NextView Partner Stephanie Palmeri sits down with Skyler Erickson, Co-founder of Gondola, for an authentic conversation about building AI for frequent travelers. In this interview, Skyler shares his journey as a second-time founder, from selling his first AI fitness company (Otari) to Peloton in 2020, to now revolutionizing how frequent travelers maximize their points and savings with Gondola. What you’ll learn:

  • How Gondola is building the future of travel with AI that knows you personally
  • Why the $500 billion loyalty points market is ripe for disruption
  • The “magic moments” that make consumer AI products feel transformational
  • Lessons learned from being a second-time founder
  • Why authentic founder-investor relationships matter for long-term success

Key highlights:

  • One Gondola customer saved $2,300 on the same room, same dates
  • Average users have $3,000 in unused loyalty points sitting idle
  • Users earn an average of 16% cash back by stacking rewards through Gondola
  • The platform does loyalty searches across ALL programs in one place

Skyler discusses the “idea maze” of developing Gondola, the importance of deeply understanding your customers (he became a yoga instructor for his first company), and why personalized AI travel experiences represent a generational opportunity. About the speakers: Stephanie Palmeri is a Partner at NextView Ventures, focusing on seed-stage consumer and B2B investments. She’s also a power user of Gondola. Skyler Erickson is co-founder of Gondola, an AI platform for frequent travelers. Previously founded Otari (AI fitness), acquired by Peloton. Learn more: Visit Gondola at gondola.ai.