If you wanna build a lifestyle hospitality brand, you must control the real estate. Guild units were stylishly appointed. Common areas had large gyms & zero-edge rooftop pools. Yet, the ground floor was lacking… confusing arrival experience, vibe-free. Alas, we weren’t gonna compete with Hoxton and the Proper with these limitations. Before investing into a hotel brand make sure your landlord shares your product vision.

Venture is a power law game. VCs mostly strike out but occasionally hit a grand slam. FWIW, we had great VCs… insightful, supportive & founder-centric. Fellow founders: unless you’re committed to building a decacorn, do not raise $10m+ from VCs. At that point, you’ve burned the boats. You see, The Guild was a property management company in sheep’s clothing. Our tech was useful though not defensible. Our brand was well-liked but seldom known. The world’s largest hotel manager Aimbridge has taken 20 years and $700m of capital to attain a $1 billion valuation. Oof.

In hospitality, most value accrues to the landlord, some to the brand, minimal to the property manager. Blackstone invests $10B/yr into hotels with double digit annual returns. Marriott is worth $68B. Aimbridge is worth $1B. Modern brand exits have been scarce… Kimpton $430m, One Fine Stay $170m, Graduate $210m, Bunkhouse $25m. Several recent founders have launched PropCos to acquire assets and OpCos to manage them. Done well this structure can enable both high brand standards and asset appreciation.

Early days, when 20 of us managed our 5 Austin locations, our average guest rating was 4.9. Fast forward to 2020, when 150 of us managed 16 locations in 4 markets, our rating had dropped to 4.5. Our team was A+ throughout. However, we as founders failed to meticulously train, motivate and reinforce the culture. We’d recommend two books about scaling a strong hospitality culture: “Peak” by indie hotel OG Chip Conley and “Setting the Table” by acclaimed restaurateur Danny Meyer.

Brian and Chris shared the CEO crown the first 4 years. Early on, the arrangement worked. We debated in private and communicated a united front to the team. As we grew, cracks emerged. Our styles and visions diverged. Factions formed... Brian’s hires vs. Chris’ hires. If someone didn’t like the answer she got from Brian, she’d ask Chris, and vice versa. Kinda like parenting. COVID and its aftermath demanded decisive leadership, so Brian assumed the sole CEO role. This change was overdue. Fellow founders should think twice before pursuing the Co-CEO path.