The Robin Hood Resort Story with Christian Osgood

Most real estate stories focus on the wins.

This episode is different.

Christian Osgood joins Dave Dubeau to share the full story behind the Robin Hood Village Resort deal that nearly cost him everything. Christian explains how he went from buying duplexes to acquiring a historic resort using seller financing and partnerships, only to discover major operational problems after closing.

The conversation covers hidden payroll issues, failed business plans, difficult partnerships, and the massive effort required to rebuild the property into a successful event driven resort.

Christian also shares how creative financing helped him scale to more than 600 units and why solving difficult real estate problems became his passion.

Key Topics Discussed

• Buying a historic resort with seller financing
• Hidden payroll and bookkeeping problems
• Why multifamily underwriting failed for hospitality
• Partnership mistakes and cash call problems
• Turning the resort into a music and event venue
• Scaling a business to survive a bad deal
• Lessons learned from creative financing
• The launch of Christian’s new book on creative real estate

Guest Information

Christian Osgood

Instagram: Christian Osgood Instagram

YouTube: Multifamily Strategy YouTube Channel

Book: The Book on Creative Real Estate on Amazon

Call To Action

To connect with Christian or learn more about creative financing strategies, reach out through Instagram, YouTube, or his new book.