Emma Hayward is a 30-year-old sailor who splits her time between an Antarctic research vessel, Rhode Island, and living on a boat that she fixed up. (@emmastoryhayward)

Growing up on Cape Cod with parents who worked on boats, Emma never wanted an office job or predictable life—which is why she keeps building a life at sea, even as her friends settle down and start families.

Emma describes her journey from a “schooner bum” to a dirtbag rich captain and boat owner who works 3-4 months/year to cover her costs and accumulate savings. Crucial to this journey was securing a position on a 300-foot Antarctic research vessel, where she launches scientific gear as part of climate-related projects.

How do people make money with boats? Emma walks us through the options, from crewing fancy yachts (lucrative but not so purposeful) to charter day-trips (lucrative and somewhat purposeful) to outdoor education on tall ships (very purposeful but horribly paid). She touches on power and gender dynamics at sea, dealing with boredom and monotony, and the challenge of maintaining friendships and romantic partnership when spending so much time away.

Emma also tells the story of her gap year (and a half) when she sailed from Hawaii to San Diego with her dad, as well as a recent voyage from Rhode Island to Ireland that ended with a week of dodging container ships amid thick fog.

Full transcript: dirtbagrich.com/emma

Tim and Angel Mathis are married nurses and lapsed Christians who enjoy hiking, running, and traveling very long distances. Tim is the author of The Dirtbag's Guide to Life (timmathiswrites.com) and Angel teaches investment skills to fellow nurses (learn.nursesinvesting.com).

Tim begins by sharing his feelings about me stealing the term "dirtbag rich"—which he coined in his 2019 book—and transforming it into a larger concept that emphasizes purposeful work.

Tim finds his own purpose as a mental health nurse and book writer. He tells the story of losing his dad in the middle of a Pacific Crest Trail hike, the period of hedonistic dirtbag drifting that followed, and how he went from evangelical Christian, to Episcopal minister, to fully leaving the faith. He describes how ultrarunning and thru-hiking offered a quasi-religious new community, sense of belonging, and positive emotions. "Nature is my spirituality now," Tim says—and this is a "deeply American thing."

We then hear from Angel—the financial brain in the marriage—who shares the story of getting laughed at by a financial advisor early in their careers. The couple ended up doing everything the advisor didn't think possible: buying a house, getting graduate degrees, making work optional after age 35, and traveling 3-6 months each year.

Angel's sense of financial security comes from taking a hard look at the numbers each month, using the same method that she teaches to other nurses. As a nurse practitioner, she enjoys helping many patients in a short amount of time—just as long as she's working part-time. Raised Catholic and later baptized Protestant, Angel laughs about enjoying a diversified spiritual portfolio, even as nature-oriented rituals have replaced the religious ones (e.g., long runs on Sundays instead of church). She reflects on how easy it was to build new friendships in their thirties through long-term traveling hiking, where low time pressure allows deep relationships to blossom.

Find Tim and Angel on Instagram: @dirtbagguide / @nursesinvestingforwealth

Full transcript: dirtbagrich.com/timangel

Justin Riley is a 40-year-old dance teacher, wilderness junkie, and organizer of alternative-culture partner dance events. (justindance.com)

Justin has spent nearly two decades designing events that blur the line between art, dance, and wilderness immersion. His festivals are more than just places to dance—they’re cultural experiments that challenge people to step outside their comfort zones and co-create something meaningful. Whether it’s a week-long floating dance party on Utah’s Green River or a countryside retreat in Spain, Justin’s spaces are deliberately messy and wildly participatory. (He’s also responsible for helping me fall in love with fusion dance in 2016.)

We discuss Justin’s early years as a dirtbag wanderer living on $5,000 a year while chasing dreams as a photojournalist and political activist and the joy he finds in solving life’s problems without money. Today he earns money through a combination of event organizing, dance teaching, and converting buses and vans. When work feels so much like play, Justin observes, “I feel like my whole life is filled with free time.”

Justin explains his "high risk, low consequence" design philosophy, his commitment to wilderness exploration (a vital counterbalance to his hyper-social work), and his belief that meaningful experiences don’t come from perfection but from trust, collaboration, mutual joy, and the willingness to let things break—and then building something new together.

Find Justin’s next events at unboundfusion.com.

Full transcript: dirtbagrich.com/justin