My guest today is Jon Bailey; a travel and lifestyle blogger, vacation dreamer and planner as well as the owner of i.d.e.a., an integrated marketing agency focused on helping brands find their courage. He is Father to two teen girls and husband to one outstanding man and has combined his talents and passions for travel and writing to build

2 Dads With Baggage focuses on family travel, LGBT, lifestyle, and parenting, and features travel stories and tips from around the world, as well as the everyday adventures of two gay dads raising two teen tempests.

In the intro to the podcast, I also share a recent trip to Huatulco, Mexico. This is a relatively unknown Mexican beach town (unless you are from Canada). I share the best ways to find great airfare, our hotels, tours and favorite things about Huatulco.

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Show Intro: Visiting Huatulco, Mexico with Volaris Airlines

For Spring Break, my son Roland and I headed to Huatulco, Mexico. We flew on Volaris Airlines from Tijuana using the CBX border crossing. We stayed at three hotels; a budget hotel: Marina Hotel, a boutique hotel: Villa Blanco and an all-inclusive: Las Brisas. I worked with Paraiso Tours for a city tour, boat & snorkel tour and an ATV tour. Head to the podcast to hear about all of our adventures in Huatulco and the amazing airfare available on Volaris!

How to Pitch Brands, Destinations & PR with Jon Bailey of 2 Dads With Baggage

Listen to today’s episode to hear how Jon built the brand of 2DadsWithBaggage in such a short time. We also chat about how to approach building your blog in a very business minded way as well as tips for monetizing, ambassadorships, and building revenue streamsThis is “How to Pitch Brands, Destinations & PR with Jon Bailey”.

Full episode >> listen to today’s episode

jon bailey 2 travel dads blogger

Listener Questions: How to Pitch Brands, Destinations & PR

Jon Bailey is also the owner of i.d.e.a, a marketing agency based in San Diego that helps brands grow and increase their visibility.  This combined with being a successful travel writer and blogger, offers him a really unique point of view.

He sees pitches coming into i.d.e.a from bloggers and journalists who want to work with the brands he represents and he has also been on the other side, pitching brands.

So, before my interview with Jon, I reached out to the Aspiring Travel Writer community to see what questions they had about pitching PR. Thank you to everyone who shared their questions! Make sure to listen to today’s episode for his answers! 

Questions from Amy from a A Traveling Broad 

  1. How much info does a PR person want a blogger pitching them to provide?
  2. What is reasonable for a blogger to ask for in terms of compensation when they are new to working with PR reps/brands?
  3. What kind of research should a blogger do about a company/brand before crafting their pitch?

Question from Nina from

  1. She’d like to know How long do you spend reading a pitch? I’m assuming she means you as a PR person.
  2. Where should the hook go and what is the part of a pitch that really hooks you?
  3. Do you prefer formulaic or abstract pitches?

Questions from travel writer’s academy member Rina LA Family

  1. What do PR companies value the most in return for a hosted opportunity and how should we present the value we would give them if they worked with us in our first email?
  2. Also, do they research the writer that approaches them and how?
  3. Also, what’s the best way to connect with PR to get on their FAM trips list or get on their radar?

Question from Crystal from

  1. What are your best tips for pitching when you don’t have a huge audience, but are passionate about the brand/destination and know you could do a great job of promoting it? 

Question from Lian Dolan from Satellite Sisters

  1. I’m wondering about average response times to media requests. I pitched a PR person representing a destination spa two weeks ago and have not heard back. I have both a podcast segment and a print piece in lifestyle magazine locked in.
  2. For the magazine piece, I really need to know so I can move on if the PR team isn’t interested. Should I resend pitch? Move on? Go directly to the media relations department at the destination?

Question from Jen from 

  1. Why do so many brands/PR ghost influencers after expressing interest in working with them, even discussing the scope of work? I’ve had this happen so many times and my follow-ups just go ignored. 
  2. I have a F/U to Jen’s question, which is I have had the experience of working with PR and many times, they don’t respond after you deliver. Before, during and after a trip or project, I’ll get email after email, and then once I deliver, a percentage will never respond or give feedback. Have they just moved on to the next project?

Question from Robin Dohrn -Simpson of

  1. How does your blogging enhance your PR work and vice versa?

Top Takeaways from the Podcast with Jon Bailey:

  • Follow up after a conference or event is key.  
  • Why you must build relationships with PR and tourism and think about the long term.
  • It’s not about taking every trip you are offered.
  • Why you must know your niche as well as the initiatives of a destination to determine if ‘now’ is the right time to visit or pitch your visit.
  • Why you must know if your perspective and your audience fit the goals for the brand or destination?
  • Why it boils down to authenticity when working with a brand.
  • Why your feelings shouldn’t be hurt if you aren’t invited on every trip you apply for.
  • Jon’s top takeaways from the 2019 Travel Academy Mastermind.
  • The importance of finding a tribe and meet in person as bloggers.
  • How Jon has approached building his blog as a business.
  • The right approach to build your brand and get your name out there.
  • Why you should think about your blog as a business from the beginning.
  • Why you must be able to know what you offer your readers and the benefits they get from your blog.
  • Why you must know why a brand should work with you.
  • Why approaching your blog as a personal scrapbook isn’t useful to travelers.
  • Why content has to be useful.
  • Why you should add brands you’ve worked with to your homepage.
  • Don’t be shy to ask for references or comments from brands you’ve worked with.
  • Why Jon doesn’t add prices to his media kit.
  • Why you should let your pitch sit in your drafts for 24 hours before sending.
  • How to find a Brand or Destinations previous blogger campaigns.
  • How PR companies research travel writers and bloggers.
  • Why it’s our responsibility to deliver results to the destinations and brands we work with.

Full episode >> Listen to Episode 142 Now!

Episode Resources

New York Travel Show
Travel Writer’s Academy

Connect with Jon Bailey
Jon Bailey on Instagram
Jon Bailey on Facebook
Jon Bailey on Twitter
Jon Bailey on Instagram

Connect with Alexa, Break Into Travel Writing & My Travel Blog

The Aspiring Travel Writer, the Facebook group


  • Loved this episode about Pitching Brands, Destinations & PR with Jon Bailey of @2DadswithBaggage  on the @writetotravel podcast! [CLICK TO TWEET]

Hope you enjoyed this episode and are inspired to think about how you can set goals for your blog in 2019! Interested in hearing the full podcast? Click here to listen now!

Feedback on the Podcast If you have any suggestions for upcoming shows or a question for an upcoming episode, leave a comment below. If you enjoyed this podcast, I’d be extremely grateful if you would take a second and leave me a review and rating over on iTunes. Taking a minute to do this allows me to help more people with this podcast, so I really appreciate it (once on that page, simply click on the “View in iTunes” button to leave your review — thanks very much!)

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How to Pitch Brands, Destinations & PR with Jon Bailey


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