Trail Map Podcast | Podcast on RSS.com

Trail Map Podcast

Trail Map Podcast

by Big Forest LLC

Entrepreneurship Self-Improvement

Season 1

Alan Draper – Kazakhstan, the Art of the Roast, and Starting Over

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 milk craze, and what drives him to keep getting it right — even after starting over. Show notes: 4A Coffee (order online): https://www.4acoffeeroasters.com/ SCA – Specialty Coffee Association (referenced by Alan): sca.coffee

Hunter Marston – Southeast Asia, Think Tanks, and Building a Career in International Affairs

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 life for his family. In this episode, Hunter talks about how living in Vietnam, Thailand, and Myanmar shaped his understanding of the region, why optimism still exists despite rising tensions with China, and what led him to leave DC for Australia. We also get into what it's like to build credibility in foreign policy without following the traditional path, how he balances being a public intellectual with the grounding ritual of trail running, and why slowing down to understand context matters more than reacting to headlines.

Matt Gregory – Operations, Startups, and Learning to Ask Better Questions

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, Patrick flips the table and interviews his co-host about career pivots, the tension between execution and strategy, what it's really like to work at startups during high-growth phases, and why Matt finds more energy in the diagnosis stage than the implementation grind. We also talk about coaching, curiosity, how to build a career that keeps evolving, and why Instagram cooking videos might be the best part of social media.

Mike Hanas – Teaching, Leading Schools, and Learning to Loosen Knots

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. Now, through his consultancy Furthering, Mike helps leaders, teams, and organizations "loosen knots"—creating the conditions for people to have the conversations that matter, even when they're hard. In this conversation, Mike shares how his mother taught him to create space for others, what he learned from Quaker values like truth-seeking and silent reflection, and why holding the tension between our values and our actions is essential. We also talk about why reflection is so rare (and so necessary), and what it takes to help people expect their minds to be changed. Hosted by Matt Gregory and Patrick Dyer Wolf.

Paul Tasner – Starting a Business at 66, Sustainable Packaging, and Pushing Through

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 – Illustration, Authenticity, and Building a Career in Public

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 – Upcycled Cashmere, Career Pivots, and Building a Business from Scratch

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 – Law, Beer, and Victorian Drinking Culture: Following Curiosity Through Life

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.

Penelope Finnie – From Tech and Chocolate to Menstrual Equity: Building Businesses at the Frontier

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.

Rahul Khopkar – Ramen, Roots, and the Realities of Building a Culinary Career

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.

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