Latest / AI for Founders with Ryan Estes / The AI EA Flex

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The AI EA Flex · AI for Founders with Ryan Estes

0:00
AI is coming for the part of your job that you hate.
0:02
The e-mail back and forth, the just checking in follow-ups in
0:05
the time zone, math at midnight. And honestly, good riddance
0:09
because the founders who figured this out first aren't working
0:11
more. They're finally working on the
0:13
right things, but most founders are still grinding through the
0:15
irritating stuff themselves. It's like a badge of honor.
0:19
You're scheduling your own meetings, chasing your own
0:21
confirmations, managing 3 calendars like it's 2011.
0:24
I think I've got 4 calendars. Meanwhile, some folks just
0:27
handed all that to an AI agent and reclaim 10 hours a week
0:30
week. Here's what the modern workflow
0:31
actually looks like. Now you CC your AI executive
0:34
assistant on an outreach e-mail, forget about it, and three
0:36
follow-ups later, that person becomes a customer.
0:39
You didn't touch it. You tell the agent to protect
0:41
your mornings and block time before every holiday through
0:44
2027, juggle your calendars across Singapore and Dubai time
0:48
zones, and it never bats an eye. The people on the other end,
0:51
they think they're talking to a human, unless they don't.
0:53
And maybe they'll jump on board too.
0:55
You're not managing your calendar anymore.
0:57
You're kind of sculpting your life and your agents are
0:59
painting the details, so it's kind of fun to think about.
1:02
If AI is absorbing all the work that was too tedious for me to
1:04
do consistently, what do I want to do with the time that it
1:07
frees up? Welcome to AI for Founders.
1:09
I'm Ryan Estes, and today's guest is Will Rubin, former
1:12
Instagram exec who helped build Reels from the ground up and is
1:15
now on a mission to give every founder access to an executive
1:18
assistant through Workmate. If you're drowning in the busy
1:21
work that's quietly killing your momentum, this one was made for
1:24
you. Every week at AI for
1:27
founders.co, we drop the tools, tactics, and frameworks that
1:30
actually move the needle. This is founder fuel.
1:33
Join thousands of builders who read it before breakfast.
1:35
Your next unfair advantage is 1 newsletter, a wave at AI for
1:39
founders.co. And if this episode made you
1:41
think, made you money, or made you late to something because
1:43
you couldn't stop listening, please drop us a five star
1:46
review and tell us why. All right, Will.
1:59
Welcome to the show. Thank you so much for joining
2:01
me. Thank you so much for having me,
2:03
Ryan. It's a pleasure to.
2:05
Meet you. It is my pleasure and I'm
2:08
excited to talk to you because you know, oftentimes we we get
2:11
into the weeds and sometimes what the technical aspects of
2:14
products are, but yours, your product is one of those that you
2:17
look at at face value like I need that, you know, so begin
2:22
with kind of an overview of Workmate.
2:25
Yeah, I think that's a super like right on observation.
2:29
Sometimes we go to conferences and they're all these technical
2:32
booths out there and we have ours that just say, do you want
2:35
an executive assistant? And the non-technical audience
2:39
just comes right over and knows exactly what it is.
2:42
And they're flooded by a sea of other things that they don't
2:44
they can't even wrap their head around.
2:46
So anyway, workmate is everyone's executive assistant.
2:51
I had an executive assistant when I was lucky enough to work
2:55
at larger tech companies and get senior, and it really helped me.
2:59
And we're on a mission to democratize access to executive
3:03
assistants, to have that level of support on your calendar, on
3:07
your scheduling, so that someone, someone, something else
3:10
can take care of the busy work. And you can stay focused on what
3:14
really matters in your life and in your work.
3:18
Get some time back for focused work or a more balanced life.
3:22
And the back and forth of scheduling is something that we
3:24
take care of. Amazing.
3:27
And the scheduling, I mean, this is just music to my ears because
3:30
me personally, you know, I do probably four or five different
3:34
podcast episodes a week, you know, for, for various shows.
3:38
I, my calendar is stacked with sales calls, investor calls,
3:42
talking to the board. It's just all calls.
3:45
It's just this, this glowing rectangle that I live in all day
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long. And the scheduling can be
3:53
challenging, you know, it is part of my life.
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So I just kind of came to accept it and I basically live and die
3:59
by my calendar. If it's not on the calendar,
4:02
it's not happening, you know, and that that provides, you
4:05
know, some gaps and some some missed connections, you know, so
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talk a little bit about this scheduling agent like exactly
4:13
kind of what differentiates Workmate and kind of like how I
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could maybe me as a use case could kind of intertwine this
4:19
into podcast schedule booking, sales call booking, these kind
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of things. So Workmate, does scheduling
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like a human executive assistant would do scheduling or does
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scheduling? We modelled the AI after the
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real job from my own personal experience and talking to others
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who have done the job or been lucky enough to have the support
4:39
of an executive assistant. So it works like working with
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another human. It's not about, it's not like
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working with an app or working with a chat bot.
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It's like working with a person. They have an e-mail address, you
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can chat with them on text or on Slack or on Microsoft Teams.
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And you can do this your scheduling the way you would a
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person. If you're, if you have a certain
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preference, you just tell them what that preference is.
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If you are going to be on vacation next week or going to
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be traveling for work, you just let them know how you want to
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schedule. And so it feels very natural and
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very humid. And I think that's that's where
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we're going with AI assistance, that they'll just feel like
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another teammate. The same way that we've gotten
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so used to working with people remotely all around the world
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over the last 10 years that in 10 years from now we're going to
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be used to working with a mix of human and AI that feel like
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human. Yeah, 100%.
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So let's say. So we've got the agent in Slack.
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You know, I'm going to call, I'm going to call my agent Jim Bob,
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because there's something about a person that has two first
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names that just commands respect, you know what I mean?
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So I, I want him to feel powerful.
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So I'll come into slack. Let's say I'm doing whisper
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flow. I hit function button.
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I'm like hey Jim Bob, will you send will the pre interview
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questions we like to ask and see if we can reschedule for next
6:06
Thursday and then Jim Bob would go off and do that.
6:09
Yeah. So Jimbob, you could do that in
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Slack, you send the link and then Jimbob or your workmate
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would go out and do it. And you asked what sets us
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apart. One thing that really does set
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up, set us apart is that level of customization.
6:23
It can feel like hiring a person.
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A lot of our customers totally white label it.
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It's totally up to you, whether you, whether you call it
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Workmate or AI Scheduler or Jordan or Jill or Jimbob, and
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you can give it a e-mail address at your domain.
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And so a lot of times our customers are scheduling with
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others and they, they don't know that they're interacting with
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AI. They, they think it's a, a human
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and that's what they want. And we have other customers who
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want to be fully transparent about that.
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And that level of customization is, is what we allow for.
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That level of white labeling is what sets our solution apart
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across not only the Google ecosystem but also the Microsoft
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ecosystem. Amazing, you know, and this is
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kind of an interesting, I mean, maybe an ethical question, you
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know, with and maybe also just kind of user interface, you
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know, so if I'm interacting with a video, AII can tell
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immediately, at least of today, you know, spring 2026, you know,
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so it's like, do you need to announce it's AI?
7:22
It's like, buddy, I already know that the AI voices are getting
7:26
so good that it might fool me for a while where I'm like, ah,
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maybe you should lead with like, hey, this is a I'm AI chatbot.
7:32
You can ask me anything and you're like, OK, cool.
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That actually makes me feel like I can take more time that I can
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ask more questions. You know, people, human beings
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love them to death, but they get irritable and they they don't
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know everything. And, you know, they have
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limitations. Of course, so does AI.
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But if it's announced to me in the beginning that like this is
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an AI chat and then I'm like, OK, cool.
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I can take my time and like really kind of get into the
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nitty gritty here. If we're talking about like
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executive assistant, you know, is it important to announce that
8:03
it's AI behind the scenes or is it just like, well, you know,
8:07
it's just doing a very finite specific task, You know, what
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are your recommendations as far as disclosure?
8:14
So I think there's a big difference between the internal
8:16
and the external and what the medium of communication is.
8:19
And so internally you're chatting over Teams or Slack or
8:22
text you that our users, the people who who are part of a
8:28
team that's on workmate know that they're interacting with an
8:32
AI powered product and that one-on-one relationship, you
8:37
know, it wants to be as quick as possible immediate and they know
8:42
and you can treat it like an AI, but some of them don't want
8:45
their customers and clients to know, you know, there's a flex.
8:49
If you seem like you have an executive assistant, that's the
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flex. You know there.
8:53
We've even talked to some customers who were faking it
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before who had a separate e-mail address that they would loop in
8:57
because that's a flex. You seem more important than you
9:01
are. And we have others who just are
9:04
in older school industries where it's totally normal.
9:08
They're interacting with people who have executive assistants
9:10
all the time. They may have had an executive
9:12
assistant in the past and but then got on their own or started
9:17
their own company or the team downsized or whatever.
9:20
And they, they wanted to look at technology for that.
9:23
And so there we have many customers who are used to
9:27
dealing with an executive assistant and their, their
9:30
business relationships are also used to dealing with executive
9:33
assistants and it feels completely natural.
9:36
We've spent a lot of time making sure that those external
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communications are, are really high quality.
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They're, they're vetted, they're multiple layers of, of AI review
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and sometimes human review. And so it really can pass off as
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a, as a remote employee over e-mail.
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And that's what a lot of our customers like.
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And I think that's fine. We often have people who do it
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that way. And then with the people they're
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close with, they say, you know, that was AI and then they become
10:06
surprised and that's how they become our customer.
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But again, it's totally up to you.
10:12
We have other people who, who, you know, fall on the other side
10:16
of that ethical question and they, they just wanted to be
10:21
transparent that they want to use.
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So they call their workmate, workmate and, or AI scheduler
10:28
and they are totally transparent about it.
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And then that's what they prefer.
10:33
And it usually we now have seen enough of this that, that I know
10:38
that there's certain industries that prefer one over the other.
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There's certain demographics that prefer one over the other,
10:45
and what sets us apart is the level of customization where we
10:49
allow for both. Quick side note for founders who
10:53
are using AI to write content, you've probably noticed this.
10:57
It's incredibly fast, but it doesn't really Dr. meaningful
11:00
traffic. And honestly, that's because
11:02
most AI generated content is just average.
11:05
There's no real insight, no depth, no structure, missing
11:08
things like internal linking, and Google's getting very good
11:11
at filtering that out. So instead of trying to just
11:14
prompt better, I actually came across something interesting
11:17
called Neena. It's a system that combines
11:19
human strategy and review with AI writing to create high
11:23
quality SEO optimized blog content that's actually designed
11:27
to rank and keep ranking. What I like about it is that
11:30
it's done for me. Their team handles the topic
11:32
strategy in the content review and data markups for Google and
11:36
turns blog posts into actual long term traffic assets.
11:40
So if you're a founder thinking seriously about organic growth,
11:43
this is one of those things worth paying attention to.
11:46
You can check it out at Try neena.co.
11:48
That's TRYNIN a.co. Try neena.co Founders.
11:55
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11:58
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Oh, I love it. Yeah.
12:48
And, and that's why it's because, you know, I, I don't
12:50
know if we're there yet, but there's going to be some people
12:53
that are taking the other side of the ethical conversation and
12:56
be like, why are you discriminating against my AI
12:58
employee? It's not their fault that
13:01
they're AI. As you mentioned in the
13:03
beginning, scheduling is is we're just talking about
13:06
scheduling here. We're not talking about World
13:10
Peace or diplomacy or you know, and so, so with scheduling, you
13:18
know, there are plenty of people who have people who have virtual
13:22
assistants across the world who help them from with scheduling.
13:25
And this is not very different from that.
13:27
And I promise you a year from now, two years from now that
13:30
will it will be very normal to interact with employees who are
13:35
actually AI. For some of us, it's already
13:38
really normal, as bizarre as that is the last three months,
13:42
you know? Cool.
13:44
Yeah. And I mean I can see like a.
13:46
Three months ago I was saying next in a year or two years, but
13:49
in the last three months the the future has really arrived.
13:53
It really has it. It really has.
13:55
And it's almost like, it's like a feeling of like sinking into
14:01
the moment of like where we're are where we are because it, you
14:04
know, it's been fun to kind of prognosticate about what the
14:07
future is going to look like. But now it's really like, OK,
14:09
we've actually really arrived. It's in kind of this primitive
14:12
state. But the things we are
14:13
speculating about doing are here now, you know, so it's like, you
14:18
know, let's immerse ourself. I've been, it's been helpful for
14:22
me to think about sinking into it that way.
14:26
It doesn't feel like I did a cannonball into it and now I'm
14:29
drowning. So I, I would love to hear, you
14:32
know, kind of as a side conversation, hear kind of the
14:35
emotional feeling that you have with the speed and intensity
14:39
that's happening right now there.
14:41
There's a feeling that we talk about a lot that's feeling like
14:44
you're behind or there's a FOMO feeling.
14:47
And it's mixed with this elation of, you know, for builders and
14:51
creators, it's possibly the most fun ever, you know, So how, how
14:54
are you kind of dealing with the speed and pace?
14:58
Yeah, I think you hit the nail on it.
15:00
We're having a lot of fun. It's also challenging,
15:03
especially building a company. Now we're we're in the third
15:08
year of building this company and we've rebuilt our AI stack
15:13
several times every couple months.
15:15
There's a better way of doing it than we've been doing it before.
15:17
And if you don't, if you don't throw everything out, you're
15:22
left behind. And the, the new company that
15:25
comes along and tries to do this the latest and greatest way is
15:28
going to do it better than the way you were doing it even 612
15:31
months ago. And so you have to, for me, it's
15:36
like really fun to be able to build anything.
15:40
The the roles in a company are becoming a lot more fluid that
15:43
that I think is especially especially powerful at a small
15:48
early stage start up because anyone can do anything and you
15:52
can just get a lot more done with the same group of people.
15:56
You know, we're building a lot quicker than we could been
15:58
building than we were building in the past.
16:01
This latest time that we threw everything out and rerun it on
16:04
the latest technology happened two or three times as fast as
16:08
the previous one. At the same time, it also feels
16:11
like you're building on unstable ground and you can't really plan
16:16
for the medium term at all. You can like have a long term
16:19
strategy and vision and mission and you can have a short term
16:24
plan, but the medium term just feels that that medium range
16:27
just feels so difficult to to wrap your head around.
16:32
Yeah, yeah. There's a feeling.
16:34
I was talking to a guy developer, you know, he's
16:36
working 14-15 hours a day, you know, which kind of put him in
16:41
the hospital for about a week. Like he, he, he was overdoing it
16:45
and he comes out and he's right back at it.
16:47
And for him, he feels like the, the, the rug's going to be
16:50
pulled, that they're going to start releasing a hierarchy of
16:53
models where, you know, the, the, at a price point he won't
16:57
be able to like reach potentially.
17:00
I mean, to that, I kind of look at the landscape, there's 5 or 6
17:05
foundational models and the competition between all of them,
17:08
I think will always to be bigger, better, faster, cheaper.
17:11
So I see the trend kind of go getting running to 0, basically
17:14
where the infrastructure of AI becomes a utility.
17:17
And you know, you got a meter, you got your token maxing, but
17:20
you're never really going to, you know, finish it out.
17:23
So what's your take? Do you feel like there's a rug
17:26
pull coming? First of all, on that, on that,
17:28
what keeps you from the hospital?
17:30
You mentioned your kids before. My kids keep you from the
17:32
hospital. Like there's certain hours a day
17:34
where I just focus on that and, and you know, my, my son woke up
17:39
this morning talking about his new toy dinosaur and you just,
17:42
that keeps me grounded. It prevents me from they're
17:45
waking up at the same time every day.
17:46
So I have to go to bed or else I get no sleep and can't function
17:50
in the office. So I, I do think that there's
17:52
something to having a balanced life, even when things are going
17:57
are, are moving at this speed, You have to, you have to family
18:01
keeps you grounded and it allows you to, you know, not overdo it.
18:06
Yeah. Well, you know, and now working
18:08
in flow is more important than ever because, you know, you're
18:11
working with, let's just say, a dozen different agents and
18:15
you're, you're not, you're not in production as much as you're
18:17
managing them. And, you know, from a management
18:20
perspective, this is a big shift for a lot of people.
18:23
You know, a lot of people are used to grinding it out.
18:25
The, the part that they really like of the job was executing,
18:29
whether that's design or it's writing or whatever it is.
18:32
But now, more and more, we're shaping, as we're always say
18:35
we'll we're sculpting more than we're painting, you know, I
18:38
think. I think that's totally true.
18:41
And yeah, I don't think we're quite there at the point where
18:47
if you step away for 12 hours, you're or 8 hours to sleep or
18:53
whatever that that you're going to get the same level of
18:56
productivity from your agents that if you were if you were at
19:00
your computer checking in, being unblocked.
19:02
I think we will be there, but we haven't gotten there yet.
19:06
Like I think there's this interesting place that we're in
19:10
right now where actually being available for longer is longer
19:16
in the day actually does make your agents more productive.
19:19
And hopefully we'll get out of that to a point where like you
19:22
can go sleep the whole night and they're still going to be
19:24
productive. Like I think it was kind of in
19:28
this middle ground where sometimes you're waiting around
19:30
for them and you can like, take micro breaks 1531 hour, but
19:37
watch chest, eat lunch, whatever that kind of break.
19:40
But a whole night is the whole day off, which is what humans
19:45
really need to recharge. The agents are not fully
19:49
autonomous to be able to do that.
19:51
Yeah. So you still got to babysit them
19:54
a little bit, well, a lot of bit, but you know, it could be
19:58
detrimental like overdoing it is, you know, especially I'm
20:02
talking about flow state where I know for me if I'm, if I'm
20:06
trying to like be the arbiter of taste.
20:09
You know, like I got a whole suite of, of agents that are
20:12
going to execute for me, but it's my job to like make sure
20:15
we're going in the right direction alignment, you know,
20:18
So for me personally, that means my sleep has to be on point, my
20:21
diet has to be on point. I got to wake up and do yoga and
20:24
then during the afternoon I need to like walk, you know, because
20:28
for me, for whatever reason, when I'm just walking casually,
20:32
you know, this is where my ideas start coming.
20:35
This is where I listen to my podcast.
20:37
And so then those bursts as far as like productivity and like
20:42
opportunity are worth 100 X of just me sitting there grinding
20:46
it out on the keyboard You. Know that it kind of reminds me
20:50
in some in some way of like when I worked at Instagram and I had
20:54
152 hundred person team. So the bigger decisions were the
20:59
ones that fell on me. The taste was what fell on me.
21:03
And so you're you are flexing some management skills, but with
21:09
AI as your team rather than people as your team.
21:13
Yeah, nice. You, you brought up Instagram.
21:16
I'd love to learn a bit more about that, particularly because
21:18
I'm totally addicted to Reels. And so I just want to know what
21:22
I can blame you for, for all of my Instagram addiction.
21:27
So I spend a long time at Instagram and I'd like to talk
21:32
about it in terms of 3/3 waves. The first wave of Instagram was
21:35
the the filters on your feed. The second wave was stories, and
21:41
the third way the wave was constant content
21:43
recommendations. And I really spent years on that
21:47
third wave helping you discover the best of what was out there
21:51
on Instagram, whether it's keyword search, explore, being
21:57
much more personalized, those recommendations coming into your
22:00
feed and Reels being the big 1. So I work on the team and LED a
22:06
big part of the team that was responsible for bringing Reels
22:10
to market, the initial version of Reels as as well as growing
22:15
it to the point where now many of us have become, it's the
22:19
primary thing that we do on Instagram and love on Instagram.
22:21
And you know, making that super personalized, making it so that
22:26
that up and coming creators have a chance of breaking through.
22:30
That's something that I spent a lot of time on.
22:32
My teams were responsible for all the the content ranking
22:35
algorithms and recommendation algorithms across Instagram and
22:39
all of the the content viewing surfaces including the first
22:43
version of the Reels tab and bringing Reels into feed and
22:47
determining what shows up when across the app.
22:50
Dude, the golden era, you saw it all.
22:52
That's so cool. You know, I've actually done a
22:54
lot of work on Instagram too. Largely it's reprogramming the
22:59
algorithm so it doesn't just feed me all of the reels of
23:03
beautiful women doing squats in the gym.
23:06
You know, it was a little bit embarrassing for a while.
23:09
And I you know, if I see that video and in the beginning I was
23:12
like, God Dang, I mean, how can you, how can you scroll past it?
23:16
But then when it was like every single one was that I was like,
23:19
this is totally embarrassing. So I, you programmed it with all
23:23
the stuff that I really wanted to see, you know, which is like
23:26
fly time and jiu jitsu and 90s NFL highlights.
23:32
And I'm I'm happy to say all my hard work is paid off and my
23:36
algorithm is much more. Yeah, I'm so glad some.
23:39
Family oriented. That's something that I spent a
23:43
lot of time and attention on and really cared about it.
23:46
And we talked to people, especially men.
23:50
This was the early days of suggestions on Instagram where
23:54
where they would say, you know, my ex, I go to my explore tab
23:56
and I'm embarrassed to show my significant other, my wife,
24:01
whatever 'cause it has stuff like that that you're talking
24:04
about. And so we, we spent a lot of
24:06
time trying to, to give people more control over that and do a
24:10
better job of detecting what actually was the content in an
24:15
image rather than just the engagement signals that were
24:18
coming out of that image. And now Instagram, you know, I
24:22
haven't been there for a number of years, but large, generally
24:26
speaking, they've continued on that same trend of giving people
24:29
more and more control over what recommendations show up and
24:33
really good control. Because just like you said, all
24:36
of the people that we talked to, you say show showed us their
24:39
explore tab or their recommendations and they would
24:41
be able to say, this is what I see.
24:43
And I also, I can tell you what I love.
24:46
Help me rich gap there. Yeah, really exist where if you
24:51
are willing to put in the work, you can bridge the gap.
24:54
Yeah, totally. And not to, not to linger on
24:58
Instagram too long, but, you know, it is a fun conversation
25:01
with my wife and I because, you know, I like to see what she's
25:04
looking at or what's being served to her.
25:06
She likes to see what's being served to me.
25:08
It's just interesting. You know, it does kind of reveal
25:11
a little bit about you, but also it reveals a lot about humans,
25:15
you know, So my wife will I'll look over her shoulder and it's
25:17
always like these dudes that are like in the kitchen with a apron
25:20
in their shirt off and they have their giant have giant muscles
25:24
and they're hairless. And I'm like, what is that?
25:27
She's like, well, they're beautiful men.
25:28
I was like, no, I think that Instagram thinks you're a gay
25:31
man. Like this looks like gay cock.
25:36
She's like, well, I like it too. I'm like, all right, well, I
25:39
can't. I can't deny if I look like that
25:41
I would be cooking with my shirt off too, so I get it, you know?
25:43
What are we doing 1 of? The latest features of Instagram
25:46
that I, I love using with my wife is they call it the blend
25:50
where you can create like a shared space where your
25:55
algorithms kind of come together and you get to see and it's in
26:00
your DM. So you can start like a, an area
26:03
in your DM where you get videos that each of you kind of like,
26:08
and then your preferences start to converge.
26:12
And then sometimes now we see the same thing and then we talk
26:15
about it. And I feel like we've bonded
26:18
over the content that we see in another level.
26:20
And it makes it so that like I'm not just seeing her my stuff and
26:25
she's not just seeing her stuff and we're off in our world, but
26:28
it's more of a shared experience.
26:29
So I I recommend trying that out.
26:33
Amazing. My wife also likes those picking
26:35
videos, which I find is absolutely disgusting, but for
26:38
some reason they're incredibly popular.
26:39
So I don't want to see any of that.
26:41
None of missus artis content. Cool.
26:46
Now you know from seeing all of that, that that content coming
26:50
through Instagram. How did that kind of like, you
26:53
know, shape how you wanted the interactions with the agents
26:56
that you're building? Like how did you kind of
26:58
approach what's the personality of a workmate kind of EA?
27:05
Yeah. I mean, I spend a lot of time
27:09
building products that were entertaining, that are
27:12
entertaining and that have mass appeal.
27:15
And with Workmate, it's kind of on an on the other side of the
27:20
spectrum, we want to go for helpful and professional.
27:25
Yeah. And you know, a lot of our
27:29
customers are trusting Workmate in the middle of their important
27:33
relationships. You're in sales so that you have
27:36
a podcast. So your guests, the people who
27:39
you're trying to sell to your investors, all those people are
27:42
really important in your life. And if to put a Workmate in
27:45
between them means there's a level of trust and
27:47
professionalism that you would that you would that you expect.
27:52
And one of the biggest challenges with Workmate has
27:56
been how do you build that trust with the customer and also
28:03
deliver a consistent experience with AI at the middle so that
28:08
that trust does not get broken. And so we spend a lot of time
28:12
making sure that Workmates write the same way that they do
28:16
scheduling in a very consistent way, that they write this when
28:20
they're offering times, that they format the times and the
28:23
time zones in the same way every time.
28:26
You know, a human wouldn't would, would do it.
28:28
They would have their way and they would do it.
28:30
And so we've had to curate the workmates voice so that they do
28:35
it the same way every time and then figure out what knobs
28:38
people want to be able to control and then give them the
28:40
ability to control and customize those knobs while still
28:44
maintaining the the consistency. Yeah, we've all been kind of
28:48
trained to just like schedule on people's calendar links.
28:51
Why is work made better? It's a good question.
28:55
I think it's much better. I think scheduling on calendar
28:58
links, which by the way we support, we have unlimited free
29:01
calendar links because that's in the past, I think it's been
29:03
totally commoditized, but there is a use case for it.
29:07
Workmates better because it for a few reasons.
29:11
One, it protects your time the way you want to schedule.
29:15
If you're giving somebody else a calendar link, you're putting
29:19
the burden on them to schedule and you're letting them choose
29:24
all of your time or you have to artificially constrain your
29:27
availability. The reality of scheduling is
29:29
much more nuanced. You have times that you're
29:31
available, but you have times within those times that you
29:33
prefer. You have preferences about when
29:35
things should be scheduled, at what time of the day and what
29:38
days of the week. And so you, that's something
29:40
that you could communicate to a human and you just have to, you
29:44
have to use hard rules with calendar links.
29:48
So our system is a lot more nuanced, which means that your
29:51
time is better protected and managed rather than putting that
29:56
responsibility on, on somebody else to pick the time off your
30:00
link. The a particularly egregious
30:04
version of this that we hear is that like calendar links make
30:08
rescheduling really easy. So sometimes you'll plan your
30:10
whole day around a meeting or your whole day forms around that
30:16
meeting and then 15 minutes before and they just click that
30:19
link in the invitation and they go and reschedule them and blow
30:22
up your day. And then you end up becoming
30:24
less productive. And so sometimes like having a
30:27
workmate and having them reach out and having it not be
30:30
instantaneous is actually better to protect your time.
30:35
The the second reason, which I think is the even bigger 1, is
30:39
that workmate doesn't drop any balls.
30:42
You're never going to not get that meeting scheduled.
30:47
It always follows up. If you're sending a calendar
30:49
link, then it's on you to see whether they click that link and
30:53
it's on them to click that link with workmate.
30:56
You just CC your workmate, they offer sometimes and they'll
30:59
manage the back and forth. You can forget about it, but if
31:02
the other person doesn't respond, they'll remember and
31:05
you can still forget. And so, but the follow-ups are
31:09
huge. And I, I can't tell you how many
31:12
times I've met someone and forgot about them and then a
31:16
meeting has been on my calendar because workmate was, was
31:20
persistent and that person ended up a customer.
31:23
And so if you're in the kind of business where you're dealing
31:27
with a high volume number of people and sometimes you forget
31:31
to follow up or you have to build imperfect systems to
31:33
follow up, or you're spending a lot of time following up.
31:36
And you, your workmate will do that for you every time and get
31:40
the meeting booked. And if the, if their follow-ups
31:42
aren't working, they'll do what a human would do and message you
31:45
on the side saying, Hey, I've followed up with these with this
31:47
person three times already. Would you like to follow up?
31:50
You want to you want me to be keep keeping persistent.
31:53
And I find that I'm able to, you know, book a lot more meetings
31:59
that way. And I don't have to feel bad if
32:01
I drop the ball. Mendis Yeah, amazing couple of
32:05
functionality questions. So two of them.
32:08
One, let's say I want to personalize it where for my own
32:12
personal optimization of my day, which is to say I want to do get
32:16
that yoga and I want to get that walk in every day because that
32:19
makes me happy and that makes me better with my work.
32:23
And I can tell Jim Bob that, you know, and so basically what
32:26
he'll notice. And this is more along the the
32:28
predictive generative aspects of AI.
32:30
So I wake up, I'm working and Jim Bob's like, hey Ryan, I
32:33
noticed you didn't get to yoga this morning.
32:35
You want me to book you from 2:00 to 3:00?
32:37
There's a yoga class available for you.
32:39
Do have a 3:00 PM call, but I can push that meeting back 10
32:42
minutes for you. Would you like me to do that?
32:44
Does it have that kind of functionality?
32:47
No, if you want to have yoga everyday, you can.
32:50
You can, you can book your yoga. But I think what you did was
32:54
even something that we're working on, but is the next
32:57
level where where they can go and book a class for you on a
33:00
website for a yoga class. They'll notice that you didn't
33:04
have yoga today and you might you need to have yoga every day.
33:08
But a version of that you can do with workmate today.
33:10
You can say, hey, I want yoga every day.
33:13
Can you book me a yoga slot every day from 9:00 to 10:00 AM?
33:17
But that is movable. If you, if you need to book
33:20
something over it, feel free to book something over it and just
33:22
move my yoga to another time. And if there's no other time to
33:26
move it for that day, then then don't book over it or still book
33:30
over it. And I'll skip yoga today.
33:32
All that you can do today that I think the next step, the next
33:36
step is is being able to actually book the yoga class for
33:40
you, which which we're working on.
33:43
But we've really focused on scheduling work meetings really,
33:46
really well. So we can book a Zoom or a
33:48
Microsoft Teams for you, book on someone's booking link,
33:51
etcetera, etcetera. Cool.
33:53
What about in two weeks I'm double booked?
33:55
Will Joe Bob be like, hey, Ryan, you're you're double booked in
33:58
two weeks. You want me to reschedule with
34:00
one of them? One of them.
34:01
Yeah, that every week on Sunday you'll get an starting Sunday
34:06
night, you'll get an e-mail about the day, the next day if
34:09
you have any conflicts. And on Monday morning, your
34:12
workmate will look across the whole week and let you know what
34:14
conflicts you have. And so your conflicts are always
34:17
going to be managed for you proactively.
34:19
You won't have to do that thing where you the night before
34:24
you're like, shit, I can't go to bed right now because I I need
34:28
to clear these five conflicts on my calendar and be rude if I did
34:31
it the next day. So I got to do it now.
34:33
So many of our customers describe to us that feeling of
34:36
like needing to manage their count, clear up conflicts on
34:40
their calendar the next day or for the next week before they go
34:45
to bed. Now you don't have to worry
34:46
about that because your workmates texting you all day
34:49
long. Yeah, yeah.
34:51
You know when I say that if it's not on the calendar, doesn't
34:55
happen, that's that's real. And right now I'm feeling
34:58
stressed and pressured because I haven't scheduled like summer
35:02
trips or fall trips for the family.
35:05
And there's a lot of reasons because there's a lot of moving
35:07
parts and families, you know what I mean?
35:08
But I know I need 2 fishing trips.
35:11
I need to plan my hunting trip that coordinates with my son's
35:14
football schedule. I need to make sure that my
35:17
daughter's getting off to college.
35:18
There's all these things that have to come together that is
35:21
just like, it just takes a day to sit down and do it.
35:24
But I I haven't done it. The other thing is, for example,
35:27
I talked to my brother, he lives in Miami and he's like, hey man,
35:30
let's, let's, let's, let's get a trip together.
35:32
I want to come into Colorado. I'm like, OK, actually let's do
35:35
the weekend after the 4th of July because you know, all the
35:38
mouth breathers will be out of the hills and we can get up
35:40
there and do our thing. Now what I would love to be able
35:43
to do is say, Hey, Joe, Bob, the Thursday and Friday after 4th of
35:47
July, clear my schedule. Also clear the Thursday and
35:52
Friday before every national holiday until 2027 and then send
35:56
me updates to to schedule family trips on those dates.
36:00
You know, is that functionality available?
36:03
Yeah, you can. You can do that.
36:04
You know, if you wake up in the morning and you're sick or you
36:07
need to go on a last minute business trip or you want to
36:09
plan ahead for holidays or vacations, just send a message
36:12
saying, hey, I need to rebook all my meetings on this day,
36:15
clear my calendar and then your workmate will reach out to every
36:17
single one of them and reschedule it.
36:19
If you have a trip, you can say, hey, I'm going to be travelling
36:22
on this day. Only book in person meetings in
36:24
this place and no remote meetings.
36:27
Just you, you do it the same way a person would you just if you
36:30
had a person working for you, they could be able to do that.
36:33
They would be able to do that. And this is the same.
36:36
Yeah, You know, it's, it's interesting because the idea is
36:40
face value is so easy to get. Oh, it'll schedule your meetings
36:42
for you. You're like, great.
36:43
But really this is almost like lifestyle management, you know,
36:46
where it's like, OK, now I, I, I can be more intentional with my
36:50
time because if I'm not, I'm going to work, you know, 8:00 to
36:54
8:00 every single day, six days a week, you know, because I'll
36:58
just start scheduling it out, you know, But if you can set
37:00
parameters for yourself, you can set, you know, just by talking
37:04
to it to be like, hey, these are what's important to me.
37:06
These are the dates. Like make sure all this stuff is
37:08
happening and it just happens. It goes to the calendar, which
37:11
frees your time, which, oh, I mean freeze, but also freezes
37:14
your time. So then you, you can take the
37:17
steps necessary. I think it's brilliant.
37:18
I love it. Let's talk about pricing a
37:20
little bit 'cause I noticed there isn't any pricing on the,
37:23
the, the website. Is that intentional?
37:27
Yeah, our focus right now has been on like trying to Bing
37:31
bring on bigger and bigger companies.
37:32
And so, yeah, we try to be very white glove about what the needs
37:35
are, what the volume is going to be and then figure out the
37:38
pricing. But if it's if it's just an
37:40
individual or someone getting on, then we have very reasonable
37:44
pricing that's very competitive and and and you know, very
37:50
affordable. It's it's way lower than the
37:52
cost of a person. Yeah, 100%.
37:56
So you know and talk about the difference there because I see
37:59
this is a very personal kind of asset as opposed to like maybe
38:04
an enterprise add on. So when you're looking for
38:06
multiple seats, I mean that's obviously for a business model
38:10
that makes a lot more sense because the revenue is larger.
38:12
But it how do you is it more successful selling in with
38:18
multiple agents, multiple seats, multiple people than going for
38:22
like individuals? We have the range of customers.
38:26
We have teams that where they bring their whole team on, they
38:30
start with a pilot maybe of just the executives.
38:33
We have people who already have executive assistants on those
38:36
teams and they just those executive assistants want to
38:38
spend less time scheduling because they have a lot of other
38:41
things to do. And so, you know, one of the
38:43
biggest surprises that we have a lot of teams where the executive
38:46
assistant is also a user of Workmate and we've built
38:48
specific tools for them. And then on the other side of
38:52
the spectrum, we have the the people who are solopreneurs,
38:56
founders, you know, consultants who are running their own
38:59
businesses who find this useful. And so, you know, our sales
39:04
motion is much more geared towards the former, but anyone
39:07
can come in and try it for free. And if you're just a one person
39:10
team, you're going to be paying a pretty reasonable price when
39:14
comparing to the time that you're going to save.
39:17
And also there are other options out there which would be hiring
39:22
someone either locally or anywhere in the world to help
39:26
you. Well, and I have 3 Google
39:30
calendars that I maintain. It's a hellish landscape.
39:35
Can you? Can Jim Bob handle three
39:37
different calendars? Of course, of course, like
39:39
that's, that's no problem. You can connect 3 calendars.
39:43
You can, you know, we, you can for free connect 2 calendars and
39:48
schedule a couple meetings a month without paying anything.
39:52
And yeah, we, we do that very, very easily.
39:57
We have people who are scheduling meetings across all
40:00
time zones. You know, humans find.
40:03
Time zone conversion. Hellish AI doesn't bat an eye.
40:08
Shout out to my people in Singapore and Dubai.
40:11
I tell you, for the mountain Standard Time zone, it is the
40:13
worst. I just like, oh, man, I I am
40:17
loathe to make you stay up till 10:00 PM to talk to me, but I'm
40:21
not taking a call before 9:00 AM I'm sorry.
40:24
Yeah. Yeah, and also the conversion,
40:26
they're probably just sitting there Googling it.
40:28
And if they're trying to, if you're trying to schedule a big
40:30
work meeting, you're looking at that terrible view and outlook
40:33
where you see all everybody snakes across different time
40:36
zones and it's, it's hard, but workmate doesn't bat nigh at
40:42
that. So you just chat.
40:43
You get rid of all that and just chat.
40:46
Amazing. All right, we'll, we're ready to
40:48
enter the quantum round. Are you ready for this?
40:52
Is that going to be fast? Let's do it.
40:54
Ish, it's pretty fast. OK, aside from Workmate, what
40:58
experiments are toys or what are you building with AI?
41:03
We've been experimenting a lot with open claw and other similar
41:07
things to try to automate our processes and also try to to
41:11
make workmate more versatile and flexible and be able to do
41:15
things beyond scheduling. And it it's been really awesome.
41:18
Like, you know, I have the open claw running on my, on my
41:23
compute, my Mac mini doing a lot of things.
41:25
We now have it in the cloud. I've, our team has several open
41:28
claws in the cloud doing things and we've been having a lot of
41:32
fun with that. So much fun that we're planning
41:35
on incorporating it into our product.
41:38
What's the most valuable thing that you're doing with Open Claw
41:40
right now? We're managing all of our paid
41:44
advertising through Open Claw. We used to and to some extent
41:52
still do for now pay some agencies to manage and experts
41:57
to manage our ads, but open clause just as good at them and
42:00
is optimizing 24/7. And I think the next level that
42:05
we're trying to get it to is to not just optimize our current
42:08
creatives, but generate a lot more new creatives and be
42:11
constantly experimenting at a rate that's like superhuman.
42:16
So it's creating, it's creating the the the content and the
42:20
creative. It's deploying it, it's
42:22
measuring success and publishing and unpublishing accordingly.
42:26
Do you feel like it's it does better than Meta's Facebook Ad
42:30
Manager? I yeah, on the meta side and
42:34
especially on the Google side, the the management of it and the
42:38
analysis of it is definitely better.
42:40
The creative side I, I don't think we've like quite fully
42:44
cracked that loop. Like you, you can kind of tell
42:47
when it's slop for an AI versus real.
42:50
And sometimes those perform better still and it surprises
42:53
me. But but, but generally speaking,
42:59
the creative that I feel most proud of is the one that our
43:02
team makes still. It's frustrating though, right
43:05
I'll do the same thing I'll work for two hours on a video, be
43:08
like all right and I publish it it gets 10 views and then I'll
43:12
like just kind of take a quick take from the podcast over up
43:15
there 50,000 views. I'm like, man, that's not fair.
43:23
I think the. Next step is pretty awesome.
43:25
Like we're, we're, we're working on a on a video for a new
43:28
product launch and our team is using AI entirely to generate
43:36
the visuals of the video, but we're still editing it pretty
43:39
heavily manually. And it's some we're creating
43:43
something that both feels really high quality and is the kind of
43:47
thing that you could never create without AI.
43:52
Do you have a life motto or a framework that sticks out as a
43:56
founder and a leader as they're kind of like a a, a skeletal
44:01
praise that gets you motivated? That's a good question.
44:08
It was something that I learned
44:19
very, very young. I used to be the type of person
44:23
who who wanted to get everything my way, didn't pick my battles.
44:29
And now I, I've learned to pick my battles to, you know, what's
44:34
important and what's not important and, you know, focus
44:38
on the things that Matt focus on what matters in life and work.
44:42
And sometimes the perfect is the enemy of the good.
44:47
Yeah, seems more relevant now than ever.
44:50
You know, with all the opportunity, it's almost like
44:52
what you're not doing is more important than what you are
44:55
doing. Yeah, and sometimes getting, you
45:00
know, if you don't focus on being on doing everything
45:02
perfectly, then you can get 10X more done because the the
45:06
difference between 90% and 100% is, is a lot of time.
45:10
You know, they, it always, I think the, the expression that
45:14
the last 20% is the is 80% of the time or whatever it is, is,
45:18
is actually correct sometimes. And so, you know, often times it
45:22
really matters to get to 100% and to focus on the last 20%,
45:26
but but you can get way more done if you don't.
45:28
And so I think now, even in this AI world where that last 20%
45:32
sometimes still falls on the human to do, you have to know
45:36
when it really matters and when it doesn't.
45:39
Percent. Well, I got a boogie.
45:41
This has been such an awesome conversation to kind of wrap
45:44
things up. I know care-international.org is
45:47
important to you. Tell us a little bit about the
45:49
that that company or I'm sorry, non profit.
45:53
Yeah, I have some friends who were really involved in this, in
45:57
this nonprofit and they're they're, they've been around for
46:01
decades and they do great work to to save lives and defeat
46:06
poverty all around the world. And I know people who have gone
46:11
on trips with them and delivered packages all around the world to
46:17
to help people pretty profoundly.
46:19
And I think it's just a great 'cause So I I'm happy to support
46:24
it and I am happy that if your audience supports it as well.
46:30
Credible Care works to help save lives and defeat poverty across
46:34
the globe. care-international.org of
46:37
course. workmate.com is where you can find Workmate.
46:41
How much did you pay for that domain it?
46:45
Wasn't that much. We, we've spent, we spent a
46:51
good, you know, a small amount on domains, but it was less than
46:56
you would think. And we have a good domain broker
46:59
if you need it. More than 10,000.
47:02
Yeah, more than 10,000 but but not that much more.
47:05
Cool, amazing, great domain. 58 letters, 8 letters.
47:09
It's nice. Wills.
47:11
Where is the best place for people to connect with you
47:13
personally online? LinkedIn e-mail, Feel free to
47:18
reach out will at workmate.com and yeah, LinkedIn is also a
47:24
great place. And if you want to try out
47:25
Workmate, just go to our website.
47:27
We have a two week free trial you can get started.
47:30
And if happy to hook up, hook up any of your listeners with an
47:35
extended trial if they reach out to me.
47:37
Tremendous. I know I'm going to do it.
47:39
Definitely go check out the free trial of Workmate.
47:41
It looks so cool. I'm really excited about it.
47:45
Talking about schedule and calendar, I didn't realize how
47:48
much I needed to do that, so will I appreciate that.
47:51
All the links will be in the show notes, so definitely check
47:54
that out. You bet.
47:55
We got to get you hooked up extended free, extra free trial
47:58
for you. I really enjoyed it.
47:59
So, OK, really would love to you get it exactly.
48:03
Would love to get you on board. I'm signing.
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