Welcome to today's deep dive. If you've ever
looked at your own career path and felt like,
you know, you're being forced to pick just a
single lane. Right. Like you have to choose between
the corporate world or public sector or tech.
Exactly. Today's subject is going to completely
challenge that premise for you. We are looking
at a single, honestly, incredibly dense Wikipedia
article today. It's about a man named Robert
L. Gordon III. And the mission for this deep
dive is to explore what it means to be a true
cross sector leader. Yeah. And for anyone listening
who is trying to figure out how to pivot in their
own career, Gordon's life is pretty much the
ultimate masterclass in adapting. I mean, across
the military, government, nonprofits and even
the high tech world. It really is. Because on
paper, it might seem disjointed at first glance.
Well, yeah. Resumes often look like a random
list of jobs. Yeah. But when you really look
at Gordon's career, it reveals a fascinating,
deliberate pattern of scaling human impact. It's
not random at all. Right. So to understand how
he built that, we need to go back to the beginning,
the foundation of what you might call a scholar
soldier. He was born on March 15th, 1957. In
Richmond, Virginia. Richmond, Virginia, yes.
To an army officer father and a schoolteacher
mother. So right away, you have this mix of military
structure and education. And because of his dad,
he lived the classic military brat life. Constantly
moving. Constantly. I mean, we're talking Taiwan,
where he attended the Dominican International
School, Germany, going to the Augsburg American
High School. Plus stints in New York, Virginia,
Colorado. What's fascinating here is how that
nomadic global childhood, living in places like
the Tianmu District in Taipei, for example, build
a foundation of extreme adaptability. Yeah. For
you as a listener, think about applying that
to your own life. Being the new kid constantly,
learning new cultures, new rules. You have to
learn how to read a room instantly. You literally
have no choice, which probably served him incredibly
well when he hit his formal military and academic
rigor. So he goes to West Point. graduating in
1979 with a Bachelor of Science, gets commissioned
as a second lieutenant in the field artillery
and goes through ranger school, which we know
is designed to just absolutely break you down
physically and mentally. It's brutal, yeah. But
he pushes through. And then... Early in his career,
he hits two massive milestones. First, from 1981
to 1982, he serves as an aide -de -camp to then
Brigadier General Colin Powell. Which is huge.
Huge, being a fly on the wall with someone like
Colin Powell. And then later, he earns a Master
of Arts in Public Affairs from Princeton. This
is where we see the dual nature of his career
really take shape. He wasn't just in the field,
you know, commanding a heavy artillery company
in Bamberg, Germany. Right. Though he did do
that. But he was also an intellectual. He actually
returned to West Point to teach in the Department
of Social Sciences. Yeah, he eventually became
the director of American politics there. Exactly.
He's teaching the political frameworks that govern
the very military he serves in. Okay, let's unpack
this. Because this blend of operational command
and political theory leads to his massive footprint
in civilian national service. The pivot to nonprofits.
Yeah, this is a major turning point. In 1992,
he becomes a White House fellow. He serves as
the director of special operations for the Office
of National Service. And while there, he actually
helps found AmeriCorps. He was instrumental in
that. And what's wild is that he didn't just
build policy in Washington. While he was at West
Point, he co -founded a program called Service
America. Right, bringing the two worlds together.
Literally combining West Point cadets with AmeriCorps
members. He ran it for six years. They went into
six different cities to tutor, build low -income
housing, and improve environmental awareness.
If we connect this to the bigger picture, you
have to look at why this matters for you, the
listener. Gordon didn't just participate in service.
He built the infrastructure for others to serve.
He recognized that military cadets and civilian
activists speak totally different languages.
But by putting them on a housing project together,
they had to build empathy. Empathy through shared
struggle. And he took that system building directly
to City Year in 2006. Yeah, as the Senior VP
of Civic Leadership and Chief People and Program
Officer. Overseeing 3 ,500 youth corps members,
he created the Give a Year program, which is
now the City Year Alumni University Partners.
His expertise was in such high demand that he
even traveled to Italy in 1997 to help reform
their national service system. Wow, I didn't
realize it was international. Oh, yeah. And he
worked with an American Jewish Committee task
force in 2006, recommending a U .S. national
service strategy. He was the architect. Which
sets up his return to the Pentagon. And the scale
here is just staggering. In 2010, President Barack
Obama appoints him as the deputy undersecretary
of defense for military community and family
policy. The scope of responsibility in that role
is almost hard to wrap your head around. Let
me just list the numbers for you. He was overseeing
2 million service members, 1 .2 million spouses,
2 million children, over 2 million military families
worldwide. He's basically managing the civic
infrastructure of a small country. Exactly. Including
the school system. He oversaw the DODA, the Department
of Defense Education Activity. That's $90 ,000
finance. 194 schools. 14 districts spread across
12 foreign countries, seven states, Guam, and
Puerto Rico. And he didn't just maintain it.
He overhauled the infrastructure of 160 public
schools on military installations. Yes. And on
top of that, he spearheaded the Military Spouse
Employment Partnership. Which was so necessary.
Military spouses face huge economic penalties
because of constant relocation. Employers wouldn't
hire them because they knew they'd move. So Gordon
brings together 400 employer partners. to create
portable careers, resulting in over 120 ,000
military spouses getting hired. That's real tangible
impact. It's no wonder he was awarded the Secretary
of Defense Medal for outstanding public service
for this. He approached defense not just as weapons
or tactics, but as human community resilience.
Caring for the families behind the soldiers.
Precisely. You fortify the family, you strengthen
the military's operational readiness. And he
kept working on that civilian -military gap after
the Pentagon. He became the founding chair of
Service Nation, Mission Serve. Which has now
got your six under the Bob Woodruff Foundation.
Right. Working with Army vet Ross Cohen. Gordon
created over 30 partnerships that were actually
inaugurated by First Lady Michelle Obama and
Dr. Jill Biden on Veterans Day in 2009. Again,
building infrastructure to help veterans reintegrate
into their civilian communities. But here's where
it gets really interesting. You'd think after
the Pentagon, he'd just retire or join a think
tank. Right. Take it easy. But no, he makes a
massive pivot into the high -tech frontier. The
AI and digital innovation space. Exactly. He
becomes the chief strategy officer of Upskill,
which is a smart glasses software company, then
chief global officer of Connected Living. And
currently, he serves as senior strategic leader
for AI and digital innovation at Document Storage
Systems, Inc. It seems like a sharp left turn,
right? How does a retired Army colonel and national
service advocate end up leading AI strategy?
It sounds totally disconnected. But it's not.
It's perfectly aligned. By being a lifelong learner
who focuses on how tools and policies empower
people. That's the core lesson for the listener
here. Oh, I see. Technology is just the new tool.
Exactly. Whether it's AmeriCorps volunteers or
AI at the VA, he's building systems to support
human beings. That's why he's also an advisor
to startups like UniteUS and Warrior Centric
Health. So the core mission never changed, just
the leverage she was using. Precisely. That is
such a powerful takeaway for you as you think
about your own path. Robert L. Gordon III's life,
which, by the way, is decorated with honors like
the Legion of Merit, the Franklin Award, and
Princeton's Edward P. Bullard Distinguished Alumnus
Award, it proves you don't have to pick just
one lane. You really don't. You can master the
military, government, nonprofits, and tech as
long as your core mission remains consistent.
And this raises an important question, a final
thought for you to chew on today. Yeah. Based
on Gordon's life work of merging civilian and
military populations, like when he combined those
West Point cadets with AmeriCorps volunteers,
what would happen to our society's current political
and cultural divides if a unified mandatory national
service program were implemented today? Oh, wow.
Would the empathy generated by working alongside
people from entirely different backgrounds solve
the modern crisis of connection? It's something
to think about. It really is. Shared struggle
might just be the adhesive we're missing. Well,
we want to thank you so much for joining us on
this deep dive today. We hope this masterclass
in adaptability gives you some inspiration for
your own career pivots. Keep exploring, keep
learning, and we'll see you next time.