Jon "Boog" Sciambi has been the television voice of the Chicago Cubs since 2021, calling games from the same booth where Harry Caray once sat. He grew up on Roosevelt Island in New York City, played baseball at Regis High School, and found his way to broadcasting after getting cut from the team at Boston College — by walking straight into the campus radio station on day one.

In this episode, Jon (who happens to be Pat's first cousin) talks about play as a professional philosophy — and how channeling a six-year-old's mindset has shaped 30 years in the booth. We get into what it means to call a game for the journey, not just the highlights; how Jon is protecting his love of the craft by being more selective as his career matures; and the story of Project Main Street, the ALS foundation he started after his childhood friend Tim Sheehy was diagnosed in 2005. Jon also tells the story behind the greatest text he's ever received — sent from a Seattle number he almost didn't pick up.

Show notes:

Project Main Street (End ALS): https://projectmainst.org/

End ALS shirts: Obvious Shirts and Ivy Shop: https://obviousshirts.com/products/end-als

John Cleese on Play: https://www.youtube.com/watch?v=r1-3zTMCu4k

Jon's MLB The Show episode on Pablo Torre's show: https://www.youtube.com/watch?v=adoX3IC336o

#TrailMapPodcast #Baseball #ChicagoCubs #SportsBroadcasting #ALS #EndALS #ProjectMainStreet #Podcast #CareerPath #LouGehrigDay #Broadcasting #Storytelling

Amy Devaney is a physical therapist and sports medicine specialist based in Natick, Massachusetts. She's been a PT for over 15 years — starting at Mass General Sports Medicine, then Newton-Wellesley Hospital, and now running her own practice focused on runners and athletes. She got into the field the way a lot of great careers start: with a well-timed accident. A knee injury from skiing on senior skip day her senior year of high school changed her college trajectory, introduced her to physical therapy, and set her on the path she's been on ever since.

In this episode, Amy and the guys get into what it's actually like to build your own PT practice, why she chose to niche down to runners even when it felt risky, what 15 years in sports medicine has taught her about the neuroscience of pain (and why chronic pain is often a brain problem, not just a body one), and why she thinks physical therapy should function as primary care for the movement system. They also get into running as identity, community, and meditation — and how Amy broke her ankle in January and still ran the Boston Marathon in April.

Show notes:

- TempoPT (Amy's Practice): https://tempodpt.com/

- Evlo Fitness (Pat's strength training subscription): http://evlofitness.com

- Oura Ring (wearable HRV/recovery tracker): http://ouraring.com

- Whoop (recovery tracker Matt mentions): http://whoop.com

- Ring Fit Adventure (Pat's son's Nintendo Switch exercise game): https://a.co/d/074RpjKE

- Mind Over Back Pain by John Sarno (Pat's book rec): https://a.co/d/0bRC0g6P

- Elon University (where Amy went to college): http://elon.edu

- Mass General Sports Medicine (where Amy practiced for 7+ years): https://www.massgeneral.org/orthopaedics/sports-medicine

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. It was, as he puts it, a match made in heaven. In this episode, we get into what patents actually are and why we have them, how much creative writing and debate actually go into IP law, why AI is creating new traps for inventors that keep attorneys up at night, and how John thinks very intentionally about allocating his time across work, teaching at Suffolk University, running, and three simultaneous book clubs.

Show notes:

• Lando & Anastasi LLP (John's firm): https://www.lalaw.com/
• Suffolk University (where John teaches business law): suffolk.edu
• The Prestige (film John highly recommends)
• Pachinko by Min Jin Lee (book recommendation) https://www.amazon.com/Audible-Pachinko/dp/B0DJ3G98QT
• Piranesi by Susanna Clarke (book recommendation) https://www.amazon.com/Piranesi/dp/B084NVNFBH
• City of Thieves by David Benioff (book recommendation) https://www.amazon.com/City-Thieves-Novel-David-Benioff/dp/0452295297
• Devil in the White City by Erik Larson (book recommendation) https://www.amazon.com/Devil-White-City-Madness-Changed/dp/0609608444/
• Kaikeyi by Vaishnavi Patel (currently reading) https://www.amazon.com/Kaikeyi-Novel-Vaishnavi-Patel/dp/0759557330/
• The Tao of Physics by Fritjof Capra (referenced by Patrick) https://www.amazon.com/Tao-Physics-Exploration-Parallels-Mysticism/dp/1645472906/

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

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 Honduras washed.

Show notes:

• 4A Coffee (order online): https://www.4acoffeeroasters.com/
• AeroPress (Alan's recommended home brewing method): aeropress.com
• Rainforest Alliance (responsible sourcing certification Alan mentions): rainforest-alliance.org

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 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 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 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.