Beyond the Prompt, "Rebuilding from Inside: How John Waldmann Led an AI Shift Without Breaking His Team" (June 10, 2025), episode transcript

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Transcript of episode E41 of the podcast Beyond the Prompt, "Rebuilding from Inside: How John Waldmann Led an AI Shift Without Breaking His Team," dated June 10, 2025, with a running time of 52:29. Jeremy Utley and Henrik Werdelin talk with John Waldmann, who introduces himself as founder and CEO of Homebase, a team management platform for local businesses. Waldmann says Homebase serves over 150,000 local businesses and over 2 million workers and has spent the last year reinventing itself as an AI first company. The conversation covers rapid prototyping, getting closer to customers and how the company is changing the way it builds product.

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“Beyond the Prompt, ‘Rebuilding from Inside: How John Waldmann Led an AI Shift Without Breaking His Team’ (June 10, 2025), episode transcript.” Original at podcast.beyondtheprompt.ai. Archived at Pandemic Darlings, https://pandemicdarlings.com/source-documents/beyond-the-prompt-rebuilding-from-inside-how-john-waldmann-led-an-ai-s-613adfdbab/, SHA-256 64b670228bdb116477eeb0000fd3455a2043137f6ff90149fb310ad2d01625db.

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00:00 52:29

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Rebuilding from Inside: How
John Waldmann Led an AI
Shift Without Breaking His
Team
JUNE 10TH, 2025 | 52:29 | E41

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[00:00:00] belowWaldmann:
to learn more about
I talked tothese cookies:
her about what we wanna do
from an AI standpoint. I'm like, right out of the gate, I'm like, I wanna
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talk to you about ai. And her initial response was, I hate ai. I hate the
companies building with AI companies, building with ai, don't care
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about humans. And it was like a fundamental, Cookies
was like, I'm
coming from a place of living in hospitality.
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Everything I do is about the human interaction. Putting an
00:00 52:29
extraordinary amount of weight and pride on that. And that was like
a very impactful thing. But I'll tell you by the end of the conversation,
it was a. When can I get access to what you're building? Hi, I'm John
Waldman. I am the founder and CEO of Homebase.

We are the leading team management platform for local
businesses, serving over 150,000 of your favorite local businesses
and over 2 million workers. Uh, we have spent the last year
reinventing ourselves as an AI first company.

[00:00:52] Jeremy Utley: Wonderful. Well, maybe one thing that I've
really been excited to talk to you about, John, is I know when we
reconnected recently, it was because you had posted on LinkedIn
about how you are reinventing the business from the ground up with
ai.

And so I thought it could be fun just to kinda hear you talk, maybe
first home base historically, and then what has changed for you as
you've thought about rebuilding the business.

[00:01:19] John Waldmann: Yeah. Um, it's, that's a big topic. Uh,
'cause I think right in this moment of time, it cuts across everything.
What are we building?

How are we building it the way that we operate as a company so we
can talk about any and all of that. Um,

[00:01:31] Jeremy Utley: okay. Uh, well, I like, I like even those, that
distinction, right? The what and the how. What are we building?
Yeah. How are we working and how are we, maybe let's start with
the how, because I think that's probably more essential to the DNA,
so to speak.
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And then let's get to the what after that.
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[00:01:46]
security. Click John Waldmann:
below to I would
learn more aboutsay, you know,
these the, what, what
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are we building is an evolution. And, and that part has been very
consistent over the 10 year life of our company. And what I think
about for, uh, forward, you know, the North Star there doesn't really
change, but I think the, how we build is changing so dramatically.

And you, Jeremy, when I reached out to you, I was sharing some of
the thoughts that I was having of like, wow. Uh, at this moment in
time, I feel like I'm going back to D School. Type building and kind of
00:00 52:29
foundational founder mode, thinking about product and how to build
product, uh, as much as I have in the last 10 years.

And it was super exciting and fun in that moment. And I think what
I. I'll just, I'll, I'll take the way that we build product as an example
from like a product and design standpoint. I think getting to the part
of like, okay, we're back into the rapid prototyping, working closely
with design partners, the pace of iteration and learning, you know,
all that stuff has been radically accelerated in the ways that we're
building any product.

Uh, and that's been, that's been one of a hundred ways in which we
are, are changing how we work to kind of meet the moment.

[00:02:56] Jeremy Utley: When you talk about getting closer to the
customer and the speed at which you're prototyping, what's
enabling that?

[00:03:03] John Waldmann: Yeah, so getting closer to the
customers, you know, I think that's something that we've always
been super pride of ourself on.

You know, we serve local businesses, we serve a lot of local
businesses. They're an incredibly fun customer to serve, right? You
can go walk into and talk to him live. Their problems are so tangible,
their stories are incredible. They're the best possible customer that
you could hope for. You get to a certain level of scale though, and
like some of those interactions become a little bit abstracted.

You know, you, you've got 150,000 plus customers. You can launch
a, a feature in the product, and you get hard data back pretty quickly.
On, uh, how are people responding? Did the AV test hold, did it drive
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You know, we've got 4 million plus people we'll use home base this
year, but you can get incredible amounts of data from that. I think
the thing that gets lost in that is like, we're in a moment where we're
trying to create magic, and like that has, that's a little bit more
qualitative than, you know, how did it perform on the AB test?
And for that, it's like the, okay, let me take a prototype early in how
00:00 52:29
we're thinking about something, put it in front of you in person and
see like, what are you reacting to? You know, the, the most basic,
take it back to the roots of building product and design. Like take it
back, see what the reaction is.

Come back a week later with a slightly different version of it, like a
slightly more expanded version and just like keep pulling on that,
that thread. And I think the, the great enabler here is all of these new
prototyping tools. You know, we, we are now probably, uh, pumping
out prototypes on bolt new or lovable, uh, or so, like all of these
things have to be some co so core to the way that we do product
and design at home base.

Uh, and has really changed the way that we're able to interact with
customers and each other

[00:04:55] Jeremy Utley: well. Well, let's, one thing that's fascinating
here, John, and I love that you went this direction, is I think when
folks who maybe aren't so familiar with collaboration with ai,
leveraging AI tools, when they think of AI conceptually, they think it's
gonna get you farther away from the customer, and it's going to put
you more towards abstracted AB test.

But what you just said is, now that we're using prototyping tools.
We're getting back in front of people more quickly. More rapidly,
which I think is a very counterintuitive impact. Right. So what's
changed there or why has that led to more in-person almost, you
could say analog interaction.

[00:05:32] John Waldmann: Yeah. I, i, it, it, it totally is that analog
interaction.
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Uh. I think part of it is the, the pace of development and learning.
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You, Jim, I go back to like, one of my favorite frameworks from the
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framework and, and like, are you moving a prototype? Are you
moving a learning or a product on both of those dimensions?

And those two dimensions are. Correlated, but they're not the same
thing. And I think in this moment where, uh, you can be behind the
engines working on prompts and working on kind of how the AI is
interacting, what's possible there at the same time where you're
rapidly prototyping on what is the front end of this thing, how is this
00:00 52:29
gonna show up for users?

What, what are the ways that people want to interact with that? I
think you just get such a faster pace of learning on that. Versus,
Hey, let's build Figma prototypes that are so high resolution on the,
what does it look like, but are maybe not giving you the same cycle
times on just the customer feedback.

[00:06:34] Henrik Werdelin: Do you take a bolt kind of like, uh,
prototype or lovable or replicate or whatever and you throw it
straight to the customer? Or is that like, is that more for testing?
Like do you throw it in production already?

[00:06:47] John Waldmann: So we've done all, all sorts of things.
Like this is the thing we're evolving through in real time.

Uh, yeah. I sat through a, a roadmap review meeting last week
where it was every single item on the roadmap had a lovable
prototype attached to it. And so instead of talking about like
concepts or, or designs or anything like that, it was, let's talk about,
let's just go through all of the prototypes and spend two minutes on
each of these prototypes.

And these were like out there ideas, right? It allowed us to kind of
like pressure test of thinking.

[00:07:17] Henrik Werdelin: It's the whole of if a picture is worth a
thousand, a thousand words, then like a prototype is where it's a
thousand pictures, right? Yeah.

[00:07:23] John Waldmann: I I think it was like the joke is true, right?
Of like nobody sat here and was like a 20 page PRD doc is the best
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the prototype and everybody can kind of click on the idea super
fast. Uh, so and that's and that,

[00:07:41] Jeremy Utley: sorry, just to be sure. Yeah, just, just to
make sure I understand, John, you're saying that's where we were
prior to unleashing our product and development teams with ai, we
had kind of devolved, you could say, even though you started by the
00:00 52:29
way, such a wonderful place.

But you kind of evolved to the point that the way we communicate
with each other is 20 page PR docs. I can imagine even the
bandwidth required for a human understanding to get up to speed. I
can't get in the field. I got all these PR docs I gotta read. Right,
exactly.

[00:08:09] John Waldmann: Like, you know, and you think about just
like for me as a CEO, then sitting there and being like, well, shit, to
stay current on what we might build that, that requires so much
reading and.

The process had become incredibly linear. You know, we pride
ourselves in like our cultural value is oh, day wasted. That's one of
our three cultural values. And yet, like we had fallen into the trap of
very linear kind of product building, very stepwise product building
in a way that was leading to these very, very heavy artifacts that
were great and served a purpose.

Don't get me wrong, like we got there for a reason, but at the same
time was leading to very slow cycle times on feedback. And leading
to very big checkpoints for us getting customer feedback. And I
think the thing that this has allowed us to do is just blow that up, uh,
and allow anybody to kind of go out and get feedback in a new way.

[00:09:03] Henrik Werdelin: I think as an entrepreneur, obviously
you're, the people that you serve are incredible fascinating because
to your point, like these are these incredible people who. Maybe
don't get like the glory and the fast company articles, but like they
are the one who keep the economy alive and the American dream
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[00:09:24] John Waldmann: That, that is a, a good question. I think
it's a wide range. In two years ago, um, I was doing just like a
random zoom catch up with six customers at the time. And I
remember at that time being blown away of like, oh, these, these
businesses have moved away faster here.

Than I thought. Uh, and I, I would remember, uh, there's this
incredible business, Brooklyn Tea, uh, great tea shop in Brooklyn.
Uh, and I remember her telling story super early on. She, she has a
00:00 52:29
e-commerce site that she runs too. And she was talking about
spending the weekend, uh, using chat GPT to generate a bunch of
descriptions for all of the tees that she was gonna like put on her
her website and how long that would've taken her before.

Honestly that was probably like May of 2023. It was relatively early
on, maybe even earlier March of 2023, and she had like found a very
specific use case in it. Now I think of like there, there is still a
technical gate to like really unlock the power of AI and to push really
hard on some of these applications and use cases for which that's
very, very hard for a small business owner.

That's, that's where we come in, right? Is how are we bringing AI at
scale to make building and managing a team incredibly easy so that
you don't have to think about all of the minutiae and tasks that
come with it. Uh, and I think there, there, there is an interesting
dichotomy. You know, I, I always remember the, the conversation
with, uh.

A friend who, uh, ran restaurants very plugged into kind of
hospitality scene broadly, and, and I, I talked to her about what we
wanna do from an AI standpoint. I'm like, right out of the gate, I'm
like, I wanna talk to you about ai. And her initial response was, I hate
ai. I hate the companies building with AI companies, building with
ai.

I don't care about humans. And it was like a fundamental, it was like,
I'm coming from a place of living in hospitality. Everything I do is
about the human interaction. Putting an extraordinary amount of
weight and pride on that. And that was like a very impactful thing.
But I'll tell you by the end of the conversation, it was a, oh, when can
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are you handling no shows today? Like, do you really need to spend
your time on that? Or is that a thing that AI could do for you?

Do you really need to be screening the hundred cashier resumes
that you got in the past week? Could AI do that for you? You know,
you bring it to these very tactical applications, it's like, oh shit. I
would love the help actually. Like I spent hours on that and I hate it.
00:00 52:29
Uh, but you know, just

[00:12:13] Jeremy Utley: connect from, I hate AI to these hated or
dreaded workflows.

You go, oh, I didn't know it could do that. Right? Yeah.

[00:12:21] John Waldmann: Yeah. And so I think that's a little bit
back to our, our. Job as product builders is to like bring it back to
the real problems that they're dealing with every day and not make it
some like philosophical, uh, technology. Some grand debate around,
uh, technology and back to like the, hey, we can make your life
easier.

[00:12:40] Jeremy Utley: Could we go back to that conversation?
'cause I think that's actually kind of a really cool use case. So you're
talking to this hospitality leader who's really, I'm sure, uh, prides
herself probably in this kind of handcrafted artisanal care right in, in
the hospitality space. I'm familiar with some of those folks.

Um, she starts the conversation by saying, I hate ai. What? Is your
approach, I mean, 'cause you're not like an AI evangelist, it's not like
you're trying to sell her on ai, but what was the conversation like that
moved her in? It seems like relatively short order from, I hate AI to
When can I sign up?

[00:13:16] John Waldmann: Yeah. I think, um, moving is, is like the
most trite answer imaginable, but moving it from the technology to
the problem, right?

Which
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home back homebased at X, uh, and getting those like, oh, that's
possible moments.

So bringing it back to the things that she's actually dealing with, the
things that she's seen firsthand as opposed to the let's lead with the
technology. But I think that's always true.
[00:13:59] Henrik Werdelin: I have a weird question that's kind of like
00:00 52:29
popping up in my brain. Um, I was talking to somebody else who
was kind of talking about the demise of SaaS.

Um, and of course you're doing many like a SaaS product for
specific customers. Where do you think the companies like yourself,
and I definitely have like a, you know, like a, maybe a suggestion,
um, where do you sit in the question of how concerned you should
be? That a chat GBT becomes so powerful that the uh, yeah.

That the features that you provide are kind of like, uh, just
something that people will just do on that app.

[00:14:40] John Waldmann: Listen, I, I'll be the first person to say, I
think SaaS is dead. Uh, I said it in, you know, we had our leadership
offsite in May of 2023, and I sat there and like the theme of the
presentation was.

The age of SaaS is over. Uh, here's how we have to think about our
company going forward. Uh, I totally believe that. I think at the end
of the day, if what you are doing is, uh, if, if your advantage is the
code base that you had built up over however much time the size of
your code base, the surface area of your product.

You are in a bad position, uh, because it's pretty obvious that AI
tools are gonna be really good at writing code and therefore the
barrier to entry of just building product is going down incredibly
fast. Uh, that the moat of a code base is pretty much done and that
the relative ease of expanding our product and things like that is
going to.

Come down dramatically. That's true. Before you even get to the,
Hey, what is the role of agents in the future? Just like fundamentally
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over.

Uh, now if you abstract away from what software is and then he, can
you tell me what your, what your solution here is? Uh, I, I think if you
extract away from what software is, it's like, well, fundamentally this
is about helping a specific type of user make their life easier. And if
you can totally transform that from like, Hey, let's make that work
easier by bringing it online, designing some relatively easy
00:00 52:29
workflows and building some automations into that to like, Hey, let's
use tools to just do the work for you.

You are a profoundly more valuable company to your customers,
and that customer hasn't changed. You have just evolved the way
that you serve them. And I think that is the jump that every software
company needs to make. I don't think every software company is in
a great position to do it, but, uh, I believe that we are.

Uh, so that's gonna be our focus.

[00:16:50] Henrik Werdelin: Yeah, I think, I mean, like, I think you are
too, which is why I dared asking the question. Uh. I'm biased. I have
a book coming out on the subject, uh, August 5th called me My
Customer in ai. And the thesis is basically that entrepreneurship is
gonna be much easier. So you're gonna see more types of
entrepreneurs to companies are going to look different, right?

So the object that is a company is changed. And, and then thirdly,
when now more and more people can do it. How do you stand out?
And we talk a lot in the book about this thing we call relationship
capital, which is, you know, how do you create the authenticity and
the authority? To understand a customer so well that you can be
predicting what are kind of like the problems that we can solve with
technology, and then exactly what you're doing, kind of bundle that
up because at the end of the day, it requires real cognitive kind of
resources to figure out how do you take this specific problem that is
in the real world, and then how do you apply an LM model to it?

And another event is that I think you will have is that. While it's not a
network effect, there's network in this effect in that when you serve
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[00:18:12] John Waldmann: I, I a hundred percent agree with that.
And one, like I, I listened to the autos, uh. Uh, interview you all did.
And you know, I absolutely believe in the thesis around what AI
unlocks for entrepreneurship and how great that is going to be for
the world. Totally believe in that. Uh, and two absolutely believe that
so much of the long-term value of a company is ultimately in the
00:00 52:29
customer focus and the understanding of a customer.

And I think one of the underrated powers of AI is that it allow,
including reducing the cost of building software. That it allows for
verticalization and purpose-built software in a way that it never
existed before. And that was true whether you're building software,
but I think, or AI agents. But I think it's doubly true going forward.

And I think like, you know, you still end up with these massive
pockets of the software economy that are completely horizontal.
Serving wildly different types of business and users with subpar
solutions for all of them. And I, I think that is a thing that we should
all be optimistic for, kind of the flywheel accelerating on of giving
more purpose-built solutions.

[00:19:23] Jeremy Utley: I, I love, you had said a second ago, John,
not every company is positioned to make this shift, but we are, you
know, from, call it your advantage being your code base to your
advantage being your customer. Can you talk about. How you,
'cause now it sounds like you've been undergoing this
transformation for, call it the last year.

What were some of the key early moves you had to make as a CEO
to shift your kind of company mindset? From our, the basis of our
advantage is blank to the basis of our advantage is this other thing.

[00:19:53] John Waldmann: So I think, uh, I can sit here and say this,
you know, give change is really hard. Uh, I sit here and say, if like.

We were so far ahead in our thinking of this in May of 2023, we're
talking about the end of SaaS. I gave that presentation we talked
about as a leadership group. Guess what? A year later, nothing had
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Uh, I took a very bottoms up approach of like, Hey, what's. Let's
communicate a vision for where we want to go. But I'm such a, I
was a big believer of like, this changes everything. This is gonna
change every part of our product. It's gonna change every part of
how we work. Let's push this out to the entire company
immediately.
Wrong strategy in a moment of change. Uh, looking backwards, I
00:00 52:29
think where we really started accelerating in that change and
getting the, the flywheel going was actually when we started to be
more directive on it. And that, that was, I don't know, nine months
later, uh. Coming out and saying of like, okay, actually we're gonna
pick some very centralized teams and we are going to, uh, use them
to prototype in different ways, whether that's internal operations or
the products we're building.

We are gonna take the people that we have seen the natural
curiosity for around these tools, and we are gonna elevate them to
different positions where that curiosity and kind of experimentation
can spread throughout the organization. We were going to
recognize that and reward that more publicly in the things that we're
doing from a show and tell standpoint, from a team learning
standpoint.

And then ultimately just being far more directive on you have to use
these tools, you have to change the way that you work. And
ultimately of like, this is what the roadmap is. And I'll tell you as a
part of that, I took over product again. Uh, so, you know, I hadn't
been running product, but I took it over about a year ago for that
reason was like, we gotta be more directive.

[00:21:48] Henrik Werdelin: I think it's. Incredible important point you
are making and, and I think a lot of the companies I'm involved in,
we've seen exactly the same, where there's kind of like been this
invitation to start with from the founders often and then, you know,
like business as usual, uh, because you know, people don't like to
change that much.

And I also thinking like a lot of people who kind of had worked
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people the same that you're saying is that we had to kind of do that.

Um, Jeremy and I was talking just before you got on, um, on
something that Kevin Kelly was talking about in an earlier podcast
Yeah. Where he was comparing artificial intelligence with artificial
power, and then he was talking about how you couldn't just apply
artificial power to kinda like the. The wagons that you had, you
know, that used this hols with, and so you, you had to kind of rebuild
00:00 52:29
stuff from the ground up on that stack.

You had to build factories. And with autonomous driving, you
probably can't use exactly the same roads and signs. Suddenly you
have to rebuild stuff. And so what I hear you say is in many ways
the same, that if you want to take full advantage of ai. You kind of
have to kind of almost rebuild on a quote unquote AI stack, not
technology stack, but kinda like technology acceptance stack.

Is that, is that what I hear you say? A

[00:23:21] John Waldmann: hundred percent. A hundred percent.
And I, I, I do think, um, I. That most people will get to an oh shit
moment using these tools and realize how powerful they are, and
then kind of the natural curiosity can kind of emerge around it. But I,
I do think at an individual level for change, you, you kind of have to
get people, help people get to that oh shit moment, and then give a
lot of the tooling to your point and infrastructure and change and be
directive of how different the world is gonna be in a, in a post world
share.

Um. One of our board members said something really profound, uh,
probably a year ago, uh, when he was talking about trying to get the
company up the, up this learning curve, and he said is if you want to
get people who are, uh, further ahead on thinking about ai, hire
some people that are unemployed right now as point was one.

They're the people who have the time to tinker. They're not day to
day in the, uh,

[00:24:28] Jeremy Utley: they're not steeped in the status quo.

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They're not busy writing PRD docs. Uh, but the other part of it is
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have a skill set here.

And that's in a very important thing. And I think if you are a leader in
this moment and you care about your team, you care about the
people working for you, you're doing a huge disservice to them if
you don't kind of push them into the deep end of the pool and nudge
them to learn these, these tasks, I, I think there's a lot of people that
are kind of doing it by invitation and suggestion, but at some point
it's like, yeah, I just feel like I would be doing the team a disservice
00:00 52:29
like.

This is where the world is going. And if they're not developing the
toolkit here, we have not served them. Uh, we should be the place
where you can get up that.

[00:25:12] Jeremy Utley: How specifically. So say somebody
accepts that premise, John, and they, and they hear you say, I wrote
this down. I'm, I'm taking diligent notes here.

You're doing a disservice to employees who aren't up the curve if
you don't push them into the deep end. If a leader accepts that
premise and they say, well, where do I push? How do I push? What
are the kind of levers that you use to push people?

[00:25:37] John Waldmann: Well, so there's a lot of, I think things
that are not gonna surprise here.

It was things like lunch and learns and trainings. It was.
Hackathons. But I'll tell you the thing that made all the difference in
the world. We did two hackathons, uh, six months, maybe nine
months apart. First Hackathon was like, Hey, we highly encourage
you to use ai. Second hackathon was you have to use an AI tool.

Like that is the theme of the hackathon. And we do company-wide
hackathons. So it's not just engineering. A product design is
company-wide. Uh, guess which one was more impactful for the
change management? Right. It was like, I can get people over that
inertia a little bit of the, the fear and all of that.

'cause everybody's got like, well I got all these other ideas that I'm
really excited for. And they're not bad ideas. They're always great
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natural curiosity and were tinkering on it and getting them kind of
within those teams, sharing what they're doing and building the
agents and showing how they can build prototypes.

Uh, and kind of leveraging some of those, uh, bottoms up examples,
well tops down stuff of like, you know, take cogen of like, you will
use a cogen tool, uh, and going from like, Hey, this is like an optional
thing for you to, Hey, we, we expect you to use this as a part of your
workflow. Uh, so I, I do think some of it is back to, you know, being a
00:00 52:29
little bit more directive.

In some of this. And then frankly, it's a lot of the commitment of like
bringing the tools in. Uh, yeah. Making the investment of third party
tools as well.

[00:27:14] Jeremy Utley: Yeah. And then how you integrate, 'cause I
wanna circle back to your board member's comment. I think it's so
profound and so astute. The comment that higher people who are
unemployed right now, I.

One of our favorite, one of the, one of probably the most popular
episodes of this show to date is A CMO named Russ Summers, who
was a, is a very pragmatic episode about how he basically
unleashed what he calls a GP team to do the entire marketing
function of his new company. And we get deep into the
conversation, we go, Russ, where did your knowledge come from?

And you know what he said, I was laid off. That's so funny, right? I
mean, yeah, and he basically had, and, and I think one thing there,
there's two really important aspects to what you're saying. One,
somebody who doesn't have a job actually has time to invest,
whereas somebody who has a job has plausible deniability.

Like, when am I supposed to learn this stuff? Yeah. I'm shipping
PRD docs. You want me to stop writing PRD docs, right? It's like this
weird chicken and egg problem. The other thing is that, that I think
is really profound that you said is this person, say Russ or the
unemployed that you're hiring, this person knows it's unacceptable.

They're no longer fit for the new world, and they are approaching
their season of unemployment probably differently. So my, so Juan,
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how did you integrate them into an environment where you got a
bunch of folks who are, may, you know, some varying degrees have
caught up with the status quo?

[00:28:46] John Waldmann: Yeah, I mean, I'm running, I'm running
product right now, so I see it a lot on those front lines. You know,
I'm, I'm interviewing the PMs coming through as we, as we hire, uh,
and. I think is in, in the context of an interview and, and talking to
00:00 52:29
candidates first, you can see who's curious, who's been exploring
the technology, who's spending their time on it, whether they're at a
company or not at a company.

And, um, you could unpack the motivations around that, but it
almost doesn't matter. It it, it is about the curiosity. And I think we're
at a moment in time in a, a period of profound technology change
where like curiosity is rewarded disproportionately. Uh, and so I
think that is part of it, is making sure that we've got the, those
people coming in, uh, and folks who have been tinkering and
learning with the tools and all of that.

I think that's true across every single discipline. Uh. One of our, one
of our core operating values is around mastering your craft. And
like, if you're not thinking about how AI can help you in whatever
you're doing, you're probably not mastering your craft. Uh, there's
just too much going on. So I, I, I'm like a big believer of like, a lot of
this is top of the funnel and just kind of like the signal through the
front door, then bringing 'em in.

I think it actually kind of happens pretty naturally because I do think
that there is like a lot of latent energy people want to learn. They
want to. Figure this stuff out, but I think just seemed to be shown,
you know, they need to get to ship. Can can we just double click on

[00:30:17] Henrik Werdelin: the, like to learn? This is a question I'm
not sure from who owe you it might be best.

Um, and John, you probably from experience in, in Jeremy probably
from, you know, academia. But, um, I was talking to a friend of mine,
I was Kaman who was like a, you know, a high end coach and I was
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And he was talking about what he called the self-authored mind and
the socialized mind. Like basically you had some people who kind
of like falls into these categories and the majority falls into the
socialized mind. Like, like to do what we've always done in an, in an
age where. You'll probably see more and more of our team
00:00 52:29
members do more and more different types of work.

Because like the classic boundaries is kind of, I guess, being also
torn down by ai. Yeah. How do you think as a manager that we
encourage that? Or is it purely in selection of candidates that we
can kind of do that?

[00:31:30] John Waldmann: I, I think both, and this is as much to do
with the experience around AI as it is the last 10 years of running
homebase.

But I, I think in the recent experience, I do think, um, first that you
have to give permission to your team and like really unlock that
latent curiosity in the things there. Uh, and part of that is
establishing a framework and setting the expectations higher of the
previous way of working is, is not gonna cut it anymore.

We were very intentional when we kicked off this year. That it's day
zero. We are a new company. We are approaching everything in a
new way, and that is our expectation going forward. We have a a, a
counter in Slack every day that just increments up from January 1st
on what day is it at the company to just kind of instill of we are not
this company that we were in the first 10 years of our life.

So I think part of this is setting the tone as a leader and that enables
your team to do the same thing that enables your leaders to be
more aggressive and. Kind of expand the Overton window of what
was possible in the company again, 'cause that's that, that tends to
get narrower over time. I think the second part of it is, you know,
hiring a lot of people over time, managing a lot of people, seeing a
lot of leaders, manage a lot of people.
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I kind of think now that there are a set of traits and things like this,
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sometimes of like what we are as a company and kind of where we
should be investing our time to bring people along.

And that may sound really harsh, but actually I think it is just like a,
hey, sometimes we are trying to fit a square peg into a round hole,
and the type of company that we are is just not the right fit for the
person that's here. The cultural values that we want. Whether that is
like where we are today or aspirationally where we want to be, just
00:00 52:29
may not be the same fit for the person there.

And I think it's back to like, if you actually care about the person,
stop trying to like hammer them into the round hall and instead just
like acknowledge that it may not be the, uh, the fit that it once was.

[00:33:32] Jeremy Utley: Can you talk for a second about, I mean,
let's get super pragmatic. Let's just geek out for a second.

Yeah. Things like KPIs, OKRs. What is the evidence? And it, it could
be soft, right? They, they just have demonstrated they aren't curious.
But like, if you think about managing people and you've gotta
manage their performance and in some cases help them find a
better fit, what are the specific things you've baked into the system
to alert you to when it's become clear someone's not a fit?

[00:34:02] John Waldmann: Um. I think, you know, we do use OKRs.
We've used a different variants of OKRs the last few years. Uh, for
better or worse, we use OKRs. Uh, and, and I do think some of this is
like increasingly the objectives, uh. Are very clearly aligned to the
future AI driven company that we want to be. I think it, it, you know,
back to roll the clock back, it was like we're setting objectives for
which, like this solution to it probably requires AI to now the OKR is
explicit on it will require, uh, ai.

And so at some level you have to set the outcomes to require the
things that you want to see. And if you're then not seeing it. The gap
is quite clear. You know, it, it becomes less around kind of like the
qualitative traits and things like that and the outcomes that those
qualitative traits would lead to.

So very tactically, it's like, well, you know, we believe that AI can
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engineering velocity. Now that goal is about adoption of code gen
tools and the number of lines of code written by, or the, the
percentage of our code written by AI tools.

So it was like a very clear example. Now it's like the light is very
clear on who's using the tools and who's not using the tools. So. I
don't know if that's actually like a good answer for you. Did
[00:35:40] Jeremy Utley: you to that? That's great. No, it's great. I big,
00:00 52:29
I mean, I think, I think part of the challenge with, and, and you're,
you've got the benefit of being a more nimble organization, more
agile, et cetera.

Mm-hmm. I think part of the challenge, if, if I look across especially
larger organizations, the reason some folks aren't, um, you know,
collaborating with AI tools is because it's okay not to, inaction is an
acceptable action, so to speak. I think what increasingly has to
happen is leaders have to take inaction off the table at inaction has
to become the punishable offense, and that doesn't mean success
is required, right?

For example, I can imagine a KPI where you say, Hey, I wanna see 10
AI driven experiments in six months. If you show up, all 10 can fail.
That's perfectly fine. I we're gonna high five, whatever. But if you
show up and say, I only did two, we're gonna put you on a
performance improvement plan. And if that happens again, you
have to look for a new you.

We can't have people who aren't constantly experimenting on this
team. Right.

[00:36:40] John Waldmann: That that's exactly right. That's exactly
right. And I think what we had to do was make sure that we were
being. Um, clear to the team on the journey that we were going on
and giving them the support and tools to make that jump.

Like I, I, I want to make sure that we are a place where people could
be trained and developed and find the resources available to make
that, but at some point it does have to be pulled,

[00:37:03] Henrik Werdelin: I think. I think all this is incredible and
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Um, I was curious if we go back to your customers, let's say that we
have you, I have a friend who's a tree cutter or has like a small
restaurant besides obviously use Homebase as a vendor. That
seemed to be doing a lot of the thinking for him. Yeah. What is
some of the stuff that you, like how we, we now talked a bunch
about how do we suggest.
That, you know, midsize to big size companies, kind of like a doing
00:00 52:29
this. What would be your recommendation if somebody sat down
and said, Hey, I run this restaurant, I do this thing. You know, how
should they think about like doing the same journey as you've done
with your company through this

[00:37:47] John Waldmann: change?

That's a great question. Um. I'm sitting here as a technology
company, and it's very easy for me to say this as a builder, as a
company full of builders of like, how am I unlocking the, the best
version of the team that we have who are incredible, who are
curious, who have learning mindsets? H how am I giving them the,
the, the room to run?

You know, I am all about like, let your wild stallions run. Uh, like
that's who you want at the company is the people that are just like
born to run at a certain speed and accomplish great things. Tech is
full of that, right? It's very easy for me to sit here as a, as a company
and say of like, that's what we're gonna culturally be as a company.

I think you're running a local business. The nature of your business
is so different, you know? And, and I think that is why like company
like Homebase can be so successful because I think for the longest
time, uh, technology frankly did not honor these businesses in what
made them so special. So.

Important to the world, what made their teams so unique in what
they provide to the world? We are absolutely doing a disservice to
our customers if we're saying, Hey, in order for your team to take the
next step in the journey to be a great restaurant and serve, you
know, deliver incredible customer service, they should be spending
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moment in time, deliver solutions that are allowing them to get to
the thing that they are uniquely good at. And the thing that allows
them to be a thriving local business today.

Ultimately that is about the experience. It's all the things that exist
out outside of the tools and how the business runs. Uh, it, it is about
the ways that they're using tools to kind of accelerate their, their
special and unique advantages. That's almost always about kind of
00:00 52:29
the company they're building, the way that they serve their
customers.

It is almost never around the ways that they choose to run payroll.
Uh, there is no unique advantage in that there is just time spent. Uh,
the thing that we can hope for as a company is we give them that
time back. The other thing we can hope for is like, give them the
tools to be incredible managers and leaders and automate some of
that work for them too, because.

A lot of 'em are not classically trained managers and are coming at
this as a first time manager or first time leader. So I think we have a
role to play there, but I, I think the part of the world we serve is like,
should be more enabled than kind of technology first.

[00:40:22] Jeremy Utley: Is there a world, John, where your
recommendation, uh, I dunno if this is a statement or a question or
what, it's possible that your suggestion to these folks, if, if they ask
you, how can I become augmented with ai?

To your point, it's not about them automating their own payroll or
whatever, but is there something about thought partnerships,
strategic thought partnership? I think one of the comments, and
there were kind of recurring themes on this show in these
conversations is. There's something about kind of workflow
augmentation and automation and all that stuff, but then there's just
the thinking partner.

Like for a small business owner, basically they've got trillion dollar
coach Bill Campbell in their pocket who if they know to provide
Chad GBT, that context. I want you to play the role of Bill Campbell. I
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of that's available to somebody. Is that how you would recommend,
you know, a small business owner kinda leverage AI or, or what's
the, what's their immediate, uh, low hanging fruit opportunity.

[00:41:29] John Waldmann: Obviously the lowest hanging fruit
opportunity is use homebase. But we'll, we'll take that as an
assumed. Of course. That's, but that
[00:41:35] Jeremy Utley: fruit is like on their lips.
00:00 52:29

[00:41:36] John Waldmann: The second thing that they should do,
uh, yeah, I,

[00:41:40] Henrik Werdelin: you forgot to say that. You're, you forgot
to say that. UL prove entrepreneur. I do the,

[00:41:43] John Waldmann: yeah. Join home base.com. Uh, start for
free today. Uh, perfect. We are a freemium product. Uh, no. The
after, after going through that journey. journey@joinhomebase.com
and getting set up. The next thing. Yeah, I, I think that's a great point
around using chat GPT and just the, the amount of coaching and
support available in that, uh, founding a business is a lonely journey
and it is an incredibly hard journey. And I don't think the work and
uh, kind of courage that every single local business that exists in
this world has, is demonstrating, gets the amount of appreciation
that it should. Behind every single local business. There is an
incredible story. Like that's one of the best parts about serving
these local businesses is like that.

The courage that it took for this person to put a big part of themself
out into the physical world, serving their community and the people
that they know. That is a very, very profound statement of
entrepreneurship. It's vulnerable. Yeah. Yeah. So much vulnerability
in that. Forget about like the financial, uh.

Risks that people are taking and doing it, but like the emotional risks
that people are taking that are profound and yeah, I, I think chat,
GPT or whatever, LLM of choice, dude. Dude.

[00:43:02] Jeremy Utley: Okay. Okay. I just have to interrupt 'cause I
like, okay, Hendrik and I did this the other day with Blair. Let's, let's
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recommended GPTs that are all about small business coaching,
right? You could encode. Some GPTs based on world-class
coaching as you understand it. Right. Um, and I wonder if there's like
the top five, I mean, Bryce Shamal from Moderna who we
interviewed a while back mentioned AI as assistant, AI as coach, AI
as expert and AI as creative partner.
So we even take those four things. It's like, yeah, what if there's
00:00 52:29
home base assistant, which is just a custom GPT. I wonder if that
might be a really interesting way to kind of build trust with small
business owners. It's like you can act if you pay what, you may not
even have to pay open AI to get access to GPTs, but we've built
these tools to demonstrate the power of, you know, coaching
expertise, creative assistance.

[00:43:56] John Waldmann: I think that is a wonderful and
provocative idea of. You know, there, there's so much of this that we
are putting in and building home base around of how are we
bringing help to the tasks and the things that you have to do and the
regulatory risk, and how are we offloading all of that from you to us
in your brain.

Uh, but I do think that there is a part of this that is emotional too,
and being able to provide that coaching and support in a way to a,
to a business owner or a leader. You know, we all know as, as.
Leaders and managers. So much of what we do is the support that
we're providing other people and yeah, it's a hard thing.

Uh, so yeah. I I like that idea.

[00:44:40] Jeremy Utley: Well, that's o one thing that we aim to do
on this show is always give a gift back to our gift. There you go.
There's your the My friend. So thanks so much for joining us, John.
This is an awesome conversation. Okay, Jeremy, professor. I know
you're, this is catnip for the, for the BarkBox guy.

Huh?

[00:45:01] Henrik Werdelin: I see what you just did there. See what I
did? See what I did. We 1st of April, uh, the day yesterday of this
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[00:45:18] Jeremy Utley: that's so funny.

[00:45:20] Henrik Werdelin: But, um, okay, so I mean, like, there.

A lot of things obviously resonate a lot with what John was saying.
A, I mean, like he's just an incredible leader and I think it's so cool
when people come in the pot and talk so honestly about some of
the issues and I think this problem of like, how do you get my team
00:00 52:29
to kind of embrace this new technology is something that.

Every founder is now trying to figure out. And I thought he had some
incredible suggestions. And, and I think also just kind of, it was nice
to hear somebody else who kind of like is, is trying to do the same
thing and find it complicated. Um, so I think that was one thing I I I
love that you're, you had a quote on, uh, inaction is an acceptable
action.

And I think for people who run this organization that thrive to be
more AI first just will have to stop accepting that, uh, 'cause there's
just. You know, and I think, you know, as we've been doing this
podcast, I think we also started with this curiosity mindset of like,
how do you do this? And how do you get people to walk through
path and how do you inspire and make sure you do the Slack
channel and stuff?

And I definitely, I think interestingly, you have. Failed a change of
tone in the last year and a half where a lot of people come on now
and a little bit have the attitude of like, okay, playtime is over. You
know, like, we, you got access to it now you actually have to use it.
Well,

[00:46:40] Jeremy Utley: I, I mean, you, you know that I'm obsessed
with play, so I won't say playtime is over, but I will say, uh, it's no
longer optional.

I don't think playtime is over. I mean, not to, not to mince words, but
I think playtime is now mandatory. Yeah. Whereas perhaps before it
was optional.

[00:46:53] Henrik Werdelin: Yeah. Right. I think that's it. Well put.
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Um. And then I kind of like, uh, I dunno, this a very practical thing.
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Uh, I just like the idea of having more people say, Hey, that's great.
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Gimme 10 ai Examples of that, I, I mean like if with. Uh, rep or
lovable or you know, like all these different tools that are available
for people to make their own prototype. There really no reason why
even like teams that may be a little bit slower to adapt this thing like,
uh, finance team, legal team, whatever it is, uh, uh, except we've
heard many examples of those teams being the first.
But besides that, I mean, I just say, you know, you need to come
00:00 52:29
back with 10 examples of something tangible of how you solve this
with a product. And just get into the rhythm of practice. The vax on
vax off, kinda like motion or ate kind of, uh, reference, but the, to just
practice in productizing solving the problems with ai.

And that is, I think, increasingly also just something that we should
just ask people to do.

[00:47:55] Jeremy Utley: Well, no, no time spent kinda building with
AI is wasted time. So even if that product doesn't ship, even if that
lovable prototype doesn't go anywhere. You're building kinda muscle
memory and familiarity with tools that you, that will become more
indispensable to you over time.

Therefore, play and build, and I mean, I love the example that he
gave at the beginning of the show, which is the product review
process. The roadmap process has totally changed now instead of
reading a bunch of 20 page documents, which basically becomes
the job. Now we're doing two or three minute demos of real live
prototypes, and all of the time that we were spending reviewing our
plans is now been redeployed in the field.

We're able to be learning and inspiring and getting feedback. It's just
this incredibly counterintuitive reality. I think that an ai, I. Augmented
workforce is far more able to be more human than the workforce
without. And I think the fear of kinda cybernetic organization and
cyber, like all of this vernacular, is actually, there's scare tactics that
keep people from being able to be more human, to spend more time
with their customer, to find better problems to solve, and on and on.

I also loved, um, I think he mentioned the cultural value is mastery
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I think what he said was, if you don't see that you're blind, or at least
that's what I wrote down, maybe that was my interpretation, but to
me that it's a great reframe of what does it mean to have a craft and
master it. You, you now gotta incorporate ai.
[00:49:42] Henrik Werdelin: Is that it? Not as in, is that it? But like, is
00:00 52:29
that all that was that, that's

[00:49:46] Jeremy Utley: all, that's all you took out?

Uh, I've got, I mean, I have like nine pages of notes here. I can't read
and speak at the same time. I think, you know, one thing I will say
that's pretty, uh. Was was great is, you know, the, the irony of, I
dunno if it's irony, but the hospitality person, you know, who hates ai,
who, once you start to imagine what you go, oh well I don't really
want to do that.

Oh, and I don't want to do that. And I thought John's kinda clever
shift from, it's not, the conversation should be about the technology,
it should be about the problems we're solving and the the how is up
to us. Right? But if you can help someone. Be clear on, you know,
the fact that they've gotta screen a hundred resumes for the
hostess jock.

Nobody's raising their hand and saying, I can't wait to read all these
resumes. They're saying this, these resumes are actually keeping
me from running my restaurant. Right? Think shifting from a focus
on the technology to the problems that it solves, I think is really
brilliant.

[00:50:45] Henrik Werdelin: I think that's it for this wonderful
episode.

[00:50:49] Jeremy Utley: Henrik, what's our, what's our, um, what's
our code word?

[00:50:53] Henrik Werdelin: What about, uh, small local business?
Because I do think that, like what he said about how important it's,
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and how little credit they get is just a hundred percent right, like it is
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you walk down all through these small stores and they're always
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they're always like, just makes you feel welcome and make your day
and it must be exhausting having to make sure you stand up there
and restock the store and get it ready every day or coffee shop or
whatever it is.

[00:51:21] Jeremy Utley: I think that's a great code word. I will
submit another so people have two options and they can just decide
what they agree with. I say distraction because while I was saying
what stood out to me, Henrik was sending me a meme. He wasn't
00:00 52:29
even listening. So I think the code word should be distraction, but.

It's not to you, you're good to choose. Do you wanna say, you know,
support small business? That's because

[00:51:43] Henrik Werdelin: I think you look like data from uh, star
Trek today. And so for people who watch it on YouTube, they can un
unbelievable. Unbelievable.

[00:51:52] Jeremy Utley: I'll leave it to you to wrap this program.

[00:51:55] Henrik Werdelin: Okay. And with that, thank you so much
for listening to another episode off Beyond the Prompt and as
always incredible.

Incredibly just ex incredible. We just really appreciate that you're
staying to listen all the way to the end. And. If you are here, will you
please, please, uh, give us, like, give us a subscribe, send it to a
friend so that we can grow our, um, listenership, uh, would very
much appreciate that. I totally killed that one, but

[00:52:20] Jeremy Utley: there you go.

I love it. No, leave it. Leave it. Thank you. Leave it. Thank

[00:52:23] Henrik Werdelin: you so much for everything and we will
talk soon.

[00:52:27] Jeremy Utley: Aio.

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