WRM009: Lessons from the Front Lines of War – Interview with General Robert Hipwell

What’s it like to be dropped deep into the jungle in enemy territory where anybody you see probably wants to kill you? What’s it like to be in charge of the lives of thousands of men? In this interview, General Robert Hipwell shares his experiences and lessons from a lifetime of military service.


Robert Hipwell Transcript

Doug: My name is Doug Greene and I’m interviewing General Robert Hipwell.

Robert: Well, yeah, that’s right Doug.

Who I met through Toastmasters. He’s in the same Toastmasters group I’m in. And at first when they call them “The General” I thought they were just kidding. But then I found out later, he really is a general … 

… Retired General ..

But I don’t think I’ve ever known a general before. And I have my own adventure stories. And I started talking with Robert about some of his own past experiences – both in Vietnam and Afghanistan and other things he’s done. And it was fascinating.

What I’m interested in finding out – the reason I want to interview him is – I know that in his work, in his life, having been in Vietnam on the front lines, being in Afghanistan and all of that, he probably has some incredible experiences where he’s learned some life lessons that I hope we can pass on to the viewers that you can use in your own life. 

And this podcast, which is called What Makes Them Tick: Learn Life Lessons from Extraordinary People,  I see Robert as somebody who has led an extraordinary life, and likely has some really incredible lessons to teach us. So Robert, thank you for joining us. 

You’re welcome, Doug. Thanks for having me here with you today. It’s awesome adventure for me to talk to him to another high-spirited, adventurous person like yourself. I think we glean off each other, and we inspire each other to talk about and learn about each other’s adventures. It’s interesting to hear other people like yourself that have such a high threshold for adventures and a “zest for life” as we say, right?

Yeah. So why don’t we begin at the beginning? Maybe we can give the overview first. We’re gonna talk about at least three phases of your life. You’ve mentioned there might be four …

Okay, first of all Doug, thank you again for talking with me here today. 

In a broad, very concise way, I guess you could say I’m the son of an immigrant family, right? My father and mother were born in England, and so was I. I came to California via Canada first. And then I went to high school in San Diego – grew up in San Diego. 

And during that time, at the height of the Vietnam War in 68, the draft was going on. I anticipated I would get drafted anyway, so I joined the army, signed up for three years. And all I wanted to do initially in the army was to be a paratrooper. I saw a lot of movies and videos about World War II and paratroopers and the 101st Airborne. So I joined the army to be a paratrooper – and I did join the army. We went the “buddy system” at that time. 

A movie came out with John Wayne called The Green Berets. It took me over the edge. I was thinking about going in the army. San Diego is a Navy and Marine Corps environment. And my buddy in high school went in the Navy, was a shore patrol man, and told us all the war stories about how they treated the Marines. 

So I got turned off about going into the Marines, joined the Army. And at the height of the Vietnam war, 1968, we had half a million soldiers in Vietnam plus. So they had a huge standing army in Vietnam. In the Tet of 68 we lost a lot of people – NCOs, first sergeants and second lieutenants. So the army had a school set up to quickly promote sergeants and lieutenants. So I went to a 90-day program at 18 years old. And I was a Sergeant in 90 days at 18. 

As soon as I got to be a Sergeant, I went to Ranger School, Airborne School, and then over to Vietnam. So I did a tour in Vietnam as a long-range reconnaissance assistant patrol leader. 

There was six of us on the teams. On those teams we went out 50 to a 100 miles in the enemy’s area to do reconnaissance and surveillance and report back to Higher of what was going on with the enemy activity – mostly along A Shau Valley on the Ho Chi Minh Trail. 

So after Vietnam, came back after three years. Came back to San Diego, worked in a shipyard with my dad for about six months. Then they ran out of contracts, got laid off, and I decided to go to England because my wife I had met during my time in the army was British. 

Went to Great Britain for three years. Went to school at night on the GI Bill, stayed in reserve component. And then when I came back three years later, I joined the California National Guard. And they had officer training program – which I was selected for. I went into that. Two years later I became a Lieutenant. So I worked myself up from Lieutenant in the Reserve National Guard. Then I switched from the National Guard to the Army Reserve, and then I kept going up in rank, and – before you know it – I’m an officer. 

Then I got to be captain with special forces. Then I got into special forces (US Army Green Berets) – I was an 18 commander for 10 years. 

And then after that I went into military police. And towards the latter part of my military career, I had the good fortune – and the people I worked with were very good – was able to get promoted to Brigadier General. I took a command over to Iraq as a Commanding General for the 300th Military Police. 

And I was in charge of the largest detainee operations in the world at that time – 20,000 detainees down in Camp Bucca in Southern Iraq for the first part of the tour. And then we moved up north to be the Task Force North. So I worked in the same location as Saddam Hussein. 

And I was there earlier on in another tour when we got the two sons. And towards the end of that tour, in December of 2003, we actually captured Saddam. And we kept him in our compounds – the compounds that we kept him up in Baghdad. So that was quite an adventurous time.

But my, I consider my three phases in the military to be an enlisted ending as a Sergeant, to being an officer, to being a General Officer in the army. So that’s kind of three main focuses of my life there. 

And subsequent to that, I’m very fortunate and blessed to have a large family. My wife and I have nine children between us. We have seven sons and two beautiful daughters – one of which you met today. 

And of my sons, six of my seven sons have been in the army. Three are still serving in uniform and to this day one is still in Afghanistan. He’s a special forces medic and special forces team Sergeant in Afghanistan right now. So, uh, my sons have followed me in the military. And that was one of my ways of helping them get their education – because I let my uncle pay for their education instead of their dad. Same way as I got my education!

I actually do, as you probably know, have two PhDs and earned a PhD and an honorary PhD, three Masters degrees and a couple of Bachelor’s degrees. But all that was based on the GI Bill and working through night school my entire career and having a full-time job and raising a family.

So nobody’s ever gonna convict you of being an underachiever, are they?!

Yeah, that’s probably a true statement.

So let’s dive into – we’ll come back to the later part. Now he’s helping veterans, but we can dig into that later. Let’s go back to when you’re in the military the first time around. Okay,you’re on the forward lines. You’re working as basically scouting operations,

Right. Long-range reconnaissance patrols is what they’re called.

So what you’re out there to do is to find what’s going on, get information, get in, get out, not get killed. And come back with the best quality information you can, right?

Right. Radio it back and bring it back. 

So it was two-way communications. We’re in the field. We’re always communicating to Higher what we’re looking at. So if they want to have what we call “actionable intelligence” … if we find something that Higher headquarters wants to, for example, destroy, then they’ll call in an air strike. They’ll call B52 bombers. They’ll call in artillery or whatever. 

But our job is to immediately report activity that we see periodically. And then once we get back they debrief us as far as the whole mission. Could be a five to seven day mission typically.

So that’s the “What.” But let’s dig into the “How”. Because I think that’s the real interesting part. There’s six of you. You’re dropped in by either parachute or helicopter.

Huey helicopters.

So they, they drop you in right into enemy territory.


And there you are!

Right. You’re there for the duration. And as you mentioned, our job is not to make any contact with the enemy whatsoever. It’s to just to be quiet, go really slow, and observe and report back.

So talk about what that’s like. How do you not get seen? How do you deal with situations where you do get seen? How do you work cohesively as a team? What makes a team work? What makes a team not work? Things like that.

The day to day stuff is a challenge. But the Army in those days was a draft army. So a few volunteered to be in a unit such as I was in – in the ranger unit. You were a volunteer – so we all more or less all wanted to be there, versus a conventional infantry unit, which would be people just serving because they got drafted. 

So in a higher-mission unit, my higher purpose mission unit for example, everybody volunteered to be in this unit. So we had been, like I mentioned earlier, I had gone to a lot of training stateside before I was sent overseas. Advanced training, ranger school – which is two months long, recondo school, quite a few series of trainings before I got to Vietnam. 

And once I got there I was assigned to a team as the assistant patrol leader as an E5, and it was run by an E6. So I had a senior person to me, and I could mentor from him. And then we had four other people on the team.

We worked together. We trained while we were in the rear. We typically had five to seven days out, two to threes days back. So the first day we came back we were basically refreshed and trying to get back into situation. 

But the other two days were training, always working together, always knowing each other’s strong points and weak points so we could anticipate any problems that we might have out in the field together. So we lived in the same Quonset huts together. We went to chow together, we exercise together …

The whole point is basically to become one, right?

Become a cohesive unit. Right. 

I get that part. So you’re out there. It sounds like one of the things that really helps is the amount of training. When a situation comes, you already have a pre … you’ve got a Plan A.

SOP they call it. Yeah, standard operating procedure, right? 

We practice, we rehearse. If we get ambushed from the right side, what happens? If we get ambushed from the left side, what happens? So we practice and rehearse that before we go out to the field. But whatever happens out there is going to be unique. But we have scenarios for as many opportunities that might come our way as we can.

So having that pre-plan is standard, the standard operating procedure … talk about the value of that.

Well, I think it has to be ingrained in your muscle memory, so that if something happens in the field, you don’t have to think about it. “Hey, what’s happening? Is this a life or death situation?” So you have to make decisions based on what’s coming at you to negate that situation, and be victorious, and come through and get your mission completed, and get you all out of there safely.

So talk about that. One reason I’m asking you about this, there was a moment when I was in a motorcycle accident. I hit an antelope at 70 mph head-on. And I had recently taken an advanced motorcycle driving class. And I remember they talked about the patches, you know, it’s like you’re looking at these different forces happening – forward force, sideways force. 

And the idea is you don’t want to change your movement patch or else you’re going down. So you want to stay on a straight line, keep going in a straight line, and don’t do anything that’s gonna mess that up – if you can. And when I hit the antelope, there was this moment of, you know, kind of like, “Oh shit.”

But then the lessons learned from that advanced riding class kind of dropped into place. It was like, “Okay, don’t do anything. Don’t turn, don’t do something stupid. Don’t hit the brakes if you’ve got a straight line.”  And I knew to ride that straight line out, and that’s what saved my life probably, or at least from, you know, I didn’t drop the bike. 

The antelope went underneath the bike, locked up the rear wheel, and we slid for 150 feet. Then it came off, and then the bike took off. You know, it was because the throttle was locked on high. And there were a series of maneuvers I made that came automatically. 

Well, I’m assuming, and I remember how cool that was that it happened. And I can imagine that in your situation that’s amplified by a hundred. When there’s people all around you, there’s bullets whizzing by and  … I can only imagine. 

So what is the … talk about what the feeling is like when you actually move into response mode. Do you even feel anything? Are you thinking about anything? Does it just happen automatically?

It’s more or less like you said – it happens automatically – Instinctively. An analogy, like you mentioned in your motorcycle accident where things happen instantaneously, and you start to think about them later and reflect: “What did I do? How could I have done it better? What about this? What about that?” 

So in a combat situation, you’re trained to expect certain scenarios. And you train and train and train some more – and rehearse and train. So when something does happen, you automatically go into reflex mode. And you react based on your reflexes or muscle memory. And then later, when things calm down to a certain extent, then you start to thinking about, you know, logically. 

And plus you remember, as most combat is, is engaged by people that are young – under 25 for example, I was 18 years old – so in one respect, you almost feel bulletproof, right? The fear of dying is not there like it is when you get a little older and you think, “Oh man, what was I thinking?? What was that? Why did I do that?” Right? 

So you’ve got that young eager “that won’t happen to me” thought and that you’re bulletproof, for one thing. But other people on other teams are getting killed and wounded and you know that possibility is available to happen to you. 

However, you think because of your training and your expertise and the confidence in the men around you, that they’re going to look after your back and you’re going to look after their back, that you’re going to be fine.

So it sounds like part of it of this is just getting out of your own way. Right? And the training really teaches you how to do that. That thinking part that gets in there, that can set up that extra bit of time – that can make the difference between life and death – is kind of removed because you know instinctively what to do.


So talk about working as a unit. There’s six of you there. It’s one thing if you’re just responding on your own. But to work as a group in that way, it’s like taking it to another level. 

So you train together. I assume there’s sort of these, I don’t know, maybe you learn how other – you mentioned that each guy has their strengths and weaknesses – and you probably rearrange yourselves or the energetics of the group so that you’re each playing to your strengths. Like the guy that shoots best on the right side at x-yardage, that’s where he goes, or something like that.

For example, I’m a left-handed shooter. So most of the time I would guard the right side of the trail, because my weapon would be at the ready position, so I could bring it up. So I would be focused on the right side of the trail. 

A right-handed shooter would have his weapon slung for the left-hand side, so he could look on the left-hand side of the trail. 

But for example, even before we go out in the field, there’s a two to three-day preparation period. Well, in the jungle everything smells dirty, rotten and smelly, right? So once we get our mission assigned to us, we stopped taking showers, we stopped brushing our teeth, we stopped putting any fufu smells on us. 

So we’re already stinky by the time we go out to the field, right? Because your senses really get alerted when you’re out in the field. They go to a higher level. You can smell things in the jungle that you wouldn’t smell going back. After three days you smell so bad, you really don’t smell yourself anymore. 

And then we thoroughly look at our equipment, make sure we don’t have any rattles, anything that makes metallic sounds. For example, on our weapons, on the dust cover of our weapons, we taped a cigarette butt to the dust cover of our weapon in case we had to pull a weapon back to cock it or move it. Then it wouldn’t make it a metallic sound when the dust cover opened up. 

So we go through and we tape things down. We shake and inspect each other. We take all our water with us – we have bladders of water. And if somebody opens a canteen, we pass it around the group, and we all drink the same canteen water. So we don’t have any movement of waters making noise while we’re moving on our trails. 

We typically went very slow. We move for 50 minutes and stop for 10 minutes to catch our breath so we wouldn’t get caught in the triple canopy jungle and try and get frustrated to move and make noise. Move for 50 minutes, rest for 10. 

And at night one of us at all times was awake. So we take turns. We get into a wagon-wheel sort of environment. We’d pass the radio. You would have it from one to two, the next person have it from two to three, and so on and so on. 

And our Higher headquarters, every hour we had to come on the phone and listen. We wouldn’t talk. We would never talk out in the field. It was always a whisper or hand and arm signals. So we had to do that.

So at nighttime our higher headquarters would call us. They usually have five to six teams out there in the environment. And they would call us up and say – our team was 1-2 – they say “Team 1-2, team 1-2. If your situation is negative, break squats twice.” So all we had to do was – on our hand receiver –  just go (makes clicking sound) so we wouldn’t have to talk. 

So they knew that we were okay and that was our SOP, that everything was okay with us. And if we missed three consecutive situation reports, then they figured the worst – and they’d send a reaction team out to our location, our last known location. They would anticipate that we had been either killed or captured.

Now this is before GPS’s were in use, and they didn’t know exactly where you were.

Way before GPS. 

So they generally knew on the map like okay, they’re covering the 75-100 miles, they’re moving ….

Oh no, no. It’s way smaller than that. They had like six teams out in the area. We had maybe at the most a three or four-mile box on the map – grid squares. So we had three or four miles that we would travel through.

And we’d set up. We maybe move a mile a day from one location to the other – and slowly. We would never stay in the same spot twice. We would never sleep in the same area twice. And when we camped at night – just in case they had observed us, and we didn’t know that – just before dusk we would set up, sit down and be quiet, and prepare to move to another place.

And when it got dark we would leave the last place that we are at and go to another place for the night. So if someone saw us in the jungle, and they go, “Oh, they’re over there by those trees” – once it got dark we would slowly and quietly move to another location and set up there for the night and start the whole sequence over again. 

And only one of us would eat at a time. So we didn’t ever want to be compromised. We never had any campfires. It was all long-range rations where you put water in a condensed food packet and eat that way. And many times were able to observe and report from enemy activity based on their cooking and their campfire smells – so we could smell their food coming downwind to us.

Hmm. So did you ever have to face off with the enemy from time to time?

Yes, we did It was quite an exciting adventure to tell you the truth. One adventure that really sticks out, and the most predominant adventure was – on one mission we were on, and we were monitoring – we never actually go on the top of a trail, but there was a high speed dirt trail that the enemy would use as a resupply trail. 

So we walk along 10-15 yards to the side of each trail and observed the trail at the top. So we were paralleling this high-speed trail on about our second day in, and we heard some enemy activity on the trail. So we quietly got down in a crouched position, pulled our weapons up and – we’re so trained that we’re not allowed to engage fire unless our team commander, team Sergeant engages. He’s the one that initiates the fire. So no one, if they get afraid, they don’t pull the gun and compromise everybody.

So anyway, we hear the enemy coming down the trail. We all have our weapons up. We’re all camouflaged up. We’re all sweaty, and we could see that people walking through the trail. They had a flank guard on both sides of their patrol, and the flank guard didn’t see us, but he happened to come about 10 feet from us. And then he had to relieve himself. 

So he had had his AK 47 slung over his shoulder, down in the ground, started relieving himself in our direction, and he caught our eyes and we caught his eyes. He knew the second he saw us that we were all pointing our weapons right at his chest. And he knew – and this was all instantaneous – and he knew that if he even tried to pick up his weapon, he’d be dead before he could even raise it halfway up. Because we had our weapons on automatic, ready to engage, waiting for our team sergeant to engage. 

We didn’t engage at that time, so he kind of looked at us. He saw what was going on, he slowly zipped up his pants, backed up to the trail and started yelling in Vietnamese. And then the whole column of Vietnamese ran down the trail, and we still were there waiting. We didn’t engage them at that point. 

They got down the trail and our team Sergeant basically gave us the high sign to get the hell out of there. So as soon as we decided to get out of there, all hell broke loose. They started to attack us.  There was about 28 to 30 that we counted. So it must’ve been more than that. So 28-30 guys were attacking us. So we took off in the opposite direction, and they were in pursuit of us. So a firefight erupted. 

Fortunately, none of us were shot, ambushed, or hurt by hand-grenades or anything else. We were able to evade the enemy. After about four hours we put so much distance between us and them that we were able to get detached from them. 

We were in triple canopy jungle, we couldn’t land a helicopter. We told Higher, and they sent out rescue party to help us. But the triple canopy jungle … they couldn’t land the helicopter anywhere else. So we found a spot that was not so densely populated. We put our claymores on the ground – claymore mines – and we blew a hole in the canopy so that the helicopters could lower ropes down. So they did. 

Three helicopters, came over, dropped two ropes in on either side of the helicopter. We had Swiss seats set up that we could tie around our waist with a bowline.  So they hoisted us out of the jungle two at a time, going upside down. And they took us to the A Shau Valley about an hour away.  So we were hanging upside down in this helicopter spinning around in circles as we were taken out of the jungle. 

We all survived that mission. And that was August 6, 1970. And to this day we communicate with each other. We call that “upside down day”.

Snap link – we have the rope, hooked it into the snap link. We all carry six feet of rope and a snap link just for those situations in case we had to get extracted at the last minute. We call them snap links. 

But we kept all our equipment. We were not going to leave any equipment behind so that the enemy could use against us or any of our troops. So we took all our backpacks. And as soon as we got past the first layer of trees – we were inverted because of our heavy backpacks upside down, spinning in circles underneath the helicopter. And when they landed, we were so disoriented and upside down, we couldn’t even get up there. The door gunners had to come over and grab us and pull us into the aircraft to get us the hell out of there.

So from that period of time, what are the three biggest lessons you get pass on?

Well, the biggest lesson is teamwork matters. You’re not there for your own personal safety; you’re there for your buddy next to you. So you go in as a team, you come out as a team, you work together as a team, and if the team succeeds, you succeed. Right? 

And you do lose friends along the way through combat, through sickness or illness. But the core team, four or five members, stays together. But they do rotate in between from that. So I would say teamwork is the core.

Having to know your strengths and weaknesses, and know your buddy’s strengths and weaknesses, is another important aspect of that. 

And then motivation and drive – why are you doing this? Right? You’re doing it for the unit, and to support the unit and the unit mission. So those are three big things.

So the motivation, um, talk about that a little bit.

So in addition to those three elements of lessons learned – of looking after your buddy and your buddy, they’re looking after you, are completing the mission, and having focuses …  the next part of that – I think is very important is that the human body can do a lot more than most people ever anticipate it can do, right? 

Instead of the normal things, if you task your body, not, not a one time thing – but you can if you need to – but in the training that leads up to that, you put your body to a lot of extremes, right? For lack of sleep, physical endurance, a lot of physical demands on your body. And your body can take it for the most part, unless you don’t get to the failure point. But going to ranger school, you have limited sleep, you have limited food, you walk the equivalent of 200 miles in two months, right? You’re up most of the nights. 

So it’s a similar situation in combat. And I know from my experience in Vietnam, and my experience in Iraq and Afghanistan, the higher you are in rank, typically the less sleep you get at night. Generals, as a whole, when they’re in combat, sleep less than four hours a night. That’s a demand you put on your body because you need the time and focus and attention to do a myriad of duties and tasks and functions. 

So the demands you put on the human body – you can train your body to do what we would think to be superhuman things for the most part. But it’s a matter of training the body up and getting used to that and enduring those long terms.

Is there a – I’m really curious about the four hours of sleep part – is there a point at which you you can maybe do that for a month or two or three, and then at some point it’s like you just sleep solid for four days in a row.

That’s a good point. Well, it comes and goes. 

Having had six combat tours from Vietnam, Afghanistan and Iraq – I worked with generals, worked on a general’s staff and I worked for the general in Iraq – when the war first kicked off in 2003 – he got two to three hours a night. He did this for at least six months straight that I can see. 

He’d go to bed at one o’clock in the morning, he’d be back in the office by four o’clock in the morning at the latest. If the situation demands it and you need to perform at that level, you can do that almost indefinitely.

But at some point, like general Stan McChrystal for example, he slept less than four hours a night. He ate only one meal a day. When the Rolling Stone reporter was attached to him and watched and followed him around … he was with him for like six weeks solid, and he only saw him eat twice in that six week period. 

He’d eat one meal a day. And he slept less than four hours a day. So he’s a high energy person, he’s motivated, he’s self-driven, he’s responsible for a lot of men’s lives, a lot of men and women’s lives. So he takes his job seriously.

So here’s a question. Do you think that’s – the nature versus nurture question – is that something that he already had that maybe others don’t and maybe he rose up through the ranks in part because he just had that capacity to keep going and going and going, whereas others might not find it – or is that something that he developed along the way or is it a combination?

I think it’s a combination of both. Knowing Stan McChrystal was both a ranger and special forces officer prior before becoming a general, and they push your physical extremes, your mental extremes and you’re trained. And as you move up in the military, like in civilian world, you have more responsibility and more things that you’re responsible for.  So there are more expectations. 

So it’s kind of a train thing. Part of it’s being trained and part of this being – if he can’t make the stay in the military, like in civilian world – if you can’t make it, you don’t get promoted.

Yeah. There’s a filtering process that’s going on here

And there are certain requirements – physical requirement, mental component to that, and an educational component. In the military you have to have military classes, education to move up. You have to have physical standards. You have to be able to shoot accurately. You have to have a lot of different standards in order to move up.

Okay. Let’s go onto the next phase in your military career, which is, describe that.

The officer phase? After Vietnam, I got a reserve commission in the state of California from OCS California Military Academy to become a Lieutenant. So it was a two-year program. I joined the national guard in San Diego and for two years – which was one weekend a month and two summer camps – at the end of the second summer camp you’re commissioned as a dual commission. You get a state of California commission, and you get a federal commission simultaneous to that. So they meet all the standards of the Army. 

However, you’re working for the state governor except for times of emergency. And we know in California for example, we have four seasons – fires, floods, earthquakes and riots. So, so if the governor determines that he needs assistance because he doesn’t have the resources to put out fires, or there’s a flood that they can’t deal with, or there’s a riot in LA or anywhere else in the state that the state’s resources can’t handle, he’ll call in federal assistance. Right. 

So you get a dual commission. And most of the time you worked for the state governor in any state. But then there are times when you work for the federal. Like for example, in Desert Storm and in most recent in 2003 in Iraq, at one point 53% of the troops on the ground were a reserve component, either national guard or reserve component, because the active duty strength was not there in numbers like it was in WWII. 

We had 150,000 troops on the ground at the peak of the second Iraq towards the surge. And 53% of the troops were reserve components. That that could be good and bad – because as we saw on the bad side of that, Abu Ghraib came out of that. And that was the debacle from the Iraq war. And that was a reserve component, military police unit out of New York that got disbanded and got disheartened. 

And I was there at Abu Ghraib. I was a Proverse Marshall for Iraq during that period. I kept advising my generals, we need to get out there and provide these guys more resources. And it was really a hellhole out there. But the general told me, “Hey Bob, there’s a lot of hellholes in Iraq, so we’ll deal with that when we come to it.”

But either case, Abu Ghraib happened, and that was a reserve component unit that didn’t have the leadership and the experience – the many, many years it takes like an active component to get to that level. They were called up six months before the war started. They extended them over there in Iraq for another 90 days, and their morale went south. And the leadership wasn’t up to speed to handle the mission.

If you could give that group advice now, maybe not the group, but the people that … I don’t know how. How could it have been done differently? We’re talking about a scenario that went south now.

Yeah. Abu is a hotbed for insurgency. It’s close to Ramadi and Fallujah; it’s within 20 minutes to a half hour at the most. So they would come and attack it almost every day – drop mortars in, dropped by mortars out of the back of a small truck, and then get back on the road and leave.

So it was attacked. And at one time – I had lunch two days ago with a friend of mine was in Abu with me – he flew in from out of town on a business trip, and we were reminiscing about that. And at one point 39 people were killed and 115 were killed at one attack. 

These attacks happened almost daily in Abu Ghraib prison, which is about a 40-acre complex with high walls around it. They would lob mortars in, and artillery rounds in on occasion, but mostly mortar rounds. And once in a while, do a ground attack. 

Well, the resources they had there weren’t trained for external protection. An MP unit like that is trained for internal protection and securing the detainees and prisoners of war if there is any.

So all of a sudden you have a vulnerability and an enemy that seems to be very quick at adapting to weakness.

Just like any war, they look for a weakness, and they try to exploit the weakness. And in that situation there wasn’t enough ground forces on the outside to protect the environment fully. And as we had gone into Operation Iraqi Freedom with less troops than we normally do, I would say … because I think the department of defense Rumsfeld’s whole philosophy, and I can sum Rumsfeld’s whole philosophy up in six words.  And my interpretation is “more toys, less boys, outsource it.” 

So once again, “More toys, less boys, outsource it.” Meaning he wanted to use high tech weapons to supplement the regular trigger pullers. So we only had 150,000 troops on the ground, and outsourced it. We had contractors like Blackwater. KBR did all our dining facilities and maintenance and upkeep inside the operating basis. And so more toys.

He wanted us to use all these high tech … keep the government contractors in business, which would also help the soldiers obviously. But I still think, for example, as a military police officer he wanted us to use all high tech equipment to smell for explosive devices. Well, we had dogs. Dogs worked fine, bomb-sniffing dogs.

If it’s not broken, don’t fix it.

We had blue force trackers. We talked about in Vietnam – we didn’t have blue force trackers. Well blue force trackers are what the Air Force has. They can track aircraft in the air. But blue force trackers weren’t at the evolution where all the troops and all the vehicles had them when we initially started. 

We got the blue force trackers so we can track our own units. But we didn’t have them all at the time. We used drones to look around our perimeter and see out. So a lot of the technology was there. But the bottom line is you have to have boots on the ground in order to sustain and maintain victory. You can’t do it as a drive-by, drop bombs and blow up the enemies resources and key locations.

Okay. So going on this next phase, sort of your leadership, describe your next phase. I know that there’s the general phase, but there’s this intermediary phase in between.

Well, to get to general, you start in the officer ranks. There are very rare occasions where you get direct commission – like it happen in Vietnam – that the sergeants, the officers get killed. And even in World War II, the officers get killed off in a battle, and they give you as a senior NCO, a director to move up the chain of command. 

So you get a commission, but then you still have to meet the standards of that rank and that level in the military to move up – whether it’s educational, military standards, military education, firing your weapon, physical standards, all that type of thing. 

So you start off as either enlisted or an officer. So I’d done the enlisted time, I moved into the officer environment, and moved up the chain from company level, which is the first three levels of officer to battalion level.

How many people in a battalion?

Uh, these days could be 800 to a thousand. So say 800 to a thousand in a battalion

And the level below that is a squadron?

Company. A company is anywhere – a ballpark figure is 200 people in a company. It could be 180 it could be 220.

There’s four companies that make up a battalion?

Usually. And then sometimes if the army is going extra strong, they’ll have five – and have two battalions in reserve, and three battalions upfront. So I was a Brigade Commander in my last tour. I had a brigade staff. And I had five battalions that I was responsible for. Each of those battalions had companies and troops that completed their mission.

So what are some of the lessons of leadership you’ve gotten along the way? And how did you grow into leadership? Did it come naturally to you? Did you have to, I mean you’re having to make some decisions where you know people are going to get injured and die. Yeah?

Yeah, of course.

So there’s two parts to that question. One is sort of  – there’s an attrition rate of the people that do and don’t make good leaders, and you rose up through the ranks as one that does lead well. So what were the qualities that you see both in yourself and in others like you that make good leaders and can rise through the ranks. 

And then also how do you sit with those kinds of decisions where you know people are gonna die, and you’re sending people out to do stuff that just isn’t, you know, … victory is measured in a different way than a corporate bottom line like Cisco.

Right. Well in one respect, and more humorous sense, the Army is like the Boy Scouts, right? You’re always going to have adult leadership. Well in the military you always have someone that’s higher ranking than you. So you have somebody that you report to. They coach, teach, mentor and advise you. And then you get at least, at the minimum, an annual report from them, just like in corporate America, where they tell you what your strengths and weaknesses are. You go in before you even start your job and get a counseling from that senior person that you report to.

So there’s a really good mentoring program in place.

Yeah … Pretty good mentoring program. However, you might not have day-to-day interaction with that person. And it may be spotty, especially in a combat environment. You’re in one location and they’re in a different location. 

But you know what their expectations are. The commander above you has his commander’s objectives that he wants you to accomplish, like in corporate America. So you make sure that you accomplish the commander’s objectives above you. Yu get coached, teached and mentored by that person.

So as a kid, were you somebody that seemed to lead pretty naturally anyway? Do people kind of want to follow you? Some people have that ability …

Some people do. I’m thinking back on it and not necessarily.  I was more of a happy-go-lucky kind of guy in high school. I was an average kid in high school. But I excelled when I got to college. And I was motivated because I had already been to Vietnam. I had already seen the good and the bad of man. 

And I actually came back from Vietnam with survivor guilt. My kind of PTSD from Vietnam was survivor guilt. I never got wounded in Vietnam. I saw a lot of carnage in Vietnam. For example one of the missions that we went on, they put my team on this hilltop, and they put another six-man team on another hilltop a couple of miles away. And then within two days that whole team was annihilated. none of them came back alive.

Right? And you think back at that leader?  They could have easily been switched, right? They could’ve put us on that hilltop, and put them on our hilltop, and we could have all been killed and not come back. 

That was May 11th, 1970; that day still sticks in my mind. So those six guys that came back were my age, my peers – and I tried to lead my life knowing that they didn’t have the opportunity to move forward in their life. So in a sense I had survivor guilt at “why am I still here? What’s God’s mission for me? Why am I still on the earth?” Right? 

So I tried to live my life somewhat with the knowledge, knowing that these six men hadn’t been able to come out of it alive. So I was always trying to do the right thing. Just like in the movie “Saving Private Ryan.”

Yeah. I was just thinking about that …

Same sort of scenario. Make it a life worth living. Men have died. And throughout our history, and in the history of mankind, people have laid down their life for us – so we could live the life that we’re now living. 

So I tried to make my life – in a sense – to pay back for those six men – not just those six men, because we lost more than that …

The one that really hit deep …

That one that really hit deep for me.

So, so it gives you a renewed sense of purpose in there too, right?

It sure does.

I want to talk about purpose. One question I want to get into before we go into before that, though, is were you involved in a lot of team sports when you were a kid? Or just team situations?

Not sports as much. I was in the band in high school. I played in the marching band in high school. I played football and, like you, I was into dirt biking and water biking. So I was both in team sports including football, and I liked baseball. My dad was big in baseball, so I was the oldest of four sons. We were all in Little League. So we grew up through the Little League chain. And all of my six sons played in Little League – because I was their coach, their manager and or umpire in different leagues.

The response I was looking for, and that you provided it, is that you had been in team situations when you were a kid and growing up where you were comfortable in it.


Some people like myself, this is where I kind of diverged from that. I had a bad experience in Little League. There was actually a key point where I said “I’ll never get involved with a team sport again.” And that’s when I got into cross-country running, and you know, sort of solo – whitewater kayaking and you know, all these sports that you do on your own. 

So there’s nobody else that has to take consequences for how you are in there – and the same for me. Right. And it’s had a deep impact. You know, both positive and negative way on my life. 

But you came in a place of comfort. I mean, you know, it was just a natural thing to be as part of a team, whether it was a band or football or you know, as a manager for the teams and stuff. So that’s what I was curious about. 

Um, let’s go back to a purpose. So I’d love to finish up this general part too though. Let’s finish up the general, and then come back to purpose. Do we have enough time?


Okay. So as a general you’re up there. You’re playing both a political kind of dance – the amount of things you have to juggle grows exponentially, right? It’s not just about war anymore. It’s about all these things that you’re managing. 

And how do you expand your capacity – or how was your capacity expanded – as you kept rising up? And especially at the General level … what new qualities did you have in yourself that enabled you to do that, that you picked up along the way?

Well, as a reserve component general, being different than an active component general, we are a community-based organization versus institutional. We’re not on a military base, and I have close proximity to my staff and my people. As reserve component I was in charge of a unit that was in Inkster, Michigan. 

And I had outlying units in 17 States. And the reality is, for the three plus years I was brigade commander, my car, spent more time in the long-term parking lot at the airport than it did in my driveway. Because it was typical that I would be gone five, six, seven days in a row, be home for a couple of days and then took off again.

Because I was either working with Higher headquarters, at a conference training session, or going to my subordinate units, working with them, helping them, coaching, teaching and mentoring my junior leaders so that they could be effective in their missions.  Because if they’re not successful, we’re not successful. So it’s a teamwork.

And that’s kind of a built thing. You go, you get trained out yourself, and then you go out and you implement the dream that you’ve got. The Army’s very big into leadership, and they train for leadership. They have NCO leaders, they have officer leader. Every level of military has a certain level and expectation of training that goes with being a leader.

Okay. So your time as general was actually spent state side …

For the most part – except for the 400 days that we were assigned to travel to Iraq and do my mission in Iraq. So my whole unit was activated from the reserve component out of Michigan. 

And in fact the Army Reserve was so short of troops at that time, because we were about eight years into the war, that we were only 50% where they had to draw in people from cross-level people into my unit from other units so that we can go over and complete our mission. 

So we were on 400-day orders. I went over to Iraq, came back, and then about 50% of the unit went back to their own unit, and the rest of the unit stayed in Detroit.

So, do you want to talk about that Iraq piece? Is there something special to be gleaned from your experience there? You brought Hussein in watching him. What was ….

And we also had the high-level detainees – the pack of 55, the deck of 55. We had those in our custody. Saddam Hussein … the U.S. always had physical custody of him, even though jurisdictionally wise it was the Iraqi government that told us, you know, to take him to Iraqi high tribunal on Saturday because he’s going to go to court.  So we would transport him to court, bring him back. We gave him haircuts, we helped clean and bathe him and all that. 

And towards the end actually, Saddam tried to warm up, as he typically did, try to warm up to people that were keeping him in custody. And he wrote poetry every night. So he’d write poetry and then the next morning he would give it to the soldier tell a soldier his poetry. And then they would take that poetry and keep it as a collector’s item. 

Well, after awhile, they shut that off because they didn’t want him to get too friendly with the troops. So he wrote the poetry, but he kept it to himself. And he also had a monthly allotment of Cuban cigars. So he was given Cuban cigars. After awhile he was allowed visitors in, you know, foreign dignitaries from other countries and family members. And he would have somebody come into to talk with him and, and sit in his area where he was. And they would sit and have a smoke and talk, and then they would leave.

What do you remember most about the challenges of watching over a high level person like him?

From Saddam? No, because he was in a remote secret location. Where Saddam was, was in a bombed out area. When we initially had the shotgun-off phase, and we bombed a lot. 

Actually, Saddam had 65 presidential palaces in Iraq that were huge – three to four stories high. You’ve probably seen pictures of them. They had golden inlaid toilets ,on awnings and golden laid doors. And all that money and expense went for him and his cronies. And the example was he had 24 hospitals in the whole country of 26 million people. And he had 65 presidential palaces. 

So you can see – and only about a third of Baghdad’s population of 6 million people had plumbing, electricity and power. 

They had the resources to put power in for everybody, but it wasn’t on that. It was on him and his cronies and people that they wanted him to stay in power.

Let’s go back to purpose. So you were talking about how the people on the next hill over didn’t make it. And that impacted you very deeply. Right? And you’ve made a choice, a decision at that point, at a really deep level – that you were going to live your life as – what’s the right word? I don’t know – make it a life worth living.

A life worth living, right. Live a good life, and do the most I could in the time allotted for me to make up for the fact that at least those six guys weren’t able to move forward in their lives. They weren’t able to have a family, have a job, contribute to society.

So this is kind of a PTSD moment for you. 


So describe what that felt like, what the experience was like. Not just the outer part, but the inner part that I believe is what probably was the motivation that then drove you to do it. Because you saw something, you think, “Oh, okay.” You don’t think that thought “I’m going to make it a life worth living.” It’s a deep, entrenched feeling that comes up.


And maybe describe that in a way that other people that are facing something similar might understand and give them hope to get through their own experience like that.

Right. Well, I think you have a good sense for that, Doug. It’s not something you think about. It’s not something that you reflect back on it. It’s kind of ingrained in you at that point. 

Over time – there’s quiet times of your life when you think, “Hey, what can I be doing?” For example, you know, getting up early, get up at four in the morning and do physical training. Do push-ups, do four or five-mile runs before the sun even gets up, and go to school at night. All my degrees were done at night school. I got up at four o’clock in the morning, went to the gym, did running, and went to the office. 

When I was in reserve component, was in civilian world, came home, had a large family. I was involved in my kids’ schooling, involved with their activities after school – baseball, scouting. So it kept me busy. I’d rather be busy than bored, so, right. And I go to school two nights a week and when I graduated from school 11 years later, I taught night school for another 10 years. So I was teaching night school at the graduate and undergraduate level. So I taught night school two nights a week.

Let’s go back to that single experience of the company that was just right over on the next hill that didn’t make it … what was that journey like? Just that specific journey going in. How long did it last? Inside where you were like, “uhhhhh”, was it kind of working its way through you inside. And then finally it kind of came out and expressed itself and like, “I’m gonna make this a life worth living” … ?

I don’t think it was a mental thought process. It think anytime there’s a crisis in life that you experience, later you reflect about it”. What if I had done this? What if I had done that? What if this happened? When did that happen?” 

So you kind of internally reflect, and it happens in a short period of time. And then you ingraine that inside you and say, “Hey, you know, that could have been me. That could’ve been us.” So take this opportunity – because you’ve got another fresh day to start with. You might not have that day tomorrow. So accomplish and do as much as you can today to enrich your life. Give back to society and help those around you.

In my own experience of going through that dark place, when I lost a lot of my vision, it felt like there were sort of the “dark night of the soul” way I’ve heard it described. There’s a sensation … for me there was a sensation of … (takes a deep breath, then exhales) 

It was like combination of hopelessness and an emptiness. And I’m actually trying to point to where I actually felt the sensations of it, because it’s a body-felt thing. And it’s a natural part of grieving, I think. Uh, I don’t know. I’m always curious about this area. You obviously came through it empowered.

Right? Well I can understand what you’re saying, but I don’t think it had a physical manifestation inside me in terms of “I was hurt here”, I was heartbroken or I had mental depression. 

Conversely, on the other side, I knew I had to keep myself busy. I didn’t want a lot of downtime – because the old saying “An idle mind is the devil’s workshop”, sort of speak. I wanted to always keep busy and always keep active, read books, go to school, engage with people, talk with people. Um, just keep myself busy.  So rather than have that …

And I did have quiet times, f course. One of the things I did enjoy was getting on my dirt bike, traveling, not extensively, but traveling out in the woods, shut my motorcycle down and just sit and reflect and think about my life, where I’m going and what I want to do.

So busy, not bored. That’s really good. If you were to have three suggestions for people looking for purpose, maybe in the later part of their life, what could you pass on from your own experience? So you’re living your purpose now, in part anyway, by helping veterans.

Correct. I’m on the board of four veteran service organizations, and I support a couple of other ones. So, yeah, I have a passion to help veterans because they’ve given so much to our country. 

In fact, I have a little saying that I say to most of our veterans groups that I’ve been to, is that you as a veteran has given war to our country. When you look at yourself in the morning and shaving or looking at it in the mirror, you can look in there and know that you’ve given more to your country than you will ever take back. 

Because less than 1% of our population of 350 million people are in the military – less than 3 million people are on active or reserve component military. So less than 1% of our U S is serving in the military. 

They have given a lot for us. They’ve paid the price, and their families have paid the price. The soldiers that were killed and didn’t come back – they left families behind. They left wifes behind. So the family has to pick up him and move on without their loved one.

And what is the reward you get within yourself for supporting like that? I mean obviously there’s got to be the part that drives you to do it. So what’s the experience for you?

The experiences … I feel I’m at a point in my life where I can help people, give back in my community, give back to people that may have not had the advantage of having the experiences I had, and the ability to do things that I have. 

So sharing some of my experience in my past, and my support for those people in their community, can help them. 

And similarly, a lot of times if you have like PTSD issues, you go to the VA for example, and you talk to a therapist or somebody who is very trained and very versed at what they’re doing. But they don’t necessarily have had the same experiences – because they may not have even served in the military, for example. 

So having been there, done that, I can talk from experience. Not that I’m braggadocious, but I could talk similarly – almost like the same tribe. We’re from the same tribe, so we’ve had similar experiences. Your experiences will be different than mine, obviously, even if we did the same mission – we can relate to each other. So I guess people can relate to my experiences because I’ve done very similar experiences,

Been there, done that and I know the feeling. And when you reach out to somebody like that, it opens up a door for somebody. It brings some spaciousness and some light into a place of my own experience now that I’m passing on. But it gives hope. 

It’s so easy for people that have gone through a deep traumatic place to get constricted into a dark hole or a dark cage. And somebody that can open up the door and truly just let them be heard, give them a place to come outside of themselves. can be so powerful.

Right, right. And I know you mentioned in your prior talks about you worked it down to your bucket list, right? And your bucket list was kind of the turning point in your life where you have these things you want to accomplish. And your life is at a point where you’re not going to accomplish them with if you don’t continue on and go forward with that. So you add things to your bucket list.  It’s your kind of purpose in life. What do you want to accomplish in it?

It’s funny, it’s transformed too though. At first started it was like “do this so you don’t go checking out.” Right? 

But then the first one came off so well, you know, it was like where I got through the eye of the needle. It’s like, “Whoa, my God, what could I do with the second and third ones to make them even more than they were originally set to be?’ 

And the second one was about growth. And the third one is about giving, which is really what your life is about now. Right? 

So what’s your top three tips for people that are looking for purpose or seeking to give back now that maybe they’re in their golden years, or they’re at a point where they can do that?

I would say, from the basics, look after yourself, right? Because your body is the only place you’re ever going to live. So look after yourself mentally and physically, whatever it takes to keep yourself energized. Get enough sleep, eat the right foods. And be with people that you want to be with – because they have similar goals or expectations or similar themes to their life that you can attach yourself to and be part of. 

So keep yourself strong mentally, physically and emotionally, so that you have the energy and capacity to be with people, and be around people that have the same similar goals as you versus having friction all the time.

Okay, next one?

I would say that, kind of like you had said, have a list of things that you want to accomplish. You don’t have to say, you know, I’ve got to finish this by the end of the month. Or I can’t check it off my list because maybe it’ll take more than a month to accomplish. But have some things you want to accomplish in your life. They could be big or they could be small.

And then think about your legacy. When you’re not here anymore, what is your legacy going to be? What are people going to say about you, right? Are you going to leave a lasting impression of people? Are you going to motivate the generation behind you or the generations behind you? 

And they can look to you and say, Hey, Doug is, is a world-renowned author and adventurer. And he’s been around a lot of people, and he’s gleaned lessons for them that he can use and pass on to other people. 

So as we all have a purpose in life, and I think some of that purpose in life is to motivate and be an example – whether it’s bad or good. We get a lot of bad examples on TV from the news for example.

Yeah, don’t we! Especially right now.

On the other side of that, you can hang around people that are positive and energetic and have similar goals. Join organizations that you want to be part of, whether it’s “Save the Whales” or hug a tree. Whatever is passionate for you, do it and live to it.

All right. Anything else you want to add on?

I would say don’t go down life because your mother or father or your brother or friends say, “Hey, you’ve got these talents. I think you should exploit them.” Go from what’s in your heart and what passion that you really want to have. 

You might have a passion for journalism, or a passion for being in the military, or a passion to play football or basketball. And you might think, “Hey, that won’t be a career path that can put bread on the table and pay the rent.” 

But something will evolve out of that, that will be able to make you a richer person mentally, physically, and emotionally and financially – versus going to school to be an accountant because that’s going to put bread on the table and pay the rent for you. 

So live your life by the passion that’s in your heart, and not by what you think the job opportunities will be down the road. So form your life based on your passion, and not just necessarily what’s available out in the world today.

And what indicators do you have in your own life that when you know that you’re on track with your passion?

Good question. Well, you know you’re on track because you feel satisfied at the end of the day. You wake up in the morning with purpose. When you put your feet on the ground, you can say, “Oh, I’ve got to get out and accomplish these things today.” 

You’ve got a mental plan in your head of what you want to do that day – versus lying in bed and hitting the snooze again and again and saying, “Oh man, I got to go to the office today” or “I gotta go here today and think about that.” 

It’s a kind of energy field that you work on yourself mentally. It gets your focus and purpose of life.

All right, General Robert Hipwell, if, well, thanks very much for doing this interview with us. 

It’s an honor and privilege to talk with you, Doug. And all the success in your life in the future.

Thanks. And you too. 

Thank you!


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