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"The AI is only as good as what it knows about you."
Most companies are buying AI tools. Almost none of them have the data, processes, or systems in place for those tools to deliver.
The CRM is a mess. The processes aren't written down. The tribal knowledge is locked in three people's heads. Then the AI gets layered on top, and nobody understands why it doesn't work.
AI-Ready or Not is the show about fixing the foundation first.
Host Travis Scott talks with founders, operators, authors, and practitioners about how they're actually using AI. What's working. What's not. What they had to do to make it work.
New episodes every two weeks.
Travis: thanks for, for hopping
on and, and being guest.
Number one, uh, for the podcast.
But yeah, wanted to have you on.
I've, I've, uh, been reading
your newsletters and, and we've
known each other for a while
and, uh, followed your evolution.
And, and now that evolution includes ai.
Like a lot of, a lot of, a
lot of companies, a lot of
solopreneurs, a lot of founders.
But I think.
You know, one of the things, one of the
most important things before layering
AI on, I mean there's a lot of benefits
it can add, but just like automation
and in free time, your book, you talk
a lot about automation and if you do
something more than once, try to automate.
And I think AI is a next level for that.
But with even old school automation, if
the foundation, the infrastructure is not
built properly, it will just make that.
It worse.
Right.
So so you've kind of already been, you
know, on the automation train for a while.
And, uh, I think in a recent newsletter
you mentioned that, you know, with
chat GPT and Claude and early on you
were kinda simultaneously impressed.
And underwhelmed.
But then something changed.
What was the catalyst that that
changed that perspective for you?
Jenny: Yeah.
Well thank you Travis, for having me.
And it's interesting because my second
book Pivot is all about navigating
what's next, navigating change.
And the mantra for that was, if change is
the only constant, let's get better at it.
And so in a way, this whole AI revolution
is affecting every single person because
it's changing a lot of how we work.
And then my third book, free Time came out
six months prior to chat GPT launching,
and the whole promise of free time is set
your time free through Smarter Systems.
I see
Travis: I.
Jenny: time as a verb.
a skill.
It's something you can get better at.
And the nerdy way to say it, it's
about operational efficiency.
I wasn't teaching how to make more money,
although I do think that's a result.
I was teaching how to do less busy work
so you can do more of your best work.
And I found that having worked at a.
A startup company as the first employee.
I worked at Google as it
grew from 6,000 to 36,000.
And then I worked in my own business and
I repeatedly saw either the owner or their
team members getting what I call beset by
the burdensome bees, bored, bottlenecked,
burned out, or buried by bureaucracy.
now you gave me a fifth B that
we could add, which is bloat.
if you do have really.
Heavy Franken stacked software
or really bad processes that
weren't given a lot of thought.
There's a lot of bloat and waste as
well, and even the best businesses are
subject to entropy where like a house
in the woods, chaos will eat the house.
If you don't actively, I, I am
mixing metaphors now, but like,
give your business a haircut.
And cut the things and systems and process
and backend that are no longer working.
So that was already my passion with
free time, which is the 27 chapters
are about systems thinking strategies
where even if the owner felt like,
oh, I already know all this, they
could hand the book to a team member
and say, here, this is how we work.
This is how we work in a really
lean, agile way at the intersection
of revenue, joy, and ease.
And so of course, as AI tools
started rolling out LLMs and Chat.
I was impressed.
Wow.
Right up home in the blink of an eye.
But for the last few years it
did not m transform my business.
My day-to-day operations and I work
as an author, keynote speaker, I
license my IP to companies, and now
Pivot and free time are sort of my
two business skis, my two focus areas.
But are
Travis: we're recording the.
Jenny: the end of April.
It wasn't until the start of 2026 when
Claude released desktop and they re or
desktop existed, but they released cowork.
So people who were not software
engineers could have a way in and not
just cowork computer use, where it
takes over your computer scheduled
tasks notion around the same time, and
Travis: February.
Jenny: released Custom agents that
were free are free to try until May
4th, depending when you listen to this.
To me, all of a sudden my
brain, my body was on fire.
I have not been able to
sleep for the last month.
I have always loved technology and to
me, the feeling that I have, seeing
how quick the innovation is and how
massively it has already changed and
improved my business and my life.
I feel that we're in, we have turned a
corner as at least if you're a business
owner, that there is an era where
computers didn't exist and then they did.
internet didn't exist and then it did.
for me personally, I lived through some
of those, like I'm an elder millennial.
I remember the days before
I got my first computer.
I remember before there was
the internet and a OL chat.
I remember before blogs were a thing.
And now this feels
exactly the same because.
In the span of two weeks time, I've
automated so much more in my business
and these custom agents that run
on schedules are sophisticated and
they catch things I wasn't catching.
It's required me and my team member to
almost have to, we, we do have to retrain
Travis: Myselves.
Jenny: our entire world
because it can do so much now.
And the
Travis: Last thing I'll
say it's different than,
Jenny: It's
Travis: it's similar to automation.
The automation was, if it's a,
Jenny: like if
Travis: like if any of
you're familiar with,
Jenny: or Make or
Travis: literally, I
Jenny: you plug
Travis: plug in very specific and
Jenny: and that
Travis: that is kind of,
Jenny: know,
Travis: you know, software engineers like,
Jenny: okay,
Travis: okay, I want my software to.
Jenny: each other.
I'm gonna plug in these steps
and it's gonna do what I say.
But agent AI is even more powerful
because with your own natural
language, it can do it for you.
It can improve the things
you don't even think to ask.
And it's recursive.
It improves itself with
every run if you ask it to.
It's just mind blowing.
And we're only at the very beginning.
Travis: Mm.
Yeah, absolutely.
I, and yeah, I'm, I'm Gen X, so I also
remember the, the transition, right.
Pre and post internet and, and everything.
And I think you, you'd said
something interesting about how
we can help you improve on things.
You didn't even.
Realize or, or thought to.
Right.
And a, a big thing for me lately is when
I am writing prompts I've stopped just
trying to think of everything that I could
possibly include for context and what
my, I've, I've included reverse prompting
as a key instruction for my entire.
Claude to say, if, if I'm not
just asking a general question
about like, Hey, what is this?
Right?
But I'm, I'm writing a prompt
and there's a difference, right?
Then ask, ask me questions for,
to provide you with enough context
so you can perform the task.
And, and so now basically I'll write a
prompt and I'll say, uh, you know, if
I needed to act as something certain,
I'll say, act as if you're this.
Uh, this is what I need you to
produce and this is the kind of
format I need, and that's it.
I don't get into any context and
then it will ask me questions and it
kind of, sometimes it gets annoying
'cause I'm like, come on, come on.
But it's asking questions
that I would not have thought.
To include his context and it actually
gets me to the correct end point faster.
And so I think that's a, a key element
is, is that ability for it to see what
you, you can't see on the edges, right?
Jenny: Yeah, absolutely.
I have
Travis: have learned this
from other people, so
Jenny: credit, but.
Travis: credit, but.
Jenny: Before almost every prompt
I say read my context files first.
And that's why desktop is so powerful.
And context files are
important because you
Travis: Wanna tell
Jenny: about you, about your business,
your clients, your goals, how you
Travis: how you work?
Jenny: uploaded my books as markdown files
or had the AI convert them to markdown.
with every prompt I say, read my
context files first, and then I
explain a little bit, and then I say.
user question and you inter caps, I
learned that inter caps does matter.
It's called Camel Case Capital
A Ask capital U user question.
It's all one word, no spaces.
And that tells Claude,
interview me about what I want.
And it is so powerful and I'm so impressed
by the questions that it asks and how,
and I say, ask user question until you
are 95% clear on what I'm trying to do.
And so, yes, I'm with you and I
love, thank you for reminding me.
It's called reverse prompting.
I forgot about that.
Travis: Yeah, and I like the 95% piece.
I've kind of added something
to, to the lines of.
Help me make it bulletproof
or things like that.
Right.
Kind of the same thing, but I
like giving it a percentage.
And yeah.
And you mentioned context files.
How, how, how are you using those,
you know, they work for general
prompts, uh, you know, like you
mentioned, read these files first.
But how, how are they important
in terms of using agents
like you're using them now?
Jenny: Well, the difference Chat was
starting to do this, whether you use Chat
GT or Claude, it was starting to create.
Where you could upload same core files
that it would reference when you chat.
But chat was just a little more
Travis: Transac.
Jenny: with, and again, I keep referencing
Claude desktop because to me right
now, that's really the game changer.
The context files, there's the
ones that you create that you might
want it to reference every time.
You're working on something.
And for those of you, I know you're
probably at varying degrees of, of
where you are on all of this, but in
very simple terms, a markdown is just
stripped of all extraneous formatting.
So it's just how the AI reads
things very quickly with the minimal
token use compared to Google Docs
or God forbid, Microsoft Word.
That's so just overloaded with
formatting and a bunch of crap
that slows down these LLMs.
So.
I learned a lot.
I mean, what I love right now,
what's happening in this space is
so many people are open sourcing.
They're sharing, they're sharing on X,
they're sharing GitHub repositories,
they're sharing on Substack.
They are so generous with
try this prompt first.
Try this.
I am.
I am now creating a resource guide
too, for anyone who joins my free time
community, where I'm giving a database
of all my favorite prompts because, uh.
Like someone shared with me when I
was just getting going with this,
something called Claude Council.
It was a Google doc.
I'll send it to you, Travis, if
you wanna put it in the show notes.
Travis: Yeah,
Jenny: all you do is copy,
paste, and you ask a business
question, like some strategy
Travis: question.
Jenny: you're genuinely debating.
Somebody else engineered this epic prompt.
You just copy paste and all of a sudden.
Five advisors weigh in a
contrarian, an expansionist, a
practical one, an imaginative one.
Each weighs in with their opinion.
They debate each other.
Then the, the, the prompt, like
then they read and see what are the
blind spots that no council member.
Noted.
And then there's a recommend, a
summary recommendation at the end.
So it's just this very cool
process that if you have context
Travis: Files already
Jenny: business and your clients and
your goals, suddenly you can engage an
Travis: in
Jenny: prompt like counsel
and get really solid answers.
And I
Travis: Wow.
Jenny: combination of those
two things that, for me, the
experience has been miraculous.
I feel.
So
Travis: So empowered in my business.
Jenny: less alone in my business as
a solopreneur, less alone in the big
decisions, how I approach things.
It gave me the energy back to even
relaunch my private community, which
I've been paused for over a year.
And I was kind of flailing.
It's like now I can offload so much
more of the work that was draining
me or just really messy, like
Travis: Like all the stuff
Jenny: under the
Travis: rug.
Jenny: was not urgent or important.
And oh, I just feel so
empowered to get things done.
Like I, I shared a story of how Claude
Code took over my computer for a day
and fix 300 broken links on my substack.
And that was such a relief because
even my team member doesn't
love doing that kind of thing.
So not only did I enough to pay anyone
other than my a hundred dollars a
month max plan on Claude, but it
worked tirelessly in the background.
It's just so empowering.
Travis: Yeah.
Jenny: I know.
I'm sounding really hypey and I
actually sat on the sidelines for the
last two years just because I didn't
wanna turn anybody off by talking
about AI and now I can't help it.
I actually don't want people to be
left behind just 'cause they're.
Intimidated by all this.
If you hate it for ethical,
environmental privacy reasons and you're
morally opposed, I totally get it.
I share some of those concerns, but I,
I can't keep sitting on the sidelines
about it, just for that reason.
For me personally,
everyone else is different.
Travis: Yeah.
Yeah.
No, I, I, I agree and I
have those same concerns.
And it, it is just some
cognitive dissonance, right?
That, that is involved with it.
But yeah, I was kinda the same
boat, like there was all the hype.
But I wasn't quite seeing it yet.
Like the actual, you know, how can this be
helpful outside of just a novelty, which
is kind of what I felt it was at the time.
And, and I'm a HubSpot,
uh, partner and I, I've.
Implemented HubSpot for lots of
companies over the years and they,
they were among the first CRMs to
introduce their own AI embedded into it.
And, you know, early on I just was
like, I don't really see the value.
It's almost gonna take me more effort
just to talk to this thing when I already
know how I'm gonna create what I'm
gonna create that it might help me with.
Right.
And then I went to their
inbound conference, uh, in
September in San Francisco.
And, before I've just been
like, yeah, yeah, whatever.
I don't see it.
. This isn't helpful.
It's noise.
But this year or last year, I
guess I, I remember thinking
it's finally turn the corner.
I can actually see how it's useful.
And it was driven by agents, kinda like
for you, that was the turning point to
where, okay, this can actually help me
in a lot of different ways, not just.
In my business where I am solo, to help
prevent me from being the bottleneck
that I've been for the last five years.
But I got diagnosed with A DHD
in 2023 after having it for 40
plus years and not knowing it.
Uh, but that it all made
sense once, once I found out.
And so there's things that are strengths
and there's things that are profound
weaknesses for someone like me with a DHD.
And I was sitting there during inbound
thinking, and the very first thing didn't,
didn't, it didn't, it wasn't how can I,
you know, replace a, an assistant or VA
or ea or have it run all these tasks?
It was, how can I leverage this
technology E so I don't have to focus
so much on my weaknesses, right?
And I can focus on those strengths and
the superpowers that I have from A DHD.
That some people may not have.
And that to me was just a light bulb
of like, finally, finally something
can help me get around the system that
has been built, not for people like
us and level the playing field, right?
And so that's what I was really excited
about and it was that point that I
started to really dig into agents.
The flight home I was
sitting in the airport.
At SFO and I was creating something in
Google to block my calendar if I had
x number of hours already scheduled or
this number of meetings scheduled, and,
and now I don't remember how I did it.
And so it just runs and I don't know
how to turn it off, but it works.
I guess if I'm gonna protect
my time, it's, it's relentless
because it's always blocking it.
But but yeah, I think
there's just so many.
Positive I implications of AI for people.
And instead of thinking of it as
replacing you, to me it's, think of
it as building a, a better you right?
With these agents behind you helping you.
Right?
So, so yeah, that was kind of
the turning point for me as
well at that point in time.
Jenny: And I love that story, and I
think there's nothing so joyful as
when you fix something that genuinely
feels frustrating or friction filled.
Oh, and just like for me, I have it read
over 50 newsletters I subscribe to over
like maybe 900 Substack newsletters.
I think of it like I run a newspaper
and I'm the CEO or I'm the editor in
chief and these are my columnists.
But in any case, it's obviously
more than I can keep up with.
And now my email assistant, which
is a custom agent, I use Notion just
'cause I've been in notion for five
years, but every day I've told it.
Scan through my newsletters and
surface recommendations, what
you think I would like, and it
knows I'm interested in agent ai.
It knows some of my, I'm interested in
writing and craft, and so now it tells me
what's happening in my same box folder.
That's the service I use that filters
all newsletters out of my inbox.
And I'm missing less, but I'm
catching more in terms of.
Content that I might find interesting
that before was just getting
totally washed out of my email.
I wasn't seeing it whatsoever,
and sometimes I was missing
important billing stuff.
So I think when people are intimidated
with where to start with this stuff.
I would say either start building
something that just sparks joy,
like around one of your habits,
you know, uh, hobbies or habits or
like you said, Travis, it's really
like looking at a pain point or a
bottleneck or a frustration or a drainer
and saying, could the AI do this?
And now you can just ask Claude in code
or desktop or cowork, can you do this?
What do you propose?
How, how do you suggest we go about this?
And it will tell you as well.
You could even just say, this
is what I'm frustrated about.
user your question until you're clear on
what I need, and then help me brainstorm
solutions and ways you can help.
So I think it's
Travis: It's also learning right now.
Jenny: It's a skill to ask
Travis: Ask
Jenny: for
Travis: help,
Jenny: because it can give it now.
Whereas in the past it was really
hard to ask Za Zapier like, or
Zapier, I never know how you say it.
It was really hard to ask
automation tools like.
can you
Travis: help.
Jenny: You have to go to their
help center and still really slowly
learn how to fix whatever you are
breaking, whereas now you don't.
It takes over.
It fixes it for you.
It tells you.
It's like so remarkable how capable
and imaginative they are at problem
solving ways beyond you can think.
So I do agree it's such a.
Such a like Iron Man superpower.
We've all been given
Travis: Yeah, absolutely.
And I think if you've.
Been around technology and
the evolution of everything.
Like, like we have, and seen it go
from, from nothing to where it is now.
You know, we, we understand that things
are gonna evolve and it's gonna change
and it's gonna look drastically different.
Right.
I mean, the internet evolved and looked
drastically different, uh, over time.
And I think that, and I think
that also is what makes.
Some of us skeptical of things, of
jumping into early of the hype and,
and everything knowing, hey, it's gonna
evolve and maybe it's just not ready.
I'm not ready for where it's at right now.
But I think, yeah, I think the sooner
you can jump in and build a foundation.
The less catch up 'cause it is
moving fast and I think it's
gonna be much more difficult maybe
because now you can't ask it.
How do I do these things?
So you can catch up quickly, but
there's gonna be a whole lot further
you have to go to get at to the
same level as someone else, right?
And of course they're gonna make
it look easy like everything else.
People with experience make it look easy.
You get frustrated when you
can't get there in a day.
But it is gonna take time and
I think people should get into
it as quickly as they can.
I think so.
Jenny: might have to dedicate time like.
I, there's another guy who said
this on Lenny's podcast, which
I really enjoy, where it's
Travis: It like
Jenny: it's
Travis: it's not gonna happen in a day.
That's not gonna happen week.
It's not like
Jenny: take a week, learn it, and you're
Travis: done.
Jenny: You, I
Travis: I think all now have to carve out.
Jenny: percentage of time to
be learning and playing around
and experimenting because.
two days, there's new feature
releases, things change.
The interfaces change.
I think it's part of our
job now, no matter what kind
Travis: Kind job you actually have
Jenny: I mean,
Travis: mean, again, unless
you're totally opt out.
Mm-hmm.
Something else.
Jenny: But I see it
Travis: it part
Jenny: now and as part of
my team member's job as
Travis: as
Jenny: she, I've told her, please put
learning your time sheet and put a
Travis: learning plan.
Jenny: and there's gonna be growing
pains because it is awkward sometimes.
We or now I have to figure out how
to delegate to her subsequently, then
to the custom agent or maybe to an
agent that manages other subagent,
like it's a really weird time.
I think we all have to be, a
little humility and also dedicate
the time to learning right now.
Travis: Absolutely.
Yeah.
And yeah, and, and it's hard.
I think that's probably the
most difficult thing for people.
And that's why I just finished rereading
Cal Newport's book Deep Work because
it's that important, I feel to really
good, good at carving out that time.
Blocking it, protecting
it, uh, with everything.
You have to be able to, to go into
that deep work of learning and
testing and experimenting, right?
Because as soon as you let that
dry up, it's going to accelerate.
Past you.
Right?
And that's my biggest fear right
now is, is getting too busy.
Business is picking up finally.
And I fear that it's just gonna
eat my entire schedule and I
can't let that happen right now.
And and so I think if you're a company
maybe you worked at Google and, and
I recruited at Microsoft and, and
it was Google's 20% time of being
able to work on whatever you wanted.
That made it hard for me to recruit.
People against Google, but I think
you almost have to work that into
your business model for your people.
Not just for like building new things
like Google did, but for learning and you
know, maybe building through ai, but just
learning and having that time to dig in.
That's uninterrupted, right?
Jenny: Yeah, and I think agree with
the hype, like the over hype as far as
I think I'm hearing some people talk
about it like, oh, you need now is a
good idea and you're capable of building
it, and they're failing to mention,
yeah, but okay, sure you can vibe code
your new idea in three days, but then
the next person can copy it in an hour.
Because they can just hand that to
Claude Code and say, duplicate this.
so
Travis: So
Jenny: it's
Travis: now it's
Jenny: marketing
Travis: the marketing's
Jenny: gonna be
Travis: gonna be different
Jenny: great is your new idea.
Do
Travis: idea.
Jenny: grand or a million or
10 million to throw behind it
Travis: It
Jenny: actually the marketing or not?
It's not just a good idea.
It's not just the capability to create it.
And I think
Travis: I think that's being left out
Jenny: conversation I'm
Travis: hearing.
Jenny: like.
No, the idea is not, that is not only
gonna cut it now, and that's, I think
that's gonna be gnarly for all of
Travis: All of us.
Jenny: Where just
Travis: It's like
Jenny: LinkedIn was,
and slop, amplifi long
Travis: before ai.
Jenny: was like, to me, just intolerable.
Just like a bunch of humble bragging
showboating, really annoying.
Oh.
Uh, now it's like really intolerable.
I, I loathe the Chad GT's
writing style output.
I cringe.
I can't stand it.
But
Travis: but now we're.
Jenny: equivalent in terms
of products and services.
Like there's gonna be like slop sass, you
know, where people make it in an hour.
And stupid story that went viral about
the guy who vibe coded his way, his
first one person billion dollar startup.
It's like, well, yeah, if you're
selling Ozempic and you're
practically running a fraud scheme.
the scenes.
Oh sure.
You can get to a billion.
So I do agree there's a lot
of hype and there's gonna
Travis: Gonna be a lot of
Jenny: challenges, and I do think
there's gonna be really awkward.
Tumultuous periods where we
already know entry level people,
it's harder for them to get jobs.
'cause the AI is so good
at that kind of stuff.
And if you're a
Travis: if you're a business
Jenny: it's
Travis: owner, it's like,
Jenny: Claude
Travis: oh.
Jenny: design.
What
Travis: What happens if you're,
Jenny: What
Travis: what happens
Jenny: your bread and
Travis: if write a letter
Jenny: For
Travis: for me?
I run
Jenny: business.
They're pretty
Travis: pretty remarkable.
Jenny: at talking through
career next steps.
It's not a hundred percent
replacement of a person.
But it's doing a lot.
So I think in every industry we're gonna
have to be looking at this and seeing
how we adapt and it's, I don't think
it's gonna be clear cut or overnight
really for any of us, unless you.
Your pivot is, know,
talking about gen to ai,
Travis: Yeah.
Yeah.
Jenny: say, it's like selling
shovels in a gold rush.
Like you might not find
the gold, you can sell a
Travis: Double.
Jenny: And I'm not saying for better or
for worse, I'm just saying like, it's,
it's gonna be, it's gonna be confusing
and I think it's gonna be confusing
for almost everybody in different ways.
Travis: Yeah.
Yeah.
And there were a couple things
that you mentioned there that
I think are, are important.
The entry level.
The thing is, is really big because
it, it is good at, at those things.
And I think where the superpower comes
in between a person and AI is that person
leveraging their experience and their
taste to know what good looks like to
then be able to coach it and manage it.
Right.
And if you're entry level.
Coming into a, a, a new career, you
don't have that wealth of experience
in you stumbling and learning over time
to then be able to leverage that to
make it really, really work for you.
Right.
And, and then the vibe coding thing
as, as a HubSpot partner and CRMs,
I keep hearing about people vibe,
coding their own CRMs, and I'm like.
I am sure that was a fun weekend project
for you, but now who's now gonna manage
it and maintain it when it goes down, when
you hire people, how long is the training
and onboarding gonna take for them to
learn this new thing versus HubSpot that
they might have used at another role?
Right.
And I think you know, as a recruiter
in technology back in the day.
And, and I would work for a company,
Comcast, Microsoft, whoever, who
would say, you know, we really
want someone with experience using
these tools or these platforms
because the onboarding is faster.
And then I'd talk to people at
companies who had built their
own homegrown, CRM or ERP.
And it is just like, you're gonna
come in and it's gonna be really hard
for you just to catch up to where
you need to be in six months because
you're now learning the basics.
Right?
And so, I don't know if people are fully
understanding the, the, you know, to
kind of Dory Clark's book, the Long Game.
They're not really looking
at the long game right.
With some of this stuff.
Jenny: And it depends how big and
how complex your organization is.
Like I know
Travis: I know people.
Jenny: have canceled Salesforce and big
expensive build outs that they spent a
lot of consulting money on, and they're
gleeful to cancel it and builds in their
own environment and have full control and
pay $0 other than the coding token costs.
But I do think you're right.
It works better if you're a really small
company, like it's one or two of you.
And Markdown files aren't that
friendly for team members to be using.
So yes, you could have it build
a dashboard and that's what
a lot of people are doing.
And now they're launching like
live artifacts and there's a whole
lot launching in that arena as
far as dashboards and shared info.
But yeah, it's gonna be much
harder for bigger organizations
to do that kind of thing.
And.
I guess
Travis: I guess the flip side that
Jenny: the
Travis: the opportunity right now,
Jenny: you're a
Travis: small business,
Jenny: because we're at
the front of the wave.
We're agile enough to
do all this and try it.
friend Travis Strom as well,
has canceled so much software.
He got into open Claw and blew my
mind with what he's created and.
So small businesses, like I
Travis: I think in the last six.
Jenny: at when the pandemic hit, small
businesses were hit really, really hard,
especially as bigger companies tightened
the belt and then consumers, even though
I hate that term, but like day-to-day
people didn't also have as much money
to spend with those small businesses.
But now I feel we have the
advantage because we're agile
enough to try this stuff.
We don't have as enormous like
infrastructure and security
questions and approvals, and I
can't even imagine how frustrated
Travis: Frustrated
Jenny: if I worked
Travis: I would be,
Jenny: company and there were
like all these limits and ceilings
on how I could use these tools.
And approval chains and just bureaucracy.
So
Travis: yeah.
Jenny: guess the part of me I feel
really excited is like, ooh, for once we
get to rock it out ahead and be at the
front of the curve and we're gonna know
Travis: What's coming
Jenny: even the big companies
Travis: because
Jenny: we're able to really try
it first and just dive right in.
Travis: Yeah.
E exactly.
Yeah.
And, and I think that's a, a key
point is the bureaucracy of being
able to use these things because I
couldn't imagine the way I, I use
Claude, uh, in other, other tools.
To have to give that up or have
to ask before I, I do something.
I, I don't know if I could, I
mean, that's why I work for myself
because I can't do that stuff.
Jenny: Right,
Travis: or, or not ai.
Jenny: Right.
Travis: but but yeah, that, that's,
that's in, uh, that's a great point.
And what, so, and you mentioned
using notion and, and its Agen
features and Claude and, and I think.
For people who are just getting into it.
I, I think a key point is
understanding there's a lot of
different AI platforms, right?
There's Claude and Manus and
Perplexity and, and Notion has its
own, but I, but I feel like they.
Have their own strengths and
learning how to use them for
different things I think is also key.
And so when you're using notions,
agent functionality, and clawed,
how are you, what's the delineation
between where you'll use Notion
and where you'll use Clot?
Jenny: So all of my notion
agents are powered by Claude.
I get to choose the model and they
give you seven or eight choices at
the time of this recording it's opus
seven, but I'm sure within a week
it will be some other wild model.
I think the main difference
is it, it depends.
Once you have what I call a
delightfully tiny team or bigger.
Notion is friendlier as far as
team collaboration and getting the
business out of your mind and onto a
shared Like ago, we had SharePoint.
It was a Microsoft product.
Again, really bloated and annoying.
Notion is exceptional.
For creating an externalized business
mind that is searchable across all
information in the business, customizable,
you really start with a blank slate.
You can do anything you want,
create any database you want.
You don't have to be tech savvy.
Now, you can ask the AI to do it for you,
and it will and inter linkable so you
can at reply, team members, client pages,
transactions, everything's customizable,
inter linkable for that reason.
I think it's easier to work with a team.
Yes, they're custom agents in
notion and some people are that
it's gonna be too expensive and
notions, token cost seems high, but
Travis: But if you have money,
Jenny: mind, let's say you
Travis: you have
Jenny: and you
Travis: and you can import it,
Jenny: you
Travis: allow you to import
from your stack as well.
Jenny: It's
Travis: it's just so
Jenny: for
Travis: sharing, collaboration, and
Jenny: client facing pages and.
Seeing your business in front of you, and
Travis: especially.
Jenny: team members to do the same.
And I run my whole personal
life in notion too, and my
Travis: And my colleague
Jenny: Sherwood and I,
Travis: and I who created a time operat
Jenny: Just so
Travis: just so people,
Jenny: to start from scratch
Travis: because otherwise
Jenny: at a blank page
in a blinking cursor.
I
Travis: I think comes down to,
Jenny: I
Travis: I just learned, I knew
Jenny: WY week, what
you see is what you get.
But today I've
Travis: I.
Jenny: learned what gooey stands
for, which is graphic user interface,
as in notion is the gooey wy wake.
Like you see it, it's in
front of you, it exists.
Whereas I feel when you're using Claude
desktop, yes, there's a bunch of markdown
files and sure you can have obsidian up.
So you could easily click through
and view them, but it'd be very
overwhelming for a team member.
And I find that despite my best
efforts, my markdown files are still
all over the place in my Linked
AI folder from Claude Desktop.
Whereas in notion, I'm much more
intentional about where things
Travis: Go.
Jenny: and again, now the AI
can find anything you want.
So it's
Travis: So it's so powerful.
Jenny: I think my
Travis: My biggest
Jenny: I'm not
Travis: not.
Jenny: like, I'm not trying to
sell Notion, but I can share
what it did for me was that.
Instead of having to search for
information about my business
and not knowing, is it in Slack?
Is it in a Google Doc?
Google Sheets in an Airtable?
Is it in here?
Is it there?
No.
There's only one place to search, and
that makes search actually functional
as opposed to wasting your time, unable
to retrieve the information you need
or even search for it because it's
spread across 12 software systems or 20.
Travis: Yeah, exactly.
And I think, I think that's also
where, you know, as I, as I am helping
companies prepare to layer AI on
because I think that's something that
they're not really thinking about
is how your processes your data.
Uh, need, your data needs to be clean.
Your processes need to be efficient,
optimized, your systems in place
and your, your documentation.
I, I think is, it's something that
I think a lot of companies have
overlooked or it takes too much
time and they haven't invested as
much time in documentation or proper
documentation, and I think that's gonna.
Come back to bite them.
And I know, I mean, I'm one of 'em be
I, it's, I think it's my A DHD because
I've just always been awful at that.
It's in my head and that's my superpower.
I can keep stuff in my head, but
then I can't hire anybody because
they don't have access to my head.
Right.
And so I think a critical,
critical part is.
Having that documentation in something
like Notion, that's where I've
started building my documentation.
I've used Notion off and on and,
and I think it's been too much of
a blank slate for me to come in and
be like, Ugh, this is overwhelming.
I'll, I'll do something else.
Right.
But I think you had a workshop back
in December maybe that I joined,
and that got me back into notion
and that was the nudge I needed.
And I'm glad because I hadn't quite
really got into the agen side of
things as deeply as I am now and
starting to put documentation in there.
It made that transition so
much easier because I had, I
have a client who sends me.
Uh, you know, his, the sales team
will create lists from ZoomInfo
every, every other week, and then I
put them into, to HubSpot for them.
But I have to do a lot of cleanup.
I have to add columns and do
the stuff, and it's a time suck
and it's not that complicated.
And so I started to create an SOP to
hire someone to then do this for me.
And then I realized the
instructions are there.
If I could.
I have instructions for
a person to do this.
These instructions would work for
Manus, which is what I used for that.
And so I had the spreadsheet in a
Google sheet and I had a link to the
notion page and I just said, Hey,
go follow these instructions and
take this Google sheet and fix it
and get it ready for me to import.
And it, it took something that
was taking me 30 minutes to do
down to like two minutes and.
Now the client has started to just
add new tabs to that Google sheet, and
now I've put an agent in Manus saying,
monitor the sheet and if a new tab
is added, automatically clean it up
and then let me know that you did it.
And so that another step, right?
'Cause like you mentioned, if you have to
do something more than once, automate it.
And so that's what I, I did.
So I think that having that
documentation is gonna be critical.
Jenny: And there's a couple
Travis: More
Jenny: I love how you have the
agent set up now a couple more
Travis: ways.
Jenny: It could be even easier for
you or anyone in that position where
let's say you do, I call it a manager
manual, but it's essentially SOPs.
So now you can create an onboarding
agent who helps onboard in Notion.
They also have just AI chat in
the bottom right hand corner.
So any page you're on, you can with ai.
It's not an agent, but it can answer
questions and do things on those pages.
So
Travis: So you.
Jenny: an agent where anytime we ask
a question in the chat, in the manager
manual, and an SOP does not exist,
interview me to help me create one.
And so that it knows it's either answering
the person's question or it isn't.
And if it isn't, it's helping create the
Travis: That
Jenny: and it's
Travis: taking the responsibility
Jenny: get to then be
in the passenger seat on
Travis: on that.
Still tell
Jenny: know.
I say in free time, every
question lives three lives.
A question that a team member
asks should never just.
Fall by the wayside.
That's the first life, the
time someone asks a question.
Second life is then it.
If it
Travis: It doesn't exist.
Jenny: goes into your documentation.
And the
Travis: And the third, the question.
Jenny: is, does it also need to be
posted on a customer facing resource?
And then the course you
mentioned is the Create Your
Idea Collection Systems course.
This is almost like an entry into
notion, and I love hearing that.
It got you back into it.
But people often save ideas and
Travis: Articles
Jenny: and inspiration all over the place.
It's in their email inbox,
it's in their notes app.
It's scattered everywhere.
It's on pieces of
Travis: paper.
Jenny: So the
Travis: So the, there is
Jenny: one
Travis: one database notion.
Jenny: your collection bucket, and that
every image, thought, idea, whatever it
is, article using the Web Clipper, it
all goes into the same place now with ai.
You could, you can select, say any
card in this database that doesn't have
topics, go ahead and fill in the topics.
And there's like smart AI
generation or bulk processing.
I've now given it like 10 snippets
at once and I say, can you
create cards for these 10 quotes?
Like it even
Travis: Even
Jenny: the
Travis: the,
Jenny: not even
Travis: even
Jenny: The agent for the idea
Travis: for the idea would
be once a week you summarize
Jenny: I've saved?
And give me a one
Travis: one paragraph summary
Jenny: a link to the full card.
You could also bring in your
content calendar, so you
Travis: could.
Jenny: and knowing, you know, you teach
a context about a newsletter that you
write and you say, every Thursday, at
Travis: at
Jenny: any
Travis: many articles I've,
Jenny: since the
Travis: last time you ran a
Jenny: Give me a
Travis: summary and make a recommendation.
Jenny: are
Travis: What are three things
Jenny: include in my next newsletter?
personally don't use AI to write.
I think it's a brilliant
editor, You could, if
Travis: could.
Jenny: to feed it your voice
documents or previous, you can
Travis: You,
Jenny: crawl a blog that you
Travis: you have say, what are
Jenny: What are my
Travis: guidelines?
Jenny: Well, another
Travis: Another thing I.
Jenny: it helps me draft a client
email, 'cause I do use it for some
professional email drafting, day-to-day
stuff, just high stakes contract, things
that I'm nervous about, will give it to
Travis: It
Jenny: I don't
Travis: if I don't like it.
If I do like it,
Jenny: do like it,
Travis: I in
Jenny: paste in what
Travis: what I,
Jenny: sent and I'll say.
Compare your draft to what I
Travis: I actually.
Jenny: and extract rules that
you can to the style guide for
how I write, how I communicate.
So I think part of this is.
Leaning on your feedback skills.
These agents are not
perfect at their first run.
They can do so much, but you do need to
be patient and commit to giving feedback.
I even create a little status field
in my hub where all my agents send
various briefs and reports and the
status says agent needs fixing.
And there's a little notes field where
I make a note of what I wanna fix.
'cause I'm sometimes I'm on the go and
I can't just make the fixes right there.
You can't do it on mobile yet.
I'm sure that will change, like the
agent's gonna need fixing for the first
few times it runs and just expect that.
Travis: Yeah, absolutely.
Yeah.
And I've, I've done similar, right?
I, I don't use it for, for my writing.
I've thought about using it for like
newsletters for my nonprofit where it
doesn't really need to be me writing.
And it could have, could be somebody I
hire, but I don't have to hire them now.
Right.
To just kind of write
about some basic stuff.
And I took my book and dumped
it in and to give it, you
know, 250 pages of how I write.
And, and that book was really
written how I talk anyway.
So it's a pretty good, uh,
example for it to pull from.
But it still will use a lot
of things like terms that.
Or, or widely used that I don't like.
And so I'll have to say, don't
ever use that word again.
I don't, I will never use that word.
But, but yeah, a lot of coaching.
So
Jenny: I have that file too.
It's called Words I Hate.
Travis: yeah.
Jenny: And then if you go to tropes, fyi.
A author created a tropes markdown
file where you can just download his AI
tropes document, it's markdown, and then
upload that into your, your tool and, and
just say, please avoid these AI tropes.
And also, yeah, I said it'll say
something like, it's a solve,
you know, using solve as a noun.
I'm like, no, solve
Travis: Yeah,
Jenny: Like, I hate that
Travis: yeah,
Jenny: use it
Travis: yeah, yeah,
Jenny: have a words I
hate marked on vile that
Travis: yeah.
Nice.
I'll have to do that because I have
a lot of those words working in.
Jenny: on the contrary, if people
send you nice kind things about
you or your business, I call those
keepers, and I've labeled those
in my Gmail for 20 years longer.
I also have a notion, a database
of when people say nice things
about a product or a service.
And I got this idea from
Jeremy Schiff Fling.
He wrote a book called Unbreakable
or Unstoppable, sorry, Jeremy.
It's really good.
It's about how to navigate
your career in the age of ai.
Anyway, it's
Travis: it's suggestion, but I also
Jenny: say,
Travis: say.
Jenny: all these keepers and surface
the key themes and cite your sources.
Like what are the key themes of what
people thank me for or say that I'm,
superpowers are and provide three to
five quotes for each of those strengths
and cite the source link back to
the original card that it came from.
That was a really powerful exercise
to get to know side of myself that
maybe I couldn't have put words to
Travis: Mm-hmm.
Jenny: that way.
Travis: Yeah, absolutely.
I love that example.
So I know we're coming up on, on time
and so I've got one question and,
and my 3-year-old probably coming
in is also that signal what buddy
Jenny: a cutie.
See free time.
It's like, so we can actually
go just live our lives.
Travis: I know well.
Jenny: will keep interviewing me in the
Travis: This is, yeah, exactly.
Exactly.
That's your elevator.
Oh, I love it, buddy.
Jenny: Hi,
Travis: I'm sick.
Do, can you say hi real quick?
Say hi.
Can you wave?
Can you wave?
Okay.
All right.
Can you, can you go out,
go watch super kitties for.
Five more minutes, I'll come get you.
And I You want me to keep this?
Yeah.
Awesome.
Thank you buddy.
But as a closing.
Well, and this is the thing I have
this, I had this closing question
and we already answered it.
And so my, my closing question will
be kinda outside of what we may have
talked about, is there anything that
we didn't mention that you think is
super important, especially for, uh,
business owners, founders to know?
Before jumping into ai.
Jenny: I guess what I would say,
you might've heard this in my
intro to AI workshop agent ai.
Don't let it intimidate you because
now in your natural language, it can
literally tutor you at every step.
And I think that mid-career
professionals and business
owners, so much going for you.
You don't have to be a
software engineer anymore.
And that's new.
That's as of 2026.
Now, if you're a good people
manager and delegator.
your doorway in.
If you are a good problem
solver, that's your doorway in.
If you run a business, you're
an entrepreneur, you're used
to building things from zero
to one, that's your doorway in.
If you're really opinionated
about what you like and don't
like, that's your doorway.
If you're simply curious, you're
just a curious person and you love
to learn, that's your doorway in.
You only need one of these doorways.
on that and don't worry about the rest.
And you're not behind.
You're actually, we're
at the front of the wave.
And it will tell you if, if you get
stuck, if Claude code tells you you need
to open terminal and copy paste this
and you don't know what terminal is,
you can literally say what is terminal?
then it says, oh, just search and
open it and then paste the code.
And you're like, where?
And it will say, oh, that
little blinking rectangle.
I mean, so that's how Let it tutor
you on anything you feel stuck
Travis: Mm-hmm.
Jenny: Don't sit it out.
Travis: Yeah.
Jenny: sit it out.
You have lots of doorways
in and you only need one.
Travis: Yeah.
Yeah, absolutely.
And and yeah, the nice thing about Claude
Oth, others might do this, but it can
actually look at screenshots and know
what's in an image, which is crazy.
And I actually had it walk me through
building a make automation and
injecting, uh, using Claude's API,
to have things run through a prompt.
And I would screenshot where I
was and it ask what do I do now?
What do I put in these?
Empty boxes, right?
And, and if there was an
error, I'd screenshot the error
and say, what's this mean?
How do I fix this?
And it just walked me through
the whole thing like that.
So, so yeah, it, it will guide
you and it can teach you a lot,
Jenny: And I just wanna say,
welcome back to the pod I'm.
So happy you're doing this again.
You're an amazing interviewer and
you're genuinely just curious, and
we're both so excited about this stuff.
I know it's gonna carry you, and
it's definitely like riding a bike.
Travis: Mm-hmm.
Jenny: interview conversation
skills went anywhere.
all here right where you left them.
So welcome back and it's
such a joy to be your first
conversation and bringing it back.
Travis: Thanks.
Yeah, I really appreciate that.
And yeah, I was so excited, uh, that you
were able to be my first, first guest and
you might've been one of my last on my one
before I gave it up before, so, exactly.
So, so yeah, thanks a lot for
joining and uh, yeah, we'll
have to do this, uh, again.