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Episode 378: Let Your Weird Flag Fly, with Emily P. Dailey

Destination On The Left

Release Date: 05/15/2024

457. Inside NTA Travel Exchange, with Nicole Mahoney  show art 457. Inside NTA Travel Exchange, with Nicole Mahoney

Destination On The Left

On this episode of Destination on the Left, I’m at the NTA Travel Exchange in Ottawa to speak with eight leading professionals shaping the future of group travel, tourism, and hospitality. You’ll hear insights from leaders who share the latest market trends, traveler behaviors, innovative approaches, and what’s ahead for 2026. The conversations explore the strong resurgence of group tours, the rise of small group and multi-generational travel, and a growing demand for immersive, meaningful experiences—from stargazing in Utah to luxury train journeys. You’ll discover how industry...

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456. How Travel Priorities Have Evolved, with Erin Groh show art 456. How Travel Priorities Have Evolved, with Erin Groh

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On this episode of Destination on the Left, I talk with Erin Groh, Head of Marketing at iSeatz, a leading but often behind-the-scenes travel tech company powering loyalty programs for brands like American Express, IHG Hotels & Resorts, and Qantas. Erin shares her fascinating career journey from traditional and digital media through to travel technology, illustrating how influencer marketing, social media, and travel tech are now converging to reshape the modern travel experience. Listeners will find out why today’s travelers are prioritizing dream trips—even if it means rebalancing...

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455. Making Travel Accessible and Eco-Friendly Across Europe, with Oliver Winter show art 455. Making Travel Accessible and Eco-Friendly Across Europe, with Oliver Winter

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On this episode of Destination on the Left, I talk with Oliver Winter, CEO and Founder of a&o Hostels, for an inspiring conversation about his entrepreneurial journey, from traveling on a shoestring budget to building one of the largest hostel brands in the world. We talk about his focus on being a cost leader, not a price leader, and how that translates to a guest experience that works for small pockets while still serving the needs of his guests. Oliver also shares his passion for sustainability and how his company has been able to move from an 18-kilogram per guest carbon footprint to...

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454. What Makes Atlantic Canada’s Tourism Scene Unique, Atlantic Canada Roadshow 2025 Part 2 show art 454. What Makes Atlantic Canada’s Tourism Scene Unique, Atlantic Canada Roadshow 2025 Part 2

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We’re taking you on a road trip through the future of tourism in Atlantic Canada. You’ll hear firsthand from tourism leaders on how the region captivates new generations of travelers while staying true to its maritime roots. We also spotlight the rise of Indigenous-led travel experiences and the wave of creativity from local artisans. From group travel trends to the power of regional collaboration, each story underscores how Atlantic Canada’s tourism pros aren’t just adapting—they’re shaping what meaningful travel looks like for the years ahead. In this episode, you’ll hear from...

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453. News from the Atlantic Canada Roadshow 2025 Part 1 show art 453. News from the Atlantic Canada Roadshow 2025 Part 1

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This week on Destination on the Left, we bring you the first special roadshow installment from the Atlantic Canada Showcase 2025 in beautiful Saint John, New Brunswick. In this episode, we dive into the deep-rooted community spirit and storytelling tradition that make Atlantic Canada such a fantastic destination. You’ll hear firsthand from passionate tourism professionals across the region, who will share powerful insights on how authenticity, connection, and collaboration are shaping travel experiences in Atlantic Canada—offering everything from local cuisine and hands-on adventures to...

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452. How Dot Vegas Connects Travel, Technology, and Marketing, with Chris Mondini & Dusty Trevino show art 452. How Dot Vegas Connects Travel, Technology, and Marketing, with Chris Mondini & Dusty Trevino

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On this episode of Destination on the Left, I talk with Chris Mondini, Vice President of Stakeholder Engagement and Managing Director of Europe for ICANN, and Dusty Trevino, CEO of Dot Vegas. We will learn how top-level domains are created and what domains like Dot Vegas can do to help a brand stand out. Our conversation is informative, educational, and will give you a whole new perspective on your brand’s Internet address. What You Will Learn in This Episode: How top-level domains (TLDs) are created and why the addressing system of the Internet matters Why distinctive TLDs, like Dot...

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451. How Travel Alberta’s Wild Side is Bringing International Visitors to Canada, with Tannis Gaffney show art 451. How Travel Alberta’s Wild Side is Bringing International Visitors to Canada, with Tannis Gaffney

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On this episode of Destination on the Left, I talk with Tannis Gaffney, Chief Marketing Officer of Travel Alberta. Tannis walks us through the strategy behind Canada’s wild side branding and the secret behind making their brand permeate everything they do. She shares more about Travel Alberta’s collaboration with Indigenous Tourism Alberta and how that relationship has evolved, opening up new immersive cultural experiences for the right types of travelers. What You Will Learn in This Episode: Why Alberta chose to reposition its brand around “Canada’s Wild Side” and how leaning into...

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450. Community Conversations on Tourism Partnerships and Collaboration show art 450. Community Conversations on Tourism Partnerships and Collaboration

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On this episode of Destination on the Left, I bring together three trailblazers for a candid community conversation about the heart of collaboration in the travel and tourism industry. Joining are Dave Herrell, President and CEO of Visit Quad Cities; Rebecca Mackenzie, President and CEO of the Culinary Tourism Alliance; and Sage Hamilton-Hazarika, Corridor Coordinator for the Underground Railroad Consortium of New York State. Together, we discuss what true collaboration looks like, and the panel explores how putting trust, vulnerability, and outcomes over ego unlocks success not just in...

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449. Using LinkedIn for Authentic Engagement, with Greg Star show art 449. Using LinkedIn for Authentic Engagement, with Greg Star

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On this episode of Destination on the Left, I talk with Greg Star, Founder of Driven Authentic Branding Solutions, who shares how he helps destinations stand out using LinkedIn. He discusses why it is important to lean into thought leadership posts both for the company profile and the people who work there. Greg shares some real-life examples of results that his clients are seeing and how you can identify your content pillars and find your voice. What You Will Learn in This Episode: How Greg’s personal journey reshaped his outlook on business and inspired the launch of his latest company...

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448. Key Insights for a Collaborative 2026, with Nicole Mahoney show art 448. Key Insights for a Collaborative 2026, with Nicole Mahoney

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On this episode of Destination on the Left, I’m taking you behind the scenes of my own year-end planning process. As we look ahead to 2026, I’ll walk you through how I reflect on the past year, celebrating what worked, identifying lessons learned, and checking in on both team and personal well-being. I share everything from my practical planning frameworks and financial benchmarks to trend forecasting and tips for creating a collaborative culture. What You Will Learn in This Episode: Why intentional reflection and bold, future-oriented questions are essential for setting effective...

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More Episodes

On this episode of Destination on the Left, I talk with Emily about how her creative skills and early experience in theater led her to the hospitality industry. She walks us through a process for evaluating your brand and thinking about it from a people-first perspective and shares her approach to addressing challenges that cover planning for short-term, mid-term, and long-term needs in that order.

What You Will Learn in This Episode:

  • The importance of building relationships before seeking mentorship and why creating a culture of collaboration establishes trust and open communication
  • How Emily manages imposter syndrome by addressing her “shadow Emily” and seeking support to counter negative thoughts
  • How to build genuine connections and create communities aligned with individual needs
  • How Emily helps her clients let their weird flag fly so that all of their people can find them
  • The connection between hospitality and wellness, and why Emily’s company also serves the wellness industry as they both aim at ensuring people’s well-being and contentedness

Aligning Brand Identity with Organizational Culture

I loved discussing the alignment of brand identity with organizational culture with Emily on the show. Drawing a parallel between developing a script for a story and developing a brand for a hotel, Emily highlights the interconnectedness of a business’s branding with the patterns of corporate behavior and people within an organization. Understanding your brand inside out is what helps you connect with your ideal clients.

Building Relationships and Establishing Trust in Business

Drawing from her experience in the Hotel Sales and Marketing Association International, Emily discusses the importance of building strong relationships before seeking mentorship. She talks about how to create a culture of collaboration, where open communication and trust are built through genuinely supporting and connecting with other people. On the show, we talk more about some creative ways Emily has moved through challenges and the framework she uses to keep her on the right path.

Overcoming Imposter Syndrome and Nurturing Authentic Connections

We also dig into the topic of imposter syndrome during the podcast, particularly the importance of acknowledging and addressing fear-based thoughts that are blocking your personal and professional growth. Emily shares her method of addressing her “shadow Emily” and seeking support from friends to move past any negative thoughts. This prompted our discussion on the importance of making genuine connections with others and the power of compliments and appreciation in establishing authentic, collaborative relationships.

Resources:

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