In this episode of The Socially Awkward Podcast, host Calvin Tilokee sits down with hospitality icon Christine Trippi, founder of The Wise Pineapple and author of Yes Is the Answer: How Positivity, Passion, and Pineapples Will Transform Your Leadership and Your Life, to discuss how heart-first leadership, creativity, and strategy can drive both morale and measurable results. They explore how saying “yes” isn’t just about being agreeable—it’s about equipping teams with the tools to delight guests, increase revenue, and rediscover the joy of the job.

On this episode of The Socially Awkward Podcast, host Calvin Tilokee sits down with Melissa Maher, CEO of Pinnacle and former CMO of Expedia, for an insightful discussion on leadership in hospitality. Maher explores how digital transformation, DEI, and personal development intersect in today’s hospitality environment, drawing from her decades of experience in hotel operations, sales, and executive leadership.

Welcome to The Socially Awkward Podcast. In the latest episode, Calvin Tilokee sits down with Portia Smith, a seasoned travel creator and founder of Travel with Portia, to explore how content creators are shaping the future of hotel marketing. Portia’s journey from lifestyle blogging to a successful travel influencer has not only transformed her career but has also opened new doors for hotels seeking to build authentic relationships with their target audience. This episode dives into the nuances of influencer partnerships, the importance of creative freedom, and how clear communication can lead to lasting success for both parties.

In this episode of The Socially Awkward Podcast, host Calvin Tilokee speaks with Bruce Jordan, better known as the “MJ of Hotels.” He discusses transforming struggling hotels into thriving businesses through effective YouTube marketing. They explore Jordan’s journey from accounting clerk to multi-show content creator, the strategies that keep his channels relevant, and the realities of staying consistent in a crowded digital space.