The hospitality industry has weathered enormous shifts in the last five years, from pandemic‑era shutdowns to evolving guest expectations. Although hotels are projected to add over 14,000 employees in 2025, staffing levels are still well below pre‑pandemic (2019) figures. For hotel professionals, visibility and adaptability are critical, not only in operations but in how they share expertise. YouTube marketing has emerged as a powerful, SEO‑driven platform for building an audience, yet many in hospitality struggle to gain traction. In the realm of video marketing, 90 % of marketers say video has helped them generate leads, though success often demands more strategy than just recording content.

How can hospitality professionals translate industry expertise into engaging, monetizable content that attracts both viewers and brands?

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.

Highlights from the conversation:

• Content that works: Entertainment is non-negotiable, even for technical topics; hook viewers in the first few seconds.
• Growth strategies: Use SEO principles for video titles, descriptions, and tags to capture both YouTube and Google search traffic.
• Sustainable creativity: Repurpose long-form videos into short reels, take strategic breaks, and leverage tools like VidIQ to track trends.

Bruce Jordan is a hotel revenue generation expert, hospitality consultant, and author of The Hotel Revenue Bible. He has trained with leading brands including IHG, Hyatt, Wyndham, Hilton, and Marriott, and is recognized as a Top 25 Social Media Influencer in Hospitality from 2021–2025. As Managing Partner of Hotel Guest Management, he has turned around underperforming hotels, created high-impact YouTube shows on hospitality best practices, and built a strong reputation for driving revenue, guest satisfaction, and digital marketing success.

Influencer marketing is rapidly changing, and many hotels are still figuring out how to tap into its full potential. As travelers demand more authentic and relatable content, the pressure is on for hotels to adapt their marketing strategies. But with skepticism around the true ROI of influencer partnerships, it’s more important than ever for brands to learn how to create meaningful, long-lasting collaborations that drive real engagement and loyalty.

How can hotels and influencers work together to create mutually beneficial partnerships that go beyond just a post or a story?

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.

Key Takeaways from the Episode:

The shift from transactional influencer partnerships to long-term collaborations for sustainable growth.

The importance of clear communication and setting expectations to ensure both hotels and influencers are aligned.

How influencers like Portia can help hotels connect with audiences through authentic and relatable content, driving future bookings and brand loyalty.

Portia Smith is a renowned travel creator and the voice behind Travel with Portia, where she shares her passion for travel, adventure, and inspiring women to explore the world. After starting her journey in 2015 as a lifestyle blogger while navigating motherhood, Portia quickly transitioned into the travel space and began curating memorable experiences for her audience. With a background in content creation and a focus on women’s travel, Portia leads group trips to destinations like Tuscany, Bali, and Costa Rica, all while building an engaged community of travelers.

The hospitality industry is under mounting pressure to modernize to meet guest expectations for seamless, tech-driven experiences and also develop leaders who can drive that transformation. According to Rackspace Technology, only 28% of travel and hospitality companies qualify as “AI leaders”— those aligning strategy, compliance, and training with real-world deployment. Another 28% remain in a passive “wait-and-see” phase, experimenting minimally or not at all. Despite visible progress, a wide gap persists between early adopters and the rest of the industry. As technology reshapes both operations and guest expectations, hospitality career development is also evolving, demanding new leadership capabilities, inclusive practices, and an innovation-first mindset.

What will it take for hospitality leaders to fully embrace modern technology, inclusive leadership, and adaptive career paths in a rapidly shifting industry?

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.

Highlights from the Episode:

• Why tech adoption in hospitality remains slow, and how Maher believes AI can be used beyond cost-cutting to drive revenue and enhance guest experiences.

• The real value of diversity: How Maher integrates inclusive leadership in her coaching cohorts and why she created the Pinnacle Pay It Forward program.

• How hospitality career development is shifting in response to innovation, requiring leaders to build networks, take smart risks, and adapt to new guest and workforce expectations.

Melissa Maher is a seasoned hospitality executive with over 20 years of experience, including senior leadership roles at Expedia, where she led global marketing, strategic partnerships, and the company’s first diversity and inclusion initiatives. As CEO of Pinnacle Enterprises Group, she now empowers executives through leadership development programs focused on executive presence, personal branding, and inclusive strategy. Maher is widely recognized for her expertise in commercial negotiations, DEI, and tech-enabled hospitality innovation, having secured over $1B in hotel partnerships and guided leaders across multiple industries.

As the hospitality industry emerges from years of pandemic-driven upheaval, leaders are iv As the hospitality industry emerges from years of pandemic-driven upheaval, hospitality leadership is evolving to meet new challenges. Leaders are looking for new ways to retain staff, elevate guest satisfaction, and drive revenue without burning out their teams. One trend gaining traction is the power of “Yes”: empowering employees to say yes more often, guided by creativity and compassion. According to a December 2024 AHLA survey, nearly 65% of hotels continue to report staffing shortages, putting added pressure on frontline staff. Could a shift in service mindset be part of the solution?

So, how can hospitality leaders balance guest satisfaction, staff empowerment, and business success—all while learning to say “yes” more often?

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, 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.

Key Takeaways from the episode…

Saying “Yes” Sparks Revenue, Not Just Satisfaction: From late checkouts to pillow forts, Christine explains how creativity in guest service leads to monetizable experiences—and happier teams.

Empowered Teams Retain Better: Staff who are encouraged to say yes and lead from the heart are more engaged and less likely to leave, helping reduce costly turnover.

Transformation Starts with Vision: Christine outlines her three-step framework for turning around struggling hotels—starting with a clear, shared goal, strategic focus, and an actionable plan.

Christine Trippi is a 34-year hospitality veteran and award-winning hotelier known for transforming hotel operations and culture through frontline empowerment and heart-first leadership. As the founder of The Wise Pineapple and best-selling author of Yes Is the Answer, she consults, trains, and speaks nationally to help leaders create high-performing teams and exceptional guest experiences. Her career spans roles from Marriott Senior Operations Manager to keynote speaker, TEDx presenter, and podcast host, with expertise in customer service, employee training, and operational excellence. According to a December 2024 AHLA survey, nearly 65% of hotels continue to report staffing shortages, putting added pressure on frontline staff. Could a shift in service mindset be part of the solution?

So, how can hospitality leaders balance guest satisfaction, staff empowerment, and business success—all while learning to say “yes” more often?

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, 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.

Key Takeaways from the episode…

Saying “Yes” Sparks Revenue, Not Just Satisfaction: From late checkouts to pillow forts, Christine explains how creativity in guest service leads to monetizable experiences—and happier teams.

Empowered Teams Retain Better: Staff who are encouraged to say yes and lead from the heart are more engaged and less likely to leave, helping reduce costly turnover.

Transformation Starts with Vision: Christine outlines her three-step framework for turning around struggling hotels—starting with a clear, shared goal, strategic focus, and an actionable plan.

Christine Trippi is a 34-year hospitality veteran and award-winning hotelier known for transforming hotel operations and culture through frontline empowerment and heart-first leadership. As the founder of The Wise Pineapple and best-selling author of Yes Is the Answer, she consults, trains, and speaks nationally to help leaders create high-performing teams and exceptional guest experiences. Her career spans roles from Marriott Senior Operations Manager to keynote speaker, TEDx presenter, and podcast host, with expertise in customer service, employee training, and operational excellence.