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 covered
Danielle’s journey from Craigslist tutor to running the Teal Fellowship and 1517 Fund
Early lessons building a tutoring business and charter school from scratch
Why college isn’t the only path and how alternative education unlocks talent
Kevin’s path from NPR journalism to podcast building and business strategy
The power of curiosity, naivete, and learning by doing
Why local podcasts and grassroots community building matter
ROI vs the long tail of serendipity and relationships
Creativity, risk taking, and finding meaning through work and people
YouTube timestamps
00:00 Introductions
04:00 Danielle’s path: tutoring, homeschooling, charter school
09:30 Teal Fellowship and backing young founders
13:00 Skills based hiring and education reform
18:00 Kevin’s path: reporting, NPR, learning media
24:00 Curiosity, creativity, and making your own path
28:00 Local podcasts, community, and connection
33:00 ROI vs serendipity in community building
37:00 Alternative education and real world learning
47:00 Following instincts, shipping work, taking risks
58:00 Closing thoughts and lessons