For leaders the temptation to tell, fix, and even do is so strong. “I know the way,” or “I have the answers,” or “the buck stops with me.” Sometimes it’s impossible to resist the ego boost of providing the answer, giving the fix, telling the way. But what impact does this have on the team, and ourselves? And is it even true? Jerry Colonna is joined today by Patrick Campbell, co-founder and CEO of Price Intelligently – a bootstrapped company in Boston. Patrick and Jerry explore different leadership styles, the power of “if I die docs,” and how the secret to leadership, and servant leadership, may not lie in having the right answers, but instead asking the right questions.

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“The only way to create a humane, scalable organization that allows every individual to realize
their fullest potential is that 'Servant Leadership' model, whereby there is no 'us' and 'them.'
There's no 'them,' there's only 'us.' There's no 'you' and 'me,' there's only 'us' and that not only
creates a more efficient and effective organization and one in which people can grow, but from
the CEO's perspective it's a hell of a lot more fun.”
Welcome to the Reboot podcast.
Hi, this is Dan Putt, one of the partners here at Reboot. Do you remember when you learnt how
to ride a bike? Did you ever feel frustrated and perhaps direct that frustration outwardly? I
remember my learning experience very, very clearly; I can still see the way the reds and the
yellows of the evening reflected off the windows in the front of my house, and how cool the
bright-green grass was beneath me and how pissed I was at my mother. "Why?" I wondered.
"Why was she wasting my time? Why bother with holding the secret of balance? Just tell me.
Why let me fall and fall off my bike into the dewy grass?"
As badly she wanted to tell me and I'm sure it was hard for her to see me fall, the only way for
me to learn was to feel my way through it, to do it on my own. She could support, but not fix.
She could support, but not do. She could support, but not tell. My mom understood, in order for
me to grow, she needed to let go.
For leaders, the temptation to tell and fix and even do is so strong, "I know the way," "I have the
answers," "The buck stops with me." Sometimes, it's impossible to resist the ego boost of giving
the answer, giving the fix, telling the way, but what impact does that have on the team? What
impact does that have on the leader? Is it even true? Jerry is joined today by Patrick Campbell,
co-founder and CEO of Price Intelligently, a bootstrapped company in Boston. Patrick and Jerry
explore different leadership styles, the power of Patrick's "If-I-die" docs and how the secret to
leadership may not lie in having the right answers, but in asking the right questions.
"A leader is best when people barely know he exists. When his work is done, his aim fulfilled,
they will say: we did it ourselves." – Lao Tzu.
**
Jerry Colonna: Hey Patrick, it's really great to have you on the show, thanks for coming
on.
Patrick Campbell: Absolutely, great to be here.
Jerry: Patrick, why don’t you take a minute and just introduce yourself, and then we'll
sort of dive in and we'll talk about what we are hoping to talk about today?
Patrick: Yeah, absolutely; so I'm the CEO, co-founder of Price Intelligently. We're a
pricing software company here in Boston, Mass, and we also make something
called Profit Well, which is financial metrics for subscription companies. Going
deeper than just the LinkedIn resume, I am a Midwesterner, I'm from Wisconsin,
born and raised out there, went to school in Illinois and prior to founding Price

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Intelligently with my co-founders, worked at Google and kind of a big corporate
tech, and then I also worked for the US Government in Intel. So, lots of fun
stories there that we might have to take away from the final cut of this.
Jerry: Oh no, we're gonna keep it all in; everything stays in here. All right, so the first
thing that I have to ask about is Wisconsin; what city 'cause many people may
know that my co-founder and our partner, Ali Shultz was born in Eau Claire, so –
Patrick: Oh, awesome, so I'm from a small town called Jackson, Wisconsin, so I always
used to say, there's a town of more cows than people, which was the truth I think,
up until a few years ago, but I'm on the other part of the state North of
Milwaukee, so, basically like an hour outside of Milwaukee. Parents both
working, either downtown or in the suburbs, but it was a fascinating upbringing,
growing up in kind of the country and had a little bit of that country lifestyle
especially in the context of good, old Wisconsin.
Jerry: All right, so you know, I have come to own up to the fact that I am fascinated
with Midwest, you know, Dan Putt, who does the intros on these shows is from
Ohio, and Ali is from Wisconsin, as I said, I'm gonna do something – even though
we are only recording the audio, I'm gonna do something that I see my Wisconsin
friends do all time, which is, I'm holding up my hand and I'm pointing to the part
where – you're smiling 'cause you know what I'm talking about?
Patrick: Yeah.
Jerry: You point to the part of the state.
Patrick: Exactly; Michigan, Wisconsin, yeah, it's a good time. I don’t know, it's kind of
fascinating 'cause I met a lot of like Wisconsin and Midwesterners, even in
Boston. We are based in Boston – in the tech scene, I think it attracts a certain
type of person and the Midwesterners are typically built properly for that, which
is great.
Jerry: Yeah, and I just realized, one of my other partners, Jim Morrison is from
Michigan, so again, you hold up the hand –
Patrick: Yeah, except for those Eupers [Phonetic] right?
Jerry: Yeah, he's not a Euper, that's for sure. So, that's good, we got that out of the way
and I think that part of the reason the whole connection with Midwest I find so
powerful is that in my experience, there is a kind of a work ethic that I can often
attribute to people from the Midwest that, in a funny way, reminds me of my
grandfather, who emigrated from Italy at the turn of the 20th century. It was a
kind of like, we just get up in the morning and we do our shit.
Patrick: Yeah, you just described my father basically.

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Jerry: Tell me about that; and as people who have listened to the podcast, now I often
end up with "Tell me about your father," so tell me about your father.
Patrick: I don’t know if there is – I mean, there's obviously not a closed market for a work
ethic, but I would say that I have found, historically, that that is to be the case,
there is this classic, whether it's a stereotype or the truth, I think I find it more
truth than not, but like my dad – I come from a very blue-collar family so you
know, I was the first person to go to college, like that kind of a classic upbringing.
I was a little bit of the black sheep as like the nerdy, smart kid, that kind of thing,
but you know, my dad is extremely intelligent. He is one of those guys who – he's
a tinner, he was a sheet-metal worker for 30 years working outside on skyscrapers
and now he is an HVAC guy, but I think the classic thing about my dad which has
taught me a phenomenal amount is, he's a kind of guy where it's no-nonsense in
the sense of like there's not a lot of BS, he goes to work, and he expects that, for
his labor, he's gonna get a fair wage, benefits, he's going to get a week off a year
or two weeks off a year whatever it is, and he is going to kind of, live his life that
way. And you know, that's not an uncommon story what I just said, but kind of a
guy he is and I think a lot of Midwesterners are like this, they get actually
obsessed with learning, which is really fascinating. My dad comes home and he's
not a guy who is like watching TV every night; he actually has this huge library of
old text books and old training manuals that you know, we make fun of him for
going to second-hand bookstores, and that's where he gets most excited where he
finds like this old manual about sheet metal or steam or something, and then he
spends all his time doing that. Prior to that – he is just retired from the Navy, he
was a Navy Reservist for 28 years. It's one of those things where people don’t
stop. They just don’t stop; like they spend a lot of time at the bar, they spend a lot
of time watching Packard games, but they got some sort of hobby. My mom is a
hardcore quilter, you know, that's all she does besides working and spending time
with her grandkids and I think it really speaks to that work ethic where they just
kind of don’t stop and they obsess about some different things even if they are not
necessarily, you know, cool to us, you know, other folks out there.
Jerry: You know, it's like, often times when I do these podcast conversations, I wish that
the audience could actually see somebody's face, 'cause I wish they could see your
face as you are talking about both your mom and your dad.
Patrick: Yeah.
Jerry: And I don’t mean to presume that you know, every day was a great relationship,
'cause you know, we are human –
Patrick: Yeah, absolutely.
Jerry: – but, I can feel the pride that you feel –

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Patrick: Yeah.
Jerry: – and that image of your dad and I think it's really powerful. I think being able to
connect back into that role model is really powerful. Does that resonate with you?
Patrick: Yeah, I think it does; I think – like all parents, there's no perfect parent, and –
Jerry: I sort of remind myself as I think about being a parent myself, I've got three kids,
so – go ahead, I'm sorry.
Patrick: But, yeah, so I'll leave that one there for a second, but I think you know, with my
– I think my parents, they did – you know, I wasn’t an easy child either and so
let's hedge that and so I think I learnt a lot about, you know, what to do and a lot
of like maybe I wanted to do it a little differently, you know in my life, which I
think is a part of being someone who grows up, but yeah, I absolutely like, you
know, it's that classic cliché of like, "Oh, damn it, that's from –" you know, that's
my mom right there, that's my dad right there and I think overall, like I'm
extremely gracious for the upbringing that I had because we didn’t always have a
lot of cash. You know, we were lower middle class because we had a job, my
dad's a union guy, which we argue about all the time and he had some hard times
because of the strikes and stuff like that, but it's one of those things they just kept
going and I think that's something that's pretty admirable and you could cross-
reference that with the whole millennial debate that's happening right now in the
wake of some of the blog posts that are written about "Oh, I deserve this," "I don’t
deserve that," that kind of thing. It's one of those things where a lot of that
generation, they might piss and moan about a lot of stuff, but they are also like,
"We just have to keep going" and I think that's something that's really admirable
about them.
Jerry: Yeah, I think that there is – and again, I'm not gonna suggest that there is sort of a
perfectly correct way to be existentially to be with work but, you know, as you
were describing that, I was thinking of my own father and the role that the union
that he was in played in. My father passed about 23 years ago, and when we were
kids – I'm one of seven siblings, and I'm number six, so I was at the back end, or
the hand-me-down end, 'cause I didn’t get –
Patrick: Sometimes that came around, right, 'cause it was so worn out, you had to get the
new stuff sometimes.
Jerry: Yeah, sometimes, rarely; but you know, my most favorite thing was getting the
hand-me-down catholic school uniforms. And we struggled, a lot of times, to
actually have enough money to pay bills and even sometimes food, although I
think my parents tried to do a good job of hiding that fact from us, and there were
many times where the union stepped in. And it wasn’t the union per-se, but it was
the other folks in the union.

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Patrick: Yeah, that brotherhood or that camaraderie, and I think what's fascinating is you –
so I'm an economist, you know, my background is econometrics and math and
that's mainly the argument that I have with my parents a lot of times because you
know, for a tech company, like, I worked at Google for a while and like a union at
Google would be crazy. You know, they take so much good care of you, but I
think that one thing that a lot of entrepreneurs, particularly founders don’t have
around them is that I don’t really know what the gender-neutral term is, but the
brotherhood or that camaraderie around them to, you know, lean on folks or in
those hard times, you know, not necessarily lean on them for, you know, food and
clothing, but something along the lines of like mentally lean on them or "Hey, I'm
out of work, the company went bust, can I get some contract work?" like that kind
of thing and I think that as you were alluding to that, that's one huge, positive
aspect. I got an older brother who is also a blue-collar guy, he's an electrician, and
you know starting out, he's travelling around, but he's always guaranteed a job.
You know, once he was an apprentice and a journeyman, so yeah, it's fascinating
how helpful that can be.
Jerry: Yeah, I mean, what it brings to mind is this notion that we often work with, which
is the – you know, the benefit of knowing that you are not alone.
Patrick: Yeah.
Jerry: And a few months back, we broadcast a conversation between Ian Hogarth from
Songkick and Yancey Strickler from Kickstarter and they talked really beautifully
about the relationship between the two of them and the way in which they just
kind of reach out across the Atlantic and support each other, CEO to CEO.
Patrick: That's awesome.
Jerry: And it's not quite that sort of union brotherhood that you were talking about, the
union, sort of camaraderie of you know, the kind of guild, we are in this together
in that way –
Patrick: Sure.
Jerry: – but this notion of is there a way in a gender-neutral way, 'cause I think you are
pointing that out as in really important, to really foster a sense of connectedness
among entrepreneurs, and you know, so much of what we are about at Reboot is
really about people talking without bullshit, without filters, without spinning each
other, about the ups and downs, of what it's like to really try to build something. I
mean, that's one of the reasons we actually invited you on to the show 'cause you
know, we know a little bit about your story and I'm gonna ask you to go into it a
little bit more, but you know, one of the things, and I wonder if it has to do with
your Wisconsin blue-collar roots, but one of the things that comes so clearly
across is, how do I put this, there's a kind of authenticity about you that's
unassuming, but also unafraid.

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Patrick: That's very nice of you; I think that's probably the best way someone's described
me. I have to share that with my team here and see whether they agree with you or
not.
Jerry: We'll explain that to people.
Patrick: Yeah.
Jerry: And I think that, you know, I was looking forward to just hearing a little bit more
about your story; you know from what I know, Price Intelligently, you all sort of
founded it by – if I remember correctly, you left Google, and sort of dove into
bootstrapping your own business.
Patrick: Yeah, so I worked for the US Government, I kind of mentioned that, I worked in
US intel, doing value modeling, and it's a big fancy way of saying building
different formulas with data to try and find you know, targets and things like that
and what was fascinating about it is you know, I was there and I ran into the
public bureaucracy, right, you know, which is like, you know this person is being
here for 30 years and people joke that he or she hasn’t worked in the past ten, you
know, 'cause of the government thing and things move slow. So I got a little
[Inaudible 0:17:52] with that and went worked at Google and ran into another
bureaucracy. I was working on some products for them that – well, I was in sales
but I you know I noticed I wasn’t really a differential person relative to my peers
because I got hired in with a lot of Ivy League kids and you know, just brilliant
but they also had the degree and so I was – I got to go learn to code, to kind of
separate myself and started building some tools that I scaled and made Google
more money and couldn’t get resources because the bureaucracy. But one of the –
the biggest things I think really shaped me now and I'm kind of laying the
groundwork for is, when I was at Google, I actually got cancer. So, it wasn’t, you
know, hugely dramatic, you know, I had prefaced that because it wasn’t stage IV
stage V, like you know, I'm not a medical miracle or anything like that, but it was
you know, serious enough that you know, I went to treatment, surgery, some more
treatment, you know, but what was fascinating at Google was my boss, after I told
him, was just like "Hey, if you just want to leave for a quarter and just not be here
and get paid and everything, that's cool." It was just one of those fascinating
things where you are like, oh my god, this culture is amazing. This is an amazing
place, but the unfortunate flip side of that at least for me being a fulltime
employee at Google was that I, you know, had the realization that I think a lot of
you know, millennials would say to kind of talk about that category or having
which is, "Oh my god, do I want to work here and like sit on this golden treadmill
which is amazing, and I don’t want to complain because like, you know I'm
getting paid way too much for my actual skills. It's like Disneyland for adults, like
it's amazing, but like I'm selling ad words." You know, it's not fulfilling, it's
amazing and you feel bad because the people you work with are awesome. You
can't get better, but you are not really fulfilled from an occupation standpoint and

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so, long story short, you know, I jumped out from there. I did work at another
startup for about a year in Boston because I kind of admitted to myself I was very
naive at Google, I was like, oh, I've done this stuff and you know, I can go start a
company, I'm smart, blah-blah-blah and then I don’t know what actually I don’t
know what it was, I think it was actually Jay who – I don’t know if we talked
about when the tape was rolling, but I worked with him at Google actually and he
had left, he was a bit older –
Jerry: And Jay's first name is Acunzo?
Patrick: Acunzo, yeah, one of those Italian –
Jerry: Forget those guys, [Crosstalk]
Patrick: Those 'pizons,' I'm told.
Jerry: That's right.
Patrick: I'm always scared 'pizon' is a naughty word.
Jerry: No, 'pizon' is a good thing, trust me.
Patrick: We have a Zado here and Epelina, I think that's how you – or Antonina is her real
name, she goes by 'Nina' but I'm always like "Oh, pizon," and I'm always scared
I'm saying the wrong word, but yeah, so I think I was talking to Jay or I think I
went to a meet-up and I was like, "Oh holy shit, I have no idea what I'm doing."
So, I went and worked for another company in Boston called Jim Vara, and that's
where I first – you know I was kind of like a strategic initiatives guy, so I was
working on like, everything from project management and product management,
all the way like building spreadsheets to give sales reps or customer service reps
different documents that they needed to streamline stuff, and I was working on
pricing for one of my projects and that's kind of when I realized, holy cow, this is
a huge issue because we would make changes and we would see enormous like
lift, or enormous like cratering of different directions, and then you know, I was
like, oh no one knows anything about this, no one does anything about it, like they
just kind of throw stuff against the wall and kind of go from there. So, that's kind
of the back story, up at least until like starting the company and I was getting a
little ancy at that company, it was about 60-70 people and I had met a couple of
my co-founders who were some good product folks in Boston and just kind of
jumped out from there. I'll pause there in case like, I could provide any more
details 'cause I know I just kind of gave you the tome of my life history for the
past couple of years –
Jerry: No, it was great I mean, it really gave the context and you know, it's sparking a
whole bunch of thoughts for me, one of which is, so as I understand it correctly,
you then bootstrapped to start price intelligently?

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Patrick: Yeah, so we started off; so one of the guys in the three of us, we sold a small,
little product, to a company called Crashlytics, so they got bought by Twitter
eventually, and they – I don’t even know if they remember that they bought it, it
was not for a large sum of money, it was like, you know, like I don’t even know if
it was like five digits, very low amount of money, and so we used that as like the
start. Cashed in my 401k from Google and these two guys were part time initially
which is like a whole another thing that we could talk about and the struggles with
that kind of arrangement and we started self-funded and the main reason was we
probably could have raised money initially, just on idea, name all that stuff, and
keep in mind, this is 2012 at this point and like middle of 2012 and cash was
starting to become fairly plentiful and cheap. But we didn’t know like there's a
[Inaudible 0:24:02] problem of pricing, we didn’t know like, "This is the thing
we are going to build" or "This is what we are going to focus on" and so we
started and the first six months, we didn’t make any money and then like from
there, we finally make like enough to – I made a decision and it was just me
fulltime at this point, those guys were helping out in the nights and weekends, a
little bit here and there, and then it was like all right, do I hire first employed like
take this part off of my plate or do I pay myself? And I hopefully in hindsight, a
good decision, hired Peter Zotto is basically GM of Price Intelligently at this point
and he was our first on-board and yeah, we kind of went from there. So yeah, self-
funded, we haven’t raised a dime of funding, all customer-focused, and have
grown, I mean, we are about 20 people now, which is great.
Jerry: So, one of the things I've been sitting here thinking about is, how do you think
your experience of growing up watching your parents, growing up in Wisconsin,
growing up being sort of odd, nerdy guy, if you will –
Patrick: Yeah, I like that.
Jerry: – how do you think, if anything, it influenced your decision to sort of do it as a
bootstrap?
Patrick: I don’t know actually; that's a really good question. I think, like if I take a step
back, I would actually argue that my upbringing made me more risk-averse at
least from things that I learnt from my family because like it's kind of like a risk-
averse lifestyle; you are a laborer so you are getting paid for your time essentially
and it's one of those like labor skill trades, my dad is into that and let me – so it's
one of those things where you know, you could always probably find a job, but
it's not necessarily something that you like try to test. You know, you are not like,
"Oh, I'm gonna take this risk." But I would say that it probably actually influenced
me more in a positive direction just because I had this foundation behind me, so
you know I was able to go to college, was intuitive enough that if everything like
hit the fan, what I always said during that point when my parents were like, "I
can't believe you left Google, now you are leaving this other company that has 15
million in funding, like what are you doing?" It was more like I could always find

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a job, I can always find a job, I can always find enough to live essentially. But I
do think that kind of – I'm reflecting out loud here a little bit, I would say that the
work ethic aspect, I think probably influenced a lot because I just think that
maybe naively it was one of those things where it was like "Well, do we go raise a
million on some decent valuation?" It's like well, yeah, or we could just work hard
the next three months and like get to that point, but our goal is – once we get on
the investor treadmill, you have to like stay on it because there's higher
expectations and you kind of keep going, and yeah, I think if I didn’t work – and I
know everyone does this but like for us, at least for the record, if I work 18-hour
days, six days a week, seven days a week, sometimes, for those first six to nine
months, we'd probably would have needed to raise money and just because – and
I'm not having a hero complex there, from just the time and deliverable
standpoint, it's one of those things where you know, time and cash were fungible
and so we were able to basically take some cash off the clock just because we
were putting a lot of time in.
Jerry: I had a sense that there was a connection here and hence my question, but I think
that I made a positive theory which is that it is a little bit different than what you
just described. I think that even if you had raised a million dollars, you still would
have worked 18-hour days.
Patrick: Yeah, that's true.
Jerry: Because –
Patrick: I don’t really have a lot of friends Jerry, so –
Jerry: – well, the math nerd, but here's my theory, I grew up in very similar
circumstances, albeit in Brooklyn, not in Wisconsin, and –
Patrick: So, you are saying you can beat me up, that's what you are saying?
Jerry: I can totally kick your ass. But, I think that growing up in the circumstances that I
grew up in, I used to always say this, "Come hell or high water, I know that I can
make money." I don’t always know that I can raise money, I don’t always know
that I can succeed in the game, you know, the game playing –
Patrick: Absolutely.
Jerry: – but I can always count on making –
Patrick: No, that's –
Jerry: Does that resonate with you?

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Patrick: That opens up a lot of lines of fire, I think there's a negative aspect to that too
right?
Jerry: Tell me.
Patrick: You're not a coach, you're a player right? You're not coaching enough 'cause
you're like, I'll just do it, you know that kind of thing. I think that's true, I think –
my confidence in raising money now is a hell of a lot more – if we needed to raise
around tomorrow, like, I know who to go to, I know what the pitch would look
like, you know, but back then, I had like very little confidence in it. I'm not saying
that's a bad thing necessarily, but yeah, I think that 100% resonates, yeah,
absolutely.
Jerry: And I think – you know, I often said to my grandfather, whose work ethic taught
me this which is, "A good entrepreneur always makes sure that there's more
money at the end of the day than there was at the beginning of the day."
Patrick: Yeah, absolutely.
Jerry: And that means like, you know, the point of actually building a business is
actually to make profit.
Patrick: Yeah, I think it is –
Jerry: It's not – go ahead.
Patrick: I think I look at it a little bit differently; at the end of the day, absolutely. If you
have the – is it that or not, I would say, yeah. I think for me, and this is kind of
been like combining the work ethic but also like the "Oh shit" moment at Google,
I think for me it's not just like, it's the efficiency of time, right? Like, money at the
end of the day might actually equate to – you know, we have these things that we
kind of implement, so we call them – it's very morbid, but we say, 'If-I-die' docks,
like everyone has like an 'If-I-die' doc, which is like, this is what I do, here's all
my Google docs, connected all those types of things, and that was a big part of
early on, which was like you know, okay, how do we make an hour create five
hours, if that makes sense. Like how can we structure the business in a way
where, you know, profit might not come for a while, cash might not come for a
while or it might not be enough, but like how can we boost the efficiency so a
little bit of a tangent there, but I think that's kind of how it would shape at the end
of the day. It's all about profit, I think it is, but it's to when that profits realized,
which is you know, some variation, which I would agree or disagree with.
Jerry: Yeah, you know, the image I just got was like the 'If-I-die' doc, is both – it's a bit
of an insurance policy, so you are all connected to each other to know what's
going on, but it's also a means by which you seem to be really focusing on

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efficacy, efficiency and effectiveness and I'm wondering if your background as an
economist – it was economics that you majored –
Patrick: Yeah.
Jerry: – really sort of lead to some of that.
Patrick: Yeah, I think it's – I don’t know if it was – like the old classic like how many
_____ does this create of happiness or of value or something like that. I think to
me, it's actually more about – there is a chance that I could die and I don’t fear
death in the sense of like, you know, I'm scared of it, I don’t feel like I've done
enough, it's more like, I've come to the terms to produce a truly valuable business.
So we are talking about something that compounds and grows and things like that,
it can – and this is a little antithetical to what we just talked about, but it can't
solely rely on me if that makes sense. I'm still going to put those 18-hour days in,
but like I can't be a lynchpin in different aspects of the business. It has to be one
of those things where you know, if I die, like you know especially with a
background with cancer and stuff like that, like you know, it's interesting when
like I go to talk to other CEOs in CEO groups and stuff like that, how you know
in some companies and I don’t think it's necessarily because they're venture
backed, but then a lot of companies that have very high-pressure boards, you
know, because of different involvement and different leverage and things like
that, most of those folks will try to hoard as much power and leverage as they can,
and I think that I try to like dissipate as much power and leverage as I can. You
know, this whole concept of 'Servant Leadership,' to throw another tangent here,
mainly because I think that's the only way that we are going to continue to be as
profitable as we are and continue to grow and ensure that we are as efficient and
effective as we can be because we are building a machine, we are not necessarily
building you know, places for people to be placed into some of these problems.
So, I'm not sure if that's exceptionally clear or not, but –
Jerry: It feels super-clear and it feels super-interesting because what I think you are
doing is, you are – something I often feel like I do myself, which is, connect a
deeper philosophical point of view with a very pragmatic, on-the-ground
expression. So for example, your encounter with death, which you could argue is
really an encounter with life, meaning, it forces you to sort of clarify and really
think through your relationship to living, not only altered the balance of your
relationship with uncertainty and growth, but also leads you in a sense to create a
much more scalable, and by argument, much more efficient approach to
management. I mean, what you just described is the essence of a lot of one-on-one
coaching I will do with a CEO or I talk about 'Servant Leadership,' not necessarily
because it is ethically and morally more functional way, but it's also a much more
scalable model; the leadership to hire, empower and hold accountable a set of
really talented people, means that the work spreads throughout the organization.
And oh, by the way, if the leader is no longer available for some reason, death
being one, but fundraising might be another reason –

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Patrick: Yeah, all of the above.
Jerry: All of the above, then all of a sudden, the organization becomes something much
greater than any one individual. And I'm remembering a quote from Jay's medium
post where you said, "Nobody works for me, we're in this together. I want to build
something that can outlast me."
Patrick: Yeah.
Jerry: Is this an expression of what we were just talking about?
Patrick: Yeah, absolutely and I think you – I think Jay doctored – I sounded much more
profound there than I [Crosstalk] but I think it is – it aligns with that because I
think for me, like going down a little bit more of the 'Servant Leadership' thread
here, it's I was always very uncomfortable with like "you work for me" CEOs or
like people that I have encountered and I – I have heard more horror stories than I
have experienced, if that makes sense, I didn’t have like a too horrible of an
experience there but, I think that what I have found at least personally and keep in
mind, we are a 20% company, so this might not work with a hundred people, it
might not work at 500, 1000, etc, but I think what I have always found is, there's a
lot more power in 'our' as you have been insinuating, rather than 'mine' if that
makes sense and so it's been fascinating to see that play out because it does have
its problems because if you are trying to move extremely quickly and you have to
maybe debate something rather than "Hey, you have to do this" I think that you
might move a little bit slower, but if you hire the right people, put them in the
right place, put the guardrails up like you should, then they should just do what
they have been hired for. I get very uncomfortable with – and I know it's funny
'cause I said it as you know, in the sense that we are talking about, but I said as
"my team" before and as soon as I say that – any time I say that I'm like "oh, yeah,
you know, they work for Price Intelligently" or they work you know, whatever,
I'm get very uncomfortable, like you could probably roll the tape back if you are
recording the video and see like I kind of like jolted a little bit 'cause it's like, I
have to ask 'our team' and plus there's a little confusion 'cause people are like,
"What do you do there?" And I was like "I'm CEO." It's like, "So, it's your team"
and I'm like – it's a weird thing to like own up to it I guess, but long story short, I
think that's definitely a reflection of what we have been talking about.
Jerry: Well Patrick, I got to tell you that for years I've been extolling the virtues of what
I call the 'Upside-down pyramid' which is an expression of what we are talking
about here, and for years, I've added to that by saying things like, “The only way
to create a humane, scalable organization that allows every individual to realize
their fullest potential is that 'Servant Leadership' model, whereby there is no 'us'
and 'them.' There's no 'them,' there's only 'us.' There's no 'you' and 'me,' there's
only 'us.' And that not only creates a more efficient and effective organization and

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one in which people can grow, but from the CEO's perspective it's a hell of a lot
more fun.”
Patrick: Yeah, I think – yeah, it is. I would say – I think there's some –
Jerry: Sure, there's definitely challenges; I mean, you know like George Bush once said,
"There's a lot of efficiency in being a dictator."
Patrick: Absolutely.
Jerry: But it also all ends up on your shoulders.
Patrick: Yeah, and what's really fascinating is that I – so we talk to a lot of companies just
'cause of the nature of our work, you know, pricing is everything you do, leads to
your pricing or is used to justify your pricing and your business and when we –
and that means we deal with a lot of the CEOs and you know founders and stuff
like that of the companies who we work with, and it's almost – we can almost
predict, based on what we are talking about, like depending on like if the CEO
feels like he or she is the only one who knows anything, and like you know, any
data no matter how strong you put in front of them, it's like if it disagrees with
their assumptions, those types of CEOs, we could almost predict how things are
going to go, not necessarily with the project, with the company.
Jerry: How do things go?
Patrick: I think a lot like – I can't name the names, but a lot of them are out of business.
Jerry: Right. See, what you are confirming is something that I have been teaching for
many, many years is that this is the way to build lasting, sustainable companies.
It's not necessarily the way to build really, really seductively attractive products
that get acquired by big companies, but if what you really interested in is building
companies that are employing people a hundred years from now, this is what
you've got to do.
Patrick: Yeah, and I think it's – what's ironic about is that a lot of times, my peers, they
feel like doing the more, let's just say 'The dictator approach,' maybe that's a little
strong, but like doing a very top-down approach –
Jerry: Top-down, right-side up pyramid.
Patrick: Sure, I think what the problem there is, a lot of times you are not actually hedging
as much risk as you think you are because you are eventually going to break
down; like you know, if you look at the early-to-growth stage, you are looking at
what three or four years, and like you can't – you can't work 18-hour days for
three or four years or put enough time for a top-down approach and eventually
like, it's – you know, you have not admitted your ignorance, I also would argue. A

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lot of times, like, it's fascinating and I know some of these types of CEOs just in
the Boston community and I'll be hanging out and you know we'll be doing
something after work or something, just meet up, but the arguing – you know a
non-technical co-founder or CEO will be arguing about very technical things. And
it's not that they are incapable of making a decision there, it's more just like, don’t
you trust your CTO who has been doing that specifically? And what we always
say or what I always try to say here at Price Intelligently is that even if I know
more about sales than our top sales person, I'm not thinking about that 24-7, he or
she is thinking about that 24-7. So I'm always going to 'speed bump' them and
that's what we call, which is basically like "Hey, I might disagree with this point
or what do you think of that?" but he or she is always going to have the final word
because they are going to live or die by their performance. Long story short, I
think it's – you know, there's some advantages, disadvantages of both, but we see
more of the failures are, you know, are risked even higher because of the type of
leadership style
Jerry: And I saw you do something just very subtly, which I think is really important,
not only did you know the capacity to speed bump things, but you talked about
who ultimately has the responsibility, which is the domain owner. But you did
something very subtle, but very important, which is by talking about giving that
person the ultimate authority, an agency over the decision, you also noted that
they are going to be held accountable 'cause they are the ones who are going to
live and die by the decision.
Patrick: Yeah.
Jerry: And you know, too often, when people try to go for this more scalable model,
staff tend to enjoy the empowerment, but are frightened of being held
accountable.
Patrick: Yeah, which is tough because if you have the baked in – and what is great about
that is that de-risks my job as well.
Jerry: Yes.
Patrick: Like, when I go to the board and it's like these numbers aren’t working, like,
maybe if I trust this person too much and you know, they continue not to work
then it's on my head, but it's more like, "Oh well, if it's not working then let's get
rid of that person and replace them or do something like that." But I think that to
your point, I think – and that's what you see in a – I don’t want too much of like
Tony Shea and Zappa [Inaudible 0:44:47] holacracy and stuff like that, but I
think that you know, if we had to look at the spectrum, that might be way too far
on the other side of the spectrum.
Jerry: Yeah, I think so.

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Patrick: Yeah, and I'm not totally up on everything with that, so I don’t want to speak too
much to it, but I think that from my end, it's like accountability isn’t like a big,
central piece of it, like true accountability, because there's not really any boss or
structure and you know, there's goals but they are not quite – there is not teeth
necessarily in them – I might be getting it totally wrong so hopefully I don’t get a
bunch of mean tweets about how I don’t understand the holacracy and stuff like
that, but yeah, I think it's definitely a different side of the spectrum.
Jerry: And you know, I think that again, I heard you parsing the responsibility, what I
think is correctly you know, I spent many years as board members and over the
years, probably served in hundreds of boards of directors and you know what you
said was, it de-risked your job as CEO when you created this kind of twinning of
empowerment and accountability. I think you are absolutely right, but it didn’t
entirely de-risk it.
Patrick: Sure.
Jerry: That is to place the risk exactly on where it is; your job is to actually to build the
right team and if you make a mistake there and do not fix it, then your job is on
the line.
Patrick: Well, the buck ultimately stops with me right? And I think that's kind of like – so
little bit of the risk in this types of model too which is like especially coming from
someone who is – the martyr complex or whatever, putting the team on your back,
"I'll just do it, you know, I'll put the extra hours in rather than like you know
scaling this" that conflicts with the whole concept of like all right, I'm going to
trust this person. Trust is a huge thing with this; it's like I'm going to trust myself
that I hired the right person and I'm going to trust this person to do their job and
you know, it's definitely like, I'm not going to pretend that there were no growing
pains with this type of a model at all. I think every main exec that we've hired, it's
been a little bit of trust-building. It's been a huge aspect to like trust that things are
getting done and me being able to like, put the trust on them as well.
Jerry: Yeah, well, but I think – I don’t think we ever started talking about what's the
easy way to build a business.
Patrick: Yeah.
Jerry: We were talking actually about the more effective way to build a business; that's
what we have been talking about. So, we only have a minute or two left, I'd like to
just sort of jump to what I think might be a good punch-line, which is, so how is
the business doing?
Patrick: Yeah, that's a great question; there's a lot of ways to answer it. We are doing well,
we – sort of profitable, I mean, because we are self-funded, we kind of have to be,
and so we – without going like too deep just 'cause we only have a minute, we

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started the business as a pure software company, we realized we could extract a
heck of a lot more value if we coupled our software with our expertise and that
really – that's when things kind of took off. And so what we then did is, our goal
now after kind of doing that model for two years is how do we get back to more
scalable pure software and we have essentially been doing that with this product
called Profit Well. So, things are awesome, in terms of – we are 20 people, we are
able to pay people decently, we are having a good time, we are also very serious
about our goals, and we are hiring in a good clip and so, without doing the
numbers game, that's essentially where we are at, and I think for us, kind of taking
a step back and in a more general sense, I think it's – like any business, we have
our challenges and so like I feel like the proper answer to that question when you
go networking is, "We're crushing it, everything is going well," which is like, oh
great.
Jerry: I hate that answer; I always say that is the bullshit line.
Patrick: Oh my god, and when you see it on like videos and stuff, I always cringe. I think
for us though, we are legitimately – like, we know the path, we know where we
are, and we have some wind in our sails. I think there is a little fatigue in a few
places and we are working to like fix that fatigue because there's a lot of problems
with being self-funded. There's a lot of issues with like, well, money is coming in,
but like you know, what if it doesn’t and you don’t have necessarily that huge
coffer, especially when you are trying to grow aggressively. So, you know, we
were not running against the rails, but we were trying to hire to a point where all
of a sudden, we have to hit our numbers because if we don’t, we are going to have
to let some folks go, which we want to avoid. And so yeah, long story short,
things are going really well, we have definitely some problems that we need to
solve, which hopefully is how everyone is, in terms of the businesses.
Jerry: Well, Patrick, I can't thank you enough; what a delightful conversation. You
really epitomize in so many ways, the things that I believe are really important
about leadership and I appreciate your willingness to open up and talk about the
journey, and I know the folks who listen will be grateful as well.
Patrick: Awesome, well this has been great for me as well, so thank you so much – not
everyone will ask these types of questions. They want to talk about pricing and
you know, what advice I can give them, and this is a little bit more reflective. So I
appreciate your time as well.
Jerry: Thank you so much.
**
So, that’s it for our conversation today. You know, a lot was covered in this episode from links,
to books, to quotes, to images; so we went ahead and compiled all that, and put it on our site at
Reboot.io/podcast. If you’d like to be a guest on the show, you can find out about that on our site

17. Reboot037_Servant_Leader
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as well. I’m really grateful that you took the time to listen. If you enjoyed the show and you want
to get all the latest episodes as we release them, head over to iTunes and subscribe and while
you’re there, it would be great if you could leave us a review letting us know how the show
affected you. So, thank you again for listening, and I really look forward to future conversations
together.
[Singing]
“How long till my soul gets it right?
Did any human being ever reach that kind of light?
I call on the resting soul of Galileo,
King of night-vision, King of insight.”
[End of audio 0:52:28]
[End of transcript]