What's up, everybody?
This is Cortland from IndieHackers.com, and you're listening to the IndieHackers podcast.
More people than ever are building cool stuff online and earning their financial freedom
in the process.
And on this show, we dissect the latest trends, ideas, and strategies these IndieHackers are
using to get ahead, so the rest of us can do the same.
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Today, I sat down to talk to Dan Pearson of Unsettled.
Dan is an expert in what he calls the future of work, which is really a new opportunity
for IndieHackers all over to build better tools and applications and software for companies
who are changing the way they work.
It's pretty obvious with the global pandemic this year that a lot of companies have been
forced to work remotely, they've been forced to work in these hybrid environments.
And so in this episode, we get into not only Dan's story, but also just a frank discussion
about the coolest ideas and opportunities that we see for IndieHackers in this space.
Dan, welcome to the show.
Thanks for having me, Cortland.
Excited to be here.
Yeah, I reached out to you in response to a tweet you made back in October.
You said, "$58,000 in sales so far this week for a product that didn't exist one month
ago.
B2B is wild, not sure why I ever bothered with you lowly consumers."
And you never actually shared what it was that you were building that made so much money
so fast.
So tell us what you're working on.
Yeah, totally.
So I mean, that $60,000 was two big deals, right?
It was $30,000 in sales to a very large technology company in Seattle, and it was helping them
call it like kind of elevated team building, like bringing in industry leaders and people
who have different interesting things to say, it was connection sessions, helping the members
of this organization break down silos and have like intimate connection, and then different
workshops that we ran to help them find that personal and professional growth.
It's very, very much tailored to this organization, like extremely custom.
The second part of that $60,000 was another $30,000 deal, and that was a pilot to help
a Fortune 50 pharmaceutical company figure out how they could roll out this massive amazing
future of work initiative.
And I think like seeing how progressive and forward thinking they were about how they
were moving to this new future of work showed us that like there was a market to help other
companies do the same and like really be first movers in this market of helping companies
transition to a hybrid environment.
Those were the first two deals, like they very much were taking into account the problems
that we heard, but like the solution that we're now working on as a product is an evolution,
I would say of those very like service oriented, we're completely customizing this for your
needs approach.
And that's like, I mean, that's a great way to start a business in my opinion.
Yeah, I love that point.
I've said it on the show a million times, like you don't have to start with something
complex and ambitious, like you don't have to start with a SAS application, even if that's
where you want to get, it's probably easier to start with a service, you know, something
simple, make a bunch of money in your case $60,000 in a week, and then use those learnings
and use that money to sort of fuel you to get to the next step.
I also want to talk about this term you keep mentioning the future of work.
You and I spoke last week and I kept calling it remote work, you're like, no, no, it's
bigger than that.
It's the future of work.
And I think it's important to talk about this because people are always complaining that
they don't have startup ideas, they don't know what to work on.
But every now and then there's like a big societal change.
And if people start living a different way, they start working a different way.
And it's just a good excuse and a good time period to really come up with a brand new
idea and serve some new market that didn't exist before.
So right now, that might be the future of work, we'll see.
And then finally, I want to talk about transparency, because a lot of people are skeptical about
being transparent.
They're skeptical about sharing their revenue numbers, about sharing their strategies, they're
afraid competitors are going to steal their ideas.
And your tweet, I think capitalized on transparency, you talked about how much money you're making,
and people ate it up.
You got like 1600 likes, you got hundreds of retweets and responses.
Why do you think people were so supportive despite the fact that you were only kind of
half transparent?
You didn't really share what you're working on.
Yeah, so Marketing 101, I'll leave a little bit to mystery.
It really it's the genesis of years of being open and transparent on Twitter and through
Medium.
And the first, maybe 2000 people like that tweet in total, but the first 30 that got
it there and that retweeted it and put it in front of Cortland, who now is having me
on his podcast, and I get a chance to share the first 30 people that were there that were
like my kind of small army of folks that have, you know, followed me over the years, they've
all seen like all of the downs that then put me in a place to like, have, you know, some
of these call them ups on the roller coaster were of entrepreneurship, where now I'm starting
to find more success after like, years of struggle.
But those are people who have, you know, seen tweets about mental health, and about me leaving
Lyft, you know, two months before my cliff, and like, I don't know, the hundreds of thousands
of dollars that in stock that I left behind and how I thought about that over the years,
and they've seen, you know, the two financings that were, you know, term sheets signed basically
for the second one very much so like, we work in Santa Monica whiteboarding with, you know,
the two guys who were in the investment firm, and then two weeks later, seeing Coronavirus
start to ramp up and getting an email that told me that, you know, that $500,000 was
had basically vanished.
So there are people who have been along for the ride.
And I think that's so important, because if people only see, you know, the success that
you're in, and you're transparent about your success, and you're kind of just bragging,
and you're kind of just an asshole.
So you have to really, I think there's there's two sides of the coin, and people embrace
the vulnerability and people embrace the transparency when you're sharing things that you know,
it's not just the good times.
Yeah, I was going back to your old tweets.
And you've got one from July of 2019, last year, that I liked and retweeted.
And you start off by saying, I've been walking through the entrepreneurial desert since August
2014, when I got my last paycheck from Lyft, five years of broke struggle, damn, dude.
I mean, I've been so broke, I can't pay attention.
It's been so long of just trying these different businesses that, you know, have their moments
of kind of that most of the people listening to this podcast can probably relate to where,
you know, it seems like you're finally about to hit that, that precipice of like, of success.
And then suddenly, it's further out in the distance.
And like, the entrepreneurial process is never overnight.
Like you always hear that it's one of those kind of truisms that you, you know, you see
people say, like, there's no such thing as an overnight success.
Like that is so damn true.
Yeah, I think that's very true.
There are very few overnight successes.
But I also want to know what you've been doing to be so broke, because you don't have to
be broke to be an eddy hacker.
I know a lot of people who are never broke, they're never super stressed about finances,
they were never wondering when their next mail was going to come from already working
on last year when you tweeted that and also walk us through this five years you spent
in the entrepreneurial desert, as you called it.
Yeah, so the last business I was working on was called Bolt Travel.
So this idea of community travel, like millions of people spend billions of dollars a year
flying all around the world for these group travel experiences with complete strangers,
which I thought was just just kind of crazy.
So we are our innovation there alongside awesome trips, like rooftop tent camping, safaris
in Africa and sailing in places like Greece and Norway and the Caribbean and overlanding
in Baja and hiking in Patagonia, all those trips, like the innovation we were bringing
there was this idea that you could build community around those experiences and extend those
experiences.
I mean, it was going great, man.
When I say we, very much I mean me.
I was 100% by myself, indie hacker style, and I always use the kind of the colloquial
we because I feel like you're talking about a company and it maybe makes people think
that you're a little bit bigger than you really are, but very much it was me.
So that was what I was doing up until March 10th, 2020, when I had to get people back
from Panama and get people back from Patagonia and then face over the course of a month or
two, increasing understanding that my life and that business had changed forever due
to the pandemic.
Yeah, that's an interesting point about saying I versus we, because I think a lot of people
in the indie hacker space are benefited by being very personal and down to earth, especially
if you are in the education business, if you are spending a lot of time directly engaging
with an audience.
People like to buy from a human like to kind of know who you are and what your story is
more than kind of like this nameless faceless organization.
But in your case, it might have been different because you were actually organizing these
like big trips for people and groups and maybe they wanted to think that they were in good
hands and that you're like a professional team of people who had done this before.
What was it like being an indie hacker working by yourself in the travel business?
Yeah, totally.
And it was very much I was flying by the seat of my pants.
I had very little direct experience in creating that kind of travel product at scale.
Like I'd always been the person that like put together those kinds of trips for friends
and family.
Like I'd worked for Lyft managing their travel partnerships, but those were like figuring
out how we could partner with hotels and airlines to get more people, you know, to drive in
cars with pink mustaches.
It wasn't like facilitating travel experiences all around the world.
So I mean, you know, I started at square one, I threw up like a really terrible Squarespace
page for that company for for bolt.
I emailed probably 20 people told them what I was doing and the very first trip that bolts
ran was in Oaxaca and there were including myself five people on it.
The other four people.
One of them was my brother.
One of them was an ex-girlfriend from San Francisco.
One of them was a buddy from San Francisco and then we had one random who was a Bitcoin
millionaire and I was looking for people to hang out with over New Year's good really
good guy.
I should say, but that was that first trip and that was the start of that business.
And from there, you know, I think about marketing any business, but particularly I think for
indie hackers, I think if you picture concentric circles like smaller circles within larger
circles like the first circle or the people that you know the best and who support you
and want to see you succeed and like are going to be your biggest advocates and that's who
you start with.
Right.
And then the circle outside of that is then the people who, you know, maybe you've worked
within the past, haven't talked to in a while, but like could be interested.
And then, you know, you move further and further out until you reach the group of people who
you've never talked to in your life and like then your product better solve a problem pretty
good for them, you know, but until you get there, like you have these people who want
to support you and that's a great place to start.
And what about this was five years wandering through the entrepreneurial desert?
I'll start the story and about pretty much 12 years ago, right out of college, I started
a very successful internet marketing agency by myself down in Argentina, I'd moved down
there to teach English, couldn't find those opportunities, so I started writing freelance
articles and it was very much the heyday of SEO, spam, article writing.
I started hiring, I found some success with that and started hiring other Americans who
had moved down to Argentina in a similar fashion to teach English and couldn't find those opportunities
and like built a really successful agency out of it that I ran by myself as all like,
you know, kind of freelancers, but I was running it and I mean, it was very much like Tim Ferris
for our work week style, like maybe even before he coined that term, it was like 2009, 2010,
right alongside anyway and I made more money working less back then than I ever have even
come close to since I was making, I was netting like 10K a week, which was wild because I
was like 23 years old, flying all around the world, you know, in first class, having these
amazing adventures and so I mean, that was, you know, the start of my career, so like
that was my first taste of entrepreneurship and literally that started with me writing
an article for like $6 about going on a vacation in Cape Cod for like God knows who, that was
the start of that business that turned into this pretty substantial venture until it got
smashed by Google updating Panda and the whole SEO industry changing, yeah, like overnight
just demolished that business.
So give me a sense of the economics of a business like that.
You're hiring a ton of writers, you are writing a ton of content, Google's not that smart
back then.
So you get into the top of the rankings.
And then what you're making a ton of money on ads.
It wasn't even that sophisticated.
I had primarily one client, which is like the most like beastly, broadly internet marketing
company that no one's ever heard of called red ventures.
They're now I think, maybe even public, but they have all these different verticals where
they're selling reselling ADT home security and they've got every like they're completely
vertically integrated.
So they have websites where they're capturing traffic, then they have a call center.
Yeah, I'm looking them up right now and they're huge.
They own CNET.
They own ZD net.
They own TV guide.
They own Metacritic.
They own GameSpot.
This is a huge media company.
Exactly.
So like back then they owned all of these, this web of web properties, like hundreds
and hundreds of domains where they would capture traffic for ADT home security, satellite TV,
a bunch of other kind of consumer products.
So they needed a ton of articles to rank for them.
So like I found them on Upwork or rather they found me on Upwork Upwork didn't even exist.
It was Elance.
This is 2010.
They found me on Elance.
I did like maybe a $1,300 project for them where I wrote like 20 of these complete bullshit
articles myself.
And then they were like pretty dramatically quickly escalated to we need like 500 articles
a week at like 15 bucks a pop.
So I was like, okay, cool.
We can hire Americans living down here who have degrees from like Yale, you know, in
English, but can't find work teaching, you know, people had to speak and write.
So that turned into a big opportunity, but it got smashed overnight.
I mean, literally overnight, it got demolished.
Yeah.
So I can't imagine what it felt like to go from making 10 grand a week, 23 year old to
later in your career, trying to be an entrepreneur, take two, you know, you're trying to get both
travel off the ground and it's a slog, right?
You're taking your sister and your family members on vacations, you know, trying to get
your first clients.
I don't know if you go to taste like, you know, the real hardship of entrepreneurship
after having such kind of an easy success early on in your life.
I think about being a monetary success.
Like I was making all this money and that was admittedly awesome, but I felt like I
was contributing zero value to humanity, perhaps even being like extractive, just putting this
like complete arsenal of complete bullshit out into the universe, right?
And so coinciding with that business getting affected by being so badly affected by that
Panda update, I'd become really interested in collaborative consumption, the sharing
economy.
This was like 2011, 2012, right when it was starting to take off.
So I sent a cold email to a VC that turned into a three month internship in San Francisco
at a sharing economy company that then turned into a role at that VC that then turned into
a Lyft in 2014, 2013, 2014, right?
Kind of as, as Lyft was taking off and yeah, it was definitely, I felt much more fulfilled
in terms of the projects I was working on, having deep important act impact on humanity,
but I still really didn't have the kind of freedom that and the balance between like
living to work and working to live that to me is, is fundamentally important.
Yeah.
I was making 30 minute long walks during the day, hour long walks, two hour long walks,
and then I quit my job at Lyft before about two months before my cliff.
So left, I don't know how many hundreds of thousands of dollars on the table, got on
a bicycle and rode across the United States by myself.
And that was really, you know, my return to entrepreneurship after that first company
that I'd started doing SEO content marketing.
So I spent four years in that grind in the Silicon Valley grind and then decided it wasn't
really for me.
It's hard to go from a life of freedom as an indie hacker to a life of basically a desk
job where you have a boss telling you what to do and you've got to be, you know, addressed
a certain way and got to have your button in a certain chair at a certain time every
day.
It's the freedom is kind of the number one thing for most people who've tasted it before.
It's kind of like the baseline because even though you found purpose at these tech startups,
you said you were talking, you're working for sharing economy companies, you ended up
at Lyft.
The sharing economy is like this very purposeful thing or it's kind of a marketplace based
apps where you're connecting people to people.
So Lyft and Uber, Airbnb, I think is an even better example where it's a little bit more
humanizing and people can sort of help each other.
And even though you have purpose there, if you don't have freedom, it's almost like the
operating system of happiness.
Like you can, once you get that base layer down, you can start to build all sorts of
apps and programs on top of your freedom.
But if you don't have freedom, even if you're making a lot of money at a big company, it
could feel like you got to get out.
You got to do something else.
Exactly.
And I mean, for me, I think I take it over money.
There have been times over the last five years, as you alluded to, when you read that tweet
where I've just been so broke.
But to me, the fundamental freedom to be talking to you on this podcast from the coast of Oaxaca,
Mexico is the most important thing and one that I just absolutely need to optimize for.
Okay.
So you're done with Silicon Valley.
You're done not being free.
You decide you're going to be an indie hacker again.
What do you do?
Sure.
So it's about a year and a half of travel after Lyft completely disassociating from
Silicon Valley.
And that led me to 2016, it was like, okay, like, you know, there's no way that I want
to go work at these businesses again, these like large Silicon Valley startups, I recognize
that like, that wasn't the life for me.
So I started a new business, it was like probably this on paper, like sexiest business that
like 500 people have started and they've all failed because it's a terrible idea.
I can get into that one if you're interested, but yeah, for sure, let's hear it.
So it was helping people understand how they could best use their frequent flyer points
and miles.
This is how that business started.
It's called Slingshot.
I posted a photo of myself in first class on Cathay Pacific Airlines on a flight from
Hong Kong to New York City.
It's the longest flight in the world, or at least was at the time.
Posted a photo and said, you know, do you want help learning how to do this?
Like would this be valuable if I helped you do this?
And it got, you know, 250 likes on Facebook and all these people hitting me up and I was
like, I've got something here.
I've got something here.
And I spent two years trying to make that work and burning through a ton of savings.
And it's a brutal business because the banks and the credit cards and the airlines don't
want to share any data because they have no reason to.
And that whole system is opaque for a reason.
I took learnings away from it for sure.
But I mean, it was to call it a full two years of working on a business that like, I should
have after three months realized wasn't going to be any kind of success.
Okay, so let's fast forward to where you are today.
Your travel businesses don't work out, both doesn't work out.
Obviously, it's pretty hard to have a travel business during a pandemic when traveling
is basically illegal.
But now you're working on a company called unsettled.
And you're doing these crazy deals, you made 60 grand in a week.
Tell us about how you got here.
Yeah, so I mean, rewind to March 2020, that deal fell through, which was going to give
me the security that I lacked forever.
I mean, part of that deal was a 50,000 they were buying $50,000 of my equity in the company
and that was just going straight to me to pay off credit card debt that I accrued building
these businesses.
I mean, I've written like media posts about that, maybe I could, you know, link in the
podcast or something, but that was going to really give me a lot of security that I'd
lacked for so long, you know, and like that tweet that I referenced about being broke
for five years.
So in the process, reframed what I was thinking, realized that like, okay, like travel not
coming back anytime soon, two friends of mine had started a company about five years ago
called unsettled.
And we just started having Frank, you know, honest conversations about like, maybe we'll
be able to get through this and get to the other side.
You know, the likelihood of that will be stronger if like we team up and we go through this
together.
So, you know, that conversation turned into them, aqua hiring, because again, it was just
me full time bolt to be a part of unsettled primary product before the pandemic was 30
day retreats around the world, like Tuscany, Buenos Aires, Bali, Cape Town, they set you
up with an awesome place to live, coworking space, and then a really intentional, thoughtful
set of experiences over the course of 30 days with a premise that like, you need to be a
little bit unsettled to realize true personal and professional growth.
Because if you're not, then like, you know, you're kind of just coming at it from like
a place of stagnation and a comfort zone.
That's not really the moment when you're going to, you know, find that kind of growth for
yourself.
And I mean, unsettled, obviously, their travel product got smashed equally hard in March.
And yeah, we had that frank conversation, they gave me a bunch of their company for joining
enough to like really feel like I'm an owner of it, which was an interesting trend transition,
I think from like being an indie hacker to being now part of a team.
Okay, so both your businesses got crushed by the pandemic.
And you decided to join forces.
But you're pretty much still at square one.
I mean, this is where almost every indie hacker is trying to figure out what they're going
to work on to try to make money.
And that's where you were, because none of your old stuff was going to work in the pandemic.
How do you come up with a new idea from scratch?
Yeah, so unsettled had put out virtual experiences, but it was all business to consumer.
And when I came on, what I really wanted to work on was business to business opportunities.
So figuring out, again, totally online, like what value unsettled approach could bring
to different businesses and different organizations.
And I went through 10 different iterations talking to so many different businesses, big,
small, had been remote forever, and never been remote a day in their life, you know,
different industries, all different kinds of businesses and trying to figure out what
their pain points were, how we could solve them.
And over the last call it three or four months, very much service based, we put out a bunch
of different kind of feelers to friends, alumni, people who've been on unsettled trips, just
to start conversations and really learn what the problems were around this very sudden
dramatic shift from the office to remote and hybrid environments.
Yeah, I think this is a process that a lot of any hackers kind of skip, which is determining
what you actually want to build, right?
You don't want to just like randomly just start building something because you're excited
about it.
I mean, that can work.
Like maybe you'll see even 100 or 200 examples on any hackers of people doing that, but you
don't see like the tens of thousands of people who tried that and build something that nobody
wanted.
But if you actually start with your customers, and you start with their problems, and you're
asking them, you know, what their challenges are, you're looking at where they're spending
money, or maybe even just doing research, like any any hacker could go, you know, type
in news.google.com, and just do some research type in future of work, or remote work, and
you'll get a ton of articles, and you'll see a ton of people talking about their problems
and what they're struggling with.
So I like the fact that you guys actually sat down and did that work.
What did you discover were the kind of the top problems that people had that were worth
solving and building a business around?
That's probably mistake number one that every entrepreneur, including myself, makes is like
trying to solve problems that either don't exist or don't align with people's, you know,
actual kind of like use cases and what they're doing and what they're trying to figure out
such an easy mistake to make.
I mean, I find myself literally still making it every day having now started, you know,
successful businesses and failed businesses.
So yeah, so the feedback that we heard from all these different businesses that we spoke
to was they had made that transition overnight from collaborating, communicating in the office
to now having to figure out how to do it in a remote environment and like both as individual
contributors and then as organizations, just like chickens running around with their heads
cut off.
And I think March, April, May, it was so reactionary that companies fell into bad habits
and negative routines around remote work.
And like, that was really the challenge side of it.
Now I think that we've been working remote for call it seven or eight months now, like
now I think there's an opportunity to transition to the opportunity side of things like, okay,
like let's solve these problems and see how it can manifest as as positive implications
for businesses.
I myself have stopped referring to it as remote work because I think it extends so far beyond
that.
All of the companies, almost all of the companies I should say that that we talked to like they
want to get back to the office in some form or in some shape or maybe it's not even the
office but it's like in real life experiences, you know, in 2021 and beyond as the health
situation improves, maybe, you know, 100 person org is ditching their office and like suddenly
that budget is freed up to fly everybody to Bali for 10 days for, you know, awesome team
retreat kind of thing.
So all that to say, like, most companies, I don't think are going to say we're completely
ditching in real life to go 100% you know, remote quote unquote remote.
I think what's really exciting about the future of work if you keep an open mind to it is
that it's expansive and it's unlimited and it's it's exponentially open for new ideas
to the point where like, we're going to find these hybrid environments and hybrid companies
and hybrid everything that like takes the best parts of of being in person and having
that that like IRL connection and matches it with the flexibility and the opportunity
to work at your best, like whenever you want, however you want, wherever you want.
So that's the kind of company that I want to work at.
I mean, I'd imagine for at least a lot of people that the kind of company that they
would want to work at too, it's like, who doesn't want to, you know, have their cake
and eat it too.
Exactly.
Who doesn't want to eat cake?
So why don't we talk about some ideas?
Let's talk about some of the cool companies we see out there in the future of workspace.
And maybe this will help people get their creative juices flowing for companies that
they can start themselves.
What do you see?
Who's inspiring?
And what are some of the cooler businesses that are catering to this future of work?
So I mean, there are so many different apps out there that are trying to tackle like what
it means for all of us to be working in this completely new environment.
One of my favorites there is called icebreaker.
Like I think of it as what would technology look like for connecting us in a really intimate
like fun, engaging environment if we'd started out with this idea, like rather than, you
know, being in a business context, like we're doing this for social connection.
So they're flying in literally icebreakers into the conversation and sending people into
breakout rooms accordingly, and giving people the prompts they need to like, be human, right?
So it's definitely not what you use for like an important sales call, but like internally
to build culture at your team.
You know, this is it's like a much better tool than something super utilitarian, like
like Zoom.
There's no personality with Zoom.
It's 100% utilitarian, like I must call you and you will pick up and then you call somebody
and they pick up and you have a conversation.
And like that works.
I mean, that's fine.
But I'm on the icebreakers website right now, www.icebreaker.video.
And they got all these little cool events so you can do a happy hour or you can do some
sort of virtual meet and greet.
And if you click into the events, they tell you like, okay, here's the template, you know,
here are the little cards, here's what the prom is going to be, here's how we're going
to match people together.
And it looks like they're free for basically teams of up to 40 people at once.
But once you get past that, you've got to pay $100 per group, which is actually not
that much.
So I can see people adopting this and really getting used to it and creating company traditions
and making it part of their culture.
And then eventually, you're kind of hooked on it.
And you're paying 100 bucks a month to make your team better, really, which seems like
a good deal.
I've seen some of this stuff like early on during COVID.
Like somebody had like a, I think a goat cam, where they would put a goat on camera from
their farm to just sort of join your Zoom calls, just to kind of spice up your meetings
and make it interesting.
But like, this one seems a lot more, I don't know, purposeful.
Yeah, I think it's a great example of human centric design.
And that's something that I think a ton about that is the small team that I'm working with
that we think a ton about.
There's a couple of other ones that I've seen that are pretty cool, that are part of this
idea for having kind of a virtual HQ for your team.
One is called branch.gg.
I signed up for that one, but they haven't let me in yet.
Another is called www.gather.town.
And it's kind of the same idea, rather than kind of just sitting at your desk all day
and looking at Slack.
They have these virtual, like, almost like game like areas where you have a little character
and this top down view, like you're playing Zelda or something.
And you move around this little virtual office that they've created, and you can see all
your coworkers.
And I think the whole idea behind it is that you don't really have to like ping somebody
for a call.
Like you don't have to like schedule a call and figure out when you're going to talk to
them.
You just kind of walk your character up to their character, and you just start talking.
And based on the proximity of like your little guy on the screen, people can hear you if
they're close enough to you.
So I've been using this for the last week with my brother, just trying to test it out.
I haven't got the rest of my team to sort of buy into it.
But it's cool because it brings back a little bit more of the serendipity factor of working
in an office.
So the little map that we're on is like an actual office.
They've got little chairs at desks that your character can sit at when you don't really
want to be disturbed.
Or you can go literally stand by the water cooler and the cafeteria and people can walk
up to you and just start talking.
I totally get that need and it's something we hear from our perspective clients and the
folks that we're working with now, like all day.
It's like, what is that kind of Jane Jacobs style, you know, creative chaos, people bumping
into each other and starting new ideas and starting new projects and eventually even
starting new companies.
Like what does that look like in a world where we're all spending 97% of our time at home?
It's funny.
I'm like kind of at the opposite end of the spectrum.
I'm like, how can I look at the screen less?
How can I be, you know, no video on calls without offending people and like just audio
only?
Like I'm really excited about like, I don't have an invite yet.
Maybe I should, maybe somebody that's listening can hook me up a like clubhouse.
I know I was like blowing up as audio only because I think people like, you know, we've,
we've been on zoom for so long that now people are looking for, I think a lot about cognitive
loads and like how like we have to think so much.
And I think actually zoom and other platforms, even when it's really, really well done, there's
still like that kind of instinct in your brain that tells you like, Oh, this actually isn't
natural.
Like there is a millisecond of a millisecond delay and you know, it just doesn't feel
natural.
So I'm like, I'm big on the, you know, the audio only, but I definitely see the value
of the platforms that you're talking about.
Like branch.
Yeah.
The, uh, audio only thing is really good.
Even branch and gather, like I think they have video built in, but it's not really like
you don't need it.
Like I was talking to my brother and I gathered this morning without, I was on my phone and
I don't think they have support for video on your phone.
But it felt very much like clubhouse where it's kind of like you can just walk around
your house talking to people.
And the problem with the zoom chat is like, even before this podcast, like I had to clean
up my living room to make sure it doesn't look like shit and like make sure I'm like
wearing a shirt and wearing pants and stuff.
And it's just like a little bit too much friction versus these audio only platforms kind of
solve that serendipity problem where people can just kind of walk up and talk to you and
there's no preparation necessary.
You can just kind of talk to your coworkers and just jump right in and out of conversation
without any of that extra friction is honestly just annoying.
Like whenever like you have to schedule a call, you have to go through this time of
like this process of figuring out like what time are you free?
What time am I free?
What's the best time?
Then it turns out that this whole big thing.
And then like maybe you just wanted to ask like a really simple question that could take
like five seconds, but because you scheduled time for like the meeting ends up dragging
on like longer than it really needs to just to make it feel like it's worth it.
Like it was worth setting this whole thing up, but it's just stupid.
It just makes no sense.
It's just obvious like this is eventually going to be better.
Exactly, and I think particularly when you're talking about the act of building consensus
around how people communicate and collaborate within an organization like within a company
like that's the product that we're building.
That's where I spend 95% of my working hours thinking about.
Right.
So you had these these two services that you created that you sold for 30 grand each, but
you're trying to turn these services into actual products here.
So give me an example of one of the products that you're working on.
Sure.
Yeah.
So like fundamentally, it all starts with self-awareness.
And so we're building like we think of as as very simply as like the Meyer Briggs or
the Enneagram for the future of work, right?
So there's this universe of different assessment tools.
I mean, it's massive and companies pay tens of thousands and hundreds of thousands of
dollars for companies to come in and as consultants run these kinds of assessments, but like nobody's
ever built one specific to the needs of this rapidly changing future of work where we're
communicating asynchronously and we're figuring out, you know, in real time, like how people
like to work.
So taking like personality assessment, how people communicate, how people collaborate
and using it to really create a completely new framework for how companies and individuals
think about about the way that they come together.
Yeah, I like that because it's kind of a proven market there.
There's a ton of companies that already pay a lot of money for these sort of employee,
you know, teammate assessments, kind of figure out your personality type, figure out how
you like to work, all sorts of stuff like that.
But given that the world is changing and people are now working more remotely and they're
working from home and they're working like, you know, hybrid.
Some people are remote, some people are in the office, etc.
It's kind of like a gap in the market or kind of a new opportunity to produce an even better
assessment that's sort of tailored for this new way that people are working and companies
probably won't balk at paying for something like that because they already pay for stuff
like that.
But they want to have the latest, the greatest.
They want to have something that's actually accurate with how people are working today.
Exactly.
I think, you know, the next question from there becomes like, okay, you have an individual
assessment for each of the contributors at your organization.
And they understand like, you know, Meyer Briggs, for example, as like introversion
versus extroversion and Enneagram, if folks are, maybe some folks are familiar with that.
It has different types that explain how you like to collaborate.
And like, it's very easy, I think, for those to kind of get siloed and to not be useful
in terms of like how they relate to how you operate like as part of a team or as part
of an organization.
So that's the second element of what we're doing is like taking all of those assessments,
right?
And surfacing the trends that come from them.
So that's like using data from the assessment, aggregating it from all those individuals
to create a report for managers to say like, okay, like these are, you know, for example,
the working hours of the people in your organization and the tools that they use.
But more importantly, like how your people like to communicate, how they like to solve
problems and starting to figure out across a company, like what that looks like.
Ray Dalio is a great example for folks who maybe have seen his TED Talk, but like Bridgewater,
which is literally like the most successful hedge fund in the history of hedge funds.
This is his way of making sure that the best ideas surface and like in real time during
meetings people are evaluating ideas to make sure that, you know, the best ideas win.
So like assessments are just a fundamental, when done right, they're like a fundamental
piece of making sure that business is, you know, that they have the opportunity to be
at their best.
Yeah.
I've seen that TED Talk.
It's pretty cool.
It's called, I think he calls the software, the dot collector.
And so there's people literally sitting in this meeting and like he's like giving an
idea and people in the meeting are like reading, like, is this a good idea?
Like what's my feedback for Ray?
But then instead of just seeing their own individual feedback and what they thought
about Ray, they kind of see an anonymized chart of what everybody else thought of that
person.
So they can say like, Oh, I gave him a three out of 10, but like everybody else gave him
a nine out of 10.
Maybe there's something wrong with me.
Like why did I interpret that so differently, et cetera?
And it's just like, I mean, it looked extremely distracting.
How could you even pay attention to anybody when you're sort of constantly rating what
they're saying?
But I think the idea behind it was kind of cool, which is that like we can come up with
quantitative ways to figure out like how we work together and what everybody's preferences
are, you know, who should we pair up?
You know, somebody might be extroverted, somebody might be introverted, maybe they should work
as a team.
Somebody might like remote work or video calls, somebody might like audio calls.
If there's some way to kind of find that information about somebody before you work with them,
then ideally it'll sort of improve your working environment.
Exactly.
So, you know, across an organization, right, there are going to be points where you want
best practices and you want norms.
And that's what we do next is we create a remote communications charter.
And like I think about Stripe, right, which like you kind of sort of work for right as
like one of the most progressive, healthy cultures and like imagine if every single
company out there was as progressive as Stripe and had the kind of like tools, structures,
resources, common understanding for people to work at their best and to really feel like
they were in the best position to solve any problem that came out there and like, you
know, for every Stripe, right, there's a thousand companies that are just like, we want to see
you from nine to five behind your computer and, you know, and these are the tools that
we use and there's no opportunity to, to like from the grassroots create working environments
that like leverage all of the challenges of remote work to turn them into opportunities.
Right.
That's a super important component of what we're building is that I have like grassroots
bottoms up, like you have a say in the way this company is going to run.
And I think like the companies that me and you and a lot of people who like hopefully
have the agency to like, you know, find the best opportunities, like those are the places
that they want to work.
So yeah, I think it's a big opportunity.
Yeah.
And it's interesting to me how the variance between how good or bad some companies are
at handling remote work.
Like my mom works for a company and they hire recruiters and they're just like super micromanagy
like they have software installed on everybody's computer to watch what you're doing at all
times and that also like measures how long you're there.
And so like, if you're away from your keyboard for 10 or 15 minutes or something, I guess
like sends an alert to your boss or something that you're not working.
You know, and so then like the employees buy these, I think they're called mouse jigglers,
which in some cases are actually physical devices that will just jiggle your mouse to
make it look like you're actually at your computer.
But it's ridiculous.
So I think that's like such a micromanagy, like a very low trust way to manage a remote
team and it's like indicative of a company that just didn't really know how to handle
this transition.
And then there are other companies where like Stripe, for example, like many people are
working remote well before the pandemic, we've got like a wide array of internal tools that
just make it easier to get to know people and to learn about people.
And we use lots of different like slack bots, like there's a slack bot that's pretty popular
called donut that will just sort of regularly schedule meetings for you and kind of random
other people at your company.
And it's a great way to kind of keep in touch and sort of mimic the in person nature of,
you know, just bumping into people at the hallway and a real office where you're not
necessarily going to go out of your way to like, you know, say, Hey, random person, let's
meet, but like with donut, like, you know, you've got this third party telling you to
do it.
So I like the idea that there's just all these different opportunities for people to get
better at working remotely.
And there's a ton of tools that indie hackers can basically build to do this that don't
exist yet.
And it kind of requires an imagination, like you have to kind of imagine a future that's
different, where people work differently than they do today.
But if you can't imagine that, you can just sort of break it down to first principles
and say, you know, like, what should people be doing?
Not what are they doing right now?
But like, what should work look like when people aren't necessarily in the same office
together?
I think there's just a ton of ideas for things you can build that people actually pay money
for.
Totally.
And the most fascinating part to me is that it's never been easier to build those ideas
to like very quickly get a grasp of what the market needs and then turn around with a solution
that like, might not be perfect, but pretty adequately fits the needs and meets the needs
of consumers or of businesses like, you know, the last part of this team journeys product
that we're building for companies that have gone remote is like a slack bot, for example,
right?
So you've taken this assessment, it shows you, you know, the type of remote of remote
worker that you are, how you like to communicate the best way to reach you the best way that
you solve problems.
And we're building a slack bot that will surface those findings for any individual, your company
at the touch of a button, right?
So you can pull up maybe it's, you know, Cortland works in engineering, I'm in marketing, I
need to figure out something about, you know, how our email delivery works.
And like, I can find out exactly how Cortland is at his best in a remote environment so
that, you know, I can reach him in the most effective way possible, just literally just
by pulling up his, his remote style on the slack bot that we're building.
And it's like, that wouldn't have been possible.
Very cool.
You know, you're a computer scientist, right?
By training at least, like, I'm like the opposite of computer scientists, but, you know, with
these no code tools and like, I learned from, you know, maker pad, like Ben Tossle, Tom
Osman, these guys at maker pad that are just creating like incredible resources to teach
people like me, who aren't very technologically product minded to create tools using no code.
But like, you know, that slack bot, right?
It's like flow XO is the tool that we're building that in the database is air table, right?
And Zapier's porting that the individual profile to webflow so that each contributor has their
remote style, right?
On a what seemingly is like a very robust, custom website for each of these clients.
And like, okay, actually, you know, this stuff is very, very buildable within the core over
the course of, you know, two weeks.
And it's a prototype, right?
And like, when we hit it big, God willing, like, you know, we'll have to write custom
JavaScript.
But right now it's like, this gets us there.
And it's doing it, you know, quickly, efficiently, and we don't have to hire developers to do
it.
What do you think about the sizes of different companies that can take advantage of these
tools?
Because when I use some of the kind of video game type ones I was talking about earlier,
where you're kind of walking around this virtual world and talking to people, like, I noticed
that it's like pretty helpful even for a small team, like the little virtual office I have
in Gather is huge, it could easily support like hundreds of people.
But like, just with me and my brother, I found it interesting to be able to serendipitously
just like strike up, like walk over to where he is, and strike up a conversation.
Do you think small indie hacker type companies, you know, five to 10 people are gonna be buying
tools like this?
Do you think it's mostly for bigger companies?
What do you see the opportunity when you're trying to develop these tools that you're
coming up with and sell them to customers?
Sure.
I hope Gather doesn't charge you by the square foot, right?
Or maybe you're just like bawling out and you're gonna get like a corner office, you
know, penthouse with like, with panoramic views of the San Francisco Bay.
I think like, when you work with three or four people, you know them so intimately well
at companies that are run by people who think about how to make their employees happy and
like how to take their feelings and how they work into account like three to four or five
people like probably don't need robust tools like what we're talking about, but like, imagine
you're at 14 people and three of those people were hired during COVID and you've never met
them face to face and like you haven't had the opportunity to understand like how they
work, you know, at their best how they collaborate their personality traits and how that plays
into work, you know, for a 15 person company, right?
I think our sweet spot and we're, you know, we're validating this like in true kind of
indie hackers fashion, we're figuring like we're doing our best to talk to customers
and figure out like who the customer persona is that we want to start with like, you know,
we had all of this success early selling into these massive fortune 50 companies.
And now we're figuring out like, actually, like they have a lot of, it's easy to sell
maybe 30 or even like 50k deals into these companies, but like, if you want to sell two
or $300,000 deals in those companies, like you have to go through incredibly rigorous
like approval processes and there's so many different stakeholders and like, I'll be totally
honest like, I'm very new to sales like enterprise sales and like I'm realizing like I like parts
of it, but the idea of like wrangling, you know, 17 different people from, you know,
from Microsoft into a virtual room and like making sure that all of them feel good about
the solution that you're selling that it's like enterprises and all that to say like
that's a very, very complicated process, hopefully we'll get there.
But I think in the meantime, like when I think about our perfect team size, it's like 25
to 200 people, you know, they haven't done a million of these assessments like they still
have the core issues around collaboration and communication that I mentioned, but like
they don't have these like incredibly arduous processes that you need to jump through to
try new things and they want to be progressive and they want to figure this stuff out, but
they're not exactly like, you know, wedded to what they've done before.
So yeah, I think like a small to medium teams and then hopefully, you know, that'll extend
itself to larger teams once like we're a bit further along with these products that we're
building.
I think most people are willing to try new stuff right now, like as an indie hacker,
when you have some like brand new experimental thing that, you know, you code with like one
person or it's like a no code tool, you can't really go sell that to like an established
company most of the time.
You've got to sell them, sell the kind of stuff to people who are visionary early adopters.
But right now, the entire way that everybody is working is completely changed.
So we're in this like weird phase of humanity where like everybody is an early adopter.
Everybody's willing to try new stuff.
Absolutely.
And the advantage that we have there is, I mean, companies are running around like chickens
with their heads cut off trying to catch up the basic fact that they're no longer working
in their office.
So, you know, whether that's for us at unsettled, or whether that's for anybody listening to
this podcast, that's thinking about a new kind of interest area of like starting to
explore where there might be business opportunities like it's been decades of acceleration over
the course of the last nine months, and that presents so many interesting opportunities
to start businesses whereas like before these companies probably, you know, they would have
been like very, very close to these kinds of new ideas, suddenly they have to find solutions
and you know, that means that there's opportunities to try new things and create new things more
than even more than try new things.
Yeah, even when I was selling podcast ads for indie hackers, I realized that a lot of
companies were just very experimental, like they knew podcasting was this big thing that
was happening, but they didn't really have any proof that it would work for them.
But they were just like, screw it, we've got a marketing budget, like we'll spend
some of it just to try advertising on your podcast, like here's five or 10 K. And it
was shocking to me like how easy some of those sales were, where marketing departments were
just willing to spend.
And then I think for smaller companies, a lot of smaller companies, like they don't
have that kind of budget to experiment.
But what they do want is they want to be big, they want to kind of emulate like what the
more successful companies are doing.
So if I was sitting around trying to brainstorm, like what I would do is talk to some people
at Airbnb, talk to people at Stripe, talk to people like these bigger companies that
others kind of want to be like, and figure out like what tools are they doing?
What kind of internal tools are they making?
How do they handle all these different problems with remote work?
And then like maybe put together like a package of apps or like maybe just one app and be
like, you know, you want to be like Stripe, here you go.
This is how they manage their remote employees, you can do the same thing.
And what small company doesn't want to be like these big companies they admire?
100%, I think companies where they need to solve problems, they want to spend money.
So this is a time to figure out like where that is in the context of this acceleration
of the future of work.
And like, you know, one thing, maybe just an idea that somebody like take this and run
with it.
And hopefully it makes you a million dollars.
You know, like this idea that every company, I think, or 97% of companies aren't going
to be fully remote, they're not going to be fully work from the office, they're going
to be some kind of hybrid beyond that.
That's something that we hear from every partner, you know, that we're talking to now, like
there's going to be some kind of middle ground.
And like, what is scheduling look like, you know, in that middle ground?
Like, what are the tools that tell you what's what is the tool that tells you when somebody
is going to be in the office, and when somebody is going to be out of the office, like, even
if that's just a plugin for, I don't know, Google Calendar or something or a slack bot
or whatever it is, like, that one little tool there is going to be so valuable to so many
people that are could be so valuable to so many people or some variation of that idea,
all that to say, like, if that costs $1 per user per month, then like, you could sell
a million of those.
There are so many fundamental things changing that, you know, it means there's opportunities
to just try new things.
So what is your craziest prediction for like the future of work five, five, 10 years from
now?
You know, maybe it's not 100% guaranteed to happen, but like, what could happen to change
how people are working?
And that would be almost unrecognizable to us today.
The fundamental biggest shift that I am hopeful for as someone who is both spends a lot of
my time working probably too much of my time working right now is the complete disassociation
of time from output.
A friend of mine, his name is Paul Millard, super progressive forward thinker, and he
focuses pretty much exclusively on this idea of the future of work.
And he asked, like, what are the massively radical questions that aren't being asked?
And I think, like, one of the interesting things there is what is the value of the output
that you're creating, right?
Like, maybe three days a week is actually better than five days a week.
Like people talk about four days a week, right?
But like, what if it's putting in a concerted 15 hours per week on the most important tasks
you have ahead of you, and being in a position to leverage those to really, really drive
hard on the things that need to get done.
Another person that I look to for kind of interesting forward thinking ideas is a woman
named Rahaf Farhoush.
She's a digital anthropologist, and she studies how burnout affects creativity, particularly
with the lens of like, we're looking at all this stuff, you know, with this idea that
like how we've measured productivity over since the Industrial Revolution has no bearing
whatsoever on how work should be done today, if you're working in anything that brings
creativity to the forefront, because essentially, like the most important things that you're
doing have now been disinterred from time, you could have a breakthrough in 10 minutes
that's much, much, much more valuable than the 100 hours you put into things that don't
matter at all.
So I think like, that idea that time is now our most like valuable resource, it's like
how can we make the most of it and how can we create the most value in that amount of
time.
And also tools catch up to that, right?
Like I use grain, for example, grain is like a perfect example, or val is another one of
these tools where it takes your zoom recordings, uses I guess AI, somehow machine learning
to create transcriptions that are like pretty good, you know, they're not as good as if
you hired somebody for 100 bucks an hour, but like, they're pretty damn good.
And then you can make a clip from those videos to share with colleagues or whatever you need
to do.
And like, I used to take copious notes during meetings, and after meetings and have to like,
you know, refine them and all these things.
And now that saves like four or five hours easily for my work.
So you know, I can focus on the things that are most important to me.
And that's just like one tiny example.
But as we introduce more and more of those tools, and also just more human centric design
and thought to how we work, then you know, it'll just completely free up so much time.
And like, you know, Chris heard from first base, like, you see him on Twitter, first
base is that they call like the operating system for remote work, they set your company
up with all of the different technological tools that an employee would need, right?
Like you get a laptop, and you get a desk and whatever else else your company wants
to set up.
And then when you're done working for that company, first base takes it back right and
facilitates that whole process of procurement and everything like,
Yeah, it's smart.
They're shipping like desks and computer chairs and like monitors to your employees
so they can set up pretty good home office, which is amazing.
Because now everybody's working remote, like they need this stuff.
Yeah, I mean, talk about an incredible business for the time.
He's been working on that, I think for like two or three years now, like, has just, you
know, I'd imagine hit the absolute jackpot right now.
But like the one thing, you know, I mentioned him because one, because I think it's a great
business, but two, like, he just hammers home this idea that, you know, we're spending an
hour and a half each way on a commute.
And like, when people have that time back, I think that's going to be an incredibly valuable
that they'll be able to spend on the things that they love doing.
So like, top line, the work you do should not be associated with time.
And like, I don't think it should be a five day work week.
I mean, I don't think it even should be a four day work week.
Like I want to work to live rather than the other way around.
And I hope I'm working like two and a half days per week in five years or 10 years.
Yeah, I mean, ideally, you do the work that you need to do.
And who cares how long that takes?
There's nobody standing over your shoulder trying to make sure you work, you know, 40
or 50 hour work weeks.
There's no like sort of untrusting relationship between you and your employer where they're,
you know, making you happen to install a mouse jiggler just to sort of fake like you're at
your computer.
No, it's just like you who controls everything.
And I think, you know, my vision for the future is that there are a lot more indie hackers,
because I think being an indie hacker is all about having that freedom.
It's all about understanding that as long as you can get directly to the end customer
and do something for them, then you control everything about your life.
And if you want to work longer hours and make more money, you can do that.
And if you want to work fewer hours, and you know, make a little bit less money and, you
know, do what you want, like you can do that as well.
And there is no like weird contractual agreement between you and your customers about how long
you're going to work for them.
Totally.
And I'm informed here by literally the wealthiest man in the world telling me that time is the
most important resource.
So like, I very haphazardly and kind of serendipitously got to ask Bill Gates via Twitter, this was
back in 2013, like all the massive resources at your disposal, where do you feel least
able to affect change?
His answer, right?
Like, so this is literally the man at the time with the most money before Jeff Bezos probably
surpassed him.
I said, no matter how much money you have, you can't buy time, only 24 hours in each
every person's day.
So I set clear priorities, like my family, my work pretty hardcore about sticking to
them.
So, you know, I literally I have that lesson I keep like every six months or so I remember,
you know, that like literally the person with the most money in the world told me that and
I'm like, how can I adjust my life to be more in true with this idea that like time is the
one thing that we can't make more of and like, you know, to me is the headline of this future
of work.
And like if it involves artificial intelligence, hopefully it also involves like, you know,
universal basic income, and where people have, you know, the opportunity to like work on
the things that they really, really care about because as you know, the human race, like
those are the things that people should be working on, like the things that are most
important to them and where they feel like they can add the most value.
Love it.
One of the most things here is that for probably the first time in history, like just as an
individual or as a very small team of people, I mean, you're using like no code tools to
build a lot of the stuff that you're talking about and you're doing it like in a matter
of days or weeks, like you can attach yourself to one of these giant movements in human history,
like the future of work, the fact that people are feeling more empowered from their jobs,
that they're working fewer hours or working more on their own terms, they're working more
enjoyable environments, and you can actually start a mission driven company, a company
where like you're actually changing the world in ways that you want to see it changed and
you can feel proud about what you're doing, you're not just doing something that's opportunistic
to make money and it can also simultaneously make you a lot of money, give you your own
financial independence and allow you to live the life you want to live.
I think it's just a cool opportunity and I hope more indie hackers build in the space
and do things that are real meaningful for other people so they can be proud of it and
they can help themselves and help others.
I'm totally on board.
I just think like, you know, as someone who's listened to indie hackers for a long time
and does not have that technical background, this is an opportunity for anybody to come
to with an idea and just literally start from square one and be able to get somewhere so
fast that you'll have the validation you need to whatever you want to do.
Get more customers, raise outside capital, just kind of keep pushing on the things that
you found out.
Dan Pearson, thanks a ton for coming on the show.
Can you let us know where they can go to learn more about what you're up to at Unsettled
and anything else you've got going on?
Totally so, www.beunsettled.co is where you can find us if you're working at a company
and you find that you're having these issues around communication and collaboration, like
you feel like you don't know how to approach people to solve problems in a virtual setting,
like we'd love to chat with you about that.
Personally, at Dan Pearson on Twitter, Instagram, all that fun stuff, trying to always write
more on Medium as well.
That's at Dan Pearson too and yeah, look forward to hearing from some of the folks who enjoyed
the podcast.
All right, thanks again, Dan.
Thank you.
Listeners, if you enjoyed this episode and you want an easy way to support the podcast,
you should leave a review for us on iTunes or Apple Podcasts.
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there.
Thank you so much for listening and as always, I will see you next time.