The Hotel Investor Playbook · 2026-06-16 · 54 min
It took zero dollars of his own money to buy a $4.5 million waterfront resort. It took three years and over a million and a half dollars out of pocket just to keep it. In this episode, you'll discover the deal, debt, equity sequence he says has never failed to raise capital on a good deal, and exactly when a joint venture beats a syndication. A multifamily investor who scaled to over 600 rental units, and once raised $10 million without a following or a dollar from family, walks through the one hospitality deal that broke all his usual rules. Christian Osgood unpacks exactly where his due diligence missed the mark, and the strategy he used to turn a struggling resort into a self-sustaining cash machine.
How a $800K Distressed Motel Became a $2.4M Revenue Machine | Michael Russell E8773 / 100The Wellness ROI Audit Every Boutique Hotel Owner Needs to Run | Emily Johnson E86The Boutique Hotel Mistake Killing Your Occupancy (And the Fix That Took One Operator From 40% to 80%) | Hillary Folkvord E84
From $50 in His Bank Account to a 140-Key Hotel in Italy | Emanuele Pani E83
This Contractor Built a $6M Hospitality Brand With $90K and Zero Outside Investors | Chris Broomfield E82