Before They Were Experts They Made It Up | Danielle Strachman and Kevin Leahy on Creating Your Path

A venture investor and an audio storyteller explore curiosity, community, and unconventional careers. Danielle Strachman (1517 Fund, Teal Fellowship) and Kevin Leahy (Podcast Point Man, NPR alum) join Matt to dig into education outside the system, how local projects build connection and opportunity, and why following your instincts matters more than following a script. This episode is about taking risks, creating your own lanes, and building things that last.Main topics coveredDanielle’s journey from Craigslist tutor to running the Teal Fellowship and 1517 FundEarly lessons building a tutoring business and charter school from scratchWhy college isn’t the only path and how alternative education unlocks talentKevin’s path from NPR journalism to podcast building and business strategyThe power of curiosity, naivete, and learning by doingWhy local podcasts and grassroots community building matterROI vs the long tail of serendipity and relationshipsCreativity, risk taking, and finding meaning through work and peopleYouTube timestamps00:00 Introductions04:00 Danielle’s path: tutoring, homeschooling, charter school09:30 Teal Fellowship and backing young founders13:00 Skills based hiring and education reform18:00 Kevin’s path: reporting, NPR, learning media24:00 Curiosity, creativity, and making your own path28:00 Local podcasts, community, and connection33:00 ROI vs serendipity in community building37:00 Alternative education and real world learning47:00 Following instincts, shipping work, taking risks58:00 Closing thoughts and lessons