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Get inspired! Real stories, advice, and revenue numbers from the founders of profitable businesses ⚡ by @csallen and @channingallen at @stripe Get inspired! Real stories, advice, and revenue numbers from the founders of profitable businesses ⚡ by @csallen and @channingallen at @stripe

Transcribed podcasts: 277
Time transcribed: 11d 5h 6m 45s

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What's up, everyone?
This is Cortland from ndhackers.com, where I find the founders behind profitable internet
businesses and I try to get a sense of how they got started and what's going on behind
the scenes so that the rest of us can learn and build our own successful businesses.
Today I'm talking to Jesse Patel.
He's the founder of a really cool productivity app, one of my favorites, called Workflowy.
I just logged into Workflowy today and it said that my account is 365 weeks old, which
means that I joined in November of 2010, right after they launched.
So it's not often I get to say that I was one of the first users of a product and even
less often that I get to talk to one of the founders for that product.
So I'm super excited to be talking to you, Jesse.
Thanks for joining.
Yeah, totally happy to be here.
So there isn't much written online that I could find about the origin of Workflowy,
just a few articles here and there.
But from what I could find, it seems like it's intertwined with you teaching yourself
how to code.
So maybe a good place to start is how did you teach yourself to code and why was that
something you even wanted to do?
So I think, I mean, I taught myself to code, I kind of been teaching myself to code for
a long time.
Like, I took some computer science classes, just like one and a half at Stanford when
I was there.
And it was like, probably the thing I enjoyed the most, but I just was, you know, it was
like the first time I'd done it, whereas everyone had been doing it since they were 12.
And so I was like, okay, I'm not going to do this.
From my first exposure, like I liked the process of running into confusing things and having
to fix them.
Like some people don't like that.
For me, it was like, okay, this is just a fun puzzle.
And I really love to build things like I was trained as a product designer, and building
stuff is super fun.
And then so coding lets you just build stuff like yourself that other people can use in
a really, really rewarding way, you know, so that
that was kind of my motivation in general.
So I've been kind of like fiddling with it for years.
And then at some point, I had stuff I really wanted to build.
And I was like, okay, I'm just going to start building this.
And actually, that was workflow, it was like my teaching myself to code project.
Because I was like, okay, this is everyone thinks they can make a better like note taking
and task app.
So I'll just waste that idea on learning the code because it's, you know, obviously it's
not actually a good idea.
So and you know, everyone thinks they can do it better.
But why would I be any different?
So I'll just like, use this delusion to like learn how to program.
Do you want me to talk a little bit about like the motivation for the product itself
or just the coding?
I think it would be good to hear about the motivation for the product itself.
Because like you said, everyone wants to build a to do app, everybody has their own unique
styles of working and none of the existing tools match perfectly with what people want.
And so there's tons of tools out there.
So what was motivating you?
What did you not like about existing tools?
And what did you want workflow to do better?
So basically, I had this in like, 2000, it was a long time ago, 2008, I think, I was
like knee deep in this job that was really complicated.
And I was basically the person in part charge of business development for a nonprofit tech
company that was trying to do decentralized video, it was like a, it's kind of like an
activist project, and they were trying to figure out like, how do we make money?
Is there a way for us to make money in a business sense, as opposed to like raising money from
donors, which is what they had been doing, we had like 4 million active users.
And so there was an audience, and we were trying to figure out what are the different
ways you can monetize.
And there were like 30 different legitimate things to explore, like avenues, each of which
would, you know, like have a department at a real company or whatever.
So everything from like selling independent, it was a video thing.
So selling independent films, to advertising, to customizing and selling the software itself
to all other people who distributed video, just like there were many different avenues
to explore.
And each of them was really complicated.
And I was just kind of cycling through project management to do note taking apps, trying
to keep track of all the complexity, and getting really overwhelmed.
And so I kind of was like going over everything, everything, everything, and the thing I started
using like word outline mode.
And I was like, this is kind of the best, but I just, I need it to be able to zoom in
I was like, I need to be able to, in Basecamp or in any of these other tools, like, they
have a set structure.
And there's always comes a point where you have a to do that's like, you know, like make
marketing proposal, and then like, okay, well, I want to like write out the ideas for that
marketing proposal, but I can't do it inside this to do like it's, it's in this to do it
needs to be there.
So basically, I just had this sense like I needed something fractal, and, and like that
went in forever.
And then like having used the outline mode, I was like, Oh, outlines are useful.
So this idea of like combining the what I knew is like this need for a fractal thing
with like an outline thing, and the first version of workflow I built actually didn't
look like an outline at all, it was like, like more of a standard task list type thing
that had, it kind of looked like the Mac Finder with columns mode, I saw a screenshot of that
online.
Yeah, it was just like columns.
And you click on like each row of a column, and it opens up another column to the right.
So you can kind of zoom in.
But it was just different.
It was different.
And it was pretty cool.
And like, actually, um, do you know the company news cred?
No, I don't.
So it's like a big company in New York, they're like a media company.
They have hundreds of employees.
My friend Shafka started it right when I was first working on workflow, and he, he used
that version of workflow with like the columns to kind of like start news cred, which is
hilarious.
That's cool.
Yeah.
He's the only person who like he used that he was I'm using number one, he's number two,
and he's the only person who used that version of workflow ever.
So he must have liked it if he started his company with it, or was he just doing that
as a favor to you?
No, no, he was using it legitimately himself.
And he didn't, it didn't have collaboration at that point, so he was using it as like
a private and a project management task management tool.
Yeah, he liked it a lot.
That must have been pretty inspiring to have somebody who was really using your tool.
How seriously were you working on workflow at the time?
Yeah, so I basically it was like November of October of 2009, I quit my job because
that job was kind of impossible.
I like I love the people and I'm still super good friends with all of them.
But it was just this job where I felt like I was failing because it was like, okay, none
of these business models are basically working out, you know, like none of them seem like
their rival.
Anyways, I quit my job and I was like, okay, I'm gonna go full on for with workflow II.
And so it was kind of like, like four months or so of just like solid working on the product.
And I had I kind of had a prototype that had been using before I quit that job.
And I quit the job thinking like, I'll work on workflow II, but really, I just wanted
to start something.
Just kind of segues into Mike and like recruiting my co founder and stuff.
Do you want me to go into that or should I?
Sure.
I mean, today you're working on workflow with Mike.
But how long were you working on it before Mike came into the picture?
So I mean, so basically, since I started playing with it in 2000, before I even moved to Geneva,
I started like, I'm gonna learn to code so I can build this thing from like action.
So probably it was 2008 that I started working on it, like a little bit, you know, I mean,
it's really slow when you're like learning to code to make something.
So it's 2008.
And then in 2009, like early 2009, I started doing a lot of work on it.
It was in like June of 2009, and I started like really working on it.
It was in Berlin at the time, like working out of the SoundCloud offices.
How did you end up meeting Mike and deciding to work together?
Beginning of 2010, basically.
So it was like, like nine months after I really started working on it.
I had something I really liked.
I had a couple people who were using it and I really liked it.
And I was like, starting to go insane.
I remember reading, I think it was like, Naval had just launched a venture hacks or something.
He hadn't just launched it.
I had just discovered it rather.
Yeah, I had just discovered venture hacks, it was like end of 2009.
And I was reading out voraciously all these articles and Hacker News and all this stuff.
It was like the dawn of the era of entrepreneurs writing honest things on the internet about
starting businesses.
And like both venture hacks and just Paul Graham's stuff was like, find a co-founder.
You're crazy if you don't find someone to work with, right?
Plus I was having the sense of like, oh, I'm like a very beginning programmer here.
I'm running in circles a lot, I have no idea what I'm doing.
So I was just like, okay, you really need someone who's actually a good programmer to
work with me.
And I'm just going to go insane working on my own.
So I just emailed two friends in probably December of 2009.
And I was like, hey, I want to start something, do you want to start something with me?
And one of them, one of them was like, oh, I just started something with another friend.
And these are two friends who I knew were technical and who were not working, had just
left their jobs.
And the other one was Mike and he was like, yeah, this is a good time.
I was just starting to think about like, what's next?
So Mike, I knew from college, we've lived in the same dorm.
And we'd kind of been friends for a number of years since, so we met probably in 2002.
But we weren't like super close friends, we were just like friendly and we had in the
same friend group so we'd see each other out and see each other at other people's houses
and we'd chat and catch up and like, oh, what's been going on for the last few months or whatever?
And then he just said, yeah, it sounds good.
So we got on the phone and I talked to him at Workflow and he's like, not interested.
Let's work on something else.
So we like started working on other brainstorming, other ideas.
And we settled on a general area that was very different than Workflow, which was basically
helping like self-help gurus promote like build ways for other people to follow their
advice like through an app.
So basically, if you write a book saying like, here's how you start your business or here's
how you get six pack in 100 days, we basically have like the actions that you're recommending
people doing and a way for them to track whether they're doing it and a way for you to engage
with the community of followers and all this like encapsulating people's advice in an app.
So if you published a book, the idea was it would come with an app and a website that
would help people actually do what you're suggesting they do.
Interesting.
That was the idea we were going to work on and we're starting to work on it.
And then I was like, we're going to apply for YC.
And Mike was like, he wasn't super psyched about that idea.
And I just kind of he wasn't against it, but he was just like, whatever.
So I just applied for YC.
I also decided at the time I was living in Geneva, Switzerland, because my wife, my now
wife girlfriend at the time was living there.
And I decided I was I needed if I was going to start something, I needed to move back
to San Francisco and be near Mike if we were going to work together.
And then once we got into YC, it was like, oh, actually, I think I already had moved
back at that point.
So so yeah, I guess YC didn't fit into the picture.
I just knew I had to be back and I wasn't super happy in Geneva.
Why weren't you guys working on workflow?
Why wasn't Mike excited about the idea?
Because it seemed like it's something that you'd pour a lot of time into and had some
preliminary users.
I mean, I actually only had a couple of users.
It wasn't like I had a lot of validation at the time.
And I think Mike's reasons were pretty like the same reason that I thought it was like
a throwaway project kind of like in or I was rationalizing to myself that I didn't think
it was a big deal is because everyone thinks that they have like the next big idea for
how people organize themselves and how you keep track of your information and stuff.
Right.
So it's like, I don't know.
And then he's also just he's like a guy who uses simple tools where he's like, I'm happy
with the text editor.
I'm not like trying to find the next new weird thing, but I think that's basically why he
just like he tried it.
He was like, I'm not that excited about this.
Yeah.
And in the area also was an area that he found very uninteresting, honestly, like the rationale
like makes sense to me for why he didn't want to work on it.
So that's so I didn't exactly fight it.
At the same time, I kept working on it.
And I eventually, you know, like, kind of, it is what we ended up working on.
So I had conviction around it.
Yeah, I mean, it sounds like it's a tool that you were making for yourself more than anybody
else, at least.
Yeah, you wanted to keep working on it, which is kind of cool, because it gives you a lot
of insight as to how good the tool is, you know, you're eating your own dog food, which
is some of the most common startup advice out there.
But anyway, I'm really interested in hearing about your experience with the Y Combinator.
Were you at all nervous about getting in?
Yeah, I was nervous.
But I think I was pretty confident we'd get in.
And how was the experience of actually going through YC for you guys?
What'd you think about it at the time?
So I have like, two somewhat, they're not contradictory, but like different angles on
what it was like doing YC.
One was that it was like really unpleasant, because they basically hold your feet to the
fire.
And they're like, you have to accomplish something, right?
And then Paul Graham is just really frank, and he's not in charge anymore.
But he's he was just like, I think this is terrible, like, he was just like, I thought
you guys are great at the beginning of this, of YC, and now I think you're idiots for working
on this.
And he'd be like, I've seen a million online collaborative whiteboards, you know, and like,
this is not going to go anywhere.
And like, what makes you think you can do this better, there's no like special moment
for this or whatever.
Yeah, Paul Graham can be pretty frank.
And it's really helpful at times.
And it's also like really soul crushing at times.
I remember he told my co founder and I that one of the ideas we pivoted to was the worst
idea ever, and that they always reject companies who apply with that idea.
So that was rough.
But anyway, what were some of the good parts of YC for you?
I think I don't think we're clearly would exist without Y Combinator.
And here's the very, that's one part, it wouldn't exist and no one would know about it without
Y Combinator.
So the reason it wouldn't exist is because Mike and I were like, enter Y Combinator
with this idea.
And we're halfway through about I think, like almost immediately, we realized that the original
idea wasn't, we didn't want to work on it, because it was too dependent on these on the
basically the publishers and the self help gurus, who were the people who were gonna
basically like be, you know, writing the advice and publishing something like in building
like an app with our thing.
But you know, we did a talk with Tim Ferriss, and we talked to a couple of other people
who just did, who were the kind of people who would want to target and realize that
they just wouldn't weren't going to care, they were going to be those kind of semi
invested people who you'd have to be fighting to get their attention.
And then all your promotion would depend on them and, and all your content would depend
on them.
And you just would have no ability to independently, you know, you basically wouldn't be in control
of your own destiny is what it felt like.
And I you know, it's kind of a two sided marketplace where like, one party, not us was in charge
of both sides, we're like, okay, this doesn't feel like a good idea.
And then we were floundering around, just experimenting with different things.
We played with making a bunch of Facebook apps, and we played with a couple of ideas.
But as soon as we decided that wasn't a good idea, I think I started kind of lobbying
Mike to start working on workflow, because a couple people in YC had started working
on workflow, we started using workflow, and they really liked it.
And they're like, Oh, here's what needs to change about it.
Here's what's good.
And here's what's annoying.
And I was like, Oh, this is further validation.
And we have nothing to work on right now.
And the other thing was Mike had started using it.
He was kind of like, Oh, I see how this is cool and how this is different.
And at this point, I had already rewritten it to look like a piece of paper and to work
like an outliner as opposed to the columns thing.
And so basically, we switched halfway through YC and actually didn't even tell, there's
this thing at the time called Angel Day, I think like Angel demo day, I don't think it
happens anymore.
But we actually didn't tell anyone we were working on workflow in YC until we gave the
presentation at Angel, like the Angel Day, where we're like presenting workflow.
And like everyone in YC was like, we've never heard of that before until you just presented
it to everyone.
And we were like, you're like, yeah, sorry, sorry about that.
Yeah.
Were they excited?
Or were they upset?
No, they weren't upset.
It was just kind of, I think funny.
I think they thought it was funny.
No one was, no one was, no one was upset.
They were like, Oh, at least you're working on something you've been kind of doing like,
do you like cats or dogs better apps on Facebook for a couple of weeks now, seems like nothing
can be worse than that.
I think one of the cool things about workflow is it's like super innovative and super compelling
because you invented something that was completely new.
I mean, there were other outliner tools, but none of them really looked like workflowy
or worked like workflowy.
And I think having that extra step of having to teach people how to use a product kills
a lot of companies, but it kind of worked out for you.
I mean, it took Mike a while, but he eventually came around and decided that, Hey, this is
pretty cool.
And people in your batch also realized that it was pretty cool.
And I even remember reading like a review from years and years ago about workflowy where
somebody called it basically the best note taping, note taking an organizational program
that they had ever come across, which is pretty high praise.
And I felt similarly when I first used it too.
So I'm just curious, like what makes workflowy so good and maybe could you describe it for
people who've never used it?
Yeah, totally.
Before I do that, I forgot the second part of the question for the YC thing is that we
wouldn't like, we're not people who promote things and I'm not a marketer.
So I would like to be, but like, but if workflowy had never gone through YC, we would have had
three users, right?
Right.
And they would have kept using the product and they would have eventually maybe steps.
But like once we launched what YC just gets you on block on TechCrunch and life hacker
basically.
And then like on day one, we had like 10,000 people using it and they didn't stop using
it.
And we're like, Oh, maybe, maybe this is real, you know, like otherwise before we had a couple
hundred people using it, but it didn't feel like it wasn't obvious to us that was an opportunity.
But then once we had a much larger number of people using it, which we would have never
gotten, I never would have even emailed TechCrunch, you know, I would have just been that's a
character flaw of mine, you know, so that was huge.
It's like that alone, like made an enormous difference.
Anyways, pitching workflowy is probably my greatest weakness.
But workflowy, so workflowy is an application people use to organize all the information
in their life and their work and it becomes kind of their hub.
It's open on average for 11 hours a day, which means people just have it open.
It's like Gmail, people have been using it on average, like our average active users
been using it for like almost three years, like two years, so which is a testament both
to, you know, how useful it is to people, but also to like, you know, if we were growing
super fast, that would not be true.
What it actually is, it's basically like infinitely recursive bulleted list, so bulleted lists
where you can just dive down into any section and focus on that.
And it basically means you can have a huge pile of information that is manageable at
the human scale where you can slice it to see one part of it.
You can also do tagging and searching so that you can just slice down your huge pile of
information that hopefully has everything, you know, from all aspects of your life and
then just see the one part that you need to see and have it be kind of just easy to mess
around with.
I think what's really special about it is that it lets you create, that's one part
of it is that it lets you focus, but the other thing is that it lets you create structure
in a really low friction way.
So when you're using workflow, you just kind of by default create some structure.
And you don't really have to think about it because it's bullet points.
But at the same time, like all other apps do for you, like all the apps that are special
CRMs or whatever, they're basically letting you create a structure, they define a structure
for you.
Right?
Like, oh, you're like leads go in here and then when they're moved to this thing, we
move them into this other, you click a button and you move it into this other list.
Basically like most software is like lists and like moving stuff around lists and responding
to when things move into different lists and different categories in some, in some sense.
And what we do is basically let people like define software for themselves that like works
exactly how they want, that has the structure that's perfect for them and for their unique,
you know, situation.
So I think that's kind of what is really special about the product and, and also what partially
what makes it hard to really grok is that people have to say like, oh, I have to figure
out the right structure for myself.
And like, in addition to entering content, I have to be thinking about structure and
thinking about how do I organize this, but you don't have to and that's also structure
just kind of happens as well.
So that's, that's cool.
I think the first time I used workflow II got it instantly after I created a few bullet
points and zoomed into one.
And then it kind of, you know, took over the entire document and that bullet point was
now at the top level.
So I was like, Oh, okay, so this is like an infinitely deep outline where I can put literally
all of my information in this one document and it'll never be too much because you can
always zoom in and zoom out, which is really cool because then you can organize things
and reorganize them really easily unlike in Google Drive or something where if you mess
up your folder hierarchy, like you're never going to go back and fix it because it's too
much work.
But if everything's in one document, you can easily copy and paste it.
So it's super cool and I understand why it really resonated with some people and fit
into their working style in the way that other tools never did.
So let's go back to your story at YC.
You might, might not remember this because I barely remember it myself to be honest,
but I think we actually met briefly way back in 2011 at the YC headquarters because you
did, I think you were summer 2010, right?
I was winter 2011 with another app called taskforce and I think you and your co-founder
Mike may have come to my classes demo day.
Do you remember coming to that or am I just making that up?
Yeah.
Yeah.
I remember, I would, I came to the demo days back in the day for sure.
Yeah.
I remember talking to you guys and I think one of the cooler things about workflow is
that you guys never raised money after YC and today it's like now it's increasingly common
to just start a startup without raising, but back then everybody wanted to raise money
and I remember meeting you guys at YC because you guys were some of like the few people
who just didn't seem to care about it and I also met Kevin Hale from Wufoo who came
to give a talk at one of our YC dinners and I was blown away by the things that he talked
about and how successful they were and how they also didn't care about doing the things
like the conventional way and also the base camp guys kind of stood out back then.
So I'm curious what was driving you and Mike to go in alone and be independent and not
really care about raising from investors?
So I think there were a couple things.
One was that I don't, investors like, we did talk to something, we spent a couple weeks
talking to investors after YC just because it's what everyone did and no one was interested,
you know, because what we were doing was weird and hard to explain and it hadn't launched
so we didn't yet have like lots of users.
I think if we had started raising like a day after we actually launched, we would have
had success.
But so we kind of did try, is the answer like in the beginning just because we're like okay
I guess we should do this, like everyone's doing it.
We didn't really want to but we just felt pressure to and then kind of the further along
we got, we were just like I don't like authority and I don't like the idea of having bosses
who aren't me, you know?
So like that's kind of why I didn't want to raise money and also it's all the stuff that
people say about it, you know, like reduces your outcomes, the scope of your outcomes
a lot.
So like, you know, if you raise money at a whatever valuation, it means you're like the
minimum at which if you sell it at that exact valuation, like it's a failure.
So if you sell for 10 million, if you raise it 10 million, you sell it 10 million, it's
like a huge failure.
And yeah, so basically like that's one of the big reasons, like basically not having
a boss and like minimizing the range of your possible outcomes.
So the downside about not raising money is that you have to make money on your own, right?
You're still living in San Francisco or the Bay Area, you're still paying probably ridiculously
high rent.
What does your financial situation look like at the time and how are you guys surviving
and what are you charging for workflow?
So this is one of our big areas of, one of the biggest issues between Mike and I in the
early years was, so he was like post Google and he made tons of money at Google and he
had all this stock.
And I was post working at a nonprofit and basically I spent all my money paying rent.
And then my wife, my girlfriend at the time, basically just like was paying rent for us.
But we had enough users and they kept telling us they wanted to pay us.
So like after a couple of years, people started paying and it was pretty early on.
Like we had, we had significant revenue, like pretty quickly people were willing to pay
us.
So it was enough to pay rent and stuff.
So basically we just got really lucky in that we never did marketing and people would just
write about the product because they loved it and we got a couple of really big people
writing about it.
And then we'd get, we'd have a lot more users and then people use it for 11 hours a day.
So other people see it over their shoulders and then they they're like, what's that?
That's weird.
That's cool.
I'm gonna try it.
And then so basically we've, we've just been very lucky in that the businesses supported
our pretty laissez-faire and lazy approach.
It's like entirely product.
It's just entirely product oriented.
Yeah.
That's really cool to hear about.
I'm curious about the early days of living with really like no funding and kind of just
having your girlfriend pay for things and, and trying to charge, like what was that process
like of first putting a price tag on work flowy and how many people signed up to pay
initially?
Yeah.
Um, well, I mean, let me look at our graph, but basically you guys started charging after
you launched, right?
So like this influx of 10,000, we started charging like two, two years after we launched.
I think it was like, okay, so much much later, it was like mid 20, this is like after I'd
spent all my money, I was like, Mike, we need to start charging.
And it was like wasn't on his radar and I was like, please, he's like, okay, fine.
But anyways, so it was just like what we did was we were just kind of wimpy people.
And so what we did was like, we're going to grandfather everyone who's we're going to
set up usage quota, which is 500 bullets a month, you can add for free.
And then we're going to email everyone who would was above that in the last few months
and say like, Hey, we're going to launch a pro thing.
You can have it for free, but please pay us anyways, you know, like, and in the first
day, like, like almost 30% of the people we sent that email to signed up for pro.
So we were basically immediately making like a decent amount of money.
And it was just clear that people like wanted to pay us, they like wanted to support us,
they wanted the product to get better and to survive.
So it was stressful and like, for me, it was I mean, honestly, for Mike, I don't think
it was stressful, like not having making money from the product.
For me, it was stressful because I'd spent all my money.
So like, but then like, once that happened, I think it was clear that there was this is
a real thing.
Why did you guys go for two years without charging?
I'm like, what was your game plan?
Do you feel like you're going to get millions of users?
Honestly, it was it was just like, whenever I brought up the conversation, it was just
not, it didn't feel like it was a priority for well, first, I mean, first of all, there
was a period where we didn't have enough users that it would have made a huge, it would have
been like a lot of money.
So basically, once we got to the point where, where it's like, oh, now we have like a lot
of users, and we probably if we think about how much we could make, it probably would
be meaningful.
Then it became the question of like, for Mike, it wasn't a priority.
He was just thinking like, well, let's all that matters is getting a lot of users, and
they're willing to pay us will make money.
And then for me, it was a priority because I didn't have any money.
So it was just like a matter of talking about it together enough that he understood where
I was coming from.
Like, oh, I had this conversation, he's like, I didn't realize you spent all your money.
Like I had no idea, you know, so like that having those conversations, which is actually
I don't know if you want me to throw in advice, but like, one of the biggest things I would
suggest people do, if you're starting a new thing with with any other humans, is have
like a weekly structured conversation where you bring up any issues that that haven't
been resolved.
Because issues that fester like something small can become something big and like an
accumulation of lots of small things becomes like a terrible relationship.
So basically have a weekly conversation where you're like, is there anything that's bothering
you?
Is there anything that hasn't been addressed and just like deal with it?
And if it turns into a big fight, like get some third party to to help you figure it
out.
Whether it's some some person you will trust or like a paid coach or whatever it is, because
like that's how we didn't end up charging people.
That's how I ended up spending all my money with it because he didn't even realize that
I was spending on them.
You know what I mean?
Like, like,
there just wasn't any communication.
I mean, there was communication.
It's just like, it was kind of like, if you're really focused on building this thing together,
then every once in a while you kind of like slip in something that's really bothering
you.
Like you try to slip it in and it's not even heard because everyone's distracted and everyone,
you know, like super communicated constantly about the product and about lots of things.
But there's like this one thing and I'm like, you know, I'm a little ashamed about it because
you know, like, oh, I didn't have that much money to begin with and like, so yeah, I would
just say like, I my sense is that like relationship issues are one of the biggest things and that
biggest issues with companies.
And I mean, I know that from talking to tons and tons of people.
It's just that like co-founder relationships are really difficult.
And I would just say, like marriages, like the ones that work are the ones where you
address the issues with small issues before they become big issues.
So like have a process where every week you're just like, is anything wrong?
Let's deal with it.
Yeah, I'm dating like a relationship therapist and she's taught me so much and like about
exactly what you're saying, that's crazy to hear.
And I know that you and Mike, I listened to Mike's mixed energy interview from a couple
years back and he talked about some of the challenges that you guys had as co-founders
and how you guys ended up going to a relationship therapist, like a couple's therapist, not
even like a business guy, which is like, I think a really smart idea because the problems
are the same.
I mean, you have this thing, you have this relationship that's just as close, you know,
are almost as close as like the relationship between a married couple or parents or something
where you've got this startup that you're working on and it's your baby, you know, it's
the thing that matters to you most in life, except unlike everything else in your life,
this other person has a say in what goes on.
So, you know, I totally agree with you that people don't talk enough about co-founder
relationship issues because every startup that I've ever started with somebody else,
there have been blow up screaming fights, you know, at least at least one.
And now I'm working with my brother where we've been doing that since we were kids.
So it's like no big deal.
It's super easy to recover.
But anyway, on the Mixergy interview, we got to kind of hear Mike's side of things or he
talked about the differences between you and how you are kind of like really focused on
moving fast and you didn't really, you're a little bit more risky and he was like a
lot more risk averse.
I think it'd be interesting to hear kind of your side of that, of that conflict as well.
Like what separates the two of you and what was hard for you about working with Mike and
how did you guys resolve things?
Yeah.
So I mean, so a lot of the things that were difficult are similar things that are difficult
with my wife, to be honest.
So it's like funny for me to see like, oh, it's not just them, you know, like, like one
is, is both that I like to, that I am impulsive, like I would say I'm impulsive and Mike is
the opposite of impulsive, right?
So like Mike is extremely deliberate and like, and I'm probably not deliberate enough.
Like Mike is too deliberate, I'm not deliberate enough.
So I just want to like think of things and do them and try them.
And Mike wants to think about them probably longer than he needs to, which we've both
talked about this.
Like we both agree that that's overall probably true for both of us.
So that's part of it.
And so that's like a bigger picture strategy thing.
But I think almost as big a part of it is just like working styles.
So I always just wanted to talk about what I was thinking about.
And then Mike, and this is, this is the issue that I have with the same issue that I have
with my wife is that, which I'm sure she'll really appreciate me talking about.
Which is that I just, I have an idea and I just want to talk it through.
Whereas being a deliberate person, you think like, Oh, this person is talking about something.
That means they want to do it.
Or it means I have to really think hard about this.
Whereas I'm just going to talk about like 30 things a day, half of which I don't even
think are good ideas.
I just want to like think it through, you know, just throwing stuff out there.
So for Mike, he, he had this, he, he like, so he's like an intense programmer.
He wants to kind of be, here's what we're doing and I'm going to do it.
And I'm going to like focus on it super intensely.
And also he's working on technical, hard technical problems.
So he needs to kind of have his being in the zone and not be interrupted.
And there's this dude interrupting him every half an hour to talk about some stupid idea.
So that's, I think that was honestly a huge part of it where I'd be like, Hey, should
we this?
Should we that?
Hey, what do you think about this?
What do you think about that?
And him just being like, okay, like thinking, thinking, thinking, thinking, thinking, person
talking to me again.
Like, what the, like, let me work, you know, stop, stop interrupting exactly.
So I think that was a big part of it.
And then there was, there's also just like working styles.
Like I really wanted to work together in a sense of like, like I love pair programming
is a good example.
I love looking at the same screen as people and doing things together.
And he doesn't, he just likes to be in his own world and think really hard about things.
And he makes, he's brilliant and he makes great decisions, but he, and so it's like,
I can't fault him for that, but he doesn't like to be working in real time together,
basically.
Yeah.
He likes to like talk about things ahead of time and then go apart and like do the things
you talked about individually.
So it's just like working style things, both being interrupted all the time and that difference
around how you want it to work day to day.
And it just led to us feeling, I think both of us feeling very kind of neglected and,
and leading to conflict because like when, cause just cause like, you know, our needs
weren't being met.
And so I would kind of bring up stuff over and over again in this, in the way I would
be just kind of like pushing at him a little bit, you know, because I just like wanted
that interaction.
Like I'm extremely extroverted person.
I just wanted the interaction and then he would be frustrated because I would be taking
him out of his flow slash giving him ideas that he's not even sure if he has to really
think about or not.
You know, does that mean, does that make sense?
Yeah.
Yeah.
It makes perfect sense.
I mean, you're describing anyone who has like any sort of close relationship with somebody
has some ways in which they're different and they're going to rub up against each other
and they're not going to be able to talk about or they might, you know, neglect to talk about
exactly how they're feeling underneath.
And it's so easy to misinterpret what the other person's doing.
And sometimes just listening to how the other person feels without getting defensive or
fighting back is going to help to make them feel a whole lot better.
Yeah.
And it's super hard to do that, especially when you're implicated in like making them
feel bad.
It's just really hard to hear like, oh, I've done something that makes someone else feel
bad.
Yeah.
So yeah.
So that so that's and then I think basically like, so those are the dynamics.
And then the fact that we never really dealt with them was the problem.
You know, I think all those dynamics were fine.
And then they just built up to this point where we went on this walk.
I remember the walk like really vividly.
We were working out of my friend's company and we walked to Delores Park and we sat on
this bench and I just remember Mike saying like, I don't think I can do this anymore.
Like us being just kind of both of us being miserable.
And I was not thinking about like stopping.
But Mike was just like, look, dude, this is like really unpleasant.
Like we're just fighting.
Like every time we talk, we're fighting basically.
And I was like, oh yeah, this is really broken.
So we need to.
And then we went to therapy and it was helpful.
We stopped therapy way too early because I was feeling very petty pinching, you know,
and it's you know, it's not cheap.
We should have just never stopped going to therapy to be honest.
Well, do you think the tools that you learn in therapy have been helpful up until today?
Because you were mentioning earlier about how to check in with each other and have conversations
on a weekly basis.
Yeah, it helped.
It helped a lot.
Yes.
We went back as well.
Yeah.
Well, I don't want to spend the entire episode talking about co-founder issues, but I think
it's really good to bring it up because like you said earlier, there's a tremendous amount
of advice out there that says you need to find a co-founder and that you'll be more
likely to succeed with a co-founder.
But it's important to look at the other side of the equation as well, which is that a tremendous
percentage of companies fail because of co-founder issues and co-founders not getting along.
So it's kind of a double edged sword.
And I know personally, I've been in the situation a couple of times where business I might have
otherwise done well failed because of my relationship with co-founders.
So one of the cooler things that I think you brought up earlier as well is kind of the
metrics behind workflowy.
How long people use the app for like 11 hours a day and how long they stay, like an average
of three years.
Things like that right out of the gate.
I mean like right when you guys launched on TechCrunch and Lifehacker early on, did you
guys have a really high retention rate or did it take a lot of work to get to the point
where people love the product and were loyal to it?
So we've improved the number a lot, but basically for a long time it's in a business where like
a small percentage of people actually get it.
But then those who do get it basically never stop using it.
So yes, it's been like that from the beginning and that basic dynamic is what, like the number
has gone up as we've improved the product.
The numbers have all gotten better.
But the basic dynamic has been there and that's why we thought, that's why we were like, oh
this is a real opportunity because on day one we had 10,000 people using it and then
like they were telling other people about it and as people kind of dropped off we were
replacing them with new people just through word of mouth and it grew, it was just growing
on its own.
So yeah, it's been a really high retention product from the beginning.
That's pretty inspiring to hear because like I've built a couple productivity tools in
the past too and retention is so hard with productivity because you're essentially building
a tool to help people do work, do things that are effortful.
If you're browsing Facebook it's fun, you're kind of addicted to it but if you're putting
tasks into Asana or you're making an outline in Workflowy about things that you have to
get done or other forms of work, then that's stuff that people might just fail to do all
on their own even if you built a great product because they lack the motivation and it's
effortful.
It's always going to be harder to sell health food than like tasty, delicious, fast food.
So it's pretty impressive that you guys have such a high retention rate and that you've
been able to grow your user base like you have.
What are your stats look like today?
I know you guys aren't perfectly transparent about everything but just ballpark, how much
revenue are you guys generating and how many people are using Workflowy?
We are at about $800K in run rate right now.
We have over 100,000 active users which just kind of goes up but just goes up slowly.
Who all is working on Workflowy?
I suggest you and Mike?
Yes.
So basically that's the area that's in the biggest flux right now.
So about a year ago, for a while, I mean many Workflowy users noticed this, for a while
not much was happening except for us like maintaining things and like doing infrastructure
stuff as the user base group.
But about a year ago, I had twins like three and a half years ago and I was like, okay,
I'm going to take it easy for a while and hang out with my kids and just do what's
needed.
But about a year ago, I was like, okay, I feel like Workflowy is this huge, both something
that I really love and want to have a vision for and want to make it realize that vision
and also just a huge opportunity that is mostly unrealized because it has relatively small
– it's like reaching just a drop of the potential people it could reach.
Because everything is so much smaller than I think it really could be.
So about a year ago, I kind of had that realization and started talking to Mike about it.
And then so basically over this current year, I have basically been like re – like we
just started building a team and hiring people and doing stuff.
So now I have three – it's me and I have two other full-time employees who aren't
Mike and several contractors who are doing a lot of work and we're just kind of – it's
like we're ramping up and like starting an actual – starting a startup.
That's cool.
It's pretty exciting.
I think you guys are in such an interesting position because like 800K annual revenue
is a ton.
The vast majority of people I talk to aren't making anything like that with such a small
number of employees.
So you've got that going for you.
You've got the freedom to work on basically whatever features you guys want to whenever
you want to and obviously from wherever you want to.
And you've got a lot of die-hard fans.
I mean you're not Tom Cruise but people like Workflowy and you guys have a following.
So I'm curious, what is driving you?
What do you want Workflowy to be?
It sounds like you really want to grow but what underlies that and why do you want Workflowy
to be big?
Yeah.
So I mean it's kind of not like that I want it to be big.
It's kind of that – I think it's like the craps person's motivation which is A, there's
this thing I've made which I love but it feels like it's – in a lot of ways that
like 30% of what it could be.
I just want it to be what it could be.
And then there's this whole other angle which is there's this thing – so like that's
a huge part of it.
So I just want this thing to be what it can be and to realize its potential.
And I know there's all these people who love it and for whom it like changes their lives
and I want that group to be a lot bigger.
I know there's just a lot of people for whom it could be like a very important part
of their lives and it's just – it's not right now not just because they haven't
been exposed to it.
I know for a fact there's like a ton of people it's super common that someone tries
Workflowy three times has no idea and then someone shows them how to use it or they have
some insight and they like become a die hard fan.
So I just know that we are – I just have like overwhelming anecdotal evidence that the
opportunity is so much bigger than what we've realized that it's – that's quite motivating.
What are some of the things you want to work on and how do you plan to get bigger and better?
There's a lot of angles.
My main – being very product oriented like I would love to have – to continue to have
a product that kind of grows itself.
My sense is that the product is holding us back in a lot of ways but also the fact that
we've like never done any marketing or outreach or anything is also silly and that we need
to have to do that.
But my personal motivation like the area I'm focused on is how do we make the product stickier
for new users so that they have like a higher percentage of the average new person who comes
to Workflowy.
So we have like 20,000 new sign-ups a month from only from word of mouth and then – but
only – so think about – but then like only like a few like maybe a thousand of those
people actually become real users like long-term users who use it for many, many months.
So whatever.
So that's like 5%.
What is – what do you consider a good percent of – for retention?
So for long-term retention, I'm not sure but I just know that like you know products
that do really well do a lot better and I know that most people who sign up are not
most people but like half the people who sign up don't even like create a single bullet
on the first day.
So I just know that we're like failing in a pretty profound way.
So basically there is this – that's part of it is just making like making the current
product like more obvious how to use it and then there's just like lots of obvious things
that need to be done, lots of features people have asked me for years like mobile being
better and mobile having all the features of desktop, mobile being actually designed
for mobile is like a huge thing.
Improving how collaboration works so that you can actually have a team that really stays
synced by keeping all their information at Workflowy is a huge – that's like probably
the biggest strategic thing.
There's basically like make the product better.
So like dates and reminders, mobile, all that stuff, all the stuff that everyone wants and
all our – I mean all our users want and they've been telling us they want for ages.
Just like getting product momentum and making the product better is a huge part of what
I want to work on and what I think will make it stickier as well as having new user experiences
that are customized for all the different ways people use Workflowy and letting our
users kind of create those experiences for other people.
And then yeah, the collaboration and kind of thing is just massive like that's the
biggest strategically important thing.
It depends on the product being great and – but making the product so that when I
open Workflowy if you have wanted my attention on something, it will draw my attention to
that.
If you have something nested like 30 levels down and you're saying I want Jesse's feedback
on that, you should be able to tag me and then the product will show it to me.
And likewise, if I want to just keep track on like some project they care about that
everyone's managing in Workflowy, I should be able to just like open the app and see
it or get notifications or whatever.
So it sounds like you guys have a ton of work cut out for you and it's pretty exciting
to listen to you list all these features because like whenever I'm working on something,
I have this gigantic to-do list and I've talked about this before that never gets smaller.
No matter how many things I cross off that list and that amount of time I've added more
things that I want to do and I'm sure the same is true with you.
How do you prioritize?
How do you know what goes to the top of the list and how do you sort of figure out which
of your team members are going to work on which things?
Basically there's a couple parts of it.
One is reactive.
So what do people – this is a prioritization, not about who's going to work on what.
But part of it is just like okay, we get a lot of feedback from people.
We have a lot of really passionate users, they tell us what they care about.
So like mobile being better is really obvious.
One of the things that is wonderful about working on a consumer product that is actually
useful is that you end up having a lot of friends who use it so you get a lot of anecdotal
feedback and you can see whether that matches up with the feedback you're getting through
official channels.
But basically we get a lot of feedback and it's like okay, this is obviously the stuff
people care about and the stuff people want.
That's one side.
But then there's also like the vision part of things which is like I have a vision for
Workflowy and I have an aesthetic and I have all these things I want because I want them
and because that's how I've always imagined it.
Like I want Workflowy to be this shared – like a lot of people, probably a lot of our users
like don't care about collaboration and Workflowy.
They probably – a lot of them do like I know that for a fact.
But I'm sure a lot of them like this is my private tool.
I don't want to share it with anyone.
But for me like the fact is like I've always imagined it being the way you can like have
your brain and also share parts of your brain with other people.
And so part of it is just you know like vision and like inspiration.
It's like being an artist kind of like oh here's this thing.
Here's how I want it to work.
So those kind of like mesh in terms of prioritization.
So like if there are things where they overlap or I'm like oh I've always wanted this.
I just think it's cool or whatever it is and people are asking for it then it's – that's
very – you know in some sense it's like confirmation bias where I'm like listening
to the feedback that people want – that I want to hear from people.
But like it's almost like – it's like those two things like play against each other
because I care a lot about what people think and what our users want.
So one of my big things like if I was to give advice to someone, a new person is watch people
– like literally watch people use your product.
Like either physically or via video chat like just watch people use it and it's hugely
– you just get so many insights from doing that and it gives you like a human – a human
– a very human view on your product and all the ways in which either it sucks or is
great and both of those.
I just talked to David Darmonin, CEO of Hotchar.
I don't know if you've seen that product but it literally takes a little recording
as people use your product.
So you can say okay I want to watch 2000 people use my sign in and use it and it'll take
a bunch of recordings and you can watch it.
And it's not quite as good as sitting down with somebody in real life where you can kind
of ask them about what they did afterwards or they can talk you through what's going
on but it's the same – the same phenomenon.
Those products are great.
Like that kind of product are wonderful and I would definitely recommend people use them.
So I think another thing that we haven't talked very much about is kind of like marketing
and because Workflowy has grown so far it sounds like almost entirely through word of
mouth which is amazing.
One of the things that I tell a lot of people who are just starting out is that they should
consider picking a niche and that way they can build something really valuable for a
specific group of people and that group is more likely to fall in love with the product
because it's built just for them and whereas the competitors tools are built more generally.
But for Workflowy, I feel like your product completely flies in the face of that principle.
It's not built for teachers or programmers or salespeople.
It's kind of just like a general product for everyone.
So I'm curious like who are these hardcore Workflowy users?
Is there a pattern that you've discerned among them or are you guys trying to discern
that or is it right now just they could be anybody?
I think it's a very interesting question and I think to some degree we have built a
niche product except it's not niche for any for like a segment for a specific purpose.
It's niche for people who like to work in a specific way and people who are smart enough
to figure out how to use a general tool are not smart enough but you know.
So I think that it's very smart to market to specific use cases like the way Workflowy
is used by like everyone from like piano teachers to CEOs of public companies.
So it is a genuine you know and people like I'm not surprised when someone says hey my
mom just recommended Workflowy to me like that happens a lot.
I think it does skew techie a little bit but it's still a very broad product that does
appeal to a very wide array of people who would be kind of hard to if you saw them together
in a room you'd be like what conference is this you know.
I'm very confused but I think that are like one of the biggest areas that I want to focus
on in the future is making it so that you can essentially if you are a piano teacher
or you are a CEO of a big company who needs to manage all of their one on ones or you
are a customer like a client facing a business that has clients and needs to move them through
a pipeline that you can come to Workflowy and come to essentially a structure and something
that feels like an app that is customized for you because I do think that both for marketing
and for onboarding it is super important to show people how to use the product for their
own purposes and in a way that fits into their own life.
I went to a conference last year a big journal the biggest like investigative journalism
conference I gave a presentation about along with some other people on tools and then I
had a breakout session or like 20 people came and the idea was like how to create your hyper
personalized organizational system in Workflowy and of those 20 people all journalists one
person kind of looked at Workflowy and like checked out the site and tried the demo and
had like their eyes go wide and say oh wow I get this I see how I can use this for everything
I can see how I can use this for this part of my work and this part of our and this part
of my and everyone else really needed to be shown how to use it for journalism and really
needed to be needed specific had they all had the same needs and they all really needed
to be shown and right now we don't do that and I think because of that we are missing
out in a massive way.
So like like I was talking to one guy who's an investor who is like I use Workflowy as
an example like this is very non-self-promotional here as an example of like one of the biggest
failures that I know of where they've just left so much on the table because they haven't
done it like they have this product which has this kernel of something amazing but they
haven't like done anything with it and they haven't promoted it and they haven't built
it out to its potential and you know I you know I tell that because I agree with it and
that's why I'm doing all this stuff now and that's why I'm building the team I'm just
saying like I think that that advice is good advice that you give people you know like
I don't know like for me I'm just like my entrepreneurial story is like doing lots of
things that I think are bad ideas and it working out you know well you use the product a lot
because you built something that works very well for you and ultimately if that doesn't
generalize to some well-defined niche or industry like salespeople that's okay because there's
lots of other people out there who think like you do apparently 5% of people and you can
figure out how to make an appeal to other people and other specific niches later on
and I totally like listening to you talk about the challenges that are happening I feel super
excited for Workflowy because it's there's so much low-hanging fruit it's not like you
guys have spent 10 years trying every single thing and nothing's worked but you guys have
lived on very little in some areas like marketing and still things are looking very promising
I mean what we what we have done is put a lot of like we care a lot about the details
of the product of the I mean about the interactions to be honest of one part of the product which
is the part where you're interacting with lists like you know like lots of the product
like the settings dialogues and stuff is is pretty terrible but that is the thing that
we've spent all the time on essentially so like what is the core value that we are creating
like that's where we've put all of our our energy so the things that workflow he does
it does really really well so I think you know other people besides me have recognized
that workflow is onto something and you guys have a lot of competition and I think it's
one of the more interesting stories because I've never seen a product get cloned so many
times and so directly as workflow and a lot of the clones are crappy like usually when
someone clones a product there's a couple really good clones so basically my thought
on the do you want to finish that I'll let you finish your question now go ahead is so
like the thought on the quote clones is basically like we we didn't do much for a long time
and that is why clones exist because there's a lot of stuff that the product needs and
I think some of the clones are nice but none of them get the details I think as right as
we do most of them are focused on adding more features and the biggest thing that I see
with the clones is that they don't have like I would say is like okay they're not me like
they don't have the vision that I have like I see them I'm like oh here's one that did
a nice job that's interesting and then I kind of look into it I'm like oh like okay once
this starts once we start having product momentum like we're going in a different direction
like we're building on they're kind of adding the obvious adjacent things that are needed
which we will do but they're not building into the future where like workflow is a tool
that actually makes you smarter and is it a tool that helps you think through things
in ways you don't know how to think through and all these things that just kind of come
out of who I am kind of I think like they're just not they're like a lot of them are non
obvious so there I think there's a lot of obvious stuff that could be added to work
play which is good and I glad that people are are doing it but they're also when I look
at them there's two things when I'm like okay that's not as polished as it needs to be and
it doesn't work quite as well as it needs to and just the direction of this product
is not is not as inspiring like I don't see this product breaking out and being used by
you know hundreds of millions of people right they don't they lack the division that underlies
all the decisions that you're making yeah that that's that's how I feel about them and
honestly it's both like really frustrating and really you know like imitation flattery
etc so it's flattering but it's it's frustrating and it is gratifying to me that we've been
able to move into a mode of growth and investing in the product and investing in the company
because you know otherwise the product would just eventually like languish and you know
the the clones the work what was the sequel the Star Wars like number two rise of the
black the clones you know the clones would win well you can't let the clones win and
I think I think it's it's cool to hear your take on it I wonder like the clones inspire
you in a way to the kind of light a fire under your ass or do you just ignore them for the
most part you know I think they inspire like the new team members who join like they inspires
them but I'm like I think they they they upset me but to be honest they don't motivate me
because I have like an extremely strong motivation without clones like if we had zero clones
I would have the same level of motivation I have now I'm just like I am just like dying
to make this thing that's in my head real in the world and and just dying to realize
what feels like this very tangible opportunity in front of me well I think you're in a good
position to do it and you know it's an interesting situation because when you do something that's
new and you're the first mover you have the advantage that you get all the initial mind
share like workflow is way bigger than all of these clones and probably will be for a
very long time if not forever but at the same time when you're the first mover like other
people are going to clone you it just happens you know there's no one is innovative in anything
that other people haven't tried to clone the last thing before I let you get out of here
is I'm curious what your long-term goals are and I don't just mean with like workflowy
in terms of making the product that it can be but I mean like personally like if workflowy
tomorrow was the tool that you wanted it to be and it was bringing people from all over
and they you know you're doing a great job educating them how to use the product and
showing them examples and it was just fulfilling all that we have like a billion people using
it and it's like on every desk and and it's running every company etc so some yeah so
like my long-term goal is to be a mad scientist like very very simple so I want to solve like
all the world's problems you know like like this is like just like completely impossible
and completely crazy right like I I just want to be making stuff that makes the world better
and also just making stuff that I enjoy making so like the dream if everything was crazy
successful would basically be to build more stuff and to focus on some pretty crazy ideas
as well around making people happier structuring society in a better way like it would be awesome
by the time I died if I felt like I was part like not necessarily started a movement but
just was part of a movement or part of something that felt like okay this is addressing like
the flaws of how our society works right now and is gonna hopefully you know a hundred
years from now like people and animals and everything will be happier because of this
thing we're all doing and I feel like that's what honestly like that's what like most people
want like most people would love to feel part of something like that as well right but for
me it's like okay I would like to be in a position to be like a real mad scientist doing
like large-scale crazy things testing back those kinds of ideas and and yeah well I really
hope you get there and I would love to test out some of your mad scientist creations when
you do thanks a ton for coming on the podcast you let people know where they can go to find
out more about what you're up to at Workflowy and about you personally yeah so there's not
a lot of information about me personally on the internet I'm afraid of the internet some
degree to be honest it's probably smart and but Workflowy is Workflowy.com and blog.Workflowy.com
is our blog and Google Workflowy it's what everyone else does our search terms are only
Workflowy slick low-hanging fruit man all right well thanks a ton it was great talking
to you Jesse all right yeah if you enjoyed listening to this conversation and you want
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