When mutual friends in the diabetes community kept telling Rob he had a doppelganger in LA, he figured they were exaggerating. Then he met Dylan Leonard — creative director, documentary filmmaker, college basketball player, type one diabetic, philosophy reader, world traveler — and yeah, the comparisons held up pretty well.
Dylan was diagnosed at 15, having dropped 45 pounds before anyone realized something was wrong. He went from a hospital bed thinking he'd never eat sugar again to playing college basketball while managing T1D without a CGM, without a pump, and without knowing a single other person with diabetes for his first decade. What carried him through was activity — six hours of workouts a day during basketball season — and a mindset he's been intentionally building ever since through reading, travel, and genuinely hard conversations with himself.
This episode goes wide. Rob and Dylan dig into Dylan's upcoming documentary Breaking Limits: Life on the Edge, which follows elite athletes with type one diabetes across seven different sports — from Olympic competitors to IndyCar drivers to American Ninja Warriors. Dylan invested his own money and thousands of hours into this project, not to make a cent, but to hand a 15-year-old sitting in a hospital bed the resource he never had. They also get into the philosophy of travel as the cheapest education on earth, why our brains literally haven't caught up to the abundance of modern life, the difference between manifesting and obsessing, and what a five-hour train conversation with a Norwegian stranger taught Dylan about human connection.
Oh, and they're making plans to run a hoop session next time Rob's in LA. Cameras included.
Chapters:
00:00 Rob's T1D doppelganger, meet Dylan
01:49 Dylan introduces himself: creative, hooper, T1D
02:39 Dylan's diagnosis story: 45 lbs lost at 15
04:36 First pickup game post-diagnosis, flying blind
06:26 How activity literally saved his diabetes management
07:28 Life after college ball: blood sugars out of whack
09:12 Morning routine: walk, no phone, delayed caffeine
10:34 Civilized to Death and the myth of progress
14:48 Our brains weren't built for this level of abundance
17:21 Phones, phones everywhere — even for T1D management
19:45 Abundance mindset, FOMO, and the creative career trap
21:01 Why athletes list it: delayed gratification is a superpower
24:20 Self-help books, repetition, and finding what actually works2
7:48 Manifestation is obsession with action behind it
29:15 Compounding growth: who were we six years ago?
33:14 Breaking Limits documentary: T1D athletes across seven sports
38:59 Nine months of travel: Vietnam, Norway, Australia, Mexico
40:00 "The cheapest education on earth is a one-way flight"
44:44 Japan and what loneliness taught him about human connection
Resources:
Civilized to Death by Christopher Ryan — the book Dylan cites on the myth of perpetual progress and why foraging societies may have been happier than ours
The Game of Life and How to Play It by Florence Scovel Shinn — Dylan's twice-a-year read, ~95 pages, written 100 years ago, still hitting
Risley Health / Rising Above T1D — where Dylan has previously appeared on podcast and debuted early cuts of Breaking Limits (link to Riseley Health podcast)
