He turned a love of D&D into $30k bookings. $35 events = 5-figure bkgs. Meet Rocky.

He turned a love of D&D into $30k bookings. $35 events = 5-figure bkgs. Meet Rocky.

Author: Host Agency Reviews July 29, 2025 Duration: 1:56:46

 ****** Transcript, Images + Show Notes: https://har.news/vol33 ******

What happens when you combine a Lord of the Rings obsession, a dragon-themed jeep, and a charismatic entrepreneur? You get Rocky Dimico, the owner of Flights and Fables - one of the most uniquely branded travel agencies we've ever featured! 

Rocky went full-time from day one after a life-changing trip to New Zealand sparked his "aha" moment. But this isn't just another niche story - it's a masterclass in building a brand that people can't ignore. We're talking dragon logos on Jeeps, black tents with gold dragons at vendor events complete with a travel advisor dressed as a wizard, and a business name that came from surveying his Dungeons & Dragons community.

You'll hear how Rocky's gone from zero to hero in just 20 months, selling 6 Lord of the Rings themed trips to New Zealand , expanding into anime/Japan travel, and booking his first groups. His vendor event strategy alone has generated multiple five-figure bookings from $35 investments.

But here's what makes this episode special: Rocky's approach to partnerships, networking, and community building that every entrepreneur can steal. From his Chamber of Commerce connections that led to 4 media articles, to his creative partnerships with map makers and IV therapy businesses, to finding a mentor advisor as his agency grew.

Whether you're looking for inspiration on niche development, want to see what fearless branding looks like, or need ideas for finding clients through in-person events, this episode will knock your socks off.

Plus, stick around to hear about Rocky's big dreams for brick-and-mortar fantasy travel shops in downtown areas across the country and how he successfully found a travel advisor mentor.


Hosted by the team at Host Agency Reviews, this audio channel blends two distinct formats into one practical resource. The first is Travel Agent Chatter, a quarterly series of spotlight interviews that dive deep into the experiences of working travel advisors. These longer conversations explore the real stories behind the careers, covering the nuances of building a business, personal client triumphs, and the cultural insights gained from a life in travel. The companion series, Friday 15, operates on a completely different rhythm. Every week, a focused fifteen-minute episode tackles specific questions from the travel industry, offering direct advice and timely insights that are both concise and immediately useful. Together, this podcast creates a balanced mix of inspirational narrative and actionable strategy. Whether you're seeking motivation from peer journeys or need quick answers to pressing professional questions, the channel is designed to support the daily realities of travel entrepreneurs. It’s a resource that understands the industry's blend of passion and pragmatism, delivered through the authentic voices of those who are deeply embedded in this world. Tune in for thoughtful perspectives that are as varied and dynamic as the travel profession itself.
Author: Language: English Episodes: 100

Travel Agent Chatter | Friday 15
Podcast Episodes
Billing for FIT Trips? How Do Leads Work? [not-audio_url] [/not-audio_url]

Duration: 28:45
Steph and Shayna welcome Sheila Folk of Travel Industry Solutions to cohost the Friday 15 this week! You can check out TIS’s profile here on our brand-new travel tech software profiles.Here are the juicy questions they’l…
Travel with Small Children? How To Organize Digital Info? [not-audio_url] [/not-audio_url]

Duration: 24:23
In episode 199, Steph and Shayna co-host with Jennifer Dugan of Dugan’s Travels! Here’s the questions they’ll tackle this week. Please join us! 1. What is your favorite place to travel with children under 5? ---Staci W.2…
How To Organize Contacts? Should I Go Out On My Own? [not-audio_url] [/not-audio_url]

Duration: 29:58
In episode 198, Steph Lee co-hosts with a longtime friend of the Friday 15, April Swales of Uniglobe Travel Center. They’ve got two especially in-depth questions, so have a look and tune in Friday 12 pm CST! 1. Do you ha…
When to LLC? How To Be a Sub-Agent? Worried About Refunds! [not-audio_url] [/not-audio_url]

Duration: 16:48
In episode 197, Steph Lee hosts and Andavo Travel is our sponsor. (Thanks, Andavo!) Here's a taste of the questions she'll cover! 1. At what point should you LLC (so as to protect your assets), even if your income is not…
System for Supplier Contacts? Go Independent? Thank You Gifts? [not-audio_url] [/not-audio_url]

Duration: 20:13
In episode 196, our very own Mary Stein co-hosts with the one and only Jenn Lee of Vacation Planners! Here’s the questions they’ll tackle this week! 1. Do you have a good system for organizing all your travel BD contacts…
When to LLC? How to Deal with Failure? Which Course To Take? [not-audio_url] [/not-audio_url]

Duration: 20:58
In episode 195, we have a HAR Team special with Shayna Zand and Rita Perez! Here are the questions they’ll cover in this week’s episode! At what point should you LLC (so as to protect your assets), even if your income is…
What CRM for Credit Cards? Too Many Hosts!! How to Assess Fees? [not-audio_url] [/not-audio_url]

Duration: 26:53
In episode 192, Steph cohosts again with Jennifer Dugan of Dugan’s Travels! Here are the questions they’ll cover!1. ​​Hi I’m a new independent travel advisor just getting ramped up and which CRM is recommended for CC pay…