Agent2Investor Podcast

Today we unpack the highs and lows of real estate investing. From wild tenant stories to hard-earned lessons in property management and deal-making, we share practical insights every investor can use. You'll also hear how networking, visualization, and constant learning shaped their journey. Whether you're scaling up or just getting started, this episode delivers real, relatable insights.Chapters:00:00 Intro01:43 Ana's RE Journey03:09 Property Management14:15 Setting Boundaries and Expectations18:08 Nico's Exciting New Deal27:40 Private Money Lender 28:52 Foreclosure Challenges30:01 Problem Solving30:43 Building Credibility with Private Money Lenders31:22 Driving for Dollars Strategy31:46 Southern Virginia Project Updates32:31 Challenges of Out-of-State Investing35:01 Financing with Local Banks38:37 Self-Managing Rental Properties41:41 Midterm Rental Success and Challenges48:34 Mastermind Experience in Greece

In this episode of the Agent to Investor Podcast, we sit down with Ricky Ricardo — a full-time construction worker, proud father, and first-gen real estate investor — to hear how he bought not one, not two, but three properties in less than a year… all while working 60+ hours a week and living thousands of miles away from his investments.Ricky shares how he overcame analysis paralysis, bought his first rental sight-unseen, took a risk on a $100K house, and eventually landed his first flip — a deal that nearly turned into a BRRRR by necessity. If you're still sitting on the sidelines, wondering if you’re “ready enough,” this episode is your green light.

Thinking about going from selling homes to owning them? In this episode of the Agent to Investor Podcast, we sit down with Leo, a real estate agent turned investor, to talk about the mindset, strategy, and practical steps agents need to take to build long-term wealth through real estate investing.Whether you're a full-time realtor, part-time investor, or just curious about getting started, Leo shares how to make the shift from agent to investor — without getting overwhelmed.Topics we cover:How to start investing as a real estate agentWhy agents are uniquely positioned to grow wealthBuilding a personal brand that attracts dealsMistakes to avoid when buying your first rentalWhy networking and visibility on social media matters

Jaren — better known online as Finance Cowboy — didn’t grow up around money, investing, or real estate. In fact, after college he was buried in over $110,000 of debt, working a W2 sales job, and wondering how to get ahead.In this episode, he shares how he and his wife tackled that debt aggressively, then turned their financial margin into massive momentum. Within a single year, Jaren scaled from 2 rental properties to 22 doors using creative financing, the BRRRR strategy, and the power of his stable W2 income.We dive deep into:✅ How he used private money and HELOCs to scale✅ Why W2 employees have a HUGE lending advantage✅ The exact playbook he used to go from zero to financial freedom✅ What most “investor-friendly agents” still get wrong✅ The truth about building wealth without quitting your jobWhether you’re just getting started or stuck trying to scale, Jaren brings real talk and a repeatable roadmap for building wealth the Finance Cowboy way.00:00 Intro01:36 Personal Story04:17 Learning from Others07:17 The Role of Debt09:14 Balancing a Job and Real Estate Investing12:32 Finding and Managing Your First Deal15:53 The Importance of Investor-Friendly Agents19:24 Managing Contractors and Projects25:30 Collaborative Real Estate Ventures26:00 Challenges in Finding Reliable Team Members27:19 The Importance of Analyzing Deals29:06 Scaling with the BRRRR Method32:00 Creative Financing Strategies34:33 Finding and Securing Deals41:40 Building an Online Presence46:10 Lessons and Advice for New Investors

In this episode of the Agent to Investor Podcast, we sit down with Donato Callahan, the 25-year-old founder of BrightInvestor and owner of over 500 rental units. Donato walks us through his whirlwind journey from a Department of Defense analyst to a full-time entrepreneur and real estate investor in just two years.He shares:✅ How a stock market loss pushed him into real estate✅ His path from house hacking to commercial deals✅ The origin story of BrightInvestor—and how it replaces 30+ research tools✅ How he built a 500-unit portfolio by focusing on speed, data, and gut instinct✅ A brutal wake-up call from a 17-year DOD veteran that fueled his driveIf you’re looking for inspiration, strategy, and an edge in your investing journey, don’t miss this one.00:00 Introduction01:24 Donato's Real Estate Journey02:09 Educational Background and Keynote Speaking05:19 Balancing Day Job and Real Estate08:34 Leaving the Government Job13:47 The 'Why Not?' Mindset15:33 Building Bright Investor18:31 Solving Real Estate Problems with Technology19:54 Data Sources for Bright Investor20:54 Beyond Public Data: Licensing Agreements22:08 Innovative Features and Integrations23:31 Expanding Bright Investor's Reach25:36 Advice for New Real Estate Investors27:33 Coaching and Personal Involvement31:09 Future Plans for Bright Investor37:57 Personal Interests and Lifestyle

In this discussion, Craig Curelop, author and former finance analyst, reveals his journey to financial freedom through house hacking. He shares how he started by renting bedrooms, achieving $3,000/month in passive income. Craig emphasizes that your first investment doesn't need to be perfect; it's about getting started. He also highlights the potential of co-living as a wealth-building strategy and discusses the importance of finding the right partners in life and investing. Discover how risk-taking and creative sacrifices led him to success.

One simple mistake could leave your rental property completely uninsured. In this episode, Steadily CEO Darren Nix breaks down the key differences between homeowner and landlord insurance—and the risks investors overlook that can cost them big. Whether you own one property or a whole portfolio, this is a must-watch.00:00 Introduction 03:04 Founding and Growth 05:55 Understanding Insurance Policies15:01 Insurance for Different Property Scenarios24:59 High Deductible Insurance Strategy26:06 Understanding Deductibles28:08 The CLUE Report and Its Impact29:06 Insurance for Landlords and Investors31:00 House Hacking Insurance Tips31:58 Replacement Cost vs. Actual Cash Value36:43 Common Insurance Mistakes38:20 Additional Coverage Options40:44 Pet Insurance Considerations for Landlords44:20 Feel-Good Insurance StoriesFollow Darren- https://www.linkedin.com/in/darrensnix/

In this episode of the Agent to Investor podcast, I sit down with Matt Camp from DealMachine—a guy who not only lives and breathes real estate, but also helped build one of the most powerful tools in the industry. We get into everything from how DealMachine makes finding off-market deals as easy as clicking a button, to how Matt started investing in his hometown of St. Louis with a couple of close friends and a clear game plan.We also dive into:How a book in middle school started Matt’s wealth-building mindsetWhy “data is only as valuable as what you do with it”How to skip trace smarter (and for free)The game-changing power of automation in your marketingThe best and worst advice Matt’s gotten in real estateIf you’re an agent, investor, or just someone real estate-curious—this episode is packed with value. Let’s dive in.00:00 Introduction 04:01 Early Mentors06:16 Using Deal Machine for Local Investments08:26 The Origins and Evolution of Deal Machine13:34 Marketing Strategies with Deal Machine19:32 Navigating Do Not Call Regulations20:25 Leveraging AI in Cold Calling22:24 Efficient Mail Sequences for Real Estate23:26 Customizing and Tracking Mail Campaigns27:06 Integrating Auto Dialers with Mail Campaigns31:23 Building Relationships and Taking Action33:51 Support and Resources for Deal Machine UsersConnect with Matt- https://www.linkedin.com/in/mattkamp/

Kelli shares her journey into real estate investing, from early DIY home projects to becoming a successful investor. We discuss her first property purchases, navigating challenges with contractors, and the essential role of having an investor-friendly agent. Kelli  also emphasizes the importance of networking, learning from others, and being fearless in the world of real estate. Tune in for practical tips, inspiring stories, and insights into making real estate investing work for you.00:00 intro02:33 First Steps in DIY07:19 Challenges and Realizations in Home Renovation11:34 Real Estate Market and Finding Deals24:46 Investor-Friendly Agent32:00  Potential of a New House35:03 Challenges in Selling the Property36:06 Pivoting to Renting the Property38:11 Finding the Perfect Tenants46:07 The Importance of Networking in Real Estate49:31 Balancing Life and Real Estate Investing55:58 Recommended Books for Real Estate Enthusiasts

Today we have Sean McKay, a seasoned real estate investor, discussing his journey into real estate, the lessons learned from early investments, and the importance of mentorship and community in the investing space. We explore various investment strategies, the significance of understanding loan products, and the different phases of a real estate investor's journey, culminating in a discussion about self-directed IRAs as a powerful investment tool. In this conversation, Sean McKay discusses the intricacies of self-directed IRAs, the pros and cons of investing through them, and the importance of understanding the rules and regulations involved. He emphasizes the value of private money lending in real estate and shares insights on portfolio management, diversification, and the lessons learned throughout his investment journey. The discussion also touches on the importance of education and community in making informed investment decisions.00:00 Introduction 03:15 Real Estate Challenges 13:24 The Importance of Community and Mentorship18:38 Phases of a Real Estate Investor's Journey21:59 Introduction to Self-Directed IRAs24:01 Pros and Cons of Self-Directed IRAs25:49 Regulatory Challenges in the Self-Directed Space28:05 Personal Experiences with Self-Directed IRAs33:13 Private Money Lending with Self-Directed IRAs38:04 Smaller Portfolio42:05 Advice for Aspiring InvestorsConnect with - Sean- https://www.instagram.com/charlotteadubuilders/Nico- https://www.instagram.com/ngarciaofficial/Ana- https://www.instagram.com/anabialek_realtor/