EP 89: She Made Money (And Still Regretted These Real Estate Decisions in 2025)

In this episode, Courtney sits down with her student Colleen Gallagher for an honest, behind-the-scenes look at what 2025 actually looked like as a wholesaler experimenting with multiple Real Estate strategies.

From wholesaling and creative finance to managing a highly intensive shared-housing property, Colleen breaks down where she made money, where she lost time, and which decisions she would absolutely rethink if given the chance. This conversation is less about chasing the next strategy and more about learning when to simplify, refocus, and protect your time, energy, and systems as an operator.

If you are navigating shiny-object syndrome, trying to scale responsibly, or questioning whether a “cash-flow-heavy” strategy is really worth the management cost, this episode will hit close to home.

In This Episode, We Cover:

-Why wholesaling felt accessible but still required focus to stay profitable

-What Colleen learned from running a management-intensive shared housing property

-How chasing multiple strategies impacted her time, health, and overall returns

-Lessons learned from a rent-to-own deal gone wrong and tightening application processes

-The importance of systems, paperwork, and operational discipline in today’s market

-Why simplifying her approach is central to her Real Estate focus in 2026

-Letting go of “cheap deals” in favor of better neighborhoods and long-term appreciation

-Creating boundaries between business growth and personal well-being

Making money doesn’t always mean you’re moving in the right direction. Sometimes the most valuable lesson is learning which strategies are costing you more than they’re giving back.

Connect With Colleen Gallagher:

Instagram: https://www.instagram.com/investingwithcolleen/

Website: investingwithcolleen.com

Connect with Courtney Fricke: Website: www.CourtneyFricke.com (additional resources and workshops)Instagram: https://instagram.com/courtneyfrickeYouTube: https://www.youtube.com/@UCfZlfkGpNzcMuDh6NX7xVpQTikTok: https://tiktok.com/@courtney.frickeFacebook: https://www.facebook.com/courtneyfricke19/X: https://x.com/courtneyfricke

Subscribe to the podcast and stay tuned for more real conversations about strategy, growth, and building a Real Estate business that works for your life, not against it.