Trail Map Podcast

Paul Tasner started Pulpworks at 66 after being fired during the financial crisis. Now 80, he's still running the sustainable packaging company alongside his son. We talk about 40 years in supply chain at Clorox and Method, why he gave up climbing the corporate ladder, navigating 540% tariffs, and pushing through loss. A conversation about resilience and reinvention.

Kirk Wallace is an illustrator and founder of BoneHaus. He shares his path from computer science to illustrating for brands like Adobe, Apple, and Google—and his current role as the Boston Celtics' resident artist. We talk about the early Dribbble days, building a career by posting work online, why stepping in front of your work matters, and his hopeful take on the "vinyl swing"—the return to human-made, imperfect art.

Cristina Marcalow is the founder of ANU, a company that upcycles cashmere sweaters into athletic neck warmers. In this episode, Cristina shares her journey from product management in EdTech to launching her own sustainable apparel brand. She talks about losing both parents while becoming a new mom—and how that pushed her to reconsider how she was spending her time. We hear about the friend who cut a sweater into a sports bra in 15 minutes, co-founding ANU as a baby clothes brand, buying out her partner and learning to sew from scratch, and the realities of building a one-woman manufacturing operation. A grounded, inspiring conversation about taking the leap and figuring it out as you go.

Kris Butler is a lawyer, executive coach, award-winning home brewer, and author of Drink Maps: A History of Drinking Establishments in England. In this episode, she shares her journey from practicing adoption law to coaching lawyers at a major firm, her years as a beer judge and home brewing champion, and her deep dive into Victorian-era drinking culture that became a published book. Kris reflects on following curiosity across careers, the distinction between work "for money" and "for fun," and what it takes to commit to a passion project when no one's waiting for you to finish it. A conversation about Renaissance thinking, persistence, and building a life around what genuinely interests you.

In this episode, Matt and Pat talk with entrepreneur Penelope Finnie, CEO of Egal, a company making period pads on a roll. Penny shares her unconventional path from studying art in college to building businesses at the frontier of new industries — from early days at AskJeeves to opening Bittersweet Cafe, a chocolate shop with locations in the Bay Area, to ventures in cannabis and respiratory health during COVID. She reflects on why she's drawn to creating new categories, the creative act of building businesses, balancing ambition with life as a mom and artist, and her current work tackling menstrual equity.

In this episode, Matt and Pat sit down with chef Rahul Khopkar, co-founder of LA’s beloved vegan ramen shop Ramen Hood. Rahul shares how his Korean and Indian upbringing shaped his palate, the winding path that took him from Whole Foods to Napa Valley to working in Copenhagen, and the process behind creating a cult-favorite vegan ramen and yolk. He also talks candidly about the hard truths of the restaurant industry—the physical grind, the psychology of leading a team, and what it takes to keep a small business running in Los Angeles for a decade. A grounded, generous conversation about craft, culture, and resilience in food.

Join Matt Gregory, Patrick Dyer Wolf, and guest Stephanie Hsia as they explore the art and science of designing green spaces, the restorative power of nature in cities, and how a liberal arts, multidisciplinary path can lead to a fulfilling career in landscape architecture.

Nathan Howard is a plasma physicist at MIT working on the future of fusion energy — one of the most promising clean power sources on the planet. In this episode, Nathan shares his journey from childhood curiosity to cutting-edge research, explains how fusion works (and why it’s so hard), and reflects on the role of creativity, collaboration, and turbulence — in both science and life. Plus, we touch on astrophotography, fly fishing, and what keeps him hopeful about the future.

Patrick Dyer Wolf is a songwriter and multi-instrumentalist in the Americana band Goodnight, Texas. In this episode, Patrick talks about what it really takes to build a creative life — from the early days of writing songs in high school to playing the national anthem at a Cubs game. We explore the balance between art and business, staying grounded on tour, and the emotional power of music to reach people when they need it most. Plus, a few wild stories from the road and the origins of his custom songwriting project, The Song Tailor.

John Carter is a strength coach, gym owner, and author who’s spent his life helping people become stronger — inside and out. In this episode, John shares the winding path to opening Titanium Gym and writing Triggered to Change, his new book about taking ownership of your life. We talk about transformation, discipline, failure, and what it really takes to lead — yourself and others — through hard things.