Starting A Real Estate Business in 2007 & Thriving 20 Years Later featuring Jeff Nydegger

In this episode of the Collective Genius Podcast, I’m thrilled to welcome Jeff Nydegger, a dynamic real estate investor out of Chicagoland, to unpack his journey of building a resilient and values-driven business. Jeff and his partner Kevin have been at it for nearly two decades, and in this conversation, we dig deep into the lessons they’ve learned from both their wins and their challenges. From military discipline to Midwest grit, Jeff shares how he’s navigated market downturns, stayed laser-focused on his mission, and leveraged the power of mastermind groups like Collective Genius to sharpen his leadership and strategy.

 

We explore everything from business partnerships and team-building to market pivots and personal growth. Whether you’re looking to build a business that lasts or sharpen your execution after your next mastermind event, Jeff’s insights are a masterclass in what it really takes to succeed long-term in real estate.

 

Expanded Episode Highlights:

[0:00] - Intorduction

[3:12] - Jeff’s roots in Iowa, his military background, and the unexpected path that led to real estate.

[7:05] - Early dreams, sports, and how a competitive spirit fuels business success.

[14:45] - How Jeff and Kevin built a 20-year partnership rooted in trust and clear roles.

[26:10] - The “real talk” about starting a business in the 2007 housing crash.

[34:50] - Why short sales became their breakout niche—and how they mastered it.

[42:30] - Designing a business for your life, not someone else’s blueprint.

[48:15] - Why clear vision + strong execution = scaling without burnout.

[55:30] - The power of mastermind groups and how Jeff filters information to avoid overwhelm.

[1:02:05] - Top leadership books and why Jeff swears by The Five Dysfunctions of a Team.

[1:08:20] - How to connect with Jeff and his team—and his hilarious “Facebook jail” story.

 

5 Key Takeaways:

 

1. Trust is non-negotiable. Jeff credits his long-running partnership to mutual respect and never stepping into each other’s lanes.

2. Filter, focus, and execute. Mastermind groups offer endless ideas—but the real magic is knowing what not to act on.

3. Design YOUR business. Jeff reminds us that success isn’t one-size-fits-all; it’s about aligning your business with your life values.

4. Leadership starts with you. Whether in the military or the boardroom, leading by example builds trust and lasting culture.

5. Stay humble, stay hungry. Even with nearly 20 years in the game, Jeff stays connected to mentors and peers, proving that growth is a lifelong journey.

 

 

Links & Resources:

 

• Jeff’s company: JeffBuysYourHouse.com

• Learn more about Collective Genius: thecollectivegenius.com

• Recommended reading: The Five Dysfunctions of a Team by Patrick Lencioni, The 7 Habits of Highly Effective People by Stephen Covey.

 

 

Thanks for tuning in! If you loved this episode, please rate, follow, and share the podcast. Your reviews help us reach more investors ready to scale with intention. Catch you next week for another conversation with a genius!