In this personal and tech-forward episode of The Stash Cast, host Stash dives into heritage, hustle, and high-tech with John Reilly — a seasoned investment banker turned CEO of PGE Inc.

John opens the show with a powerful look at his Irish ancestry, tracing the lineage of the O'Reilly clan back to kings, castles, and coat-of-arms lore. Then, he shifts gears and takes us on a journey through his eclectic career — from practicing Chinese medicine to building wealth management firms and leading innovation in the proptech space.

Now at the helm of PGE Inc., John shares how his team is using multi-agent generative AI to completely transform the apartment rental experience — from automated listing creation and personalized marketing to conversational leasing agents and predictive maintenance coordination.

This episode is a rare mix of legacy and future, roots and disruption — perfect for anyone curious about how deep experience and emerging technology can converge to reshape real estate.

🎙️ Stash Cast with Lee Kiser | Inside the Mind of a Multifamily Brokerage Leader 🏢

In this episode of Stash Cast, we sit down with Lee Kiser, Co-Founder, Principal, and Managing Broker at Kiser Group, for a wide-ranging, candid conversation about the evolution of multifamily real estate, building a values-based brokerage, and where the industry is headed.

Lee shares his journey from founding a boutique real estate firm in Chicago with his wife to expanding across multiple states—including Illinois, Indiana, Wisconsin, Michigan, and Ohio—with a new office in Minneapolis. With nearly three decades in the industry, Lee dives deep into what it really takes to build trust, outwork the competition, and lead with integrity in a notoriously cutthroat market.

Whether you're a broker, investor, or entrepreneur, this episode offers a rare behind-the-scenes look at what separates lasting success from fleeting wins in real estate.🔍 Key Insights:

* Culture is Everything: Kiser Group was built on a strict “no-jerk” policy—prioritizing collaboration, transparency, and mutual respect across all hires.

* Client-First Mentality: Putting the client's interests above all else—even if it means walking away from a deal—creates loyalty that lasts decades.

* Market Differentiation: In Chicago, mid-market firms like Kiser Group outperform larger national names through niche specialization and hyper-local knowledge.

* Architectural Intelligence: Understanding physical property characteristics (like vintage plumbing or “four-plus-one” construction) can reveal hidden risks and opportunities during underwriting.

* Tech + Grit = Advantage: While larger firms may offer scale, smaller firms like Kiser Group bring relentless hustle, sharper analysis, and a personal touch.

* Future of Brokerage: AI, machine learning, and blockchain will transform real estate—but not replace the human insight, empathy, and nuance required in high-stakes deals.

✅ Takeaways:

* Don’t Compromise on Principles: Clear values like “clients first” and “no egos” provide the foundation for lasting success in any brokerage firm.

* Avoid the Off-Market Hype: Deals without transparency often come with higher risks and less value. True market pricing comes from real competition.

* Data is Power: Tracking every interaction, lead, and conversion sharpens strategy and improves outcomes—for both clients and brokers.

* Train Like You Mean It: Kiser Group’s training library includes thousands of hours of customized videos and resources, tailored to each agent’s market and role.

* Growth Should Be Purposeful: Expansion isn’t about size—it’s about bringing the right platform to the right talent in the right markets.

* Adapt or Fade: While real estate is still about people, the most successful firms will be the ones that evolve with technology—without losing their human edge.

📌 Whether you're breaking into the industry or refining your edge, this episode will challenge, educate, and inspire you.

👀 Watch now and gain timeless insight from one of the Midwest’s most respected real estate leaders.

In this insightful episode of Stash Cast, host Stash sits down with John Wijtenburg to unpack his journey through the financial crisis, commercial real estate, and building scalable businesses.

John shares hard-earned wisdom from scaling an eight-property hotel portfolio to now helping real estate entrepreneurs break past growth ceilings. Whether you're in hospitality or any investment-focused business, John’s approach to systems, strategy, and mindset offers game-changing insights.

✅ Key Takeaways:

💼 How John transitioned from residential real estate to commercial and hotel investing.

📈 What it's like building a hotel portfolio from scratch—while navigating market shifts.

📊 The operational intensity of hotels vs. other real estate asset classes.

🛠️ Why systems, SOPs, and execution frameworks are critical to scaling past 5–8 properties.

🧱 Why most founders need to shift from “being the business” to building the business.

🌎 How John built a 30-person offshore team to manage HR, compliance, legal, and more.

💬 The value of daily huddles and two-week sprints to create engagement in remote teams.

💡 Insights:

🧠 Vision → Strategy → Execution: Success starts with clarity of vision, which drives team alignment and operational decisions.

🔍 Double Diamond Framework: Avoid chasing shiny tools—solve real problems by first identifying root causes, then tailoring solutions.

⚙️ Use content as leverage: Beyond capital and code, content attracts talent, defines culture, and communicates your values.

🏨 Hotels are operating businesses first: Investors often underestimate how fast the cycle time is—and how fast things can go wrong.

📉 Don’t let your underwriting become gospel: Annual strategy resets lead to smarter, more adaptive operations.

🌐 AI, automation, and remote talent can transform productivity—if paired with the right culture and cadence.

🔥 Burnout is common at every level: Even $1B+ portfolios can fail if leaders don’t build systems that reduce decision fatigue.

💬 Whether you're a student, young professional, or someone just starting your wealth journey, John's candid insights and personal stories offer a refreshing and grounded perspective on finance.