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February 21, 2024 43 mins

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Join hosts Rick Haney and Kaleem Clarkson as they engage in a lively and insightful conversation with Jesse Chambers, the visionary founder behind Wrkfrce, a premier digital media brand specializing in remote work. In this lively and insightful interview, Jesse recounts his journey from the confines of corporate media to the boundless realm of entrepreneurship, detailing the pivotal moments that culminated in the establishment of Wrkfrce.

Drawing from his experiences at AOL and Verizon Media during pivotal transitions and acquisitions, Jesse's entrepreneurial drive ignited his passion for remote work. Motivated by his firsthand experiences living in an Airstream trailer with his spouse, Jesse was inspired to align his mindset with his professional endeavors, laying the foundation for Wrkfrce. This profound realization propelled him on a journey of self-reflection, ultimately leading to the creation of a platform designed to address the unmet needs of remote workers by offering invaluable resources and insights.

Wrkfrce's content ecosystem is meticulously curated to encompass various topics vital to remote work enthusiasts, ranging from productivity optimization strategies to achieving a harmonious work-life balance. Jesse's interests extend to the evolving landscape of remote work, shedding light on the resurgence of office-centric work environments and the imperative for businesses to embrace adaptability to allure and retain top-tier talent. His insights, underscored by adaptability, continuous skill enhancement, and attentive employee engagement, resonate deeply with both individuals and enterprises navigating the remote work domain.

Reflecting on his personal experience transitioning to remote work while living in an Airstream trailer, Jesse shares anecdotes about the challenges of internet connectivity and the freedom it afforded him to work from various locations. His journey serves as inspiration for individuals seeking fulfillment and success in the dynamic world of remote employment, illuminating the trials of internet connectivity juxtaposed with the liberating freedom of location-independent work.

Jesse's passion for empowering and educating remote workers shines through, fostering a sense of camaraderie and shared experiences. Join Rick, Kaleem, and Jesse as they explore the transformative power of pursuing one's passions and shaping the future of work through entrepreneurship. Don’t miss out and get ready to take notes!

Keep leading the way in empowering remote workers and shaping the future of work, Jesse!

Learn more about Jesse:

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Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Kaleem (00:00):
Well, nice to see you, bro.

(00:00):
Appreciate you taking the time,man.

Jesse (00:02):
And you, and thanks, yeah, thanks for you guys help
troubleshooting my audio.
The audio, you know, never,never, never goes the way you
want it to go or, you know, thisis like the first time that that
mic has never not been like waybetter than these headphones.
So, uh,

Kaleem (00:16):
it could be a bad chord, you know, as you never know
what, what it could be, you knowwhat I

Jesse (00:20):
Yeah,

Rick (00:20):
it's, what we call, when I was in audio engineering school,
it's what we'd call signalflowis interruptus.

Jesse (00:27):
Yes.
The audio engineering school ofMIT, that's the, uh, the
technical term.

Rick (00:36):
Yep.

Kaleem (00:38):
Oh, that is great, rick, can you give us a little more
gain for yourself?

Rick (00:41):
I'm gaining on you.
How about this do it how do wedo now?
We

Kaleem (00:45):
oh yes.

Rick (00:46):
Are we in the smooth zone?

Kaleem (00:48):
Oh baby.

Jesse (00:49):
smooth.

Rick (00:50):
not enough O's in smooth

Kaleem (00:53):
baby.

Rick (00:54):
Dr.
Love coming at you

Kaleem (00:56):
The Love Doctor.
This is the, this is the podcastthat we're here.
We're

Jesse (01:00):
I think I clicked on the wrong link.

Rick (01:03):
Loving the show was wrong, I don't want to be right Hey,
everybody.
Welcome back to Remotely One.
I'm your host, Rick Haney,joined by my esteemed colleague,
Kaleem Clarkson.
How are you doing today, buddy?

Kaleem (01:22):
Oh man, I'm great, man.
Feeling good.
Geeked as always though.
Geeked as always for today'sguest.
Bro,

Rick (01:32):
I went and looked at the show notes you sent me at five
o'clock this morning, and Ialmost shit a brick.
I'm like, what's he on?
Let's see.
He's on point.

Kaleem (01:42):
You know why?
You know why Rick?

Rick (01:44):
What?
Oh, you got it.
You got it.

Kaleem (01:47):
That's right, bro.
I took you up on your magic mindrecommendation, bro.
And I can't tell you.
I can't tell you how alert I am.
I'm just

Rick (01:56):
isn't it amazing?
I can't believe you got it sofast.
That's incredible.

Kaleem (02:00):
Yeah, man, it's good, man.
It tastes good.
It's natural.
What I just love about it, man,is, is like, it's natural.
It's the buzz.
I don't have the jitters, Rick.
I just don't have those jitters.
So it's awesome, man.

Rick (02:12):
isn't it?
amazing how something withabsolutely no caffeine and
pretty much all naturalingredients can Set the tone for
the entire day.

Kaleem (02:21):
Crazy, bro.
I can't believe it, but forreal, Rick, I remember last time
you were telling our audiencehow they can get some of this
magic for their mind.
You know what I mean?
How can

Rick (02:31):
Yes, sir.
Yes, sir.
Thank you for bringing that up.
It's real easy.
All they gotta do is go tomagicmind.
com forward slash remotely oneand actually get up to 56
percent off the subscription forthe next 10 days or 20 percent
off a one time purchase with ourcode and that code is remotely

(02:52):
120.
R E M O T E L Y O N E 2 0.
That's our code, baby.

Kaleem (03:00):
There it

Rick (03:01):
Use it or you lose it.

Kaleem (03:03):
Use it.
or lose it.
baby.

Rick (03:05):
I love it.
Hey, with all that out of theway, Kaleem, give us a tease or
two about today's guest.

Kaleem (03:10):
Oh, yeah.
Oh, yeah.
Had to put on the multipleshirts again, sir, because I
guess make me a little nervous.
Okay, so

Rick (03:18):
did you double shirt today?
Did you

Kaleem (03:20):
I did.
I did.
double shirt for sure.
I can't sweat through this.
Can't sweat through this.
Don't want my guests to seethose all sweated out.
Don't want to see that.

Rick (03:28):
our coaches used to say?
If you ain't sweaty, you ain'tready.

Kaleem (03:38):
I am sorry.
There's just so many dumb assshit.
Coaches say, coaches say thedumbest shit, don't They

Rick (03:43):
All set?
You bet!

Kaleem (03:46):
Oh my gosh.
So our guest today, Rick,they're originally from New
York.
All right.
they're New Yorker.
They currently reside in Austin,Texas.

Rick (03:56):
that's a culture shift.

Kaleem (03:58):
Yeah.
Oh, yeah.
Oh, yeah.
Earlier in their career.
They were the director of salesfor a little company America
Online Tech AOL Tech.

Rick (04:09):
Boy, oh boy.

Kaleem (04:10):
Yeah, yeah,

Rick (04:11):
got mail.

Kaleem (04:13):
There it is.
So, they work with brands likeTechCrunch, Indigadget,
Crunchbase.
Just a few brands that youmight've heard of.
He then went on to be the globalhead of premium content for
another small little brand,Verizon

Rick (04:27):
Oh, can you

Kaleem (04:28):
Yeah.

Rick (04:29):
Can you hear me now?

Kaleem (04:30):
Huh?
Huh?

Rick (04:32):
now?
Can you hear me now?

Kaleem (04:34):
Oh, okay.
Yeah, yeah, yeah.
So this is interesting.
This is interesting.
So our guest.
He says he's about six to six,three.
Okay.
And, uh, he loves Chihuahuas.
So sometimes once in a while,you may see this six foot three,
larger size man walking throughthe parking lot with his

(04:57):
Chihuahua, Rick,

Rick (04:59):
of these things is not like the other.

Kaleem (05:03):
he, his wife and his Chihuahua, they moved into a 27
foot.
Airstream trailer.
Remember those bro?

Rick (05:09):
oh, I want to hear about this.
Yeah.

Kaleem (05:12):
they drove around the u.
s Uh, oh, he's a two timeremote.
com top 100 150 influencerCongratulations guests on that.

Rick (05:22):
Fantastic.

Kaleem (05:23):
He is the operator in residence at a little Known
incubator called Techstars.
I mean, yeah.

Rick (05:34):
Goodness gracious.

Kaleem (05:35):
It's like, what am I doing, Rick?
Shit.
okaY.
Not only that, but our guesttoday is the founder and CEO of
Workforce, which is the leadingdigital media brand for remote
work.
Listeners and viewers, pleasegive a warm welcome to Jesse
Chambers!

Rick (06:05):
That was an homage to

Kaleem (06:06):
Woo.

Rick (06:06):
chihuahua.
Ay, ay,

Kaleem (06:07):
Oh,

Rick (06:08):
ay,

Jesse (06:08):
Oh,

Kaleem (06:09):
bring that one in.
Settle down, studio audience.
Settle your asses down

Rick (06:13):
front, relax,

Kaleem (06:13):
Woo.

Rick (06:14):
assemblies.

Kaleem (06:15):
They do get loud.
Sorry about that.
Jesse studio audience.
Thank you for coming, bro.
Thank you.
Whoo.

Jesse (06:23):
when my alarm goes off.
That's going to fire me up andget me to start my day the right
way.
That was amazing.

Rick (06:28):
Now we're talking.

Kaleem (06:29):
That's what we're talking about.

Jesse (06:31):
Rick, I didn't realize that you coordinate or you
recorded the you've got mailtag.
I mean, dead ringer.
For that

Rick (06:41):
This is my real voice.
This is how I talk in everydaylife.

Jesse (06:48):
regret that some of the residuals from that have
probably lessened over theyears, but I'm sure it was very
lucrative for you for a littlewhile in the late 90s and early
aughts.

Rick (06:56):
Yeah, so I'm down to my shoebox apartment now.

Kaleem (06:59):
What the hell were you thinking?
Not just recording a whole bunchof those.
Jeez.
Come on,

Jesse (07:08):
I also would like to point out to the audience at
home to quickly that actuallyreally did do a shot of magic
mind if you guys don't have thevideo.
So, he's not playing.
He really did it.
So that energy is only going topick up over the next 30 minutes
or so.
Very impressive.

Rick (07:23):
I'll tell you what.
I mean, you got courage,brother, doing it this late in
the day, but where it doesn'thave caffeine, you might go to
sleep tonight entirely focusedon going to sleep, which means
you're going to sleep better.
I'm just saying.
Jesse, thank you so much forjoining us.
It's great to have you.
I have so many questions, and Iknow Kaleem does too.
We're excited to, to bring youon today, but, you know,

(07:46):
Airstream.
I've seen these things my wholelife.
I love the nostalgia thatsurrounds them.
I'm a huge vintage guy.
I love all things old.
And you took going mobile toheart, but you did it with
style.

Jesse (08:02):
Well, thank you

Rick (08:02):
what inspired you and your wife to really experience the
digital nomad life

Kaleem (08:08):
Yeah.

Rick (08:09):
flair?

Jesse (08:11):
Well, to be honest, like, like any smart husband, my wife
inspired me to buy an Airstream.
So,

Kaleem (08:17):
Nice shout out.
Did you mind saying her name?
So we can give her the truelove.

Jesse (08:22):
The intelligent and beautiful Lindsey Chambers, you
can find her on LinkedIn and

Kaleem (08:26):
shout out, Lindsay.
That's what we're talking about.

Jesse (08:29):
she would also, we, the travel gram of our time in the
Airstream was at wandering.
america on Instagram.
So if people want to followthat, you can see lots of shots
of the Airstream and my lovelywife.
Yeah, so Rick, you know, she,like you, big vintage fan.
She actually owned a vintageclothing store in San Francisco.
And the, it was born of really apractical necessity when I

(08:53):
founded Workforce.
I was living in San Francisco,and I quickly realized that the
idea of founding andbootstrapping a startup and
paying for housing in the BayArea was not going to be a
practical solution.
And, as we were thinking aboutwhat our alternatives were, we
had always dreamed of travelingthe country in an Airstream

(09:13):
because of her love of allthings vintage.
We didn't ever think we'dactually be able to do it, but
we crunched the numbers and,realized that it was going to be
a whole lot cheaper than livingin San Francisco.
It was also going to alignreally well with what I was
doing with the business.
And it was a chance for my wifeto, buy and decorate an
Airstream trailer.
So, we took the leap and did itand you should too.

Rick (09:36):
I hope to someday, I'll be honest with you.
Now you mentioned, how long agowere you guys, or did you leave
San Francisco?

Jesse (09:43):
Yeah.
So, we founded the company.
I founded the company in 2019.
So we left San Francisco and ourplace in San Francisco pretty
much sold everything except forthings like college year, high
school yearbooks and my recordcollection and her wedding dress
and moved into the Airstream.
The timing was.
Pretty inspired, it was about ayear before the pandemic kicked

(10:04):
off and once that happened, youliterally could not buy an
Airstream.
It was everybody was, you know,RV life was all the rage and van
life was everywhere.
So we had pretty good timing inthat respect.

Rick (10:17):
I would imagine so.
My uncle has a vintage clothingstore in San Francisco.
my uncle?
Nah, I'm just kidding.
Yeah.
Um, it's called, uh, S SFMercantile.
San Francisco Mercantile.
It's down on, uh, yeah.
yeah, They got a couplelocations now, so they're doing
great.
I love San Francisco.
I would go there every weekendif I could.

Jesse (10:37):
my wife may know your uncle.
Yeah.
That was a small community andthey were all, it was really
cool.
It was a really cool, supportivecommunity of vintage people in
San Francisco and reallyinspiring.
Honestly, you know, my wife wasa founder and an entrepreneur
before I could say that aboutmyself.
And so her experience startingthat business and running that
store really, gave me theencouragement to be able to

(11:00):
strike out on my own and becomea founder too.

Rick (11:03):
Ah, good for you, man.
What a life, huh?
So much fun.
Entrepreneurship,

Jesse (11:08):
But, I will say, like, there are people who are lifers
who do that.
We did it for three and a halfyears.
And that was, at least enoughtime, maybe a year too long.
You know, being in Austin, Texasand, knowing that we are 5
minutes from a grocery store atany point and sleeping in the
same place every night you don'ttake those things for granted
after you're a full time nomadwouldn't trade it for anything.

(11:30):
But also not taking the smallthings for granted of living in
a traditional home.

Rick (11:37):
Oh, I can absolutely imagine.
And, you know, speaking ofwhich, your more traditional
role when you were at AOL.
I mean, AOL was infamous forbasically creating the internet
that we know today and goingthrough all these different
iterations.
You know, what was the big thingthat AOL was doing when you were
there?

Jesse (11:55):
So when I was, I'm happy.
I, you know, I wasn't there whenAOL was in its, you know,
acquiring Time Warner heyday,right?
So I joined AOL in, uh, I wantto say like 2007.

Kaleem (12:08):
So you didn't get a chance to meet Meg or Tom Hanks,
basically, like he

Jesse (12:11):
no, no, they were not in the office, not in the office
any longer.
But, the bloom was definitelyoff the rows of the company at
that time.
What was going on when I wasthere.
Was really the turnaround ofAOL.
So about a year after I got toAOL, a guy named Tim Armstrong,
became our CEO.
He had been the first salesemployee at Google.

(12:32):
And so he did okay.
And he went on to lead theirsales organization.
He came on and really turned thecompany around.
He acquired brands that I got towork on.
Like we mentioned, TechCrunchand he also acquired the
Huffington Post.
And so we became sort of, adigital media holding company
for a lot of brands outside ofthe AOL banner that people know.

(12:55):
And, it was a real successstory.
They went on to be acquired byVerizon, which is how I worked
at Verizon and Verizon media, insome, sort of expanding roles
there.
And then Verizon acquired Yahooand merged the two.
That was my cue to look for theexit and did my own thing from
there.
So, that turn around to answeryour question, Rick, it was a

(13:15):
real turnaround story and it wasa great lesson in leadership and
execution from first Tim, butalso a lot of other really
brilliant business people who'vegone on to do some pretty
incredible things that I got towork with there.

Kaleem (13:30):
Yeah, I find so fascinating about the AOL story
is that journey that they'vegone through.
And you're right.
I kind of forgot about thatsecond version of AOL.
And then as you were leaving,there was a third version.
Yeah.
So now.
Was that the Marissa Mayer timewhen Yahoo acquired them or was
Marissa was she hired it?
Do you remember?

Jesse (13:49):
She was there.
And Tim and Marissa were both.
Ex Google.

Kaleem (13:53):
Okay,

Jesse (13:54):
And they were, you know, they were cool.
Marissa was operating Yahoo upuntil the sale to Verizon.
And so when they merged thosetwo entities.
Marissa took the money and ran,God bless her and, uh, and Tim,
Tim stayed on to, to run thecombined entity for a little
while, but then moved on.
Tim's founded a reallyfascinating company called flow

(14:16):
code.
If you guys see like TV ads thathave QR codes on the TV or at
the Superbowl, that's flow code.
And they're doing reallyinteresting things with consumer
data and advertising data in theQR sort of the real world first
person consumer space right now.
So to Tim's not done to Tim, youknow, you want to make a good
investment, just buy into TimArmstrong, and

Kaleem (14:37):
Tim Armstrong that you heard it here.
You heard it here.
So you, you migrate from AOL.
You're part of that like mediarebuild, right?
Then you're part of the Verizonmedia rebuild as well.
What was the thing or the sparkor that moment that made you or

(14:58):
led you to create in workforcenow.
So now you've tasted media.
You've been a part of it.
You've been running it.
What made you think creatingyour own company?
And can you tell our listenerswhat workforce vision is?

Jesse (15:10):
So it's funny.
It happened very organically andhappened through that process of
professional growth andcorporate growth and corporate
mergers, honestly.
So, Around the time that theYahoo acquisition and the AOL
merger was going down, I wasn'tsure if I was going to have a
job or if I was going to wantthe job that I had on the other
side of that merger.

(15:30):
And so I said to myself, Hey,I've had a good run here for a
decade plus, I really enjoyedthis.
Maybe it's time for somethingelse.
And what I did was I didn'texercise that, um, I find really
valuable to do every couple ofyears, but this was valuable for
me at this time, which is tosay, let's take job title
company out of it.
What are the five things thatare most important to me that I

(15:53):
want in any role that I havegoing forward?
And it sounds funny to say, but.
Only through doing thatexercise.
Did I realize that I was aremote worker?
So I've been based in SanFrancisco the whole time, but
the company was based in NewYork.
I was, you know, sort of in thesales realm.
So I was going to, conferencesand client calls all the time.

(16:14):
I was spending one week.
Per month, at least in New Yorkat the corporate headquarters,
traveling around, I actuallyeven had desks in two offices in
San Francisco.
I had a desk in the main officeand Indy, in the tech crunch
office.
And so when I was in SanFrancisco, if I needed to be in
an office.
I could go to an office, and ifI didn't need to be in the
office, I could work from myhome office, and nobody was

(16:37):
going to say, where's Jesse?
I put it succinctly, I wastreated like an adult, but it
wasn't in my job descriptionthat I was a remote worker.
It just had organicallydeveloped that way.
And so I realized, though, thatI didn't want to give up that
freedom and that respect andthat choice of work style.
And so armed with that sort oflens, is that being one of the

(16:59):
most important things for me andwhatever my next role was, I
tried to go out and find, youknow, jobs like that, or
companies like that, orcommunities of people who are
working like that.
And this was in 2017, 2018, andthere was nothing really.
And I was really frustrated bythat.
And I was frustrated for about30 seconds.

(17:21):
And then I said, wait a minute,Jesse, you know, a thing or two
about building digital mediabrands.
If you wish that this thingexisted, maybe other people
would too.
And that was the sort of seedthat over time sprouted into
workforce.
So it, it very, you know, it, itwasn't necessarily inspired.
It happened very organically.
But once I sort of realized thatabout the way that I wanted to

(17:43):
work, I was then able to, youknow, check some numbers on that
and see where this trend wasgoing and seeing that remote
work was going to really growover a 10 year period.
Obviously, I nor anybody elsecould have predicted what we saw
happened with the pandemic andall that kind of thing.
So there's always an element ofluck, but that's historically.

Kaleem (18:04):
I mean, your timing, the self reflection prior to the
pandemic.
very interesting that I kind ofput you in this position.
So, you know, audience that selfreflection is a tough.
We've we had Jordan Carillon along time ago.
Rick.
I think I remember hearing himtalk about you got to do
yourself checklist of what'simportant to you.

(18:24):
And that's pretty cool that youthat.

Jesse (18:28):
I think it's a useful exercise for anybody at any
point in their career.
We can get caught up in jobtitles and company names and all
this kind of thing.
And I think, honestly, that'ssomething that becomes more
important with flexibility andthe ability to work remote or
hybrid, or what do you say?
Figuring out, you know, what isreally important to me and how
do I want to work and thengetting to company names and job

(18:50):
titles and those kinds ofthings.
Those are second.

Rick (18:52):
Yeah.
I can't agree more.
I mean, I can't tell you howlong I struggled with working a
full time job, knowing that Mymind was always somewhere else.
It was like, if I wasn'tcreating, if I wasn't pursuing
the passions that I knew kind ofmade me tick, voice acting,
writing, video editing, videocreating, whatever it was, even

(19:14):
music for that matter everymoment that I spent at a job
that forced me to stay in officewas a moment away from being who
I really was or who I really am.

Jesse (19:24):
Yeah,

Rick (19:25):
That is absolutely soul crushing.
Now it's like the more creativeyou are, doing things that you
don't, that mean nothing to you,are incredibly demoralizing.

Kaleem (19:37):
Yeah becomes a lot more difficult

Rick (19:39):
yeah.
And that's the struggle I thinka lot of people are dealing
with, so Workforce, it, you guyspublish, You know, articles from
some of the top remote workexperts, right?
What have been some of the mostpopular topics that are being
covered and, you know, thatpeople are looking for?
We'll be right back after thesewords.

(20:01):
2020 was no joke.
It changed the game foreveryone.
Workplace flexibility is nolonger a perk, but an
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In fact, a recent study showedthat a flexible schedule is more
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(20:25):
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(20:46):
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(21:36):
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All right, well that's a bitmuch, but for you, I'll do it.
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I'll tell your story the way youwant it told.
Follow along at RemotelyWeAreOneor visit my website at

(21:58):
rickhaney.
me for more information.
And now, back to the show.

Jesse (22:06):
yeah, it's interesting.
I'll answer the question 2 ways.
Right?
So the 1st thing is to say thatsome of our most popular
articles are the articles that Inever would have.
Guests would be popular.

Kaleem (22:16):
Really?

Jesse (22:17):
sure.
Well, not necessarily neverguessed that they would have
been popular.
I wouldn't have guessed thatthey would be our most popular
articles.
For example, 1 of our mostpopular articles has always
been, about remote jobs in theed tech space.
And

Kaleem (22:30):
Just specifically

Jesse (22:31):
ed tech.
Yeah.
Um, well, I think, there's acouple of things going on here.
One is tactical clean.
You and I have geeked out on theside talking about SEO and, our
wonderful friends, Google andall of the interesting things
that go into that soup.
Right?
And so part of it is tactical.
Part of it is learning as anoperator of a media company that

(22:52):
the more.
Precise you can get and specificyou can get in terms of the
topics and keywords that you'retrying to own, the better you're
going to do.
Right?
And so the simple reality isthat very few people were
publishing content about EdTechnumber 1 and about remote work
and EdTech number 2.
And so we were able to dominatethat space with that 1 article.
The broader answer Rick is, youknow, the long form version of

(23:16):
how we talk about workforce isthat workforce creates content
for people who work remotely orwant to work remotely and the
businesses that employ them andwe very intentionally.
And this especially was trueduring the early days of the
pandemic.
There was a ton of contentcreated.
Everybody was talking about it.
The New York Times, theWashington Post, Harvard
Business Review.

(23:36):
My observation was and is thatmost of that content is talking
about remote work and aboutremote workers.
And so we very intentionallyspeak to remote workers and 2
people who are trying to workremotely.
And so our content is tailoredto those individuals and to
those companies.
And so the content that does thebest.

(23:57):
The content that people engagewith the most is very practical.
How do you find a remote job inthe ed tech space for 1 example,
but also how do you how do youcraft?
A remote onboarding process,very specific stuff that, you
know, these larger publicationsthat are talking about the
remote work shift writ large, orthe economic impact of that

(24:18):
really aren't covering.
And so what we try to do is toget very practical, very
tactical and give.
Individuals tips on how to findjobs or work more effectively
remotely, but then especiallybusiness leaders and managers
how to lead their teamseffectively in this new
paradigm, I think, you know, andI'm sure we'll get into it in

(24:38):
future questions.
But like, what we're seeing nowis this, you know, the return to
office push and leaders tryingto do away with the carrot and
break out the stick and tryingto get people back into work.
I really see it as a failure ofmanagement, of leadership, of
not really learning how to workeffectively remotely, how to
lead effectively remotely.
And so we're trying toconstantly push out content that

(25:02):
speaks to that and helps peopleself educate in this new space.

Rick (25:06):
hmm.
That is so spot on.
You know, as I mentioned before,we talk about creating content
and I feel like lately thecontent that I have been
producing is, has beenspecifically targeting, you
know, as you mentioned in yourLinkedIn bio, the tyranny of

(25:26):
location, right?
Uh,

Jesse (25:28):
It's a deep cut, Rick.
I like that that resonated.
Thank you.
I'm glad.

Rick (25:31):
Oh my God, the whole, I'm telling you, Jesse, the whole
thing, every word of thatresonates with me.
You know, the designing ourcareers around our lives and not
vice versa.
I mean, this is the stuff that Iwant to produce because it
resonates with me.
It's been bogging me down for solong that I just feel like,
especially since the pandemic.

(25:52):
This is how everybody feels.
Everybody is stuck.
Everybody is like just sodesperate to break these chains
and I just I love your contentI'm so happy that I stumbled
upon your profile because I feellike our visions are synonymous
with one another so

Jesse (26:12):
Right.

Kaleem (26:13):
I got a question, Jesse, as far as, um, you know, you got
a chance to become a digitalnomad.
What was your experience liketrend transitioning to being
fully?
Fully mobile, should we say,trying to deal with internet,
trying to run a media company.
What were some of the surpriseuh ohs that you weren't prepared

(26:33):
for?

Jesse (26:33):
You said the main thing, internet connectivity, right?
back then we were, you know,this is in 2019 when we moved in
the Airstream, we were fullybased on cell signal.
And so there were a lot of timeswhere we'd be in the middle of
nowhere and have four bars.
And, you know, for me, I waslike, if I could get, like, 25
megabytes down and up, like,that was it was party time.

(26:54):
If that was what was going on.
And I knew that I could have azoom call if I could get, like,
6 up or down.
and so just really theconnectivity, I think was often
the biggest challenge for us.
And sometimes you would go toplaces, for example we decided
to spend a month in San Diego.
During the pandemic, for obviousreasons, if anybody's ever been

(27:14):
to San Diego, not such a badplace.
And so we booked a month at apretty posh, RV park on the bay
in San Diego.
We were less than a mile from I5and, we had unusable cell signal
on AT& T, and so, like, youknow, we had money, you know,
like, it's like paying rent, youknow what I mean?

(27:34):
Like, we planned to be there.
We had, you know, money and timeinvested in being in the space,
and, you know, you, you solvethe problem.
Like, we figured it out, we gota different SIM card.
But, that was a real challenge,connectivity, in going around.
I think that, you know, my wifewas consulting at the time too.
Now she's working a full timeremote gig.
But that was also early days ofworkforce.

(27:57):
And so I was on fire.
You know what I mean?
Like I was working, you know, 26hours a day, eating, sleeping,
brushing my teeth with thepassion of being an early days
founder.
And so the motivation piecewasn't hard, right?
Like it was easy to find time todo that work.
It was really more, you know,the tools of the trade and very
specifically internetconnectivity.

Kaleem (28:17):
Hmm.

Rick (28:17):
Oh,

Kaleem (28:18):
Yeah.
I can imagine that I would enjoythe mobility until, uh, I
couldn't connect and then I'd belosing my mind.
How do I

Rick (28:28):
yeah,

Kaleem (28:29):
I connect?

Rick (28:30):
you got to plug into the matrix.

Kaleem (28:32):
right, right.
I need the matrix.
I need to get in Neo.
Where are you?
Um, So as far as content goes,you obviously have your pulse on
this industry, right?
You have your pulse on it.
Cause I mean, the website'sgreat.
I love seeing all the articlescome from it.
I love it.
So keep doing your thing.
When speaking to businesses, youtalk about speaking to

(28:54):
businesses, speaking, maybe tomanagers.
What's the next thing of contentthat you feel Organizations and
managers need to hear or need toprepare for, you know, like what
are some good things?

Jesse (29:10):
Well, I, so I think, first of all, that's been the
evolution, or that's been themoving target.
And so, in the early days of,you know, pre pandemic, you had
a very small group of companiesand individuals who were leading
remotely, right?
And you could talk to them, youcould learn from them, they
could learn from each other.
When things blew up and we went,you know, overnight from 6

(29:30):
million people in 2019 to 60million people in 2020 working
remotely, it was a totallydifferent paradigm and people
were really trying to play catchup and it was really survival
mode.
And what I think the space thatwe're in now.
Is that pendulum is swingingback towards the office.
And so, you know, leaders aretrying to beg, borrow and steal

(29:53):
and get people to come back tothe office where they feel like
they have more knowledge andmore control over their
employees.
I think that, 1st of all, Ithink that the genies out of the
bottle, the cats out of the bag,whatever analogy you want to
use.
People have got a sense of thefreedom and benefits that come
from remote work and smartcompanies see the benefits

(30:14):
themselves.
Right?
Like, you think about Nvidia,Nvidia is the fastest growing by
a mile, company in terms ofmarket cap in the s and p 500.
In 2023.
They four Xed their stock priceand market cap, they're fully
remote.
They went fully remotereactively during the pandemic
and they saw all the benefits ofdoing that, and they chose to

(30:36):
proactively engage with it andembrace it.
And evolve in that direction.
I think some of the companiesthat you read about that are
really struggling with the shiftto remote or trying to get back
to office, you read aboutGoogle, you read about Microsoft
forcing people back to theoffice.
On the one hand, these are allcompanies, you know, Microsoft
is older than me.

(30:56):
And, you know, Facebook is 20plus years old.
I think at this point, right.
Or there about.
And so those companies wereconceived of and built in a
different time.
And so, of course they're gonnaswing back.
When I think Kaleem, I I alwaysthink about this and I shouldn't
probably quote it, but,'causethink it's attributed to bill
Gates, I think it's actually himwho said it.
He said that people alwaysoverestimate the amount of

(31:19):
change that happens in a yearand underestimate the amount of
change that happens a decade.
And I think that the companiesthat are being founded today.
Are by and large going to benatively remote, going to be
natively hybrid.
And in the next decade, we'regoing to start to see most of
these, the valuable companies,the companies that are coming
out in the AI space, the webfree space, they're all going to

(31:41):
be natively remote.
And so in 10 years, you know,remote is going to be the norm.
We're going to get past thisreturn to office.
Stuff for the industries whereit makes sense.
Like, I think that the office isalways going to have a place.
I love to work from an officewhen I get the opportunity to do
so.
You know what I mean?
Like, it's great.
I don't have to step away and dothe laundry, but so long way of
getting around back to yourquestion to me, it starts with

(32:03):
listening to your employees andwhat do your employees want and
then creating policies, sensiblepolicies that incentivize
employees to stay with yourcompany and to be remote.
And the fact is for the most ofthe leaders and managers who are
operating today, they grew up ina different time and they're
going back to what iscomfortable.

(32:23):
And so really, I think that interms of actual skills.
They need number one, thewillingness to embrace this
change, number two, some skillsto make that change work for
their business.
Right.
Some common sense, simple stuffto really be able to embrace
whatever it is, remote hybrid.
I have my own baggage around theterm hybrid, but you know,

(32:45):
flexible work, right.
And it's, it's really a simpleset of skills and how can these.
Leaders who are in place beginto adopt policies and processes
and procedures that enablepeople to work effectively
remotely.
I think long term talent alwayswins and the majority of the top
talent over time is going todemand to work flexibly and so

(33:10):
if companies want to succeedthey're going to have to embrace
flexibility because if they wantto attract top talent and win
over time, that's just going tobe the price you have to pay.

Kaleem (33:21):
makes sense.

Rick (33:23):
Well, let let's flip the script around a little bit to
the employee viewpoint.
Okay.
What advice would you give tosomebody who is feeling kind of
stuck in life?
They go to an office every day.
As I mentioned before, theirmind is in their heart and their
soul is somewhere else.
But they just don't know how toget started.
They don't know what skillsthey're gonna need.

(33:44):
They know where their passionsare, but they're so overwhelmed
they don't know where to start.
What would you recommend forsomeone like that?
To get into the remote, theremote industry?

Jesse (33:52):
Well, I would say in the first place and Rick, I'm kind
of going back to your story.
Like the thing that I didn'trealize that I realized probably
too late in life.
I wish I would have known thisin college is that, everything
that you see.
And you engage with in theworld, whether it's a podcast or
a video game or an iPad all ofthose things are a business and

(34:15):
an industry, you know what Imean?
Like people love to play videogames.
It's a pretty, pretty damn bigindustry.
You know what I mean?
Like you'd look at the blizzardActivision stuff, like.
There's lots of jobs to be hadin that industry.
And so if it is, if somebody whodoes feel stuck, you can look at
the things that you'repassionate about.
Like you said, you know,podcasting, if you're passionate
about podcasting, there's lotsof skills that you can acquire

(34:36):
to, to break into that space.
The second thing is I think.
This is something personal, it'shelpful and important for me to
take a long view and to say,where do I want to be in 10
years versus saying, what do Iwant my next job to be?
I think if you embrace that longview about where I want to be,
what I want my life and mycareer to look like in 10 years,

(34:58):
it makes it easier to make ashort term sacrifice and to say,
I'm going to stay in this job Idon't love, but you know what,
I'm going to take an audioediting class.
In the night, right?
To learn how to, you know, skillup to be in the podcasting
space.
It really is about acquiringskills.
And so, if you can take thatlong view and, map your skill
acquisition to the job you wantto have, you can really do some

(35:21):
pretty incredible things withyour career.
In the long and short term, andthat's regardless of the
remoteness or not of your job.
Right?
I think that, you know, that'sjust sort of like, maybe not
what you're looking for with theadvice.
But I think that, you know,people who feel stuck.
I think a lot of people whowhose companies are requiring
them to work 5 days in an officeprobably feel stuck.

(35:42):
And so if that's if you want toget out of that, Yeah.
the immediate thing might not beto look for a similar job title
at a similar company with aremote job.
You might do better if you takea long view and think about what
you want your life and yourcareer to look like in 10 years
and then work backwards fromthat.

Kaleem (35:56):
yeah,

Rick (35:56):
an answer.
Oh my gosh.
Talk about insightful.
I hope everybody heard that.

Kaleem (36:01):
that makes a lot of sense.
I never really thought of theidea of, not just automatically
applying to a job with yourtitle because what if that job
is not the thing that you wantto be doing?
And then, of course, it's thefamous.
Thought think about the longterm goal like that works for

(36:22):
everything.
We're always focused about howmuch you know i'm trying to drop
some weight or how much did Iweigh this week?
Well, how about at the end ofthe year?
Or you know, I want another jobwell think about your career,
you know, like staying in yourpart time or in your job, that
you're not liking and working onediting on the side That might

(36:42):
be a better career move, youknow, because you're acquiring
new skills.
So yeah, acquiring new skills isa great way to put it, man.
Thank you.

Rick (36:50):
Yeah.
Yeah.

Jesse (36:51):
stuff is out there.
And, you know, speaking ofremote tools and, there's never
been more, even just like, freevideos on YouTube or classes
that you can take remotely toskill up and in any of these
areas, whether it's, finance or,video editing, all this stuff is
like so widely available just interms of self education.
You, you know, people I thinkwould be shocked, but maybe not

(37:14):
because, you know, everybody'sgone to YouTube to learn how to
replace a light switch.
You can do that with yourcareer, too, you know what I
mean?
Like,

Kaleem (37:21):
Or how to be a brain surgeon.
I

Jesse (37:23):
Yeah, well, yeah, there are some clean.
You're right.
There are perhaps a few notableexceptions.
But, you know, I think there's alot that people can learn and
self educate and then take, youknow, virtual digital courses in
these other areas and reallysplit yourself up.
Certifications are a big deal,too.
So, being able to, you know, ifit's not in your current job

(37:45):
remit, you can getcertifications in the areas for
the jobs you want to have, notthe job you have.

Rick (37:49):
Fantastic.
Wow.
So.
Jesse, my friend.
do us do us a favor, would you?
Tell us about a comical or aninspiring moment you have had
while working remotely.

Kaleem (38:02):
Please do, sir.

Jesse (38:05):
well, the inspiring thing we sort of already talked about,
which is, I was able to, youknow, found and launch my
company, while working remotelyusing SIM card, cell signal,
across the United States.
And the specific moment that Icame to when you guys asked that
question, is that the day weactually launched workforce the
day we put the website live andwe got featured in a TechCrunch

(38:27):
article.
I was in a national park.
I was literally in a nationalpark.
We had a bunch of, you know,obviously stressful moments and
is the site functioning and allthis kind of thing.
And there were a few interviews.
He was around.
And so we were in it.
We're international park.
And, when the work day was done,my wife and I took the Chihuahua
on a hike.

(38:48):
And so that's.
Totally possible.
Like we did this, you know,using a SIM card and cell
signal.
And it's pretty, pretty robust,you know, media site.
Like, we've got all the thingsthat can go right and wrong with
that.
So, that's the thing thatinspires me in terms of kind of
anything is possible.
I think the funny thing, theironic thing, is Colleen, you
know, you're asking me aboutconnectivity and that was by far

(39:10):
our biggest frustration.
Number one challenge is therewere several times we would get
to a place that was beautifuland we realized we had no cell
signal and we couldn't staythere and we had to go, you
know, find some other place.
About three months after we soldthe Airstream and moved into
our, new condo in Austin,Starlink announced Starlink for
RVs and, uh, literally threemonths after, uh, And yeah, so,

(39:40):
um, that was,

Kaleem (39:42):
you saw, you sold the stream.
You sold the wind stream.
Oh

Jesse (39:49):
It had, it has a wonderful new home.
And they probably have Starlink,but you know, just like the
accumulated.
Anxiety and stress andfrustration about, you know, uh,
do we need to go get a VerizonSIM card?
Can we use the AT& T?
Do we have to break out the TMobile?
But the T Mobile, we only have acertain amount of minutes and,
you know, gigs on it.

(40:10):
I can't tell you the amount of,spiritual and intellectual time
that was wasted on this topic.
And, you know, three monthslater.
Starling for RVs, uh, you know,comes out on the site.
Anybody can get it.
And now, so now that's thething.
So the good news is that anybodywho wants to truly do the
digital nomad thing in an RV,they don't have to experience

(40:31):
any of the frustration, uh, thatI experienced, when I was doing
that.
So, good news for them.
Bad news for me.
Now I can laugh about that, butI was not laughing when I got
that email.

Kaleem (40:43):
That's hilarious.

Rick (40:44):
not.
Isn't it funny how thingshappen?
Sometimes it's not funny.
Not funny at all.

Kaleem (40:51):
Damn you, Elon!

Jesse (40:53):
yeah

Kaleem (40:54):
you always messing with my emotions, Elon?
Why?

Rick (41:00):
get you for this, Elon.
No,

Jesse (41:06):
side of a super villain

Kaleem (41:07):
The internet's out.
The internet's out.

Rick (41:12):
Jesse, where can our listeners and viewers find you?

Jesse (41:14):
Uh, you guys can find me easily on linkedin jesse
chambers.
I also Do try to respond tocomments and questions on
linkedin.
So that's the best place theycan also go to workforce.
Crucially, workforce, we spellworkforce with no O's, uh,
because offices are optional,get

Kaleem (41:32):
Oh,

Jesse (41:33):
Uh, so

Kaleem (41:34):
come on.
I never got this.
I never got this.
I never got this.

Jesse (41:39):
it's the start, it's the start to be, you know, no or few
vowels, spelling, but it'sworkforce.
com.
Workforce is spelled with noO's.

Kaleem (41:47):
awesome, bro.
How did I not know that?
Well, thanks man.
Really appreciate you.
It's always great to talk toyou, man Congratulations on the
success and you know, we'llcheck in back with you another
time Welcome anytime, bro.
Thank you

Rick (42:00):
to send you an invite to connect on LinkedIn right now
because,

Kaleem (42:03):
Yes, he is

Rick (42:04):
to you.
I have so many more questions.
So if I pepper you now and againon LinkedIn, don't be surprised.

Jesse (42:12):
I would be disappointed if you didn't, Rick.
It's been a lot of fun to talkwith you guys.
This has been one of the mostfun podcasts I've done.
But it's also, you know, it's areal honor to be here.
The list of past guests isreally inspiring.
And so thank you guys very muchfor the opportunity.
It's been a lot of fun.
I hope we can do it againsometime.

Rick (42:33):
Thanks, Jesse.

Kaleem (42:34):
later.
Peace.
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