n this episode Matt sits down with a longtime client and friend who’s exploring real estate as a second career after years in senior living sales. Together, they dive into the challenges and opportunities of starting fresh at 60, how relationship-building skills translate across industries, and why real estate is less about houses and more about people.

If you are looking for inspiration to take that first step, this candid conversation offers practical insights, honest truths, and a reminder that it’s never too late to reinvent yourself.

Building a Second Career Path at 60 | All Roads LTR Podcast | Ep. 56

In this episode Matt Rhine sits down with teammate and rising star Craig Kirkner to share an incredible story of grit, sacrifice, and success.

Craig went from running seafood markets as a teenager to nearly giving up on real estate after piling up debt and setbacks. But with a “no backup plan” mindset, he came back stronger—building a thriving career that hit $24 million in production in just 12 months.

Together, Matt and Craig dive into:

 * The tough realities of starting out in real estate (and why most agents quit early)
 * How work ethic, mentorship, and team structure fueled Craig’s growth
 * The sacrifices that made success possible (including selling his beloved truck)
 * Why real estate isn’t just a job—it’s a lifestyle
 * The future of the industry, and why relationships will always matter more than AI

An Agent’s Journey: From Seafood Markets to $24M in Sales | All Roads LTR Podcast | Ep. 55

In this episode Matt sits down with Disney travel expert Danielle Treadwell of Platinum Mouse—a planner who visits the parks up to seven times a year and knows every secret, shortcut, and splurge-worthy extra.

From mastering Lightning Lanes and avoiding crowds to uncovering hidden gems and allergy-friendly dining, Danielle explains how to turn a potentially overwhelming trip into a stress-free, magical experience. Whether you’re a first-time visitor, a Disney adult, or planning with kids in tow, this conversation will change the way you approach your next trip to the “Happiest Place on Earth.”

The Disney Insider’s Guide: How to Skip Lines, Save Money & Make Every Moment Magical | All Roads LTR Podcast | Ep.54

Today Matt sits down with Jacob Benzaquen—a Jewish immigrant from Venezuela, Baltimore-based property management entrepreneur, and a man with a global story. Jacob shares his remarkable journey from Venezuela to Miami, Israel, and ultimately Baltimore, offering a unique perspective on real estate, immigration, and the importance of building communities. In an increasingly divided world, Jacob's story is a true testament to resilience, opportunity, and the power of human connection.

An Immigrant Revitalizing Neighborhoods in Baltimore | All Roads LTR Podcast | Ep. 53 

In this episode Matt sits down with renowned Baltimore architect, Peter Radcliffe. We delve into Peter's illustrious career, the legacy of architectural excellence passed down from his father, and the intricate process of designing both luxurious and practical living spaces. Discover the most significant trends in modern architecture, the challenges faced when renovating historical homes, and the invaluable insights from a career spanning over nearly 25 years.

Architectural Masters - Peter Ratcliffe

Today Matt sits down with the unstoppable Colleen Rippey, a powerhouse in sales, networking, and industry leadership. From her early days as a top-performing Cutco saleswoman (she sold over $2 million in knives!) to running Baltimore’s Real Producers magazine—the premier networking hub for top real estate professionals—Colleen has mastered the art of connection and influence.

Matt and Colleen dive into her journey, the power of building relationships, and how she went from rapping at lunch-and-learns to ranking #1 out of 130 franchises. If you want insights on what makes a true super connector, how top realtors think, and why relationships are everything in this business, this episode is a must-listen.

The Super Connector: From Selling Knives to Connecting the Real Estate Elites | All Roads LTR Podcast | Ep. 52

In this episode, we are joined by Jake Bowling, an experienced home inspector of Blue Crab Inspections. Learn about the importance of thorough inspections, how to manage expectations, and the key areas to focus on, such as roofs, basements, HVAC systems, and more. We discuss the role of inspectors and contractors, the challenges of dealing with insurance and warranties, and the value of honesty and integrity in the real estate market. This episode provides essential tips and advice to ensure peace of mind and successful real estate transactions.

Beyond the Surface: Understanding What is a Quality Home Inspection | All Roads LTR Podcast | Ep. 51

In this episode, we talk about the key differences between today's housing market and the infamous 2008 crash. From stricter lending standards to soaring equity and appreciation, our special guest Ayaz Rahemanji from First Home Mortgage breaks down why a market collapse is unlikely this time around. We also explore smart strategies for navigating high mortgage rates, refinancing tips, and why buying now might be a better decision than waiting.

From the Wild West to Stability: Why 2024 is Different from 2008

In this episode, Matt Rhine sits down with Nicole Hewitt, a seasoned attorney specializing in estate planning, elder law, and business planning. With years of experience, Nicole breaks down the essentials of estate planning—what it really means, why it’s important for everyone (not just the wealthy), and how proper planning can prevent future family conflicts. From wills and trusts to the nuances of managing real estate within an estate, Nicole explains how to effectively plan for the unexpected.

Estate Planning: How to Protect Your Assets and Your Family’s Future 

In today's episode, I’m finally recording some of the real estate investment strategies I’ve shared countless times. I’ll dive into my personal approach, shaped by years of hands-on experience—both successes and hard-learned lessons. From setting investment criteria to understanding cash flow, appreciation, and debt reduction, I’ll outline a method that’s safe, conservative, and designed to minimize risk while maximizing returns. Whether you're new to real estate or looking to refine your strategy, you’ll find insights to help you build wealth while avoiding common pitfalls.

All Roads Lead To Real Estate