What do a Japanese apprenticeship, a career in luxury hospitality, commercial real estate, and 45 years of martial arts have in common? According to Andrew Benioff, they all teach the same lesson – growth rarely comes from comfort. Andrew shares stories from his time living in Japan, apprenticing at a traditional ryokan, working with the Ritz-Carlton, and eventually becoming a real estate investor and developer. He and Doug explore resilience, failure, mindfulness, and why some of life’s most valuable lessons come from learning to sit with discomfort instead of avoiding it.

Andrew has 25+ years’ experience in real estate finance and transactional activities and 15 years experience in the operation and management of luxury hotels. He is the founder of the Independent Lodging Congress, the premier gathering of independent hoteliers, restaurateurs, designers, financiers, investors, tech start-ups and media companies focused on the independent and boutique hospitality sector. He is also the Founder and Chairman of the Philadelphia Real Estate Council, a nonprofit organization of real estate executives focused on the mid-Atlantic region.

Two restaurateurs get real about what it takes to build something of your own — long hours, real pressure, and getting your team to believe it’s all worth it.  Alex shares how his experience with Ralph Lauren and Four Seasons Hotels & Resorts shaped the way he approaches building Bar Rêve from the ground up. Doug talks about the good kind of stress, and they both agree that the best ideas don’t stay in one industry.

Alex is Co-Founder of Bar Rêve in New York City. He has been featured in Vogue, The New York Times, and LOOP, and speaks globally on how luxury brand experience translates into independent hospitality.

Amy and Doug have a shared love of boutique hotels. But as entrepreneurs and business owners, they cover a lot of ground in this lighthearted discussion about generosity, lessons learned, and how people are their favorite part about their jobs.

Amy is a Principal at Hatteras Sky, a commercial real estate development firm with properties across the country, committed to creating places that move, inspire, and serve as the backdrop for lifelong memories. Her properties have received national acclaim, with restaurants earning placement in the Michelin Guide for the Southeast.

Omar is a true champion of the boutique hotel and a firm believer that the right story can transform a property. This episode is a deep dive into why storytelling isn’t just creative fluff, but a strategic advantage. Call it “Storytime with Omar and Doug” — a conversation about helping brands of all kinds uncover what makes them distinct and worth desiring.

Creative Director at Studio Circa, Omar helps bridge the emotional gap between people and place by designing brand platforms that reflect the soul of boutique hotel properties with a focus on driving direct bookings and long-term appeal. He also partners with developers early in the process to shape brands that elevate perceived value and ROI in real estate with the maxim – Distinction Drives Desire.

We love a good Founder Story and Rob’s will inspire and encourage. Doug and Rob go down memory lane from their beginnings as young founders building their own websites on Flash (before websites were popular), to still loving what they do 20-plus years later. They also cast their prediction on how technology will help or hurt us when it comes to serving what matters most – people.

Rob began his hospitality career at the age of 26, as the innkeeper of an 8-room bed and breakfast on Nantucket Island in Massachusetts. As the Founder and Chairman of Lark, Rob is now the steward of a portfolio of real estate valued at nearly $1B with an annual revenue stream over $150MM. Rob takes pride in having worked every position in his hotels, from toilet scrubber to line cook to general manager and attributes the success of Lark, not only to his ability to learn on his feet, but mostly to his knack for bringing amazing people together.

From imposter syndrome to sleazy sales techniques to founderitis (definition in the podcast), Doug and Laura tackle some of the toughest challenges facing business leaders. Laura speaks with transparency, conviction, and a healthy dose of humor. This is an honest conversation that leaders in all industries can relate to.

Laura helps B2B industrial innovators boost their marketing ROI through targeted, technical digital strategies that drive real sales impact. She digs deep into business processes and existing marketing to build customized, audit-driven plans. Known for her high standards, collaborative approach, and holistic view of sales and marketing, she consistently delivers solutions that exceed expectations.

The hotelier and the hotel enthusiast get together to talk about their most memorable hotel stays, what the hospitality industry is doing right, where authenticity fits in and how to scale yourself without losing your mind.  Doug and Bashar always have a great time together and this discussion does not disappoint. 

Bashar is the founder of This Assembly – born to build hotels with a heartbeat. With hospitality as the front and humanity as the truth, Bashar’s mission is to keep hospitality sacred, not scalable by creating spaces that make people feel.

Doug and Moira take a deep dive into the sea of attribution and analytics. Swimming with numbers might not be fun for everyone but in this discussion they share some eye opening stories about navigating client expectations and coming up with a single source of truth.

Moira Miller is an organized, motivated, and innovative Marketing Leader with over a decade of agency experience; executing effective marketing strategies, growing businesses, and building impactful teams. She specializes in Saas, Technology (Tech, FinTech, MarTech), Professional Service (B2B, B2C), and mission-based organizations.

Two wild and crazy guys confirming that human connection trumps all. From discussing the value of creating great content, to connecting virtually, to human versus AI power…these two cover it all. 

Christopher is the very definition of a polymath living at the intersection of art, business, design and creativity. Founder of KISMET COWORK and RADIOKISMET, Christopher has an extensive background in audio, performance and film.