Episode 70: Saying Yes to the Right Invitations with Colin Stroud

ON ADVENTURE PODCAST  |  EPISODE 70 Episode 70: Saying Yes to the Right Invitations with Colin Stroud                                Episode Description What if your next great adventure is not a destination at all, but a willingness to say yes to the breadcrumbs life keeps dropping in front of you? Colin Stroud is a 26-year-old credit card rewards consultant, founder of Go Somewhere, and one of the fastest growing voices on LinkedIn in the points and miles space. He grew up in Fort Wayne, Indiana, the son of an OB/GYN and a nurse midwife who met delivering a baby together, and he was on track for a more traditional path until a six-week Spanish immersion trip to Oviedo at 16 cracked the world wide open. From there it was Italy on a $380 flight, a Catholic mission to Poland, an unlikely run at Ave Maria University in south Florida, an early marriage and a baby on the way before he had even graduated, and a first job in life insurance case design that he knew almost immediately was not it. What followed is a story about paying attention. A coworker mentioned the Chase Trifecta. A LinkedIn post about points went viral and got picked up by The Washington Post. A side hustle turned into consulting calls, then into a community for business owners, then into a full-time business helping families and entrepreneurs unlock travel they thought they could not afford. We talk about why early travel rewires you, what it actually takes to leave a steady paycheck, the difference between dopamine and meaning, why family life and entrepreneurship feel like the truest adventures of his life right now, and the surprising decision he and his wife made after almost moving to Hawaii. Colin makes a strong case that the go somewhere life is not always about getting on a plane, and that learning to be rooted where your feet are can be its own kind of expedition.   Episode Highlights 00:00  From cheap flights as a teenager to a full-time business helping people unlock travel 06:00  World Youth Day in Poland, six weeks of Spanish immersion in Oviedo, and catching the travel bug 14:00  Marriage, a baby on the way, and a first job in life insurance that did not fit 18:00  Discovering the Chase Trifecta and stepping into the points world 23:00  The first viral LinkedIn post and a Washington Post quote that changed everything 25:00  Quitting in November 2024 and going full-time on Go Somewhere 30:00  Almost moving to Hawaii, pumping the brakes, and rethinking what travel does for young kids 34:00  Why family life and entrepreneurship are the truest adventures of his life right now 39:00  Measuring yourself: finally finding feedback after years of feeling stuck 47:00  The two ingredients behind a viable internet business: clear writing and consistent humility 55:00 What adventure means now and where to find Colin online   Connect with Colin Stroud LinkedIn: linkedin.com/in/colinstroud Website: gosomewhere.world Newsletter: The Go Somewhere Newsletter at gosomewhere.world Email: [email protected]   Connect with the On Adventure Podcast Hosted by Josh Self, financial advisor and everyday explorer. Subscribe on YouTube, Spotify, Apple Podcasts, and all major streaming platforms Follow on Instagram for short-form clips and behind-the-scenes content Connect on Facebook: On Adventure Podcast with Josh Self Connect on LinkedIn: Josh Self Subscribe to the Patreon for more content! If this episode resonated with you, leave a review and share it with someone who needs to hear it