May 13, 2024 • 52 mins
Chase Warrington established travel and international experiences as his guiding priorities early in his career, recognizing the necessity of making significant trade-offs to achieve these goals. After a brief period in the corporate sector, Chase joined Doist, a fully remote company with 100 employees spread across more than 30 countries. As the Head of Operations, he has taken a holistic approach to remote work best practices and has become a prominent figure in the remote work movement, which gained momentum during the COVID-19 pandemic in 2020. Chase and his family embarked on their international living adventure and are currently residing in Valencia, Spain.
In 2021, Chase launched the "About Abroad" podcast to offer advice and insights to those interested in living abroad. The podcast covers a wide range of topics from the mundane, such as visas and taxes, to more specific themes like Van Life and obtaining dual citizenship in various countries. Chase is an active presence in the community, frequently speaking at conferences and appearing as both a host and guest on numerous podcast episodes.
Please join me in welcoming Chase Warrington to this episode of Work 20XX.
I am thrilled that Chase accepted my invitation. His mission is to streamline the path to living and working abroad, making it smoother and less complicated than when he began his international journey over a decade ago.
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(00:01):
Sure, you already Chase?
I'm ready when you guys are.
Yeah. Let's do. It.
All right.
Hey, welcome back everybody.
Jeff Frick here, coming to youfrom the home studio
for another episode of Work 20XX.
And I'm really excitedabout this episode.
Our next guest has been in thisspace long before it was cool,
motivated by something a littlebit bigger than just remote work.
(00:22):
And so
He's a top voicein this space,
you hear, you see him all the time.
You read his writingall the time.
He's got a great podcast.
So we're excited to welcome infrom across the pond.
I thought from Valencia,but no, he's moved to Germany,
which shouldn'tsurprise me
because the man is on the move all the time.
He's Chase Warrington, the Head of Remote (now Operations) for Doist
and also the hostof About Abroad (Podcast).
(00:43):
Chase, great to see you
Jeff, it has been along time coming.
I am super excitedto be here.
I've checked out the podcast before
and you've had many friends
and colleaguesthat I respect on here.
So yeah, thank youfor having me.
It's great to see you.
My pleasure.
Thanks for acceptingthe invitation,
because you were certainlyone of the OGs in the space.
So I'm really excitedto have you on.
(01:03):
But let's,
do a little bit of background on,on the housekeeping.
So give people kind of the 101
on Doist what your, what your day job is.
Yeah, absolutely.
So, Doist is a software company,
we're predominantly known fortwo products that we produce
One is called Todoist,which is maybe the leading
task manager productivity app out there
(01:26):
it serves over40 million customers
in 19 different languages.
And, has been aroundfor 15 years or so.
And the other is Twist, which is a team communication platform
built specifically for,distributed teams.
I say that because we built it for ourselves.
at one point when we weren't happy
with some of the other tools on the market that weren't
focusing on async enough for us.
(01:48):
So, where we
I say that because
we're a team of about 100 people in 35 countries,
we span all time zones, and we've been remote first
since day one,dating back to 2009.
Believe it or not.
So, um it's,
the remote first-thing is, is in our DNA, and,
and that's what I get to work on every day.
(02:08):
My role as the,
has been the Head of Remotefor the last few years.
And I'm actually justas of the time of recording,
getting ready to transitioninto a new role
as Head of Operations,which will encompass
everything I was doing as head of remote, but
but a bit moreholistic viewpoints
still focused on makingdistributed work work
at a really high level.
(02:30):
And for the folks that don't know youor are just getting to know you.
You came to this because ofreally your passion about travel.
and the fact that, you know,there wasn't a lot of remote choices
ten years ago, 20 years ago.
Thanks Rob Sadow and the teamare helping people
find them easierwith the Flex Index.
But you decided early on in your,
like I don't wanna say careerjust in your life.
(02:51):
The travel was an important part of
of what you wanted to do
and what you want to see,
and have a slightly
kind of nontraditional view of the world.
I'm curious, you know, kind of
how did that come about?
I know it's kind of uniquebecause it was you and your wife.
It wasn't just a solo decisionthat you decided to do.
How did you kind of come to that,
prioritization that, you know,
(03:12):
we're going to make some trade offs because
travel is important to us.
Yeah, it's really interesting.my, the,
The evolution of my viewpoint and priorities
around remote workhave changed over
the 15 years of my career.
initially it was definitelyvery selfishly motivated.
It was like, I can't imaginesitting in a cubicle all day.
(03:34):
I know I'm going intothe business world.
and whatever regardthat meant at the time.
and I knew that remote work was possible,
even if it wasn't really popular.
It just felt like
this is where I'll actuallyget my best work done
when I have a change of scenery,
when I can control my day.
I know I'm a self-starter enough to
(03:55):
be able to manage my own time and energy, and
I think I'll be stifled.
I don't think I'll do very wellin that environment,
but yeah, and then on top of that, I,
I really had a desireto see the world
and those sacrificesactually dated back to
when I think onit now actually, I realize,
When I was in high school,I played American football
and it was likea core part of my life.
And I assumedI would go on to play in college.
(04:17):
And when I started going to visitcolleges, they all said
I’d planned to study abroadwhen I went to college.
it was a key part of what I wanted to do.
And every single coach told me,‘No’, you won't be able to do that
You'll have to be here.
You know, no season is good to go abroad.
Maybe you can godo a week or two.
But I wanted to do a semester,
and that was very stifling to me at the time.
I thought, like,it's a huge world.
(04:38):
You know, I'm not going toget to see any of it?
I've only got thesefour years. Right.
Because after that I have to go into the real world.
So I ended up passing up on
football scholarshipsto go travel instead,
and just realizedthat this was a core part
of what I had to havein my life, day to day.
And that transitioned into the professional world.
And then, yeah,over time, I mean
(04:59):
this is one of the reasons
why I'm so passionateabout this movement is because
I had to makevery serious sacrifices,
like huge trade offsin terms of salary,
company prestige,whatever it was.
I've calculated thatI've cut my salary by 50%
twice in my careerjust to have more flexibility
than was provided and,as the norm at the time.
(05:21):
And I don't think people should have to do that.
so, you know, advocatingfor any change that I can make
to push us in the directionof more flexibility,
while still maintaininga really high standards
in terms of your professional career is
is something that really resonates with me now and
I've got it.
I'm lucky I'm sittingwhere I want to be, but,
I know there's a lot of people out there
still having to fightfor that and so
(05:44):
It's fun to be a littlesmall part of that movement.
Yeah, 100 people in 35 countries.
I mean, what's the mostconcentration in any one country?
That's an amazingdistribution of people.
Yeah, if you do the math, it's funny.
It's like one, every third personis in a new country.
Right.
So it's we have
very little concentrationin any one place.
(06:04):
a lot of people assume it's the US.
I believe we have four or maybefive employees in the US.
we actually have a pretty strongconcentration in Europe.
The CEO and COOand CTO are all European.
So, we have a decentnumber of people in Portugal.
We have a few peoplein the UK.
(06:24):
and then it really getsvery scattered from there
2 or 3 inevery country.
And what,
Why did the founders go that way at the beginning?
What was kind ofthe impetus?
So it's funny, I think
Todoist as a product was built before the company Doist existed.
And Todoist was literally a side project
(06:45):
of our CEO and founderAmir (Salihefendic)
he just wanted
he didn't like the to do liststhat were out there.
So he built as a, you know, an engineer himself.
He said, I'm going to build my own.
And then people started asking if
they could pay for it.He ended up selling it.
All of a sudden hehad a company
and he needed to start hiring peopleto service those customers.
So he went on what's nowUpwork, Elance at the time,
(07:06):
hired some customer service repsto support his side project.
And then as the companyand product grew in popularity,
the team startedgrowing, too.
And he was, you know, realizing that he had hired
customer service repsfrom all around the world
without ever havingmet them.
in fact, one of them
(07:26):
didn't even meet until 13 or 14 years later.
and it just dawned on him,you know,
there's companies out therethat are operating this way.
he's a bit of a traveler himself
and has lived an international lifestyleand just said, you know,
I think I can do this,
learn from someof the best
that we're doing distributed work at a high level even back then
some of the early, the real real OGs and
(07:49):
and yeah,
then we decided, let's build a company around this.
So it's been afun ride.
Yeah.
Sounds a littlelike the Slack story,
but you guys didn't get sucked up into Salesforce.
so that probably worked outa little better,
but it is funny how like all the side projects and all the tools that
that people build internallyoften become,
you know,
the main product
(08:09):
beyond the one that they wereactually going to market with.
You know, it's not thatuncommon of a problem.
I’m sure you've talked to Brian Elliott about it ad nauseam
So let's get into some ofthe details about how to make,
remote work successful,distributed work teams successful
because you've been doing it for a long time,
and the tools weren'tnecessarily there before.
And I've listened to a numberof your podcasts
(08:32):
and a few your guests have said, you know, I know,
I know this is remote and I know what it feels like when it feels bad,
but what are some of the keys to doing it?
To doing it really wellphilosophically,
I think one of the first stepsis you know,
we throw this word ‘intentionality’around all the time
in this whole conversationaround remote work.
But I do think it's you know,it holds water because
(08:56):
you talk to so many leaders of teams
who have haphazardly gonethrough this transition.
Right?
And they've not really put a whole lot of thought and effort into the
the procedures and tooling and practices
and rituals that the team is going to do
and how those translateto the virtual first world
and even for us at Doist
you know having done this a really long time, the whole
the whole reason that my role as Head of Remote
(09:19):
came into existence,
was because we wantedto make sure that we stayed
on top of that transition time.
This was a pivotal moment.
There was a lot of new productsand services and tools
and best practicesbeing shared from teams
that were steppinginto this space.
And this had been a really strongpart of our company DNA
(09:39):
and a competitive advantage for us.
And we didn'twant to get lost in that.
And so, I mean,
you think aboutthe intentionality that
that our leadership team had to say,
you know, we're already likepretty good at remote work.
I mean, we've been doing this a long time.
At least we have someexperience, if nothing else.
but, you know,
we're going to be very intentional about making sure we stay
(10:00):
on top of thatand so
making sure that our toolsmatch what our values are,
making sure that we havethe right processes in place.
And we're constantlyevaluating these.
I'm currently working on a project right now
to revamp the whole waythat we move product
projects forward as a team,
and we've had the systemin place for years
and we've gone throughmultiple iterations of it, but
(10:20):
it has to match the way that we work
predominantly asynchronously.
you know, irrespectiveof time zones.
Very much so.And
And it has to match the way that we work
you know, so these things are like
it takes a lot of intentionalityto actually make it
come together and work at a high level.
(10:41):
so I do think it actually starts there.
And then what about takinga position to be a leader
in terms of communicatingbest practices
and really being, you know,kind of an industry leader?
We all know, Darren (Murph)
You know, the OG of them all.
And you've got a conceptthat you use all the time.
You talk about building‘Building in Public’
Why is that an important priorityfor the company versus
(11:02):
holding it back if it's a competitive advantage?
I had Jack Nilles on the other day and he said,
yeah, every time we had a customerwho was successful in remote work,
they're like, we're not telling anybody.
And you can't tell anybodyeither, because it's a
it's a competitive advantagethat we don't want to share.
So why philosophically,take the position and really
publish and be publicand be out there
(11:23):
in terms of taking a leadership position.
This ‘Build in Public’ mindset is something
I've fallen in love with.
The first chapter of my career was in,
financial services and looking, you know
somewhat corporate,I guess you would say,
and looking at spreadsheetswith large numbers on them and,
you know, strong competitionbetween your competitors and
not a lot ofbuilding in public,
(11:44):
I guess you would say
to boil it down,
and when I came overinto this space
and started working for Doist,
I really fell in love with this concept because
the root of this is that
we learn from the companies before usthat we're building in public.
Take, you know, 37signals Basecamp, for example.
We were learning a lot from them.
They were writing books on this.
They were, you know,sharing, blog or,
(12:07):
blog posts and participatingin interviews like this
sharing what theywere doing.
And that helped usbuild our business.
So I think there's somethingjust, you know,
holistically rooted in that,
that we're paying it forward in a way.
I also think you it's one of those situations
where, like, I know for me personally,
it's a selfish good deed in a lot of ways, like I
(12:27):
I put something out therethat we're doing,
something we're struggling with
or a failure that we had,or a success that we had.
And whatever I share,I probably get 5 or 10x back
in terms of feedback,questions,
thought provoking conversationsthat stem from that.
and a lot of thatwe take and we,
you know, build upon internally.
So I think there's two sides to it, but I've,
(12:49):
I truly have found like,I think I get way more back
from building in publicthan I give.
And so it's a fun flywheel to be caught up in.
It's a great lesson.
I mean, I'm out here inSilicon Valley and, you know,
people are always thinking of startup ideas
and often, you know, they want
to keep it secret, keep it secret.
I'm always like, listen,
no one is going to do your silly startup idea, right?
(13:10):
The the difficulty in doinganything well is the execution.
It's not the idea.The idea is the easy part.
And so,you know
the more you share your ideaswith other smart people,
like you said, and let themnoodle on it a little bit
and actually share real challengesand real questions.
You might be surprised at the a
at the answers and the input and, you know
getting other people's ideas because they're not going to copy you idea
(13:33):
There's so many pieces to the puzzle
to make a successful company from an idea.
It's a long way from
that first thing that got written down on the napkin.
It's actually funny, you saywritten down on the napkin because
that's the other.
Like exactly what you just said is correct.
In reality, like what we
when we look at our competitors, right
we produce a ‘to do’ listthat's done well in that space.
(13:56):
but our biggest competitoris pen and paper.
I mean, people, you know, people transitioning
from writing their to do list down on pen and paper
to converting to an app.
It’s not the other apps out there that are
in theory our direct competitors.
And so by us sharing moreabout how we're working,
I doubt very much that we're benefiting our direct competitors
(14:17):
as much as we are benefiting ourselves
by you know, putting our names out there
in front of the people who might be the pen and paper people.
So, yeah,I mean,
I've met lots of people along the waythat challenge this idea.
Like, it's not a good use of your time. It’s not
your there's no ROIon building in public.
but intangibly, I strongly believe that there is.
(14:38):
Oh for sure.
So one of the thingsthat you guys do, which,
if anyone's paying attention, you'll see,
is you guys have thesegreat retreats and
and you know,
Brian Elliot, another one of our friends,
you know, loves to say that
that remote doesn'tmean never together.
You got to get togetherand it’s still important.
So you guys gettogether frequently.
It looks like you're always in cool, dramatic,
(15:01):
beautiful locations.
Maybe it's jut the Italianlight in the photography.
I think in Tuscanyyou were recently at.
So I wonder if you can share
a little bit about the philosophyof how you get together
and how you think about itkind of budget wise.
as I think you've mentioned,
because you're not spendingmoney on real estate,
you're investing itin these retreats.
So how do youthink about retreats?
(15:21):
How did that kind of come about?
What's kind of the frequencyand some of the logistics?
Yeah, this is a corepart of making remote work
or distributed work work at a high level, in my opinion.
And you mentioned Brian Elliott.
It's funny,
I was just briefly with himlast week at Running Remote in,
in Lisbon, and I gave a presentation on,
(15:43):
that was titled ‘Remote First not Remote Only’
talking about our approachto remote work.
and I cited somestudies that Brian's done,
as well as others such as, you know,Raj (Choudhury) from Harvard and,
Annie Deanfrom Atlassian,
basically all telling a consistent narrative that
a) The teams that have adopted a virtual first
(16:05):
distributed mindset are,
almost unanimouslygathering in a physical space
on some level, some cadence,
and b) There are tangible,
like scientifically calculable,metrics that you can show
that there's a positivecorrelation to that time,
a lot of it based on connection,trust, bonds, friendships,
(16:29):
psychological safety,these sorts of things that are
that are just better developedin the co-located world.
The person that wants to,you know,
play devil's advocateagainst this would say,
Well, if that's where you build those bonds,
then why go through all the
blood, sweat and tears tobuild a distributed model?
when we've alreadygot the model that
“Works” in the you know, office based environment.
(16:51):
And so what we believe isthat we can have
we can in this way sort ofhave the best of both worlds.
we can have a distributed teamthat allows people
all the flexibility and benefits of having
the freedom to choosewhere they live
and work when it worksbest for them and their families.
and focus on deep work and
eliminate the commute and all the things that
(17:12):
everybody that listensto this podcast
already probably sees asbenefits of distributed work.
But then we can also bring peopletogether in a super meaningful,
and again, intentional way that serves all those other needs
that aren't as easy to facilitatein the virtual world.
And so we have this,you know, this great balance.
(17:33):
We do 2 to 3 meetups per year,depending on your
your preference,and which team you're on.
we do one all hands meeting,which we call ‘Doist Connect’ once a year
And then aboutsix months later
we have individual team off sites,that we call ‘Mini Retreats.’
And so every six months,at least, you have a retreat
to look forward towith your team.
And, upon, like,serving the team, you know,
(17:55):
do you want more of these,less of these?
It's almost unanimousthat twice per year,
maybe going to three times per year
Is the ideal number.
And you rotate thelocation all over the world.
We do, yeah so basically in
in each casemini retreats and Doist Connect.
It's a one week, like a five full day experience.
(18:18):
The Doist Connect rotates every year from location to location
which so far we haven'trepeated a country,
since starting these backin 2015, I believe.
And, you know, that could happen in the future,
but most likely will never repeata location anytime soon.
And thenfor the,
mini retreats, somethingwe've started doing
(18:40):
over the last couple of years,
we wanted to move towardsstandardizing these a bit more,
cutting out some of the proceduresand headache and workload
that goes into
creating them, because that's the real cost.
I mean, there's a financial cost,
but the real cost is inlabor and distraction.
So, we wanted to reduce thatas much as possible.
So what we did is we standardized, 15 cities.
(19:02):
We looked at where our teammates are located.
We looked at costsall these various factors,
and we picked 15 cities.
We built sample itineraries.
We've created,
relationships with venues and,
and facilitators and restaurantsand activities and such there.
And, so now we basically have like
our template down for these places so
(19:23):
teams can decide where they want to go.
We facilitate the whole thing,make sure that pretty much they,
you know, we're shooting for
‘retreats in two clicks’ is the goal.
we're not quite there.
But the idea is tomake it as quickly and,
painless as possible to curate these.
So one of thethings you do
and you mentioned itin another podcast,
is you talk about the 20, 30, 50 rule,
(19:46):
on these retreats, so that adds up to 100
And what percentage of your time20% - 30% - 50%
Now, if I was totell somebody,
walking down the streetthat the categories were
1) Work, 2) R and R (Rest and Recuperation)
and I’m trying to remember what the other one is
3) Activities,
They would probably think
that the 50% is businessyou guys all got together,
you don't see each otherevery six months.
So that's what you work on.
(20:07):
But no, it's completely flipped.
You only do 20% of the time on hard business tasks.
So I wonderif you could share
how did you get to this20, 30, 50?
And you know, kind of
clearly there’s some experience behind
why you've optimizedaround that kind of,
time allocation.
When you do spend the money and effort
(20:28):
to actually bring everybody together.
Yeah. It's a great question.
I mean, the natural inclination is to,
is to do exactlywhat you said, like,
if we're going to go through all of this effort
and spend all of these resources
on bringingpeople together,
we better get some bangfor our buck, right?
We better produce quite a bit.
And I totally get that.
And to be honest, like the 20/30/50 rule is a baseline,
(20:51):
like we want to kind ofstart from there,
but we scale it up and down as needed.
and certain off sites, require,you know, more,
more time spent on workor there's an opportunity
that just makes senseto tackle in that space.
So we'll work from there as needed.
But what we wanted to do is we
we wanted to move from being,
from naturally leaning into that inclination
(21:13):
to focus a lot on workjust because we're together
and really force us totime box that in,
to spend that time in a very meaningful way
and do activities that can't bedone in the virtual world.
And are really designedfor the co-located time together.
And what we foundis that you know
a) we're built to be a really productive,
(21:35):
asynchronous-firstremote-first team
that does really wellin that environment.
Like those are the type of people that we hire.
Those are the wayour processes are set up.
We've got everythingflowing in that direction.
And so whenwe came together,
we would do these,you know, early on
we would do theselong workshops
and we would, we would try
we flipped that paradigmupside down.
And we did alot of activity,
(21:56):
but we didn't necessarilyget a ton more out of it
than we would havehad we done it
in the normal waythat we work.
And so we thought like,
Is this the right wayto invest this time?
Because we'vealready identified
that the hardest partabout working,
in a distributed manner is,building those connections.
(22:16):
And that is the thing we can dobest when we're together.
So why wouldn't we usejust these two weeks?
I mean, we're talking 8 to 9,maybe ten days total per year.
Why wouldn't we kind of go all in on that?
And so it's not to saywe don't get anything done.
We do.
We're really effectivewith the 20%.
Or maybe it goes up to 30% or 40% sometimes.
(22:36):
But you know, when we
when we do lean into the work,
we plan it out well, it’s
it's optimized for the types of things we can't do
the other 50 weeks out of the year, and
and it works really well for us.
I think the other thingto mention here is like,
this is
like this isn't supposed to be
a suggestion for othersthat it's the right way for them.
(22:56):
It's just what's worked for us.
And a key part of thatis we are so distributed
that we can really only justifygetting together
two, maybe three times per year
if you're doing quarterly or if the cadence is a lot higher, maybe that
that number is different for you,
maybe also like your workis more collaborative in nature.
whereas the way we've set thingsup, like a lot of work happens,
(23:18):
in individual squads or teams
and a lot of thatcan be done virtually.
So I think it depends on the team though
the point that I would push back on is just like
really thinking through and fighting that natural inclination
to think just because we're together,
we have to get alot of stuff done.
Question if that's
actually what's happeningand if it's actually,
(23:39):
you know, the optimized wayto move forward.
I just love that.
What struck out to me,
listening to that storythe first time is that,
you know, like you said,
you've built systems and peopleand processes to get work
done in a certain way,which is predominantly async,
and not together.
And so then to, to put yourselves
all in a room and suddenlyflip your working method
(24:03):
and your productivity methodbecause you're together.
I mean, that's like, of courseit doesn't make any sense.
And the other piece too, isyou just said, you know,
are you really identifyingthe value that's happening there?
Brian Elliott, when he talks about his time
together with his team,he's very specific.
You know,we break bread together,
we volunteer together,we eat meals together.
We we do a lot of stuffthat's not work.
(24:25):
And I think reallywhat it gets to
that I think should be highlighted is it's this foundational building
of trust and relationship
that's going to enablethat productivity
and some of those hardconversations in difficult times
down the road.
So it's really foundationbuilding more than it is.
You know, let's kick outa beautiful three ring binder
of all the cool $#!+that we did here for three days.
(24:47):
Yeah, you nailed it.
I mean, someone came upto me recently and said, like,
so is your view on a retreat,
basically that it's just likea team vacation
and I they're,
I think their questionwas more like an assumption
that I would agree with that.
And, that'snot the case.
That's not what we're,we're advocating for.
(25:08):
or suggesting at all.
It's just about refocusingyour time and energy on
the connection bit.
And there's a lot of differentways you can create connection.
Probably most of all,
which is like connected tothe work that actually unites us.
So it's certainly not an indictmenton doing work together in person.
It's about just using that timeto do the type of work
(25:29):
that you can'tdo normally,
and then using the rest of the timeto build out those connections
in the ways that you can't doin your normal day to day.
and so like those examples that,
that Brian gavethat you just mentioned, like,
those areexcellent ways
to facilitateteam building and,
you know, buildtrue friendships that are,
that are just tough to do
in our hyper asyncremote-first environment.
(25:52):
Right.
So here's thecurveball, though,
is that you said that people don't have to attend,
if they don't want to
and there's ‘No Questions Asked’
So you've got this no questions asked attitude
It keeps coming upall over the place,
which to me reflectsa significant kind of
ninja level degree of trust,with people.
(26:15):
Because even though you saidthis is an important time
we're going to buildthese connections,
these 8 or 9 daysthat we're not,
out of the 365,
but we're not going to force youbecause we trust you.
And, if it doesn't work for you,it doesn't work.
No questions asked.
Wonder if you can share that
where that philosophy comes from
and how it's really worked outwhen you do trust people
(26:36):
that much.
Yeah, that's ait's a fair question.
I think it's rooted in the fact that we were built as a
remote-first, async-first teamfrom the beginning
and only later adopted retreats
five, six years into the company being built, so
Just on a pure like, humanto human fairness level,
it's like we hired you under these circumstances,
(26:58):
and now we have these new set of circumstances,
and we literally havepeople on the team who,
they just have zero desire to join in
on these kind of things.
They're not travelers, they’re
Flying scaresthem to death,
or they don't want to leave their families,
or they have sick loved onesnearby or whatever.
There's a variety of reasons.
and so, you know, we
(27:18):
we just decidedfrom the beginning, well
that's not, this isn't really the core of who we are.
What we do 50 weeksper year is really what dictates
who we hireand the type of people
we need to really surroundourselves with.
So let's see thisas a little bit extra.
That said, I think that this iscontroversial for a reason.
And if we're startingfrom scratch,
(27:40):
maybe, you know,I'm totally like,
I’ve never said this out loud or anything.
It's not a fully formulated thought, but
Perhaps if we were starting from scratch, that would
it would be more oflike a, an expectation
than it would a, you know,
a no questions asked sort of thing.
But we do take this approachto synchronous work of all forms.
I mean, again, we likewe built a team
(28:00):
that's predominantly workingin an async environment.
We have teammates working onopposite sides of the world.
We believe inthat separation.
And we want people to have their
their personal livesthat they have full control over.
So we don't even force peopleto attend synchronous meetings
if it's not convenientfor them,
so much less am I going to force someone to
to fly around the world to an event for a week
(28:22):
and, you know, leave their families behind
if it's not convenientfor them.
But I justI do think that, you know,
I know I have counterpartsat other companies
who take a very different stance on this.
And I actually get it
Like I 100% see where they're coming from.
but you know,
if you're going to bea part of this team,
you should come to these gatherings that we do.
It's a core part of how we build culture and such.
(28:44):
so I think there's a valid argument to be made there, it’s just the
This is the stancewe've taken and,
and it's worked outfine for us.
The other thing is like,
we havethis motto
of doing everything at a world class level at Doist
so when we, you know, write code or write a blog post or
service customers, we want to do itat a world class level.
And I take the same approachto our IRL strategy.
(29:07):
like we want our eventsto be world class events
that people reallylook forward to coming to
and they'reproud to come to.
So it shouldn't feel like this,like mundane meeting
that you just haveto go attend or
They’re experiences that you look forward to.
And because of that, we have a90% to 95% participation rate,
which in this spaceis like really, really high,
(29:27):
especially consideringour distribution.
So thisisn't a problem.
You know, we don't have20% of the team opting out.
and so almost everyonethat can be there is there.
And the few that don't,
it's usually for likehealth or family reasons.
Yeah.
And I love that when you listlike all those reasons
there's just so many little variablesthat could impact my availability
for this particular week.
(29:48):
And I think you've saidin some other of your shows that,
you know, maybe people miss oneor miss two, but,
you know, it'susually not a pattern.
It's because they have some,
some thing that's happeningthat just is preventing it.
But like you said,make it attractive.
So they want to goif it's
possible.
I want to shift gears a littlebit and talk about the tooling
and the tool space.
You just got back from Running Remote all the,
(30:11):
bummed Iwasn’t there.
Everybody else was there.
but one of the thingsNick Bloom likes to talk about,
you know, is,as this has taken off
and as it's becomemore mainstream,
you know, there'sjust investment.
into tools, into the processes
that enable remote work
for a lot more than companies like yours
that are new.
And there's a lot more people coming into it.
I wonder if you can share
(30:31):
some of the latest that came outof the Running Remote.
You were just there, you know,kind of your thought on tools?
not so much competitive tools,maybe competitive tools, but more
just kind of how the toolinginfrastructure and,
and the kind of enablinginfrastructure is changing
to make it easier to actuallybe able to execute this.
I think this is like one of the
(30:52):
like under the radar.
I don't know if it's,
maybe I would be curiousto hear what you think,
but it's almost like an under the radar benefit
of this whole transitionand explosion of,
distributed work being adopted is that
there's an explosion of tools that have been
developed to service that market.
And whether you're, you know,fully remote, like we are
(31:14):
or you're, you know,on a hybrid team of some sort.
I mean, there's tools that are developed,
being developedto serve that market.
And I think that'sreally fascinating.
an example of this,like over the last year or so,
we decided we've had,like many teams, you know,
we've mentioned some of themtoday, like GitLab and Darren,
for example, at GitLab,like writing the handbook
(31:36):
that they had, the epic handbook that they have.
Like we also have a company handbook.
It's got aroundlike 1,200 pages in it.
We've been working on itfor many years and
but we had kind of hacked it together.
It wasn't really like a greattool solution for all the teams
and on our
all the teams within the company.
And we decided, like, we couldwe could do better than this.
and like when we startedto look at the market for like,
(31:57):
okay, what are thereany products out there
that service this specifically?
Yeah, there werelike 15 of them now
There's a ton of options.
and, you know, just for something very specific,
like a distributed team handbookproduct, you know, and so,
I just find this, like, reallyas someone who, who's
wants to see this become moreadopted on a wide scale.
(32:18):
I love seeing that,
there's solutions out there to,to solve those pain points.
So, I'm seeing a lotin that space.
I mean, there's a lot,of course,
you know, connected to AIand then filtering down,
I feel like AI’s sort ofat the top of the,
the umbrella and thenfiltering down from there,
it's like, how do we,
consolidatecommunication?
How do we find documentationand content a lot easier?
(32:40):
How do we filter out
get to the fewest numberof stakeholders and people
who have to participate in anygiven asynchronous conversation?
And then the other area thatI think is really interesting is,
it's like coming backto connection.
There's some really interestingtools emerging to,
to help support virtual connection and,
strengthen tighter, deeper bondswith your async
(33:02):
or remote first team, which is also pretty fascinating.
Yeah.
We haven't talked about itmuch because, I don't know,
maybe it's too obvious.
We've been in the space too long or
or talking to Darren too many times, but,
you know, clearly async,
as a methodology and a philosophy
and documentation, you know,are two of the core tenets.
You talked aboutintentionality.
I think those are thethe big three words that,
(33:25):
that really setthis whole thing down.
and if you don't do that.
So I'm just curious what happensin an emergency session.
Yeah we do.
So we do have an emergency.
you know, channelthat you can get to
get to people in a,real emergency.
Basically, it's like an emergency team
that's set up and with a separate Telegram space
where like, notificationsare turned on.
(33:47):
And so if we need to get topeople, you know,
I think it's happenedonce or twice.
in the eight yearsthat I've been here
that, you know,that needed to be used.
But the truth is, with the withwe're set up, I mean,
we have somebody working 24 hours a day.
we have people spread around all time zones.
So there's, it's very rarethat something happens that we,
that we don't havesomebody set up for,
(34:08):
you know, to be able to handle that.
Yeah.
It's such a greatwhen you talk about,
you know, one of the otherkind of unlocks
is better meeting cultureand doing meetings better.
But you guys have likebasically no meetings.
You have like two hoursof meetings, a work
a week, which frees up,
okay, just do easy math, 38 hoursof productive heads down time.
I mean, the
(34:28):
the productivity efficiency
by not being interrupted constantly
and having that as kind ofa corporate standard.
I mean, I can't even ask youabout meetings
because you guys don't
even have enough meetingsto have a good meeting culture.
Yeah, we kind of suck at it, to be honest.
I mean, it's funny.
We're kind of terrible at meetings.
it's I mean,I say that
(34:48):
somewhat joking, but also,
like, funny enough, we'vementioned Darren a few times,
like a couple of years ago atRunning Remote in Montreal.
I sat on a panel with Darren,
Stephanie Lee and Sam Fisher.
all three, all four of us were somewhere
in the head ofremote space,
and we went after the panel.
We were standing backstage
(35:09):
and we were talking aboutsome of the
the pain pointsthat we feel on our team.
And I was the one like,
we need more synchronicity,you know, we need more meetings.
We need.
And they're trying to pushthe number of meetings
and the number of hoursspent in meetings down.
but an interesting conclusion
we came to there was like,
you know, meetings are a powerful tool.
If they're used properly.
but and in our case, you know,particularly at that time,
(35:32):
we weren't using meetings enoughto ever be good at hosting them.
And so it was almost like,
you know, an unintentional downside.
We had leaned so hard intoasynchronous communication
that we had gotten badat using this
otherwise really powerful tool.
Of course, a lot of teamsgo in the opposite direction
and, you know, they're it'slike if that tool is a hammer,
(35:54):
they're just using the hammerfor like every job, you know, and
and so we needed toto balance that out a little bit.
And I think we, we have
we’re using synchronous communication
a little bit more.
We're recognizing like there's,there's a great space for
both synchronousand also the, that,
that bit of spacein between,
which is like, you know,using voice notes more and using
(36:17):
products like Loom,for asynchronous video more.
And, just providing alittle bit more context
than the written wordcan do sometimes,
even if you can't actuallysync up for a meeting. But,
Yeah, I still would like to see us get better at the
the meeting thing
and without a whole lot ofpractice that can be tough.
Yeah, well there's alsokind of that interim thing
(36:39):
which is like chat and IM and DM and you know, can you
can you get something done injust a quick, you know, 15 word,
exchange on a couple of IMs,which again,
it's kind of tough because you get the interruption
factor if you make that standard.
But you know, a lot of timesthings can get done
a lot quicker and efficientlywithout a meeting.
(37:00):
Even if it is some typeof synchronous or just,
you know, go old school,pick up the phone and,
and call somebody if the time works out great
Crazy idea right.
Yeah.
But it's crazybecause
companies have been distributed for so long.
This is not new.
It's just, you know,kind of the formality of it.
But, you know, I'msure most people's
teams were pretty distributed in 2019
(37:22):
when you actually hada team meeting.
You needed to get everybodyon the phone as
as Kate, you know, Lister would say
nine floors, nine buildingsor nine time zones.
You know, nobody's sitting nextto the people they work with.
These are all big globalinternational organizations.
Crazy.
That's right.
Yep.
Yeah, that's I mean,
something I found really interestingjust before this call, I had,
(37:43):
kind of I'm doing like a seriesof internal interviews
with people about the projectmanagement system that we use to
to move projectsforward and sprints.
And we're, we're doing some revamps to that and so
Just talking withsome people
from different areasof the company
about their pain pointsand such and,
and this and
during this discussion with one of our engineers,
she said, you know,we had been going round and round
(38:04):
asynchronouslyfor over a week
on this technical specthat we were writing,
and just running into a roadblock.
And, and finally
we hopped on a call
and we ironed it outin an hour
and the inclinationthere is to think like, okay.
Yeah. See, that's why meetingswork and that's true.
That is whenmeetings work.
But on the flip side,like our M.O., the like
(38:27):
the way we're going to defaultis first to async.
And nine times out of ten,
like this was the anomaly for her.
It was like the first timein many years
that she had hit that pointwhere it was like
async just wasn't working.
And so that works reallywell for us.
Like we start with async andthen when things aren't working,
we switch to sync.
And I think
a lot of
(38:47):
you still see a lot of teams
going in the opposite direction
where everything defaults to sync.
And then,
you know, maybe occasionally you,
you sprinkle in somethingasynchronously.
but we're all still learning
how to find the right balance between these.
And it's a moving target.
because the tooling changes,the situation changes.
And, you know, we're,
we're trying to standardize those things.
But at the same time,like, you know,
(39:08):
leaving room for flexibilitygiven the situation.
Right
Well, not to mentionwhen you had that meeting,
everyone was so clued in towhat the issues were after,
however manywhat period of time, you know,
exchanging ideas and the ideationand the conflicts
and what the issues were.
I mean, I'm sure the levelof preparedness
of the people and the engagementin the issue of the people
(39:30):
in that meetingwas probably very high.
Instead of, oh my gosh,
I have to attendanother status meeting,
which I have nothingto contribute to,
and it's keeping me from allthe work that I have to do.
Yes, that's it, it was 90%of the way done at that point.
You know, theyhopped on one hour,
solved the whole thing and like,you know, moved on.
So in either case,the work got done in a week.
(39:51):
you know, but,
but instead of spendingfour hours a day in meetings
to get there, they, you know,they did it asynchronously, so
I don't know, it'snot it's not all like
I think one of the thingsthat I'm learning
more and more as I getdeeper into this space is like,
it's not all or nothing,you know,
it's not remote firstor office based.
(40:11):
It's not 100% async or 100% synchronous.
There's this spectrum
that teams have to choose wherethey want to sit on that spectrum
and just being cognizant of thatand building your
your whole infrastructure aroundwhere you've decided to sit on
that spectrumis really important.
And again, like we'reconstantly tweaking this and
and moving those dials to,to make it work best for us.
(40:33):
That's great.
So I want to shift gears
another time and talk about your podcast,
‘About Abroad’ because you came at this
really from the traveler,point of view.
And, you know,you've done the van life.
I think you've donea couple tours on the van,
on the van life, experienceand how many?
Give us a quick update.
I mean, you've been doing thisfor how many?
(40:54):
How many episodes?
How many seasons?It's amazing.
Oh. Thank you.
Yeah. Well, as a,
you know, I'm a podcast hostthat respects the podcast host
that I'm talking to,so I appreciate that.
it's, a yeah,
I'm in my ninth season
of ‘About Abroad’ now, and I really started it
as a side project, a little bitof like personal context.
(41:16):
I'm from the U.Sand I have lived like,
you know, permanently
in a handful of countriesaround the world and,
most recentlyspent almost the last
better part of the lastseven years living in Spain
and have been traveling around Europe
for the last couple of years,
spending some time,several months
in different countriesaround Europe.
So this is sort of a core partof my personal life.
(41:41):
And, and I started ‘About Abroad’ really
because I was having a tonof side conversations with people
as the explosion of remote workwas happening
and you know, matchedwith my experience navigating
the complexities of beingan expat in different countries,
dealing with visa stuff,bureaucracy, taxes, all the,
(42:01):
the not so fun partsthat don't show up on your
Instagram accounts.
dealing with all those.
There were lots of conversations taking place,
and I thought, you know,when I started this,
there wasn't a whole lot of content out there about how to do it.
I mean, I was really, like,
navigating it in the dark, andit was complex and challenging.
And so I thought, I lovehaving these conversations.
I'm a podcast junkie and we'realready having them off the air.
(42:25):
What if we just record themand share with people,
what these experiences are like, and so
it sort of expandedinto a whole.
The space that we're talking
about is kind of generallyfocused on global mobility.
so it's not just like boringvisa and bureaucracy stuff.
It's also telling people'sstories about
how they managed to move abroad or
or how their, you know, traveling permanently.
(42:47):
and a lot of it touches onremote work, which,
which powers a large percentageof those people's stories.
But it's so it's interesting, as you said,
the extremes are not necessary anymore.
And you, Nick bloom,I think in is TED Talk
puts up a slide
when you used to Google ‘remote work’,
and there's kind of two categories of
pictures and the images that would come up.
(43:07):
when you see it,
one is like the lazy slob hanging out,
not getting dressed in the house,
you know, a stone's throw awayfrom the fridge, and the TV.
And then the other oneis the people
in beautiful tropical locationswith a laptop on their lap,
and a nice fruity drink with an umbrella.
And then, of course,the punchline is the fruity
The umbrella is actually a Wi-Fi antenna.
(43:31):
it's helping theperson get in.
You know, it used to bea pretty extreme thing,
but now, as you said, it'snot necessarily so extreme.
You don't have to be so extreme.
You don't have to do it full time.
And I'm curious, how has thethe paper work in kind of the,
the nasty, ugly stuffthat you do have to take care of
in terms oftaxes and visas.
And, you know, it's
(43:51):
not the sexy stuff on Instagram, but it's the stuff
to get to those, fancy Instagram pictures.
So I wonder if you could sharehow that world has changed.
for people thinking aboutpart time, a little bit,
maybe a year, you know,or maybe it's an extended,
you know, kind of vacationor mid midlife retirement,
you know for, to go spend a yearin Tuscany or whatever.
(44:13):
Yeah.
It’s an awesome question
because this is thethis is today's reality.
That was not the realityfive years ago.
and much less ten years ago,
it used to be
extremely difficultto find a country
that would want to accept you,if you weren't a citizen,
or if you didn't have some sortof, like, real need to move there
(44:34):
like work was bringing you there
marriage wasbringing you there.
you know, a refugee statusor something like that.
The options were very limited
and mostly you were restricted to
you know, 90 day or60 day tourist type visas,
maybe one year, like astudent visa or something.
but these days,
I mean, they're literally
I've talked to the people behind the scenes
(44:54):
who are creating these digital nomad visas.
They look at us like
we at Doist look at users of our products.
I mean, they're trying to build features and attract you
to their countries.
They're literallyfighting over you
to bring you here.
And they've paved a very clearand easy path to get there.
and so, you know, it'sa lot easier than it used to be.
(45:15):
And there's in a lot of cases, it's,
not even a questionas to whether or not you'll
you'll be approved.
It's just a matter ofdo you check 3 or 4 boxes?
you know, do you have a little bit of incometo support yourself or savings?
Do you have a cleanbackground check?
And, do you have a, you know, a doctor
that will say you're not,you know, deathly ill?
And if thoseare the cases, then,
(45:36):
there's a lot of countriesthat will accept you for a year
or up to five yearsand even provide
like a permanent path to citizenship, or permanent residency.
So, yeah, it's changed a lot,
with the emergenceof digital nomad visas.
And on the flip side,
it can never be understatedhow painful the,
the processes are,
because they're always a lotharder than they look.
(45:58):
I'm a big advocateof hiring a professional to,
to help you navigate this space.
It's relativelyinexpensive,
and is super helpful,like
someone that just knows the local ropesand can walk you through it. So,
yeah, we talk about thisa lot on the podcast, honestly.
Like, we have individual episodesfor individual digital nomad visas
or countries that you might be specific in
(46:20):
specifically interested in,
people who in our space
that we've talked to a lot, Jeff,that have have done that and,
you know, are living abroad in
Portugal or Ecuadoror wherever it may be.
And, so we're tryingto tell their stories
and explain how they navigated that space.
Yeah. It's great.
I was listening to the episode with the guy,
talking about getting your Italian,
(46:41):
your Italian citizenshipif you got Italian ancestry.
So I’m gonna
I shared that one with the family.
And what he said
it takes years and years.
So let's get to be friends.
But, you know,we'll get you there eventually.
Well Chase, this has been great.
I want to wrapkind of on the last topic,
your advice for people that just feel like,
you know, the standard pathdoesn't necessarily feel good
or just doesn't fit,
(47:02):
or I think I'm looking for something different.
I love your experienceof your corporate thing.
When I interviewed at a Fortune,
I don't know what they areFortune 50 company
and I went andit was great interview
and we went and we sat down
and the guy got this little floor plan
office plan out with allthe desks and the cubes.
And he's like, yeah, you'regoing to be right here
(47:24):
And I literally I mean, even now
I just, my stomach just turned over.
I'm like, I'm going to be there like?
And all these little squares,you know, like I go there.
And then my first job in tech at Intel, at RNB, the Robert Noyce Building
main headquarters.
Six foot cubes, seas of them.
And then, you know, all the support columns
(47:45):
have labels, either, you know, a letter or a number.
So, Chase, you're at pole G6,the printers at A2.
I'll meet you, over at Brian'sdesk at, you know, H4.
And I just it's just like, Aahh
So for people that feel likethat’s not the way, you know,
I don't want to followthe pattern.
You didn't,
You saw a different path.
(48:07):
You set a different priority.
You made conscious trade offsand thankfully found a partner
who had aligned incentives.
What do you tell people?
That, hey, if it doesn'tfeel like the standard path
is the right path,there is an alternate.
You know there are alternativesand you can make it happen.
Yeah, I think you justsummarized it really well.
You know, I have toldmany people
(48:29):
that I've had that conversation with that in
in my early days of my career.
I decided that was going to be my North Star,
that freedom and flexibility were, you know,
going to be a part of my career.
And I was going to prioritize that over all else.
And so, you know,that means
(48:49):
inherently making some sacrifices
and I kind of have like a little
it sounds a little bitoverly ambitious,
and I don't think I can actuallyhave a huge impact on this,
on this goal, but it's a little bitof a goal of mine to like,
make sure that people don't have to
make those sacrifices and trade offs anymore.
trade offs anymore.
and so, you know,
collectively, I think there's a lot of people working towards that.
(49:12):
But it may mean still that at some point
you have to makesome sort of sacrifice.
It may mean a step back
in your career trajectory,it may mean a slight pay cut.
It may mean taking a job,
working at somethingthat isn't exactly aligned
with what you want to do.
But if you see it asone step back
two steps forward, and look at the long term path,
rather than, you know,
instant gratification,this is what I need right now.
(49:34):
Then I think you're setting yourself up for
for long term success
More ideally, like, I hopethat's not the case for you.
I hope you canjust take the
take the path forwardthat, you know,
check all the boxesthat you want
and move forward
in a into a companythat accepts you
because the truth is, is that there's
it's never been easier than it is right now.
There's more options out therethan there ever have been.
(49:57):
When I found Doist,my wife found
the job that I got hired at Doist forby looking at a Pinterest board
that had 75 jobs, 75 companieshiring from anywhere,
and it was the only thingwe had ever seen like this.
And of those 75,I think 73 were engineering jobs.
And, you know,I'm not an engineer.
(50:17):
So I thought,oh, I'm kind of screwed.
I looked at those two jobs,I applied for the one at Doist
and I ended up getting it.
But I tell that storybecause
that was all we could find on that at that time.
I can probably name you, like 75 dedicated job boards
just for distributed work.
Flexible work right now.
so there's so many optionsavailable to you right now
(50:37):
if you're feelingbeaten down by this,
I just there are positions out there.
It's never been easier.
And then if you're willingto make a little sacrifice
if needed because that's your North Star,
then I think you have,you know,
you have a bright futureahead of you.
That's great.
Well, Chase,I think we'll leave it at that.
That's great advicefor people.
And you are changing the world.
(50:58):
You aresetting the pace.
You know, you'reyou're sharing your stories.
You're out there a lot.
You publish a lot,you talk a lot.
You share great guests, so
I think you're making an impact for sure.
Thanks, Jeff.
I appreciate itlikewise.
appreciate allthat you're doing.
And I love listening to theguests you bring on here.
So hopefully we added a little value today.
And, it was a lot of funfor me, so I appreciate it.
(51:21):
Great.
Well, thanks for coming onI appreciate it.
All right.
He's Chase, I'm Jeffyou're watching Work 20XX
Thanks for watching.
Thanks for listeningon the podcast.
We'll see you next time.
Take care.
Awesome.
Awesome.
That was great, man.
Sure, you already Chase?
I'm ready when you guys are.
Yeah. Let's do. It.
All right.
Hey, welcome back everybody.
Jeff Frick here, coming to youfrom the home studio
for another episode of Work 20XX.
And I'm really excitedabout this episode.
Our next guest has been in thisspace long before it was cool,
motivated by something a littlebit bigger than just remote work.
(00:22):
And so
He's a top voicein this space,
you hear, you see him all the time.
You read his writingall the time.
He's got a great podcast.
So we're excited to welcome infrom across the pond.
I thought from Valencia,but no, he's moved to Germany,
which shouldn'tsurprise me
because the man is on the move all the time.
He's Chase Warrington, the Head of Remote (now Operations) for Doist
and also the hostof About Abroad (Podcast).
(00:43):
Chase, great to see you
Jeff, it has been along time coming.
I am super excitedto be here.
I've checked out the podcast before
and you've had many friends
and colleaguesthat I respect on here.
So yeah, thank youfor having me.
It's great to see you.
My pleasure.
Thanks for acceptingthe invitation,
because you were certainlyone of the OGs in the space.
So I'm really excitedto have you on.
(01:03):
But let's,
do a little bit of background on,on the housekeeping.
So give people kind of the 101
on Doist what your, what your day job is.
Yeah, absolutely.
So, Doist is a software company,
we're predominantly known fortwo products that we produce
One is called Todoist,which is maybe the leading
task manager productivity app out there
(01:26):
it serves over40 million customers
in 19 different languages.
And, has been aroundfor 15 years or so.
And the other is Twist, which is a team communication platform
built specifically for,distributed teams.
I say that because we built it for ourselves.
at one point when we weren't happy
with some of the other tools on the market that weren't
focusing on async enough for us.
(01:48):
So, where we
I say that because
we're a team of about 100 people in 35 countries,
we span all time zones, and we've been remote first
since day one,dating back to 2009.
Believe it or not.
So, um it's,
the remote first-thing is, is in our DNA, and,
and that's what I get to work on every day.
(02:08):
My role as the,
has been the Head of Remotefor the last few years.
And I'm actually justas of the time of recording,
getting ready to transitioninto a new role
as Head of Operations,which will encompass
everything I was doing as head of remote, but
but a bit moreholistic viewpoints
still focused on makingdistributed work work
at a really high level.
(02:30):
And for the folks that don't know youor are just getting to know you.
You came to this because ofreally your passion about travel.
and the fact that, you know,there wasn't a lot of remote choices
ten years ago, 20 years ago.
Thanks Rob Sadow and the teamare helping people
find them easierwith the Flex Index.
But you decided early on in your,
like I don't wanna say careerjust in your life.
(02:51):
The travel was an important part of
of what you wanted to do
and what you want to see,
and have a slightly
kind of nontraditional view of the world.
I'm curious, you know, kind of
how did that come about?
I know it's kind of uniquebecause it was you and your wife.
It wasn't just a solo decisionthat you decided to do.
How did you kind of come to that,
prioritization that, you know,
(03:12):
we're going to make some trade offs because
travel is important to us.
Yeah, it's really interesting.my, the,
The evolution of my viewpoint and priorities
around remote workhave changed over
the 15 years of my career.
initially it was definitelyvery selfishly motivated.
It was like, I can't imaginesitting in a cubicle all day.
(03:34):
I know I'm going intothe business world.
and whatever regardthat meant at the time.
and I knew that remote work was possible,
even if it wasn't really popular.
It just felt like
this is where I'll actuallyget my best work done
when I have a change of scenery,
when I can control my day.
I know I'm a self-starter enough to
(03:55):
be able to manage my own time and energy, and
I think I'll be stifled.
I don't think I'll do very wellin that environment,
but yeah, and then on top of that, I,
I really had a desireto see the world
and those sacrificesactually dated back to
when I think onit now actually, I realize,
When I was in high school,I played American football
and it was likea core part of my life.
And I assumedI would go on to play in college.
(04:17):
And when I started going to visitcolleges, they all said
I’d planned to study abroadwhen I went to college.
it was a key part of what I wanted to do.
And every single coach told me,‘No’, you won't be able to do that
You'll have to be here.
You know, no season is good to go abroad.
Maybe you can godo a week or two.
But I wanted to do a semester,
and that was very stifling to me at the time.
I thought, like,it's a huge world.
(04:38):
You know, I'm not going toget to see any of it?
I've only got thesefour years. Right.
Because after that I have to go into the real world.
So I ended up passing up on
football scholarshipsto go travel instead,
and just realizedthat this was a core part
of what I had to havein my life, day to day.
And that transitioned into the professional world.
And then, yeah,over time, I mean
(04:59):
this is one of the reasons
why I'm so passionateabout this movement is because
I had to makevery serious sacrifices,
like huge trade offsin terms of salary,
company prestige,whatever it was.
I've calculated thatI've cut my salary by 50%
twice in my careerjust to have more flexibility
than was provided and,as the norm at the time.
(05:21):
And I don't think people should have to do that.
so, you know, advocatingfor any change that I can make
to push us in the directionof more flexibility,
while still maintaininga really high standards
in terms of your professional career is
is something that really resonates with me now and
I've got it.
I'm lucky I'm sittingwhere I want to be, but,
I know there's a lot of people out there
still having to fightfor that and so
(05:44):
It's fun to be a littlesmall part of that movement.
Yeah, 100 people in 35 countries.
I mean, what's the mostconcentration in any one country?
That's an amazingdistribution of people.
Yeah, if you do the math, it's funny.
It's like one, every third personis in a new country.
Right.
So it's we have
very little concentrationin any one place.
(06:04):
a lot of people assume it's the US.
I believe we have four or maybefive employees in the US.
we actually have a pretty strongconcentration in Europe.
The CEO and COOand CTO are all European.
So, we have a decentnumber of people in Portugal.
We have a few peoplein the UK.
(06:24):
and then it really getsvery scattered from there
2 or 3 inevery country.
And what,
Why did the founders go that way at the beginning?
What was kind ofthe impetus?
So it's funny, I think
Todoist as a product was built before the company Doist existed.
And Todoist was literally a side project
(06:45):
of our CEO and founderAmir (Salihefendic)
he just wanted
he didn't like the to do liststhat were out there.
So he built as a, you know, an engineer himself.
He said, I'm going to build my own.
And then people started asking if
they could pay for it.He ended up selling it.
All of a sudden hehad a company
and he needed to start hiring peopleto service those customers.
So he went on what's nowUpwork, Elance at the time,
(07:06):
hired some customer service repsto support his side project.
And then as the companyand product grew in popularity,
the team startedgrowing, too.
And he was, you know, realizing that he had hired
customer service repsfrom all around the world
without ever havingmet them.
in fact, one of them
(07:26):
didn't even meet until 13 or 14 years later.
and it just dawned on him,you know,
there's companies out therethat are operating this way.
he's a bit of a traveler himself
and has lived an international lifestyleand just said, you know,
I think I can do this,
learn from someof the best
that we're doing distributed work at a high level even back then
some of the early, the real real OGs and
(07:49):
and yeah,
then we decided, let's build a company around this.
So it's been afun ride.
Yeah.
Sounds a littlelike the Slack story,
but you guys didn't get sucked up into Salesforce.
so that probably worked outa little better,
but it is funny how like all the side projects and all the tools that
that people build internallyoften become,
you know,
the main product
(08:09):
beyond the one that they wereactually going to market with.
You know, it's not thatuncommon of a problem.
I’m sure you've talked to Brian Elliott about it ad nauseam
So let's get into some ofthe details about how to make,
remote work successful,distributed work teams successful
because you've been doing it for a long time,
and the tools weren'tnecessarily there before.
And I've listened to a numberof your podcasts
(08:32):
and a few your guests have said, you know, I know,
I know this is remote and I know what it feels like when it feels bad,
but what are some of the keys to doing it?
To doing it really wellphilosophically,
I think one of the first stepsis you know,
we throw this word ‘intentionality’around all the time
in this whole conversationaround remote work.
But I do think it's you know,it holds water because
(08:56):
you talk to so many leaders of teams
who have haphazardly gonethrough this transition.
Right?
And they've not really put a whole lot of thought and effort into the
the procedures and tooling and practices
and rituals that the team is going to do
and how those translateto the virtual first world
and even for us at Doist
you know having done this a really long time, the whole
the whole reason that my role as Head of Remote
(09:19):
came into existence,
was because we wantedto make sure that we stayed
on top of that transition time.
This was a pivotal moment.
There was a lot of new productsand services and tools
and best practicesbeing shared from teams
that were steppinginto this space.
And this had been a really strongpart of our company DNA
(09:39):
and a competitive advantage for us.
And we didn'twant to get lost in that.
And so, I mean,
you think aboutthe intentionality that
that our leadership team had to say,
you know, we're already likepretty good at remote work.
I mean, we've been doing this a long time.
At least we have someexperience, if nothing else.
but, you know,
we're going to be very intentional about making sure we stay
(10:00):
on top of thatand so
making sure that our toolsmatch what our values are,
making sure that we havethe right processes in place.
And we're constantlyevaluating these.
I'm currently working on a project right now
to revamp the whole waythat we move product
projects forward as a team,
and we've had the systemin place for years
and we've gone throughmultiple iterations of it, but
(10:20):
it has to match the way that we work
predominantly asynchronously.
you know, irrespectiveof time zones.
Very much so.And
And it has to match the way that we work
you know, so these things are like
it takes a lot of intentionalityto actually make it
come together and work at a high level.
(10:41):
so I do think it actually starts there.
And then what about takinga position to be a leader
in terms of communicatingbest practices
and really being, you know,kind of an industry leader?
We all know, Darren (Murph)
You know, the OG of them all.
And you've got a conceptthat you use all the time.
You talk about building‘Building in Public’
Why is that an important priorityfor the company versus
(11:02):
holding it back if it's a competitive advantage?
I had Jack Nilles on the other day and he said,
yeah, every time we had a customerwho was successful in remote work,
they're like, we're not telling anybody.
And you can't tell anybodyeither, because it's a
it's a competitive advantagethat we don't want to share.
So why philosophically,take the position and really
publish and be publicand be out there
(11:23):
in terms of taking a leadership position.
This ‘Build in Public’ mindset is something
I've fallen in love with.
The first chapter of my career was in,
financial services and looking, you know
somewhat corporate,I guess you would say,
and looking at spreadsheetswith large numbers on them and,
you know, strong competitionbetween your competitors and
not a lot ofbuilding in public,
(11:44):
I guess you would say
to boil it down,
and when I came overinto this space
and started working for Doist,
I really fell in love with this concept because
the root of this is that
we learn from the companies before usthat we're building in public.
Take, you know, 37signals Basecamp, for example.
We were learning a lot from them.
They were writing books on this.
They were, you know,sharing, blog or,
(12:07):
blog posts and participatingin interviews like this
sharing what theywere doing.
And that helped usbuild our business.
So I think there's somethingjust, you know,
holistically rooted in that,
that we're paying it forward in a way.
I also think you it's one of those situations
where, like, I know for me personally,
it's a selfish good deed in a lot of ways, like I
(12:27):
I put something out therethat we're doing,
something we're struggling with
or a failure that we had,or a success that we had.
And whatever I share,I probably get 5 or 10x back
in terms of feedback,questions,
thought provoking conversationsthat stem from that.
and a lot of thatwe take and we,
you know, build upon internally.
So I think there's two sides to it, but I've,
(12:49):
I truly have found like,I think I get way more back
from building in publicthan I give.
And so it's a fun flywheel to be caught up in.
It's a great lesson.
I mean, I'm out here inSilicon Valley and, you know,
people are always thinking of startup ideas
and often, you know, they want
to keep it secret, keep it secret.
I'm always like, listen,
no one is going to do your silly startup idea, right?
(13:10):
The the difficulty in doinganything well is the execution.
It's not the idea.The idea is the easy part.
And so,you know
the more you share your ideaswith other smart people,
like you said, and let themnoodle on it a little bit
and actually share real challengesand real questions.
You might be surprised at the a
at the answers and the input and, you know
getting other people's ideas because they're not going to copy you idea
(13:33):
There's so many pieces to the puzzle
to make a successful company from an idea.
It's a long way from
that first thing that got written down on the napkin.
It's actually funny, you saywritten down on the napkin because
that's the other.
Like exactly what you just said is correct.
In reality, like what we
when we look at our competitors, right
we produce a ‘to do’ listthat's done well in that space.
(13:56):
but our biggest competitoris pen and paper.
I mean, people, you know, people transitioning
from writing their to do list down on pen and paper
to converting to an app.
It’s not the other apps out there that are
in theory our direct competitors.
And so by us sharing moreabout how we're working,
I doubt very much that we're benefiting our direct competitors
(14:17):
as much as we are benefiting ourselves
by you know, putting our names out there
in front of the people who might be the pen and paper people.
So, yeah,I mean,
I've met lots of people along the waythat challenge this idea.
Like, it's not a good use of your time. It’s not
your there's no ROIon building in public.
but intangibly, I strongly believe that there is.
(14:38):
Oh for sure.
So one of the thingsthat you guys do, which,
if anyone's paying attention, you'll see,
is you guys have thesegreat retreats and
and you know,
Brian Elliot, another one of our friends,
you know, loves to say that
that remote doesn'tmean never together.
You got to get togetherand it’s still important.
So you guys gettogether frequently.
It looks like you're always in cool, dramatic,
(15:01):
beautiful locations.
Maybe it's jut the Italianlight in the photography.
I think in Tuscanyyou were recently at.
So I wonder if you can share
a little bit about the philosophyof how you get together
and how you think about itkind of budget wise.
as I think you've mentioned,
because you're not spendingmoney on real estate,
you're investing itin these retreats.
So how do youthink about retreats?
(15:21):
How did that kind of come about?
What's kind of the frequencyand some of the logistics?
Yeah, this is a corepart of making remote work
or distributed work work at a high level, in my opinion.
And you mentioned Brian Elliott.
It's funny,
I was just briefly with himlast week at Running Remote in,
in Lisbon, and I gave a presentation on,
(15:43):
that was titled ‘Remote First not Remote Only’
talking about our approachto remote work.
and I cited somestudies that Brian's done,
as well as others such as, you know,Raj (Choudhury) from Harvard and,
Annie Deanfrom Atlassian,
basically all telling a consistent narrative that
a) The teams that have adopted a virtual first
(16:05):
distributed mindset are,
almost unanimouslygathering in a physical space
on some level, some cadence,
and b) There are tangible,
like scientifically calculable,metrics that you can show
that there's a positivecorrelation to that time,
a lot of it based on connection,trust, bonds, friendships,
(16:29):
psychological safety,these sorts of things that are
that are just better developedin the co-located world.
The person that wants to,you know,
play devil's advocateagainst this would say,
Well, if that's where you build those bonds,
then why go through all the
blood, sweat and tears tobuild a distributed model?
when we've alreadygot the model that
“Works” in the you know, office based environment.
(16:51):
And so what we believe isthat we can have
we can in this way sort ofhave the best of both worlds.
we can have a distributed teamthat allows people
all the flexibility and benefits of having
the freedom to choosewhere they live
and work when it worksbest for them and their families.
and focus on deep work and
eliminate the commute and all the things that
(17:12):
everybody that listensto this podcast
already probably sees asbenefits of distributed work.
But then we can also bring peopletogether in a super meaningful,
and again, intentional way that serves all those other needs
that aren't as easy to facilitatein the virtual world.
And so we have this,you know, this great balance.
(17:33):
We do 2 to 3 meetups per year,depending on your
your preference,and which team you're on.
we do one all hands meeting,which we call ‘Doist Connect’ once a year
And then aboutsix months later
we have individual team off sites,that we call ‘Mini Retreats.’
And so every six months,at least, you have a retreat
to look forward towith your team.
And, upon, like,serving the team, you know,
(17:55):
do you want more of these,less of these?
It's almost unanimousthat twice per year,
maybe going to three times per year
Is the ideal number.
And you rotate thelocation all over the world.
We do, yeah so basically in
in each casemini retreats and Doist Connect.
It's a one week, like a five full day experience.
(18:18):
The Doist Connect rotates every year from location to location
which so far we haven'trepeated a country,
since starting these backin 2015, I believe.
And, you know, that could happen in the future,
but most likely will never repeata location anytime soon.
And thenfor the,
mini retreats, somethingwe've started doing
(18:40):
over the last couple of years,
we wanted to move towardsstandardizing these a bit more,
cutting out some of the proceduresand headache and workload
that goes into
creating them, because that's the real cost.
I mean, there's a financial cost,
but the real cost is inlabor and distraction.
So, we wanted to reduce thatas much as possible.
So what we did is we standardized, 15 cities.
(19:02):
We looked at where our teammates are located.
We looked at costsall these various factors,
and we picked 15 cities.
We built sample itineraries.
We've created,
relationships with venues and,
and facilitators and restaurantsand activities and such there.
And, so now we basically have like
our template down for these places so
(19:23):
teams can decide where they want to go.
We facilitate the whole thing,make sure that pretty much they,
you know, we're shooting for
‘retreats in two clicks’ is the goal.
we're not quite there.
But the idea is tomake it as quickly and,
painless as possible to curate these.
So one of thethings you do
and you mentioned itin another podcast,
is you talk about the 20, 30, 50 rule,
(19:46):
on these retreats, so that adds up to 100
And what percentage of your time20% - 30% - 50%
Now, if I was totell somebody,
walking down the streetthat the categories were
1) Work, 2) R and R (Rest and Recuperation)
and I’m trying to remember what the other one is
3) Activities,
They would probably think
that the 50% is businessyou guys all got together,
you don't see each otherevery six months.
So that's what you work on.
(20:07):
But no, it's completely flipped.
You only do 20% of the time on hard business tasks.
So I wonderif you could share
how did you get to this20, 30, 50?
And you know, kind of
clearly there’s some experience behind
why you've optimizedaround that kind of,
time allocation.
When you do spend the money and effort
(20:28):
to actually bring everybody together.
Yeah. It's a great question.
I mean, the natural inclination is to,
is to do exactlywhat you said, like,
if we're going to go through all of this effort
and spend all of these resources
on bringingpeople together,
we better get some bangfor our buck, right?
We better produce quite a bit.
And I totally get that.
And to be honest, like the 20/30/50 rule is a baseline,
(20:51):
like we want to kind ofstart from there,
but we scale it up and down as needed.
and certain off sites, require,you know, more,
more time spent on workor there's an opportunity
that just makes senseto tackle in that space.
So we'll work from there as needed.
But what we wanted to do is we
we wanted to move from being,
from naturally leaning into that inclination
(21:13):
to focus a lot on workjust because we're together
and really force us totime box that in,
to spend that time in a very meaningful way
and do activities that can't bedone in the virtual world.
And are really designedfor the co-located time together.
And what we foundis that you know
a) we're built to be a really productive,
(21:35):
asynchronous-firstremote-first team
that does really wellin that environment.
Like those are the type of people that we hire.
Those are the wayour processes are set up.
We've got everythingflowing in that direction.
And so whenwe came together,
we would do these,you know, early on
we would do theselong workshops
and we would, we would try
we flipped that paradigmupside down.
And we did alot of activity,
(21:56):
but we didn't necessarilyget a ton more out of it
than we would havehad we done it
in the normal waythat we work.
And so we thought like,
Is this the right wayto invest this time?
Because we'vealready identified
that the hardest partabout working,
in a distributed manner is,building those connections.
(22:16):
And that is the thing we can dobest when we're together.
So why wouldn't we usejust these two weeks?
I mean, we're talking 8 to 9,maybe ten days total per year.
Why wouldn't we kind of go all in on that?
And so it's not to saywe don't get anything done.
We do.
We're really effectivewith the 20%.
Or maybe it goes up to 30% or 40% sometimes.
(22:36):
But you know, when we
when we do lean into the work,
we plan it out well, it’s
it's optimized for the types of things we can't do
the other 50 weeks out of the year, and
and it works really well for us.
I think the other thingto mention here is like,
this is
like this isn't supposed to be
a suggestion for othersthat it's the right way for them.
(22:56):
It's just what's worked for us.
And a key part of thatis we are so distributed
that we can really only justifygetting together
two, maybe three times per year
if you're doing quarterly or if the cadence is a lot higher, maybe that
that number is different for you,
maybe also like your workis more collaborative in nature.
whereas the way we've set thingsup, like a lot of work happens,
(23:18):
in individual squads or teams
and a lot of thatcan be done virtually.
So I think it depends on the team though
the point that I would push back on is just like
really thinking through and fighting that natural inclination
to think just because we're together,
we have to get alot of stuff done.
Question if that's
actually what's happeningand if it's actually,
(23:39):
you know, the optimized wayto move forward.
I just love that.
What struck out to me,
listening to that storythe first time is that,
you know, like you said,
you've built systems and peopleand processes to get work
done in a certain way,which is predominantly async,
and not together.
And so then to, to put yourselves
all in a room and suddenlyflip your working method
(24:03):
and your productivity methodbecause you're together.
I mean, that's like, of courseit doesn't make any sense.
And the other piece too, isyou just said, you know,
are you really identifyingthe value that's happening there?
Brian Elliott, when he talks about his time
together with his team,he's very specific.
You know,we break bread together,
we volunteer together,we eat meals together.
We we do a lot of stuffthat's not work.
(24:25):
And I think reallywhat it gets to
that I think should be highlighted is it's this foundational building
of trust and relationship
that's going to enablethat productivity
and some of those hardconversations in difficult times
down the road.
So it's really foundationbuilding more than it is.
You know, let's kick outa beautiful three ring binder
of all the cool $#!+that we did here for three days.
(24:47):
Yeah, you nailed it.
I mean, someone came upto me recently and said, like,
so is your view on a retreat,
basically that it's just likea team vacation
and I they're,
I think their questionwas more like an assumption
that I would agree with that.
And, that'snot the case.
That's not what we're,we're advocating for.
(25:08):
or suggesting at all.
It's just about refocusingyour time and energy on
the connection bit.
And there's a lot of differentways you can create connection.
Probably most of all,
which is like connected tothe work that actually unites us.
So it's certainly not an indictmenton doing work together in person.
It's about just using that timeto do the type of work
(25:29):
that you can'tdo normally,
and then using the rest of the timeto build out those connections
in the ways that you can't doin your normal day to day.
and so like those examples that,
that Brian gavethat you just mentioned, like,
those areexcellent ways
to facilitateteam building and,
you know, buildtrue friendships that are,
that are just tough to do
in our hyper asyncremote-first environment.
(25:52):
Right.
So here's thecurveball, though,
is that you said that people don't have to attend,
if they don't want to
and there's ‘No Questions Asked’
So you've got this no questions asked attitude
It keeps coming upall over the place,
which to me reflectsa significant kind of
ninja level degree of trust,with people.
(26:15):
Because even though you saidthis is an important time
we're going to buildthese connections,
these 8 or 9 daysthat we're not,
out of the 365,
but we're not going to force youbecause we trust you.
And, if it doesn't work for you,it doesn't work.
No questions asked.
Wonder if you can share that
where that philosophy comes from
and how it's really worked outwhen you do trust people
(26:36):
that much.
Yeah, that's ait's a fair question.
I think it's rooted in the fact that we were built as a
remote-first, async-first teamfrom the beginning
and only later adopted retreats
five, six years into the company being built, so
Just on a pure like, humanto human fairness level,
it's like we hired you under these circumstances,
(26:58):
and now we have these new set of circumstances,
and we literally havepeople on the team who,
they just have zero desire to join in
on these kind of things.
They're not travelers, they’re
Flying scaresthem to death,
or they don't want to leave their families,
or they have sick loved onesnearby or whatever.
There's a variety of reasons.
and so, you know, we
(27:18):
we just decidedfrom the beginning, well
that's not, this isn't really the core of who we are.
What we do 50 weeksper year is really what dictates
who we hireand the type of people
we need to really surroundourselves with.
So let's see thisas a little bit extra.
That said, I think that this iscontroversial for a reason.
And if we're startingfrom scratch,
(27:40):
maybe, you know,I'm totally like,
I’ve never said this out loud or anything.
It's not a fully formulated thought, but
Perhaps if we were starting from scratch, that would
it would be more oflike a, an expectation
than it would a, you know,
a no questions asked sort of thing.
But we do take this approachto synchronous work of all forms.
I mean, again, we likewe built a team
(28:00):
that's predominantly workingin an async environment.
We have teammates working onopposite sides of the world.
We believe inthat separation.
And we want people to have their
their personal livesthat they have full control over.
So we don't even force peopleto attend synchronous meetings
if it's not convenientfor them,
so much less am I going to force someone to
to fly around the world to an event for a week
(28:22):
and, you know, leave their families behind
if it's not convenientfor them.
But I justI do think that, you know,
I know I have counterpartsat other companies
who take a very different stance on this.
And I actually get it
Like I 100% see where they're coming from.
but you know,
if you're going to bea part of this team,
you should come to these gatherings that we do.
It's a core part of how we build culture and such.
(28:44):
so I think there's a valid argument to be made there, it’s just the
This is the stancewe've taken and,
and it's worked outfine for us.
The other thing is like,
we havethis motto
of doing everything at a world class level at Doist
so when we, you know, write code or write a blog post or
service customers, we want to do itat a world class level.
And I take the same approachto our IRL strategy.
(29:07):
like we want our eventsto be world class events
that people reallylook forward to coming to
and they'reproud to come to.
So it shouldn't feel like this,like mundane meeting
that you just haveto go attend or
They’re experiences that you look forward to.
And because of that, we have a90% to 95% participation rate,
which in this spaceis like really, really high,
(29:27):
especially consideringour distribution.
So thisisn't a problem.
You know, we don't have20% of the team opting out.
and so almost everyonethat can be there is there.
And the few that don't,
it's usually for likehealth or family reasons.
Yeah.
And I love that when you listlike all those reasons
there's just so many little variablesthat could impact my availability
for this particular week.
(29:48):
And I think you've saidin some other of your shows that,
you know, maybe people miss oneor miss two, but,
you know, it'susually not a pattern.
It's because they have some,
some thing that's happeningthat just is preventing it.
But like you said,make it attractive.
So they want to goif it's
possible.
I want to shift gears a littlebit and talk about the tooling
and the tool space.
You just got back from Running Remote all the,
(30:11):
bummed Iwasn’t there.
Everybody else was there.
but one of the thingsNick Bloom likes to talk about,
you know, is,as this has taken off
and as it's becomemore mainstream,
you know, there'sjust investment.
into tools, into the processes
that enable remote work
for a lot more than companies like yours
that are new.
And there's a lot more people coming into it.
I wonder if you can share
(30:31):
some of the latest that came outof the Running Remote.
You were just there, you know,kind of your thought on tools?
not so much competitive tools,maybe competitive tools, but more
just kind of how the toolinginfrastructure and,
and the kind of enablinginfrastructure is changing
to make it easier to actuallybe able to execute this.
I think this is like one of the
(30:52):
like under the radar.
I don't know if it's,
maybe I would be curiousto hear what you think,
but it's almost like an under the radar benefit
of this whole transitionand explosion of,
distributed work being adopted is that
there's an explosion of tools that have been
developed to service that market.
And whether you're, you know,fully remote, like we are
(31:14):
or you're, you know,on a hybrid team of some sort.
I mean, there's tools that are developed,
being developedto serve that market.
And I think that'sreally fascinating.
an example of this,like over the last year or so,
we decided we've had,like many teams, you know,
we've mentioned some of themtoday, like GitLab and Darren,
for example, at GitLab,like writing the handbook
(31:36):
that they had, the epic handbook that they have.
Like we also have a company handbook.
It's got aroundlike 1,200 pages in it.
We've been working on itfor many years and
but we had kind of hacked it together.
It wasn't really like a greattool solution for all the teams
and on our
all the teams within the company.
And we decided, like, we couldwe could do better than this.
and like when we startedto look at the market for like,
(31:57):
okay, what are thereany products out there
that service this specifically?
Yeah, there werelike 15 of them now
There's a ton of options.
and, you know, just for something very specific,
like a distributed team handbookproduct, you know, and so,
I just find this, like, reallyas someone who, who's
wants to see this become moreadopted on a wide scale.
(32:18):
I love seeing that,
there's solutions out there to,to solve those pain points.
So, I'm seeing a lotin that space.
I mean, there's a lot,of course,
you know, connected to AIand then filtering down,
I feel like AI’s sort ofat the top of the,
the umbrella and thenfiltering down from there,
it's like, how do we,
consolidatecommunication?
How do we find documentationand content a lot easier?
(32:40):
How do we filter out
get to the fewest numberof stakeholders and people
who have to participate in anygiven asynchronous conversation?
And then the other area thatI think is really interesting is,
it's like coming backto connection.
There's some really interestingtools emerging to,
to help support virtual connection and,
strengthen tighter, deeper bondswith your async
(33:02):
or remote first team, which is also pretty fascinating.
Yeah.
We haven't talked about itmuch because, I don't know,
maybe it's too obvious.
We've been in the space too long or
or talking to Darren too many times, but,
you know, clearly async,
as a methodology and a philosophy
and documentation, you know,are two of the core tenets.
You talked aboutintentionality.
I think those are thethe big three words that,
(33:25):
that really setthis whole thing down.
and if you don't do that.
So I'm just curious what happensin an emergency session.
Yeah we do.
So we do have an emergency.
you know, channelthat you can get to
get to people in a,real emergency.
Basically, it's like an emergency team
that's set up and with a separate Telegram space
where like, notificationsare turned on.
(33:47):
And so if we need to get topeople, you know,
I think it's happenedonce or twice.
in the eight yearsthat I've been here
that, you know,that needed to be used.
But the truth is, with the withwe're set up, I mean,
we have somebody working 24 hours a day.
we have people spread around all time zones.
So there's, it's very rarethat something happens that we,
that we don't havesomebody set up for,
(34:08):
you know, to be able to handle that.
Yeah.
It's such a greatwhen you talk about,
you know, one of the otherkind of unlocks
is better meeting cultureand doing meetings better.
But you guys have likebasically no meetings.
You have like two hoursof meetings, a work
a week, which frees up,
okay, just do easy math, 38 hoursof productive heads down time.
I mean, the
(34:28):
the productivity efficiency
by not being interrupted constantly
and having that as kind ofa corporate standard.
I mean, I can't even ask youabout meetings
because you guys don't
even have enough meetingsto have a good meeting culture.
Yeah, we kind of suck at it, to be honest.
I mean, it's funny.
We're kind of terrible at meetings.
it's I mean,I say that
(34:48):
somewhat joking, but also,
like, funny enough, we'vementioned Darren a few times,
like a couple of years ago atRunning Remote in Montreal.
I sat on a panel with Darren,
Stephanie Lee and Sam Fisher.
all three, all four of us were somewhere
in the head ofremote space,
and we went after the panel.
We were standing backstage
(35:09):
and we were talking aboutsome of the
the pain pointsthat we feel on our team.
And I was the one like,
we need more synchronicity,you know, we need more meetings.
We need.
And they're trying to pushthe number of meetings
and the number of hoursspent in meetings down.
but an interesting conclusion
we came to there was like,
you know, meetings are a powerful tool.
If they're used properly.
but and in our case, you know,particularly at that time,
(35:32):
we weren't using meetings enoughto ever be good at hosting them.
And so it was almost like,
you know, an unintentional downside.
We had leaned so hard intoasynchronous communication
that we had gotten badat using this
otherwise really powerful tool.
Of course, a lot of teamsgo in the opposite direction
and, you know, they're it'slike if that tool is a hammer,
(35:54):
they're just using the hammerfor like every job, you know, and
and so we needed toto balance that out a little bit.
And I think we, we have
we’re using synchronous communication
a little bit more.
We're recognizing like there's,there's a great space for
both synchronousand also the, that,
that bit of spacein between,
which is like, you know,using voice notes more and using
(36:17):
products like Loom,for asynchronous video more.
And, just providing alittle bit more context
than the written wordcan do sometimes,
even if you can't actuallysync up for a meeting. But,
Yeah, I still would like to see us get better at the
the meeting thing
and without a whole lot ofpractice that can be tough.
Yeah, well there's alsokind of that interim thing
(36:39):
which is like chat and IM and DM and you know, can you
can you get something done injust a quick, you know, 15 word,
exchange on a couple of IMs,which again,
it's kind of tough because you get the interruption
factor if you make that standard.
But you know, a lot of timesthings can get done
a lot quicker and efficientlywithout a meeting.
(37:00):
Even if it is some typeof synchronous or just,
you know, go old school,pick up the phone and,
and call somebody if the time works out great
Crazy idea right.
Yeah.
But it's crazybecause
companies have been distributed for so long.
This is not new.
It's just, you know,kind of the formality of it.
But, you know, I'msure most people's
teams were pretty distributed in 2019
(37:22):
when you actually hada team meeting.
You needed to get everybodyon the phone as
as Kate, you know, Lister would say
nine floors, nine buildingsor nine time zones.
You know, nobody's sitting nextto the people they work with.
These are all big globalinternational organizations.
Crazy.
That's right.
Yep.
Yeah, that's I mean,
something I found really interestingjust before this call, I had,
(37:43):
kind of I'm doing like a seriesof internal interviews
with people about the projectmanagement system that we use to
to move projectsforward and sprints.
And we're, we're doing some revamps to that and so
Just talking withsome people
from different areasof the company
about their pain pointsand such and,
and this and
during this discussion with one of our engineers,
she said, you know,we had been going round and round
(38:04):
asynchronouslyfor over a week
on this technical specthat we were writing,
and just running into a roadblock.
And, and finally
we hopped on a call
and we ironed it outin an hour
and the inclinationthere is to think like, okay.
Yeah. See, that's why meetingswork and that's true.
That is whenmeetings work.
But on the flip side,like our M.O., the like
(38:27):
the way we're going to defaultis first to async.
And nine times out of ten,
like this was the anomaly for her.
It was like the first timein many years
that she had hit that pointwhere it was like
async just wasn't working.
And so that works reallywell for us.
Like we start with async andthen when things aren't working,
we switch to sync.
And I think
a lot of
(38:47):
you still see a lot of teams
going in the opposite direction
where everything defaults to sync.
And then,
you know, maybe occasionally you,
you sprinkle in somethingasynchronously.
but we're all still learning
how to find the right balance between these.
And it's a moving target.
because the tooling changes,the situation changes.
And, you know, we're,
we're trying to standardize those things.
But at the same time,like, you know,
(39:08):
leaving room for flexibilitygiven the situation.
Right
Well, not to mentionwhen you had that meeting,
everyone was so clued in towhat the issues were after,
however manywhat period of time, you know,
exchanging ideas and the ideationand the conflicts
and what the issues were.
I mean, I'm sure the levelof preparedness
of the people and the engagementin the issue of the people
(39:30):
in that meetingwas probably very high.
Instead of, oh my gosh,
I have to attendanother status meeting,
which I have nothingto contribute to,
and it's keeping me from allthe work that I have to do.
Yes, that's it, it was 90%of the way done at that point.
You know, theyhopped on one hour,
solved the whole thing and like,you know, moved on.
So in either case,the work got done in a week.
(39:51):
you know, but,
but instead of spendingfour hours a day in meetings
to get there, they, you know,they did it asynchronously, so
I don't know, it'snot it's not all like
I think one of the thingsthat I'm learning
more and more as I getdeeper into this space is like,
it's not all or nothing,you know,
it's not remote firstor office based.
(40:11):
It's not 100% async or 100% synchronous.
There's this spectrum
that teams have to choose wherethey want to sit on that spectrum
and just being cognizant of thatand building your
your whole infrastructure aroundwhere you've decided to sit on
that spectrumis really important.
And again, like we'reconstantly tweaking this and
and moving those dials to,to make it work best for us.
(40:33):
That's great.
So I want to shift gears
another time and talk about your podcast,
‘About Abroad’ because you came at this
really from the traveler,point of view.
And, you know,you've done the van life.
I think you've donea couple tours on the van,
on the van life, experienceand how many?
Give us a quick update.
I mean, you've been doing thisfor how many?
(40:54):
How many episodes?
How many seasons?It's amazing.
Oh. Thank you.
Yeah. Well, as a,
you know, I'm a podcast hostthat respects the podcast host
that I'm talking to,so I appreciate that.
it's, a yeah,
I'm in my ninth season
of ‘About Abroad’ now, and I really started it
as a side project, a little bitof like personal context.
(41:16):
I'm from the U.Sand I have lived like,
you know, permanently
in a handful of countriesaround the world and,
most recentlyspent almost the last
better part of the lastseven years living in Spain
and have been traveling around Europe
for the last couple of years,
spending some time,several months
in different countriesaround Europe.
So this is sort of a core partof my personal life.
(41:41):
And, and I started ‘About Abroad’ really
because I was having a tonof side conversations with people
as the explosion of remote workwas happening
and you know, matchedwith my experience navigating
the complexities of beingan expat in different countries,
dealing with visa stuff,bureaucracy, taxes, all the,
(42:01):
the not so fun partsthat don't show up on your
Instagram accounts.
dealing with all those.
There were lots of conversations taking place,
and I thought, you know,when I started this,
there wasn't a whole lot of content out there about how to do it.
I mean, I was really, like,
navigating it in the dark, andit was complex and challenging.
And so I thought, I lovehaving these conversations.
I'm a podcast junkie and we'realready having them off the air.
(42:25):
What if we just record themand share with people,
what these experiences are like, and so
it sort of expandedinto a whole.
The space that we're talking
about is kind of generallyfocused on global mobility.
so it's not just like boringvisa and bureaucracy stuff.
It's also telling people'sstories about
how they managed to move abroad or
or how their, you know, traveling permanently.
(42:47):
and a lot of it touches onremote work, which,
which powers a large percentageof those people's stories.
But it's so it's interesting, as you said,
the extremes are not necessary anymore.
And you, Nick bloom,I think in is TED Talk
puts up a slide
when you used to Google ‘remote work’,
and there's kind of two categories of
pictures and the images that would come up.
(43:07):
when you see it,
one is like the lazy slob hanging out,
not getting dressed in the house,
you know, a stone's throw awayfrom the fridge, and the TV.
And then the other oneis the people
in beautiful tropical locationswith a laptop on their lap,
and a nice fruity drink with an umbrella.
And then, of course,the punchline is the fruity
The umbrella is actually a Wi-Fi antenna.
(43:31):
it's helping theperson get in.
You know, it used to bea pretty extreme thing,
but now, as you said, it'snot necessarily so extreme.
You don't have to be so extreme.
You don't have to do it full time.
And I'm curious, how has thethe paper work in kind of the,
the nasty, ugly stuffthat you do have to take care of
in terms oftaxes and visas.
And, you know, it's
(43:51):
not the sexy stuff on Instagram, but it's the stuff
to get to those, fancy Instagram pictures.
So I wonder if you could sharehow that world has changed.
for people thinking aboutpart time, a little bit,
maybe a year, you know,or maybe it's an extended,
you know, kind of vacationor mid midlife retirement,
you know for, to go spend a yearin Tuscany or whatever.
(44:13):
Yeah.
It’s an awesome question
because this is thethis is today's reality.
That was not the realityfive years ago.
and much less ten years ago,
it used to be
extremely difficultto find a country
that would want to accept you,if you weren't a citizen,
or if you didn't have some sortof, like, real need to move there
(44:34):
like work was bringing you there
marriage wasbringing you there.
you know, a refugee statusor something like that.
The options were very limited
and mostly you were restricted to
you know, 90 day or60 day tourist type visas,
maybe one year, like astudent visa or something.
but these days,
I mean, they're literally
I've talked to the people behind the scenes
(44:54):
who are creating these digital nomad visas.
They look at us like
we at Doist look at users of our products.
I mean, they're trying to build features and attract you
to their countries.
They're literallyfighting over you
to bring you here.
And they've paved a very clearand easy path to get there.
and so, you know, it'sa lot easier than it used to be.
(45:15):
And there's in a lot of cases, it's,
not even a questionas to whether or not you'll
you'll be approved.
It's just a matter ofdo you check 3 or 4 boxes?
you know, do you have a little bit of incometo support yourself or savings?
Do you have a cleanbackground check?
And, do you have a, you know, a doctor
that will say you're not,you know, deathly ill?
And if thoseare the cases, then,
(45:36):
there's a lot of countriesthat will accept you for a year
or up to five yearsand even provide
like a permanent path to citizenship, or permanent residency.
So, yeah, it's changed a lot,
with the emergenceof digital nomad visas.
And on the flip side,
it can never be understatedhow painful the,
the processes are,
because they're always a lotharder than they look.
(45:58):
I'm a big advocateof hiring a professional to,
to help you navigate this space.
It's relativelyinexpensive,
and is super helpful,like
someone that just knows the local ropesand can walk you through it. So,
yeah, we talk about thisa lot on the podcast, honestly.
Like, we have individual episodesfor individual digital nomad visas
or countries that you might be specific in
(46:20):
specifically interested in,
people who in our space
that we've talked to a lot, Jeff,that have have done that and,
you know, are living abroad in
Portugal or Ecuadoror wherever it may be.
And, so we're tryingto tell their stories
and explain how they navigated that space.
Yeah. It's great.
I was listening to the episode with the guy,
talking about getting your Italian,
(46:41):
your Italian citizenshipif you got Italian ancestry.
So I’m gonna
I shared that one with the family.
And what he said
it takes years and years.
So let's get to be friends.
But, you know,we'll get you there eventually.
Well Chase, this has been great.
I want to wrapkind of on the last topic,
your advice for people that just feel like,
you know, the standard pathdoesn't necessarily feel good
or just doesn't fit,
(47:02):
or I think I'm looking for something different.
I love your experienceof your corporate thing.
When I interviewed at a Fortune,
I don't know what they areFortune 50 company
and I went andit was great interview
and we went and we sat down
and the guy got this little floor plan
office plan out with allthe desks and the cubes.
And he's like, yeah, you'regoing to be right here
(47:24):
And I literally I mean, even now
I just, my stomach just turned over.
I'm like, I'm going to be there like?
And all these little squares,you know, like I go there.
And then my first job in tech at Intel, at RNB, the Robert Noyce Building
main headquarters.
Six foot cubes, seas of them.
And then, you know, all the support columns
(47:45):
have labels, either, you know, a letter or a number.
So, Chase, you're at pole G6,the printers at A2.
I'll meet you, over at Brian'sdesk at, you know, H4.
And I just it's just like, Aahh
So for people that feel likethat’s not the way, you know,
I don't want to followthe pattern.
You didn't,
You saw a different path.
(48:07):
You set a different priority.
You made conscious trade offsand thankfully found a partner
who had aligned incentives.
What do you tell people?
That, hey, if it doesn'tfeel like the standard path
is the right path,there is an alternate.
You know there are alternativesand you can make it happen.
Yeah, I think you justsummarized it really well.
You know, I have toldmany people
(48:29):
that I've had that conversation with that in
in my early days of my career.
I decided that was going to be my North Star,
that freedom and flexibility were, you know,
going to be a part of my career.
And I was going to prioritize that over all else.
And so, you know,that means
(48:49):
inherently making some sacrifices
and I kind of have like a little
it sounds a little bitoverly ambitious,
and I don't think I can actuallyhave a huge impact on this,
on this goal, but it's a little bitof a goal of mine to like,
make sure that people don't have to
make those sacrifices and trade offs anymore.
trade offs anymore.
and so, you know,
collectively, I think there's a lot of people working towards that.
(49:12):
But it may mean still that at some point
you have to makesome sort of sacrifice.
It may mean a step back
in your career trajectory,it may mean a slight pay cut.
It may mean taking a job,
working at somethingthat isn't exactly aligned
with what you want to do.
But if you see it asone step back
two steps forward, and look at the long term path,
rather than, you know,
instant gratification,this is what I need right now.
(49:34):
Then I think you're setting yourself up for
for long term success
More ideally, like, I hopethat's not the case for you.
I hope you canjust take the
take the path forwardthat, you know,
check all the boxesthat you want
and move forward
in a into a companythat accepts you
because the truth is, is that there's
it's never been easier than it is right now.
There's more options out therethan there ever have been.
(49:57):
When I found Doist,my wife found
the job that I got hired at Doist forby looking at a Pinterest board
that had 75 jobs, 75 companieshiring from anywhere,
and it was the only thingwe had ever seen like this.
And of those 75,I think 73 were engineering jobs.
And, you know,I'm not an engineer.
(50:17):
So I thought,oh, I'm kind of screwed.
I looked at those two jobs,I applied for the one at Doist
and I ended up getting it.
But I tell that storybecause
that was all we could find on that at that time.
I can probably name you, like 75 dedicated job boards
just for distributed work.
Flexible work right now.
so there's so many optionsavailable to you right now
(50:37):
if you're feelingbeaten down by this,
I just there are positions out there.
It's never been easier.
And then if you're willingto make a little sacrifice
if needed because that's your North Star,
then I think you have,you know,
you have a bright futureahead of you.
That's great.
Well, Chase,I think we'll leave it at that.
That's great advicefor people.
And you are changing the world.
(50:58):
You aresetting the pace.
You know, you'reyou're sharing your stories.
You're out there a lot.
You publish a lot,you talk a lot.
You share great guests, so
I think you're making an impact for sure.
Thanks, Jeff.
I appreciate itlikewise.
appreciate allthat you're doing.
And I love listening to theguests you bring on here.
So hopefully we added a little value today.
And, it was a lot of funfor me, so I appreciate it.
(51:21):
Great.
Well, thanks for coming onI appreciate it.
All right.
He's Chase, I'm Jeffyou're watching Work 20XX
Thanks for watching.
Thanks for listeningon the podcast.
We'll see you next time.
Take care.
Awesome.
Awesome.
That was great, man.
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Monster: BTK
'Monster: BTK', the newest installment in the 'Monster' franchise, reveals the true story of the Wichita, Kansas serial killer who murdered at least 10 people between 1974 and 1991. Known by the moniker, BTK – Bind Torture Kill, his notoriety was bolstered by the taunting letters he sent to police, and the chilling phone calls he made to media outlets. BTK's identity was finally revealed in 2005 to the shock of his family, his community, and the world. He was the serial killer next door. From Tenderfoot TV & iHeartPodcasts, this is 'Monster: BTK'.
Stuff You Should Know
If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.