An active investor for 20 years, Jonathan has been involved in over $10 billion of real estate transactions worldwide in the hospitality, office, and residential sectors, focusing on hotels. Prior to founding EOS in 2017, he was with Northwood Investors from 2007 to 2016, where he served as a Managing Director from 2009 to 2016, overseeing the acquisition and asset management of its hotel portfolio. Jonathan oversaw the hotel investment process for Northwood Investors, which included over $940.0 million of equity.On this episode, Jake and Jonathan discuss:Finding and structuring dealsGauging riskDebt strategiesRate ceilingsStrategy sessionsBuilding a vertically integrated organizationSetting incentivesLinks:EOS InvestorsJonathan on LinkedInGirls Like Us by Cristina AlgerThe Great Game of Business by Jack StackIsla Bella Beach ResortConnect & Invest with Jake:Follow Jake on Twitter: https://twitter.com/jwurzakTake the Hospitality Investing Masterclass: https://learn.jakewurzak.com/Learn How to Invest with DoveHill: https://bit.ly/3yg8PwoTopics:(00:00:00) - Intro(00:02:01) - Jonathan’s career hospitality(00:05:52) - How are you finding and structuring deals?(00:10:05) - Gauging risk(00:14:18) - Succeeding in hospitality as an outsider(00:20:46) - Debt strategies(00:25:51) - Evaluating market supply(00:28:12) - Rate ceilings(00:31:50) - Why Jonathan chose hospitality(00:33:49) - Most important learnings about hospitality(00:37:49) - Rationalizing having a diverse portfolio(00:45:06) - Strategy Sessions(00:50:15) - Improving communication flows(00:57:20) - Building a vertically integrated organization(01:03:17) - Building EOS(?)(01:09:01) - Incentivizing people(01:14:38) - Where investments go wrong(01:17:13) - What is your favorite hotel?