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The Hotel Investor Playbook
Welcome to The Hotel Investor Playbook, hosted by real estate investor and hospitality operator Michael Russell. Michael is the co-founder of Malama Capital and Howzit Hostels, and has built a personal real estate portfolio exceeding $20 million.
With an operator-first mindset, Michael brings a practical perspective to hotel investing. On the show, he breaks down what it actually takes to scale from short-term rentals into boutique hotels, covering deal sourcing, operations, capital strategy, and risk.
Each week, Michael shares real lessons from the field as he builds toward a $400 million real estate business, giving listeners an honest look at the decisions, challenges, and strategies behind the growth. Subscribe and follow along as he documents the journey in real time.
The Hotel Investor Playbook
The $0-Down Hotel Deal That Still Cost $1.5 Million | Christian Osgood E85
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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.
In this episode, you'll discover:
- Spot the hidden payroll problem that makes a mom-and-pop hotel's books lie to you
- Avoid the seller-financing structure that can wipe out a full year of cash flow in one payment
- Turn dead event space into guaranteed income through master leasing, fixed checks every month, with zero staffing or cleanup
- Combine a $1,000 a month ad budget with free community events to drive a 43% profit jump in twelve months
- Apply the deal, debt, equity framework before you ever start looking for investors
- Decide when a joint venture beats a syndication so you can skip the legal headaches
If you're underwriting a boutique hotel or resort deal, this conversation could save you from learning these lessons the expensive way.
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Connect with Christian Osgood
Website: https://multifamilystrategy.com/
YouTube: https://www.youtube.com/@Multifamilystrategy
LinkedIn: https://www.linkedin.com/in/christian-osgood-10a95b71
Connect with Michael on Instagram or LinkedIn.
Email Us at info@hotelinvestorplaybook.com
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