Welcome in. We're really thrilled to have you
joining us today for a brand new deep dive. Yes,
absolutely. It is great to be here. And we have
a very specific mission for this session. We
are going to unpack exactly what it looks like
to build a truly cross -sector career. Right,
which is not easy to do. No, not at all. And
we're doing this by focusing on a single, incredibly
rich Wikipedia article about a man named Robert
L. Gordon III. Yeah, his timeline is just, it's
wild. It really is. So if you're the kind of
person who, you know, loves gaining knowledge,
finding those sudden aha moments and applying
lessons across completely different fields, you're
in the right place. Definitely. Gordon's life
is, well, it's practically a masterclass in taking
skills from one highly structured domain like
the military. Translating them into government,
nonprofits, and eventually even artificial intelligence
and tech. Yeah, and setting the stage for why
this matters to you, the listener, is crucial
here. I mean, we live in a world where people
usually pick a professional lane early on and
just stay in it. Right, you lock it in. Exactly.
You decide you're going to be an academic or
a soldier or a corporate executive. But here,
we are looking at a leader who actively refuses
to stay in one lane. He constantly connects the
dots. across completely different worlds. Which
you just don't see that often. You don't. He
brings the best practices of one sector into
the rigid structures of another. That kind of
adaptability is incredibly rare. And dissecting
the mechanics of how he actually did it? Well...
It offers a blueprint for navigating our own
increasingly complex professional lives. OK,
let's unpack this because we need to start right
at the foundation. Before he was managing millions
of people or working in AI, Gordon had a childhood
that was basically a crash course in reading
the room. Oh, for sure. I was looking at his
early timeline and he moved around constantly.
We are talking about a major geographic spread
across the globe before he even hit college.
Yeah, he grew up as what's colloquially known
in the armed forces as a militant. Right. Which
means he was the child of an active duty service
member, leading to a deeply nomadic early life.
He was born in Richmond, Virginia in 1957. His
father was an American Army officer and his mother
was a school teacher. So they were always on
the move. Exactly. Because of his father's deployments,
he spent a major chunk of his youth overseas.
He lived in the Tianmu District in Taipei, Taiwan,
attending the Dominican International School
right in downtown Taipei. Wow. And then later,
the family was off to Germany, living in Frankfurt
and Augsburg, where he went to the Augsburg American
High School. Over his childhood, he also lived
in New York, Virginia, and Colorado, finally
graduating in 1975 from a high school in Colorado
Springs. I mean, just think about that for a
second. If you are a kid constantly moving from
Taiwan to Germany to Colorado, you are forced
to learn how to adapt to new cultures almost
overnight. You have no choice. Right. It's sort
of like being an undercover spy in middle school.
You have to figure out the local slang, the social
hierarchy, the unwritten rules of every single
new cafeteria you walk into. What's fascinating
here is how this global nomadic upbringing perfectly
tees up. his future ability to navigate vastly
different institutional cultures. Oh, that makes
total sense. When you're a child dropped into
Taipei and then later Augsburg, you develop a
highly tuned sense of observation. You learn
that different environments communicate differently.
Later in life, when Gordon is transitioning from
the rigid, top -down hierarchy of the Pentagon
to the consensus -driven environment of a nonprofit,
he's utilizing those exact same adaptive muscles
he built as a kid. And he takes that adaptability
straight into a highly structured environment
first, right? West Point. Yes, the United States
Military Academy. He enters in 1975, graduates
in 1979, and gets commissioned as a second lieutenant
in the field artillery. And he really hits the
ground running. He goes to ranger school, holds
numerous artillery assignments. But there is
a standout detail from his early military arc
that caught my eye. What was that? From 1981
to 1982, he is selected to be the aide -de -camp
to then Brigadier General Colin Powell. So for
anyone not steeped in military terminology, what
does an aide -de -camp actually do? It's essentially
serving as the executive assistant and right
-hand person to a general officer. You manage
their schedule, ensure they have the briefing
materials they need, and act as a gatekeeper.
That sounds like a lot of pressure for a young
officer. Immense pressure. But being an aid to
camp to a rising star like Colin Powell is an
incredible vantage point. It's a daily apprenticeship
in high -level leadership, crisis management,
and strategic decision -making. You get to be
in the room where the biggest calls are made.
And that exposure clearly pays off because his
artillery career just keeps accelerating. He
becomes the distinguished graduate at the Field
Artillery Advanced Course at Fort Sill and later
commands a heavy artillery company in Bamberg,
Germany. Right. He's doing the grueling on the
ground work. He is clearly thriving as a practitioner
out in the field doing the heavy lifting. But
then he makes a pivot that feels a bit unusual
for a hard charging artillery commander. Yeah,
we start to see a crucial pattern emerge here.
A lot of highly successful officers at that stage
would just stay in the field, continuing on that
standard command track to chase their own general
stars. Exactly. But Gordon steps out of the pure
practitioner role and embraces the academic side.
He goes to the Princeton School of Public and
International Affairs, earning a master's in
public affairs in 1989. Then he returns to West
Point, but this time to teach. Going back to
where it all started. Right. He joins the Department
of Social Sciences, serving as an instructor,
an assistant professor of American politics,
and eventually the director of American politics
for the department. Which is a great lesson for
anyone listening. Don't just do the work, figure
out how to teach the work to the person behind
you. That's how you truly master a subject. Absolutely.
He is literally teaching the theory of American
government while actively serving in its military
apparatus. I really want to emphasize to you
listening right now how rare and valuable it
is to cultivate both of these profiles. Being
able to command a heavy artillery company requires
a very specific type of authoritative, decisive
leadership. You give an order and it happens.
No debate. Exactly. No debate. But teaching American
politics at West Point requires intellectual
humility, theoretical understanding, and the
ability to foster debate among incredibly bright
cadets. Gordon, building both the doer and the
teacher mindsets, is the secret sauce for his
later cross -sector success. Which brings us
to his first massive leap outside the military
bubble. In 1992, Gordon wins the highly prestigious
White House Fellowship. He serves as the director
of special operations for the Office of National
Service. And while he's there, he actually helps
to found the AmeriCorps program. That is a massive
pivot. It's huge. We're talking about a career
army officer building a civilian national service
organization from the ground up. He's taking
his deep understanding of military service, the
commitment, the logistics, the deployment of
personnel, and translating it into a civilian
framework. He also spent time working as a special
assistant to three different secretaries of Veterans
Affairs. Now, navigating the VA during changes
in presidential administrations is famously chaotic.
I can only imagine. It requires immense bureaucratic
agility to keep massive, complex programs running
while political appointees are shuffling in and
out. He learned how to keep the machine working
regardless of the politics. My absolute favorite
part of this era is how he physically bridges
his two worlds back at West Point. While he's
there teaching, he co -founds and spends six
years as the executive director of a privately
funded program called Service America. Right.
I love this initiative. He took West Point cadets,
future military officers, and paired them up
with civilian AmeriCorps members. They teamed
up to build low -income housing, improve environmental
awareness, and work as tutors. in cities all
over the country. We're talking Seattle, Chicago,
Austin. If we connect this to the bigger picture,
Gordon is actively trying to solve the civilian
-military divide. The military is a very isolated
subculture. A shrinking percentage of the American
public has any direct personal connection to
it. By pairing cadets with AmeriCorps volunteers,
Gordon isn't just getting houses built. He's
taking the ethos of military service. the discipline,
the commitment to a cause greater than oneself,
and blending it with civilian community building.
Forcing them to work together. Exactly. He's
forcing future generals and future civilian leaders
to sweat together to understand how the other
side thinks and operates. It seems like that
experience gave him the nonprofit bug. In 2006,
he makes a massive move to the nonprofit sector
full time. He joined City Year, which is a huge
national service program focused on education.
He becomes their senior vice president of civic
leadership and chief people and program officer.
He created their Give a Year program, too. Yes.
But this is where I have to pause and ask the
obvious question. How does an artillery commander
convince a massive youth education nonprofit
that he is the right guy to run their HR and
program development? Culturally, those feel like
opposite ends of the universe. On the surface,
they look completely different. But look at the
mechanics of the job. As chief people and program
officer, Gordon was responsible for the recruitment,
training, and deployment of a 3D 500 -person
youth corps. That is a lot of people. A lot of
young people. These are 17 to 24 year olds working
full time as tutors and mentors. In the military,
Gordon learned that you don't scale an organization
by just giving orders. You scale by building
a standardized, repeatable training pipeline.
Oh, wow. The military has perfected the art of
taking thousands of 18 year olds from different
backgrounds, giving them a shared culture and
deploying them to achieve a complex mission.
Gordon took that exact military doctrine. and
applied it to civilian teenagers that is brilliant
instead of training them to operate artillery
he trained them to run after school programs
The mission changes. But the logistics of human
deployment remain exactly the same. That makes
the transition make so much more sense. He isn't
changing his skill set. He's just changing the
target. And he clearly masters that civilian
scale because it sets the stage for the climax
of his government service. In July 2010, Gordon
is appointed by President Barack Obama as the
Deputy Undersecretary of Defense for Military,
Community and Family Policy. Just saying the
title takes a deep breath. It really does. But
the title barely captures the staggering reality
of the job. I was reading the statistics on this
and the numbers are dizzying. Can you break down
the actual scale of what he was managing at the
Pentagon? Gladly. Gordon was responsible for
defense -wide policy and global community support
programs designed to care for 2 million service
members, 1 .2 million military spouses, and 2
million children. That is unbelievable. There's
over 5 million people worldwide under his direct
purview. It's the logistical equivalent of being
the mayor, the school superintendent, and the
chief wellness officer for a mid -sized country,
except your citizens are scattered across the
entire globe. Let's look at just a few of the
specific initiatives because it helps ground
those massive numbers. First, education. He oversaw
DODA, which is the Department of Defense School
System. At the time, that meant managing 90 ,000
students in 194 schools. Across multiple continents.
Yes. These schools aren't just in one state.
They're in 12 foreign countries, seven U .S.
states, Guam and Puerto Rico. On top of that,
he led the effort to overhaul the infrastructure
of 160 public schools located directly on military
installations across the United States. The logistics
of global education management are mind boggling.
You're dealing with different legal jurisdictions,
international treaties, and the emotional stress
of kids whose parents might be deployed in combat
zones. And it doesn't stop at schools. He spearheaded
the Military Spouse Employment Partnership. This
initiative partnered with over 400 employers
nationwide, and it resulted in over 120 ,000
military spouses being hired. Which is life -changing
for those families. Completely. He also managed
defense resale for over 500 commissaries and
exchanges. For the listener who might not know,
a commissary is essentially a massive... tax
-free grocery and retail store on a military
base. So he's effectively running a global retail
chain on the side. Plus, he was responsible for
voluntary education for half a million active
duty members, child development programs, two
armed forces retirement homes, and even casualty
and mortuary affairs, including military funeral
honors. It is vital to step back and look at
why these specific programs matter deeply to
the military. Taking care of spouses, ensuring
military children have good schools, providing
career advancement for families. These aren't
just administrative tasks or corporate HR perks.
No, not at all. This is a core component of national
security. If a soldier is deployed overseas and
they're worried about their child's school failing
or their spouse not being able to find a job
because they had to move across the country again,
that soldier is distracted. They are less effective
in their mission. You can't focus on the mission
if your family is struggling. Precisely. By elevating
family policy, Gordon was directly contributing
to military readiness. He understood the fundamental
truth of the modern armed forces. You don't just
deploy a soldier. You deploy a family. Treating
human infrastructure with the exact same strategic
weight as physical infrastructure. That is a
brilliant way to frame it. And his work at the
Pentagon was highly recognized. He was awarded
the Secretary of Defense Medal for Outstanding
Public Service. A huge honor. Adding to a massive
list of honors he collected over his career,
including the Legion of Merit and being a French
-American Foundation Young Leader. You'd think
after managing the well -being of 5 million people,
he might just retire to a quiet life. But we
still have an entirely new sector to explore.
The pattern of aggressive cross -pollination
just continues. Before he fully leaves the government
sphere, he serves as the founding chair of Service
Nation. Mission Serve, working alongside his
fellow Princeton grad Ross Cohen to build nationwide
partnerships integrating veterans back into their
communities. That was a major initiative, right?
It was so major that it was inaugurated by First
Lady Michelle Obama and Dr. Jill Biden on Veterans
Day 2009. Okay, here's where it gets really interesting.
After all of this, the artillery commands, teaching
at West Point, building AmeriCorps, running HR
for City Year, and managing the entire family
policy apparatus for the Pentagon Gordon pivots
straight into high tech. It's a fascinating leap.
He becomes the chief strategy officer at Upskill,
which is a smart glasses software company based
out of Virginia. And today, he is currently serving
as the senior strategic leader for AI and digital
innovation at Document Storage Systems, Inc.,
or DSS. This raises an important question, doesn't
it? How does a career field arterium and Pentagon
policy chief transition into enterprise smart
glasses and artificial intelligence? On paper,
those sound like completely different universes.
Seriously, how does he do this? I get stressed
just managing my own calendar, let alone jumping
into the AI sector with no traditional computer
science background. It goes back. to the underlying
mechanics of his entire career. Tech companies,
especially those dealing with enterprise software,
AI integration in healthcare systems, often have
brilliant engineers. They know how to write the
code. What they frequently lack are people who
truly understand systemic implementation at a
massive national scale. Let's look at his current
role at DSS, a company that specializes in health
information technology, particularly for the
Department of Veterans Affairs. AI integration
in a massive hospital network isn't just a coding
problem. It is a change management problem. I
see where you're going with this. You have to
convince doctors, nurses, and administrators
to change their daily habits and trust a new
system. You have to understand bureaucracy, training
pipelines, and human psychology. So tech companies
are bringing him in not to build the AI, but
to figure out how to successfully deploy the
AI into massive human systems. Precisely. Whether
you're managing 3 to 500 city -year core members,
overseeing 500 military commissaries, or figuring
out the go -to -market strategy for enterprise
smart classes, you are dealing with complex human
systems. You have to understand strategy, leadership,
and how to align a massive organization toward
a single, unified goal. he's the translator yes
Gordon brings that strategic operational vision.
He translates the brilliant ideas of the engineers
into a language that a massive bureaucracy can
actually absorb and implement. So what does this
all mean for you listening to this right now,
whether you are prepping for a big strategic
meeting, trying to figure out your next career
move, or just trying to navigate a professional
world that feels increasingly fragmented? Gordon's
life proves a massive point. You do not have
to choose just one path. You really don't. The
skills you learn in one domain can be your absolute
superpower in another. If you learn how to build
a training pipeline in the military, you can
use that to teach teenagers in a nonprofit. If
you learn how to manage the bureaucracy of 160
global schools, you can use that to implement
AI in a national healthcare system. The adaptability
to learn new systems and the drive to connect
different types of people is the ultimate career
hack. I want to leave you with a final thought
to mull over. Our modern educational and corporate
systems are hyper -focused on specialization.
From a very early age, we're pushed to pick one
lane, declare a major, specialize our resumes,
and stay safely within our chosen industry. But
when you look at the massive systemic impact
of a cross -sector life like Robert Gordon's,
it begs the question, how much world -changing
innovation are we leaving on the table by not
encouraging more people to aggressively cross
-pollinate between the military, civilian nonprofit,
and tech worlds?