All right.
No countdown or anything.
Yeah.
So Last week we, our accountant sent us some business expenses.
They had an email that had like a few listed and said like, Hey, what are these?
Like, can you help us categorize these?
mine were all related to like some meetings that we'd been hosting, but I noticed one of yours was the, the Light Phone.
Is that what it's called?
Yeah.
Yes.
The light, the Light Phone III Well, I, this is my, I've, you know, I sort of realized like, yeah.
my expenses, maybe the topic for conversation.
yeah.
Yeah.
I've been used to for a few years having my,
personal business, you know, being in business for myself, having my business expenses be unobserved by any outsider except my accountant.
so it's a Light Phone III.
I don't know what the Light Phone I was actually, but I.
when it came out.
It has sort of a Kindle -esque type of screen.
Yeah, but I think that's also the Light Phone II Maybe the Light Phone I and II were kind of similar.
Anyway, I'm not quite sure, but I have either a Light Phone I or a Light Phone II And honestly, I, it would be hard for me to justify impossible for me to justify based on my
experience with the Light Phone whichever one I have, buying another one because it's, I never really used it and it bricked.
now it's just like, it doesn't even turn on.
Yeah.
But.
I find the idea really compelling.
the idea with the Light Phone is it's this black and white screen and it's a really simplified smartphone.
So the Light Phone I was just a cell phone, the idea with Light Phone III is what has maps.
has music.
It has, you know, a flashlight.
has kind of the core set of stuff that if you think of the iPhone being introduced in
You know, minus the browser, like some of the iPod in your pocket.
it's kind of like the good, non -distracting, non -infinity pool type of stuff that you would want to have on a smartphone.
Totally.
So it's kind of an attempt and I've found recently that the, are, you know, there's, there's a constant battle to keep the distraction free iPhone, which as you know, that's
this, this thing that you and I have both been doing for, years.
it's the idea that you take any infinite attention, potentially sucking thing off of the phone.
And normally on my iPhone, I, I
don't have Safari, I don't have any social media stuff.
I don't have anything that's potentially got infinite information.
And it helps keep me kind of sane and, and, and focused a bit more on whatever the thing is in the moment that I'm doing.
But lately, for example, the, the ability to turn off Safari in the phone broke.
So it's I could, there are probably ways I could figure out how to,
block it with a third party app, but I just, don't have good self control.
like, will, you know, I Yeah.
Yeah.
And you can't imagine it's like super high on their priority list to fix.
PM is like responsible for that feature is like, man, nobody shuts off Safari.
Who would do that?
so far.
Yeah.
It's annoying though.
I actually is annoying because it's parental controls, right?
It's supposed to be part of like screen time and parental controls.
Like really?
Like that doesn't work.
That was your big thing a couple years ago, So the white phone is in this big category of gadgets where I buy them because I think almost like you're making an investment in a
startup, like an early stage startup.
think most of these I'm not going to ever use, but
Every now and again, there's going to be one and it's going to have this.
It's going to be a hit and it's, and it's going to open up something new for me.
So that's the light phone.
the wave of new video conferencing cameras that came out.
There was the Opal, which I still use sometimes.
The Opal, there was another one called Loomy, I don't know if you know what we're talking about.
There were a couple of years when there were a bunch of those coming out.
I bought all those.
More recently, there's been all the...
AI native devices like the rabbit and the limitless pin and I've like bought all those.
have not opened the box of any of those that I have received yet.
Not sure what to do with that information, but I totally know what you mean.
Like when these new things come out, it's like you want to bet on them and there's a chance that like one of them will be useful.
yeah, it's kind of fun to like be a seed investor in
those new products.
Yeah.
And the funny thing is I think there actually is, depending on the kind of work that you do, like I think the kind of work that we do, there actually is a payoff sometimes.
it could be a payoff and an insight into like, the way, the way these folks did their UI here or whatever, the way this product is positioned, the way it's differentiated in the
market, that that lends an insight that we in turn share with one of the companies we invest in as kind of a lightning demo.
also possible.
not differentiated, right?
Maybe that there's something that is initially appealing to us.
There's a hook where we're like, that's cool.
But then it doesn't deliver on that.
It doesn't follow through on the pitch that it made to us as customers.
Yeah.
And there are these cases and I'd say like an example for me would be the Remarkable tablet, which is this kind of E -ink screen, just a thing for writing on.
And that one has turned out to be really useful for me.
I've gotten a ton of this sort of disproportionate value and it occupies this space for me that like the iPod.
doesn't solve it on my laptop doesn't solve it.
My phone doesn't solve it.
And so there's always the hope that that's going to be one of those.
so we'll see as with any of them, my hopes for the Light Phone III as an individual thing are not high, but it is one of those, one of those basket of bets.
Yeah.
All right, should we kick this thing off?
Let's kick it off.
Okay, this is the very first episode of Jake and J Z.
It's our new podcast.
And what are we gonna talk about on this podcast, Jake?
Well, we're going to talk about startups.
We're going to talk about design, probably, products in general, things that are interesting to us, what's going on in our lives and in the world.
And, those are some of the things.
What else did I forget?
Yeah.
Well, we are among other things that co -founders and general partners at character, which is a seed fund.
So we'll also talk a lot about what we're seeing kind of on the ground, working with startups at very early stages as they design new products and bring those to market.
but, mostly we, we want to have fun.
We want this to be sort of an entertaining, different flavor of podcast, a podcast that you can put on and kind of feel like.
We're just having a conversation.
We're hanging out with you and we hope you find it interesting.
If not, we'll have a good time.
It's always good to to you.
So what do we have on the list for today?
All right.
So, well, the first thing I wanted to talk about was something that we did last week.
We, for the very first time, did an in -person kickoff of Character Labs, which is a program that we run with pre -seed founders a couple of times a year.
Jake, do you want to kind of explain what Character Labs is?
maybe we could chat about just some of the reflections on how it went doing it in person for the first time,
Yeah, yeah, it was wild to be in person.
But yeah, before we get into that, Character Labs is basically, so we started Character a few years ago and this gave us the opportunity to invest in a super early stage company,
we realized like, you know what we could, put together a program where we got a few companies at once, it would make sense for us to spend
however much time we thought was the right amount of time with them.
And because they're just getting started, it would also make sense for us to put together like whatever we think is like the perfect start.
Like if you were beginning a big, big project, you're beginning actually your startup from square one, what would be the perfect sequence of things for you to sort of figure out in
those, in those first weeks?
And so, man, that was awesome because it feels like forever when we were.
Like we go on way back to working at Google, working on products when we were working as partners at Google ventures, when we were working with startups who were, you know, maybe
they were Series A or Series B.
They're like, we kind of get, you know, dropped into whatever phase they might be in.
It was never that perfect first, first moment.
Well, it was occasionally there were a few times when we, when we hit that, Flatiron Health was right at that moment, for example.
Digit was another great example where I remember being on the whiteboard with Ethan when he's like, I think it should work like this, literally just sketching out the idea.
But was sort of random.
Sometimes it would be this really perfect early moment where I think you and I have the most fun, and we think that we can help people the most.
But yeah, that was sort of
exception.
More often than not, the company was a bit further along and they always had interesting problems and challenges that we could help with, but it wasn't that really special start,
that special beginning moment of the company.
Yeah.
And obviously with the Design Sprint that John and I have been, creating evolving over all these years, we were really into the start.
it was, it was so cool to, to realize okay, we could craft this.
then so Character Labs is what came out of that.
we're on what this is the fourth time we've run it.
So yeah.
And.
called G3.
I mean, it's not confusing to me because I think for some reason I find it very amusing that we started with zero.
It's this nerdy reference that like let's start with zero.
But yeah, it's G3, which is actually the fourth group.
Yes, it does make the math slightly counterintuitive when you're trying to figure out what number we're on now.
So the, yes.
So the notion with Character Labs is start off with a foundation sprint, which is a thing that we do now.
it's kind of a very, very beginning, very early kickoff, sort of forming the, the rough draft of, of your strategy for the, for the project, and then go into a sequence of Design
Sprints And so this whole thing takes place over the course of four and a half weeks.
And it's.
It's really great.
gives teams a chance to go from kind of zero to having an idea of what the product might look like and maybe trying to build some confidence in product market fit.
And that's what we really tried to tailor it to.
What does it take to build as much possible confidence that you're on the right path to product market fit before you start building something.
So they leave Character Labs and they're ready to, ready to run in that direction.
And, and always having.
overcome a lot of dead ends and false starts because that's what happens when you are in the early stages of an idea.
The form of it won't be exactly right.
And we can figure that out in, days and weeks rather than months and years.
We have seven companies in this group.
We always try to find five companies, but more often than not, there's too many good options.
I think first time there were eight, the second time there were five, then I think now we've had seven twice in a row.
So we seven companies who are working with us.
And one thing that was meaning to mention to you was that...
One of the founders who's like, and pretty much all of the founders are like pretty technical, right?
They're mostly engineers or maybe an engineer who became a product manager or something like that.
but one of the founders who's an engineer, we were having lunch and he was like, it feels really weird to not be writing code.
Like I feel uncomfortable.
I feel anxious that I, I just like, I quit my job.
started this thing and I'm not writing code.
And I was like, yeah, I.
I get that, but also that's kind of the point, right?
Because when we look at what that team is trying to figure out in Labs it's like, well, what code would you write?
Because they have like kind of these two very different directions.
there's always some, I think if you have an idea of the market you're in and the problem you want to solve for customers, like there's always some foundational stuff you can start
building and sort of scaffolding, you know, infrastructure that you need to build your product.
But really
these two founders, they have two very different approaches to solving their customer's problem.
And so, I hope that by the end they will say like, that was different, but that was good.
now when we start writing code, we know that it's something that our customers want.
We know it's something that when we show it to them, it's really going to click with them.
but it was just, I don't think anybody's ever said it quite like that to me.
I don't think any founders ever been
just straight up like this feels uncomfortable to not be coding right now.
It was fascinating because that discomfort, mean, how true is that in all kinds of situations too, not just when you're an engineer who just left your job to start a
startup.
mean, You're like, my God, got to get this thing going.
We're always chomping at the bit to make progress that we can see in a way we're familiar with.
And I always feel that way when we start a writing project, I'm chopping at the bit to write words, you know, and, and it's very important though, to make sure that that effort
that can then unspool and quickly become, as I said, like months and years is headed in the right direction.
I mean, it's funny to think of it as slowing down because we're, we move so uncomfortably fast really in these sprints, but.
It's all about trying to make sure that that code gets written on the right, the right, create the right form of the right thing.
Have you ever done like a race, like a running race?
You know, like once, also at field day when I was a kid, But yeah, but only like once have I run a 5k.
So I ran track and cross country when I was in high school.
And I was just thinking about this because of the Olympics and watching sprinters.
When we work with teams, we usually run sprints, the name for how we work together.
And I was thinking about how obviously the race is fast, the work, if you will, of the race is fast.
That's the whole point.
But I was reflecting on how the moments before the race are the slowest.
moments of time possible.
And I think that's kind of what it's like when we work with startups in a sprint.
And maybe this is sort of like what that founder was saying about feeling slow, feeling anxious about not writing code.
there's this very slow period at the beginning, this uncomfortably slow period when you're sort of like getting ready and collecting your thoughts and like making sure that when you
do press go and go as fast as you can,
you're totally set and you're totally ready to make the most of that burst of energy.
Yeah, totally.
Totally.
I watched not a lot of the Olympics, but I did watch the hundred meter I was struck by one of the runners before they got even in the blocks, came out and was kind of just jumping
around, mugging for the camera and just.
And I was like, man, like save your springs.
You know, you're going to have to, you have to run like right now.
But I mean, obviously, and I think maybe even he won, but I was really impressed that what's that.
Yeah, it works for him.
Yeah.
But I was really impressed that like he's yeah, he's got like that much excess, you know, bounce and it still has, cause you, mean, at the Olympics, would have to.
You have to put everything in.
I'm imagining for that, for that stretch.
And, and it's, but it's kind of that nervous, you know, excitement energy that you feel when you're at the beginning of something new.
And so often I think that that excitement, it's really important and powerful, but it's really crucial to harness it in the right direction and, and, know, to get it pointed the
right way, because it's going to lead you off the blocks fast.
But if, if, know, if you're like running.
parallel to the, or I don't know, at the 90 degree angle to the course, this metaphor should probably stop immediately.
Yeah.
But in person, we were in person.
So that was wild.
I loved it.
It was so different.
And it's so funny that it was so different because we used to say, we're never doing stuff over a video.
We tried a couple of times in the pre pandemic era to do
Sprint Design Sprints with teams when people were in different locations.
And I just remember it being a mess.
It was so hard.
People's video and audio was always screwy and the collaboration tools weren't there.
We were used like Google slides or, you know, Google docs was just, it was just a mess.
And.
for background, you ran essentially the first Design sprint was in 2010 with the Gmail team, right?
And then you joined us at GV in 2012.
then like from then until COVID, like until 2020, we ran probably a couple hundred Design Sprints and maybe five of them were like remote or there was a remote aspect.
And usually it was
one unfortunate person who was in a different office.
And we were only sort of like half paying attention to them.
But yeah, when COVID started, we were like, okay, I guess we're gonna have to figure out how to do these sprints in person.
Yeah, we have to do them over video and we're going to, yeah.
then that was a struggle.
That was about a total pain.
And then it turned out Miro was really great for it.
And we've created templates in it now.
And now just like everyone, but we're doing so much stuff over video.
And it's turned out that with these startups, although I think you and I have been totally ready to go do sprints in person.
It's.
It just most of the teams are distributed.
usually it's the case that when you want to do a Design Sprint you should do it right away.
And it's hard to schedule travel and coordinate everything in time better to just get going.
So it was weird to do it in person again.
And also fantastic, but also felt weirdly, you and I both have this observation that it felt slow.
It was when you were doing steps with paper and sticky notes and whiteboards.
It's slower.
than if you're working in parallel over video and you're filling out things in a template that we've had the opportunity to design and think about and put the instructions in and,
it streamlines a lot of the, actual narrative and explanations we have to give.
And there's so many nice advantages to doing it over video, but it loses this one key thing, which is when you're actually in person, the connection that you make with the
people who you're working with is really powerful.
And our colleague, Kristen was saying,
There's also something about just embodying some of these things that are on a whiteboard or on the wall and you're physically putting, you're making a dia whenever you're making a
diagram of something or whenever you have like a lot of information you're trying to store and you put some stuff somewhere in the room and you can just kind of know like, I think
it's kind of over there.
It does.
memory where it's like, yeah, that thing lives physically over there, that thing lives physically over there.
It's different than when it's just all on a 2D surface on a screen.
Yeah, this used to happen more before the world of GPS driven maps, but when you give someone directions and, maybe you them like walking directions in your neighborhood and
you're like, okay, yeah.
So you go, like you go down and you're going to, you're to see like this big tree and then you're going to like trick like this whole part of your brain that if you're on a
whiteboard that's on screen, that part is not engaged.
I don't think.
whenever somebody gives me directions like that, I'm like, -huh, -huh, -huh.
And then like the second they stop, like, I didn't, I didn't, I didn't catch any of that.
Like, okay, yeah.
Okay.
The big tree.
Okay.
The third house.
All right.
Yeah.
Nope.
Totally lost.
it, to construct that 3D world in your mind.
My GPU is not up to the task.
man.
beginning to be slightly old models, slightly outdated models.
So I need an upgrade.
That's right.
Yeah.
Speaking of which, I just recently heard that possibly the first GPU, like the first time that that concept was really used where it was a separate processor that was just
processing graphics is the Nintendo entertainment system.
they wanted to create, spent a really long time developing it.
during the, and this happened kind of during the video game crash in the U S but they developed it originally for the Japanese market.
But part of the CEO's vision was this thing that's going to be way ahead technologically of the competition and, also inexpensive.
And so the combination of those constraints and they're like, it's okay if it takes us a really long time to build it, but we want to do those two things.
We want it to be way ahead of the competition and, also inexpensive.
And usually you can't be like, better and cheaper, but this notion that they spent years figuring out when they came up with was, well, we're going to use these sort of off the
shelf, even already in like 1983 or whenever they develop, it was already an old processor, but we're going to pair it with another one.
That's going to render the graphics.
And that actually was tough for other people to, to beat.
was, it was way ahead of what other things were doing.
I heard this on a on Acquired is the Acquired podcast, and it's, it's, you know, more about business than it is about tech.
So I, I don't, they were sort of like, we think this is the first time there was a GPU, but we're not, so somebody might.
hear this and say, you're wrong.
It was something else.
But, but I thought that was pretty fascinating.
anyway, a total tangent from what we were talking about, good one.
we were talking about directions.
We were talking about physical versus, virtual meetings and the, the power that has been durable of our, of our get together, at least durable for one week, cause this was just
last week, but this week we've been working with those same teams over video.
And it's remarkable to me seeing people over video, talking to them over video now, after having met them last week, it's so different because most of the time with our startups,
we, we go a long time before we meet them in person.
We might not meet them in person until after we've made an investment and maybe they come to our annual meeting or maybe we're visiting their city and then we meet them in person.
This was so different.
We meet in person right at the get -go and then now we're, we're over video.
again, it sounds kind of silly because in the normal way of doing things, you do start out in person.
But that there's something really valuable to it that in person is, is special.
And I remember this from the days of working at Google and working in the Seattle area and our office in Kirkland, which is across the lake from Seattle.
And that was where the engineering office was in, Seattle and the Gmail team, while I was working with was in Mountain View.
And so I would.
I would be working with the engineers that I worked with in Kirkland.
And then once a month, I would go down to visit mountain view.
And you probably experienced, you experienced this too, because you were in the Chicago office at first.
Yeah.
I, cause I worked at a startup called Feedburner in Chicago.
I was acquired by Google 2007 and most of the teams that I was working with were working on ads.
so both like the publisher side of like, where did the, like the AdSense is the name of the program, like ads that show up on, on publisher websites, but then also the advertiser
side.
So AdWords, which is like the tools to place your ads and
So those teams were like in, a lot of them were in New York.
So I remember like I would take day trips from Chicago to New York.
And some of them were in Mountain View.
I would also travel out to the Bay Area quite a lot.
Did you ever have a cadence, a length of trip?
What were those trips look like for you?
And what was your goal when you traveled?
I remember that my goal particularly, so it was a little bit different.
the Mountain View trips to me were more about relationships.
It was more about just hanging out with people and kind of being around and like going to lunch and like just, you know, sort of getting to know the teams a little bit better.
The New York trips I recall were often much more about having that
very high bandwidth communication pipe, you know, sort of that opportunity to like, just sit down next to somebody and just hammer through a bunch of decisions.
like, you know, pair designing, like two people looking at like, you know, I guess Fireworks probably what we use back then for design the UIs and just be like, okay, I was
thinking we should do this here.
And they're like, no, what if we did it this way?
I'm like, okay, cool.
Let's do it.
Great.
Okay.
Next.
Like, and I could, from Chicago, I could fly.
be in New York by like 9 a or 10 a pretty easily for a day trip and I could spend multiple hours there just cranking through stuff with the teams there and then fly back and be back
by like seven or eight at night.
As a side note here, a sort of a footnote, guess, Fireworks when John says Fireworks he's not talking about literal fireworks.
Fireworks was a design tool, a drawing tool that, I mean, it was a weird tool that we used at Google to design the UI back in the 2000s to draw pictures because it was pixel by
pixel and that's...
the way we were thinking about things for screens.
And it's of course been replaced by Sketch and now Figma, but it was like, for us, it was Figma at that time.
yeah.
And it was similar to Figma in the sense that it was one of the few tools that really was native to designing for on screen, designing for UIs.
Photoshop was always about, well, the name implies, editing photos.
Illustrator was, again, as the name implies, always about creating illustrations or artwork.
But Fireworks really was for designing on screen graphics.
It was one of the like
quirkiest, weirdest tools.
But it pioneered some pretty interesting concepts.
What are they called?
I think in Figma, they're called components or symbols.
Basically, idea, maybe I'm thinking of they're called something different in Webflow as well.
But this idea that you could have, if it's a button, you can create that button as an object.
And then you can have that same button design show up everywhere.
If you edited the color or the curvature, then it would update everywhere.
But you could also have aspects of that element, like the label, the text label, that could be different per instance of the button.
And that's something that I think we take for granted now in design tools.
But I think Fireworks created that.
I think they were the ones to come up with that idea.
Which is really a wild idea to come up with from now, if you don't have that idea and then you, know, it's, that's a huge one.
I mean, I I went from, I come from working at Microsoft and there we would design our mockups using Photoshop, which is not, you know, not intended for that kind of work and
Fireworks What?
Yeah, it was better, even though was like a much, in many ways, like a lower quality product.
could just, you know, Photoshop been around for many years and it's more robust at that time, but.
Yeah.
Anyway, that's a, sorry about, sorry about that diversion, but I, a little nostalgic for fireworks, but that idea that you would make a trip in a day and, either to collaborate or
to have that in -person, that sort of relationship booster or both.
And I would do the same thing from, from Seattle.
would go to Mountain View for, for a day and leave in the morning, come back at night.
And it was a.
It was an interesting time at Google because I mean, the teams were really pretty small and it was sort of easy to go down and in a day meet the people you needed to meet with
on, maybe a few different projects, maybe meet a couple new people who were, leading up other projects and build this.
Like, I always felt like you're kind of refilling a bank account of
rapport, you know, like you, when you're away from people for too long and working together, I think there's a natural, a natural thing that happens where we start to feel
like they're, they're the outsiders and like our tribe is just the folks here and that we're working with the same person.
Yeah.
an abstraction of a person instead of a whole person.
Yes.
And I think it's probably a survival thing from, you know, like days of, of your, like you, you can, you, you know, you can read the people who you are around all the time.
You, you know, you can develop a confidence that they're trustworthy.
And, and when you don't see, when you haven't seen someone for a long time, you have to sort of redo that, all that assessment of, I trust this person?
Anyway, obviously we trust the founders that we invest in, but it's.
Just a different feeling having come off of working in person.
And now it just feels so much better working over video.
I also though, came out of that thinking, okay, I have a bunch of ideas for how to make the only do the physical stuff on the wall and on the whiteboard.
That's really the most powerful and do everything else using, using Miro, even in person, because it's going to be faster and more efficient.
It's going to feel like we.
we spent our time well.
Although I still think we spent our time well, but we can do it even better next time.
Yeah, we're always trying to get better at how we run sprints and how we run Character Labs It's a, that one 100th.
Yeah.
My favorite thing about doing Character Labs in person was being able to much more fluidly move between the teams and help them out.
And this is, this is really like part of our pitch to founders is when they participate in Character Labs that
We're going to invest.
That's the table stakes.
We're going to write a check, small investment in each of the companies.
But then we're going to work with them.
They're going to get to work with us and with Eli, our partner, our co -founder, who's been a VC investor for almost 15 years now,
And so that's like the promise, right?
That's the pitch of Character Labs.
And I think that the in -person version of it delivers on that promise much more fully than the remote version.
And some of it just has to do with the physical or logistical ease of like, I'll just take three steps over here.
And now I'm looking at the whiteboard for, for team X
Yeah, there's, it's funny to sort of, were in this big room, we booked this big, I don't know what like massive conference room in a, in a hotel that's where we were kind of
camped out for three days.
And so during that time, it's really cool.
Like you walk around and like, okay, right now every, all of these teams are working on their differentiation and they're figuring out like, what's going to differentiate them
from the competition.
And so you walk around and look and you can just like,
drop in and get involved in that conversation.
That was really cool.
Cause that's like.
could be like, that, you know, honestly, this doesn't feel that differentiated.
Like, you know, this doesn't feel like an area where you are really, where you really have an advantage over your competition.
is there something else you can consider and be able to do that in 30 seconds, you know, just like step over and like do that.
So cool.
then the geographic reference, can picture in my head now when we're, as we're online talking to these teams, I kind of like, okay, those guys, right.
They were over there.
can see their, I can see their thing like on the wall, you know, something like my mind's eye.
like, it's all, it's all there.
I that's the way our brains are wired.
Like that's anyway.
TLDR, that was cool doing it in person and, also fun to be back home and, know, be able to be in sprints every day and then afterward, be at home, which is, which is what I dig too.
So it's kind of the best of both worlds.
And I don't think we could have done this,
long program so easily.
It would have been very challenging to put this together and get the same kinds of teams as involved, as focused as they are, if we were trying to do the whole thing physically in
person.
we're lucky.
Yeah.
Totally.
Yeah.
The I actually, this is related to what we talked about at the very beginning.
I'd had email installed on my phone.
all last week, because in addition to Character labs, we also, we were hosting our annual meeting, which we had about 95 people, many of our, our investors who are LPs and then
many founders, not just the ones who are in Character Labs but other founders we've invested in.
Everybody was gathered together and I was running that meeting.
so I just had, I had email on my phone.
It was like this very like sort of busy kind of like lots of, lots of moving pieces
Over the weekend, so we had the annual meeting on Tuesday and on Wednesday, Thursday, Friday was Character Labs.
I uninstalled email from my phone.
I didn't look at my email from Friday night until Monday morning, which I don't know the last time I have taken that long of a break from email, but it was a very good and very
needed reset from the intensity of last week.
Well, part of our whole mode of operation for the last decade plus has been we will do something that's radically different from the way other investors work.
We're going to work together with teams in these like intense bursts where it's days, even weeks at a time working together all day, every day, and trying to line those up when
it's.
A great moment for the company when it's a, you when they need that help, great, we can, we can offer this to you to do that though.
It/we have to, make sure we're marshaling and balancing our own energy in the right way.
Because a, like you, you can't do that every day.
You can't do that every, every week.
And I remember like a high water mark in terms of number of sprints per year.
There was probably a time at Google ventures where we did like maybe up to like 30 in a year or something.
And it was almost every week.
Did you occasionally have a week off?
And it was something that, you know, a younger Jake could do for like a year or two years.
like it, but it's like, it's not sustainable in the longterm.
have to figure out how to balance it.
So you're really doing the best work and also so you have enough time to have these other conversations with founders to be picking good companies and to be,
kind of aware of like, are we working in the best way and continuing to like find the best spot so that we're not just continuing to assume that the plan or approach that we came up
with a decade ago is still the best one.
Yeah.
The other cool thing that happened this week actually, one of our portfolio companies was acquired.
Yeah, it's really exciting.
Yeah.
So this was, this was an investment originally that you and Eli made.
you like, me the, give me the quick backstory.
Yeah.
Okay.
So the company is called Reclaim and they have a product that basically manages your calendar with AI.
you, yeah, you give it some, some information.
say, these are like my, my habits.
have, I think they did a pretty good job with like the nouns in the product.
Like they have habits.
it's like, what are the things you want to make sure that you do that often, you know, kind of get pushed to the side.
exercise, lunch, leaving the office at a certain time, whatever, sort of define those things, tell Reclaim about those things.
The next noun is tasks.
So it's like, what are the work projects you need to get done?
And a lot of times that comes from a task management system.
You know, people use all different tools for that.
And then, and then meetings are the other thing.
So you kind of tell it the meetings you need to have, and Reclaim sort of, it sort of
Shuffles all those things up, you know, just like you would imagine if you had like a really great assistant working with you and kind of, lay out your calendar and, an optimal
way.
there's a bunch more to it, of course, but that's kind of the simple concept.
And, A few years ago, this was in 2020.
Eli and I had started, we basically had decided we were going to start Character but we hadn't raised our first fund yet.
We were still kind of in the planning period.
And I had been writing a newsletter.
back then called Time Dorks, which became Make Time, our second book.
And I remember I had written about this idea of scaffolding in your day, in your schedule, and that you should set up some scaffolding.
Just like you're painting a building
You you could put up a ladder and you could paint, but then you'd have to like walk.
You'd have to climb down, move the ladder, go back up the ladder, paint again.
Very inefficient.
If you put up the scaffolding, you can stand there.
You've got a nice solid surface.
It's secure.
It's safe.
And you can, and then you can just move.
You could paint, you can work freely.
You can use both of your hands.
and I think if you can create some scaffolding in your schedule, you can say this is, these are the big building blocks of my day.
These are the things that are important.
I need to make sure that I.
that I eat and I exercise and I have time to unwind that you can work with both hands.
You can be more free to do the work that really matters to you.
So I had written, a newsletter about this and I get a response from Patrick Lightbody and Patrick is the founder of Reclaim and he said, hey, love your newsletter.
We actually have.
built a lot of these ideas into our product Reclaim And one thing that people listening should know about me and you is that we have tried like a zillion different like, you
know, productivity, like tools and different calendars and, you know, similar to like buying if there's a new type of phone available, we'll try it out or a new type of, you
know, a device we're going to try it.
Like same for software, right?
If there's a new thing that's going to like help us better use of our time, like we're going to try it.
So I had tried a lot of things and I was a little skeptical at first, but I checked out the product and it was really interesting.
It worked really well.
Eli and I get really excited about investing, but we hadn't raised the first character font yet.
So we invested, he and I as individuals.
later we ended up transferring those shares into the first Character fund But yeah, that was the backstory of our investment in Reclaim.
I remember John introducing me to the idea of like, you know, you got to kind of design your day and the calendar and then the calendar becomes reality.
So that's a way to like control reality for yourself.
That's a good, powerful concept on the individual level.
It's really hard to create software that will make that happen.
Make like an individual habit concept, come into real life.
so many people have tried.
Yes.
Yeah.
So many people have tried to do those things and especially something that can do it at the level, not just of like help any individual access it, but help like a team of people
access it here.
We sound like we're giving like a big pitch for Reclaim And at this point, it doesn't matter.
They've already been purchased.
So, you know, you could use them or not.
we just recommend it because it's a product that might help you in your life, but we will not accrue any future benefit.
yeah, probably won't be acquired again.
Yeah.
Yeah, won't be a quality.
Yeah, so it started as this angel investment by me and Eli, then a Character ended up investing a couple of times.
made an initial investment and we ended up then making a big bet on the company and making quite a large investment.
And part of why we decided to make that large investment was because we had worked
you know, in between sort of the beginning and then that, that big bet, like we had worked with them.
We had worked with, Patrick and Henry as co -founder and gotten to know some of the rest of the team.
we had run sprints with them.
I remember, you know, you mentioned in passing this Foundation Sprint which is what we do in, in Character Labs.
And one of the, one of the earliest Foundation Sprints that we ran, we had a different name for it back then.
We called it an Opportunity Sprint which is we could probably spend.
three hours describing the differences.
won't, we'll spare you that.
Yeah, the 10 hour episode, it'll be like, what's that Taylor Swift song that has like the eight minute version?
All too well, I think it's called.
There's like the normal length and then there's like a version of the song that's like eight minutes long.
Anyway, so we had run basically a Foundation Sprint with them.
they were kicking off a new project.
they already had, know, Reclaim existed in the market.
But they were at this important moment for the company where they were going from like single player mode.
So it was a tool you would use to help manage your own calendar to like multiplayer mode, which is where you could now use Reclaim in a team inside like a company.
it becomes like...
exponentially more complicated and more challenging from a technical perspective, but also from a product perspective.
Cause you're just having to think about, well, you know, just anytime you, sort of open multiple calendars to see like, let me try to schedule a meeting.
it's automatically tricky.
And to think about like a UI for doing that in an automated way, it's just like this, this potential like complete.
you know, black hole of like, like, complexity and discussions and debates about like the best way to do it.
I think now they're, you at the time of the acquisition, had like 300 ,000 monthly active users.
think 40 ,000, more than 40 ,000 companies are using Reclaim.
So they, they, they grew quite quickly.
and so when we see that combination of like, okay, there's, there's strong quantitative evidence that you're onto something and we've been able to see behind the curtain and work
with the team in a sprint and build our own conviction.
That's sort of the magic recipe for us to.
you make an even bigger investment into a company, which we did in the case of Reclaim.
Cool, cool story.
pretty exciting.
think that I like, my hope is this will mean a lot more people see this product and get it in their hands.
I know that was a lot of the motivation for the founders was like, Hey, a lot of people use Dropbox.
it's not easy to grow an audience as a, tool that you use at work.
A lot of people do already have Dropbox in their work life.
So we, we hope that it'll, it'll get to a lot more folks and help them make better use of their time.
That's kind of the, the bottom line.
Yeah.
One final cool thing about this is that the acquisition of Reclaim by Dropbox was really driven by the CEO of Dropbox.
he actually, when Dropbox went public in 2018, the CEO Drew like described
this future where essentially a tool like Reclaim would exist.
But I just pulled it up and he wrote, imagine getting to work in the morning to find your calendar reorganized so you have a three hour block of time to actually focus.
Imagine starting your day and seeing the perfect to -do list, one based on a deep understanding of your priorities and your team priorities.
So Drew Houston, CEO of Dropbox, he wrote this in 2018 in like the
the filing, you know, when the company went public, he was like, this is part of the vision of the company.
And so then like, you know, fast forward to early 2024, six years later, and Reclaim had like, built all of that quite, but like had a pretty darn good start on building that.
So when they got connected, there was just really good alignment between what the Reclaim...
founders were trying to do and what Dropbox was trying to do.
definitely great to see that it wasn't just about the financial side of it, the deal, which of course is important for us as investors, but to see that there's something more
to this acquisition.
Yeah, totally.
it'd be really interesting to see what happens.
mean, as we all sort of know Dropbox is this ubiquitous utility.
And then I think they're, they have been trying really hard to figure out how they grow beyond being this ubiquitous like file utility.
And they have a lot of software tools.
And I said, like a huge audience of a lot of people who, who use the product.
But for many people, it's just this thing that just works.
Like I don't think about it.
It's just a pipe.
It's a way I send links to people to files and the ways I make sure that my files are on different computers and just works.
I, that's like a really good, from our standpoint, being super time nerds, that's a really powerful vision to have in the pre AI boom.
Like, if AI was sort of doing this for you
Yeah.
Well, before we sign off, we share a couple of recommendations?
You have anything to talk about?
Actually, I'm going to kick off.
going to answer my own question.
I have a request for a recommendation.
I recently was looking for a great timer app for my phone.
And it's been a while since I looked for an app like this.
There's really a lot of junky apps out there.
just, I want a timer that just like will repeat.
I want to set like a time, like two minutes and just have it like count to zero and then to start over again, without having to, what's that?
I am using it like for stretching basically, like I have a whole bunch of, I have like a bunch of different stretches that I do and this is maybe, maybe too, too nerdy, but like,
I, I just, I do the math.
like, okay, I have 15 before like my next thing.
it's like seven, seven blocks of two minutes is like 14.
So I can just like do two minutes of each of these stretches.
That's like seven stretches.
That's When I have 15 minutes before doing something, I get distracted for 20 minutes.
That's usually my approach.
So, so I applaud you.
I actually have, maybe I may have the thing for you.
Yeah.
The bit timer app is called bit timer.
Yes.
And I think it's still, I think it's still great.
Like, I'm just, looking in the app store.
I've used it not long ago, but I'm looking in the app store right now because I want to make sure.
Bit timer.
Yeah, I remember this one.
end up with like an old version of an app that's like better and then they kind of don't get up somehow.
Yeah, no, bit timers are there.
Look, not very popular.
It only has, I mean, it has like 4 .8 star.
It's kind of, yeah, totally, totally right.
like gone into like app store spamming or like advertising or like, you know what I mean?
Yeah.
It's like a simple, I think it's just like a simple app that a guy made and it's like well -designed yeah, it just works.
So, it's developed by Peter Buick.
Like just looks like a guy.
yeah.
So bit timer.
It's great.
Nice visual design, good sound effects.
just does that.
It's just a timer.
It's great.
Well, anybody, if you're listening and you have any suggestions, you can send us an email.
Yeah.
Can you beat bit timer?
That would be phenomenal.
Yeah.
Request for recommendation.
one other quick thing on that.
I, I probably tried like 10 different apps.
Like this was over the weekend.
I was like looking for an app, like one of them that I installed and you know, apps have gotten like really aggressive about, the in -app purchases, with like subscriptions.
you run into this?
Yeah.
Crazy.
I installed one and the,
There was no free trial.
It was like, OK, you have installed this app.
It was like free in the app store, but in -app purchases.
then the first screen was subscribe now.
And the price guess, guess the price.
Guess the subscription price for a timer app.
It was just a timer app.
Yeah, yeah.
Was a per week per week subscription.
week?
So I'm trying to think in my mind what's the least amount that you can actually bill on the App Store.
I mean, given that the bit timer exists and is so great in this, I don't know if it's free or if you pay a one -time thing, but is it 49 cents a week?
what's the least you can pay?
49 cents a week, I guess.
Yeah, that's my guess.
one half, the price was $17 per week.
What?
Wow.
I can't fathom what you'd be timing where it would be worth that much because we all have like, if you have a phone, you do have like a decent timer because the built -in timer on
phones is like not bad.
If the right, but like I'll manually repeat for like $18.
mean, unless you're just, that's all you're doing.
21st.
Wow.
That's a bold move.
Somebody was really like, I'm just going for it.
a dark pattern for like, like, like I want the app click, let me try it.
Yeah.
it's like a dollar.
Yeah, that's, that's yeah.
Wow.
That's wild.
Yeah, I was so I also on that, I should, here's my recommendation for people, because it has sort of segues.
It's this, this, these episodes on the podcast Acquired about the history of Nintendo.
And so it's, it's really like three episodes.
It's two about Nintendo, one about like Nintendo from.
founding of the company, which is actually like the 1890s up until the sort of 1990 -ish, which leaves them kind of on the top of the world dominant with the...
I'm not going to go too into it I'm super fascinated by Nintendo and have read some other stuff about their history and well, maybe that'll be a deeper dive on a future podcast.
But that's episode one is like from the 1800s to...
Like any S dominant and then episode.
in the 1890s?
Playing cards, okay.
I playing cards.
Yeah.
And originally it was like a cement company.
then the, they, like shifted to, they created this new company basically with like, I think like the capital from the, which was this.
great passion for games.
Well, playing cards, I think it was a big business opportunity because they had been illegal in Japan and they became legal, but gambling was still illegal.
gambling was how people really used playing cards because like in a casino, if you were gambling, you would use a fresh deck again and again again.
so their main customers for a long time were the mob basically, like the Yakuza.
but like over time they got into doing other kinds of like games and toys.
And then that was sort of their, what interested them and made them aware of like the emerging world of like arcade games and then ultimately consoles.
But the first episode and Acquired which is a, I have not listened to this podcast before, but it's sort of, you know,
profiles of businesses in its long form.
So they're like each episode is like three plus hours.
it's enjoyable to listen to what they, they go, they go up to 1990.
The second episode is about like basically up until today.
And it's, it's also interesting because Nintendo just basically has this
this cyclical pattern of big hits and then big flops and, and seeing how they man, anyway, we'll, we'll, we'll go into it a bit in a future episode, the third episode is about Sega,
how Sega kind of took over the market from Nintendo in the nineties and then lost it.
and like almost went out of business and that's fascinating too.
The whole thing is fine, especially if like me, you like.
lived through that as a kid and you know, so really fun.
But the hosts were talking about Apple and how, know, Nintendo and Apple have, there's a bit of a similarity in terms of wanting to really put the customer first and really have
this walled garden
high quality, we're going to be the gatekeepers and make sure that the, games that are available on the console in the case of Nintendo or the, you know, the apps that are
available on the app store are like of a higher quality.
And that's sort of a promise to you.
the hosts were sort of making the point that Apple kind of set out to do that, but the app store has really like devolved over the years as it has been a bigger and bigger, like.
cash cow perhaps you know, it's very hard to say no to revenue.
Plus the hardware sales have like plateaued in a lot of categories for Apple.
They're still selling, you know, literal boatloads of everything, but like they're not growing as fast.
Meanwhile, like their services, like apps, like, subscriptions for like Apple TV, Like that stuff continues to grow.
So it's really important for the future of the company, but yeah.
see, do they, you know, where do they lose their stamina for their standards?
And I mean, you know, the fact that like the parental controls don't reliably work on everybody's phones and like, it's kind of spotty.
some people I know are like, no, I can turn Safari off.
because of writing the distraction -free iPhone articles and make time, like I hear from people about this and it's mixed and like, my son does it actually.
And he's like, yeah, like I got it to work after trying like 20 times.
It's just like.
One time worked and now I just not touching it, but when they launched screen time, they never would have let this happen that year.
You know, like their attention was on it, but they didn't have the stamina to keep making sure that everything works because it's not a big part of their business.
It's like, it's just a good enough promise.
And it's sad when you see that happen, but that happens.
And that's kind of the app store too.
Like, can you imagine if in the early days of the app store when
You know, Steve jobs was like on stage talking about how like, don't need fart sound apps.
Like if there had been a timer that charged $18 a week to use and like people would have noticed, cause when there weren't a lot of apps, people have been like, wait, look at
this.
is crap.
Like this is just taking advantage of people.
And you know, now you cut to like, well, for 12, 14 years later, like their standards might be a little looser for what they allow in the app store.
Cause they're reviewing everything.
They hypothetically
In theory, they should know that that's the business model for that app.
And that is probably just hooking people in and then like silently painting their subscription.
The other thing is if you try to ever unsubscribe from something that you've subscribed to on the phone, or especially if it's something your kid has subscribed to, it's almost
impossible.
Like you have to look up a help app and like you have to go into like iTunes on their computer.
Like it's just, it's just, yeah.
It's like, clearly they don't want you.
to figure it out.
you know, everything else is just, tap in here.
And it's a just a little switch and settings.
And it's like right there.
They don't want you to unsubscribe.
Yeah.
Right.
Yeah.
yeah, it's, it's interesting.
And you know, it kind of comes back to that story about Dropbox acquiring Reclaim.
That's something that like, we have very limited control over as investors, but it's something that we think about in like,
you know, talking to founders about how to make those decisions.
And it is important to try to think about the longevity of the product and where your, you know, your vision that we also see founders when they're just in the early stages
beginning with what's the best chance that has of living on for as long as possible and having the best incarnation in the real world.
And we have like, optimism about it, but it's, it's tough in the real world.
So, anyway, would request, recommendations from listeners for, stuff that you've read or heard about Nintendo's history that you found interesting, because I'm really fascinated
on the topic right now.
And I've, I've read a couple of books about the, the
sort of the consoles, especially in the, for me, it's really fascinating.
Like the, the seventies, eighties, nineties, what happened there.
one that's on my reading list as Console wars.
hear about that one a lot, but it's just such a fascinating story about differentiation and figuring out how to stand out from the competitors because it's tangible because a lot
of us have had like a visceral experience with these products.
I just think it's.
there's a lot of interesting lessons.
So if you've heard of something great, if you've heard a great podcast, great interview, let me know.
All right.
I think that's good for today.
Thanks for listening everyone.
Yeah, yeah, thanks so much.
And if you, you want to find out about the work that we do with founders, you want to learn more about Character go to character .vc If you want to find out about new episodes
of this podcast, please subscribe.
We would really appreciate that.
Whether that's Spotify, Apple podcasts, wherever you like to listen, or go to the sprintbook .com.
You can sign up for our newsletter there and we'll, we'll send you an email when we've got something to share.
Anything else, Jake?
All right, until next time.
Bye bye.
Thanks.