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Hello everybody. 
I'm Jonathan Kirschner and this 

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is a podcast about leadership. 
And on this podcast we talk 

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about the skills and mindsets 
required to become not just a 

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regular old leader, but an 
excellent leader. 

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And today we are talking, we're 
taking on a a very important 

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topic, the climb from start up 
to scale up and ultimately the 

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leap to the public markets, the 
IPO. 

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We always typically hear about 
the financial side of an IPO, 

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the bell ringing, the stock 
price, the capital raise, the 

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big party, the confetti. 
What we rarely talk about is the

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human toll and the leadership 
culture required to start a 

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company is often very different 
from the culture required to 

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lead a public organization. 
And so to help us navigate this,

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we have two incredible heavy 
hitters with us today. 

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First, I'm going to go with got 
to get, we got to get a drum 

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roll. 
I'm doing drum roll Gary 

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service. 
So Gary is an operating partner 

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at Insight Partners, which is 
one of the world's largest 

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venture capital and private 
equity firms. 

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So Gary, Gary does not watch 
from the sidelines. 

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Gary's deep in the trenches with
his portfolio companies, and 

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he's helping them navigate the 
messy, complex journey of what 

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we'll call scaling up. 
And he's bringing the unique 

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perspective of seeing this play 
out across not just like one or 

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two, but hundreds of 
organizations knowing exactly 

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where the plot twists are. 
And so it's incredible to have 

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you on the show today, Gary. 
Thank you so much for joining 

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From what looks like New York 
City in the background. 

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Indeed it is. 
Thank you Jonathan. 

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Super excited to talk about one 
of my favorite topics. 

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Awesome. 
OK, and then joining Gary as as 

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though it was wouldn't be 
enough. 

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We have Katherine Williamson. 
It's weird saying Katherine 

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cause Kat, I know you for for 
years. 

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And Kat is currently the VP of 
talent development at Gong. 

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Kat's previously held roles at 
Hashicorp, Pinterest, and other 

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high growth tech firms. 
She's an expert practitioner who

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has lived through the IPO 
transition from the inside and 

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recently actually collaborated 
with us. 

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Thank you so much, Kat, for the 
collaboration and partnership on

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the white paper that we wrote 
titled The IPO Evolution, which 

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looks specifically at how talent
and culture needs to mature in 

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order to survive public 
scrutiny. 

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Kat knows exactly what it takes 
to get a leadership bench ready 

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for the big leagues. 
So Gary Cat, welcome to the 

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show. 
This is I'm pumped. 

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I'm going to I'm going to field 
the first question to to Gary. 

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So Gary, you work with so many 
companies at that critical scale

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up phase. 
Is there a specific like 

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inflection point or moment, a 
specific kind of failure where a

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founder realizes like, Oh no, 
like all that's fun dopaminergic

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scrappy chaos that got me here 
is now actually like, hurting 

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us. 
It's getting in our way. 

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Yeah. 
I, I think that's such a great 

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question because as as Cat well 
knows, there is points at which 

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we have discussions just about 
talent in general at these 

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businesses that say this person 
in this role probably is not the

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person that's going to get you 
to the next level. 

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They may be great at this range,
not so much to this next leg of 

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the journey. 
And that goes throughout all the

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growth, not just IPO. 
And I think, you know, as 

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companies are working through 
their scale of journey and 

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they're trying to figure out 
what they need to continue to 

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scale, what happens typically, I
mean, unfortunately is the the 

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KPI start to be telling a 
different story. 

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And that doesn't mean the 
company has lost product market 

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fit. 
It doesn't mean that the 

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business is not a good business,
but we start to see some 

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degradation in the core KPIs. 
Those KPIs can be the rate at 

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which ARR is changing. 
So we were growing at, you know,

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a doubling every year, and now 
that's kind of coming down as 

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the rate of change is going. 
And that may be a lot of 

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numbers, by the way. 
It's not just simply that we 

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might see it in little bits of 
retention issues, which tells 

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you that maybe your onboarding 
isn't great. 

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Maybe you have telemetry data 
that tells you your engineering 

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team is working super hard, but 
people aren't using all the new 

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features that are being 
introduced into your. 

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And so these are just examples 
across any of the functional 

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areas which give you leading 
indicators that something within

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the organization has changed. 
And the solution is not always 

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simple. 
It's not necessarily I need a 

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new person or may not mean that 
you need to change how you've 

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done things and you need someone
in a senior role who is not just

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managing for today, but managing
for what's next. 

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That's, that's really 
interesting. 

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So I can actually, you know, 
being, being a founder and, and 

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CEO of two organizations, air 
analytics and air consulting, 

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Air analytics being 3 year old, 
three years old. 

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So it's really still kind of a, 
a, a baby Air consulting being 

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much more mature. 
But like I, I, I know how 

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amazing it feels to move fast to
like out innovate. 

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It's, it's just, it's a, it's 
pleasure full. 

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It's, it's actually like 
incredibly gratifying to lead 

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through innovation and to always
being like always doing new 

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things. 
And I remember the first time 

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somebody was trying to explain 
to me, I didn't get my MBA. 

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So no, no MBA here, no formal 
training psychologist tried to 

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start a company and, and, and 
barely made it. 

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And, and now here I am right 
when somebody was trying to 

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explain to me what a KPI it was,
I was like that. 

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That is like the most like de 
energizing, like concept means 

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you're going to just sit and 
like measure the same thing, you

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know, like every month and then 
like we're going to look at a 

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report or a dashboard on a 
quarterly basis. 

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And that's what success or 
failure is. 

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It's not like what we innovative
or did we have fun or did we 

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move fast and break things. 
So it's like you're so de 

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energizing. 
I'm curious, you know, from from

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both of you, you know, like, 
like cat you, you being sort of 

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operating internally in an 
organization and helping like 

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leaders at scale develop with, 
with some major implications to 

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culture and, and Gary, you, you 
know, looking at investment 

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choices and and helping founder 
CE OS like let's unpack that 

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concept a little bit like how 
the the the founders, let's 

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start with this. 
The founders become sort of 

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obsessed with just like the, 
the, the, the, the allure of 

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chasing the shiny object, moving
fast and breaking things and 

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sort of resist this like slowing
down and attending to the boring

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stuff like KPIs and OK Rs. 
I can start, but I, but I'm sure

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Gary's got got tons to 
contribute as well. 

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I think so. 
And I, I think at least sort of 

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in some of my experiences, I 
think it's less about like the 

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excitement, but more about the 
perception of slowing down to do

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these things. 
And I think sort of sometimes 

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it's been my job to say we might
need to slow down initially, but

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in in order to scale and in 
order to, you know, ramp fast or

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like get after some of the 
things that you want to do, 

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which might be more exciting for
you in terms of innovation and 

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and growth. 
We need to set these foundations

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so that we don't have to keep 
like reiterating things or 

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duplicating work across the 
system because this person built

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something, we haven't shared it 
centrally. 

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We don't have a central 
ownership. 

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Maybe they leave the company or 
they get bored of it and it goes

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away and somebody else has built
the same thing over here, 

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someone else has built the same.
So there's like a place here 

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which is like sometimes you need
to kind of slow down and get 

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your foundations in order to get
back to doing some of the stuff 

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that you love doing. 
Like once this stuff runs well, 

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then you know, go for it. 
Go innovate. 

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Be excited about those things. 
It makes a ton of sense, but 

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like, do you ever, do you ever 
like meet up with resistance 

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when you're saying to a founder 
or to a leadership team, like, 

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Hey, we need to slow down and 
get our processes right. 

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Or, you know, we need to, you 
know, do some interviews and 

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scope out the right, you know, 
solution here. 

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Like, does that feel like 
bureaucracy or like we're we're 

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we're not what we're like 
slowing ourselves down? 

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Yeah, Yeah, absolutely. 
Yeah. 

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I think that's, that's partly 
our job is to, is to kind of 

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paint the picture of the future 
and really, really get to why 

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this is important, particularly 
if it's a topic that the CEO 

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found. 
I've worked in tech a lot. 

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So a lot of tech CEOs might not 
have had been able to see or had

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experiences where HR ran this 
way, operations ran this way. 

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They've seen Rev OPS working at 
scale. 

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Like I think sometimes it's our 
job to, you know, to educate in 

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that if you, you know, if you 
slow down and create this stuff,

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it doesn't have to seriously 
impact your culture. 

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Your culture can still be 
exciting and innovative and 

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trying new things. 
And there is some benefit to 

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getting some of these pieces in 
place. 

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I think it's a mistake to paint 
the entrepreneur with a single 

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brush stroke. 
And I think that you're going to

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get I, I, I, I talk about four 
archetypes of the entrepreneur. 

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And because they are so 
different that they will respond

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to these things quite 
differently. 

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So archetype #1 especially in, 
in my business is the technical 

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founder. 
And so the technical founder may

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come from an engineering 
background, may come from just 

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much more of, of the the the 
product focus. 

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The second one is going to be 
the go to market founder. 

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And this is a founder that may 
have come up more through sales 

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and found a technical Co 
partner, but you know, they're 

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leading and they're like their 
focus is go to market and 

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selling. 
The third is the finance someone

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who is may have been ACFO or may
just know the the finances of 

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growing businesses and how to do
acquisitions and figure out how 

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to integrate them and how to 
manage all of the numbers. 

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And then the the last one is 
sort of in in by the way, this 

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may not be all MISI. 
You may see overlaps of Navs is 

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what I'll just simply call the 
visionary. 

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And the visionary is, is that 
person that is thinking out to 

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the solutions and is really just
incredible at creatively solving

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for problems. 
And you may have a single one of

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these or some melange of them, 
and they're going to respond to 

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the scaling challenge 
differently. 

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They're going to look for 
different things and they're 

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going to bring different skills 
to it as well. 

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I I love that. 
So I imagine there's not one, 

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you know, silver bullet, like 
there's not one archetype that's

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better than the others. 
Like each one, you know, has its

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own, you know, pluses and 
trade-offs. 

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And I really do appreciate that.
It's not, it's not like every, 

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you know, founder, CEO or 
entrepreneur is, is, is just 

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chasing squirrels, right? 
You, you know, that that product

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person may actually need to 
chase more squirrels, right? 

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They might be like 2 heads down,
focused on their product and not

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looking out enough and 
exercising like creativity or 

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visionary thinking. 
But so, so you know, there's, 

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there's like these, you know, 
like strengths and, and, and 

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trade-offs probably to each 
archetype. 

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So, you know, independent of the
archetype or the melange of, of,

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of, of, of the mix. 
Gary, I'm just curious, like 

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you, you've probably had a 
conversation or two with the 

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founder, you know, that goes 
along the lines of like, you 

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know, what got you here is not 
going to get you there. 

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Can you help us understand? 
Like, what does that look like? 

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And maybe if you had a 
conversation, you don't have to 

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say the name or company or 
anything like that, but you 

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know, what does that 
conversation look like? 

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And, and, and how, and have you 
seen founders take that feedback

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and, and run with it? 
And you know, or, or conversely,

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like they just can't do it. 
They can't. 

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They can't make it happen. 
So when you get to the point of 

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having a conversation with the 
founder about their role or what

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their team looks like or how 
their scaling is going, you 

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know, typically they're in pain 
and and you know, they're in 

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pain, they are expressing their 
pain. 

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It could be that they're working
crazy hours. 

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It could be that they're having 
a hard time delivering on key 

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initiatives like they're in 
pain. 

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And so the, the the discussion 
with ACEO that in some cases 

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it's them, they are not the 
right person to take it to the 

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next level. 
In other cases it could be their

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Co founder who was incredible in
product. 

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But now you need a different 
kind of product organization or 

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any of these combinations. 
And so you need to be in a place

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of first and foremost getting to
the joint recognition that 

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indeed there is an issue. 
Indeed we've isolated where the 

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issue is and we have several 
options of how we could address 

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this. 
You want to empower the CEO and 

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in most cases, even if the CE OS
the issue, they know they're the

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issue. 
They've they're they're very few

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who are not self aware to know 
where their challenges are. 

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And so I think that you know, 
you you can make it into this 

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beautiful drama, but it doesn't 
really have to be a drama. 

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And it doesn't mean that the the
the things that got you here 

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won't get you here in the 
future. 

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Needs to that discussion doesn't
mean need to be a game ender. 

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It can be the beginning of that 
next level of collaboration with

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that founder, which can be 
equally as beneficial. 

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And I'll say one last thing, 
which is, you know, a long time 

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ago, and I'm sure you know, 
Jonathan, you, you say this with

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00:17:05,640 --> 00:17:08,319
some frequency. 
You know, I worked with a coach 

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and, and you know, the, the, the
key focus of that coach was 

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getting me to identify my 
highest and best use. 

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And if you can, if you can focus
on highest and best use of an 

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00:17:21,040 --> 00:17:24,599
individual, then it's a very 
different discussion. 

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Because now you're saying, look 
at all the amazing things you 

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bring. 
Remember I told you the four 

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archetypes? 
Maybe they've been forced to be 

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all four of them and they really
should just be one of them. 

255
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And that may be just a load 
taken off their shoulders. 

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00:17:39,320 --> 00:17:45,520
So in many ways, these aren't 
just, you know, these aren't 

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00:17:45,520 --> 00:17:47,320
just difficult conversations, 
these are coaching 

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00:17:47,320 --> 00:17:50,480
conversations, Gary, that you're
having with the founder. 

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00:17:51,600 --> 00:17:54,760
The board should be a coach. 
If you're going to use a board 

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00:17:55,040 --> 00:18:01,000
in the best possible way, the 
best possible way is not to like

261
00:18:01,080 --> 00:18:06,120
use your decks to March them 
through all the slides and show 

262
00:18:06,120 --> 00:18:09,000
them the performance that you 
could have emailed them and it. 

263
00:18:09,240 --> 00:18:12,640
And if they're doing their job, 
they're reading what you want to

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00:18:12,640 --> 00:18:18,040
use the board is as a coach, as 
an advisor, as having more data 

265
00:18:18,040 --> 00:18:22,000
points than you do to be able 
to, to give you recommendations.

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I love it. 
I love, I love orienting to the 

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00:18:27,120 --> 00:18:29,680
I mean, a board is scary. 
You know, I've been just again, 

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00:18:29,880 --> 00:18:33,240
talking from, you know, the, 
the, the shoes of, of, of a 

269
00:18:33,240 --> 00:18:35,600
founder. 
It's it's like an intimidating 

270
00:18:35,920 --> 00:18:39,200
thing to have a board and to be 
coming in and reporting to the 

271
00:18:39,200 --> 00:18:43,600
board, but that that shift in 
mindset and orienting to the 

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00:18:43,600 --> 00:18:48,400
board as as sort of a a. 
You got to move beyond it being 

273
00:18:48,400 --> 00:18:55,320
a report card and and move it to
being everyone is on the has the

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00:18:55,320 --> 00:18:58,360
same goal to make this business 
successful. 

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Let's all get together and have 
that discussion and I'm going to

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00:19:01,360 --> 00:19:05,280
be super transparent about where
things are going well and where 

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00:19:05,280 --> 00:19:08,440
they're not. 
That's where many founders go 

278
00:19:09,200 --> 00:19:14,320
awry is they try to couch what 
they're saying and put it in a 

279
00:19:14,720 --> 00:19:19,360
in a language there versus 
taking ownership, saying I tried

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00:19:19,360 --> 00:19:22,280
this thing, it didn't work. 
Here's where I think the next 

281
00:19:22,280 --> 00:19:24,880
direction is. 
So that that transparency, that 

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00:19:24,880 --> 00:19:28,840
candor and us all, we're all on 
the same team here. 

283
00:19:29,360 --> 00:19:32,880
This isn't just like a, a 
quarterly report card in front 

284
00:19:32,880 --> 00:19:38,200
of a bunch of people where I 
need to, you know, put spin on 

285
00:19:38,200 --> 00:19:43,080
every message and slide. 
This is for us to come together 

286
00:19:43,080 --> 00:19:45,440
to move the needle forward 
together. 

287
00:19:45,440 --> 00:19:49,080
That's that's actually really 
valuable for the founders 

288
00:19:49,080 --> 00:19:51,760
listening to this podcast, but 
also I think for board members 

289
00:19:51,760 --> 00:19:54,200
as well, because I think board 
members sometimes do come to 

290
00:19:54,640 --> 00:19:59,560
these meetings approaching it 
like a, like a, a scorecard 

291
00:20:00,640 --> 00:20:06,360
report card activity. 
So I really appreciate that cat.

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00:20:06,360 --> 00:20:09,160
I you know. 
Of course, I read the white 

293
00:20:09,160 --> 00:20:13,800
paper that that you contributed 
so heavily to before this 

294
00:20:14,640 --> 00:20:18,040
podcast to freshen up. 
I was shocked by this statistic 

295
00:20:18,040 --> 00:20:25,320
that basically 60% of founders 
are no longer CEO by the time of

296
00:20:25,320 --> 00:20:31,840
IPOII mean, I guess I'm just 
curious, you know, for, for all 

297
00:20:31,840 --> 00:20:34,680
the founders listening and, and,
and those who are fascinated 

298
00:20:34,680 --> 00:20:38,480
with, you know, scale up 
ecosystems, like what's the 

299
00:20:38,480 --> 00:20:43,600
shift in mindset that you've 
seen that is needed by the 

300
00:20:43,600 --> 00:20:50,320
founder in order to be part of 
like that 40% that that are, you

301
00:20:50,320 --> 00:20:56,720
know, surviving? 
Yeah, I, you know, I think, you 

302
00:20:56,720 --> 00:20:58,320
know, and I think we were 
talking about this before. 

303
00:20:58,320 --> 00:21:00,600
It's, it's really quite a 
different job. 

304
00:21:01,160 --> 00:21:06,280
I think it is that shift from, I
think we say it in the white 

305
00:21:06,280 --> 00:21:12,240
paper, you know, from sort of 
chaos to organization and maybe 

306
00:21:12,240 --> 00:21:17,640
from sort of short term mindset 
to more of a sort of structured 

307
00:21:17,640 --> 00:21:21,840
longer term focus. 
I think that's that's really the

308
00:21:21,840 --> 00:21:25,200
big shift, which can feel 
honestly like a completely new 

309
00:21:25,200 --> 00:21:30,840
job sometimes. 
And I think that that is sort of

310
00:21:30,840 --> 00:21:33,080
the risk and there's lots of 
different pieces to it. 

311
00:21:33,080 --> 00:21:37,720
But to Gary's point, like if 
there was things that you loved 

312
00:21:37,720 --> 00:21:41,080
doing, you loved being, you 
know, if you're maybe the 

313
00:21:41,080 --> 00:21:44,240
engineering archetype, like you 
love being in there solving the 

314
00:21:44,240 --> 00:21:47,880
problem, you know, sitting with 
teams, actually doing the work. 

315
00:21:48,160 --> 00:21:52,880
And now suddenly your role is 
much more numbers and reporting 

316
00:21:52,880 --> 00:21:55,760
out and being, you know, 
questions and possibly judged in

317
00:21:55,760 --> 00:21:59,080
a way on on your success in a 
way that you haven't 

318
00:21:59,080 --> 00:22:02,280
experienced, you know, in, in 
the times that you're really 

319
00:22:02,280 --> 00:22:06,000
enjoying work. 
It can, you know, it can be sort

320
00:22:06,000 --> 00:22:08,840
of a lonely job and suddenly 
you're not doing any of the cool

321
00:22:08,840 --> 00:22:12,360
stuff you wanted to do. 
And so sort of I think that's 

322
00:22:12,480 --> 00:22:14,560
that's one of the biggest 
challenges I think. 

323
00:22:15,080 --> 00:22:16,640
Yeah. 
I mean, when I, I, I, I work 

324
00:22:16,640 --> 00:22:22,440
with a, a, a founder CEO that 
IPO and like one of the biggest 

325
00:22:23,800 --> 00:22:29,280
like disenchanting surprises 
was, you know, all of a sudden 

326
00:22:29,320 --> 00:22:33,400
you've got to now like report on
a quarterly basis to the public 

327
00:22:33,400 --> 00:22:36,720
and 1 penny off. 
Or even now, you know, with the 

328
00:22:36,720 --> 00:22:39,720
pressure that in the markets, 
like if you just meet 

329
00:22:39,720 --> 00:22:43,920
expectations or, or maybe you're
like exceeding expectations, but

330
00:22:43,920 --> 00:22:47,440
not exceeding enough for your 
forward guidance wasn't strong 

331
00:22:47,440 --> 00:22:51,720
enough that it could just like 
send you back 20% like like 

332
00:22:51,720 --> 00:22:53,520
that. 
And then all of a sudden 

333
00:22:53,520 --> 00:22:59,720
everybody's like all of a sudden
short term focused and and then 

334
00:22:59,720 --> 00:23:02,520
it you know, you get to the next
quarter, maybe you, you, you, 

335
00:23:02,600 --> 00:23:05,840
you, you crushed it. 
You tell a better narrative. 

336
00:23:06,400 --> 00:23:10,960
The stock goes up, but then the 
next quarter down it it the the 

337
00:23:11,040 --> 00:23:16,360
the cycle and the the volatility
of this can create this like 

338
00:23:16,360 --> 00:23:21,200
very like short term thinking. 
And now all of a sudden like 

339
00:23:21,200 --> 00:23:24,760
this expansive, especially for 
the visionary archetype. 

340
00:23:24,760 --> 00:23:29,760
I imagine this would be like 
particularly hard for a lot of 

341
00:23:29,760 --> 00:23:35,480
that spark gets diminished. 
And I'm just curious from both 

342
00:23:35,480 --> 00:23:40,600
of you like, how do we mitigate,
you know, that risk, that risk 

343
00:23:40,880 --> 00:23:45,240
of becoming as maybe like Jeff 
Bezos and the Amazonians might 

344
00:23:45,240 --> 00:23:47,800
say becoming like a day 2 
company, right? 

345
00:23:47,800 --> 00:23:52,560
How do we mitigate the risk of 
becoming a Day 2 company where 

346
00:23:52,560 --> 00:23:59,640
that initial vibe and and that 
energy is is diminished? 

347
00:24:02,120 --> 00:24:09,120
Well, so I, I'm not sure the 
goal is to preserve the vibe 

348
00:24:10,240 --> 00:24:16,920
and, and, and, and what I mean 
by that is the, the concept of, 

349
00:24:17,280 --> 00:24:24,480
of a company pre IPO and a 
company post IPO cannot by his 

350
00:24:24,480 --> 00:24:28,360
very nature be the same thing. 
Now you and I can talk about 

351
00:24:28,360 --> 00:24:35,120
culture and preserving core 
tenants of our culture, but you 

352
00:24:35,120 --> 00:24:41,800
literally if you're a strong 
leader of a IPOA company that 

353
00:24:41,800 --> 00:24:47,560
IPOs, you need to be the kind of
leader that says we were an 

354
00:24:47,560 --> 00:24:54,240
amazing startup, we had a 
journey, we grew, we created and

355
00:24:54,240 --> 00:24:59,280
our job isn't over. 
We are ready to move to our next

356
00:24:59,600 --> 00:25:05,520
level of growth, our next arc. 
And it won't be the same as our 

357
00:25:05,520 --> 00:25:11,120
previous arc, but it can't, it 
can be just as rewarding, but in

358
00:25:11,120 --> 00:25:16,880
different ways. 
And that message to your 

359
00:25:16,880 --> 00:25:21,280
employee base, because one of 
the the things that's really 

360
00:25:21,280 --> 00:25:26,120
hard for companies is actually 
retaining those employees post 

361
00:25:26,120 --> 00:25:29,240
IPO. 
Cat knows this more so than I 

362
00:25:29,240 --> 00:25:32,280
do. 
And that, you know, you need to 

363
00:25:32,320 --> 00:25:35,880
it. 
And it's not simply money now, 

364
00:25:36,000 --> 00:25:41,520
because some of them may have 
done incredibly well in AIPO and

365
00:25:41,520 --> 00:25:48,840
now you need to reinvigorate the
organization with new incentives

366
00:25:49,000 --> 00:25:53,760
and new excitement. 
That was not what people were 

367
00:25:53,760 --> 00:25:55,880
there originally. 
And there's nothing wrong with 

368
00:25:55,880 --> 00:25:57,520
that. 
And that's sort of my message 

369
00:25:57,880 --> 00:25:59,880
that there's nothing wrong with 
that. 

370
00:26:01,240 --> 00:26:05,600
Yeah, and and spot on. 
And, and what I'd add is like, I

371
00:26:05,600 --> 00:26:09,360
think sometimes where things lag
or sometimes where you can get 

372
00:26:09,360 --> 00:26:13,400
this kind of disrupted vibe or, 
you know, maybe even culture is 

373
00:26:13,400 --> 00:26:17,640
when you have a set of leaders 
or a CEO, founder or somebody 

374
00:26:17,880 --> 00:26:22,360
who like won't make that shift 
says, no, we have to keep 

375
00:26:22,360 --> 00:26:25,720
everything exactly as it was 
when we're a private company. 

376
00:26:26,080 --> 00:26:30,240
But also, you know, that's not 
the reality everybody's living 

377
00:26:30,240 --> 00:26:32,600
in. 
And so employees get this weird 

378
00:26:32,600 --> 00:26:35,400
mix of, no, we're still the 
same. 

379
00:26:35,400 --> 00:26:38,840
We're still, you know, cool and 
innovative, but what they're 

380
00:26:38,840 --> 00:26:42,560
seeing in reality is something 
that that looks and feels 

381
00:26:42,560 --> 00:26:44,920
different. 
So you have this kind of push 

382
00:26:44,920 --> 00:26:47,080
and pull moment. 
And I think that's one of them. 

383
00:26:47,080 --> 00:26:51,040
The mistakes as a, you know, at 
least you sort of see out there 

384
00:26:51,040 --> 00:26:55,320
around, you know, the 60% is 
maybe the not recognizing and 

385
00:26:55,320 --> 00:26:57,240
making that shift when they need
to. 

386
00:26:57,240 --> 00:27:00,760
And then like Gary just said, 
reinvigorating towards it. 

387
00:27:01,880 --> 00:27:05,800
Success is is, you know, a huge 
motivator. 

388
00:27:06,120 --> 00:27:09,120
Sometimes the success looks 
different in startup than it 

389
00:27:09,120 --> 00:27:11,600
might do in a scaling public 
company. 

390
00:27:12,000 --> 00:27:15,960
But success is success. 
And so how do you start talking 

391
00:27:15,960 --> 00:27:20,400
about, you know, the public 
company's success in a way 

392
00:27:20,400 --> 00:27:23,240
that's just as invigorating as 
maybe it was in the past? 

393
00:27:23,920 --> 00:27:26,960
And I and I would say like it's 
really interesting people talk 

394
00:27:26,960 --> 00:27:31,840
about IP OS being milestones. 
Now a milestone just to keep 

395
00:27:31,840 --> 00:27:35,920
everyone on using our words 
correctly is not an end point. 

396
00:27:36,880 --> 00:27:42,240
It's a point on the journey. 
And so when you think about the 

397
00:27:42,240 --> 00:27:46,760
milestone of IPO hell, we're 
just getting started. 

398
00:27:47,440 --> 00:27:51,640
And so I think it's really 
important for folks to think 

399
00:27:51,640 --> 00:27:56,120
about this in the, in the, the 
journey that this organization 

400
00:27:56,120 --> 00:27:57,920
is on. 
And while this is an important 

401
00:27:58,040 --> 00:28:01,160
milestone, it is certainly not 
the end point. 

402
00:28:01,880 --> 00:28:05,160
That's really important. 
I'm wondering going back to a 

403
00:28:05,160 --> 00:28:08,560
point you may go, which I I 
found to be like, you know, 

404
00:28:08,760 --> 00:28:14,360
personally resonant like we're 
not solving for vibe. 

405
00:28:15,320 --> 00:28:23,440
So many founders can can get 
sort of caught in the trap where

406
00:28:23,440 --> 00:28:28,160
they're solving for vibe and 
they're sort of like clinging to

407
00:28:29,080 --> 00:28:33,160
that that, you know, kind of 
like founder energy. 

408
00:28:34,720 --> 00:28:39,480
And I'm just curious, like, can 
that be a derailleur, you know, 

409
00:28:39,480 --> 00:28:43,640
is in, in some ways, have you 
seen this like where, where 

410
00:28:43,760 --> 00:28:51,800
founders are doing that in some 
way to resist the natural 

411
00:28:51,880 --> 00:28:56,080
maturation to the next level? 
You know, could it be some kind 

412
00:28:56,080 --> 00:29:02,120
of like unconscious change 
resistance, you know, and from, 

413
00:29:02,120 --> 00:29:04,360
from, from actually growing up, 
right? 

414
00:29:04,360 --> 00:29:05,680
Like, I don't want to grow up. 
It's scary. 

415
00:29:05,680 --> 00:29:08,320
It's scary to be an adult. 
It's scary to be, you know, with

416
00:29:08,320 --> 00:29:10,400
the big boys. 
Like, I want to go back to the 

417
00:29:10,400 --> 00:29:12,920
to the playground. 
I'm just curious, you know, I'm,

418
00:29:12,920 --> 00:29:14,920
I'm playing with this idea. 
Yeah, no, no, no. 

419
00:29:14,920 --> 00:29:19,200
There are plenty of founders who
find themselves in the 

420
00:29:19,200 --> 00:29:25,400
predicament that they solved a 
really important problem at one 

421
00:29:25,400 --> 00:29:31,880
point and the world is changing 
super quickly. 

422
00:29:32,800 --> 00:29:37,520
And the solution to that problem
is not what they came up with or

423
00:29:37,520 --> 00:29:41,600
the market their product is 
targeted to is no longer the 

424
00:29:41,600 --> 00:29:45,560
right market. 
And in and in so doing this, 

425
00:29:45,560 --> 00:29:50,840
there's this massive amount of 
like I, I was giving a talk last

426
00:29:50,840 --> 00:29:53,960
week and I was talking about AI 
transformation. 

427
00:29:54,000 --> 00:29:59,240
And I, I said transformation 
used to be a project, like it 

428
00:29:59,240 --> 00:30:02,120
had a beginning and end. 
We're going to do project Opus 

429
00:30:02,360 --> 00:30:04,640
and project Opus is going to 
come from here to here. 

430
00:30:04,640 --> 00:30:07,040
And when all of a sudden 
magically we'll be in the cloud 

431
00:30:07,040 --> 00:30:11,280
or magically, you know, we'll be
doing this with, with AI and the

432
00:30:11,280 --> 00:30:15,440
world we're in, we're in 
constant transformation. 

433
00:30:15,920 --> 00:30:23,120
And so those founders who find 
it hard to create the culture of

434
00:30:23,120 --> 00:30:28,720
reinvention and constantly 
pushing the boundaries for 

435
00:30:28,720 --> 00:30:33,760
themselves personally as well As
for their teams are going to 

436
00:30:33,760 --> 00:30:36,000
struggle. 
And this has nothing to do with 

437
00:30:36,000 --> 00:30:38,840
IPO. 
This is just leadership in 

438
00:30:38,840 --> 00:30:43,520
general and what it's going to 
take to be successful in a world

439
00:30:43,520 --> 00:30:47,160
where the idea that we're 
transforming our business is 

440
00:30:47,160 --> 00:30:49,600
never done. 
Right. 

441
00:30:49,600 --> 00:30:53,040
It's not, it's, it's, it's not 
a, you know, transformation 

442
00:30:53,040 --> 00:30:57,080
where we start here and and here
and then we're done and, and now

443
00:30:57,080 --> 00:30:59,120
we're, we're there and maybe 
there's another transformation a

444
00:30:59,120 --> 00:31:02,040
few years later. 
We're we're in constant and 

445
00:31:02,040 --> 00:31:04,680
continuous change. 
So what I'm hearing from you is 

446
00:31:04,680 --> 00:31:07,400
that right again, put, put IPO, 
scale up, start up. 

447
00:31:07,680 --> 00:31:13,360
All that aside, like table 
stakes, to be a leader today is 

448
00:31:13,360 --> 00:31:16,680
like you said, Gary, to be in 
like creating a cultural 

449
00:31:16,680 --> 00:31:21,920
constant reinvention, which is 
that's hard. 

450
00:31:22,120 --> 00:31:25,280
If you're not disrupting 
yourself, if you're not 

451
00:31:25,280 --> 00:31:29,160
disrupting yourself, there are 
many little AI native companies 

452
00:31:29,520 --> 00:31:33,520
and competitors and the folks 
that used to not be competitors 

453
00:31:33,520 --> 00:31:35,560
say, what the hell? 
This looks like a juicy market. 

454
00:31:35,560 --> 00:31:38,200
I'm going to go into this market
like we're in a hyper 

455
00:31:38,200 --> 00:31:41,920
competitive world. 
And so if you are not like 

456
00:31:41,920 --> 00:31:46,320
thinking of it in this world and
I'm not picking on Gong in any 

457
00:31:46,320 --> 00:31:48,320
way. 
I'm just saying Gong did this 

458
00:31:48,320 --> 00:31:50,720
one great little thing. 
It recorded calls. 

459
00:31:50,720 --> 00:31:53,200
Wasn't that amazing? 
Well, if that's the only thing 

460
00:31:53,200 --> 00:31:56,680
it continued to do today, no one
would care. 

461
00:31:58,200 --> 00:32:02,440
And so as you sort of think 
about like just what is going on

462
00:32:02,440 --> 00:32:08,280
in a regular cadence of Business
Today, the the great leader is, 

463
00:32:08,360 --> 00:32:13,760
is the leader that is paranoid. 
Paranoia is actually a powerful 

464
00:32:13,760 --> 00:32:16,880
tool for a leader. 
Like you need to see all this 

465
00:32:16,880 --> 00:32:19,680
risk and you need to see all 
this change and you need to 

466
00:32:20,000 --> 00:32:23,440
understand like the world is 
changing and I'm not sure where 

467
00:32:23,440 --> 00:32:25,080
it's going. 
And I'm OK with that. 

468
00:32:25,080 --> 00:32:26,720
And I know how to lead through 
that. 

469
00:32:26,800 --> 00:32:30,440
And so I think that you know 
what, what you're left with 

470
00:32:30,440 --> 00:32:36,200
today is a very different kind 
of operating world that every 

471
00:32:36,200 --> 00:32:40,320
leader of every business is 
going to need to, you know, up 

472
00:32:40,320 --> 00:32:44,120
their skills to be successful. 
Even if they've had successful 

473
00:32:44,120 --> 00:32:47,960
exits before, whatever they did 
there probably not going to work

474
00:32:47,960 --> 00:32:50,800
now. 
And so you got to get to that 

475
00:32:50,800 --> 00:32:54,480
level. 
That actually that makes me 

476
00:32:54,480 --> 00:32:59,640
think about like, you know, Kat,
you've been doing this for a 

477
00:32:59,640 --> 00:33:01,680
long time. 
I mean, you, you've led the 

478
00:33:01,680 --> 00:33:04,840
leadership development and 
talent development functions in,

479
00:33:04,840 --> 00:33:09,520
in numerous start up to scale up
organizations. 

480
00:33:10,040 --> 00:33:13,920
And you know, in that capacity, 
like you've got to like decide 

481
00:33:13,920 --> 00:33:18,840
like at this level, we're going 
to focus on these attributes and

482
00:33:18,840 --> 00:33:22,160
competencies and then this level
we're going to focus on these 

483
00:33:22,160 --> 00:33:24,640
leadership skills. 
And at this level of our 

484
00:33:24,640 --> 00:33:26,160
emerging leader, we're going to 
work on these skills. 

485
00:33:26,160 --> 00:33:31,400
It's like a, it's, it's like a 
jigsaw puzzle specific to the 

486
00:33:31,400 --> 00:33:34,760
context of, of being, you know, 
in this in motion from start of 

487
00:33:34,760 --> 00:33:36,920
the scale up. 
And then of course, specific to 

488
00:33:37,160 --> 00:33:39,920
the organization, whether it's 
Hashic or Pinterest gone, 

489
00:33:39,920 --> 00:33:45,080
whatever it is, right? 
I, I'm just curious from, well, 

490
00:33:45,080 --> 00:33:49,400
I got 2 questions. 
Like one help me understand how 

491
00:33:49,760 --> 00:33:58,160
this like how do you get this 
accepted into the system, into a

492
00:33:58,160 --> 00:34:01,600
system that's always like 
working harder than like their 

493
00:34:01,600 --> 00:34:06,120
actual capacity that's always 
under tons of pressure? 

494
00:34:06,400 --> 00:34:09,480
How do you get people to like 
slow down to basically learn 

495
00:34:10,280 --> 00:34:13,199
leadership skills? 
Like I'm wondering, you probably

496
00:34:13,199 --> 00:34:15,280
get a lot of resistance. 
Like no, like we don't have time

497
00:34:15,280 --> 00:34:16,679
for that. 
We don't have budget for that. 

498
00:34:16,679 --> 00:34:19,880
We're we're putting that into, 
you know, our marketing budget, 

499
00:34:19,880 --> 00:34:23,280
like the people figured out 
given this book, you know, like,

500
00:34:23,400 --> 00:34:29,080
so I'm just curious like how 
you, you know, get buy in at the

501
00:34:29,080 --> 00:34:33,639
broadest level of of a start up 
to scale up. 

502
00:34:33,920 --> 00:34:36,920
And then my second question 
really to to to both of you, 

503
00:34:36,920 --> 00:34:40,000
just like thinking about the 
skills we need right now in this

504
00:34:40,000 --> 00:34:42,960
point in time. 
So if we had a magic wand and 

505
00:34:42,960 --> 00:34:46,159
can create like the the ultimate
leadership development 

506
00:34:47,199 --> 00:34:54,239
experience for a, a pre IPO or 
or just recently post IPO 

507
00:34:54,239 --> 00:34:59,720
organization in the year 2026, 
like what would that look like? 

508
00:34:59,720 --> 00:35:03,160
So, so, but let's go to the 
first question for yeah, just 

509
00:35:03,160 --> 00:35:06,920
like table sticks. 
How do you get adoption of 

510
00:35:06,920 --> 00:35:11,080
leadership development and that 
investment of time and budget in

511
00:35:11,080 --> 00:35:14,080
in an organization that's moving
at like 120 miles an hour? 

512
00:35:15,920 --> 00:35:19,040
Yeah, yeah. 
I think, you know, I think as 

513
00:35:19,040 --> 00:35:22,840
the world's changing, you know, 
our development models need to 

514
00:35:22,840 --> 00:35:26,720
change as well. 
You know, I think in the past it

515
00:35:26,720 --> 00:35:29,320
was OK to grab a bunch of 
leaders and take them out of the

516
00:35:29,320 --> 00:35:32,320
business for a week and, you 
know, take them on a track and 

517
00:35:32,320 --> 00:35:35,360
learn team development skills 
and, and things like this. 

518
00:35:36,280 --> 00:35:40,320
And, you know, very common set 
of skills that we're going to 

519
00:35:40,320 --> 00:35:44,040
lead to success as a leader. 
I think that is all kind of out 

520
00:35:44,040 --> 00:35:47,600
the window now. 
I think really, really good 

521
00:35:47,600 --> 00:35:52,720
leadership development is when 
you can sit alongside a leader 

522
00:35:52,920 --> 00:35:57,760
for a period of time and really 
understand what are they doing 

523
00:35:57,760 --> 00:36:01,240
in their business, what are 
their business challenges, How 

524
00:36:01,240 --> 00:36:03,240
is their team around them 
operating? 

525
00:36:04,240 --> 00:36:06,400
How you know, what are some of 
the struggles that they have 

526
00:36:06,400 --> 00:36:12,280
with their particular business 
and then being able to sort of 

527
00:36:12,280 --> 00:36:15,960
OfferUp those little bits of, I 
call it in the flow of work kind

528
00:36:15,960 --> 00:36:20,440
of moments or practice or 
support that helps them get 

529
00:36:20,440 --> 00:36:23,520
their job done. 
And that's, that's really where 

530
00:36:23,520 --> 00:36:26,920
I think leadership development 
is going is around getting much 

531
00:36:26,920 --> 00:36:31,360
closer to the business and to 
the leaders that we're there to 

532
00:36:31,360 --> 00:36:34,880
help develop, understand where 
the business is going. 

533
00:36:34,880 --> 00:36:39,440
Like really put a business lens 
on and then create just little 

534
00:36:39,440 --> 00:36:43,200
moments of support, almost like 
sort of sitting with, with your 

535
00:36:43,200 --> 00:36:47,040
courage to help them get the job
done that they've got in front 

536
00:36:47,040 --> 00:36:49,080
of them. 
But at the same time, keeping an

537
00:36:49,080 --> 00:36:52,480
eye on the future, which is, OK,
you've got a problem today, 

538
00:36:52,600 --> 00:36:55,000
Let's practice a new skill. 
How does that feel? 

539
00:36:55,000 --> 00:36:56,680
What does that look like? 
What's some feedback? 

540
00:36:56,960 --> 00:36:59,240
And then when that challenge 
comes up again, let's practice 

541
00:36:59,240 --> 00:37:03,000
that skill again, building over 
time rather than thinking 

542
00:37:03,000 --> 00:37:05,520
there's sort of a silver bullet.
It's just it's not that way. 

543
00:37:06,560 --> 00:37:09,480
So it's not about, you know, 
carving out the three days and 

544
00:37:09,480 --> 00:37:13,120
going off site to the mountains 
or something like that, that 

545
00:37:13,120 --> 00:37:17,320
that's, I mean, does that work? 
I think it depends on the 

546
00:37:17,320 --> 00:37:20,720
challenge that the, that the 
leader or the leadership team is

547
00:37:20,720 --> 00:37:24,320
facing. 
I am and I don't, you know, I'm 

548
00:37:24,320 --> 00:37:28,840
not saying that sometimes it's, 
it's necessary to take a group 

549
00:37:28,840 --> 00:37:31,880
of leaders, maybe a leadership 
team out of the business for a 

550
00:37:31,880 --> 00:37:36,040
second so they can all figure 
out how do I work together? 

551
00:37:36,440 --> 00:37:39,200
Maybe they have instead of 
conflict that is starting to get

552
00:37:39,200 --> 00:37:40,720
in the way of their decision 
making. 

553
00:37:41,280 --> 00:37:43,400
OK, so it's OK to say, yo, time 
out. 

554
00:37:43,920 --> 00:37:45,560
Let's step away here for a 
second. 

555
00:37:45,600 --> 00:37:49,960
Let's figure out why we keep 
running into conflict here as an

556
00:37:49,960 --> 00:37:53,440
executive team, how that's 
slowing down our decision making

557
00:37:53,680 --> 00:37:57,040
and what impact is that having 
on the business and how do we 

558
00:37:57,040 --> 00:37:59,880
start to get past this so that 
this conflict isn't slowing us 

559
00:37:59,880 --> 00:38:03,440
down anymore? 
And so if that's the problem, I 

560
00:38:03,440 --> 00:38:07,080
might say, yeah, those in the 
moments like little hints and 

561
00:38:07,080 --> 00:38:09,080
tips might not get them over 
this hurdle. 

562
00:38:09,080 --> 00:38:11,400
You might need to pull them out 
and say, hey, we need to really 

563
00:38:11,400 --> 00:38:13,800
fix this and then get them back 
in. 

564
00:38:15,200 --> 00:38:18,560
But that's you being very close 
to the business and starting to 

565
00:38:18,560 --> 00:38:21,640
understand the root cause of how
some of this is happening. 

566
00:38:21,640 --> 00:38:26,440
So in the in that instance, you 
might come in for an hour, see a

567
00:38:26,440 --> 00:38:29,320
meeting, understand decision 
making is the problem, and then 

568
00:38:29,320 --> 00:38:32,400
create an operating process for 
them to start decision making. 

569
00:38:32,720 --> 00:38:36,320
But if the conflict is actually 
the problem there no operating 

570
00:38:36,320 --> 00:38:38,960
model in the world is going to 
help because there's, you know, 

571
00:38:38,960 --> 00:38:41,960
contrarians and things like this
in the group that are that are 

572
00:38:41,960 --> 00:38:45,200
disrupting decision making. 
But that's about getting close 

573
00:38:45,200 --> 00:38:47,920
and then finding the solution 
that meets the need. 

574
00:38:49,520 --> 00:38:52,960
And I and I would, I would add 
Kat on that piece there. 

575
00:38:52,960 --> 00:38:57,120
I think you make some really 
important points here. the IT 

576
00:38:57,120 --> 00:39:02,680
really depends on the problem 
and what is the best tactic to 

577
00:39:02,680 --> 00:39:09,840
have progress. 
So I'm, I guess because I'm so 

578
00:39:10,200 --> 00:39:18,200
over rotated to AI today that I 
believe very strongly that we 

579
00:39:18,200 --> 00:39:22,960
need to work harder to have the 
human to human pieces, which I 

580
00:39:22,960 --> 00:39:25,920
think actually can be more 
impactful. 

581
00:39:26,440 --> 00:39:30,920
And so as you like, look at your
like tool belt of ways that you 

582
00:39:30,920 --> 00:39:36,960
can drive change and impact on 
management teams, on leaders. 

583
00:39:37,440 --> 00:39:41,920
Some of it can be done async and
could be training that you do 

584
00:39:41,920 --> 00:39:50,880
online, but that has limits it I
think if you do it on Prem, 

585
00:39:51,280 --> 00:39:54,440
awesome, maybe that you take 
some time on Prem and do it. 

586
00:39:54,920 --> 00:39:57,920
But when you're on Prem, you 
sort of have all the business 

587
00:39:57,920 --> 00:40:01,120
pressure in the meetings and 
people knocking on the door and 

588
00:40:01,120 --> 00:40:03,880
all those pieces. 
And so you may need to get to 

589
00:40:03,880 --> 00:40:09,040
the mountains just because the 
problem demands dedicated time. 

590
00:40:09,040 --> 00:40:12,520
It can't be just your sort of 
side hustle, so to speak. 

591
00:40:12,840 --> 00:40:15,560
It needs to really have a 
dedicated way. 

592
00:40:15,720 --> 00:40:17,960
To solve for that leadership 
issue. 

593
00:40:18,280 --> 00:40:21,600
So again, you know, I'm, I'm not
trying to overcomplicate it, but

594
00:40:21,600 --> 00:40:25,560
I also don't want us to take, 
you know, a single point of view

595
00:40:25,560 --> 00:40:28,840
because the problems are just so
different as Kat was indicating,

596
00:40:29,120 --> 00:40:33,960
you know, it really depends. 
That's I love that. 

597
00:40:33,960 --> 00:40:37,560
I love the concept of tool belt 
and having like multiple, you 

598
00:40:37,560 --> 00:40:40,680
know, sort of options and tools 
depending on the problem we're 

599
00:40:40,680 --> 00:40:43,840
trying to solve for. 
And, and, and one of those being

600
00:40:43,840 --> 00:40:46,440
the mountains, but others being,
you know, bite sized learning in

601
00:40:46,440 --> 00:40:49,680
the flow of work. 
Fantastic. 

602
00:40:49,680 --> 00:40:53,200
I mean, maybe we could just come
back to this topic of leadership

603
00:40:53,760 --> 00:40:57,480
in, in our current times. 
You know, we're, we're getting 

604
00:40:57,480 --> 00:41:00,720
towards the end of the year, 
about to start a new year 2026. 

605
00:41:01,520 --> 00:41:06,120
We're all experiencing the like 
incredible disruptive power, 

606
00:41:06,360 --> 00:41:09,520
which presents both an 
opportunity and, and, and 

607
00:41:09,520 --> 00:41:14,400
perhaps challenges at the same 
time concurrently with regard to

608
00:41:14,400 --> 00:41:17,640
AI and then and the, the, the 
massive force of innovation that

609
00:41:17,640 --> 00:41:21,960
brings. 
What Yeah, like are the 

610
00:41:21,960 --> 00:41:26,120
leadership skills that leaders 
need to be developing and 

611
00:41:26,120 --> 00:41:30,160
learning the same as they were 
10 years ago? 

612
00:41:30,160 --> 00:41:34,440
Or like, do we need to be 
focused on, you know, some 

613
00:41:34,640 --> 00:41:39,560
distinctive skills or attributes
right now to be successful? 

614
00:41:40,160 --> 00:41:42,960
You know, Gary, I, you 
mentioned, you know, we got to 

615
00:41:42,960 --> 00:41:45,400
be a little more paranoid. 
Like should we be taking like a 

616
00:41:45,400 --> 00:41:49,800
paranoia one O 1 class? 
And I'm just being cheeky with 

617
00:41:49,800 --> 00:41:52,520
you, but curious. 
Like, I don't know, like what 

618
00:41:52,520 --> 00:41:55,520
what, what does a leader need to
do right now to be successful 

619
00:41:56,400 --> 00:42:00,240
to, to, to lead effectively? 
I don't think it's ever been 

620
00:42:00,240 --> 00:42:05,600
harder to be a leader of a 
business than it is today. 

621
00:42:07,440 --> 00:42:10,320
You know, I, I mentioned about 
the transformation, the constant

622
00:42:10,320 --> 00:42:15,800
transformation, managing that is
incredibly challenging. 

623
00:42:16,240 --> 00:42:20,480
And I think, you know, when you 
look at the skill sets that we 

624
00:42:20,480 --> 00:42:26,760
have always valued, whether it 
be communication skills or maybe

625
00:42:26,760 --> 00:42:33,000
it's the the capacity to know 
how to navigate an organization,

626
00:42:33,000 --> 00:42:38,840
or maybe it's the skill of truly
creating leadership and goals 

627
00:42:38,840 --> 00:42:42,480
and, and endpoint, like none of 
those have changed. 

628
00:42:43,560 --> 00:42:49,800
I think what you know, people 
misunderstand about AI today is 

629
00:42:49,840 --> 00:42:53,320
they think that it's a 
technology challenge when in 

630
00:42:53,320 --> 00:42:56,040
reality it's a change management
challenge. 

631
00:42:56,440 --> 00:43:01,640
So all the things that you've 
leveraged in the past to manage 

632
00:43:01,840 --> 00:43:06,800
change need to be in the leaders
tool belt again, like this needs

633
00:43:06,800 --> 00:43:10,240
to you need to be able to have 
the right kind of training and 

634
00:43:10,240 --> 00:43:12,480
you need to create the right 
kinds of incentives. 

635
00:43:12,720 --> 00:43:16,840
And you need to understand that,
you know, the organization is 

636
00:43:16,840 --> 00:43:20,120
probably going to lose some 
people because there's not the 

637
00:43:20,120 --> 00:43:23,800
right fit. 
And, you know, these are not 

638
00:43:23,800 --> 00:43:26,880
I'm, I'm not minimizing these in
any way to say that these are 

639
00:43:26,880 --> 00:43:30,920
easy choices or that these are 
are are decisions that leaders 

640
00:43:30,920 --> 00:43:35,600
take lightly. 
But the in the in a world that 

641
00:43:36,080 --> 00:43:42,880
is accelerating in the pace of 
change, this is not the time to 

642
00:43:43,360 --> 00:43:47,080
just put yourself on the side 
and say, you know, I'm going to 

643
00:43:47,080 --> 00:43:48,160
wait and I'm going to figure it 
out. 

644
00:43:48,160 --> 00:43:49,680
I'm going to see how things 
work. 

645
00:43:50,080 --> 00:43:52,640
Because you may wake up and your
market's gone. 

646
00:43:52,840 --> 00:43:55,840
Your customers are gone. 
Like because someone moved 

647
00:43:55,840 --> 00:43:59,240
quicker, more decisively, 
created the right kind of goals.

648
00:43:59,240 --> 00:44:02,240
And I, and you know, you've 
heard the, you know, move quick 

649
00:44:02,240 --> 00:44:06,360
and break things thing that 
reality has never been more 

650
00:44:06,360 --> 00:44:11,520
important because your customers
are under a different set of 

651
00:44:11,520 --> 00:44:15,280
pressure. 
They're getting the, have you 

652
00:44:15,280 --> 00:44:18,680
adopted AI yet? 
Or where's my ROI from my AI 

653
00:44:19,200 --> 00:44:21,800
initiatives and investment and 
all this? 

654
00:44:21,840 --> 00:44:24,840
And are you someone that can 
help them with that? 

655
00:44:25,000 --> 00:44:28,240
Are you someone that could be 
net plus as long as you're 

656
00:44:28,240 --> 00:44:30,600
transparent? 
You know, I'm never one to 

657
00:44:30,600 --> 00:44:33,040
advocate for like vaporware 
products. 

658
00:44:33,320 --> 00:44:37,920
I'm here to advocate for clear 
direction and road map, like a 

659
00:44:37,920 --> 00:44:40,800
very clear direction that you 
know, I'm going to stick with 

660
00:44:40,800 --> 00:44:45,240
you because you have a place and
you may not have all my 

661
00:44:45,240 --> 00:44:48,320
functionality I need today, but 
you're going to bring that in. 

662
00:44:48,920 --> 00:44:52,200
All good. 
Yeah, I think, I think that's 

663
00:44:52,200 --> 00:44:54,600
always been there and I think 
more so than ever, right. 

664
00:44:54,600 --> 00:44:59,600
If you're sitting in an 
environment where not not only 

665
00:44:59,600 --> 00:45:02,880
are your customers changing and 
moving and getting new things, 

666
00:45:02,880 --> 00:45:06,480
but you and in your flow of 
work, like in your work, you're 

667
00:45:06,480 --> 00:45:09,760
getting asked to, you know, AI 
tools, things like this, get 

668
00:45:09,760 --> 00:45:11,960
your work more efficient, move 
faster. 

669
00:45:12,760 --> 00:45:20,040
Having a leader that creates 
this, this calmness in a world 

670
00:45:20,040 --> 00:45:24,960
that is chaotic and, and, and 
you know, fast-paced. 

671
00:45:25,360 --> 00:45:29,080
I think that is just such a 
skill that that if leaders have 

672
00:45:29,080 --> 00:45:32,920
it and can kind of harness that 
without slowing anything down, 

673
00:45:32,920 --> 00:45:36,800
but just this calm voice that 
says things are moving. 

674
00:45:36,800 --> 00:45:39,920
The way we approach it might 
look different next week, but we

675
00:45:39,920 --> 00:45:43,560
are focused, we are clear, we 
are confident and we are moving 

676
00:45:43,560 --> 00:45:47,040
forward in this direction. 
I I just think there's there's 

677
00:45:47,040 --> 00:45:50,960
such a skill and when you see it
done well, it just settles 

678
00:45:50,960 --> 00:45:53,360
everybody down and they can move
through change. 

679
00:45:53,600 --> 00:45:56,320
Knowing that like somebody's 
somebody's at the helm and 

680
00:45:56,320 --> 00:45:57,880
they're confident we're in the 
right direction. 

681
00:45:57,920 --> 00:46:00,160
It's really paradoxical. 
Yeah. 

682
00:46:00,160 --> 00:46:01,680
It is. 
It is. 

683
00:46:01,960 --> 00:46:03,440
Because on the one hand, I'm 
hearing like. 

684
00:46:03,880 --> 00:46:06,560
You know, it's, it's, it's 
really the leader's job to, to 

685
00:46:07,920 --> 00:46:10,400
not just navigate change. 
I mean navigate change. 

686
00:46:10,400 --> 00:46:18,160
That's so like, you know, 2020, 
you know, it's the leader's job 

687
00:46:18,160 --> 00:46:23,800
to keep the ball in motion 
during constant transformation. 

688
00:46:23,800 --> 00:46:28,280
So the leader is actively 
changing and moving the 

689
00:46:28,280 --> 00:46:33,200
organization towards something. 
And at the same time, what I'm 

690
00:46:33,200 --> 00:46:38,160
hearing is like the leader needs
to be a, a, a, a stabilizer to 

691
00:46:38,600 --> 00:46:40,800
the people in the organization, 
right? 

692
00:46:41,280 --> 00:46:45,880
So how does the leader move and 
propel the organization through 

693
00:46:45,880 --> 00:46:51,240
this context of constant change 
while also grounding people? 

694
00:46:52,000 --> 00:46:57,080
That's like a real Jedi skill. 
I want to add one other word 

695
00:46:57,080 --> 00:47:00,480
here. 
Cat use the word, but I, I, I 

696
00:47:00,480 --> 00:47:05,640
would almost juxtapose the, the 
calmness for the word I'm 

697
00:47:05,640 --> 00:47:10,800
thinking of, which is clarity. 
I think clarity makes everyone 

698
00:47:10,840 --> 00:47:13,680
more comfortable. 
I think we're we're 

699
00:47:13,680 --> 00:47:17,800
organizations struggle is when 
they're like, you know, 

700
00:47:17,800 --> 00:47:22,160
squirrels chasing, you know, a 
different nut every day that 

701
00:47:22,160 --> 00:47:27,320
feels super uncomfortable and 
and and not calming. 

702
00:47:27,640 --> 00:47:31,080
But I think clarity drives 
calmness. 

703
00:47:31,520 --> 00:47:38,200
And I think that those leaders 
that commit are also comfortable

704
00:47:38,200 --> 00:47:42,560
in recognizing if they commit 
and they need to pivot there, 

705
00:47:42,680 --> 00:47:45,040
there is less shame in that than
ever. 

706
00:47:45,400 --> 00:47:49,480
Like you should be rigorous at 
solving the problem, not about. 

707
00:47:49,480 --> 00:47:55,240
Rigorous on staying on the path,
Rigorous about solving the 

708
00:47:55,240 --> 00:47:57,800
problem, not just. 
Staying on the path, I love that

709
00:47:57,800 --> 00:48:01,800
because the path is like, you 
know, that's. 

710
00:48:02,360 --> 00:48:04,720
That's really that's. 
Really profound. 

711
00:48:06,120 --> 00:48:10,160
OK, this is this is fantastic. 
So I, I want us to just as we 

712
00:48:10,160 --> 00:48:17,160
get towards the end of the of, 
of the hour here to, to channel 

713
00:48:17,200 --> 00:48:24,920
your experiences working with a 
start up to scale up that is, 

714
00:48:25,360 --> 00:48:28,480
you know, about to go IPO or 
really just any kind of 

715
00:48:28,480 --> 00:48:30,440
inflection point. 
It could be a private equity 

716
00:48:30,440 --> 00:48:33,840
investment, it could be a 
fundraising event, but something

717
00:48:33,840 --> 00:48:38,440
that is going to create this 
discontinuous moment and propel 

718
00:48:38,440 --> 00:48:41,880
the organization into sort of a 
new level of growth. 

719
00:48:43,880 --> 00:48:46,960
What advice? 
So I'll start with you, Gary. 

720
00:48:47,200 --> 00:48:53,760
What advice would you give to a 
founder CEO who is about to 

721
00:48:53,760 --> 00:48:58,240
embark on that process and is 
saying, Gary, I got this, we're 

722
00:48:58,240 --> 00:49:02,080
good, we're solid. 
What advice would you give that 

723
00:49:02,080 --> 00:49:10,600
founder CEOII think the. 
Most dangerous thing for most CE

724
00:49:10,600 --> 00:49:13,880
OS is to stop questioning their 
assumptions. 

725
00:49:14,680 --> 00:49:18,320
And so they need to be 
constantly challenging their 

726
00:49:18,320 --> 00:49:21,560
assumptions. 
And again, this gets back to all

727
00:49:21,560 --> 00:49:24,000
the things we were talking 
about, the assumptions about 

728
00:49:24,000 --> 00:49:27,600
what got us here that may not 
get us there, the assumptions 

729
00:49:27,600 --> 00:49:32,120
about who on our team are the 
right people versus not. 

730
00:49:32,240 --> 00:49:37,080
It's also about our business 
model and our markets and our 

731
00:49:37,080 --> 00:49:40,040
solutions. 
Like you, you know, I always 

732
00:49:40,040 --> 00:49:44,920
tell this story about bias and 
how dangerous it is it is to 

733
00:49:44,920 --> 00:49:47,480
organizations. 
And let's say you had an 

734
00:49:47,480 --> 00:49:51,560
employee and they're always late
to every meeting and that really

735
00:49:51,560 --> 00:49:54,360
bothers you and you finally are 
fed up. 

736
00:49:54,840 --> 00:49:58,320
I'm firing that employee and now
you're going to hire a new 

737
00:49:58,320 --> 00:49:59,240
employee. 
And guess what? 

738
00:49:59,240 --> 00:50:03,200
That employee is, God damn it, 
going to be on time every time. 

739
00:50:03,480 --> 00:50:05,280
And you hire them and guess 
what? 

740
00:50:05,280 --> 00:50:09,560
They're on time every time and 
they can't spell. 

741
00:50:10,520 --> 00:50:15,160
And So what you've done is 
traded 1 issue for a different 

742
00:50:15,160 --> 00:50:19,560
issue and you haven't really, 
you know, thought about like 

743
00:50:19,760 --> 00:50:23,920
really without all the bias, 
without all the things that you 

744
00:50:23,920 --> 00:50:29,000
think made you successful, How 
do I now navigate this next 

745
00:50:29,000 --> 00:50:34,120
journey if I don't feel 
comfortable, empowered and part 

746
00:50:34,120 --> 00:50:37,320
of my daily existence to 
challenge what I believe are my 

747
00:50:37,320 --> 00:50:42,280
truths so constantly? 
Scrutinizing and challenging 

748
00:50:42,280 --> 00:50:46,200
one's assumptions. 
I I think that's incredible. 

749
00:50:47,720 --> 00:50:51,080
Sage advice, Gary, thank you. 
Thank you. 

750
00:50:51,080 --> 00:50:59,800
OK, Cat, you could go with the 
founder, CEO or or CHRO or chief

751
00:50:59,800 --> 00:51:03,680
talent officer of an 
organization about the IPO. 

752
00:51:03,680 --> 00:51:06,920
They say like we got this, we're
fine, it's all good. 

753
00:51:07,240 --> 00:51:09,040
We're we're ordering the 
confetti now. 

754
00:51:09,040 --> 00:51:12,680
It's going to be amazing. 
You know, all I need advice on 

755
00:51:12,680 --> 00:51:16,000
is like, you know, what are we 
going to have for our appetizers

756
00:51:16,000 --> 00:51:18,120
at the, at the the post IPO 
party? 

757
00:51:18,520 --> 00:51:22,000
What advice would you give to 
that person? 

758
00:51:24,760 --> 00:51:26,360
First, I'd say you need to 
delegate, maybe a. 

759
00:51:26,360 --> 00:51:28,560
Little bit more effectively. 
That doesn't seem like the 

760
00:51:28,560 --> 00:51:30,800
decision making. 
You should be focused one of 

761
00:51:30,800 --> 00:51:34,720
that moment. 
That might be a separation 

762
00:51:34,760 --> 00:51:38,960
conversation. 
I, you know, I think if, if 

763
00:51:38,960 --> 00:51:42,160
you're leading a people team 
that's, you know, scaling 

764
00:51:42,160 --> 00:51:46,440
rapidly, it, it might be a 
little bit boring, but I think 

765
00:51:46,440 --> 00:51:48,800
it's like, go and check out your
foundations. 

766
00:51:50,000 --> 00:51:53,000
Do you know what great looks 
like in leadership? 

767
00:51:53,400 --> 00:51:59,720
Do you have a clear, solid, you 
know, very wide, very deep bench

768
00:51:59,720 --> 00:52:03,360
of leaders who are either 
building to be ready for that 

769
00:52:03,360 --> 00:52:07,400
sort of executive level job or 
are ready now when you're sort 

770
00:52:07,400 --> 00:52:11,480
of like keeping them warm? 
I think we talked about it a 

771
00:52:11,480 --> 00:52:15,120
little bit, but attrition is a 
really big, you know, really big

772
00:52:15,120 --> 00:52:18,360
risk when you go through all 
these changes and all the 

773
00:52:18,360 --> 00:52:22,680
changes we sort of talked about.
And so managing your risk around

774
00:52:22,680 --> 00:52:25,560
attrition, particularly at that 
executive level. 

775
00:52:25,920 --> 00:52:30,680
I that would be my like #1 to 
get after and just really being 

776
00:52:30,680 --> 00:52:33,480
clear on sort of who, who is 
your succession slate? 

777
00:52:34,200 --> 00:52:37,840
Don't do 1 to 1 replacements, 
but really think about that next

778
00:52:37,840 --> 00:52:40,760
leadership bench. 
I think sort of there's twofold.

779
00:52:40,760 --> 00:52:45,160
1 is you may lose an executive. 
You don't really know how any 

780
00:52:45,160 --> 00:52:47,520
one person is feeling and things
are changing. 

781
00:52:47,520 --> 00:52:51,680
And so I'm being prepared to 
have somebody to step into that 

782
00:52:51,680 --> 00:52:53,440
role. 
So that business continuity is 

783
00:52:53,440 --> 00:52:55,920
there as much as possible, I 
think is important. 

784
00:52:56,480 --> 00:52:59,840
And then I also think these 
executives are about to move 

785
00:52:59,840 --> 00:53:05,400
into maybe the biggest role of 
their lives, maybe adding much 

786
00:53:05,400 --> 00:53:07,760
more complexity to their role in
the day-to-day. 

787
00:53:08,240 --> 00:53:10,880
The CEO, you know, we talked 
about is sort of going to go 

788
00:53:11,000 --> 00:53:13,320
have this different, different 
job, if you will. 

789
00:53:14,000 --> 00:53:17,160
And so if you've got a super 
strong set of leaders that are 

790
00:53:17,160 --> 00:53:20,920
there supporting and lifting up 
that executive group as they 

791
00:53:20,920 --> 00:53:25,000
step into this new moment, I 
think, you know, that's that's 

792
00:53:25,000 --> 00:53:28,520
huge as well. 
So yeah, focus on your bench, 

793
00:53:28,920 --> 00:53:32,000
get you ready now leaders set up
and, and, and good to go. 

794
00:53:32,000 --> 00:53:34,440
And then sort of following from 
there. 

795
00:53:35,520 --> 00:53:39,400
Excellent advice SO. 
Have a like sort of a deep 

796
00:53:40,360 --> 00:53:43,640
talent pipeline. 
Like don't just assume that like

797
00:53:43,640 --> 00:53:47,880
this All Star team that that 
sits at the C-Suite that they're

798
00:53:47,880 --> 00:53:53,120
going to be there forever. 
Like we need to have good talent

799
00:53:53,160 --> 00:53:57,320
at multiple levels and to be 
thoughtful about, you know, 

800
00:53:57,320 --> 00:54:01,440
readiness and and succession is 
what I'm hearing like that, that

801
00:54:01,440 --> 00:54:03,520
that, you know, like who wants 
to think about that when we're 

802
00:54:03,520 --> 00:54:06,400
about to like all become, you 
know, gazillionaires? 

803
00:54:06,400 --> 00:54:08,840
But like, that's actually what 
we need to be thinking about 

804
00:54:09,040 --> 00:54:11,680
creating a really healthy, 
robust talent pipeline. 

805
00:54:13,120 --> 00:54:15,120
Exactly. 
And I feel like in these. 

806
00:54:15,120 --> 00:54:17,760
Moments because they are so 
exciting and everybody's like 

807
00:54:17,760 --> 00:54:21,080
ready for the next thing that 
sometimes that can slip away 

808
00:54:21,080 --> 00:54:24,200
like, Oh no, our executives are 
super excited to be here. 

809
00:54:24,200 --> 00:54:26,360
They've worked so hard to get to
this moment. 

810
00:54:26,640 --> 00:54:30,280
They're going to carry on doing 
this, you know, be here forever.

811
00:54:30,280 --> 00:54:33,040
And, and actually, what we see 
in the data is sort of the 

812
00:54:33,040 --> 00:54:36,800
opposite of that. 
And so that can be yeah, that's,

813
00:54:36,800 --> 00:54:38,080
that's sort of the 
recommendation. 

814
00:54:38,800 --> 00:54:43,720
Really, really good advice. 
Any parting thoughts? 

815
00:54:44,720 --> 00:54:47,600
Any, you know, we, we covered a 
lot of ground here. 

816
00:54:47,680 --> 00:54:52,880
Gary and Kat, any, any parting 
thoughts or, or other advice 

817
00:54:53,160 --> 00:54:56,000
that you would give to our 
listeners who are keen to 

818
00:54:56,000 --> 00:54:58,840
understand leadership in 
general, 'cause this is a 

819
00:54:58,840 --> 00:55:03,640
podcast about leadership, but 
also specifically in this 

820
00:55:03,640 --> 00:55:10,440
context of, of start up the 
scale up and how do we mature 

821
00:55:10,720 --> 00:55:14,720
effectively, right? 
How do we mature effectively and

822
00:55:14,720 --> 00:55:20,880
intentionally? 
Cat Sart. 

823
00:55:24,240 --> 00:55:26,280
Oh God. 
Well. 

824
00:55:26,280 --> 00:55:29,080
You know, one thing that we 
haven't really, I don't think 

825
00:55:29,080 --> 00:55:31,600
we've touched on necessarily. 
So I'll throw it out there as, 

826
00:55:31,600 --> 00:55:35,120
as something to think about and,
and not necessarily, you know, 

827
00:55:35,120 --> 00:55:37,120
final words of wisdom or 
anything like that. 

828
00:55:37,120 --> 00:55:41,960
But I I've been thinking a lot 
about lately how we help 

829
00:55:43,280 --> 00:55:46,400
founders and executive teams 
that have been going through a 

830
00:55:46,400 --> 00:55:50,400
shift from the start up to more 
scale is how do we help them 

831
00:55:50,400 --> 00:55:55,040
really trust the experts that 
they have brought in and put in 

832
00:55:55,040 --> 00:55:59,760
place around them with the 
intention that these are experts

833
00:55:59,760 --> 00:56:03,760
in this particular thing. 
And you know, maybe it's what, 

834
00:56:03,760 --> 00:56:06,320
yeah, it could be anything 
marketing, you know, accounting,

835
00:56:06,320 --> 00:56:12,320
treasury, whatever, legal, but 
like hiring an expert at senior 

836
00:56:12,320 --> 00:56:18,600
levels and then how do you trust
them and take their advice and 

837
00:56:18,600 --> 00:56:22,400
stay curious and know your own 
limitation in that space? 

838
00:56:23,920 --> 00:56:27,080
I think it's something that that
at least instead of in my 

839
00:56:27,080 --> 00:56:31,280
experience is sometimes it's so 
hard for the CEO to say 

840
00:56:31,520 --> 00:56:34,920
actually, I don't have an 
expertise in this area. 

841
00:56:34,920 --> 00:56:38,480
Maybe I don't know the rights of
decision here. 

842
00:56:38,840 --> 00:56:41,280
I've hired all these really 
expensive talent. 

843
00:56:41,480 --> 00:56:44,440
Let me get them in a room and 
they can tell us how we move 

844
00:56:44,440 --> 00:56:47,440
forward. 
And so I, you know, there's 

845
00:56:47,440 --> 00:56:50,880
something here around. 
Stay curious, stay humble and 

846
00:56:50,880 --> 00:56:53,160
trust your experts. 
You've paid a lot of money for 

847
00:56:53,160 --> 00:56:54,560
them. 
You should be listening to them.

848
00:56:57,000 --> 00:57:02,200
Yeah, I, I, I have a a similar 
idea, but a bit of A twist, 

849
00:57:02,200 --> 00:57:08,360
which is to say you should 
really try to match your exit to

850
00:57:08,360 --> 00:57:13,600
your leadership capability. 
And the, the, the fact that an 

851
00:57:13,600 --> 00:57:18,440
IPO seems bright and shiny and 
amazing and you have this image 

852
00:57:18,440 --> 00:57:21,880
of yourself ringing the damn 
bell like that's amazing. 

853
00:57:22,320 --> 00:57:24,800
But you may not be that kind of 
leader. 

854
00:57:25,160 --> 00:57:27,840
And there is no shame in you 
saying that. 

855
00:57:27,960 --> 00:57:32,960
My monetization of my business 
may come through other means 

856
00:57:32,960 --> 00:57:37,880
which are just as fulfilling, 
but not maybe the IPO. 

857
00:57:37,880 --> 00:57:41,440
It's not like the IPO is the 
only exit. 

858
00:57:41,760 --> 00:57:44,840
It's not like the IPO is the 
best exit. 

859
00:57:44,840 --> 00:57:49,360
Like you need to really match a 
little bit and and to using 

860
00:57:49,360 --> 00:57:53,560
Cat's word, being humble enough 
to recognize where your skill 

861
00:57:53,560 --> 00:57:57,080
set is and what is the exit 
that's going to match on what 

862
00:57:57,080 --> 00:58:01,880
you can actually deliver you. 
You need to really be honest in 

863
00:58:01,880 --> 00:58:04,600
the end about that. 
Wow, the great. 

864
00:58:05,640 --> 00:58:09,320
The great irony, you know, we're
talking about IPO, which is this

865
00:58:09,320 --> 00:58:13,320
like ecstatic moment. 
You know, you see, you know, 

866
00:58:13,320 --> 00:58:16,000
usually, I mean, not always, 
usually you need to see this 

867
00:58:16,000 --> 00:58:20,640
like big pop in the stock price 
and overnight, you know, people 

868
00:58:20,640 --> 00:58:24,440
become, you know, millionaires 
or, or, you know, that that 

869
00:58:24,440 --> 00:58:26,800
there's, there's this 
opportunity to get liquidity and

870
00:58:26,800 --> 00:58:28,280
something they worked so hard 
for. 

871
00:58:28,800 --> 00:58:32,960
And wow, I imagine that could be
something that could, could go 

872
00:58:32,960 --> 00:58:35,160
to, you know, one's head 
quickly. 

873
00:58:35,160 --> 00:58:38,200
But yet we're talking about, 
we're ending this podcast about 

874
00:58:38,200 --> 00:58:42,920
leadership on the topic of 
humility being, you know, 

875
00:58:43,760 --> 00:58:49,320
really, really significant, 
really important self-awareness,

876
00:58:50,040 --> 00:58:56,760
humility, trust. 
And so I, I this is, this is 

877
00:58:56,760 --> 00:58:58,760
fantastic. 
I think it's the perfect place 

878
00:58:59,280 --> 00:59:03,080
to, to stop. 
And I just want to thank you, 

879
00:59:03,080 --> 00:59:09,120
Gary and Kat, for taking the 
time to share your experiential 

880
00:59:09,280 --> 00:59:12,040
wisdom. 
So everybody knows you guys are 

881
00:59:12,360 --> 00:59:16,720
wicked smart and wise, but 
there's experience in the 

882
00:59:16,720 --> 00:59:19,480
trenches with these 
organizations, with these 

883
00:59:19,480 --> 00:59:23,080
founders and CE OS that you 
bring to bear. 

884
00:59:23,080 --> 00:59:24,880
And it's just so valuable for 
us. 

885
00:59:25,840 --> 00:59:29,200
So, so thank you so much and 
thank you to all of our 

886
00:59:29,200 --> 00:59:31,480
listeners. 
This is a podcast about 

887
00:59:31,480 --> 00:59:35,240
leadership and looking forward 
to our next episode. 

888
00:59:35,720 --> 00:59:37,120
Bye for now. 
Thank you.

