Think you need 10 years of house flipping before you can go big in real estate? In this episode, Michael Blank sits down with Kent Ritter—Founder of Hudson Investing and host of Ritter on Real Estate—who scaled from solo operator to managing 2,000+ units and leading his own in-house property management firm. He didn’t wait for permission. He didn’t grind for a decade. He built systems, teams, and a killer culture that made scale inevitable.
They unpack how he made the leap from flipping houses to running a real syndication business, and why skipping the “single-family hustle” may be the smartest move you can make. If you’re tired of thinking small, this episode will wake you up.
Key Takeaways
Why Single-Family Strategies Keep You Stuck
- Flipping and landlording create income—but not freedom.
- Most "passive" single-family models are just high-paying jobs in disguise.
- You don’t need 10 years of grinding to go multifamily—you need a mindset shift.
How to Build a Real Business (Not Just Do More Deals)
- Learn why Kent’s first plateau happened—and how he broke through it with the right partner.
- Discover how he scaled from 7 to 30 team members overnight by bringing property management in-house.
- Building culture and hiring to core values was Kent’s unfair advantage—here’s how to do it right.
The Hidden Challenge of Raising Capital
- Why your friends and family won’t take you seriously at first—and what to do instead.
- The #1 perception you must change to consistently raise from private investors.
- You don’t need to know everyone—you just need to earn trust and prove expertise.
Public-Private Partnerships: The Future of Development?
- How Hudson Investing makes new construction deals pencil in 2025 and beyond.
- Why cities are partnering with operators—and how that benefits your returns.
- The real risk difference between building new vs. buying value-add.
Why the Midwest Is Still Winning
- Kent breaks down why Midwest markets like Indianapolis and Fort Wayne are outperforming.
- Supply constraints = stronger rent growth and less risk—here’s where to look.
- Why Midwest deals may be boring… but boring works.
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