Building Meaningful Connections | Jason Smith (Dad of 2, Klue)

Jason Smith is the Co-Founder and CEO of Klue, an AI-powered competitive intelligence platform. He’s a five-time startup founder, Ernst & Young Entrepreneur of the Year, and a father of two daughters. But his most transformative experience wasn’t raising capital or scaling companies. It was stepping away from it all to travel the world with his wife and kids.When his daughters were just 8 and 9, Jason and his wife quit their jobs, pulled the kids out of school, and spent a full year traveling across 11 countries. We discussed:Leaving work to reconnect: What prompted Jason to walk away from startup life and plan a year-long trip around the world with his wife and two daughters.When things go wrong: Why Jason believes travel disasters make the best family memories and how they used setbacks to teach adaptability and problem-solving.Building deep connections off-grid: How spending 24/7 together changed their family dynamic, from independent dinners to hard conversations.Teaching self-reliance through discomfort: Jason shares his philosophy on preparing kids for the real world and why he sees challenge as essential, not optional.From startup grind to dad mode: The binary approach Jason takes to work and parenting, and why he believes being all-in matters more than balance.How his daughters see him now: Why watching their dad work hard, and then totally disconnect, influenced how his kids think about careers, failure, and ambition.Where to find Jason SmithLinkedIn: https://www.linkedin.com/in/onemoresmith/  Where to find Adam FishmanFishmanAF Newsletter: www.FishmanAFNewsletter.com LinkedIn: https://www.linkedin.com/in/adamjfishman/ Instagram: https://www.instagram.com/startupdadpod/ In this episode, we cover:(00:00) Welcoming Jason Smith, Co-Founder and CEO at Klue(01:09) What sparked a year-long trip around the world(02:21) How planning the journey went from 6 weeks to 12 months(05:08) The wild story of renting their house before quitting their jobs(06:33) Early travel struggles and breakthrough moments(09:54) Teaching kids on the road and bringing learning to life(12:48) Volunteering in Peru and breaking the privilege bubble(17:03) Favorite travel memories and embracing the unexpected(24:51) Why real connection takes getting off the grid(36:17) How his daughters see startups and business now(39:35) Navigating AI and the new rules of work(41:15) Building resilience by leaning into hard things(46:27) United front parenting and avoiding the ‘ask mom, ask dad’ trap(48:26) How the parent-child relationship evolves over 20 years(51:44) Teaching work ethic and financial independence(01:00:49) Lightning round: parenting quirks, movie picks, and minivan takesResources From This Episode:Klue: https://klue.com/ Jason’s Travel Video: https://www.youtube.com/watch?v=O1vMnTDHe6c One More Smith (Jason’s Blog): https://onemoresmith.com/ Jolly Jumper: https://jollyjumper.com/ The Matrix (Film): https://www.imdb.com/title/tt0133093/ Frozen (Film): https://www.imdb.com/title/tt2294629/ Support Startup DadFor sponsorship inquiries, email: [email protected] Startup Dad Merch: www.startupdadshop.com