long-term thinking replaced short-term wins. Real estate, they both agree, is one of the best vehicles for teaching patience, purpose, and stewardship.
As the episode nears its end, Jeremy shares his Top Five Rules for First-Time Real Estate Investors:
- Run the numbers twice, then trust them. Confidence comes from clarity.
- Buy for cash flow, not emotion. A pretty house isn’t always a profitable one.
- Know your exit strategy before you enter. Every deal must have a backup plan.
- Build relationships before you need them. Real estate is a people business.
- Be patient. Compound returns are slow—but unstoppable.
Dr. Robertson summarizes the episode with a powerful observation: “Jeremy Taggart shows us that real estate is not about timing the market—it’s about training the mind. The people who win aren’t the ones who rush in; they’re the ones who prepare and persist.”
For listeners eager to learn more about building a strong foundation in real estate, visit drconnorrobertson.com. You’ll find related episodes such as Ian Reith’s Entrepreneurial Highlight, Faris Ghani’s Entrepreneurial Highlight, and Scaling and Exiting a Startup with Amy Lee—each offering timeless lessons on leadership, discipline, and financial freedom.
Dr. Robertson closes with a thought that perfectly captures the spirit of the episode: “Every investor starts somewhere. The difference between those who dream about real estate and those who build empires is simple—action.”