Episode Overview In this episode, Michael talks with San Diego-based real estate investor Justin Brennan about one of the hottest topics in housing today, the rise of the 50-year mortgage, and what it means for homebuyers, investors, and the future of urban development. Their discussion explores the practical realities behind long-term mortgages, market resilience, and the shift toward apartment investments as a sustainable wealth strategy.

Michael and Justin open with a breakdown of the new 50-year mortgage trend. While these loans may sound like a solution for affordability, Justin explains that they’re mainly amortization tools designed to reduce monthly payments, not a pathway to home ownership. Since the average homeowner stays in their property for 5.5 to 7 years, very few people will ever pay off a home under such a long-term structure.

The takeaway: it’s more about short-term cash flow than long-term payoff.

Justin shares how his upbringing in San Diego shaped his perspective. Coming from a family deeply rooted in both real estate and military service, he learned valuable lessons about risk, leverage, and resilience from his grandmother and father. His father’s experience during the 2008 financial crisis inspired Justin to take a more measured, apartment-focused investment approach that prioritizes stability and steady income.

Michael draws parallels between the cyclical nature of the auto and housing sectors, noting that true wealth often comes from those who rebuild after financial loss. Together, they examine current trends: single-family housing shortages in coastal markets, the growth of vertical construction in San Diego, and temporary oversupply in Sunbelt regions. Both agree that while red tape slows coastal development, new models for multifamily housing are creating fresh opportunities for investors.

Michael predicts a generational shift on the horizon as baby boomers eventually leave the housing market. With many holding onto single-family homes longer than ever, a massive turnover is expected in coming decades. This could lead to the redevelopment of neighborhoods into multifamily housing, reshaping the fabric of communities nationwide. Justin agrees, noting that this transition will open doors for new investors and developers focused on density and urban design.

Justin goes deep into apartment investing, emphasizing its scalability and operational efficiency. He contrasts apartment ownership with single-family rentals, pointing out reduced maintenance costs, shared insurance, and easier management structures. His key message: mastering deal analysis and financing structures is essential to unlocking the best real estate opportunities.

For those with limited capital, Justin explains how apartment syndication can serve as an entry point. With as little as $30,000, investors can join syndicates that purchase 10 to 30-unit buildings in affordable markets like the Midwest. He compares syndicators to high-level problem solvers, likening their expertise to neurosurgeons or hedge fund managers. The value lies in their ability to identify, structure, and manage complex deals that generate long-term wealth and legacy potential.

Michael and Justin discuss how artificial intelligence is reshaping real estate strategy. From analyzing property data to modernizing apartment amenities like Wi-Fi, digital shopping hubs, and smart community features, AI is becoming a tool for creating scalable and livable investments. They stress that success comes from curiosity, understanding market language, and embracing innovation.

Justin closes by sharing his entrepreneurial journey—marked by persistence, calculated risk, and the ability to take action even when under pressure. He encourages listeners to use downtime productively, whether that means starting a side hustle or investing in real estate education.

His final message: the ability to endure stress and uncertainty is what separates dreamers from successful entrepreneurs.

Find out more:

https://www.brennanpohle.com/

YouTube: https://www.youtube.com/@JustinBrennan

Learn more insights from Michael Levitt and thought leaders shaping the future of leadership, resilience, and success at BreakfastLeadership.com/blog.

Exiting Tech Businesses: Insights from Draven Draven, a seasoned tech entrepreneur, joined Michael to discuss his journey of building and successfully exiting two tech companies. The first was a software development agency that he scaled organically, and the second was a field service management business sold to a billion-dollar private equity group in July 2024. Draven shared valuable lessons on how taking outside investment impacts exit strategies, stressing the importance of market timing, investor expectations, and strategic foresight.

Resilience and Entrepreneurial Growth Draven opened up about his early life challenges, including being homeless at 18, and how those experiences shaped his mindset. Once something he hid, his story has now become a source of strength, teaching him resilience and empathy. Michael pointed out that Draven’s grounded approach to entrepreneurship reflects a focus on survival and practical outcomes rather than distractions. Draven shared how his mindset evolved from surviving to thriving—seeking growth and purpose beyond financial goals.

Journey to Personal Resilience Michael reflected on his own experiences of overcoming adversity, including a near-fatal heart attack and financial setbacks. These moments reinforced the importance of resilience and personal evolution. Both Michael and Draven agreed that while financial success matters, the deeper reward comes from self-development, expanding one’s potential, and learning through change. They discussed how continuous adaptation of tools, strategies, and mindsets is crucial for navigating both business and life’s transitions.

Klipboard.io’s Field Service Management Focus Draven shared insights into his company Klipboard.io, which was acquired by Carriage Commercial Systems in July 2024 and rebranded globally. Klipboard.io specializes in field service management software that empowers technicians in plumbing, HVAC, and fire equipment industries through digital tools for operations, quoting, scheduling, job management, invoicing, and accounting. Michael connected this to his own consulting experiences, emphasizing the importance of technology that simplifies processes instead of complicating them. Draven agreed, underscoring how meaningful it feels to deliver solutions that make technicians’ work more efficient and rewarding.

Benefits of Field Service Software Together, Michael and Draven explored how Klipboard.io’s platform helps field service teams streamline workflows and reduce operational bottlenecks. By automating manual processes, businesses can increase their capacity and focus on serving clients. Draven noted that many service companies still lack modern digital systems, making tailored solutions essential for improving productivity and profitability. Both emphasized the power of listening to users and designing around their real-world needs for stronger adoption and measurable results.

Collaboration and Feedback in Leadership Draven and Michael closed the conversation by discussing leadership, collaboration, and the importance of feedback in building great products and organizations. They highlighted that simplifying processes, including diverse perspectives, and inviting constructive input lead to better outcomes. Draven shared that surrounding himself with knowledgeable, thoughtful people has been key to his growth as both a leader and entrepreneur.

Connect with Draven Listeners can connect with Draven via his LinkedIn profile or his personal website. Learn more about Klipboard.io’s field service management solutions at klipboard.io.