Episode 2: Beyond the Boardroom – Erik Blachford on Adventure, Change, and Resilience

In this episode, I sit down with Erik Blachford—early Expedia founder and CEO, board member, advisor and investor to talk about navigating change, taking risks, and getting outside your comfort zone.

Erik shares stories from the early days of building Expedia, his passion for building ventures and outdoor adventures, and his passion for helping leaders and the moment he got a quiet nudge to make a pivot in his career that changed everything. 

One of my favorite takeaways? “Have all the plans you want—but know they’re written in sand. Don’t get upset when the tide comes in.”

If you’re in a season of uncertainty, this conversation is a reminder to stay curious, stay connected, and be patient with the process, especially in difficult times.

Erik Blachford has led companies through M&A, sat on public and venture-backed boards like Zillow, Peloton, Hipcamp and Glassdoor, and invested in startups across travel, marketplaces, and consumer tech and helps leaders, early-stage founders, think through go-to-market, scale, and staying focused under pressure.

Get tools to guide your next chapter: Subscribe to Anne's Choose Adventure Letter for book launch updates and free downloadable resources from All Who Wander.

Keep the Conversation Going

We’d love to hear how this podcast episode inspired you. Share your favorite quotes, moments of clarity, or what you’re choosing next. Use the hashtag #AllWhoWanderPodcast #ChooseAdventure and tag @hiptravelmama on social media so we can celebrate your journey with you. Here’s to choosing adventure together!

The book is here! 🎉 In this special episode of All Who Wander, journalist Kavita Varma White interviews Anne to share the story behind the book launch of All Who Wander: A Guide for Finding Your Path in Seasons of Change and what it really means to choose adventure, especially when life feels uncertain. 

Whether you’re starting out, starting over, or somewhere in the messy middle, this is your invitation to choose adventure over fear. 

🎧 Listen now wherever you get your podcasts.
📖 Grab your copy of All Who Wander on Amazon or Barnes & Noble online.

#AllWhoWanderBook #ChooseAdventure #PodcastLaunch #NewEpisode

Get tools to guide your next chapter: Subscribe to Anne's Choose Adventure Letter for book launch updates and free downloadable resources from All Who Wander.

Keep the Conversation Going

We’d love to hear how this podcast episode inspired you. Share your favorite quotes, moments of clarity, or what you’re choosing next. Use the hashtag #AllWhoWanderPodcast #ChooseAdventure and tag @hiptravelmama on social media so we can celebrate your journey with you. Here’s to choosing adventure together!

Four-time Emmy® Award-winning host Mickela Mallozzi, creator of Bare Feet with Mickela Mallozzi shares how dancing with locals around the world became a powerful way to build community, celebrate culture, and connect across borders. Season 7 of her PBS series premiered on May 1, 2025, and continues to explore the beauty of diversity, the importance of equity, and the power of inclusion through dance . You won’t want to miss this inspiring conversation.

Get tools to guide your next chapter: Subscribe to Anne's Choose Adventure Letter for book launch updates and free downloadable resources from All Who Wander.

Keep the Conversation Going

We’d love to hear how this podcast episode inspired you. Share your favorite quotes, moments of clarity, or what you’re choosing next. Use the hashtag #AllWhoWanderPodcast #ChooseAdventure and tag @hiptravelmama on social media so we can celebrate your journey with you. Here’s to choosing adventure together!

Follow @reidontravel

Robert Reid on LinkedIn

In this episode #36, Robert shares insightful stories from his extensive travel career, including quirky adventures like counting mustaches in Russia and playing the clarinet in St. Lucia. The discussion dives deep into the evolution of his career, his unexpected return to Oklahoma to support family, and the how his is natural curiosity and calculated risks have led him to incredible destinations and a sense of place around the world.  Robert also reflects on the lessons learned about navigating career transitions, maintaining work-life balance, and importance of pursuing creative projects. The conversation emphasizes the value of passion, the joy of travel as play, and the importance of staying open to new ideas and experiences.

02:29 Robert's Current Day Job and Life in Portland

03:45 Journey Through Robert's Career

06:56 Transition to Video and National Geographic

08:16 Return to Oklahoma and PBS Role

11:33 Navigating Career and Personal Life

16:29 Taking Calculated Risks

20:18 The Challenges of Being a Travel Writer

21:55 The Importance of Shared Experiences

22:41 Robert's Advice to His Younger Self

23:31 The Mustache Ticker Experiment

24:34 Travel as Play and Creativity

28:53 One of Robert's Favorite Travel Moments

Get tools to guide your next chapter: Subscribe to Anne's Choose Adventure Letter for book launch updates and free downloadable resources from All Who Wander.

Keep the Conversation Going

We’d love to hear how this podcast episode inspired you. Share your favorite quotes, moments of clarity, or what you’re choosing next. Use the hashtag #AllWhoWanderPodcast #ChooseAdventure and tag @hiptravelmama on social media so we can celebrate your journey with you. Here’s to choosing adventure together!

Jacqueline Tanzella talks about her launch into freelance work as a brand marketer and her journey to living as an expat in Paris and Tuscany today. She shares the importance of female friendships, listening to our instincts, knowing when we are off balance, and following the "shiny things" that bring us light and joy. 

Links: Jacqueline Tanzella on LinkedIn.

Pastry chef, workshops and corporate retreats. ATE THREE

@Jacqattack on Instagram.

Get tools to guide your next chapter: Subscribe to Anne's Choose Adventure Letter for book launch updates and free downloadable resources from All Who Wander.

Keep the Conversation Going

We’d love to hear how this podcast episode inspired you. Share your favorite quotes, moments of clarity, or what you’re choosing next. Use the hashtag #AllWhoWanderPodcast #ChooseAdventure and tag @hiptravelmama on social media so we can celebrate your journey with you. Here’s to choosing adventure together!

Krista shares her extensive career journey, from her early days as an Internet travel analyst, to her current role supporting travel tech startups and as an advisor at Boston Venture Studio. We talk about the importance of starting any new venture is to understand what problem you are solving, the important of having a team with a shared vision, and how the pandemic changed her perspective on travel and being rooted in one place and importance of her work friendships, and community on Martha's Vineyard.

Find Krista on LinkedIn

@Kpappas on Instagram

Get tools to guide your next chapter: Subscribe to Anne's Choose Adventure Letter for book launch updates and free downloadable resources from All Who Wander.

Keep the Conversation Going

We’d love to hear how this podcast episode inspired you. Share your favorite quotes, moments of clarity, or what you’re choosing next. Use the hashtag #AllWhoWanderPodcast #ChooseAdventure and tag @hiptravelmama on social media so we can celebrate your journey with you. Here’s to choosing adventure together!

Anne throws it back to a conversation with Dan Fine, her first boss! Hear how Dan navigated his way as an AD Man, to Internet trailblazer, to entrepreneur, and now retired, philanthropist and documentary producer, and the lessons he has learned along the way. 

Links:

Dan Fine on LinkedIn

UWARF.org

War Tails Documentary Film link coming soon. Read about the recent screening it in the Edmonds Times

Get tools to guide your next chapter: Subscribe to Anne's Choose Adventure Letter for book launch updates and free downloadable resources from All Who Wander.

Keep the Conversation Going

We’d love to hear how this podcast episode inspired you. Share your favorite quotes, moments of clarity, or what you’re choosing next. Use the hashtag #AllWhoWanderPodcast #ChooseAdventure and tag @hiptravelmama on social media so we can celebrate your journey with you. Here’s to choosing adventure together!

In this episode Anne talks with Megan Cunningham, the CEO and founder of Magnet Media, a New York City-based creative studio.  Megan is an author, producer, director, and media executive and has worked at PBS, HBO, and MTV. Anne and Megan talk about the important role storytelling plays in creating a more empathetic and just world, she believes in the power of building a strong community, the challenges and joys of juggling entrepreneurship and family, and why exercise and sleep are important tools in her self-care toolkit. Cunningham emphasizes the importance of developing a diverse network of women from different backgrounds and the value of reaching out to connect during periods of change, loneliness, and transition and a recent family trip to Japan and what she loved about that trip.

Shortcuts:

04:39 Megan's Journey: from film to entrepreneurship

08:48 The role of creativity and community in personal growth

12:16 Megan's entrepreneurial journey 

17:31 Balancing work, family, and self care

22:57 The Importance of community and connection

26:37 Travel Stories: Her recent trip to Japan with her family

Links: 

https://www.linkedin.com/in/megancunningham/

https://www.magnetmediafilms.com

Get tools to guide your next chapter: Subscribe to Anne's Choose Adventure Letter for book launch updates and free downloadable resources from All Who Wander.

Keep the Conversation Going

We’d love to hear how this podcast episode inspired you. Share your favorite quotes, moments of clarity, or what you’re choosing next. Use the hashtag #AllWhoWanderPodcast #ChooseAdventure and tag @hiptravelmama on social media so we can celebrate your journey with you. Here’s to choosing adventure together!