October 27, 2025 • 53 mins
#187 - A childhood marked by chaos. A career built on service. And a second act shaped by faith, language, and a blank page. Jake sits down with Ken Webb to trace a life that refuses to settle for mere existence—from praying his way through a turbulent home to leading across Kosovo, Iraq, Afghanistan, and beyond.
Ken opens up about how his grandparents’ steady love and a lived-in faith helped him endure abuse and instability, and how those early lessons informed three decades in the Army Reserve. We walk through his pivot from military police to intelligence, the realities of early Iraq deployments, the nuance of embassy duty in Baghdad, and the complexity of retiring when your identity is wrapped in a uniform. Ken shares why he turned down comfortable contracts, chose Miraflores in Lima, and made Spanish class and the gym his new daily discipline.
We also dig into his debut novel, Trapped in Deception, a work of fiction threaded with real messages and real emotions. The story explores gaslighting, misplaced trust, and moral courage through a protagonist who—like Ken—keeps moving forward even when life tilts sideways. Along the way, Ken reframes adventure: not cliffs and bravado, but consistent growth, honest discomfort, and choices that expand your life. If you’re wrestling with what comes after a big chapter ends, or wondering how to trade drift for direction, this conversation offers practical hope and hard-won insight.
Listen, share with a friend who needs courage today, and if the story speaks to you, leave a quick rating or review. It helps more curious, purpose-driven listeners find the show.
To learn more about Ken and his first novel check out kenwebb69.com.
Want to be a guest on Journey with Jake? Send me a message on PodMatch, here: https://www.podmatch.com/hostdetailpreview/journeywithjake
Visit LandPirate.com to get your gear that has you, the adventurer, in mind. Use the code "Journey with Jake" to get an additional 15% off at check out.
Visit geneticinsights.co and use the code "DISCOVER25" to enjoy a sweet 25% off your first purchase.
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
SPEAKER_00 (00:00):
From a childhood filled with chaos to a career
(00:02):
spanning more than three decadesin the military, Ken Webb's
story is one of faith,resilience, and rediscovery.
Today on Journey with Jake, Kenopens up about the battles he's
faced, both on and off thefield, and how those experiences
shape the man he is today.
Now living in Peru, learningSpanish, and writing his first
novel, Ken shows us what itmeans to truly live with purpose
(00:25):
and not just exist.
This is an incredible journey ofcourage, healing, and adventure.
Welcome to Journey with Jake.
This is a podcast aboutadventure and how through our
adventures we can overcome thechallenges of life that come our
way.
While I expect you will learnsome things about different
adventures, this show willentertain you.
Each episode will featuredifferent guests or guests that
(00:46):
they share experiences andstories from the different
adventures they have been on.
Not only will you beentertained, but you will also
share the failures and trialsthat each guest faces what they
have done or are doing toovercome the hardships that come
their way.
My goal is to take each of us ona journey through the
experiences of my guests withthe hope that you'll be
entertained and inspired toovercome your day-to-day
(01:09):
challenges.
After all, stop the destination.
As my intro music fades, I justwant to welcome you once again
(01:32):
to Journey with Jake.
If you're new here, this iswhere we dive into the stories
of adventure, resilience, andthe purpose that shape who we
are.
Don't forget to follow along onInstagram at Journey with Jake
Podcast.
It's a great way to see thepersonal side of my own
adventures and stay up to datewith what's coming next.
Today's guest, Ken Webb, bringssuch an incredible mix of grit
(01:52):
and grace to a story.
From a difficult childhood toover 30 years of service in the
military, Ken's life has beenabout overcoming obstacles,
trusting his faith, andcontinuing to grow, even now as
he lives in Peru, learningSpanish and writing his first
novel.
And if you enjoyed thisconversation, be sure to go back
and listen to bonus episode 10with Special Forces Operator
(02:13):
Chris Brewer, another powerfulstory about courage, purpose,
and the call to adventure.
All right, let's get into itwith Ken Webb.
Another episode of Journey withJake is here, and I've got Ken
Webb joining me.
Ken, welcome to Journey withJake.
SPEAKER_01 (02:26):
Thanks for having me, Jake.
SPEAKER_00 (02:27):
Yeah, I'm excited to talk to you.
I read a little bit about yourbackground and kind of what
you've done.
You've spent a lot of time inthe military.
It was a big part of your lifeand who you are, but also your
childhood was something that wasa little bit different.
And before we talk about yourmilitary career and what you've
got going on now, I'd like to goback and what was it like
growing up in a home marked bytrauma and chaos in your mind?
SPEAKER_01 (02:49):
I mean, it was difficult.
I mean, I'm a Christian.
I did a lot of praying.
You know, I was raised mostly bymy uh maternal grandparents,
meaning the mother and father ofmy my mother, but then my mother
was married five times, and andyou know, like with step uh
father and and stepbrothers,there's always difficulty,
(03:11):
always tension in there, andsometimes I bounce back and
forth between homes.
It was very difficult.
It was very difficult for me.
And it was in the 70s because Iwas born at 69.
People didn't understand as muchabout children at that time.
And and I mean I mean I'm sureit was probably better than it
was like in the 1940s, 50s, or60s, but my experience, and you
(03:35):
know, at that time we were justgetting out of the phase where
children were supposed to beseen and not heard.
So, you know, you have anytrauma, you just kind of suffer
in silence.
I really am very fortunate formy grandparents.
I'm referring to my mother'sparents because they they did uh
they were a sort of like ananchor for me.
You know, through them, my mygrandfather was a very good
Christian, and and mygrandmother was a a Christian
(03:58):
also, not as outspoken about it,but I I uh have to give them
credit for being like my rock.
Whereabouts did you grow up?
I grew up outside of SouthPhiladelphia, a town called
Collingdale,C-O-L-L-I-N-G-D-A-L-E.
It's about I guess about twomiles, maybe two and a half
miles, uh straight line distancefrom the Philadelphia airport.
(04:21):
And to give people an idea, ifyou you've flown in, there's but
it's not this isn't a huge town,and I don't know anybody famous
from there.
But it's it's in DelawareCounty.
It's not in Delaware, but it'sin Delaware County.
And it's it's next to SharonHill, uh, you know, Upper Darby,
Springfield, those kind oftowns.
Yeah, it's a lower income town.
(04:43):
I think it was a nicer, it'salso where my my mother grew up,
so it's uh it was a nicerneighborhood at that time.
SPEAKER_00 (04:49):
Well, so it sounds like your grandparents were a
huge influence on you for thegood, which was nice to hear.
You talked about you talkedabout being a Christian.
That's something you just kindof grew up with because you
talked about praying a lot.
Talk about your faith a littlebit.
SPEAKER_01 (05:02):
Well, I mean, I'm not one of these people that you
know they say you have to know aspecific time when you became a
Christian.
I I I used to tell people when Iwas 13 years old, because then I
I did the sinner's prayer.
I was in a in a place of prayermeeting and did the sinner's
prayer, but I I don't believethat.
I mean, if you you look in theBible, it doesn't say you have
(05:23):
to like say a specific prayer.
That's that's just somethingthat people do, and I believed
before then.
So I I think it was before that,I don't know exactly when, but I
mean, growing up, at least withmy grandparents, my my
grandfather always went tochurch.
Now, something interesting, mymy grandmother did not.
He lived right around the cornerfrom the church.
She would prepare breakfast andlunch and everything like that,
(05:44):
very traditional, you know,husband and wife.
She never learned to drive.
Uh, she worked up until they hadkids, and then she didn't work.
Her job was to take care of thekids, but she kept the house
spotless and always cooked andcleaned, did everybody's
laundry.
You know, her adult kids, shewanted to do their laundry, you
know, bring your laundry, I'lldo it.
And only my uncle did that.
The the two sisters did not.
(06:05):
But uh I went to Sunday school,but in my case, at least, I
don't think this was from thechurch.
I think this was just mygrandfather.
It was a reformed Episcopalianchurch, which falls under the
Anglican.
It's very different thanEpiscopalian.
It's very uh Episcopalian hasbecome very liberal.
This reformed Episcopalian isstill very conservative, but I
didn't actually attend churchuntil I was confirmed into the
(06:26):
church, and that was at at theage of uh 13.
Then when I moved down to Texasto be with my mother, I uh after
her third divorce, or during herthird divorce, I started going
to a Baptist church.
Uh, but now I've moved back.
Down here in Peru, I go to anAnglican church, and it is a
conservative Anglican church.
I really I believe more uh alongthose lines.
(06:46):
I mean, if if you're aChristian, you're a Christian.
But uh I I just when I read andstudy, I'm more along lines with
that.
Um I'm not I'm not seeing peoplein the Bible that were
prohibited from drinkingalcohol.
Jesus drank alcohol, and therewas wine available in those days
that was non-alcoholic.
There was grape juice that wasavailable, and yet he drank the
(07:08):
alcoholic kind.
But some Baptists, some otherdenominations will tell you, you
know, you can't dance.
Well, people danced in theBible.
I mean, I guess there's a fullspectrum.
There are different kinds ofdancing, different ways you can
dress when you dance.
I think instead of gettinginvolved in legalism or legalism
thing, I think God is much moreconcerned with our relationship
with Him than in how we dress oreven in what we do.
(07:32):
Our relationship with Him isactually more important.
So yeah, it was I I prayed a lotthrough some of those tough
times.
I do feel I was deliveredthrough a lot of that.
Uh I didn't witness any likemiracles, but you know, things
that just like when thepercentages were very much that
you know something should havegone the wrong way, and it
through a lot of prayer it wentthe right way.
I I give God that credit.
SPEAKER_00 (07:54):
Was it growing up, was it like abuse and things
like that?
Was it just instability?
You know, your mom's gettingdivorced a bunch of times.
Kind of all of the above?
Is that what was going on?
SPEAKER_01 (08:04):
Uh there was some abuse.
There was some uh sexual abusefrom sexual abuse from a
stepbrother.
That was the only person thatwas sexual abuse.
My mother, it was some, I mean,I I mean the times change, but
there was verbal abuse,psychological abuse, even from
my mother, definitely from mystepfather.
Stepfathers, actually.
My mother died in uh July the30th, 2024.
(08:27):
My stepfather just died thisyear.
He had dementia.
He was in a nursing home.
I I can't say he was reallyabusive.
He was maybe narcissistic,especially in the end, but I he
wasn't really an abusive person,and he was never abusive
physically with my mother.
He might have played some gameswith her, but yeah, I know my
(08:48):
mother was married, her secondhusband was a pathological liar.
He was a salesman.
My mother was divorced from hersecond husband.
Uh, I guess I must have beenfour years old, something like
that, so I don't remember him.
There was no physical, sexual,psychological abuse.
SPEAKER_00 (09:04):
I know you've spent a big part of your career in the
military, but I I you know,thinking back to those early
days and the struggles you wentthrough, do you feel it helped
prepare you for your you knowthe struggles you'd face later,
like in combat and being in themilitary?
SPEAKER_01 (09:17):
I I think there are many ways, you know, to prepare
for something.
I think it did, but I I don'twant to give somebody the
impression that it prepared mebetter than so you know other
things.
You can you can learn you canlearn not to you know burn your
hand by sticking it in the fireby listening to common sense and
observing, or you could stickyour hand in the fire.
(09:37):
That doesn't mean sticking yourhand in the fire is is the best
way to do it.
So I I think it did.
It it helped me because some ofthese issues and things I ran
into in the military seemed verylittle compared to uh you know
what I had faced as a child, andand they weren't like life and
death situations as a child, butit was something where like I
was, you know, you're a child.
(09:59):
You don't have control, youdon't have money, you can't just
get up and say, Well, I'm gonnalive over here, or no, I'm not
gonna do that.
I'm not gonna obey your rules.
You just can't do that whenyou're a child.
SPEAKER_00 (10:10):
When you look back at that childhood, is there a
lesson that you've carriedthroughout your life that you
learned as a child?
SPEAKER_01 (10:16):
What I learned from that, and I I mean I I mean
anybody can get the right answeron a test, and they say, Don't
steal, don't do this, don't lie,don't use bad language, but then
following through and do it,that's another.
I mean, none of us would eatjunk food or anything.
We all know it's bad for us, butwe do it.
Uh, one thing I I I try to takefrom that is, you know, to to
(10:38):
face your demons, to deal withyour problems.
You know, to take care of thingsuh not just during this life,
but you know, before you die,get a will, make sure
everything's taken care of.
Don't leave everybody with amess, be responsible.
Everything I've read, whenpeople get older, they're mostly
bothered by not the things theydid, but the things they did not
(11:00):
do.
So, you know, chase your dreams.
That's what I'm doing down herein Peru.
I'm I'm gonna I could haveworked as a contractor, I was
making good money, and Idecided, you know what, people,
I'm 56, people my age are dying,cancer, stroke, everything else.
I I'm gonna do what I want todo.
Uh, I do not believe with amentality of sitting in front of
(11:21):
the television.
I didn't retire early so I couldwatch television.
You know, I go to the gym, I Iread a lot, I'm learning
Spanish, uh, writing my firstnovel.
I I'm gonna work on mydoctorate.
I want to do it online so Icontinue, I can continue to live
down here and and to continue tolearn Spanish.
SPEAKER_00 (11:41):
You're talking about, you know, living,
actually living and not justkind of going through life,
which I like to hear.
And this is podcast that's allabout that.
It's an adventure podcast.
For you, and usually I kind ofdo this at the end of my show.
I want to do it right nowbecause we're kind of jumping
into things that you're doing.
What does adventure mean to you?
SPEAKER_01 (12:28):
Well, adventure to me, I mean, I'm I am not an
adrenaline job.
I'm afraid of height.
You know, they have this thingover the cliffs here where you
get on like a parachute.
It's not a parachute, it's likea paragliding type thing with an
engine.
As somebody will go with you,and then they'll take you out,
and people are saying, oh no,it's safe, it's safe, it's safe.
And I said, Yeah, but you haveto sign a disclosure for that,
don't you?
About if you get dismembered ordie.
(12:50):
I said, I don't have to do thatat the school I go to.
So there is some danger there.
You know, you're you're you'rethere there is some danger that
they're just not admitting to ordon't want to think about, or
they just don't care.
And I'm I'm not a drink, I amafraid of heights.
I was, you know, I took flyinglessons.
I the only thing I couldn't dowas solo, and that's because I
was afraid.
So, but adventure to me is notonly putting yourself in
(13:12):
physical danger.
Now, I am a big scuba diver, bythe way.
Ironically, depths don't botherme.
It's the heights, it's the otherway.
So yeah, and adventure to me isgoing out trying something new,
pushing yourself.
Ask my teacher, you know, shouldI continue with two hours a day
on Spanish or go to four when mybook is done?
She thinks two hours a day, theone teacher said the other
(13:34):
teacher said four.
I think in order for you toimprove at something, whether
that's going to the gym or orrunning or anything else, you
have to push yourself a littlebit.
You have to, if you'recomfortable, if you're if you're
just lifting weights enough andyou're you're never sore
afterwards, you're not doing agood job.
You need to push yourself alittle bit.
So I need to be a littleuncomfortable and it needs to be
(13:55):
a little bit inconvenient, orI'm not maybe inconvenient isn't
the right word, but it needs tobe a little bit of a strain on
me, just like whether that'sphysical or or mental.
And I'm not saying like, I mean,some of these Japanese students
go because their companies sendthem eight hours a day and
they're like sleeping in class.
So I don't mean like that.
Uh I don't mean push yourself inthe gym until you're in pain and
(14:16):
you injure yourself.
But you know, uh to me, anadventure is getting out, trying
something new, traveling, notbeing stupid with your money,
but not going with the idea thatyou're gonna die with all your
money.
You don't want to be the richestperson in the graveyard.
But you all you also don't wantto be the poorest person in the
graveyard, you don't want to diestruggling for money.
SPEAKER_00 (14:36):
Yeah, it's finding that right balance for sure.
I appreciate that.
So I know you spent over 30years in the military.
Why the military?
What got you into the military?
You always wanted to do it, itwas something you'd looked up to
as a kid.
Why'd you get in the military?
Uh you're exactly correct.
The answer would be yes to that.
SPEAKER_01 (14:51):
Okay, but I always knew I wanted to be in the
military.
I wasn't sure.
Never really thought I wanted tobe in the Air Force, but I I I
never really thought I wanted tobe in the Marine Corps, but I
was like Army or Navy, somethinglike that.
And I knew Army was big and theyyou could live in many different
places.
Navy was always kind of neat.
I love the water.
But I was at a junior collegeone day, saw somebody I'd gone
(15:15):
to high school with, he was in amilitary uniform.
And I I said, you know what,people don't normally wear
military uniforms with boots andand the hat and everything.
I mean, I was like, so what'sgoing on here?
And he and I weren't reallyfriends, we were just we just
kind of knew each other.
He was an acquaintance, and hethere he was in the ROTC
program.
So that summer I went went tobasic training and and uh was
(15:40):
enlisted for a little while andthen I got commissioned through
the University of Texas inArlington, and and then I was
commissioned as a militarypolice officer, but I was in the
Army reserves.
This was in 1992, it was afterthe Gulf War, and military was
being downsized.
So when you're a reservist,well, you if you're not gonna
continue education, which I Itried getting a master's degree
(16:02):
immediately after my bachelor's,it didn't work out.
But if you're not gonna do that,then you need to get a civilian
job as well.
So I had various civilian jobs.
I taught English for a year.
Uh I was not certified, but Itaught it for a year as a as a
substitute at uh Arlington HighSchool in Arlington, Texas, 11th
grade English.
(16:22):
Worked for a friend's businessfor a while.
We're working uh not, it wasn'tI I call it technical writing,
but really it was just morewriting manual stuff for a
company.
It wasn't that technical.
And then I got a job withAmerican Airlines, and I was
just working in reservations atAmerican Airlines.
I uh was uh a captain in theArmy Reserves, and uh there was
(16:45):
this tour, these active dutytours.
So you have these reservatorswho go one week a month, two
weeks in the summer.
Sometimes they go two weekends amonth, but you can go on active
duty for a while.
And there was this tour in inKosovo and started on the 15th
of April 2001, and I was a forceprotection officer, and I was in
Kosovo on 9-11, and I was inPristina, Kosovo, and everything
(17:09):
went down on lockdown.
And at that time, due to youknow, troops being deployed and
you know, wartime operations, ifthat's the right word, combat
operations, a lot of the pursesprings, uh purse strings were
open and people were mobilizedvoluntarily and involuntarily.
American Airlines changed itspolicies from being mobilized
(17:31):
five years to as long as troopsare deployed, which is
technically, I think, still thecase now.
But I would just mobilize andI'd go on one tour after
another, you know, look atsomething neat, estate,
eventually transfer it over tomilitary intelligence, you know,
was what I wanted to do.
And uh I had a scholarship, bythe way, for my bachelor's
degree.
So then on my master's, I useduh tuition assistance, which
(17:54):
paid for most of my.
I went to American MilitaryUniversity, which is entirely
online, and I used a smallamount of my GI Bill when that
would when the tuitionassistance was put on hold for a
while.
So instead of 36 months, I have34 months left.
I want to pursue my doctorate,and I have no idea what I'll do
with it.
I want to do it in intelligence,unclassified, of course.
It's all the classes will all beunclassified, and it's I don't
(18:18):
know if I'll do anything withit, but it's it's a personal
goal.
SPEAKER_00 (18:22):
I think we all have to have goals.
I like that.
Yeah, even though you may notwant to do anything with it, who
knows or what you'll do with it,you have that goal.
I like the fact that you havethat goal.
So all these tours, you startedKosovo.
Where else did you serve?
Like what what other tours, ifyou can tell?
SPEAKER_01 (18:36):
After Kosovo, I went to Joint Task Force Six, which
is Joint Task Force South.
Now, of course, for thosemembers who are in the reserves
or National Guard, there'ssomething called the Soldiers
Sailors Act.
And that gives you, and thingsmay have changed because I've
been retired a few years, butgave you 90 days to return to
work after that.
So I went to Joint Task ForceSix, which is now Joint Task
(19:00):
Force South.
It's uh it's a counter-drug,counter-nar narcotics on the
border.
And it was the border of Texas,it was in El Paso, New Mexico.
I don't think did we go inCalifornia?
I don't think I ever went toCalifornia with them.
And it was, you know, in I wasstill military police at that
time and had some Intel peoplewith me.
We would be in civilian clothesand do assessments of the
(19:22):
border, and and we weren'ttrying to stop people from
coming in illegals, but we weretrying to stop drug trafficking
there.
But it wasn't stopping it withfirearms.
We weren't carrying firearms.
It was to do an assessment, whatthings we could do.
We had some counterintelligencepeople working for us, with us,
not for us, but to to to lowerthat.
(19:43):
So then after that, let's see,the 2002, well, 2003, I went to
Iraq.
And I was actually, nope, I takeit back.
I take it back.
I went to the Joint AnalysisCenter, Joint Analysis Center in
Molesworth, England.
I joined it, I was there forseven months, and then I bought
(20:05):
an around the world ticket.
I was going to go back to workat American Airlines, but I had
three months, and I wastraveling around the world.
I was in Thailand.
I was on a scuba diving boat.
I got off the boat, checked myemail.
There's no WhatsApp or anythingthen.
Check my email.
This was in in 200 in two, inDecember.
It may have been, it may havebeen 2003.
(20:27):
It was 2003, early January.
Early January, because I did NewYear's in Tokyo.
I got an email, you know, returnto the United States
immediately.
We've been mobilized.
I contacted my Army Reserveunit.
I said, look, uh I'm I'm a scubadiver.
I've been scuba diving for threedays.
I can't get on a plane for 24hours.
I'll get decompression sickness.
So they said, as soon as youcan, come back.
(20:49):
So I did.
We did a convoy from GrandPrairie, Texas down to Fort
Hood.
And this was like duringOperation Iraqi Freedom.
So this was before they got realorganized with the stuff.
So after this, they they got towhere people would go in and do
their medical stuff throughoutthe year and prepare.
But we had people going through,you know, one guy had like six
(21:11):
teeth pulled.
There were some people got a lotof shots, and then they they got
better with this afterwards towhere people were getting shots,
but they were always ready todeploy.
But in the beginning, it was areal mess.
I went over there, I was abattle captain working under the
operations officer of the S3,and then I eventually became a
company commander because Ihadn't had a company command
(21:31):
yet.
Uh we returned to the UnitedStates.
I went back to being a you knowa weekend warrior for a while.
And then I did branch transferto military intelligence, went
to Fort Wachuca, which is whereI transitioned to it's in
Arizona to militaryintelligence.
I guess it's about an hour, Ithink it's about an hour, maybe
(21:53):
a little bit more from TucsonDrive, and it's it's not
terribly far from the borderitself.
Was up there for just about justunder three years, 33 months.
I remember that.
And then my new reserve unit gotmobilized.
We went to Afghanistan.
I went there in in 2009, butbefore this, we had a train up.
Went arrived, I guess it wasOctober 2009 and left August
(22:17):
2010.
I I did a very short tour, Imean like 60 days, to Stuttgart,
Germany, support of operation, Ithink it was New Dawn.
Can't remember the name of itvery well.
And we were counting airstrikes,and that was just because I had
the right clearance.
I had a top secret clearance.
There was nothing glorious aboutthat.
(22:38):
Came back, was then at up atFort Sill with the 75th Training
Division, training NationalGuard and Reserve members before
they went overseas to Iraq,mostly Iraq or Afghanistan, also
some nations in Honduras,training them to, you know,
making sure maybe instead oftraining them, there was some
training, but maybe it's moreaccurate to say assessing them
(23:01):
to see that they were ready togo, getting them up the speed
for that.
And as a unit as a whole, not asindividuals.
And then I did that same thingdown at Fort Hood, Texas.
And I did that about threeyears.
And then I went to GuantanamoBay, Cuba.
I was running some contracts outthere specifically with
linguists for languageinterpretation, working
(23:23):
alongside of interrogators, butI was not an interrogator.
I was not running interrogators,I was just running the
linguists.
I was out there for 18 months,got a tour going to Germany.
It was in logistics.
I had an additional skillidentifier in logistics, but it
was very hard for me because mybackground was military, police,
and intelligence.
And I people helped me and Istruggled through it.
(23:44):
And then I got to work back inintel, and I did that for a
year, and then I did not thatwas in Kaiserslaughter, Germany.
And then I did nine months inStuttgart again and enjoyed both
places or advantages to bothplaces.
Return from that.
Of course, in between all thesetours, I would go on trips and
scuba dive and travel.
(24:05):
And I had a great time, really.
It was stressful.
Trying to piece together thesetours can be very stressful
because there's time limits thatyou can be mobilized.
And when you reach that timelimit of being mobilized, used
to be three years, now it's goneto four, I think.
But then what you have to do isyou have to deploy, and that
resets your clock.
And deploying meaning going toIraq or Afghanistan.
(24:27):
Sometimes Kuwait, I think, butnow I don't I don't know if
Kuwait does it or not.
But then after that, I was outin intelligence role, a special
access program, but in anintelligence role more
administrative, out at CentralCommand at McDill Air Force Base
in Tampa, Florida.
And was out there about 15months and then went out to
(24:50):
Kosovo.
Uh uh, not Kosovo, went to CampBon Steel.
Not Camp Bon Steel, that isKosovo.
Went to Camp Arafgan in Kuwait.
And I was there just uh, I guessabout a year, and I was kind of
like the a mayor of this campfor a lot of intel people out
there, to make sure the lightswere on, make sure everything
was good, listening to theircomplaints and trying to make
(25:13):
things happen.
And then, believe it or not, itwas during the height of COVID.
This was 2019.
I remember in like, I think itmight have been November, I
started hearing whispers aboutthis COVID thing, and then a lot
of us thought it would just dieout.
So it was like by August, thiswhole thing will be dead.
December, it got really serious.
January, you know, people werewearing masks and all kinds of
(25:36):
lockdown.
My retirement date was in uh wassupposed to be June of 2020, and
I returned to the United States,went down to a good friend's
house down in Harlington, Texasto sit out the COVID, you know,
the waiting period ofquarantine, and did actually
retire, and then three dayslater got an email that said,
uh, so much of your retirement,you know, because I was an Intel
(25:59):
officer, Intel intelligence,along with other branches, they
were they were uh extendedanother two years for me to try
to make, I was a lieutenantcolonel, full colonel.
But the the dig about that wasto make full colonel, I had to
get a battalion command.
I had to get in charge of abattalion command.
And when I went to go do this,they said we have to have two
(26:22):
years left to get a battalioncommand.
And at that point, I'd only beenextended two years and I got
late notice, so I couldn't.
So what did I do?
I started looking for anothertour.
The stuff in the system wasshowing me already retired, so I
had to go about getting thatcorrected.
A lot of manual stuff.
I wound up going out to theUnited States Embassy, Baghdad,
Iraq.
(26:42):
My second time Iraq, this time Iwas on a diplomatic mission
under the Department of State,which meant for the first time
in my military career, I had toget a visa to go there.
I wasn't allowed to carry aweapon.
I wasn't allowed to do anythingmilitarily wise.
It was, you know, staying on thebase a lot.
We could wear our militaryuniforms sometimes.
(27:03):
Most of the time, we worecivilian clothes, and I was the
chief of operations, which isnot a job for an intelligence
officer.
That's a job for infantry, or ifyou're Air Force, a pilot, or
Navy, maybe a pilot, or or orsubmariner, or something more,
you know, macho on those lines.
So that that was that was aninteresting learning curve for
(27:24):
me.
And then that that took methrough September of 2021, and
there wasn't really opportunityfor another tour.
So I I did do the contractingroute after that.
I was actually with my leave,which is vacation I'd
accumulated.
I was on active duty statusuntil close, like close to the
(27:45):
end of October.
So then I went back to Kuwaitand I did it as a contractor.
And I was still in the ArmyReserves at that time, but I
went from being a lieutenantcolonel with my own office and
everything else to just being,hey, we need some help over
here.
Come over here at Ken.
I went to being Ken fromLieutenant Colonel Webb to Ken
or Sir to Ken.
(28:06):
This particular contract, Ididn't like it a whole lot.
I mean, there's a lot of verygood contractors out there, a
lot of very good contracts.
I felt like uh people wereabusing some of their
privileges.
You know, you got to live offthe base and and things going on
that I didn't like.
My mother was taking care of mystepfather.
He had dementia at that point.
(28:26):
She said, I need you to come offthat contract and come help me.
And so I I did.
And we got him under control,and I found another contract,
and I was going down.
I came down here to Peru.
My best friend had stage fourcancer, so I came down here, was
spending time with her.
I did the four-day Inca trail toMachu Picchu.
(28:49):
I was waiting on anothercontract, as I stated, and then
when after three months, theycalled me and I said, You guys
didn't give me any updates, andI had to go back to the U.S.
to go through a medicalscreening.
And that whole process they'regoing to have me go through
could take up to a year, andthey weren't going to pay me
during that time.
So down here where I'm living atin the Miraflores district of
(29:10):
Lima, Peru, I'm by the ocean,and it it's like living in in
maybe Santa Barbara somewhere inCalifornia.
I mean, we're talking Californiaterms.
I've never lived there, but it'sprobably probably like
one-fourth the cost.
Maybe one-fifth, depending.
And I was learning Spanish, Iwas liking what I was doing.
People my age, three people Iweren't, I wasn't friends with
(29:34):
them, but I knew them.
They died of cancer, and otherone died uh from a heart attack,
and I was like, I this isn't forme.
And the the contract that I wasbeing looked at was to go to a
top secret facility over inAustralia.
I'd be working in a buildingwith no windows, which is not a
normal that's normal for thattype of job.
(29:55):
But I'd be working 12-hourshifts, uh 12 noon to midnight
for two days, and then midnightto noon for two days, and then
four days off.
And it was at a place calledPine Gap near Ayers Rock, near
Ayers Rock, and it wasunbearable heat.
And I it wasn't like like goingto someplace really nice.
(30:17):
I've been to Australia beforeonce for about twenty twenty one
days or twenty three days,something like that.
Did a lot of scuba diving there,and this was not in in Perth or
or someplace that that you you'dwant to really go to.
And and stay at.
So I that is how I wound up.
But my mother got sick lastyear, so I had to return to the
U.S.
(30:38):
I was on a student visa downhere, which is hard to get.
And then after she died, I hadto, I'm her only child.
I had to take care of herestate.
My stepfather was in a home forpeople with dementia.
I had to take care of that.
And I was uh out of thiscountry, meaning Peru, for nine
months and then returned the17th of April, 2025.
SPEAKER_00 (30:58):
And now you're in Peru, living in Peru, along the
way.
Were you ever married oranything like that, or no?
SPEAKER_01 (31:04):
I've never been married, no kids.
I've never really wanted to havekids.
I think that has something to dowith difficulties I had growing
up.
I feel like I want to enjoy mylife.
And now I'm 56, and I I meanpeople do it, but I to me I
think it's off the table.
I mean, I I think, you know, ifyou're going to have kids,
that's great.
I don't know.
I mean, my mother passed away at77.
(31:26):
I mean, you I I I wouldn't wantto have a kid and then I don't
make it to his high schoolgraduation because I'm dead or
something.
I don't I don't know.
I mean, her father lived to be93, and her mother, who chained
smoke, well, she smoked twopacks a day for decades, lived
to be 88.
So, I mean, and my mother smokedone cigarette in her whole life,
(31:48):
so I I can't we we just don'tknow.
And I have never been I I wouldlike to get married someday.
Okay, so you are interested inthat part of it at least.
I think so.
My mother was married fivetimes, so I told people she took
my turn.
SPEAKER_00 (32:04):
She took advantage of it for you.
So, as far as you know, leavingAmerican Airlines, leaving these
contract jobs, going to Peru,why did you decide to do that?
I mean, do you at least becausethe other thing you had
stability, you know, it's kindof a it's sort of a risk, you
know, kind of leaving thatstability behind.
SPEAKER_01 (32:22):
I I have to be fair, other people have said things
along similar lines.
I have to be clear.
It used to, I mean, theretirement age for an army
reservist is 60 years old.
So when you go on these activedeployments in support of combat
operations, you can take a youwill take a year off that age.
And you have to be a reservistdoing that.
(32:44):
You can't be on active dutydoing that, a regular active
duty soldier.
So I got my age down to when Iretired, I immediately started
getting my pension.
Now the Army Reserve andNational Guard retirement is
based on points.
I had enough points that myretirement pension was the same
as someone who would have beenon active duty who was in for 20
(33:05):
years.
I have a whole lot of points.
Also, I did retire from AmericanAirlines.
I didn't mention that, but theyoffered an early retirement in
2020.
And you you had to be like, Ithink I was 45 years old, and I
I was like 50 or 51, 51.
I met, and they you know gaveyou a bunch of uh flight
(33:26):
coupons, and I haven't startedreceiving my pension yet.
I was 55 up to 60 is when I haveto take it, but it's at a
reduced amount, and I'm I'mdebating about whether to start
taking it.
But what I'm trying to say isthe risk maybe not as high if
you have a pension.
It's not as high a pension.
I mean, some of these peoplethat great adventurers or some
(33:47):
of these people that go in therelike they're going to take over
the world.
I I don't I was gonna say DonaldTrump, but then he's so
controversial, I don't want tosay that.
But some of these people, thethe thing in common that a lot
of these people have, well,including him, but uh there's
many other good examples.
These people have families witha lot of money.
I mean, if if something, iftheir business venture fails,
(34:10):
they're they're gonna be okay.
And I know that I have a pensionnow and I've been saving my
whole life, so I'm able to.
Good.
So you have the means.
And I don't have kids.
So I mean, I I spoke to myfinancial advisor today.
He's a little bit younger thanme, but he has two kids, and one
of them is a junior in highschool.
(34:31):
So I mean, that's a big I try tobe charitable, but I haven't
given the kind of money thatpeople should spend on their
children if they have it.
I could have gone tocontracting, still got my
pension, but there comes a pointwhere that, unless you love
doing that.
I mean, you get someone who'slike an actor or musician or
something.
I mean, some of these people areincredibly wealthy.
(34:52):
I don't think they're hopefullythey're not doing it for the
money anymore.
They're doing it because it's anart to them.
There's nothing wrong withmaking money.
SPEAKER_00 (35:01):
You know, if it's you need to be doing it because
you love doing it.
Speaking of loving what you'redoing, I know you love being in
Peru.
You've also You mentioned you'rewriting a novel.
Tell them tell us a little bitabout the novel and what that's
all about and why did you decideto write it?
SPEAKER_01 (35:18):
Well, you know, it's it's really this language school
I go to down here is named ElSol, and Soul is the name for
Sun, S-O-L in Spanish, the Sun.
The teachers down here have beena positive influence on me.
I I came down here saying I wasgoing to study Spanish and I was
going to study French and I wasgoing to, it's before my mother
got sick, and I was going to getmy PhD and then write a book.
(35:41):
I spoke to some of the teachers,and the one teacher, you know,
she said, Well, why do you wantto learn French?
Do you want to live in France?
And there's nothing bad aboutlearning French, but it's not a
world language like it was along time ago.
It's like, well, why are yougoing to do that?
There should be a reason thatyou're doing that.
You know, in high school, youelect a language you're going to
(36:01):
take, but I mean, so you have totake something.
So yeah, sure, take, but Spanishis very practical.
So I actually took that, Ithought about that that night,
and I was like, you know what?
Her name is Isabel.
I said, she's right.
Isabel, you're right.
I told her the next day.
Speaking to one of my teachers,I actually spoke to him today,
and his name is Romeo, and he'shis mother is uh Italian, so
(36:24):
he's he speaks some Italian, hestudied it down here, and he he
spent uh two years at in twodifferent one year and then uh
come back for another year inEngland studying English, so he
speaks very good English, and hesaid, Well, is your book about
your PhD?
Is it about your doctorate?
And I said, No, and he said,Then why do you have to wait to
write it?
(36:45):
Why you you don't have kids,you're you're not married,
you're you're not working, whywrite it, start it?
And that was in August of 2023.
I took a break of about sevenmonths when my mother died and
started again on it before Icame back here.
So in and all in all, I've I'vespent, I mean, it it'll be right
(37:06):
a year and a half to write it,maybe two years, a little bit
less, I guess.
I started writing it because itwas therapeutic for me.
You know, I had uh I'm a verytrusting person.
I'm a very uh you know, I I hidemy emotions, but I'm actually
very emotional.
And, you know, if I'm a friendwith somebody, I put a lot of
trust in them.
And the Trapped the Deception isa work of fiction.
(37:30):
However, there is so much realstuff in that book.
I mean, all the texts, all theemails that are in the book were
taken from real texts and realemails, changing only the names,
the dates, locations, times.
And, you know, I had a friendwho really betrayed me, and he
(37:52):
is not, I won't say apathological liar.
I'm no psychologist, buteverything I know about
pathological liars, they lieeven when they don't have to
lie.
Things can be going their way,completely going their way.
No reason to lie.
They're still gonna lie.
He's not like that.
He's much more dangerous becauseyou're gonna catch somebody who
lies constantly.
(38:12):
He's he's a very smooth talker.
Uh, I worked for him for a whileafter I graduated university,
and he was a salesman of sorts.
He became a school teacher, andthen he's he's in real estate
now, and I was the best man athis wedding.
But I realized he was somanipulative and so like a I
(38:33):
don't know what you'd say, uhemotional or even more than
emotion, just a person who wouldjust you know suck you dry if
they could.
You know, just use you and useyou and use you.
I I I have him the bad person inmy novel is modeled after him.
And it is not, I mean, in thenovel, he's a a much worse
(38:55):
person than this former friendof mine.
In the novel, I mean, he's amurderer, he's a drug addict,
he's he's he's really bad.
But it's it's based on, youknow, like a lot of these
movies, you know, that's basedon reality, they could be very
loosely based.
But this is is more, I mean, hischaracteristics, this idea of
gaslighting, which as I foundout, gaslighting is based off of
(39:17):
a movie by the same name, veryold movie, where you know,
you're just well, wait, I didn'tsay that.
And the very next day, well, youknow, you must have me confused
with somebody else.
I never said that.
Never taking responsibility forown actions and and consequently
maybe never feeling guilt.
Maybe being a sociopath.
(39:38):
Emotion that I have seen fromhim is anger when he's caught in
his lies, or when you don't buyinto them, when you don't pay
attention to him.
The good person in the book isbased loosely on me.
The good person in the book isnamed Eddie, and he is a
computer expert, which I amdefinitely not.
But, you know, I needed I neededsomething, you know, in the
(39:59):
novel, you need to base it onsomething, on someone.
It's loosely based on me, atleast as far as the his
behaviors and his relationshipto the bad person in the novel.
Eddie was an intelligenceofficer in the Army Reserves,
and he was in Kosovo, Iraq, andAfghanistan the same times I was
there.
(40:19):
So I'm not, you know, I was onthis one podcast and and people
was alive, and people were ableto put in questions while it was
going on.
You know, they're like, well,did you give away any, you know,
operational information?
Well, none no, I didn't.
Nothing I talked about reallyhappened as far as
(40:39):
operationally.
The novel, Eddie is uh out inAfghanistan and they're chasing
a Taliban commander.
You know, I I never did that.
Uh so but he gets credited forkilling the Taliban commander,
which I don't want to give awaytoo much, but it's it's like an
accident.
You know, like a I'll go aheadand say it's a discharge of a
(41:02):
weapon, and so he should havegotten reprimanded for it, but
he was running with his pistol,you know, and he was like, wow,
that was a great shot.
Well, he he killed him byaccident, complete accident.
He tripped into things.
How that does parallel my life,I kind of alluded to this
earlier.
I just kind of tripped intothings.
Peru is an excellent place tostudy Spanish.
(41:23):
I didn't choose it this way.
I was up in Cajamarca on a tripup there and wanted to go down
to Oxapampa, which is a Germansettlement.
I had to go through Lima.
The president had gotten introuble and was actually put in
jail at Peru.
This was back, I think it was2022, and I I couldn't go any
(41:45):
farther than Lima.
And I was like, well, I'm notjust gonna watch television, I
can do that in the UnitedStates.
I'm gonna do something.
So I started looking at Spanishschools.
I said, I'm gonna study Spanishagain.
I I just tripped into sometimesinto these things.
And I I do think that's God.
I do think that's God.
It's like because when Iespecially, I told you I retired
(42:07):
twice.
In 2020, I went through extremedepression.
I didn't want to retire.
My identity, I identified myselfas a lieutenant colonel in the
army, even though I was areservist.
I was always on active duty.
I was mobilizing, and it waslike taking away my, I guess,
away my identity, my persona.
I I've heard mostly this is fromI've never been married, but you
(42:30):
know, like women when they getdivorced, you know, it's so it's
harder on them, I've heard,because they take on the name of
their husbands.
So then it's like, well, nowyou're losing that, you're
separating from that that you'vetaken on.
And whether that's true or not,I don't know.
But it I'm kind of using that asa as a as a reference, as
(42:51):
something to compare it to.
Not that I was married, but thatI was some like, I guess you'd
say married to the army, andthen it's like they're taking
away my identity.
You're out, you're done.
And and so the second time itwas easier when I I did retire,
and then I would say, even whenI was doing the contracting, I
was like, I don't really likethis as much as I thought I was
(43:12):
going to.
It's all just about money.
I I know there's contractors outthere who do a great job and
they're very fulfilled, so Idon't want to discourage
anybody.
And maybe I only did onecontracting job, it's only for
seven months.
People do it for years.
Some people move fromcontracting into government
service, and then you are backin the government again.
(43:32):
Some people love that, and theyget second careers, but for me,
it was a good thing getting outof the army.
Now I if I was still, if I was,I guess I I did have to retire,
but if I was still workingcontracting, still working
government service, it'd be veryhard for me to write the book,
pursue Spanish fluency, and getmy doctorate and make it a
(43:55):
priority.
And and there are people who doit.
I mean, we we've met thesepeople that you know, I was in
the army four years, I I Iworked uh in field artillery, I
got my bachelor's degree inthere, and then did my master's
degree in a year, and thenworking full-time, got their
doctorate, and then you know,people doing that, but I'm I'm
not that kind of person.
(44:15):
I'm with you, I'm not either.
SPEAKER_00 (44:17):
Well, it's it's amazing how you know how it's
evolved.
I mean, from you know, dealingwith some trauma as a child,
getting in the military, workingfor American Airlines, doing
some contract work, and thenfinding yourself in Peru.
And like you said, you weren'tplanning on being there, but you
ended up there for whatevercircumstance.
And like you said, in your mind,you know, it was God that put
you there.
(44:37):
And I think that that's abeautiful, beautiful thing to
say.
So I know for you, I've heardyou say or I've read somewhere
talking about living, not justexisting.
And when you think of that, whatdoes that mean to you?
Okay, what that means to me, Itold you I had a great time
being an army reservist jumpingtour to tour.
SPEAKER_01 (44:55):
Now I I need to talk on the downside of that.
If I was an army officer and Iwas on active duty, I would not
have to worry about renewing mycontract, looking for another
tour, getting people above me inrank to sign off on this,
getting my units to sign off.
Yes, we'll let you go.
Sometimes arguing people,getting them to do it, making
(45:17):
concessions, making agreementswith people.
So I was doing what I had to doto build up a good retirement,
retire earlier than 60.
And so, I mean, we're I guessit's the old living to work or
work to live.
I mean, it's it's easy for youto say, well, it's easy for you
to say now you have a pension,but I I do know what it's like
(45:37):
to struggle.
I know what it's like to nothave enough money to get your
car fixed, you know, to havepneumonia and need to go to the
doctor, and you're like, I don'tknow if I have enough money to
do this, you know, to have yourcredit card maxed out.
I've been in all thosesituations, you know, have a
toothache and not have enoughmoney to go to the dentist and
then uh and and been withoutinsurance.
(45:59):
So money is very important, butyou you want to live your life.
And it don't base it just onmoney.
Base it on you need to be ableto live, you need to be
realistic.
But you know, it when you'reable to, then I'm not saying
don't work, but do do somethingthat you want to do.
SPEAKER_00 (46:15):
Do what you love.
Do what you love.
I think that's a that's a greatthing.
And that's what I'm you know, Ido journey with Jake because I
love it.
I love hearing people's stories,I love hearing who they are.
I've really enjoyed hearingabout who you are and what
you're doing.
Before we wrap it up, though,tell me again the name of the
book and when is it when do weexpect to see it?
SPEAKER_01 (46:32):
Okay, it's with the editor right now in September,
and it's uh Trapped inDeception.
Trapped in Deception.
It'll be out in December, andyou can go to my website at Ken
Webb with two B's, K-E-N-W-E-B-B69.
69 is my birth year, KenWeb69.com.
And I have a YouTube channel,you know, at Web2000, same thing
(46:56):
with Instagram.
And and they can find me onthere, or it's also on Facebook,
and I'm it's I'm actuallyspending a lot of money
self-publishing.
Uh statistics are telling me Iwon't get my money back, and I'm
okay with that.
I I want people to read the bookand say this was good, because
there's a lot of, I mean,especially now these days,
(47:16):
people are just grinding outbooks.
And, you know, well, the coverlooks good.
And I paid somebody on Fiverrfor the cover, by the way, but
you know, you I I want to read,I want to create something
that's good.
You know, you just because youknow, some of the top physicists
in the world, some of the peoplethat are you know the best at
some of their professions, theydon't ever become wealthy doing
(47:39):
it.
So you don't do it for thatreason.
You you do it because you wantto be as good as you can be at
something, be the best versionof yourself.
I like it.
SPEAKER_00 (47:49):
I appreciate that.
Thanks for sharing that.
I'm just gonna end with somekind of, I guess we'll call them
rapid fire.
I don't know if there's a rapidfire, but just a few fun little
things to kind of end us outhere.
So you're learning Spanish.
I want to know what's a Spanishphrase you've learned that kind
of makes you smile, makes youhappy.
SPEAKER_01 (48:06):
Uh my my girlfriend in here, hablo contigo or con la
pared.
Am I speaking with you or withthe wall?
Meaning, like, are you listeningto me?
Or con la pared?
SPEAKER_00 (48:19):
Yeah, I like that.
SPEAKER_01 (48:20):
Yeah, she she do you speak Spanish too?
SPEAKER_00 (48:22):
I do speak a little Spanish, yeah.
I lived in Uruguay for a coupleyears.
SPEAKER_01 (48:25):
Recently, I I think I think she came up with this
one, I'm not sure, but she I wassaying, you know, don't do this,
don't do that.
And she said, Ken, I'm Ken, nosoy un problema con piernas.
I'm not a problem with legs.
SPEAKER_00 (48:41):
So there there can be I've noticed I have a good
sense of humor down here.
So for you, when you're writing,are you a coffee or tea guy, or
what is your choice of beverageto keep you going while you're
writing?
SPEAKER_01 (48:52):
I'm a coffee person and I'm a binge writer.
My most creative time, I I Iwant to get up early in the
morning to write, but then I geton a binge.
So I'll go to Spanish class,I'll come back, and I'll you
know, I'll be writing allthrough the night, keeping up
myself up with coffee, becauseit just I I get these some
people say the mental blocksdon't exist, but whatever it is
(49:14):
that's stopping me from writing,and and then it will just cut
come hit me, and then all of asudden, it was just like when I
did my well, I was working on mymaster's degree, you know, and I
sometimes it would be I had toget a paper in by a certain
time, and the teacher would say,Oh, this is excellent.
It would be like the last twoparagraphs, and I wrote it in
(49:35):
like four minutes, andsometimes, you know, when you're
under that pressure and you justwrite, sometimes it's just good.
And I'm gonna tell people don'toveranalyze your stuff.
Comes a point where you say it'sdone, and AI will look at your
stuff and scrutinize it, but itits objective is to make it the
(49:56):
most grammatically correct itcan, and sometimes that takes
away from the art.
Perfect.
I love it.
What's one place in Peru that'sjust really kind of stolen your
heart?
I would have to say uh Oxapampaor Pazuso, if I'm pronouncing it
right.
That's the old Germansettlement.
It's very beautiful.
The people there do not speakGerman, but a lot of them are
blonde.
You see a lot of people withblue eyes, and that's the same
(50:18):
reason in the U.S.
You know, my my grandparents'family were from Germany, but
generations back they no longerspeak German.
It just gets out.
But a lot of the influence, so Iwould I would say that oxapapa.
SPEAKER_00 (50:30):
And then finally, my last question again, thank you
so much for sharing who you are.
But if you could sum up yourjourney in one word, what would
that be?
SPEAKER_01 (50:38):
Struggle.
SPEAKER_00 (50:38):
Struggle.
Yeah.
Childhood, military.
Yeah, even learning Spanish.
There's a struggle.
SPEAKER_01 (50:44):
It didn't come easy.
It didn't come easy.
SPEAKER_00 (50:46):
Ken, thank you so much for coming on Journey with
Jake.
SPEAKER_01 (50:48):
All right, thanks for having me, Jake.
SPEAKER_00 (50:50):
What an incredible conversation with Ken Webb.
I'm so grateful to Ken foropening up and sharing not just
his military experiences, butthe personal journey that shaped
who he is today.
His story is a reminder that nomatter where we've come from,
it's never too late to livefully and chase the things that
make us come alive.
You can learn more about Ken,his writing, and his adventures
(51:11):
by visiting Ken Webb69.com.
I'll also have that link in theshow notes.
As always, thank you forlistening to Journey with Jake.
It means so much to have youalong for these adventures each
week.
If you've been inspired by Ken'sstory, please share this episode
with someone who could use alittle encouragement, and don't
forget to leave a rating orreview.
It really helps others discoverthe show.
(51:32):
Next time we're hitting the openroad with Matt Savino, who takes
us along his incredible journeydown the Pan American Highway.
It's a wild ride packed withadventure, challenge, and heart.
You're not gonna want to missit.
Just remember, it's not alwaysabout the destination, as it is
about the journey.
Take care, everybody.
From a childhood filled with chaos to a career
(00:02):
spanning more than three decadesin the military, Ken Webb's
story is one of faith,resilience, and rediscovery.
Today on Journey with Jake, Kenopens up about the battles he's
faced, both on and off thefield, and how those experiences
shape the man he is today.
Now living in Peru, learningSpanish, and writing his first
novel, Ken shows us what itmeans to truly live with purpose
(00:25):
and not just exist.
This is an incredible journey ofcourage, healing, and adventure.
Welcome to Journey with Jake.
This is a podcast aboutadventure and how through our
adventures we can overcome thechallenges of life that come our
way.
While I expect you will learnsome things about different
adventures, this show willentertain you.
Each episode will featuredifferent guests or guests that
(00:46):
they share experiences andstories from the different
adventures they have been on.
Not only will you beentertained, but you will also
share the failures and trialsthat each guest faces what they
have done or are doing toovercome the hardships that come
their way.
My goal is to take each of us ona journey through the
experiences of my guests withthe hope that you'll be
entertained and inspired toovercome your day-to-day
(01:09):
challenges.
After all, stop the destination.
As my intro music fades, I justwant to welcome you once again
(01:32):
to Journey with Jake.
If you're new here, this iswhere we dive into the stories
of adventure, resilience, andthe purpose that shape who we
are.
Don't forget to follow along onInstagram at Journey with Jake
Podcast.
It's a great way to see thepersonal side of my own
adventures and stay up to datewith what's coming next.
Today's guest, Ken Webb, bringssuch an incredible mix of grit
(01:52):
and grace to a story.
From a difficult childhood toover 30 years of service in the
military, Ken's life has beenabout overcoming obstacles,
trusting his faith, andcontinuing to grow, even now as
he lives in Peru, learningSpanish and writing his first
novel.
And if you enjoyed thisconversation, be sure to go back
and listen to bonus episode 10with Special Forces Operator
(02:13):
Chris Brewer, another powerfulstory about courage, purpose,
and the call to adventure.
All right, let's get into itwith Ken Webb.
Another episode of Journey withJake is here, and I've got Ken
Webb joining me.
Ken, welcome to Journey withJake.
SPEAKER_01 (02:26):
Thanks for having me, Jake.
SPEAKER_00 (02:27):
Yeah, I'm excited to talk to you.
I read a little bit about yourbackground and kind of what
you've done.
You've spent a lot of time inthe military.
It was a big part of your lifeand who you are, but also your
childhood was something that wasa little bit different.
And before we talk about yourmilitary career and what you've
got going on now, I'd like to goback and what was it like
growing up in a home marked bytrauma and chaos in your mind?
SPEAKER_01 (02:49):
I mean, it was difficult.
I mean, I'm a Christian.
I did a lot of praying.
You know, I was raised mostly bymy uh maternal grandparents,
meaning the mother and father ofmy my mother, but then my mother
was married five times, and andyou know, like with step uh
father and and stepbrothers,there's always difficulty,
(03:11):
always tension in there, andsometimes I bounce back and
forth between homes.
It was very difficult.
It was very difficult for me.
And it was in the 70s because Iwas born at 69.
People didn't understand as muchabout children at that time.
And and I mean I mean I'm sureit was probably better than it
was like in the 1940s, 50s, or60s, but my experience, and you
(03:35):
know, at that time we were justgetting out of the phase where
children were supposed to beseen and not heard.
So, you know, you have anytrauma, you just kind of suffer
in silence.
I really am very fortunate formy grandparents.
I'm referring to my mother'sparents because they they did uh
they were a sort of like ananchor for me.
You know, through them, my mygrandfather was a very good
Christian, and and mygrandmother was a a Christian
(03:58):
also, not as outspoken about it,but I I uh have to give them
credit for being like my rock.
Whereabouts did you grow up?
I grew up outside of SouthPhiladelphia, a town called
Collingdale,C-O-L-L-I-N-G-D-A-L-E.
It's about I guess about twomiles, maybe two and a half
miles, uh straight line distancefrom the Philadelphia airport.
(04:21):
And to give people an idea, ifyou you've flown in, there's but
it's not this isn't a huge town,and I don't know anybody famous
from there.
But it's it's in DelawareCounty.
It's not in Delaware, but it'sin Delaware County.
And it's it's next to SharonHill, uh, you know, Upper Darby,
Springfield, those kind oftowns.
Yeah, it's a lower income town.
(04:43):
I think it was a nicer, it'salso where my my mother grew up,
so it's uh it was a nicerneighborhood at that time.
SPEAKER_00 (04:49):
Well, so it sounds like your grandparents were a
huge influence on you for thegood, which was nice to hear.
You talked about you talkedabout being a Christian.
That's something you just kindof grew up with because you
talked about praying a lot.
Talk about your faith a littlebit.
SPEAKER_01 (05:02):
Well, I mean, I'm not one of these people that you
know they say you have to know aspecific time when you became a
Christian.
I I I used to tell people when Iwas 13 years old, because then I
I did the sinner's prayer.
I was in a in a place of prayermeeting and did the sinner's
prayer, but I I don't believethat.
I mean, if you you look in theBible, it doesn't say you have
(05:23):
to like say a specific prayer.
That's that's just somethingthat people do, and I believed
before then.
So I I think it was before that,I don't know exactly when, but I
mean, growing up, at least withmy grandparents, my my
grandfather always went tochurch.
Now, something interesting, mymy grandmother did not.
He lived right around the cornerfrom the church.
She would prepare breakfast andlunch and everything like that,
(05:44):
very traditional, you know,husband and wife.
She never learned to drive.
Uh, she worked up until they hadkids, and then she didn't work.
Her job was to take care of thekids, but she kept the house
spotless and always cooked andcleaned, did everybody's
laundry.
You know, her adult kids, shewanted to do their laundry, you
know, bring your laundry, I'lldo it.
And only my uncle did that.
The the two sisters did not.
(06:05):
But uh I went to Sunday school,but in my case, at least, I
don't think this was from thechurch.
I think this was just mygrandfather.
It was a reformed Episcopalianchurch, which falls under the
Anglican.
It's very different thanEpiscopalian.
It's very uh Episcopalian hasbecome very liberal.
This reformed Episcopalian isstill very conservative, but I
didn't actually attend churchuntil I was confirmed into the
(06:26):
church, and that was at at theage of uh 13.
Then when I moved down to Texasto be with my mother, I uh after
her third divorce, or during herthird divorce, I started going
to a Baptist church.
Uh, but now I've moved back.
Down here in Peru, I go to anAnglican church, and it is a
conservative Anglican church.
I really I believe more uh alongthose lines.
(06:46):
I mean, if if you're aChristian, you're a Christian.
But uh I I just when I read andstudy, I'm more along lines with
that.
Um I'm not I'm not seeing peoplein the Bible that were
prohibited from drinkingalcohol.
Jesus drank alcohol, and therewas wine available in those days
that was non-alcoholic.
There was grape juice that wasavailable, and yet he drank the
(07:08):
alcoholic kind.
But some Baptists, some otherdenominations will tell you, you
know, you can't dance.
Well, people danced in theBible.
I mean, I guess there's a fullspectrum.
There are different kinds ofdancing, different ways you can
dress when you dance.
I think instead of gettinginvolved in legalism or legalism
thing, I think God is much moreconcerned with our relationship
with Him than in how we dress oreven in what we do.
(07:32):
Our relationship with Him isactually more important.
So yeah, it was I I prayed a lotthrough some of those tough
times.
I do feel I was deliveredthrough a lot of that.
Uh I didn't witness any likemiracles, but you know, things
that just like when thepercentages were very much that
you know something should havegone the wrong way, and it
through a lot of prayer it wentthe right way.
I I give God that credit.
SPEAKER_00 (07:54):
Was it growing up, was it like abuse and things
like that?
Was it just instability?
You know, your mom's gettingdivorced a bunch of times.
Kind of all of the above?
Is that what was going on?
SPEAKER_01 (08:04):
Uh there was some abuse.
There was some uh sexual abusefrom sexual abuse from a
stepbrother.
That was the only person thatwas sexual abuse.
My mother, it was some, I mean,I I mean the times change, but
there was verbal abuse,psychological abuse, even from
my mother, definitely from mystepfather.
Stepfathers, actually.
My mother died in uh July the30th, 2024.
(08:27):
My stepfather just died thisyear.
He had dementia.
He was in a nursing home.
I I can't say he was reallyabusive.
He was maybe narcissistic,especially in the end, but I he
wasn't really an abusive person,and he was never abusive
physically with my mother.
He might have played some gameswith her, but yeah, I know my
(08:48):
mother was married, her secondhusband was a pathological liar.
He was a salesman.
My mother was divorced from hersecond husband.
Uh, I guess I must have beenfour years old, something like
that, so I don't remember him.
There was no physical, sexual,psychological abuse.
SPEAKER_00 (09:04):
I know you've spent a big part of your career in the
military, but I I you know,thinking back to those early
days and the struggles you wentthrough, do you feel it helped
prepare you for your you knowthe struggles you'd face later,
like in combat and being in themilitary?
SPEAKER_01 (09:17):
I I think there are many ways, you know, to prepare
for something.
I think it did, but I I don'twant to give somebody the
impression that it prepared mebetter than so you know other
things.
You can you can learn you canlearn not to you know burn your
hand by sticking it in the fireby listening to common sense and
observing, or you could stickyour hand in the fire.
(09:37):
That doesn't mean sticking yourhand in the fire is is the best
way to do it.
So I I think it did.
It it helped me because some ofthese issues and things I ran
into in the military seemed verylittle compared to uh you know
what I had faced as a child, andand they weren't like life and
death situations as a child, butit was something where like I
was, you know, you're a child.
(09:59):
You don't have control, youdon't have money, you can't just
get up and say, Well, I'm gonnalive over here, or no, I'm not
gonna do that.
I'm not gonna obey your rules.
You just can't do that whenyou're a child.
SPEAKER_00 (10:10):
When you look back at that childhood, is there a
lesson that you've carriedthroughout your life that you
learned as a child?
SPEAKER_01 (10:16):
What I learned from that, and I I mean I I mean
anybody can get the right answeron a test, and they say, Don't
steal, don't do this, don't lie,don't use bad language, but then
following through and do it,that's another.
I mean, none of us would eatjunk food or anything.
We all know it's bad for us, butwe do it.
Uh, one thing I I I try to takefrom that is, you know, to to
(10:38):
face your demons, to deal withyour problems.
You know, to take care of thingsuh not just during this life,
but you know, before you die,get a will, make sure
everything's taken care of.
Don't leave everybody with amess, be responsible.
Everything I've read, whenpeople get older, they're mostly
bothered by not the things theydid, but the things they did not
(11:00):
do.
So, you know, chase your dreams.
That's what I'm doing down herein Peru.
I'm I'm gonna I could haveworked as a contractor, I was
making good money, and Idecided, you know what, people,
I'm 56, people my age are dying,cancer, stroke, everything else.
I I'm gonna do what I want todo.
Uh, I do not believe with amentality of sitting in front of
(11:21):
the television.
I didn't retire early so I couldwatch television.
You know, I go to the gym, I Iread a lot, I'm learning
Spanish, uh, writing my firstnovel.
I I'm gonna work on mydoctorate.
I want to do it online so Icontinue, I can continue to live
down here and and to continue tolearn Spanish.
SPEAKER_00 (11:41):
You're talking about, you know, living,
actually living and not justkind of going through life,
which I like to hear.
And this is podcast that's allabout that.
It's an adventure podcast.
For you, and usually I kind ofdo this at the end of my show.
I want to do it right nowbecause we're kind of jumping
into things that you're doing.
What does adventure mean to you?
SPEAKER_01 (12:28):
Well, adventure to me, I mean, I'm I am not an
adrenaline job.
I'm afraid of height.
You know, they have this thingover the cliffs here where you
get on like a parachute.
It's not a parachute, it's likea paragliding type thing with an
engine.
As somebody will go with you,and then they'll take you out,
and people are saying, oh no,it's safe, it's safe, it's safe.
And I said, Yeah, but you haveto sign a disclosure for that,
don't you?
About if you get dismembered ordie.
(12:50):
I said, I don't have to do thatat the school I go to.
So there is some danger there.
You know, you're you're you'rethere there is some danger that
they're just not admitting to ordon't want to think about, or
they just don't care.
And I'm I'm not a drink, I amafraid of heights.
I was, you know, I took flyinglessons.
I the only thing I couldn't dowas solo, and that's because I
was afraid.
So, but adventure to me is notonly putting yourself in
(13:12):
physical danger.
Now, I am a big scuba diver, bythe way.
Ironically, depths don't botherme.
It's the heights, it's the otherway.
So yeah, and adventure to me isgoing out trying something new,
pushing yourself.
Ask my teacher, you know, shouldI continue with two hours a day
on Spanish or go to four when mybook is done?
She thinks two hours a day, theone teacher said the other
(13:34):
teacher said four.
I think in order for you toimprove at something, whether
that's going to the gym or orrunning or anything else, you
have to push yourself a littlebit.
You have to, if you'recomfortable, if you're if you're
just lifting weights enough andyou're you're never sore
afterwards, you're not doing agood job.
You need to push yourself alittle bit.
So I need to be a littleuncomfortable and it needs to be
(13:55):
a little bit inconvenient, orI'm not maybe inconvenient isn't
the right word, but it needs tobe a little bit of a strain on
me, just like whether that'sphysical or or mental.
And I'm not saying like, I mean,some of these Japanese students
go because their companies sendthem eight hours a day and
they're like sleeping in class.
So I don't mean like that.
Uh I don't mean push yourself inthe gym until you're in pain and
(14:16):
you injure yourself.
But you know, uh to me, anadventure is getting out, trying
something new, traveling, notbeing stupid with your money,
but not going with the idea thatyou're gonna die with all your
money.
You don't want to be the richestperson in the graveyard.
But you all you also don't wantto be the poorest person in the
graveyard, you don't want to diestruggling for money.
SPEAKER_00 (14:36):
Yeah, it's finding that right balance for sure.
I appreciate that.
So I know you spent over 30years in the military.
Why the military?
What got you into the military?
You always wanted to do it, itwas something you'd looked up to
as a kid.
Why'd you get in the military?
Uh you're exactly correct.
The answer would be yes to that.
SPEAKER_01 (14:51):
Okay, but I always knew I wanted to be in the
military.
I wasn't sure.
Never really thought I wanted tobe in the Air Force, but I I I
never really thought I wanted tobe in the Marine Corps, but I
was like Army or Navy, somethinglike that.
And I knew Army was big and theyyou could live in many different
places.
Navy was always kind of neat.
I love the water.
But I was at a junior collegeone day, saw somebody I'd gone
(15:15):
to high school with, he was in amilitary uniform.
And I I said, you know what,people don't normally wear
military uniforms with boots andand the hat and everything.
I mean, I was like, so what'sgoing on here?
And he and I weren't reallyfriends, we were just we just
kind of knew each other.
He was an acquaintance, and hethere he was in the ROTC
program.
So that summer I went went tobasic training and and uh was
(15:40):
enlisted for a little while andthen I got commissioned through
the University of Texas inArlington, and and then I was
commissioned as a militarypolice officer, but I was in the
Army reserves.
This was in 1992, it was afterthe Gulf War, and military was
being downsized.
So when you're a reservist,well, you if you're not gonna
continue education, which I Itried getting a master's degree
(16:02):
immediately after my bachelor's,it didn't work out.
But if you're not gonna do that,then you need to get a civilian
job as well.
So I had various civilian jobs.
I taught English for a year.
Uh I was not certified, but Itaught it for a year as a as a
substitute at uh Arlington HighSchool in Arlington, Texas, 11th
grade English.
(16:22):
Worked for a friend's businessfor a while.
We're working uh not, it wasn'tI I call it technical writing,
but really it was just morewriting manual stuff for a
company.
It wasn't that technical.
And then I got a job withAmerican Airlines, and I was
just working in reservations atAmerican Airlines.
I uh was uh a captain in theArmy Reserves, and uh there was
(16:45):
this tour, these active dutytours.
So you have these reservatorswho go one week a month, two
weeks in the summer.
Sometimes they go two weekends amonth, but you can go on active
duty for a while.
And there was this tour in inKosovo and started on the 15th
of April 2001, and I was a forceprotection officer, and I was in
Kosovo on 9-11, and I was inPristina, Kosovo, and everything
(17:09):
went down on lockdown.
And at that time, due to youknow, troops being deployed and
you know, wartime operations, ifthat's the right word, combat
operations, a lot of the pursesprings, uh purse strings were
open and people were mobilizedvoluntarily and involuntarily.
American Airlines changed itspolicies from being mobilized
(17:31):
five years to as long as troopsare deployed, which is
technically, I think, still thecase now.
But I would just mobilize andI'd go on one tour after
another, you know, look atsomething neat, estate,
eventually transfer it over tomilitary intelligence, you know,
was what I wanted to do.
And uh I had a scholarship, bythe way, for my bachelor's
degree.
So then on my master's, I useduh tuition assistance, which
(17:54):
paid for most of my.
I went to American MilitaryUniversity, which is entirely
online, and I used a smallamount of my GI Bill when that
would when the tuitionassistance was put on hold for a
while.
So instead of 36 months, I have34 months left.
I want to pursue my doctorate,and I have no idea what I'll do
with it.
I want to do it in intelligence,unclassified, of course.
It's all the classes will all beunclassified, and it's I don't
(18:18):
know if I'll do anything withit, but it's it's a personal
goal.
SPEAKER_00 (18:22):
I think we all have to have goals.
I like that.
Yeah, even though you may notwant to do anything with it, who
knows or what you'll do with it,you have that goal.
I like the fact that you havethat goal.
So all these tours, you startedKosovo.
Where else did you serve?
Like what what other tours, ifyou can tell?
SPEAKER_01 (18:36):
After Kosovo, I went to Joint Task Force Six, which
is Joint Task Force South.
Now, of course, for thosemembers who are in the reserves
or National Guard, there'ssomething called the Soldiers
Sailors Act.
And that gives you, and thingsmay have changed because I've
been retired a few years, butgave you 90 days to return to
work after that.
So I went to Joint Task ForceSix, which is now Joint Task
(19:00):
Force South.
It's uh it's a counter-drug,counter-nar narcotics on the
border.
And it was the border of Texas,it was in El Paso, New Mexico.
I don't think did we go inCalifornia?
I don't think I ever went toCalifornia with them.
And it was, you know, in I wasstill military police at that
time and had some Intel peoplewith me.
We would be in civilian clothesand do assessments of the
(19:22):
border, and and we weren'ttrying to stop people from
coming in illegals, but we weretrying to stop drug trafficking
there.
But it wasn't stopping it withfirearms.
We weren't carrying firearms.
It was to do an assessment, whatthings we could do.
We had some counterintelligencepeople working for us, with us,
not for us, but to to to lowerthat.
(19:43):
So then after that, let's see,the 2002, well, 2003, I went to
Iraq.
And I was actually, nope, I takeit back.
I take it back.
I went to the Joint AnalysisCenter, Joint Analysis Center in
Molesworth, England.
I joined it, I was there forseven months, and then I bought
(20:05):
an around the world ticket.
I was going to go back to workat American Airlines, but I had
three months, and I wastraveling around the world.
I was in Thailand.
I was on a scuba diving boat.
I got off the boat, checked myemail.
There's no WhatsApp or anythingthen.
Check my email.
This was in in 200 in two, inDecember.
It may have been, it may havebeen 2003.
(20:27):
It was 2003, early January.
Early January, because I did NewYear's in Tokyo.
I got an email, you know, returnto the United States
immediately.
We've been mobilized.
I contacted my Army Reserveunit.
I said, look, uh I'm I'm a scubadiver.
I've been scuba diving for threedays.
I can't get on a plane for 24hours.
I'll get decompression sickness.
So they said, as soon as youcan, come back.
(20:49):
So I did.
We did a convoy from GrandPrairie, Texas down to Fort
Hood.
And this was like duringOperation Iraqi Freedom.
So this was before they got realorganized with the stuff.
So after this, they they got towhere people would go in and do
their medical stuff throughoutthe year and prepare.
But we had people going through,you know, one guy had like six
(21:11):
teeth pulled.
There were some people got a lotof shots, and then they they got
better with this afterwards towhere people were getting shots,
but they were always ready todeploy.
But in the beginning, it was areal mess.
I went over there, I was abattle captain working under the
operations officer of the S3,and then I eventually became a
company commander because Ihadn't had a company command
(21:31):
yet.
Uh we returned to the UnitedStates.
I went back to being a you knowa weekend warrior for a while.
And then I did branch transferto military intelligence, went
to Fort Wachuca, which is whereI transitioned to it's in
Arizona to militaryintelligence.
I guess it's about an hour, Ithink it's about an hour, maybe
(21:53):
a little bit more from TucsonDrive, and it's it's not
terribly far from the borderitself.
Was up there for just about justunder three years, 33 months.
I remember that.
And then my new reserve unit gotmobilized.
We went to Afghanistan.
I went there in in 2009, butbefore this, we had a train up.
Went arrived, I guess it wasOctober 2009 and left August
(22:17):
2010.
I I did a very short tour, Imean like 60 days, to Stuttgart,
Germany, support of operation, Ithink it was New Dawn.
Can't remember the name of itvery well.
And we were counting airstrikes,and that was just because I had
the right clearance.
I had a top secret clearance.
There was nothing glorious aboutthat.
(22:38):
Came back, was then at up atFort Sill with the 75th Training
Division, training NationalGuard and Reserve members before
they went overseas to Iraq,mostly Iraq or Afghanistan, also
some nations in Honduras,training them to, you know,
making sure maybe instead oftraining them, there was some
training, but maybe it's moreaccurate to say assessing them
(23:01):
to see that they were ready togo, getting them up the speed
for that.
And as a unit as a whole, not asindividuals.
And then I did that same thingdown at Fort Hood, Texas.
And I did that about threeyears.
And then I went to GuantanamoBay, Cuba.
I was running some contracts outthere specifically with
linguists for languageinterpretation, working
(23:23):
alongside of interrogators, butI was not an interrogator.
I was not running interrogators,I was just running the
linguists.
I was out there for 18 months,got a tour going to Germany.
It was in logistics.
I had an additional skillidentifier in logistics, but it
was very hard for me because mybackground was military, police,
and intelligence.
And I people helped me and Istruggled through it.
(23:44):
And then I got to work back inintel, and I did that for a
year, and then I did not thatwas in Kaiserslaughter, Germany.
And then I did nine months inStuttgart again and enjoyed both
places or advantages to bothplaces.
Return from that.
Of course, in between all thesetours, I would go on trips and
scuba dive and travel.
(24:05):
And I had a great time, really.
It was stressful.
Trying to piece together thesetours can be very stressful
because there's time limits thatyou can be mobilized.
And when you reach that timelimit of being mobilized, used
to be three years, now it's goneto four, I think.
But then what you have to do isyou have to deploy, and that
resets your clock.
And deploying meaning going toIraq or Afghanistan.
(24:27):
Sometimes Kuwait, I think, butnow I don't I don't know if
Kuwait does it or not.
But then after that, I was outin intelligence role, a special
access program, but in anintelligence role more
administrative, out at CentralCommand at McDill Air Force Base
in Tampa, Florida.
And was out there about 15months and then went out to
(24:50):
Kosovo.
Uh uh, not Kosovo, went to CampBon Steel.
Not Camp Bon Steel, that isKosovo.
Went to Camp Arafgan in Kuwait.
And I was there just uh, I guessabout a year, and I was kind of
like the a mayor of this campfor a lot of intel people out
there, to make sure the lightswere on, make sure everything
was good, listening to theircomplaints and trying to make
(25:13):
things happen.
And then, believe it or not, itwas during the height of COVID.
This was 2019.
I remember in like, I think itmight have been November, I
started hearing whispers aboutthis COVID thing, and then a lot
of us thought it would just dieout.
So it was like by August, thiswhole thing will be dead.
December, it got really serious.
January, you know, people werewearing masks and all kinds of
(25:36):
lockdown.
My retirement date was in uh wassupposed to be June of 2020, and
I returned to the United States,went down to a good friend's
house down in Harlington, Texasto sit out the COVID, you know,
the waiting period ofquarantine, and did actually
retire, and then three dayslater got an email that said,
uh, so much of your retirement,you know, because I was an Intel
(25:59):
officer, Intel intelligence,along with other branches, they
were they were uh extendedanother two years for me to try
to make, I was a lieutenantcolonel, full colonel.
But the the dig about that wasto make full colonel, I had to
get a battalion command.
I had to get in charge of abattalion command.
And when I went to go do this,they said we have to have two
(26:22):
years left to get a battalioncommand.
And at that point, I'd only beenextended two years and I got
late notice, so I couldn't.
So what did I do?
I started looking for anothertour.
The stuff in the system wasshowing me already retired, so I
had to go about getting thatcorrected.
A lot of manual stuff.
I wound up going out to theUnited States Embassy, Baghdad,
Iraq.
(26:42):
My second time Iraq, this time Iwas on a diplomatic mission
under the Department of State,which meant for the first time
in my military career, I had toget a visa to go there.
I wasn't allowed to carry aweapon.
I wasn't allowed to do anythingmilitarily wise.
It was, you know, staying on thebase a lot.
We could wear our militaryuniforms sometimes.
(27:03):
Most of the time, we worecivilian clothes, and I was the
chief of operations, which isnot a job for an intelligence
officer.
That's a job for infantry, or ifyou're Air Force, a pilot, or
Navy, maybe a pilot, or or orsubmariner, or something more,
you know, macho on those lines.
So that that was that was aninteresting learning curve for
(27:24):
me.
And then that that took methrough September of 2021, and
there wasn't really opportunityfor another tour.
So I I did do the contractingroute after that.
I was actually with my leave,which is vacation I'd
accumulated.
I was on active duty statusuntil close, like close to the
(27:45):
end of October.
So then I went back to Kuwaitand I did it as a contractor.
And I was still in the ArmyReserves at that time, but I
went from being a lieutenantcolonel with my own office and
everything else to just being,hey, we need some help over
here.
Come over here at Ken.
I went to being Ken fromLieutenant Colonel Webb to Ken
or Sir to Ken.
(28:06):
This particular contract, Ididn't like it a whole lot.
I mean, there's a lot of verygood contractors out there, a
lot of very good contracts.
I felt like uh people wereabusing some of their
privileges.
You know, you got to live offthe base and and things going on
that I didn't like.
My mother was taking care of mystepfather.
He had dementia at that point.
(28:26):
She said, I need you to come offthat contract and come help me.
And so I I did.
And we got him under control,and I found another contract,
and I was going down.
I came down here to Peru.
My best friend had stage fourcancer, so I came down here, was
spending time with her.
I did the four-day Inca trail toMachu Picchu.
(28:49):
I was waiting on anothercontract, as I stated, and then
when after three months, theycalled me and I said, You guys
didn't give me any updates, andI had to go back to the U.S.
to go through a medicalscreening.
And that whole process they'regoing to have me go through
could take up to a year, andthey weren't going to pay me
during that time.
So down here where I'm living atin the Miraflores district of
(29:10):
Lima, Peru, I'm by the ocean,and it it's like living in in
maybe Santa Barbara somewhere inCalifornia.
I mean, we're talking Californiaterms.
I've never lived there, but it'sprobably probably like
one-fourth the cost.
Maybe one-fifth, depending.
And I was learning Spanish, Iwas liking what I was doing.
People my age, three people Iweren't, I wasn't friends with
(29:34):
them, but I knew them.
They died of cancer, and otherone died uh from a heart attack,
and I was like, I this isn't forme.
And the the contract that I wasbeing looked at was to go to a
top secret facility over inAustralia.
I'd be working in a buildingwith no windows, which is not a
normal that's normal for thattype of job.
(29:55):
But I'd be working 12-hourshifts, uh 12 noon to midnight
for two days, and then midnightto noon for two days, and then
four days off.
And it was at a place calledPine Gap near Ayers Rock, near
Ayers Rock, and it wasunbearable heat.
And I it wasn't like like goingto someplace really nice.
(30:17):
I've been to Australia beforeonce for about twenty twenty one
days or twenty three days,something like that.
Did a lot of scuba diving there,and this was not in in Perth or
or someplace that that you you'dwant to really go to.
And and stay at.
So I that is how I wound up.
But my mother got sick lastyear, so I had to return to the
U.S.
(30:38):
I was on a student visa downhere, which is hard to get.
And then after she died, I hadto, I'm her only child.
I had to take care of herestate.
My stepfather was in a home forpeople with dementia.
I had to take care of that.
And I was uh out of thiscountry, meaning Peru, for nine
months and then returned the17th of April, 2025.
SPEAKER_00 (30:58):
And now you're in Peru, living in Peru, along the
way.
Were you ever married oranything like that, or no?
SPEAKER_01 (31:04):
I've never been married, no kids.
I've never really wanted to havekids.
I think that has something to dowith difficulties I had growing
up.
I feel like I want to enjoy mylife.
And now I'm 56, and I I meanpeople do it, but I to me I
think it's off the table.
I mean, I I think, you know, ifyou're going to have kids,
that's great.
I don't know.
I mean, my mother passed away at77.
(31:26):
I mean, you I I I wouldn't wantto have a kid and then I don't
make it to his high schoolgraduation because I'm dead or
something.
I don't I don't know.
I mean, her father lived to be93, and her mother, who chained
smoke, well, she smoked twopacks a day for decades, lived
to be 88.
So, I mean, and my mother smokedone cigarette in her whole life,
(31:48):
so I I can't we we just don'tknow.
And I have never been I I wouldlike to get married someday.
Okay, so you are interested inthat part of it at least.
I think so.
My mother was married fivetimes, so I told people she took
my turn.
SPEAKER_00 (32:04):
She took advantage of it for you.
So, as far as you know, leavingAmerican Airlines, leaving these
contract jobs, going to Peru,why did you decide to do that?
I mean, do you at least becausethe other thing you had
stability, you know, it's kindof a it's sort of a risk, you
know, kind of leaving thatstability behind.
SPEAKER_01 (32:22):
I I have to be fair, other people have said things
along similar lines.
I have to be clear.
It used to, I mean, theretirement age for an army
reservist is 60 years old.
So when you go on these activedeployments in support of combat
operations, you can take a youwill take a year off that age.
And you have to be a reservistdoing that.
(32:44):
You can't be on active dutydoing that, a regular active
duty soldier.
So I got my age down to when Iretired, I immediately started
getting my pension.
Now the Army Reserve andNational Guard retirement is
based on points.
I had enough points that myretirement pension was the same
as someone who would have beenon active duty who was in for 20
(33:05):
years.
I have a whole lot of points.
Also, I did retire from AmericanAirlines.
I didn't mention that, but theyoffered an early retirement in
2020.
And you you had to be like, Ithink I was 45 years old, and I
I was like 50 or 51, 51.
I met, and they you know gaveyou a bunch of uh flight
(33:26):
coupons, and I haven't startedreceiving my pension yet.
I was 55 up to 60 is when I haveto take it, but it's at a
reduced amount, and I'm I'mdebating about whether to start
taking it.
But what I'm trying to say isthe risk maybe not as high if
you have a pension.
It's not as high a pension.
I mean, some of these peoplethat great adventurers or some
(33:47):
of these people that go in therelike they're going to take over
the world.
I I don't I was gonna say DonaldTrump, but then he's so
controversial, I don't want tosay that.
But some of these people, thethe thing in common that a lot
of these people have, well,including him, but uh there's
many other good examples.
These people have families witha lot of money.
I mean, if if something, iftheir business venture fails,
(34:10):
they're they're gonna be okay.
And I know that I have a pensionnow and I've been saving my
whole life, so I'm able to.
Good.
So you have the means.
And I don't have kids.
So I mean, I I spoke to myfinancial advisor today.
He's a little bit younger thanme, but he has two kids, and one
of them is a junior in highschool.
(34:31):
So I mean, that's a big I try tobe charitable, but I haven't
given the kind of money thatpeople should spend on their
children if they have it.
I could have gone tocontracting, still got my
pension, but there comes a pointwhere that, unless you love
doing that.
I mean, you get someone who'slike an actor or musician or
something.
I mean, some of these people areincredibly wealthy.
(34:52):
I don't think they're hopefullythey're not doing it for the
money anymore.
They're doing it because it's anart to them.
There's nothing wrong withmaking money.
SPEAKER_00 (35:01):
You know, if it's you need to be doing it because
you love doing it.
Speaking of loving what you'redoing, I know you love being in
Peru.
You've also You mentioned you'rewriting a novel.
Tell them tell us a little bitabout the novel and what that's
all about and why did you decideto write it?
SPEAKER_01 (35:18):
Well, you know, it's it's really this language school
I go to down here is named ElSol, and Soul is the name for
Sun, S-O-L in Spanish, the Sun.
The teachers down here have beena positive influence on me.
I I came down here saying I wasgoing to study Spanish and I was
going to study French and I wasgoing to, it's before my mother
got sick, and I was going to getmy PhD and then write a book.
(35:41):
I spoke to some of the teachers,and the one teacher, you know,
she said, Well, why do you wantto learn French?
Do you want to live in France?
And there's nothing bad aboutlearning French, but it's not a
world language like it was along time ago.
It's like, well, why are yougoing to do that?
There should be a reason thatyou're doing that.
You know, in high school, youelect a language you're going to
(36:01):
take, but I mean, so you have totake something.
So yeah, sure, take, but Spanishis very practical.
So I actually took that, Ithought about that that night,
and I was like, you know what?
Her name is Isabel.
I said, she's right.
Isabel, you're right.
I told her the next day.
Speaking to one of my teachers,I actually spoke to him today,
and his name is Romeo, and he'shis mother is uh Italian, so
(36:24):
he's he speaks some Italian, hestudied it down here, and he he
spent uh two years at in twodifferent one year and then uh
come back for another year inEngland studying English, so he
speaks very good English, and hesaid, Well, is your book about
your PhD?
Is it about your doctorate?
And I said, No, and he said,Then why do you have to wait to
write it?
(36:45):
Why you you don't have kids,you're you're not married,
you're you're not working, whywrite it, start it?
And that was in August of 2023.
I took a break of about sevenmonths when my mother died and
started again on it before Icame back here.
So in and all in all, I've I'vespent, I mean, it it'll be right
(37:06):
a year and a half to write it,maybe two years, a little bit
less, I guess.
I started writing it because itwas therapeutic for me.
You know, I had uh I'm a verytrusting person.
I'm a very uh you know, I I hidemy emotions, but I'm actually
very emotional.
And, you know, if I'm a friendwith somebody, I put a lot of
trust in them.
And the Trapped the Deception isa work of fiction.
(37:30):
However, there is so much realstuff in that book.
I mean, all the texts, all theemails that are in the book were
taken from real texts and realemails, changing only the names,
the dates, locations, times.
And, you know, I had a friendwho really betrayed me, and he
(37:52):
is not, I won't say apathological liar.
I'm no psychologist, buteverything I know about
pathological liars, they lieeven when they don't have to
lie.
Things can be going their way,completely going their way.
No reason to lie.
They're still gonna lie.
He's not like that.
He's much more dangerous becauseyou're gonna catch somebody who
lies constantly.
(38:12):
He's he's a very smooth talker.
Uh, I worked for him for a whileafter I graduated university,
and he was a salesman of sorts.
He became a school teacher, andthen he's he's in real estate
now, and I was the best man athis wedding.
But I realized he was somanipulative and so like a I
(38:33):
don't know what you'd say, uhemotional or even more than
emotion, just a person who wouldjust you know suck you dry if
they could.
You know, just use you and useyou and use you.
I I I have him the bad person inmy novel is modeled after him.
And it is not, I mean, in thenovel, he's a a much worse
(38:55):
person than this former friendof mine.
In the novel, I mean, he's amurderer, he's a drug addict,
he's he's he's really bad.
But it's it's based on, youknow, like a lot of these
movies, you know, that's basedon reality, they could be very
loosely based.
But this is is more, I mean, hischaracteristics, this idea of
gaslighting, which as I foundout, gaslighting is based off of
(39:17):
a movie by the same name, veryold movie, where you know,
you're just well, wait, I didn'tsay that.
And the very next day, well, youknow, you must have me confused
with somebody else.
I never said that.
Never taking responsibility forown actions and and consequently
maybe never feeling guilt.
Maybe being a sociopath.
(39:38):
Emotion that I have seen fromhim is anger when he's caught in
his lies, or when you don't buyinto them, when you don't pay
attention to him.
The good person in the book isbased loosely on me.
The good person in the book isnamed Eddie, and he is a
computer expert, which I amdefinitely not.
But, you know, I needed I neededsomething, you know, in the
(39:59):
novel, you need to base it onsomething, on someone.
It's loosely based on me, atleast as far as the his
behaviors and his relationshipto the bad person in the novel.
Eddie was an intelligenceofficer in the Army Reserves,
and he was in Kosovo, Iraq, andAfghanistan the same times I was
there.
(40:19):
So I'm not, you know, I was onthis one podcast and and people
was alive, and people were ableto put in questions while it was
going on.
You know, they're like, well,did you give away any, you know,
operational information?
Well, none no, I didn't.
Nothing I talked about reallyhappened as far as
(40:39):
operationally.
The novel, Eddie is uh out inAfghanistan and they're chasing
a Taliban commander.
You know, I I never did that.
Uh so but he gets credited forkilling the Taliban commander,
which I don't want to give awaytoo much, but it's it's like an
accident.
You know, like a I'll go aheadand say it's a discharge of a
(41:02):
weapon, and so he should havegotten reprimanded for it, but
he was running with his pistol,you know, and he was like, wow,
that was a great shot.
Well, he he killed him byaccident, complete accident.
He tripped into things.
How that does parallel my life,I kind of alluded to this
earlier.
I just kind of tripped intothings.
Peru is an excellent place tostudy Spanish.
(41:23):
I didn't choose it this way.
I was up in Cajamarca on a tripup there and wanted to go down
to Oxapampa, which is a Germansettlement.
I had to go through Lima.
The president had gotten introuble and was actually put in
jail at Peru.
This was back, I think it was2022, and I I couldn't go any
(41:45):
farther than Lima.
And I was like, well, I'm notjust gonna watch television, I
can do that in the UnitedStates.
I'm gonna do something.
So I started looking at Spanishschools.
I said, I'm gonna study Spanishagain.
I I just tripped into sometimesinto these things.
And I I do think that's God.
I do think that's God.
It's like because when Iespecially, I told you I retired
(42:07):
twice.
In 2020, I went through extremedepression.
I didn't want to retire.
My identity, I identified myselfas a lieutenant colonel in the
army, even though I was areservist.
I was always on active duty.
I was mobilizing, and it waslike taking away my, I guess,
away my identity, my persona.
I I've heard mostly this is fromI've never been married, but you
(42:30):
know, like women when they getdivorced, you know, it's so it's
harder on them, I've heard,because they take on the name of
their husbands.
So then it's like, well, nowyou're losing that, you're
separating from that that you'vetaken on.
And whether that's true or not,I don't know.
But it I'm kind of using that asa as a as a reference, as
(42:51):
something to compare it to.
Not that I was married, but thatI was some like, I guess you'd
say married to the army, andthen it's like they're taking
away my identity.
You're out, you're done.
And and so the second time itwas easier when I I did retire,
and then I would say, even whenI was doing the contracting, I
was like, I don't really likethis as much as I thought I was
(43:12):
going to.
It's all just about money.
I I know there's contractors outthere who do a great job and
they're very fulfilled, so Idon't want to discourage
anybody.
And maybe I only did onecontracting job, it's only for
seven months.
People do it for years.
Some people move fromcontracting into government
service, and then you are backin the government again.
(43:32):
Some people love that, and theyget second careers, but for me,
it was a good thing getting outof the army.
Now I if I was still, if I was,I guess I I did have to retire,
but if I was still workingcontracting, still working
government service, it'd be veryhard for me to write the book,
pursue Spanish fluency, and getmy doctorate and make it a
(43:55):
priority.
And and there are people who doit.
I mean, we we've met thesepeople that you know, I was in
the army four years, I I Iworked uh in field artillery, I
got my bachelor's degree inthere, and then did my master's
degree in a year, and thenworking full-time, got their
doctorate, and then you know,people doing that, but I'm I'm
not that kind of person.
(44:15):
I'm with you, I'm not either.
SPEAKER_00 (44:17):
Well, it's it's amazing how you know how it's
evolved.
I mean, from you know, dealingwith some trauma as a child,
getting in the military, workingfor American Airlines, doing
some contract work, and thenfinding yourself in Peru.
And like you said, you weren'tplanning on being there, but you
ended up there for whatevercircumstance.
And like you said, in your mind,you know, it was God that put
you there.
(44:37):
And I think that that's abeautiful, beautiful thing to
say.
So I know for you, I've heardyou say or I've read somewhere
talking about living, not justexisting.
And when you think of that, whatdoes that mean to you?
Okay, what that means to me, Itold you I had a great time
being an army reservist jumpingtour to tour.
SPEAKER_01 (44:55):
Now I I need to talk on the downside of that.
If I was an army officer and Iwas on active duty, I would not
have to worry about renewing mycontract, looking for another
tour, getting people above me inrank to sign off on this,
getting my units to sign off.
Yes, we'll let you go.
Sometimes arguing people,getting them to do it, making
(45:17):
concessions, making agreementswith people.
So I was doing what I had to doto build up a good retirement,
retire earlier than 60.
And so, I mean, we're I guessit's the old living to work or
work to live.
I mean, it's it's easy for youto say, well, it's easy for you
to say now you have a pension,but I I do know what it's like
(45:37):
to struggle.
I know what it's like to nothave enough money to get your
car fixed, you know, to havepneumonia and need to go to the
doctor, and you're like, I don'tknow if I have enough money to
do this, you know, to have yourcredit card maxed out.
I've been in all thosesituations, you know, have a
toothache and not have enoughmoney to go to the dentist and
then uh and and been withoutinsurance.
(45:59):
So money is very important, butyou you want to live your life.
And it don't base it just onmoney.
Base it on you need to be ableto live, you need to be
realistic.
But you know, it when you'reable to, then I'm not saying
don't work, but do do somethingthat you want to do.
SPEAKER_00 (46:15):
Do what you love.
Do what you love.
I think that's a that's a greatthing.
And that's what I'm you know, Ido journey with Jake because I
love it.
I love hearing people's stories,I love hearing who they are.
I've really enjoyed hearingabout who you are and what
you're doing.
Before we wrap it up, though,tell me again the name of the
book and when is it when do weexpect to see it?
SPEAKER_01 (46:32):
Okay, it's with the editor right now in September,
and it's uh Trapped inDeception.
Trapped in Deception.
It'll be out in December, andyou can go to my website at Ken
Webb with two B's, K-E-N-W-E-B-B69.
69 is my birth year, KenWeb69.com.
And I have a YouTube channel,you know, at Web2000, same thing
(46:56):
with Instagram.
And and they can find me onthere, or it's also on Facebook,
and I'm it's I'm actuallyspending a lot of money
self-publishing.
Uh statistics are telling me Iwon't get my money back, and I'm
okay with that.
I I want people to read the bookand say this was good, because
there's a lot of, I mean,especially now these days,
(47:16):
people are just grinding outbooks.
And, you know, well, the coverlooks good.
And I paid somebody on Fiverrfor the cover, by the way, but
you know, you I I want to read,I want to create something
that's good.
You know, you just because youknow, some of the top physicists
in the world, some of the peoplethat are you know the best at
some of their professions, theydon't ever become wealthy doing
(47:39):
it.
So you don't do it for thatreason.
You you do it because you wantto be as good as you can be at
something, be the best versionof yourself.
I like it.
SPEAKER_00 (47:49):
I appreciate that.
Thanks for sharing that.
I'm just gonna end with somekind of, I guess we'll call them
rapid fire.
I don't know if there's a rapidfire, but just a few fun little
things to kind of end us outhere.
So you're learning Spanish.
I want to know what's a Spanishphrase you've learned that kind
of makes you smile, makes youhappy.
SPEAKER_01 (48:06):
Uh my my girlfriend in here, hablo contigo or con la
pared.
Am I speaking with you or withthe wall?
Meaning, like, are you listeningto me?
Or con la pared?
SPEAKER_00 (48:19):
Yeah, I like that.
SPEAKER_01 (48:20):
Yeah, she she do you speak Spanish too?
SPEAKER_00 (48:22):
I do speak a little Spanish, yeah.
I lived in Uruguay for a coupleyears.
SPEAKER_01 (48:25):
Recently, I I think I think she came up with this
one, I'm not sure, but she I wassaying, you know, don't do this,
don't do that.
And she said, Ken, I'm Ken, nosoy un problema con piernas.
I'm not a problem with legs.
SPEAKER_00 (48:41):
So there there can be I've noticed I have a good
sense of humor down here.
So for you, when you're writing,are you a coffee or tea guy, or
what is your choice of beverageto keep you going while you're
writing?
SPEAKER_01 (48:52):
I'm a coffee person and I'm a binge writer.
My most creative time, I I Iwant to get up early in the
morning to write, but then I geton a binge.
So I'll go to Spanish class,I'll come back, and I'll you
know, I'll be writing allthrough the night, keeping up
myself up with coffee, becauseit just I I get these some
people say the mental blocksdon't exist, but whatever it is
(49:14):
that's stopping me from writing,and and then it will just cut
come hit me, and then all of asudden, it was just like when I
did my well, I was working on mymaster's degree, you know, and I
sometimes it would be I had toget a paper in by a certain
time, and the teacher would say,Oh, this is excellent.
It would be like the last twoparagraphs, and I wrote it in
(49:35):
like four minutes, andsometimes, you know, when you're
under that pressure and you justwrite, sometimes it's just good.
And I'm gonna tell people don'toveranalyze your stuff.
Comes a point where you say it'sdone, and AI will look at your
stuff and scrutinize it, but itits objective is to make it the
(49:56):
most grammatically correct itcan, and sometimes that takes
away from the art.
Perfect.
I love it.
What's one place in Peru that'sjust really kind of stolen your
heart?
I would have to say uh Oxapampaor Pazuso, if I'm pronouncing it
right.
That's the old Germansettlement.
It's very beautiful.
The people there do not speakGerman, but a lot of them are
blonde.
You see a lot of people withblue eyes, and that's the same
(50:18):
reason in the U.S.
You know, my my grandparents'family were from Germany, but
generations back they no longerspeak German.
It just gets out.
But a lot of the influence, so Iwould I would say that oxapapa.
SPEAKER_00 (50:30):
And then finally, my last question again, thank you
so much for sharing who you are.
But if you could sum up yourjourney in one word, what would
that be?
SPEAKER_01 (50:38):
Struggle.
SPEAKER_00 (50:38):
Struggle.
Yeah.
Childhood, military.
Yeah, even learning Spanish.
There's a struggle.
SPEAKER_01 (50:44):
It didn't come easy.
It didn't come easy.
SPEAKER_00 (50:46):
Ken, thank you so much for coming on Journey with
Jake.
SPEAKER_01 (50:48):
All right, thanks for having me, Jake.
SPEAKER_00 (50:50):
What an incredible conversation with Ken Webb.
I'm so grateful to Ken foropening up and sharing not just
his military experiences, butthe personal journey that shaped
who he is today.
His story is a reminder that nomatter where we've come from,
it's never too late to livefully and chase the things that
make us come alive.
You can learn more about Ken,his writing, and his adventures
(51:11):
by visiting Ken Webb69.com.
I'll also have that link in theshow notes.
As always, thank you forlistening to Journey with Jake.
It means so much to have youalong for these adventures each
week.
If you've been inspired by Ken'sstory, please share this episode
with someone who could use alittle encouragement, and don't
forget to leave a rating orreview.
It really helps others discoverthe show.
(51:32):
Next time we're hitting the openroad with Matt Savino, who takes
us along his incredible journeydown the Pan American Highway.
It's a wild ride packed withadventure, challenge, and heart.
You're not gonna want to missit.
Just remember, it's not alwaysabout the destination, as it is
about the journey.
Take care, everybody.
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