This is for all the folks who love to travel, those who travel with others, those craving connection, and those who are the planners in their family and/or friend group! You will be inspired by places to visit and learn about helpful tools to get you there!
Greg joins Dani and Brittany to discuss how connection and honest communication can solve many problems, especially as AI grows and people crave more genuine, flawed human interaction amid concerns such as the “uncanny valley” and AI-generated content. He shares his nontraditional path from studying architecture to earning an MBA, moving to Seattle for tech, and blending creativity with analytical rigor while building the app Your Sojourn. The app helps friends create in-person experiences by notifying contacts about travel, avoiding missed meetups, sharing bucket lists and bookmarks, enabling “open sojourns,” and organizing trips in one place (itineraries, flights, lodging, messaging). Greg recounts extensive travel, mountain-climbing lessons (one step at a time, adapt, refuel, celebrate progress), earning a pilot’s license during COVID, proposing to his wife after re-matching on a dating app, and emphasizing following breadcrumbs with optimism and perseverance.
00:00 Connection Over Everything
00:45 AI Versus Authenticity
04:17 Meet Greg And The Mission
05:31 Gregs Winding Career Path
07:31 Why Sojourn Matters
12:37 Open Sojourns And Planning
19:20 Discover Page And Bookmarks
20:22 Travel Stories Behind The Idea
24:50 New York Safety Storytime
28:32 Using The App For Trips
30:23 Mountaineering Lessons For Work
31:51 Start Before You’re Ready
33:52 Perseverance Mindset Lessons
35:51 COVID Pivot to Pilot License
37:12 The Surprise Proposal Flight
39:15 Meeting Again on Dating Apps
40:37 Sojourn Timing and Iteration
43:01 Optimism and Breadcrumbs
44:09 Career Shift and Big Dreams
47:29 In the Gap Keep Showing Up
50:04 Do the Thing Anyway Story
52:15 Flour Hour Connection Hot Takes
56:15 Follow Your Breadcrumbs Wrap-Up
Download the app on iOS or Android today!
https://www.yoursojourn.com
Follow them on TikTok @your.sojourn & Instagram @yoursojourn
New episodes out every Wednesday!
Watch all videos on YouTube!
Follow us on Instagram, LinkedIn or TikTok!
Where's Waldough? Did you find the hidden loaf? Post and tag us on socials!
Want to be a guest? Fill out our Guest Interest Form!
If you loved what you heard, we would greatly appreciate it if you left us a review. This really helps us out as we get started and helps us know what great content to continue generating for each of you.
In the meantime, go pickup your breadcrumbs!
[All photos were used with permission from Greg Toupalik]