The Link

Sage Advice: Donald on Wilderness, Music, Buddhism & More

Meredith, Farah, Diana and Dave welcome guest Donald Sage (also Milton Academy class of ’86), who lives with his wife Ellie in Fort Bragg on California’s Mendocino coast. Donald recounts meeting Ellie at a Deadhead concert, describes their quiet life amid redwoods and ocean winds, and shares his early life: growing up on a Montana cattle ranch, his mother Hope’s brain tumor and death by suicide when he was nearly nine, and being taken in by the Bancroft family in Medfield, Massachusetts. He discusses studying environmental conservation at the University of Colorado Boulder, therapy, Buddhism, meditation, and a semester in Kathmandu, plus later meditation communities and a pilgrimage to Buddhist sites in India. Donald reflects on music—from Milton orchestra and jazz to playing jam/jazz-rock-blues in clubs—plus parenting two grown children. The group reminisces about Milton baseball trips to Florida, considers attending the May reunion, and ends with Donald’s kindness-focused reflection and a brief meditation bell exercise.
 
Topics
00:51 Mood Check Roundtable
02:04 Introducing Donald C
03:05 Life on Mendocino Coast
04:51 How We Met Ellie
06:56 Montana Roots and Loss
10:12 New Family in Medfield
11:43 Boulder Healing and Buddhism
12:37 Milton Orchestra Triangle Story
16:00 Drumming and Band Days
18:04 Retired Trust Fund Life
18:52 Kids and Clean Energy
19:42 Meditation and Nepal Tease
20:13 Nepal To India Journey
21:13 Bitterroot Ranch Life
22:06 Organic Farming Values
22:50 Family Updates And Pets
24:08 Baseball Florida Memories
26:08 Reunion Plans And Yearbooks
28:50 Mill Valley Reflections
29:56 Kindness And Meditation Practice
33:22 Advice To Younger Self
35:07 Bell Breathing And Farewell

From Netflix to TKO, Dean Garfield For The Win

Farah, Meredith, Diana and Dave welcome classmate Dean Garfield, reflecting on high school in the 1980s and reconnecting after decades. They introduce Dean’s public-policy career, including senior roles at Netflix as VP of Public Policy, industry associations, and advisory appointments under Presidents Obama and Trump, and discuss his new role as SVP of Government Affairs at TKO (WWE, UFC, On Location, and IMG). Dean answers ’80s rapid-fire questions (movies, music, Milton classes, library hangouts, dress code, snacks), then shares his immigration story from Jamaica, early experiences in Boston during busing, how Milton became a supportive breakthrough for his family, and how sports helped him acclimate. He describes living abroad in Amsterdam and Singapore, returning to New York and Martha’s Vineyard, his daughters’ education and careers, his Netflix priorities (local-for-local global content, live sports including women’s sports, and theatrical windows), why he left Netflix, his interest in Saudi Arabia’s social transition, and how AI may reshape culture and business.
 
Topics
00:43 Meet The Hosts And Guest
01:57 Dean Garfield Career Highlights
03:48 Eighties Rapid Fire Quiz
06:05 Milton Memories And Snacks
11:45 From Jamaica To Boston
13:09 Finding Milton And Mentors
17:28 Sports And Staying Connected
19:05 Life Today Family And Travel
21:51 Career Through Line Begins
23:11 Chasing High Performance
24:22 Curiosity Across Cultures
24:59 Reconnecting After Decades
26:10 Netflix Influence Playbook
27:05 Local for Local Explained
28:03 Sports and Theatrical Bets
30:23 Why He Left Netflix
32:20 Choosing the Next Role
34:11 Inside TKO and WWE UFC
37:18 Geopolitics and AI Focus
40:30 Golden Age of Television
44:56 Advice to Younger Self
49:21 Farewell and Where to Connect

Jen Stromsten: Loving Vermont

Meredith, Diana, Farah and Dave catch up with Jen Stromsten (attended Milton for two years, entering as a junior). Jen shares her path from Brown to a UMass Amherst master’s in regional planning, and her current work as Director of Programs at Brattleboro Development Credit Corporation (BDCC), an economic development nonprofit in southern Vermont. She describes working “boots on the ground” on workforce initiatives like a “reality fair” for Vermont high schoolers, grant-funded economic development, housing as a long-running planning focus, and efforts to reverse demographic decline through rural refugee resettlement—accelerated by arrivals after Afghanistan. Jen discusses living in Greenfield, Massachusetts, her husband Dave’s career as a historian of technology and curator, and how Milton’s peer culture and supportive administrators shaped her. She reflects on local problem-solving, antigovernment capacity constraints in rural areas, and wanting nonprofits to solve problems strongly enough to make themselves obsolete.
 
Topics
01:01 Hosts Catch Up
01:56 Oat Creamer Rant
02:37 Meet Jen Stromsten
04:01 Milton Memories
06:10 Roots and Instability
08:51 Marriage and Career Path
10:41 Grad School Pivot
12:38 Housing and Planning
13:40 Vermont Yankee Closure
15:19 Boots on Ground Work
17:31 Refugee Resettlement
19:41 Kids and Family Life
20:37 Love Story Timeline
22:23 Where Are You Now
22:32 Country Life and Commuting
23:13 Museum Trips and Bletchley Park
24:06 Rural Policy and Government Capacity
26:51 Milton Influence and Peer Culture
29:25 Mentors and Hyatt Dinner Story
32:33 Local Action and Energy Policy
36:36 Nonprofit Innovation Mindset
39:30 Advice to Milton Self
42:56 Housing Advocacy and Vermont Impact
45:59 Wrap Up and Where to Find Jen

Michael Gitlitz: The Art of ‘Chickie’

Diana, Farah, Meredith and Dave crack open the time capsule and pull out classmate Michael Gitlitz—art dealer, museum director, and living proof that those Milton art history classes weren’t just a GPA play.
Michael takes us from dorm-room décor (read: questionable) to a globe-trotting, 25-year run in the high-end art world—Herschel & Adler, Marlborough Gallery, Paddle8—before landing as executive director of the Katonah Museum of Art. Now “retired” (sure, Michael), he’s still wheeling, dealing, collecting, and casually dropping knowledge on 17th–20th century art like it’s fantasy baseball stats.
Along the way: – The exact moment Milton lit the art-history fuse – Why art dealers matter (and why academia might not scratch the same itch) – A return to the ‘80s that includes fashion crimes and social survival tactics – Teachers who mattered, crushes that didn’t, and the masks we all wore – And a refreshingly real look ahead to the 40th reunion—less posing, more honesty, and finally talking about mental health without whispering it like it’s contraband
It’s part nostalgia, part career masterclass, part group therapy—with better stories and worse outfits.
Time Codes (because we’re professionals… allegedly): 00:00 Welcome Back to The Link 01:33 Meet Michael Gitlitz (yes, that one) 04:05 How a Milton kid ends up in the global art game 05:29 Back to the Eighties Quiz (brace yourself) 09:56 Style Regrets: A Group Confession 14:47 The Milton Spark That Started It All 15:56 Gap Year = Life Upgrade 18:05 Why Art Dealers Actually Matter 19:53 Family Stories You Didn’t Expect 20:43 Art Dealing: How the Sausage Is Made 22:08 Classmates in the Arts (you’ll be surprised) 23:04 Milton Needs a Museum (seriously) 24:53 The Cost of Collecting (spoiler: not cheap) 26:14 Favorite Living Artist 27:12 Retirement… kinda 29:09 Teachers Who Changed Everything 34:53 Reunion Talk + Mental Health (finally, honestly) 37:22 Crushes, Masks, and Surviving High School 39:00 Rules, Discipline, and Sanctuary 42:45 Life After the Art World (is there such a thing?) 43:45 Advice to Our Younger, Dumber Selves 46:30 Wrap Up (we stuck the landing)

The Fabulous Nicole Holt on Narcolepsy, Seattle Island Life & Finding Your Way Back

The guest is Nicole Holt, now living on an island near Seattle. The show opens with 1980s rapid-fire memories (Talking Heads and Pink Floyd on a Walkman, shoulder pads, and hanging out in the “butt room”). Nicole shares that she has narcolepsy, describing how it affected her at Milton, the long path to diagnosis, and extreme REM onset confirmed by EEG, plus safety strategies like pulling over when driving and even briefly falling asleep while swimming laps. She recounts leaving Bennington on medical leave and later learning a parent withdrew her while claiming she failed out, as well as studying political philosophy at William & Mary as an unclassified student. Nicole discusses making horse-themed art, maintaining a studio, leasing and riding a highly trained horse, limited contact with Milton classmates, plans to attend reunion, and her child’s transition, estrangement, and later progress including unionizing at work.
 
Topics
00:42 Meet The Hosts
01:29 Introducing Nicole Holt
02:52 Walkman And Music
04:32 Favorite Classes
06:20 Campus Style And Hangouts
06:50 Butt Room Memories
09:00 Life In Seattle Island
09:28 Andrew And The Move
12:45 Careers And Law School Era
14:33 Narcolepsy Explained
19:36 Bennington And Withdrawal
21:52 Art And Studio Plans
23:51 Keeping In Touch
23:54 Missing Kristen Henley
25:30 10 Acre Memories
26:30 Quilling and Sleepovers
27:01 Reunion and Hermiting
27:58 Pandemic Parenting Saga
31:25 Art Research Adventures
33:57 Bennington Drama Stories
35:09 Milton Plays Throwback
36:17 Advice to Younger Self
39:31 Horses Again as Adult
40:36 Teeth Troubles and Dreams
42:11 Goodbyes and Wrap Up

Sylvia (Castillo) Slack on Milton, Counseling, and Aikido Life in Oregon

Hosts of The Link—Milton Academy Class of 1986—welcome guest Sylvia Slack (formerly Sylvia Castillo) from outside Portland, Oregon, joined by her dog Keto. After an ’80s-themed “Dare to Be True” icebreaker, Sylvia shares what she loved about Milton: the people, being away from home, and feeling accepted. She explains being recruited from San Antonio through A Better Chance, receiving scholarship travel, and choosing Williams College, where she majored in psychology inspired by Mrs. Griffin. Sylvia describes a 20-year career in Communities in Schools counseling at-risk students and later training staff, retiring in 2010 when moving to Oregon. She and her retired deputy U.S. marshal husband maintain a wooded acreage, build ongoing projects, and hunt deer and elk. She discusses Aikido’s conflict-resolution philosophy, travel through a dojo network, and reflects that time goes fast and should be fully appreciated.
 
Topics
01:31 Meet Sylvia and Keto
03:08 Dare to Be True 
07:40 Milton Memories and Favorites
10:02 Life in Oregon Woods
14:39 Deck Projects and Visitors
16:34 How Sylvia Found Milton
19:06 Choosing Door Number Two
21:09 Family of Eight Support
22:09 Williams and Psychology Path
23:36 Counseling At Risk Students
25:15 From Counselor to Trainer
27:33 Retiring to Portland Life
28:24 Aikido Philosophy and Practice
33:03 Reunions and Big Question
35:24 Advice to Younger Self
37:03 Reconnect and Farewell

Hangin’ With Mr. Cooper

The Link wraps up Season 2 with a great visit with Derrick Cooper. Hear about his life as a pharmacist - and a grandpa! Coops also recalls his Milton role models and tells the tale of why he did a handstand during a wrestling weigh-in.

Caitlin’s Adventures in the Arts

Caitlin Bermingham has been working at the Whitney Museum of Art for the past 14 years in preparations and exhibitions. She is currently the head preparator, dealing with logistics and packing of exhibitions that go all over the world.Learn about her career in art, her own work and her stint as a bass player in the punk rock band Cheesecake!Please support this podcast on Patreon at https://www.patreon.com/thelinkpodcastEmail producer Dave with feedback: david@pod617.comGet your own podcast at www.pod617.com/contact

Going Deep With Mik Aoki

Mik Aoki was a standout baseball player at Milton Academy, but who knew he was on the way to a lifetime in baseball? Hear his tales as a college baseball coach and memories of MA.Please support this podcast on Patreon at https://www.patreon.com/thelinkpodcastEmail producer Dave with feedback: david@pod617.comGet your own podcast at www.pod617.com/contact

John Marshall’s Plan

John Marshall is a professor at the Georgia State College of Law where his expertise is private, nonprofit and government interventions to promote long-term urban recovery from crisis and disasters.But he's still good old "Marsh" and he joins the show to talk about both his current studies and remembrances from MA.Get in touch with John here: https://law.gsu.edu/profile/john-travis-marshall/Please support this podcast on Patreon at https://www.patreon.com/thelinkpodcastEmail producer Dave with feedback: david@pod617.comGet your own podcast at www.pod617.com/contact