CREATOR: The Podcast

This week, we're bringing back this conversation with Luke “Sailing Songbird” Hartley as an encore presentation - originally published February 25th, 2025. Solo World Sailor and Viral Creator Luke "Sailing Songbird" Hartley (@sailing_songbird) shares his remarkable journey from quitting his job as a middle school music teacher to sailing solo around the world on a 27-foot sailboat. In today's episode of CREATOR: the Podcast, we explore how Luke went from zero sailing experience to sailing solo around the world, learning everything through YouTube before embarking on his global circumnavigation. Luke reveals how his social media exploded from 300 to 100,000 followers in just five days - now sitting at around 2M, his content creation process while navigating remote waters, and surviving a 49-day Pacific crossing with no engine or communications. Discover how he’s producing long-form content for his YouTube channel, manages extreme isolation while maintaining a positive mindset, and turns his adventures into compelling content. Whether you're interested in adventure travel content, sailing vlogs, or building an authentic social media presence, Luke's insights on transforming a personal journey into viral videos offers valuable lessons for creators looking to document unconventional lifestyles. To learn more about CREATOR: The Podcast, visit creatorthepodcast.com 00:00 Introduction to Luke "Sailing Songbird" Hartley  02:05 From music teacher to sailing around the world  03:38 Learning to sail from YouTube videos  05:37 Quitting his job and buying a boat  07:10 Family reactions to his global sailing plans  09:32 Safety in the middle of the Pacific Ocean  12:13 Paddleboarding 1,000 miles from land  15:17 Sailing without an engine across the Pacific  17:29 Going from 300 to 100,000 followers in 5 days  19:07 Losing communication for 30 days at sea  21:51 Impact of his content on viewers' lives  23:51 Maintaining positivity through challenges  25:25 Content creation setup on a small sailboat  27:39 Overcoming creator's block and mental health  30:15 Life at sea: fishing and catching mahi-mahi  32:11 Preserving eggs with Vaseline for long voyages  34:37 Brand partnerships and monetization challenges  36:43 Future sailing plans and five-year itinerary  40:17 Favorite destinations: French Polynesia and beyond  42:56 Living off spearfished mahi for a month 44:21 Where to find Luke online

This week, we're bringing back this conversation with Jessica Nabongo as an encore presentation - originally published March 25th, 2025.  Content Creator and Travel Expert Jessica Nabongo (@jessicanabongo) joins CREATOR: the Podcast to discuss her journey as the first Black woman to visit every country in the world. She explains how reading about another traveler's global journey in 2017 inspired her to undertake her own mission to visit all 195 countries—completing it just months before the pandemic hit in 2019. Jessica offers a candid look at how she funded her travels without major brand partnerships, and the challenges of reaching remote destinations in the South Pacific and Central Africa. The conversation explores her evolution as a creator and entrepreneur: from launching a luxury travel agency to publishing with National Geographic, having her photography displayed at Christie's, and developing successful partnerships with major brands like Four Seasons and Expedia. Jessica also reveals her upcoming projects, including a new cookbook featuring one recipe from every country in the world, and shares honest advice about authenticity, financial management, and airline loyalty for aspiring travel creators. To learn more about CREATOR: The Podcast, visit creatorthepodcast.com 00:00 - Introduction to Jessica Nabongo: First Black Woman to visit every country 02:15 - Jessica's origin story: Growing up in Detroit with Ugandan parents 03:43 - Moving to Japan at age 23 05:38 - Learning Japanese and living as an expat 06:50 - Starting "The Catch Me If You Can" blog 08:44 - Following life's opportunities: Benin, Rome, and DC 09:22 - The decision to visit every country in the world 11:04 - The world of "country counting" and extreme travelers 12:35 - Strategy for visiting remaining countries 14:52 - The Seychelles: Jessica's final country celebration 16:47 - Post-journey: Media attention and the Nat Geo book deal 18:23 - Funding the journey: Working vs. brand partnerships 21:06 - Writing a book with National Geographic 24:27 - Highlighting underrepresented countries in her book 26:28 - Jessica's photography at Christie's auction house 28:37 - Recent brand partnerships: Four Seasons, Cadillac, and more 30:39 - Speaking engagements around the world 32:48 - Most lucrative aspects of Jessica's creator career 34:13 - Advice for aspiring travel creators: Find your "why" 36:33 - Jessica's new cookbook: "Catch Me in the Kitchen" 37:52 - Food origins and cultural identity through cuisine 39:19 - Jessica's top three countries if limited to only three 41:09 - Where to follow Jessica online

This week, we're bringing back this conversation with Wade Holland & Abby Wren as an encore presentation - originally published July 29th, 2025.  Wade Holland (@wadeholland) and Abby Wren (@abbywrenartistry), the adventure-art duo behind Wrenegade Media (@wrenegademedia), join CREATOR: The Podcast to discuss revolutionizing brand partnerships through collaborative creativity. As two creators with experience on the agency side, Wade and Abby reveal how brands can elevate their content and the common mistakes they see brands make that waters down good creative. Host Ross Borden explores their journey from individual creators to founding a creative agency, diving into Abby's transformation from behind-the-scenes makeup artist to viral face-painting activist, and Wade's evolution from adventure host to creative director. Whether you're a creator looking to scale beyond individual channels or simply interested in authentic storytelling that drives social impact, this conversation delivers valuable perspective on building purpose-driven content that cuts through digital noise. To learn more about CREATOR: The Podcast, visit creatorthepodcast.com 00:00 - Introduction to Abby Wren and Wade Holland 01:52 - Living in the Sonoran Desert 03:25 - The Love Story: How Wade and Abby Met 08:54 - Abby's Journey with Alopecia and Makeup Artistry 11:50 - Becoming a Professional Makeup Artist 14:38 - Using Art for Alopecia Awareness 16:37 - Building Renegade Creative Agency 18:22 - Partnership with GoPro Mountain Games 19:58 - Advice to Brands on Creative Campaigns 21:24 - Taking Creative Risks and Failing Fast 25:53 - The Challenge of Brand Approval Processes 27:28 - Less Cooks in the Kitchen Philosophy 28:24 - Closing and Future Plans

This week, we're bringing back this conversation with Cole Walliser as an encore presentation - originally published February 11th, 2025.  Director and Content Creator Cole Walliser (@colewalliser) has captivated millions with his iconic GlamBOT videos and behind-the-scenes glimpses of Hollywood's biggest moments. In today's episode of CREATOR: the Podcast, we explore how this self-taught filmmaker went from making DIY videos in Vancouver to becoming one of entertainment's most influential creators with over 20 million followers across platforms. Cole shares his unconventional path to success, from editing dance reels for $250 to shooting global superstars like P!nk and Katy Perry, and transforming red carpet coverage with his work directing celebrities for GlamBOT. Learn how he built multiple revenue streams through directing, hosting, and brand partnerships, his approach to navigating Hollywood's traditional and digital landscapes, and why he chooses to focus on narrative storytelling despite his social media success. Whether you're an aspiring filmmaker, content creator, or digital entrepreneur, Cole's insights on building a multi-faceted entertainment career, managing brand relationships, and staying true to your creative vision will help you navigate the evolving world of digital content creation and traditional media. To learn more about CREATOR: The Podcast, visit creatorthepodcast.com 0:00 - Introduction to Cole Walliser 1:17 - Cole's Background and Early Career 2:15 - Getting Started with Video at Age 15 3:08 - Moving to LA and Starting Out 4:03 - DIY Filmmaking Approach 5:01 - Early Connections Through Dance Community 6:11 - Big Breaks: Miley Cyrus and Pink 8:14 - The "Fake Out" vs. Real Big Break 10:13 - Working for Free: When It Makes Sense 11:07 - Current Business: Director, Host, and Creator 13:07 - Samsung's "Exposure" Show on Hulu 14:38 - The Glam Bot Story 17:53 - Negotiating Content Rights with E! 20:40 - Favorite Celebrity Glam Bot Moments 22:51 - What Pays the Bills: Brand Partnerships 25:00 - Triple Threat: Director, Talent, and Distribution 26:28 - Moving into Narrative Filmmaking 29:26 - The Process of Making Indie Films 31:21 - Film Festival Strategy 34:02 - Advice on Getting Representation 38:10 - Common Misconceptions About Agents 40:03 - Finding Brand Deals: Spec Work Strategy 42:25 - The Importance of Reels 44:01 - Building Your Team 45:16 - New Business Venture: Coffee Company 48:18 - Memorable Travel Projects 50:13 - Three Country Question: Canada, US, Italy 51:15 - Closing Thoughts

This week, we're bringing back this conversation with Gareth Leonard as an encore presentation - originally published March 18th, 2025.  Travel YouTuber and Content Creator Gareth Leonard (@GarethLeonard) shares his remarkable journey from quitting his job with just $5,000 to becoming a successful travel creator with 700,000+ YouTube subscribers. In today's episode of CREATOR: the Podcast, we explore how Gareth went from living in Argentina as a bartender who "kept getting fired but showing up anyway" to building a thriving multi-channel content business. Ross and Gareth discuss how he started as an "OG travel blogger" in 2009 with the mission to live in Argentina for a year, focusing on genuine cultural immersion rather than country-counting. Gareth reveals his early monetization strategies selling banner ads and text links, his five-year plan living in countries like Colombia, Bolivia, and Guatemala, and his transition from written blogs to video content. Learn about the business side of travel content creation, including YouTube revenue differences across global markets, his multi-channel strategy with his main YouTube channel versus his food YouTube channel Gareth Eats, and how he's repurposing years of archive footage for short-form content. Gareth also discusses the challenges of maintaining authenticity while scaling a travel brand, the financial realities of social media monetization, and why he prefers self-publishing over traditional TV deals. Whether you're an aspiring travel creator or interested in the business of content creation, Gareth's insights on balancing authentic storytelling with strategic growth offer valuable lessons for turning travel passion into a sustainable career. To learn more about CREATOR: The Podcast, visit creatorthepodcast.com 00:00 - Introduction to Gareth Leonard 01:30 - First meeting in Toronto and the beginning of a friendship 03:16 - Origin story: From Tourist to Townie blog in 2009 04:55 - First year in Argentina: Learning Spanish and bartending 07:08 - Building an authentic travel brand through vulnerability 09:53 - Documenting the journey for friends and family back home 11:53 - The difference between Instagram travel and YouTube authenticity 13:17 - Early monetization: From banner ads to tour partnerships 16:12 - The five-year plan: Colombia, Bolivia, Peru, Guatemala, and Brazil 18:57 - The evolution from blogging to video content 20:49 - The Brazil tourism board deal: Filming all 13 World Cup cities 22:58 - Building a YouTube channel to 700,000 subscribers 26:41 - Balancing authentic storytelling vs algorithmic content 28:51 - Creating Gareth Eats: A strategic second channel for consistent revenue 31:08 - YouTube monetization: The benefits of high CPM US-based content 33:18 - Comparing revenue models across platforms: Why YouTube wins 35:40 - Content strategy: Reposting and maximizing your video library 37:57 - The challenges with social media scheduling platforms 39:23 - Current content plan: Day in the Life series and local San Diego food 41:35 - Why major streaming platforms aren't always worth pursuing 44:07 - Passport question: Choosing three countries for life (US, Japan, Portugal) 44:51 - Why Bhutan is Gareth's favorite travel destination