Trail Map Podcast

John Spangenberger is a patent attorney at Lando & Anastasi in Boston — and he got there entirely by accident. A kid who loved creative writing, peaked in fifth grade with a trophy for a story about warring grocery store vegetables, discovered physics in high school, studied electrical engineering at RPI, and found out patent law existed through a friend of a friend his senior year of college....

Trail Mix is our bonus episode format — shorter, more experiential. In this first one, Matt heads to 4A Coffee Roasters in Newton, MA for a morning with founder Alan Draper to learn the roasting process firsthand. Alan walks through an entire roast of the Silk Route blend — from charging the drum to first crack to the cooling tray — then sets up a side-by-side cupping of an Ethiopian natural and a...

Alan Draper founded 4A Coffee in Almaty, Kazakhstan in 2004, shipping a roaster and espresso machines across the world before specialty coffee was a known concept there. After nine years and three kids, he brought it home to Brookline. In this episode, we talk about Alan's path building 4A from scratch in Central Asia, the craft and precision behind roasting, surviving the Yelp era and alternative...

Hunter Marston taught English in Vietnam after college, got hooked on Southeast Asia, and eventually turned that curiosity into a career as a foreign policy analyst. Based in Washington DC for years, he's now moving to Australia to take on a new role—continuing his work writing for major foreign policy publications and advising governments on US-China competition while building a different kind of...

Matt Gregory has spent 20 years building things—from baby food to respiratory health devices to at-home hair removal. He's worked as an operator, a strategist, and now a consultant helping early-stage companies navigate the messy realities of product development and scale. Along the way, he's learned that the questions you ask matter more than the answers you think you have. In this episode, Patri...

Mike Hanas spent 40 years in education—teaching Latin, Greek, and ancient history, and serving nearly 20 years as a head of school at Carolina Friends School and San Francisco Friends School. He's the person schools called when things got hard: navigating conflict, addressing historical abuse, facilitating difficult conversations, and building communities grounded in truth-seeking and integrity. N...

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 huma...

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...

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 reflect...

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 healt...

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...

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 touc...

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...

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...