WEBVTT 00:00:00.000 --> 00:00:03.040 Welcome to today's deep dive. If you've ever 00:00:03.040 --> 00:00:05.160 looked at your own career path and felt like, 00:00:05.219 --> 00:00:07.299 you know, you're being forced to pick just a 00:00:07.299 --> 00:00:09.460 single lane. Right. Like you have to choose between 00:00:09.460 --> 00:00:11.740 the corporate world or public sector or tech. 00:00:12.140 --> 00:00:14.839 Exactly. Today's subject is going to completely 00:00:14.839 --> 00:00:17.500 challenge that premise for you. We are looking 00:00:17.500 --> 00:00:20.379 at a single, honestly, incredibly dense Wikipedia 00:00:20.379 --> 00:00:23.399 article today. It's about a man named Robert 00:00:23.399 --> 00:00:27.420 L. Gordon III. And the mission for this deep 00:00:27.420 --> 00:00:30.620 dive is to explore what it means to be a true 00:00:30.620 --> 00:00:33.780 cross sector leader. Yeah. And for anyone listening 00:00:33.780 --> 00:00:35.619 who is trying to figure out how to pivot in their 00:00:35.619 --> 00:00:38.520 own career, Gordon's life is pretty much the 00:00:38.520 --> 00:00:41.380 ultimate masterclass in adapting. I mean, across 00:00:41.380 --> 00:00:43.939 the military, government, nonprofits and even 00:00:43.939 --> 00:00:46.399 the high tech world. It really is. Because on 00:00:46.399 --> 00:00:49.039 paper, it might seem disjointed at first glance. 00:00:49.320 --> 00:00:51.359 Well, yeah. Resumes often look like a random 00:00:51.359 --> 00:00:53.539 list of jobs. Yeah. But when you really look 00:00:53.539 --> 00:00:55.679 at Gordon's career, it reveals a fascinating, 00:00:55.859 --> 00:00:59.020 deliberate pattern of scaling human impact. It's 00:00:59.020 --> 00:01:01.259 not random at all. Right. So to understand how 00:01:01.259 --> 00:01:03.000 he built that, we need to go back to the beginning, 00:01:03.079 --> 00:01:05.719 the foundation of what you might call a scholar 00:01:05.719 --> 00:01:09.620 soldier. He was born on March 15th, 1957. In 00:01:09.620 --> 00:01:11.120 Richmond, Virginia. Richmond, Virginia, yes. 00:01:11.340 --> 00:01:13.739 To an army officer father and a schoolteacher 00:01:13.739 --> 00:01:16.519 mother. So right away, you have this mix of military 00:01:16.519 --> 00:01:19.939 structure and education. And because of his dad, 00:01:20.219 --> 00:01:23.280 he lived the classic military brat life. Constantly 00:01:23.280 --> 00:01:25.760 moving. Constantly. I mean, we're talking Taiwan, 00:01:25.900 --> 00:01:27.640 where he attended the Dominican International 00:01:27.640 --> 00:01:31.540 School, Germany, going to the Augsburg American 00:01:31.540 --> 00:01:35.069 High School. Plus stints in New York, Virginia, 00:01:35.209 --> 00:01:37.590 Colorado. What's fascinating here is how that 00:01:37.590 --> 00:01:40.829 nomadic global childhood, living in places like 00:01:40.829 --> 00:01:43.849 the Tianmu District in Taipei, for example, build 00:01:43.849 --> 00:01:46.670 a foundation of extreme adaptability. Yeah. For 00:01:46.670 --> 00:01:48.790 you as a listener, think about applying that 00:01:48.790 --> 00:01:51.010 to your own life. Being the new kid constantly, 00:01:51.209 --> 00:01:53.549 learning new cultures, new rules. You have to 00:01:53.549 --> 00:01:55.329 learn how to read a room instantly. You literally 00:01:55.329 --> 00:01:57.469 have no choice, which probably served him incredibly 00:01:57.469 --> 00:01:59.689 well when he hit his formal military and academic 00:01:59.689 --> 00:02:02.519 rigor. So he goes to West Point. graduating in 00:02:02.519 --> 00:02:05.500 1979 with a Bachelor of Science, gets commissioned 00:02:05.500 --> 00:02:07.939 as a second lieutenant in the field artillery 00:02:07.939 --> 00:02:11.240 and goes through ranger school, which we know 00:02:11.240 --> 00:02:13.419 is designed to just absolutely break you down 00:02:13.419 --> 00:02:15.159 physically and mentally. It's brutal, yeah. But 00:02:15.159 --> 00:02:18.030 he pushes through. And then... Early in his career, 00:02:18.189 --> 00:02:22.270 he hits two massive milestones. First, from 1981 00:02:22.270 --> 00:02:25.750 to 1982, he serves as an aide -de -camp to then 00:02:25.750 --> 00:02:28.430 Brigadier General Colin Powell. Which is huge. 00:02:28.629 --> 00:02:30.750 Huge, being a fly on the wall with someone like 00:02:30.750 --> 00:02:33.110 Colin Powell. And then later, he earns a Master 00:02:33.110 --> 00:02:35.330 of Arts in Public Affairs from Princeton. This 00:02:35.330 --> 00:02:37.789 is where we see the dual nature of his career 00:02:37.789 --> 00:02:40.889 really take shape. He wasn't just in the field, 00:02:40.969 --> 00:02:43.449 you know, commanding a heavy artillery company 00:02:43.449 --> 00:02:45.449 in Bamberg, Germany. Right. Though he did do 00:02:45.449 --> 00:02:47.840 that. But he was also an intellectual. He actually 00:02:47.840 --> 00:02:50.000 returned to West Point to teach in the Department 00:02:50.000 --> 00:02:52.319 of Social Sciences. Yeah, he eventually became 00:02:52.319 --> 00:02:54.500 the director of American politics there. Exactly. 00:02:54.500 --> 00:02:56.800 He's teaching the political frameworks that govern 00:02:56.800 --> 00:02:59.199 the very military he serves in. Okay, let's unpack 00:02:59.199 --> 00:03:02.060 this. Because this blend of operational command 00:03:02.060 --> 00:03:05.539 and political theory leads to his massive footprint 00:03:05.539 --> 00:03:09.759 in civilian national service. The pivot to nonprofits. 00:03:10.639 --> 00:03:13.159 Yeah, this is a major turning point. In 1992, 00:03:13.460 --> 00:03:15.840 he becomes a White House fellow. He serves as 00:03:15.840 --> 00:03:17.819 the director of special operations for the Office 00:03:17.819 --> 00:03:20.979 of National Service. And while there, he actually 00:03:20.979 --> 00:03:23.819 helps found AmeriCorps. He was instrumental in 00:03:23.819 --> 00:03:25.620 that. And what's wild is that he didn't just 00:03:25.620 --> 00:03:28.379 build policy in Washington. While he was at West 00:03:28.379 --> 00:03:30.879 Point, he co -founded a program called Service 00:03:30.879 --> 00:03:33.280 America. Right, bringing the two worlds together. 00:03:33.620 --> 00:03:36.439 Literally combining West Point cadets with AmeriCorps 00:03:36.439 --> 00:03:39.439 members. He ran it for six years. They went into 00:03:39.439 --> 00:03:42.620 six different cities to tutor, build low -income 00:03:42.620 --> 00:03:44.900 housing, and improve environmental awareness. 00:03:45.219 --> 00:03:47.400 If we connect this to the bigger picture, you 00:03:47.400 --> 00:03:49.599 have to look at why this matters for you, the 00:03:49.599 --> 00:03:52.300 listener. Gordon didn't just participate in service. 00:03:52.639 --> 00:03:55.500 He built the infrastructure for others to serve. 00:03:55.659 --> 00:03:58.419 He recognized that military cadets and civilian 00:03:58.419 --> 00:04:00.719 activists speak totally different languages. 00:04:01.060 --> 00:04:03.560 But by putting them on a housing project together, 00:04:03.740 --> 00:04:06.960 they had to build empathy. Empathy through shared 00:04:06.960 --> 00:04:10.199 struggle. And he took that system building directly 00:04:10.199 --> 00:04:13.479 to City Year in 2006. Yeah, as the Senior VP 00:04:13.479 --> 00:04:15.900 of Civic Leadership and Chief People and Program 00:04:15.900 --> 00:04:19.750 Officer. Overseeing 3 ,500 youth corps members, 00:04:20.050 --> 00:04:22.810 he created the Give a Year program, which is 00:04:22.810 --> 00:04:25.290 now the City Year Alumni University Partners. 00:04:25.610 --> 00:04:28.230 His expertise was in such high demand that he 00:04:28.230 --> 00:04:31.209 even traveled to Italy in 1997 to help reform 00:04:31.209 --> 00:04:33.230 their national service system. Wow, I didn't 00:04:33.230 --> 00:04:35.149 realize it was international. Oh, yeah. And he 00:04:35.149 --> 00:04:36.810 worked with an American Jewish Committee task 00:04:36.810 --> 00:04:39.949 force in 2006, recommending a U .S. national 00:04:39.949 --> 00:04:43.019 service strategy. He was the architect. Which 00:04:43.019 --> 00:04:45.300 sets up his return to the Pentagon. And the scale 00:04:45.300 --> 00:04:48.620 here is just staggering. In 2010, President Barack 00:04:48.620 --> 00:04:51.420 Obama appoints him as the deputy undersecretary 00:04:51.420 --> 00:04:53.579 of defense for military community and family 00:04:53.579 --> 00:04:56.339 policy. The scope of responsibility in that role 00:04:56.339 --> 00:04:58.459 is almost hard to wrap your head around. Let 00:04:58.459 --> 00:05:00.519 me just list the numbers for you. He was overseeing 00:05:00.519 --> 00:05:04.019 2 million service members, 1 .2 million spouses, 00:05:04.480 --> 00:05:08.639 2 million children, over 2 million military families 00:05:08.639 --> 00:05:11.399 worldwide. He's basically managing the civic 00:05:11.399 --> 00:05:13.920 infrastructure of a small country. Exactly. Including 00:05:13.920 --> 00:05:17.019 the school system. He oversaw the DODA, the Department 00:05:17.019 --> 00:05:19.860 of Defense Education Activity. That's $90 ,000 00:05:19.860 --> 00:05:24.709 finance. 194 schools. 14 districts spread across 00:05:24.709 --> 00:05:28.389 12 foreign countries, seven states, Guam, and 00:05:28.389 --> 00:05:30.829 Puerto Rico. And he didn't just maintain it. 00:05:30.889 --> 00:05:33.829 He overhauled the infrastructure of 160 public 00:05:33.829 --> 00:05:37.069 schools on military installations. Yes. And on 00:05:37.069 --> 00:05:39.910 top of that, he spearheaded the Military Spouse 00:05:39.910 --> 00:05:42.110 Employment Partnership. Which was so necessary. 00:05:42.189 --> 00:05:45.269 Military spouses face huge economic penalties 00:05:45.269 --> 00:05:47.769 because of constant relocation. Employers wouldn't 00:05:47.769 --> 00:05:49.810 hire them because they knew they'd move. So Gordon 00:05:49.810 --> 00:05:52.920 brings together 400 employer partners. to create 00:05:52.920 --> 00:05:56.879 portable careers, resulting in over 120 ,000 00:05:56.879 --> 00:06:00.079 military spouses getting hired. That's real tangible 00:06:00.079 --> 00:06:02.720 impact. It's no wonder he was awarded the Secretary 00:06:02.720 --> 00:06:04.959 of Defense Medal for outstanding public service 00:06:04.959 --> 00:06:07.600 for this. He approached defense not just as weapons 00:06:07.600 --> 00:06:10.160 or tactics, but as human community resilience. 00:06:10.540 --> 00:06:12.360 Caring for the families behind the soldiers. 00:06:12.540 --> 00:06:14.519 Precisely. You fortify the family, you strengthen 00:06:14.519 --> 00:06:16.519 the military's operational readiness. And he 00:06:16.519 --> 00:06:18.660 kept working on that civilian -military gap after 00:06:18.660 --> 00:06:20.699 the Pentagon. He became the founding chair of 00:06:20.699 --> 00:06:22.980 Service Nation, Mission Serve. Which has now 00:06:22.980 --> 00:06:24.699 got your six under the Bob Woodruff Foundation. 00:06:25.139 --> 00:06:28.339 Right. Working with Army vet Ross Cohen. Gordon 00:06:28.339 --> 00:06:30.660 created over 30 partnerships that were actually 00:06:30.660 --> 00:06:33.240 inaugurated by First Lady Michelle Obama and 00:06:33.240 --> 00:06:36.720 Dr. Jill Biden on Veterans Day in 2009. Again, 00:06:36.920 --> 00:06:40.079 building infrastructure to help veterans reintegrate 00:06:40.079 --> 00:06:42.339 into their civilian communities. But here's where 00:06:42.339 --> 00:06:45.040 it gets really interesting. You'd think after 00:06:45.040 --> 00:06:47.420 the Pentagon, he'd just retire or join a think 00:06:47.420 --> 00:06:50.199 tank. Right. Take it easy. But no, he makes a 00:06:50.199 --> 00:06:52.720 massive pivot into the high -tech frontier. The 00:06:52.720 --> 00:06:55.540 AI and digital innovation space. Exactly. He 00:06:55.540 --> 00:06:58.120 becomes the chief strategy officer of Upskill, 00:06:58.240 --> 00:07:01.319 which is a smart glasses software company, then 00:07:01.319 --> 00:07:03.779 chief global officer of Connected Living. And 00:07:03.779 --> 00:07:06.139 currently, he serves as senior strategic leader 00:07:06.139 --> 00:07:09.019 for AI and digital innovation at Document Storage 00:07:09.019 --> 00:07:12.410 Systems, Inc. It seems like a sharp left turn, 00:07:12.529 --> 00:07:14.810 right? How does a retired Army colonel and national 00:07:14.810 --> 00:07:17.269 service advocate end up leading AI strategy? 00:07:17.589 --> 00:07:19.769 It sounds totally disconnected. But it's not. 00:07:19.889 --> 00:07:22.350 It's perfectly aligned. By being a lifelong learner 00:07:22.350 --> 00:07:24.709 who focuses on how tools and policies empower 00:07:24.709 --> 00:07:27.129 people. That's the core lesson for the listener 00:07:27.129 --> 00:07:29.430 here. Oh, I see. Technology is just the new tool. 00:07:29.670 --> 00:07:32.459 Exactly. Whether it's AmeriCorps volunteers or 00:07:32.459 --> 00:07:35.180 AI at the VA, he's building systems to support 00:07:35.180 --> 00:07:37.579 human beings. That's why he's also an advisor 00:07:37.579 --> 00:07:40.819 to startups like UniteUS and Warrior Centric 00:07:40.819 --> 00:07:43.860 Health. So the core mission never changed, just 00:07:43.860 --> 00:07:46.259 the leverage she was using. Precisely. That is 00:07:46.259 --> 00:07:48.699 such a powerful takeaway for you as you think 00:07:48.699 --> 00:07:51.680 about your own path. Robert L. Gordon III's life, 00:07:51.819 --> 00:07:54.339 which, by the way, is decorated with honors like 00:07:54.339 --> 00:07:56.980 the Legion of Merit, the Franklin Award, and 00:07:56.980 --> 00:07:59.500 Princeton's Edward P. Bullard Distinguished Alumnus 00:07:59.500 --> 00:08:01.860 Award, it proves you don't have to pick just 00:08:01.860 --> 00:08:04.620 one lane. You really don't. You can master the 00:08:04.620 --> 00:08:07.759 military, government, nonprofits, and tech as 00:08:07.759 --> 00:08:09.620 long as your core mission remains consistent. 00:08:10.300 --> 00:08:12.220 And this raises an important question, a final 00:08:12.220 --> 00:08:14.740 thought for you to chew on today. Yeah. Based 00:08:14.740 --> 00:08:17.519 on Gordon's life work of merging civilian and 00:08:17.519 --> 00:08:20.120 military populations, like when he combined those 00:08:20.120 --> 00:08:22.060 West Point cadets with AmeriCorps volunteers, 00:08:22.439 --> 00:08:25.620 what would happen to our society's current political 00:08:25.620 --> 00:08:29.259 and cultural divides if a unified mandatory national 00:08:29.259 --> 00:08:31.759 service program were implemented today? Oh, wow. 00:08:31.879 --> 00:08:34.259 Would the empathy generated by working alongside 00:08:34.259 --> 00:08:37.019 people from entirely different backgrounds solve 00:08:37.019 --> 00:08:40.299 the modern crisis of connection? It's something 00:08:40.299 --> 00:08:43.100 to think about. It really is. Shared struggle 00:08:43.100 --> 00:08:45.960 might just be the adhesive we're missing. Well, 00:08:46.019 --> 00:08:47.879 we want to thank you so much for joining us on 00:08:47.879 --> 00:08:50.120 this deep dive today. We hope this masterclass 00:08:50.120 --> 00:08:52.759 in adaptability gives you some inspiration for 00:08:52.759 --> 00:08:55.600 your own career pivots. Keep exploring, keep 00:08:55.600 --> 00:08:57.200 learning, and we'll see you next time.