#10 - Henry Shapiro: Reclaim.ai, AI Scheduling & Time Management

Welcome everybody, once again, to Road Work Ahead, a podcast that explores the unmapped future of business and technology. My name is Sam Gerdt, and today I'm talking to the co-founder of a company that has, without exaggeration, changed my life. I'm talking about Reclaim.ai, and my guest is Henry Shapiro.

Most people are familiar with the negative impact of meetings stacked on meetings or poor time management in the workplace. As our jobs get more complex, so does the task of managing an effective schedule.

Reclaim is an AI scheduling tool that does the work of time blocking for you. On top of this it gives you tools for managing meetings and establishing habits, guarding your time against the invading forces that so often steal your lunch hour or pull you away from deep, meaningful work.

Henry and his co-founder Patrick built Reclaim as a solution for teams to minimize disruptions and do more meaningful work, but Henry admits that no one expected such an overwhelmingly positive response to their product. Even in our interview I found it hard to contain my own enthusiasm.

Also, just a quick note: Henry says reCLAIM, I say REclaim . . . Potato, PoTAHto. Enjoy the interview! 

Episode Transcript

Sam Gerdt (00:07):
Welcome everybody once again to Road Work Ahead, a
podcast that explores theunmapped future of business and
technology.
My name is Sam Gerdt, and todayI'm talking to the co-founder
of a company that has, withoutexaggeration, changed my life.
I'm talking about Reclaim.
ai, and my guest is HenryShapiro.
Most people are familiar withthe negative impact of meetings,

(00:29):
stacked on meetings or poortime management in the workplace
.
As our jobs get more complex,so does the task of managing an
effective schedule.
Reclaim is an AI schedulingtool that does the work of time
blocking for you.
On top of this, it gives youtools for managing meetings and
establishing habits, guardingyour time against the invading

(00:49):
forces that so often steal yourlunch hour or pull you away from
deep and meaningful work.
Henry and his co-founder,Patrick, built Reclaim as a
solution for teams to minimizedisruptions and do more
meaningful work, but Henryadmits that no one expected such
an overwhelmingly positiveresponse to their product.
Even in our interview, I foundit hard to contain my own

(01:12):
enthusiasm.
Also, just a quick note Henrysays Reclaim.
I say Reclaim, potato Patato.
Enjoy the interview, enry.
I think I'm most interested tohear about those early
conversations around Reclaim andhow you intended to build this

(01:32):
product.
What was the problem that yousaw and what were some of the
solutions that you were thinkingabout at that time.
Then let's get into how Reclaimactually came to be.

Henry Shapiro (01:46):
My co-founder and I, Patrick, we met one another
at a company called New Relicwhere we were both product
leaders.
I think experienced firsthandthis challenge that I think a
lot of busy middle managers,middle to senior end, just lots
of professionals experienceinside of companies where,
especially as companies getbigger, people's calendars get

(02:07):
less and less aligned with whattheir actual priorities are and
what the teams and companiespriorities are, and more and
more aligned with meetings.
A lot of the important workthat I think we were focused on
was happening in our off hours,in the evenings and after work

(02:27):
and on the weekends.
I think we just felt thatcrunch and that strain and also
were people who never had thebenefit of executive assistance
and wondered about whether therewas a better way for us to help
people with that problem.
I'd say also, the other piecewas just more at a kind of

(02:49):
philosophical or maybe moreconceptual level.
I think we were really intriguedby this idea that we have all
these systems in our lives thatare either partially or very
intelligent, that help us toautomate and orchestrate all
kinds of infrastructure thathelps us get through our days.
The systems we use to manageour time have been using the

(03:11):
same data, the same data model,the same metadata for like 30
years now.
They basically all operate onthis idea of you're free or
you're busy In our world.
We understand that there's alot more nuance to how our time
operates than that.
Our belief was that if we couldbring a lot more intelligence
into the calendar and a lot morecontext about what mattered to

(03:33):
people, we could make theircalendars and their lives better
, solve that first problem.
But we could also start tounlock some really interesting
challenges that just hadn't beensolved around how people find
time with each other.

Sam Gerdt (03:48):
You're probably looking at your bosses and
seeing them with their personalassistants and you're saying I
want that for me.
I see the benefit that thatwould bring to me.

Henry Shapiro (03:59):
There were two processes that really stuck out
to us, I would say.
One was I noticed that all ofthe executives that we worked
with you had EAs, had thisweekly process, and sometimes
multiple times a week, wherethey would sit down and their EA
would say, hey, okay, so whatare your priorities?
They'd look at, they'd have thecalendar pulled up, they'd have
a task list or some kind oflike scratch pad pulled up and

(04:20):
they say what are yourpriorities?
They would literally go throughthe calendar and try to go
through this kind of process ofstriking things through on the
calendar that were sort of likeokay, that's lower priority,
let's push that, let's punt that, let's delegate that.
The other thing they would dowas if that executive were
trying to get six people in aroom that were all super busy in
the same week, that EA's jobwas to go around to each of

(04:43):
those folks and say, hey, itlooks like you've got an event
here that I'm pretty sure youcould probably skip or delegate
or you could maybe decline ifyou need to.
Are you okay skipping this inservice of getting this more
important critical meetingscheduled?
Those are really the twoworkflows that we thought about
as like we could definitelyautomate that.
Those are two things we couldat least help people to do on

(05:07):
their own.

Sam Gerdt (05:08):
You started out as an AI company.

Henry Shapiro (05:11):
We started out as an AI company.
We started about four and ahalf years ago.
I'd say we'll get into it, I'msure a bit more.
But our perspectives on AI Ithink we're very much like
there's kind of this balance, Ithink, especially with
calendaring, between sort ofblack box AI, where you don't
necessarily know what the knobsand dials are doing under the

(05:32):
covers, and this sort of moredeterministic sort of rules
based or business logic based AI.
We really focused, I think,initially more on the latter,
mainly because we felt likepeople are pretty new to this
idea of putting a bot on theircalendars or putting some kind
of automation in their calendars, and people are.

(05:53):
They want to have control overtheir calendars.

Sam Gerdt (05:55):
Ultimately, Well, absolutely.
I think there are a few peoplethat I know who have brought on
EAs into their business owners.
They're busy, they run theirbusiness and they don't have
time for things like email.
They don't have time for thelower level tasks.
There's this huge mental hurdlethat they have to get over in

(06:19):
order to entrust something sopersonal as email or their
calendar to someone else.
Everyone I know who's done this.
They talk about how the firstmonth is just torture.
It feels like it's never goingto work.
It feels very uncomfortable.
There's all kinds of thingsthat slip through the cracks
After a month.

(06:39):
There's just this switch thatflips and all of a sudden now
everything is running so muchsmoother than it ever has.
It's super interesting to thinkabout bringing the executive
assistant down to lower levels.
Most of us don't have access tothat kind of resource, but

(07:01):
through artificial intelligence,all of a sudden we're gaining
access and it's unlocking all ofthese crazy things for us.
Hey, everybody, just a quicknote here.
We're about to get into somequestions that talk about my own
enthusiasm for reclaim as atool to deal with some of the
problems that come up forsomeone with ADHD.
One thing that you may rememberabout me from a few episodes

(07:23):
ago is we talked about how Istruggle with ADHD and ASD.
A big part of that struggle istime management.
Before we get too far into it,I just wanted to make that clear
.
The enthusiasm that I have forthis product and the way Henry
talks about this product, you'llsee that there's a little bit
of a difference there.
I don't want my own comments toget in the way of Henry

(07:45):
explaining what is truly arevolutionary product for all
kinds of teams in all kinds ofindustries.
One of the things with reclaimthat I'm really curious about
and I'm wondering how you talkedabout it in the early days and
maybe even how you talk about itnow.
The tool is really helpful forpeople who struggle with time
management.
Specifically, I think aboutpeople with ADHD who listen to

(08:11):
people like Cal Newport.
They're familiar with conceptslike time blocking and they want
that so badly for themselves,but they're just terrible at
doing it.
I fall into that bucket ofhorrible time management and
that's why reclaim is sovaluable to me.
You guys don't market yourselfas a product for people who suck

(08:31):
at time management or peoplewho have ADHD or any of that,
whereas you've got directcompetitors who are doing that.
They're saying we are an ADHDproduct.

Henry Shapiro (08:39):
I'm curious why that is yeah, I mean I would say
there are a couple reasons.
The first is maybe somewhatpersonal, although I guess maybe
it's somewhat personal in thesense of I have a lot of people
in my life, including my partner, who are pretty severely ADHD.

(09:03):
Seen the ways in which itpretty uniquely affects all
kinds of stuff Time, blindnessand the feeling of getting over
focused on tasks and then thewhole day windows away.
I don't feel great at somelevel and I think we have talked

(09:24):
about it internally and I thinkwe've said we don't really feel
great about leveraging that toour advantage in a way I don't
know quite how to put it exceptthe feel that it just felt
didn't feel right.
Occasionally I would look atsome of the posts from certain
competitors where they weremarketing themselves that way
and I would look at comments andI could tell that there were a

(09:46):
number of folks from the ADHDcommunity that felt like they
were being a little pander to.
Perhaps I think that was partof it was just feeling like we
love that people and we hear itfrom tons of users in our user
base who tell us about the factthat the tool really, really

(10:08):
uniquely helps with ADHD.
There are even folks who,independently, have gone out and
told that story for us, andwe're actually really happy to
have them be telling that story,because I think the other piece
of it is like it's sort of likespeaking to the problem when
you don't yeah, when you don'thave that connection to it, I
think is really important.

(10:31):
But I'd say more so than that,even just at a just pure
business level, I guess Ourbelief is that this is like this
is a very universal problem.
I think that it's a fairstatement, although ADHD is a
very unique sort of scenario.

(10:51):
I would make the argument thatwe are all kind of living in
this era of a ridiculous amountof distraction and a ridiculous
amount of chaos.
I mean these sort ofexternalities that people have
to deal with on a day to daybasis, as well as all of the
just fatigue from all of theways in which we're being
constantly drawn in like 20different directions.

(11:12):
I think it's really hard for meto envision a person today who
doesn't have some kind of likeschedule, time management
problem, and so I think our goalis actually to kind of bring
more and more of the market andmore and more of kind of the

(11:34):
audience.
Right now I feel like just basedon thousands and thousands of
conversations with people overthe past few years, there's kind
of three segments to thismarket.
There's 5% of the world thatsort of is really really open to
this idea of having, like an AIassistant or like a smarter
calendar at their fingertips.
There's like 15 to 20% ofpeople who are even open to

(11:55):
tools like Calendly that arelike highly sort of structured
they're basically just ascheduler that sits on top of
Google and then the vastmajority, I think, of people are
like their maturity aroundcalendars is super low, and so
our goal is, I think, to bringas many people into that
category of folks who understandthat they have a problem and

(12:17):
also understand that there aresmarter solutions out there to
it.

Sam Gerdt (12:22):
Yeah, it makes so much sense.
What you're saying definitelyresonates with what I know, and
that is the majority of peopleeither are on top of their
calendar game, they're Type A,they're super organized, or it's
just a mess.
And what's really interestingis for a tool like Reclaim,
which in some sense takescontrol of your scheduling.

(12:44):
If you already have control ofit, you end up hating the
product because you feel likeyou're playing tug of war with
something that you didn't ask.
You're not ready to delegatethose tasks.
But for those of us who lovethe idea of time blocking, maybe
we even have prioritized tasklists, but we struggle with

(13:05):
whether it's time blindness orbad task management Our
schedules are constantlychanging on us and we don't have
the time to adapt and build outa new schedule.
A tool like this is absolutelylife-changing For me.
It was life-changing.
I've shown it to other peoplein our company.
It's life-changing.
I've shown it to other peoplewho are friends and they're just

(13:30):
.
Usually, as soon as I mention itand there are a few keywords,
people will perk up Really andit's funny to see what they are.
It integrates with Todoist andthey're like really.
Or if you get sidetracked orderailed and something doesn't
get checked off.
You don't have to go back andre-block your time, it just does

(13:51):
it automatically.
Really, you've got somethingthat everybody wants, but not
everybody's articulating it inthe same way.
It's so interesting, butbecause there's that disconnect
between the people who reallywant it and the people who
really don't want it, I'veactually found it very difficult

(14:14):
to incorporate this as an appfor whole teams.
Usually, whole teams aren'tinterested in using it because
you have at least a couple oftype A's on your team and
they're like I don't want thismanaging my calendar.
So it does seem to be somethingthat's more supplemental to the

(14:35):
tools that we're already using.
Is that accurate?
Is that something that you guysconsider?

Henry Shapiro (14:42):
Well, I think that even within the type A
group because I know definitelythe group you're talking about
and we have quite a few of thosefolks in our user base I would
say People who are very on topof their calendars were on top
of their calendars before theystarted using Reclaim, but they
still recognize, just like anytoilsome job, that there's a way

(15:05):
in which automation still helpspeople who are type A.
They may not view the productin the same way, they may focus
on different types of featureswithin it, but I think even
something as simple as I have apersonal calendar and I have a
work calendar and I want to makesure that my work calendar gets

(15:25):
blocked out for personal eventsthat is an automation job.
That's the first feature weever built, and the reason we
built that feature was becausewe felt like this is one of the
most understandable and it'skind of one of the safest
problems that we could startwith.
It's not asking people tochange massive behaviors.
It's literally like here's ajob to be done.
It's super annoying.

(15:46):
Whether you're type A calendarmanagement guru or not.
It's just stupid.
You have to go and createmultiple events and keep them in
sync.
You're not a computer, and so Ithink those types of features,
as well as things like habits,even for people who are like I
block my lunch out every day.
It's like cool.
Does reality ever get in the wayof that?

(16:06):
Do you ever find that yourlunch gets overbooked?
And then what do you do?
All the other meeting timearound that lunch event got
overbooked, and so they kind ofsee the ways in which I think we
lean into.
Things like flexibleavailability, automatic
rescheduling and those types ofbenefits also kind of, I think,
can be helpful for those folks,even when they're fairly on top

(16:29):
of their calendars already.
So I think we went over adecent amount of those folks.
But there's definitely, I think, also folks who, the same way
that you mentioned that personwho gets the EA, and maybe it's
months before they actuallyreally trust that person with
their calendar there's alsofolks who I think to that
earlier point about having tobring more folks into the fold
who I think are just maybe notready to get there yet and our

(16:51):
hope is that over time enoughpeople starting to use tools
like these will sort of promptthem to move in that direction.

Sam Gerdt (17:00):
How does it affect the, I guess, the company
culture, the vibe, whatever, Imean all the work that you do?
When you hear the people saythis product moved the needle in
my life in a significant way,Was that expected?
Did you expect to build aproduct that could do that?

Henry Shapiro (17:21):
No, I would not say so.
It's really been.
Honestly, it's still to thisday and we get feedback like
this on a weekly basis,sometimes daily basis, because
we have a fairly active supportprocess where people can chat
with us and talk to us.
That was a thing very early on.
That was very important to uswas, as we grew, continuing to

(17:47):
have really personal and deeprelationships with our users, to
understand A how we're able tomake the product better and let
them know that there's a teambehind this that's there to help
and make their lives better.
Patrick and I worked onmonitoring software for a very

(18:08):
long time developer tools andyou would hear things from those
developers that were like oh, Ireally like XYZ tool, it's
really nice, it's really cool, Iuse it in my work, but we've
never worked on products.
I think that never worked on aproduct that has gotten to the
types of things that we hear,like Even things as simple as

(18:29):
hey, I ate lunch five days, youknow a week for the last six
months, and I like haven't donethat since I started working
professionally.
Or I just had like my mostproductive work week ever and
I'm really excited for next week.
Like it's still pretty mindblowing and we have a, you know,
obviously a whole channel andspace where we share that with
the team and I think it's reallyfor all of us like the thing

(18:51):
that keeps us really motivatedand it's very unique for us.
I definitely was not something,I think, that we anticipated or
expected and still, I think tothis day, very much surprises us
because I think it's we knowand hope that the product is
going to.
You know, we took a lot of careto build the product and we

(19:14):
invest a lot in trying to makeour users' lives better, but the
impact that you can have onpeople just by doing simple
things for their schedule or,you know, complex but simple
things for their schedule ispretty astonishing.

Sam Gerdt (19:29):
You're coming from a place where you're building
tools for developers and you'vehad startups in that space.
You've had products in thatspace.
You're coming to this.
It's much broader market.
How has that changed just ingenerally?
How's that changed yourthinking and what are the
challenges associated withswitching like that?

Henry Shapiro (19:49):
Yeah, I mean, when we first started the
business, our original intent weactually didn't even start with
the idea of building a calendarproduct, believe it or not had
nothing to do with calendars.
Initially, our focus was thequestion we were asking was how
would we make teams, productteams in particular more

(20:09):
productive and what metricswould we look at and what things
would we automate?
And we, being DevTool people,started with like GitHub and
Peter Newdy and all these thingsthat we think of as like
developer toil, showed it to abunch of engineering leaders,
showed it to a bunch of productleaders, and they all kind of
said like meh, like that's cool.
But, honestly, if you were toask me why I'm struggling to be

(20:32):
productive, it's because I'm inlike eight hours of meetings a
day and there's no time for meto get worked on.
There's no time for me to, like, spend time with the team or
work on design sessions or dothe things that I know are
really important, and then I'mdrowning in email and
notifications and all the restof it.
And so that's what led us tothe calendar, as we sort of said
like okay, that's so, that'swhere that data lives and that's

(20:54):
where that's where all theaction is happening, and so we.
Originally our theory was thisis going to be really useful for
product teams.
You put something out into theworld and it turns out what we
were really building, I think,was this more kind of flexible
platform that could be utilizedacross a whole bunch of
different use cases, and beforewe knew it, we had students and

(21:18):
consultants and people in salesand people in engineering, and
executive leaders and frontlinemanagers and senior ICs, and
it's a universal problem.
So I think, in some ways, Ithink our emphasis has had to be
on continuing to build aplatform, and that is also.

(21:39):
That is a.
It's a, it's a benefit and it'salso, I think, it has a
challenge associated with it.
If we were working towards likea single optimization, if we
were like, hey, we're a productthat really embraces eat the
frog, or we're a product thatreally embraces Pomodoro, we
could build all of our workflowsaround that, but we would very
narrowly focus ourself on thegroup of people who care about

(22:00):
that one type of optimization,and we'd have to have this like
really strong opinion thatthat's it.
We have a strong opinion thatyour calendar should be aligned
to your priorities, but then wetry to give you a set of
flexible tools that can helpalign it to that and schedule
around that.
And so we have to kind ofcontinue building a platform, I
think, in order to aid as manytypes of people as possible.

(22:22):
And then from a go to marketstandpoint, I think the you know
challenge, and I'd say the waywe've kind of weathered it is
really by focusing our effortson the two groups that have kind
of emerged as our sort of toptwo kind of enterprise use cases
.
One is sales and specificallypre sales, and the other is
engineering.
Those two groups, you know,together make up about 60 ish

(22:46):
percent of our user base, soit's a relatively strong
concentration.
But then there's of course thislong tail of folks who get
value out of the product for allsorts of different reasons.

Sam Gerdt (22:55):
There's like you mentioned.
There's that there's thatsubset of people, that 40%, who
are using it as part of either apersonal or a small team's tech
stack.
What's your vision, then, forthe product?
Does it continue to like fitinto a tech stack, or does it
become its own platform?

Henry Shapiro (23:13):
Well, first I'd say you know, our belief has
always been that enterprisesmight buy software.
But people use software.
And so we've always built and Ithink we'll always build with
the individual in mind.
I, my belief, is to yourquestion about.
We get asked this question allthe time for users like hey, are
you going to replace Asanasomeday?

(23:34):
Are you going to replace, youknow, Todoist someday?
And we like to think about itin terms of, like, we're a small
team.
We have, you know, just likeany small team.
You know only so much we canfocus on and do well at a time,
and so we really think about,like, what's the biggest set of
like unsolved kind of greenfield problems where we think we

(23:56):
could add value anddifferentiation?
And for us it always comes backto scheduling.

Sam Gerdt (24:02):
Do you guys know what a green field problem is?
Because I didn't.
I had to look it up.
A green field problem is aproblem where there is very
little or no work that you canbuild upon.
So in this case, Henry istalking about scheduling being a
green field problem, and theidea is that the available
resources that you have to drawfrom is so limited that you're

(24:23):
essentially starting fromscratch.

Henry Shapiro (24:26):
Project management, like there's lots of
interesting problems in projectmanagement, but there's also
some some pretty well worntracks out there and there's a
lot of work that would go intous being a true project
management platform or being aeven the subset of like meeting
agenda.
You know products that are outthere.
There's a lot of work andworkflow that goes into those

(24:48):
things.
It's very people are alwayslike we just throw projects in
there and put a con bonboard in,you're done, and it's like,
yeah, okay, until there's like a300, I've seen Jira's feature
request board, so I think Ithink for us it's really going
to be about how can we be thesmartest scheduling engine first
and foremost period, and ourbelief is like these big

(25:10):
databases we use, these projectmanagement systems we use, that
are basically just collection ofwork, like they help you
capture the work.
They don't help you get the workdone and we would be like we
would like to be the productthat helps you get the work done
.
Does that, on some timeline,lead us to a place where,
because we're the downstreamplatform that helps you get the
work done, we maybe start to dipour toe into project management

(25:33):
?
Like, sure, potentially, but Ithink there's so many
interesting problems for us towork on around meeting and sort
of product productivityscheduling use cases that I
think we feel like it's a that'swhere our focus is going to be
for the foreseeable future.
What?

Sam Gerdt (25:48):
sold me on reclaim was its integration with Todoist
.
Not, when I.
When I first started using theproduct, I had a zero interest
in inputting tasks directly intoreclaim none.
I was already very pleased withTodoist and the way that
reclaim seamlessly integratedwith Todoist was the big seller.
There was no weird setup thathad to happen, it was just I

(26:12):
could put it into Todoist and itwould be on my calendar where
it needed to be.
That frictionless integrationwas what made your product to me
so valuable.
Is that something that you guyscontinue to look at and work on
?
What should we be integratingwith?

Henry Shapiro (26:26):
Yeah, absolutely.
I would say the next kind offrontier for us is likely going
to be CRM.
There are all sorts ofinteresting workflows that come
out of those products.
I mean, those products havetasks in them as well, which is
something that you know.
If we, if you've never workedin sales or or or haven't known
people who do, you almostwouldn't know that or like think

(26:49):
like well, what do salespeopleuse for project management?
They use Salesforce or HubSpot.
That's where they keep alltheir tasks and projects and
they've got like.
Gantt views and projectmanagement views the same as
anyone else, and and so there'sthere's tasks that come out of
those systems that are reallyinteresting, and then there's
also other types of schedulingworkflows that are really kind

(27:12):
of fascinating to us.
We've been making a lot ofprogress over the past few
months and just recently putinto private beta this kind of
new prioritization system thatwe've been working on for a
while.
But one of the things thatwe've been looking at is how to
be basically how to use thatpriority to send more or less
availability to people based onhow important the meeting is.

(27:33):
And so there's all theseinteresting use cases that flow
out of that around customer andsort of you know, customer
facing types of meetings, whereurgent meetings kind of get
higher priority and higherbilling and get more
availability and lower priority,you know, sort of opportunities
or things that are just furtherout on the calendar, just not
necessary to happen this week.

(27:55):
Those get a little lessavailability, and so there's
just all these interesting ways.
I think that we could startkind of digging into CRM.
So probably CRM is really thenext big stage for us.

Sam Gerdt (28:05):
Hey everybody, just a quick note that I'm about to
derail this interview once againwith my own enthusiasm for the
product.
Henry just got done, saying alot of very good things and my
response was essentially yeah,but here's what I want from it.
So, anyway, I hope you'llindulge me and forgive me just
this once I'll try not to do itagain.
Keeping in mind that wholepersonal assistant thing, I

(28:26):
would love to see moreintegration with those stacks
that people are using to kind ofbuild that personal assistant
out in their own lives.
Sales people do have HubSpotand Salesforce and we all have
some form of task management,project management, but we also
have email integrations that wewant to see I would love to see.

(28:47):
One of the big things that Ialways look for in products
today is some sort of naturallanguage UI.
Yeah, ever since Chad GPT kindof hit the scene and blew up,
natural language UI is just it'sone of my favorite things to
see in a product.
So, yeah, keeping it in thatdirection too would be like I'm

(29:08):
rooting for you guys to keepthat.
I do want to talk a little bitabout the brand, because this is
something that's come up a lotin the interviews that I.
This podcast tends to focus ontechnologies, but it's always
fascinating to see how brandcomes into it.
One of the things that we wantto do with these interviews is

(29:28):
point people to where theyshould be thinking or what they
should be doing in the face ofdisruptive technology, and the
thing I keep coming back to overand over again is like I really
feel like the most importantthing a person can do right now
is focus on their brand.
It's just give the brand thedevelopment and the love that it
needs to become a conveyor ofthe emotion of the company, of

(29:52):
the value of the company.
And so I'm really curious totalk to you a little bit about
how you built a brand in the AIspace, which is kind of a.
It's a newer space, it's a morecompetitive space, a lot of new
companies coming in and it's astartup.
So there's always that you'retrying to push product, but

(30:14):
you're also needing a brand inorder to push product.
So I'd love to hear a littlebit more about the origins of
the Reclaim brand.

Henry Shapiro (30:23):
Yeah, I mean I think from the very beginning
there were kind of a few kind oftenants.
We really looked at one of ourfavorite brands from a just
corporate branding and, I wouldsay, founder led branding
standpoint was actuallyAtlassian.
That's probably one of thebiggest inspirations for us.
Patrick, way back in the day,was an early.

(30:45):
He actually built the originalGira workflow editor with Mike
and Scott and co-authored acouple books with them in the
Java realm, and so he had veryearly exposure to Atlassian.
I think was very kind ofinspired by their kind of
approach.
And I'd say that the things thatreally stuck out to us about
their brand that we wanted tokind of emulate were kind of

(31:06):
transparent.
No BS Like that was a reallyimportant piece to us.
We didn't want to sell fluff,we didn't want to overmarket our
solution to the point of sortof losing the context of what it
really did.
And the transparency alsomanifested itself not just in
terms of, like what we put onour website, but how do we write
about what we do, how do wesupport customers, how do we

(31:30):
kind of talk about the problemsthat we're trying to solve, and
so I think that was kind of atthe core of it was like we
really wanted to be a brand thatcame across as highly
transparent, obviously trusted,but sort of transparent and no
BS.
I think there's a kind ofhumility.

(31:55):
I think also that both Patrickand I tend to have especially,
I'd say, in the realm offounders, where that is not
always in high supply and Iwould say that we really wanted
that to come through as well.
I mean, I think sort of a sensethat there's a sort of small,
scrappy, hardworking group ofpeople behind this.
And even as the company grows,I think we still want people to

(32:18):
have that impression thatthey're kind of, they're doing
business with and working with ateam that responds quickly, is
pretty agile, changes directionwhen they need to, but isn't
like thrashing the product orthrashing the direction, has a
vision of where they want to go.
And I think the last one waskind of like playful fun, like

(32:38):
we wanted to be a brand thatpeople didn't view of, like
there were so many productscoming out at the time that
we're all going after thesuperhuman interface and
superhuman is an awesome product, don't get me wrong but it was
all everyone trying to buildlike black and white apple style
kind of branding very kind ofslick, think, you know brushed
metal branding, but minus theskeu-morphics and we were very

(33:00):
like no, we kind of want to be alittle like fun and colorful
and we want people to feel likethis is a problem that isn't
about being overly kind of rigidand, you know, sort of gray.
We wanted people to feel likethis is a problem they can have
fun with and a problem thatactually they can sort of dig

(33:22):
into and feel like good about.
And that was part of where,like, the onboarding came from
and a lot of the colors andanimations and brands me a lot
of that stuff really kind ofcame from our feeling of like we
want this to be a fun brand too, because we also want it to be
a fun company for us.

Sam Gerdt (33:39):
You can kind of tell when a company is trying to
bring another brand into theirown.
I think about, like you know,open AI has a very distinct look
their website, their products,their all their design, very
distinct look, and I see thatlook more and more incorporated

(34:00):
into other AI startups who arekind of trying to latch on and
convey that feeling.
When I look at Reclaim, I don'treally see any of that and in
interacting with the brandyou're right, it does come
across as being a very scrappyteam, like I've never had any

(34:21):
problem talking with people atthe company, like whether it's
through the Slack community or,you know, on social media, it
seems like there's alwayssomebody who's available.
I think I've even posted aboutReclaim in the past and gained
followers from the companythrough those posts.
Yeah, like your team seemsgenuinely interested in just

(34:45):
being being people connectingwith people.
There's there's so much outthere.
How do you differentiateyourself from the next guy?
Is it just?
Is it just chasing that humanconnection?
Is it being humble or is therelike I mean, what would be the
Reclaim playbook for saying wedon't want to look like the

(35:08):
average AI company.
We don't want to get lost inthat noise?

Henry Shapiro (35:11):
You know I'd say generally speaking, and then
I'll speak to the AI piece.
Generally speaking, I would saythat our it kind of comes from.
We built this culture, I think,and Patrick and I still to this
day we both answer supporttickets.
Like we spend time in support.
We spend less time than we dida year ago, but if you look at

(35:32):
the stats on the board, like weprobably still have more support
tickets closed than anyone elsein the company, because in the
early days that's what we didwas was we talked to every user
that came into the system thatwould write into support, would
talk to either Patrick or myself, and so part of it, I think, is
staying really close not justto the problems like that you're

(35:52):
hearing about in the ether,because there's lots of
interesting problems out therethat get discussed in the world
and then there's also a lot oflike echo chamber stuff that
gets discussed and people forgetabout how complex and nuanced
these problems really are.
Like they're not.
As soon as you pull a thread onanything calendar related and
think of a space where, inaddition to it being a very

(36:13):
complex workflow, the margin forerror is incredibly low.
Like you, cannot you mess upone event on the calendar and,
understandably, someone loses alot of trust quickly.
And so I'd say it really comesfrom listening to our users and
hearing the good things that arehappening, the bad things that

(36:34):
are happening, the way our brandshowed up to them, the way that
they interpreted something thatwe showed to them in the
self-serve process, like welisten to those things and we
try to tweak them and make thembetter and make them better and
make them better.
And there is no, as far as Iknow, there is no magic lever to
it.
It is just like keep, keep,poking on it and poking on it

(36:55):
and poking on it until it'sbetter.
And there's going to be thesebig moments, you know, for us as
a company, these big releasesand big.
We have big ideas of things wewant to do.
But it's those, it's all thoselittle tweaks and all those
little interactions with peoplethat I think compound into
something really great.
And there it's also the reasonthat I think we have people on
the team who also internalizethat for themselves, because I

(37:18):
think they recognize that that'sthat's part of the fun of
working at Reclaim is like youbuild something.
It gets out to customers withinseconds.
You have hundreds of thousandsof people using it and they're
all giving you feedback and theiteration cycle can be really
fast and it's like that's.
That's fun for developers too.
It's fun for people on the teamwho build anything here.

Sam Gerdt (37:39):
Did you hear it?
Did you hear it?
I heard it.
We've talked about this before.
You don't just add a technologybecause it's there to add.
You add a technology because ithelps a person.
You add a technology because ithelps you fill that brand
purpose.
It helps you accomplish youroverarching goal, which should
be rooted in the good ofhumanity.

Henry Shapiro (38:01):
On the AI front, I think there's a little bit of
a solution looking for a problemin some cases with certain
types of you know applicationsof this stuff, like people who
are just kind of like slap aslap a generative AI or slap a
GPT on it.
And so I think, like thecritical thing for us is always
thinking about so GPT, just asone practical example is really

(38:23):
good at doing things like youknow, taking a bunch of event
data or a bunch of calendar dataand trying to understand what
that date, what that text issaying, you know what, what's
the priority of this event, who,you know which of these events
might be flexible or might bemovable, like it's actually
pretty good at doing that.
It's actually alarmingly bad atdoing normal, just basic

(38:46):
scheduling.
It has no real, like some ofthe examples that are provided
in some of the, the white paperswe've read through and some of
the tests that we've done, it'sit's not very good at doing like
bin packing math.
Yeah, the good thing is we'rereally good at that.
And so I think the theopportunity, I think what I
would be looking out for as faras like differentiating

(39:07):
ourselves, is really thinkingabout those interfaces as
primarily great engines andgreat ingestion sort of points
for calendar, event data, emaildata, slack data, all sorts of
stuff that gives us context, andthat context is what we want to

(39:27):
use to drive better schedulingon the calendar.
Because, again, our, ourcontention is that most of the
time, scheduling is not a mathproblem, it's a negotiation
problem, and so that's reallyhow we think about splitting the
market.
I'm very wary of companies thatare pitching the executive
assistant thing and where itdoesn't appear that they've done

(39:50):
a whole lot more than, like,basically just put a wrapper
around GPT, yeah, and I thinkthat's where, like, you have to
look at a company that has beensort of thinking about this also
from a business logic, coreservices standpoint, to kind of
drive those workflows.

Sam Gerdt (40:06):
So two weeks after this interview was recorded,
open AI announced a new productthat essentially allows you to
take your own training data andtrain chat GPT on that data.
It's very easy to do you don'teven need to be a developer to
do it.
But what this means is that allthose companies who built a
custom interface for what wasessentially chat GPT those

(40:27):
companies are all now instantlyirrelevant and we're going to
see a lot of them going bye byereally soon.
In my own pursuit for that AIexecutive assistant, it's been
very simple to realize thatthere's no one solution,
especially something like GPT.
But you see glimmers in all ofthese little things and you
recognize okay, well, as long asthe integrations hold together,

(40:51):
I'm going to get a little bitfurther with a new tool here, a
new tool there.
That was what was so veryexciting about Reclaim the idea
that it just worked with the fewother apps that I was already
using.
I don't know why that's sounusual, but as somebody who is

(41:17):
working on text acts forbusinesses all the time, I can
tell you it's incredibly unusualto just plug two pieces
together and have it just workthe way you want it to.
When I see these pieces of AIappearing here and there.
What I'm rooting for, what Iwant to see is I want to see
people see the good part of it.

(41:38):
I want to see developers seethe good part of it and say,
well, we could use that to makeour product a little bit better,
rather than looking at it as astandalone product.
And I think there's, like yousaid, there's been too much
taking it and making it astandalone product with a new
brand slapped on top of it.
That's why I mentioned earlierGPT is a good UI.
I love chat GPT as a UI becauseI don't need my mouse and

(42:04):
keyboard anymore.
I can just talk to my computer.
That's the big reason why I'vealways loved Todoist is because
they give you a single text boxand then they give you just it's
really easy to ingest acomplicated, complex task with
one text box.
So all of those little thingscoming together being plugged in

(42:24):
together to make that thatpersonal assistant we're getting
.
We're getting ever closer tothat, just little by little.
I'm really hoping that we cansee products like Reclaim, take,
take the good from these AItechnologies that are coming out
, apply them thoughtfully andand just very modestly, very

(42:47):
humbly improved to the point towhere you're saying you know I
wouldn't use Reclaim foreverything, but I would
certainly never lose it, like Iwould certainly keep it plugged
in.

Henry Shapiro (42:56):
There's all these actions that you take inside of
our product today.
You know you're familiar withthem because you use tasks.
You know, if you want to say Iwant to kind of change the order
of this task and reschedulethis thing and start this thing
and like right now, that's awhole bunch of like button
clicks and so, like, some of themost immediate use cases for us
are literally to your pointabout user interface is just
like just give people theability to express what would be

(43:19):
a fairly complex instructionset and let Reclaim sort of work
it out through.
You know, touching all the.
We already have all theservices that drive all the
stuff.
It's it's just a matter ofchaining all together.
You know the actions based on aprompt.
And so I think, like our first,our first kind of interest is
around like how can we reducejust friction in using the

(43:42):
product?
And that's really, I think,where we see the big opportunity
around GPT right now is likethere's certainly a intelligence
component to it, like we couldlearn more about the calendar,
we could do less, put lessmanual tagging effort on the
user, and that's also part andparcel of the equation.
But I think there's also justthese workflows, whether they're

(44:03):
meeting scheduling or taskscheduling or whatever, where
you're trying to tell Reclaim todo like 15 things and rather
than you having to go andindividually tell it to do 15
things, just tell it to do onething and or several things
within one prompt and let us letus go sort it out and preview
it for you.
You know the sort of idea of aI need to get time with these

(44:25):
six people by the end of theweek and then a bot that is sort
of going around and queryingindividuals, you know, sort of
automatically, and they're allhaving conversations to the side
, and then that thing comingback to you and saying like
here's what I found and here's,you know, here's the re, here's
the kind of recon that I've done.
There's something really magicalabout that and it in some ways,

(44:46):
it's kind of like.
I think a really good way ofthinking about some of these
kind of problems is is like,does this feel?
Does this feel human?
Like does this feel like athing that I was already doing?
It's just a little faster, alittle smarter and significantly
cheaper and in both in terms oftime and actual dollars, to to

(45:08):
pull off.
And that workflow I justdescribed is one that I mean.
That's what people are doingtoday.
They're just doing it with eachother or, if they're lucky
enough to have a full timeexecutive assistant, they're
doing it with that person sortof in the mix in like a slide
room or an email thread.

Sam Gerdt (45:23):
As part of a small company, with a small team, we
still we're not even in a bigspace and we still struggle with
that to coordinate, say.
Say that you want to get threepeople in a room together at the
same time.
It's it's becoming moredifficult to to accomplish that,
as you know, as teams grow, asthey get more busy, especially

(45:45):
if you're trying to pull inpeople from maybe different
disciplines, differentdepartments.
So, yeah, it's reallyinteresting to think about how
an artificial intelligence cantake that legwork and and and,
silently, just maybe maybe it'snot even like it's accomplishing
it for you, but it's presentingyou with options.

(46:05):
Who are you listening to in, inkind of in this space, as you
as you're, as you're looking outthere?
Who are you taking inspirationfrom?

Henry Shapiro (46:15):
I think that the you know there are definitely
some people in this space who Ithink of as really smart in and
around scheduling as it relates.
So there's a company calledCalcom.
I probably shouldn't promotethem because technically there
may be a competitor, but theyhave a founder this guy, pierre

(46:36):
Richardson, who's a bit of acurmudgeon but also like really
smart on scheduling and justreally gets like this space in
some pretty fundamental ways.
We're in very different partsof the market.
He's looking at this kind oflike open source in you know
calendar as infrastructureopportunity and I think we're
thinking a lot more kind of likewe're integrating with the

(46:57):
services that enterprises use,like Google and Outlook, and
trying to kind of build abusiness around that.
But certainly like that, youknow, in the scheduling space
specifically, he's a reallyinteresting voice and really
just like appreciate the workthat that they're doing there.
Really interesting company too.
And then you know, I think we,we we listen to there's a couple
of folks on the kind ofproductivity front, one of whom

(47:21):
is actually an investor of ours,this guy, john Zeratsky, and
which they started a small fundcalled Character.
It's based out of Milwaukee andthey run these really amazing
like design sprints for theircompanies and also are just.
He wrote a book called MakeTime a Long Time ago and was one
of our earliest investors,actually as an angel.
We connected with him becausehe sent out a newsletter that we

(47:42):
subscribed to and we poked himand said, hey, we're building
something that's kind of likewhat you talk about, except
we're trying to build it intosoftware.

Sam Gerdt (47:48):
If you've never heard of the book Make Time by Jake
Knapp and John Zeratsky, can Ijust say go read it.
Let me read you something fromtheir website.
Make Time is not about crushingyour to-do list, optimizing
every hour or maximizingpersonal productivity.
It's about rethinking thedefaults of constant busyness
and distraction so you can focuson what matters to you every

(48:12):
day.
The book is like five years oldand it is still so good.
This is exactly the kind ofmindset that we need in tech.
This is the kind of mindsetthat we need in work.
It is exactly what I needed tohear several years ago when I
read it for the first time.
I cannot recommend it enough.
You guys need to go to thewebsite maketimeblog.
You're going to find a lot moreabout them there.

(48:34):
Go check it out.

Henry Shapiro (48:36):
He's just got a ton of really awesome
perspectives on like he's verymuch.
He and his partner, Eli, areboth just like really important,
like kind of mentors for it Notmentors, advisors for us as we
think about the company, butalso advisors for us as we think
about product concepts and howthey affect different types of
users.
And then I'd say, first andforemost it's kind of cheesy,

(48:57):
but our customers, our users,that's who I would say we take
the most inspiration from and welisten to the most, because
they're the people who I thinkare best positioned to kind of
influence our thinking andthey're closest to the metal.
I mean, there's no one closerto the metal than the person
who's using your product,especially the person who's

(49:18):
using your product completelyunassisted by you and running
into all sorts of oddities andproblems and things that you can
make better for them.

Sam Gerdt (49:26):
So for my part, this has been a bit of a personal
journey for me, this whole ideaof kind of it's almost like
you're facing your demons.
You have to figure out, like,how you work and how to optimize
because there is so muchdistraction coming in.
So on that front, I think ofthat book, john and Jake, and

(49:49):
that book and as a designer Istarted as a designer I read
Sprint and they've done a lot ofexcellent work.
But then also, like Cal Newport, the way he talks about
productivity has beenparticularly helpful and a lot
of times it's really frustrating.
A lot of times you read theseguys and they're dead on, but

(50:11):
then you go to execute.
Like Cal Newport, he's alwayslike you just got a time block
and then that's the extent of it, like he'll show you how to do
it, but then you go to actuallydo it and it's like well, I
can't.
My brain stops there, and that'swhy you look at reclaim and
it's like, well, let me do thatfor you.

(50:32):
And it does it really well.
That's the other thing thatjust I'm always.
I'm a little bit amazedconstantly at how well it works.
I've kind of grown accustomedto it now, but like it's always
fun just to see how well itworks.
Sometimes I go into my day andI'm just like is it going to
know that I really need to dothat thing for most of the day,

(50:54):
because I know I gave it a lot.
Is it really going to know?
And sure enough it knows.
And even when it misses andmaybe it puts something else
there, I always find it's like,yeah, I guess I should do that
thing too, though.

Henry Shapiro (51:08):
Like.

Sam Gerdt (51:09):
I'm zeroed in on something and it's saying yeah,
but you really ought to give 15minutes to that other thing over
there.
So you know, I find myselfarguing with it sometimes, but
then I have to admit the feetusually because it's like I
can't argue with a math basedentity.

Henry Shapiro (51:25):
Well, some days you'll be able to.

Sam Gerdt (51:27):
Yeah, but I'll still be wrong.

Henry Shapiro (51:30):
Yeah, you know, I think one of the things we
loved about Make Time and aboutJohn's book was just the degree
to which I think you know he'ssomebody who has been in big,
busy software companies withcrazy, hectic, terrible
schedules and I think hisemphasis on simplicity and sort

(51:51):
of like pick your, pick your top, like pick just theme your day
around, like the top couplethings you need to get done.
It's super powerful and it'sone of those like yeah, no duh
things, but people reallyoverengineer this stuff.
And that was what reallyresonated for us was this idea
that it was like look it's, it'sreally complex, it's very
nuanced and hard.
It's not to say this is easy,but it really is to some extent

(52:14):
as easy as saying like groundyourself in the most important
thing and many other things willflow from that and don't get
too caught up in, like themechanics of it and where it
gets challenging.
And I think why you knowoftentimes you know the the plan
doesn't survive.
Contact with the enemy, so tospeak, is you're in a vacuum

(52:37):
with a calendar that has noinbound commitments and no
inbound conflicts and no inboundrequests for time.
Time blocking would workperfectly.
There probably be no need forsomething like reclaimed.
Besides the pain of movingthings around, it's the it's
this tension that we're allfacing between.
Ok, I need to be available, butnot too available, so that
people can find time with me andthey don't slack me all the

(52:59):
time.
So my calendar isn't completelyfull, but I need to have like a
little bit of leeway to get mywork done.
I need the ability to kind ofbe agile when things change and
have things move and kind oftruncate and shift around as
needed, and I need a way to kindof express when my own
priorities change.
And doing all of that yourselfon your own calendar is really

(53:23):
painful in a busy organization.
I think that's what we reallyappreciated about John's
perspective was it was comingfrom somebody who really had
lived that life and, I think,understood that there wasn't.
There was this real set oftensions between what people
know they should be doing andwhat happens in reality when
they when they actually get intoit.

Sam Gerdt (53:43):
Well, it was.
It was a concept, though, thatsaw people as being human and,
and you know, human in theircapabilities, but also human in
the sense that there's morestuff that they want to do than
just work.
And so the idea of embracingall of the things that you love
and asking that question well,well, like what, what do you

(54:04):
want to do today?
You know they.
The book is made up of.
I could talk about the book fora long time, but the book is
made up of.
You know 100 or so strategies.
You know little little tacticsthat you can use, and you're not
expected to use all of them.
You're expected to mix andmatch, because everybody's
different.
Yeah, but one of the tactics was, you know, ditch the to do list

(54:24):
and create a might do list.
You know, yeah, yeah, it's,this is my might do list.
This is a list of all thethings that eventually have to
get done higher and lowerpriorities, but this is not my
overlord.
Yeah, and I feel like that's.
I feel like reclaim has hasdone a good job of merging the
to do list with the idea ofyou're a person, who, who is

(54:49):
going to just do some work today, and we want to chip away it as
much of it as we can, butobviously it can't all get done
today and we're not going tomake it your overlord.
It's such a comfortable place tobe and I feel like it's really
nice to find a tech company anAI company, you know, a
scheduling company even who issaying let's just treat people

(55:12):
as unique people and give them atool that takes friction away
from them having a really goodday with whatever they're facing
.
It's such a powerful purpose.
You know, remind me, do youguys have, do you guys have,
like a codified brand purpose?
I don't know if we've ever sat.

Henry Shapiro (55:27):
I mean, I think one of the things that we, you
know, talked about for a longtime, was a more perfect work
week.
You know, I think we probablyhaven't spent as much time as we
probably should aroundestablishing like a snappy
snappy brand purpose statement.
It's sort of evolved andchanged, I would say, over time.
I can't recommend enough theplatform.
I continue to talk about itwith other people.

Sam Gerdt (55:46):
It's.
It's an excellent tool.
I'm really honored that youwould be willing to come on here
and talk with me about it.
This is it's a little bit of a.
It's a little bit of a, I don'tknow.
This was a special interviewfor me.
This was an awesome, awesomeinterview.

Henry Shapiro (56:02):
And I really appreciated the opportunity to
come on and really trulyappreciate the investment that
you've made in in our productmeans a lot, and and the degree
to which you've incorporated itinto your life and the degree to
which it's impacted you is, asI said early on here, it's still
something that, to this day, isit makes a huge difference for
us.
It's it's you know why we getup in the morning, and so I

(56:26):
thank you for for taking thetime and for having me on.
Yeah, well.

Sam Gerdt (56:32):
I mean, I can't again .
I can't express the change thatyou know.
It saves so much time and itturns planning my day, something
that I dread, to something thatjust doesn't even it's it's,
it's fricking crazy.
It just doesn't even it's it's,it's frictionless.
So yeah, it's my pleasure,absolutely my pleasure.
Thank you, sam, appreciate it.