Creative Financing and Loan Assumptions with Jefferson Calloway
Scaling a real estate portfolio is challenging enough—but doing it across multiple states while serving in the military takes a whole different level of strategy. Jefferson Calloway started investing in 2019 while stationed as a helicopter pilot in the U.S. Army, buying a townhome near Fort Rucker, Alabama. Since then, he’s mastered creative financing and grown his portfolio to 27 doors across seven states with over $1 million in equity. Jefferson is here to share how new investors can find and finance deals creatively, scale in high-interest markets, and why investing near military bases might be one of the best-kept secrets in real estate. Find out more: Jefferson@calcapital.us Website - www.americanhomeconcepts.com Instagram - https://www.instagram.com/jeffersoncalloway/ LinkedIn - https://www.linkedin.com/in/jefferson-calloway-2bb17381/ Today’s episode is brought to you by Green Property Management, managing everything from single family homes to apartment complexes in the West Michigan area. https://www.livegreenlocal.com And RCB & Associates, helping Michigan-based real estate investors and small business owners navigate the complex world of health insurance and Medicare benefits. https://www.rcbassociatesllc.com
28 Jul 31min
From FedEx to a 7-Figure Painting Business: Ramond Harris on Pivots, Paint, and Profits
Justin Workman and I sit down with Detroit investor and entrepreneur Ramond Harris at the Midwest Real Estate Investor Conference for our fifth annual update. Ramond shares his journey from running FedEx delivery routes to acquiring and scaling a commercial painting business, VR Quality Painting, specializing in apartment renovations and interior construction. Key topics include: How networking at the conference led to pivotal business connections, including meeting his current lawyer and business partners. Lessons learned from exiting the FedEx delivery business, including managing truck assets and navigating contract negotiations. The transition to commercial painting and construction, with a focus on apartment complexes and building relationships with general contractors and property managers. The importance of sales, estimating, and team structure in growing a service business. Strategies for leveraging minority business certifications (DBE/MBE) to win government and university contracts. Real-world advice on bidding, pricing, and the challenges of scaling a trades-based company. If you’re interested in commercial painting, apartment renovations, or learning how to pivot and grow in the real estate and construction industries, this episode is packed with actionable insights and candid stories. Contact Ramond Harris: VR Quality Painting (soon to be VR Construction & Painting) Email: ramond.harris@yahoo.com Phone: (734) 891-7954 Today’s episode is brought to you by Green Property Management, managing everything from single family homes to apartment complexes in the West Michigan area. https://www.livegreenlocal.com And RCB & Associates, helping Michigan-based real estate investors and small business owners navigate the complex world of health insurance and Medicare benefits. https://www.rcbassociatesllc.com
21 Jul 42min
Deal Structuring, Waterfalls and Investor Psychology with Rob Beardsley
There’s a lot of noise in the commercial real estate space—but today’s guest brings the kind of clarity that only comes from experience and execution. Rob Beardsley is the Founder of Lone Star Capital, and in just a few years, he’s built a portfolio of over $750 million in multifamily real estate. He’s the author of two best-selling books on commercial real estate, a national speaker, and the host of The Lone Star Capital Podcast. Rob is known for breaking down complex topics like underwriting, equity and debt structuring, and institutional operations, making them accessible to investors at every level. He’s here to share the strategies that have helped him scale, raise capital, and operate at a high level in today’s shifting real estate landscape. Find out more: www.lscre.com Today’s episode is brought to you by Green Property Management, managing everything from single family homes to apartment complexes in the West Michigan area. https://www.livegreenlocal.com And RCB & Associates, helping Michigan-based real estate investors and small business owners navigate the complex world of health insurance and Medicare benefits. https://www.rcbassociatesllc.com
14 Jul 35min
Profitable Short-Term Rental Arbitrage and Algorithm Strategies with Quentin West
The short-term rental market has created incredible opportunities for investors—but success isn’t just about listing a property on Airbnb. It takes strategy, optimization, and resilience to build a thriving business. Quentin West knows this firsthand. After facing financial hardship, he turned to Airbnb and built a short-term rental empire generating over $100,000 per month. Now, as a leading Airbnb coach and investor, he’s helped over 1,000 students across 15 countries achieve financial independence through Airbnb arbitrage, scaling strategies, and cracking the Airbnb algorithm. Quentin is here to share how investors can build, optimize, and scale a profitable STR portfolio—even in tough markets. Find out more: shortcuttosuperhost.com Instagram: @qdealshomes Today’s episode is brought to you by Green Property Management, managing everything from single family homes to apartment complexes in the West Michigan area. https://www.livegreenlocal.com And RCB & Associates, helping Michigan-based real estate investors and small business owners navigate the complex world of health insurance and Medicare benefits. https://www.rcbassociatesllc.com
7 Jul 30min
From $50K/Month to 50/50 Flip: How Dedric & Krystal Polite Turned Real Estate into a TV Hit
They started with almost nothing—and turned it into everything. Dedric and Krystal Polite are the stars of A&E’s 50/50 Flip (now on Hulu), a real estate power couple who built a $50K/month wholesaling business and used it to create a multimillion-dollar rental portfolio. In this episode, they share how they went from scraping by to financial independence, what it’s really like to build a business as a couple, and how they turned their real estate journey into a hit TV show. If you’ve ever wondered what it takes to go from broke to building generational wealth—this episode lays it out. Find out more: politewealthportal.com politewealthportal.com/accountabilitychartdownload politewealthportal.com/live Today’s episode is brought to you by Green Property Management, managing everything from single family homes to apartment complexes in the West Michigan area. https://www.livegreenlocal.com And RCB & Associates, helping Michigan-based real estate investors and small business owners navigate the complex world of health insurance and Medicare benefits. https://www.rcbassociatesllc.com
30 Jun 32min
Revolutionizing Luxury Real Estate and Short-Term Rentals with Stephen Petasky
Luxury real estate is evolving, and my guest today, Stephen Petasky, is leading the charge. As Founder and CEO of The Luxus Group, he’s redefining high-end vacation homeownership through innovative co-ownership models, managing $100M+ in luxury properties across six countries. From restoring historic estates in Italy to leading $1B+ developments like the Four Seasons Las Vegas, Stephen is making luxury real estate more accessible while maintaining top-tier quality. Recognized as one of Canada’s Top 40 Under 40, he’s here to share the four pillars of luxury that help create high-end experiences at scale. Find out more: https://www.luxusvp.com https://enalake.com/ IG & LinkedIn: Stephen Petaskey Today’s episode is brought to you by Green Property Management, managing everything from single family homes to apartment complexes in the West Michigan area. https://www.livegreenlocal.com And RCB & Associates, helping Michigan-based real estate investors and small business owners navigate the complex world of health insurance and Medicare benefits. https://www.rcbassociatesllc.com
23 Jun 34min
How Sayam Ibrahim Walked Away from His Job and Closed Over $250M in Real Estate Deals
Real estate investing offers one of the most powerful paths to building long-term wealth—but for many, getting started feels overwhelming. Sayam Ibrahim knows that struggle firsthand. After quitting his job the week of his wedding, he went all in on real estate and never looked back. Today, he’s closed over 1,400 transactions totaling more than $250 million in deals. In this episode, Sayam shares how he built his real estate empire from the ground up—without significant capital—and why finding the right mentor changed everything. With roots in both Dominican and Ethiopian communities, he brings a unique perspective to investing in diverse markets and making real estate accessible to anyone. We dive into his step-by-step approach to scaling a portfolio, strategies for getting started even with limited resources, and the mindset needed to succeed in any market. If you're ready to take action and build real wealth through real estate, this episode is for you. Find out more: YouTube Apple Podcast Spotify Instagram Website Today’s episode is brought to you by Green Property Management, managing everything from single family homes to apartment complexes in the West Michigan area. https://www.livegreenlocal.com And RCB & Associates, helping Michigan-based real estate investors and small business owners navigate the complex world of health insurance and Medicare benefits. https://www.rcbassociatesllc.com
16 Jun 31min
The Power of Disruption and Embracing Failure with Jeremy Delk — Episode 492
Success in business and real estate isn’t about playing it safe—it’s about disrupting industries, embracing failure, and taking bold action. Jeremy Delk knows this better than anyone. From day trading as a teenager to building Delk Enterprises, a diversified investment firm with holdings in real estate, biotech, technology, and consumer brands, he’s made a career out of spotting opportunities, pivoting fast, and challenging the status quo. Jeremy is here today to share why disruption is key to thriving in real estate and business, and how failure—when embraced the right way—can be the ultimate competitive advantage. Find out more: Search @Jeremysdelk on all social media platforms. https://jeremydelk.com/ Today’s episode is brought to you by Green Property Management, managing everything from single family homes to apartment complexes in the West Michigan area. https://www.livegreenlocal.com And RCB & Associates, helping Michigan-based real estate investors and small business owners navigate the complex world of health insurance and Medicare benefits. https://www.rcbassociatesllc.com
9 Jun 36min
