Reclaiming Our Shadow Selves

Reboot028_Reclaiming_Shadow
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“– and especially as a founder based in San Francisco, you hear a lot of stories of greatness and
you don’t hear the stories of struggle; and so, I thought that I was only allowed to feel greatness,
and that struggle was something that you don’t talk about.”
Welcome to the Reboot podcast.
“The shadow is everything about ourselves that we do not know or refuse to know, both dark and
light. It is the sum total of the positive and negative traits, feelings, beliefs and potentials we
refuse to identify as our own. The shadow is that part of us that is incompatible with who we
think we are or are supposed to be.” – David Richo.
People will often ask, “How is the podcast doing?” I know what they’re asking. They want to
know the data. They want to know the numbers. How many downloads? How many reviews?
But I answer this question a little bit differently. I say, “Yes, it’s doing great; but not because of
the numbers, but because of the impact.” Nothing is more rewarding, nothing more moving than
hearing from our listeners on how the show has helped them. What’s even more rewarding is
getting to know some of the listeners, following their growth and ultimately having them come
back and share their story with you. We’re very fortunate to have just that for today’s
conversation.
Tracy Lawrence originally reached out to us about a year ago, about the podcast. She said it gave
her permission as an entrepreneur; permission to feel, feel the ups and the downs. It kick started
her relationship with Reboot, and we have been fortunate to support her on this powerful journey
of self-discovery and authentic leadership. We are so thrilled and grateful to have her on the
show with Jerry. Tracy and Jerry talk about authenticity, leading from the heart and on the power
of embracing the lost and disowned parts of ourselves. For Tracy, it’s not only about being there
for the little girl who was bullied in middle school, but also about owning her own inner bully.
Reclaiming that part of herself would not only impact her approach to the latest company
experiment, but it also might affect her own leadership and bring her and her company deeper
into alignment.
As a quick reminder, if you want to see notes along with top quotes or links or anything
mentioned here, you can head on over to reboot.io/podcast.
**
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**
Jerry Colonna: Hey Tracy, how are you?
Tracy Lawrence: I’m great. How are you?

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Jerry: That’s good, that’s good. I’m great and I’m super excited to be talking to you
again, and before we sort of tell a little bit of a history of how we’ve gotten to
know each other, why don’t you take 10 seconds or so and tell us who you are?
Tracy: Oh man, who am I? That’s a great question.
Jerry: Well, not in the full coaching sessions.
Tracy: I only get 10 seconds?
Jerry: That’s right.
Tracy: So, I am – I’m 26 years old. I’m here in San Francisco and founder of a startup
called Chewse, and we are an on-demand food startup and our basic goal is, we
feed offices their meals and we work with – we partner with great restaurants,
local restaurants in the city, and we take care of the delivery and the logistics of
sending them to great companies that we support.
Jerry: That’s great. Thank you. And you know, it’s always nice to sort of, land people
as, you know, who is this person I’m working with; and you know, to jump back
for a moment, I’m excited to see you again. You know, Tracy, I guess you first
contacted me because of the podcast.
Tracy: Yeah, that’s right.
Jerry: And we started having a dialogue back and forth, and I encouraged you to come
to the boot camp, and you blew us all away in the boot camp with your depth and
your soul, and your leadership and your authenticity and your capability. So,
when you agreed to come on the show, I was just super excited, like I’m jumping
out of my seat to make that happen.
Tracy: I’m both excited like in a tingly way. I’m also a little nervous. These sessions can
be really powerful and I’ve no idea what’s going to happen, but I found that this
show helped me unlock a big part of myself. So, I’m excited to share and see what
happens.
Jerry: Yeah, yeah, and you know, I’m glad you named that, you know, a lot of podcasts
are sort of, more, in my view, are kind of, in the head and part of why we really
try to have real deep conversations is that I think that people being able to listen to
that conversation, they’re helped by that. It sort of normalizes the experience that
we all have and – you’re nodding your head, so I imagine you’re in agreement?
Tracy: Yes, well I think, listening to the podcasts gave me permission, and great
permission to just feel the things that I feel, and especially as a founder based in
San Francisco, you hear a lot of stories of greatness and you don’t hear the stories
of struggle; and so I thought that I was only allowed to feel greatness and that

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struggle was something that you don’t talk about. So, one of the things that I
brought to the boot camp was that I had treated myself like software since I
started the company. You know, you give me an input, I will do it without
emotion and I will get it done and I will execute, but it caused me to cut off a lot
of myself; and that’s really hard to deal with.
Jerry: Yeah, now I’m remembering the wish that you had; do you remember that wish?
Tracy: The wish to not be software anymore?
Jerry: Yeah, yeah, see, I was thinking of it in a positive sense, as the wish to be human.
Tracy: Yes, that’s true.
Jerry: Yeah, and here you are, this incredible human.
Tracy: I’m human again. Oh my gosh.
Jerry: I’m human, look at that. Look at that. So, with that, my dear human friend, you
know, I know that you thought it might be helpful to talk through one particular
thing that’s going on for Chewse right now, and why don’t you give us a little bit
of background on what’s happening with the company and what you want to talk
through?
Tracy: Yeah, so we’ve recently raised our series ‘A’. We’re working with an incredible
investor at the foundry group; and so one of the things that we’ve implemented,
now that we have a little bit of space, is open compensation and a salary and
options formula. It’s funny, because it is the most – it feels like the most
vulnerable thing I have done all year; and I –
Jerry: More vulnerable than the boot camp?
Tracy: And funny, in some ways, yes; you know, the boot camp is a very safe space and
not to say that my company isn’t, but you know, here I am, setting compensation
and opening that up, and these are people’s lives and their livelihood; and you
hear a lot of people on the podcast where you have to reassure them about failure
that you’re not going to go hungry. Or here I am nervous about how people will
perceive, you know, other people’s salaries because it’s directly related to that
question.
Jerry: Yeah, and so, the issue is that you have adopted this policy of being open about
who’s making what, who’s compensated in what way and what options are
available and that sort of thing; am I understanding that right?
Tracy: Yeah, you know – so the reason that we started this, let’s start there, is, as you
know, as an entrepreneur, we’ve all done it where we have offered different levels

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of compensation to two people that have maybe, similar – very similar skill sets
because one person could negotiate better. You know, maybe even because we
woke up on the wrong side of the bed that day.
Jerry: Right.
Tracy: And I’ve seen that with engineers who don’t negotiate, I’ve seen it with women
who don’t negotiate, and it’s just a personal, almost ethical struggle. I didn’t want
to be like that. We call ourselves a love company, and when my cofounder and I
sat down and we thought about how we could best show love, we thought, you
know what, it’s by treating our people fairly and transparently. So, I think there’s
a very strong reasoning behind it, but it still scares like, the crap out of me, just
getting it right.
Jerry: Oh, so that’s the fear. The fear is that you won’t get it right?
Tracy: Yeah, and that – I mean, here’s the thing, it’s art and science; and we’re almost,
you know, we’re trying to bring a lot of science to it by creating a formula, but
there’s still always going to be art in the formula and that’s – the art, you know, I
want to get the science right. I also want to get the art right.
Jerry: Mm-hmm, there’s a software wishing to be human.
Tracy: Yes, that’s right. Showing love through a formula right?
Jerry: Yeah. So, right now, you’re in the middle of implementing this; is that right or
designing it? Where are you?
Tracy: So, we’ve actually – we implemented it in September, so it’s been almost two
months, that it has now been open; and we’re getting a lot of feedback on it; good
and bad.
Jerry: And tell me more about the feedback. Tell me more about the effect.
Tracy: Mm-hmm, yeah, so the – what we expected to happen, was that – we wanted
people to have difficult conversations with their managers. So, you know, I’ve
heard of stories where in most companies, you don’t talk about salary except to
your manager, but if you know other people’s salaries which invariably, it gets
talked about – I heard a story, a guy told me, someone brought up to their
manager, you know, “I was talking to my coworker, her salary is this, my salary is
this. What’s happening?” The manager fired her, fired the coworker. Right,
because they were like, “We do not talk to each other about salaries.” So, you
know, we wanted those conversations to get aired out. So, we’ve had, you know,
people come to us and – engineers come to us and say, “Wow, I make more
money than anybody in the company. I’m nervous about people seeing that.” You
know, we said, that’s a conversation we want to have, right? We want to be able

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to help people understand what’s happening, and why that work is valued at a
higher premium than other kinds of work. We’ve also had people come up to us
and say, “You know, it makes me a little uncomfortable. I have to admit it.” And
there’s no – there’s no solution for that right, except just showing them, you
know, that this is how we get you to the next level so you can, you know – in
getting to the next level that’ll be tied to compensation but there’s no solution.
And you know, I’ve talked about for me being in the grey area, and not having
things be black or white is terrifying. I want to wrap it up, you know.
Jerry: Yeah, and you want it clear, you want a formula.
Tracy: Yeah.
Jerry: Yeah, so just bring your attention to what is happening inside of you right now,
you know, just bring your attention in because what I’m feeling in this moment,
Tracy, is a pressure in my upper chest. Does that – is that mine or is it yours or
both of ours?
Tracy: I mean, you know how to spot these things. I think that – yes, I think, physically
like, I feel it. I feel it right at the heart, which is – which is a funny thing because
this is showing like, love. Right, this is meant to show love; and yet, I feel very
tense and nervous about it.
Jerry: Yeah, yeah. So, it’s a tender spot. It’s a scary spot; and there’s a wish that I can
feel. Is there a wish behind the intention? You and Skank, Skank is your co-
founder; actually, we can still call him Skank, right?
Tracy: We can call him Skank, yes, yes.
Jerry: Yes, that is his nickname.
Tracy: It’s his last name, for everyone to know, okay?
Jerry: That’s right, that’s right. We’re not dissing him. You and Skank – it’s Jeff, by the
way, right, feel there’s something really important going on here, isn’t there?
Tracy: Yeah.
Jerry: Now, if you remember, we’ve talked about some beautiful experiences, and I
asked you to explore, for example, the why behind the company, the purpose
behind the company, and we found a tender spot; and uh-oh, Tracy just got
nervous.
Tracy: You’re going to make me cry, that’s why.

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Jerry: Well, there’s a tender spot behind the purpose of the company which I’m going to
name it, if it’s okay with you –
Tracy: Yeah.
Jerry: – which is, it’s not just about feeding offices, it’s about getting people out from
behind their desk to sit together in community and share a meal; because
community means love. Am I naming it well?
Tracy: Mm-hmm, absolutely.
Jerry: Okay, so what’s the purpose here for you and Skank, behind openness and
transparency around the salaries and around compensation?
Tracy: So, for some context, our mission is to bring your heart to work, and a lot of it
comes from – so we’ve raised over eight million in capital and so that means a lot
of rejections. I’ve gotten a lot of rejections. One that hurts me in particular, came
from an investor who – before he had the chance to meet the team, he cut the
process off and he said – he said, “You know, honestly, I just don’t think that
you’re out for blood.” And it tore me up. It tore me up. They say as, you know, as
an entrepreneur, don’t take it personally. I took it personally.
Jerry: I don’t know how you don’t.
Tracy: So, I really had to dig deeply and so, a few days later, I wrote him back. This is
the email. I wrote him back an email and I said, “You know what? You’re right.
I’m not out for blood. I want to build a service and a company that people love,
that people love to use and that people love to work at, and so I’m not out for
blood.” And so I think the broader purpose behind Chewse is, I want to build a
template for a company that can prove that you don’t have to be an asshole to be
successful; that you can build a company that’s people focused and still bring
great returns, still hold people accountable to their goals, still have high
expectations, still make difficult decisions. But I want to prove that and so every
time that something goes wrong, it’s like I – it’s like I’m hurting the cause and it
feels very serious.
Jerry: And so the fear right now is that, if you and Skank and the rest of the senior team
don’t get this right, you’re hurting the cause.
Tracy: Yeah. We’re hurting the cause and there’s a secondary fear which is, I want our
people, I want them to be happy at work and I also want them, I mean – and this
maybe, is the more selfish cause, but, I want them to feel good about themselves
so that whether or not this works out, I want them to think well of us as leaders. I
want them to think well of me, and I want to work with them again and I would
be devastated not to work with them again.

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Jerry: So, I just want to hold on that for a moment. This is super powerful. It’s super
powerful. I hear such an incredible value statement, such a tender-hearted and you
know, in the language that we often use at boot camp, broken-hearted; broken,
open-hearted warrior stance.
Tracy: I think about it a lot.
Jerry: Yeah, and so part of what is so scary, is that the stakes here are, “Jerry, am I going
to fuck this one up?” Right?
Tracy: Yeah.
Jerry: So, I’m going to get a little paternalistic; you’re the same age as my son, you can’t
fuck this one up. You could only make it better than it is, but there’s no fucking
up attempting to be authentic and real, okay? The way you can backtrack is to rely
solely on the formulaic software. What I mean by this is, I get that what you’re
doing is radical and scary, and I’ll be honest, I don’t know if it’s wise.
Tracy: Plenty of people don’t think it’s wise.
Jerry: I don’t know. I don’t know if it is, and I don’t know that it’s not.
Tracy: Yeah.
Jerry: Okay, but here’s what I do know, and here’s what I do know that is wise;
attempting to lead from heart filled place always works out. If we defined success
in endeavors like this, as you’ve just defined it, we’re just creating a heart-filled
place where people work, regardless of the outcome of the company walk away
and say, “God damn, that was the best company I ever worked for and whatever
Tracy does, I want to work for her again.” You know I have the powerful care and
concern for you. You’re 26, you have a lot of companies in you. You have just
begun to set the world on fire and from my lips to God’s ears, Chewse succeeds
and feeds every startup in this country. But if not, holding onto this, you cannot
lose. Now let’s talk tactics for a moment though.
Tracy: Great, let’s talk then.
Jerry: What – have you guys said to the team as to why you’re doing this? What have
you said to them?
Tracy: So, the thing – one of the things that I – we’ve said is the thing we mentioned; so,
about providing more – just more consistency, more fairness, more transparency.
One of our values is integrity and one of the ways that we define that value is the
ability to have difficult conversations and provide open feedback. So, it actually is
also in support of our value structure. One of our other values is community, and
part of that is really providing that feedback in order to better the people around

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you. So, it’s for a lot of those reasons. It’s also – part of it is for hiring. You know,
we make a statement in hiring; hiring in the beginning of that – towards the end of
that process around the negotiation can feel very adversarial. I don’t know
whether we can always eradicate that, but we want a candidate to know very
clearly, and we tell them early on in the process that we have this formula. We
want them to know that we’re on their side, and we don’t want there to be this,
“We hold all the information and it’s a black box and you have no idea what
you’re negotiating against.” When you negotiate against a black box, you’re
taught, go as high as possible.
Jerry: Mm-hmm. Self-optimize.
Tracy: Yeah, right.
Jerry: Self-optimization does stand in stark contrast to community building. Right, so
you said these things, and how has that been received?
Tracy: So, we’ve had a range of reactions, you know, to be honest. We’ve had a range
from some people being like, “A little nervous, right, but let’s see where it goes”
before we opened it up, to sales people being like, “This is so standard. This is
how we work” to some people being like, “This is how the world should work and
I prefer it this way.” So, we’ve seen – we’ve seen a whole --
Jerry: To people being scared.
Tracy: Oh yeah, oh yeah, to people saying like, “I’m uncomfortable with people seeing
my salary,” to people saying like, you know, I don’t, you know, “What if it
creates unhealthy competition?” Those have been the range.
Jerry: Did you have anybody who said, for example, “I didn’t realize how underpaid I
was?”
Tracy: Mmm. We’ve had people at the lower end of the range say – we had one person at
the lower end of the range say, you know, “I’m a little uncomfortable with it, just
being at this end of the range.”
Jerry: Right, but they didn’t see it as a source of resentment?
Tracy: Not since I’ve checked in, but I’ll be doing another check in.
Jerry: Okay.
Tracy: But no, not at this stage. I think, if anything, to give just a little bit of context to
the formula, so the main variable part of the formula is what we call the output
level and so – and by the way, we borrowed a lot of this from Buffer. They have a
great blog post on it; from Tint, so, I had a lot of conversations about it, but our

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output level, that’s – we rated A to G. ‘A’ being totally green, ‘G’ being totally
unicorn, and so that’s the variable piece of it and so when you move to the next
level, there’s a multiplier on your base salary.
Jerry: I see, I see.
Tracy: So, what we’ve found that is healthy is that a lot of people look at their output
levels, and this can bring up the difficult conversation that can be a source of
resentment; which is, “How come my colleague got a higher level in the same
role when I didn’t?” Which is starting to become, “How do I get to that next
level?”
Jerry: Right, well that kind of tension does seem to generate good, healthy conversation.
You know, one of the things that is critically important, and one of the things that
I think most startups fail at is getting good quality feedback on a regular basis.
Implicit in this, is a mechanism for quality feedback if your managers are actually
giving the feedback.
Tracy: Yes.
Jerry: Right, and so that some – there’s a corollary here. It feels like there’s work to be
done.
Tracy: Totally.
Jerry: I’m going to check in on one other piece of this; what feels important to me to
explore is the degree to which people connect this not only with the value
statements that you’ve spoken of, but with the other implicit value statement
which is, we’re going to try some radically different things, right?
Tracy: Yeah.
Jerry: There’s an experiment going on here –
Tracy: Yes.
Jerry: And it may not work.
Tracy: Yes.
Jerry: And notice the – now, what feeling did you have when I named it as an
experiment?
Tracy: Sigh of relief?
Jerry: Exactly.

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Tracy: Like a balloon sort of, getting just a little pop –
Jerry: Exactly, exactly. I mean, that’s what’s wonderful. It’s like, you know, when you –
see, when we create a condition where we say something like, this is the new
thing that we’re doing and we’ve worked really, really hard in this, and here are
all the values-driven reasons why we’re doing it, there’s actually a false
confidence that the leader has when they convey that. And the false confidence –
you’re nodding so I think you recognize this, the false confidence is, “Shhh, we
know what we’re doing.” Actually, shhh, we don’t know what we’re doing, or we
aren’t sure; whereas in that bit for transparency and authenticity, if you opened up
even just a tad little more, and let’s name the fact that you’re being vulnerable and
open now with me and they’re all going to listen to this. So, guess what?
Tracy: Yeah, and here’s the funny thing because this is what Skank reminded me to say,
and in my memory, I passed over it, but he was like, let’s make sure, and we did,
this is V1 and it may not work, right? But I, in my eagerness to see the world
change and to get – you know, I want the world to be a better place today.
Jerry: I want them to be happy.
Tracy: Yes.
Jerry: Right, so – and this is what’s wonderful about a leader like you is that you do
genuinely, in your heart, want them to be happy, but be careful of holding on to
that as your written-in-stone objective Ms. CEO, because you are not the
functional atheist at the top of the pyramid with all of the answers, right? Skank is
right. This is V1. This is like, “Hey guys, come join us on this journey. We may
get this wrong, we may get this right, and we co-own the success or failure as a
team.” Invite them into the process – into owning the process. Hey, let us know,
how is this working for you? Not you as the individual necessarily, but what are
you thinking about this? You and the senior leadership team still reserve the right
and the responsibility to make the final judgment call, but relax the tension that
arises from, “I have to get this right.”
Tracy: Yeah; ‘relax’ that’s the operative.
Jerry: That’s the operative. Let – you know, involve the community even further not to
the point where there isn’t clarity where we design, you know, 35 different
compensation systems to meet the needs of 35 individuals, but you create one
organization that’s committed to trying things, that is – does this make sense?
Does this land for you?
Tracy: Yeah, yeah and it’s actually – I think it’s something – I’m realizing it’s things that
we’ve been doing a little bit of along the way, but I don’t give outsized
importance to. So, we have like, a monthly fire aside chat where it’s us gathering

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feedback, and it was one of the topics for discussion, and you know, we got some
real feedback from it. That’s what we wanted, but and yet for some reason I’m
sort of, hard to – you know, when someone comes to me and I feel prickly, and I
don’t want to feel that way. I want to feel open to discussing it. I want to be
something that the team does have –
Jerry: Yeah. So remember, when the porcupine puts their quills up and it’s prickly, it’s a
defense mechanism. It’s not an offensive maneuver. So, there’s a threat that
you’re feeling, right, and what’s the threat?
Tracy: Oh man, well, I can see – I can see many. The threat is people leave. The threat is,
my own thought in my own head that “Oh shit, they figured it out. I’m a first-time
founder and you know, fucked this one up.” There’s – those are some of the --
Jerry: Right. How about, “The threat that that original investor was right” that you have
actually be an asshole to be successful?
Tracy: I know. That’s the worst.
Jerry: That’s the worst?
Tracy: It is the worst.
Jerry: Right. And the truth is, this has no bearing. The success or failure of this effort
has no bearing on whether or not that investor is correct. There are two separate
things. I – what my statement would be, you should be an asshole if that’s who
you truly are.
Tracy: Yeah.
Jerry: Right? There’s nothing I can’t stand more than the asshole who’s pretending not
to be. Right, because we all know it. So, if you’re going to be an asshole, be an
asshole, and be that kind of leader but here is a little hint, Tracy, you are not an
asshole. So, you can pretend all you want, and you’re going to adopt the attitudes
of and the style of, but you won’t succeed. You know, for good or for ill, you
have no choice but to lead from your heart, because guess what, human being, all
right, the tin man has a heart already.
Tracy: Yeah.
Jerry: – and it’s as big as the world; because she built a company that’s designed to feed
people, to nourish them. So – I get the fear though. I get the fear.
Tracy: Yeah, yeah. I find that the functional atheism part is the part that my mind wants
to forget, but I think it’s the part probably, to hold on to here.

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Jerry: Right. So, we’re referring now, both of us are referring to Parker Palmer’s
concepts of the five shadow-casting demons. The ways in which our disowned
self, start to show up in the organization and one of which is this notion of what
he refers to as the ‘functional atheist,’ the leader who is the rock, who knows
everything, who must carry all of the burden and it’s all up to me.
Tracy: Yeah.
Jerry: So, tell me more about that Tracy.
Tracy: Well, it’s funny because I think, I’m reflecting upon that. I am afraid of being a
dictator or becoming a dictator, but really I think I am afraid that inside, I am one,
and that I –
Jerry: Because you are.
Tracy: – have done a lot of stuff to cover it up.
Jerry: Right, because inside of you there is a dictator, isn’t there?
Tracy: I guess so, but I don’t like to hear – I don’t want to hear that.
Jerry: Well, just like at the camp, here we go. Just like at the camp, you wanted to
disown the part of you that was hurt when you were a kid, right?
Tracy: Yeah, that’s true.
Jerry: I won’t reveal too much about that.
Tracy: I’m happy to talk about that.
Jerry: Well, just like that, there’s also a part of you that is a dictator; and that part knows
the product better than anybody else, doesn’t she?
Tracy: Mmm.
Jerry: Oh, you don’t want to hear that.
Tracy: No.
Jerry: No, but Jerry, I want to be the one who leads from love. Right, so what – so tell
the story – if you’re comfortable, tell the story about the shadow that we talked
about, and then, I want to talk about embracing the shadow.
Tracy: Okay. So, when – one of the things that I recognized at boot camp and you know,
for some context for anyone who hasn’t been is, you know, it’s four days of just –

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Jerry: Crying.
Tracy: Crying; yeah, 15 of us together, crying. Four days, and you know, day one,
someone says something, it sparks a thought in you; day two, you say something,
it sparks another thought in you and a thought in someone else, and all of a
sudden, by I think, day three or four, you know, I am – someone brought up the
story of bullying. So, when I was ten years old, I had spent about three years
eating lunch alone in a bathroom stall and I was bullied. The way I had
approached myself with that is, you know what, this was in the past. Don’t even
get – you’ve got to move on. You’re an adult, for God’s sake. Then I realized of
course, I lunched alone in a bathroom stall and now I’ve built a company that
brings people together over lunch; and so there’s so much of me that is wrapped
up in this company, but is – there is also that fear of being that bully.
Jerry: So, let’s hold onto that for a second and let’s recognize that you embraced that
part of you; the part of you that had been bullied that was – that was “In the past
and let’s not deal with that anymore. We’re going to move forward.” And what
happened after you embrace that in terms of your capacity to execute in the
business? What happened?
Tracy: Well, I came back from boot camp and I shared with the team, that story and
some – I came into alignment. I came into alignment, and we all rallied around
being a love company and it wasn’t even – like, it didn’t feel like such an
intentional effort, I didn’t put time on the calendar, and say, we’re going to be a
love company, but just the souls, these amazing humans that I worked with, they
picked up on it and they carried it as a banner. Literally our flag – it is literally in
the Chewse logo; a heart and I felt like I’d never seen it before. And I looked at
my logo when I got back from boot camp, someone pointed out, they were like,
“Did you know we had a heart in the logo?” I was like, “Oh shit, no, I didn’t
know that.”
Jerry: Right, right. Now, I don’t think it was a direct correlation, but then if I recall
correctly, you were able to raise money.
Tracy: Yeah, and oh yeah, I forgot that part; yeah, you know, when I sat down to the – to
lunch with our now investors, The Foundry Group, one of the first things I said, I
was like right off the bat, I’m like, “Listen, I want to let you know that our vision
is to become a love company, and to be a template for other companies that want
to function this way, and still be high-performing, high-profit companies.” And
immediately, you know, I’ve got a text right after lunch, and Jason and I sat down
and he was like, “You are our kind of people.” And I’d never – I’ll never forget
those words. I’ll never forget it.
Jerry: He wasn’t looking for somebody who was out for blood.

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Tracy: No, he wasn’t.
Jerry: Right, so that’s a beautiful story, and it will stand forever in my mind as an
example of someone who embraced their shadow, but the thing about shadow is
it’s not just one thing. And so there is a part of you, just like there is a part in me,
Tracy, I’m a kid from Brooklyn, I can bully with the best of them. And so there is
a part of you that is strong in your belief system, isn’t there?
Tracy: Yeah.
Jerry: And sometimes you get a little afraid of that part of you, isn’t there?
Tracy: The – because this is to me – this is to me, trying to embrace like, I call it in my
mind, goodness and badness and the parts of me that are in the bucket of bad, I try
to push that bucket into the corner of the room and forget about it. But I can’t
throw it out because it just won’t – it’s not allowed to leave. So, it’s a struggle.
Jerry: Right, and so remember part of the lesson of embracing that shadow parts of
ourselves is, it includes the negative parts of ourselves. See, what you were doing,
you know, prior to the boot camp was putting into the past, the pain that was in
the – that was in the shadow. Now, there’s something very powerful in the part of
you that is kind of bullying, okay?
Tracy: Yeah.
Jerry: And we’re going to hold onto this for a second. When we take the parts of
ourselves and disown them, what Carl Jung said is, “Disowning the shadow is like
trying to get rid of a headache by beheading ourselves.” Okay? It doesn’t work. In
fact, it’s a kind of cutting ourselves off from something that’s really actually
neither good nor bad. It’s just distraught. Tell me about – tell me a quality of the
bully. Tell me some qualities of a bully.
Tracy: Ooh, so, psychological manipulation or emotional manipulation to get what you
want, but letting other people feel like they’ve got what they want, being a –
steamrolling others. I’ve been given that – I’ve been given that feedback before;
steamrolled people, and all of a sudden, I kind of, jump back and go, “Oh my
God, I can’t ever do that.” I’m extroverted. I’ve got sort of – my Dad’s from
Brooklyn, so you know, I’ve got a New York personality sometimes.
Jerry: You’ve got a problem with that?
Tracy: I’ve got – I don’t fucking have a problem with that.
Jerry: I have a fucking problem. You want to step outside?

Page 15 of 20
Tracy: You know, there is a – there is a feeling in your head, of superiority. I am superior
to you, either in intellect or smarts, anything; emotional – EQ even. There’s ego.
Jerry: There’s ego and there’s EQ and the ability to read people, isn’t there?
Tracy: Yes, but for bad as opposed to for good.
Jerry: Okay, so now we’re onto something here. Okay, every one of the qualities that
you just described can be described in positive attributes or negative attributes,
right? Ego can be equated to confidence, right? Manipulation can be equated to
inspiration, right? When Barack Obama inspires me with incredible speeches, is
he manipulating me? Damn right. The issue, the whole issue, Tracy, turns on
intention. It turns on the intention, not on the action.
Tracy: What if you have multiple intentions, or subconscious intentions that you don’t
even know about?
Jerry: Remember that radical self-inquiry tool?
Tracy: Mm-hmm.
Jerry: When you are disconnected with your truest intentions, the capacity to do evil or
to do ill with these capabilities is exacerbated. When you surface even the most
negative attributes, when you surface your own intention, are you ego-
aggrandizing? Absolutely. You’re an entrepreneur. But are –
Tracy: I know. Shit.
Jerry: But are you also selfless? Yes, you are. You are both. As Walt Whitman said, “Do
I contradict myself? I do. I am large. I contain multitudes.” Every entrepreneur
contains multitudes. Every human contains multitudes.
Tracy: Yeah. That – and that – it’s that part that I – now that I’m surfacing that, I don’t
know how to hold it and I fear letting – fear losing control of one side of that over
the other; the negative side of that.
Jerry: Okay, hold it without judgment. Hold it without judgment. There is a strength in
you. When you were bullied as a kid, they were bullying to protect themselves.
They were bullying because they saw the world as a threatened place. Okay, when
you hold yourself with firmness, it’s not necessarily bullying. Now, it could be
bullying. We don’t know. It depends on what the intention is. My famous
example of this is, a man plunges a knife into the chest of another man. Is it a
good act or a bad act? Before answering, know that he’s a surgeon. Before
answering, know that he’s still robbing someone. It all turns on intention, right?
So, embracing and acknowledging this part of you, are you strong willed?
Absolutely. Are you stubborn? Absolutely. Are you persistent? Absolutely. The

Page 16 of 20
question I would ask you, because you said it – you said it well, you said, “What
if there are multiple intentions?” Meaning, what if there are ego-aggrandizing
intentions as well as altruistic intentions? You want to know the secret? There
always are. There’s always – there are always multiple intentions behind our
feelings and the only way out is radical self-inquiry. It’s that self-awareness. So,
that you can pull out. Have I bullied people? Yes. I’ve typically bullied people in
defense of other people. Not always, but don’t – you know, my partners at Reboot
are sick and tired of me saying stuff like this, but don’t fuck with my people. You
want to poke – you want to poke the bear? Fuck with my people.
Tracy: Yeah.
Jerry: And by the way, the net of who are my people becomes larger and larger as I get
older and older. Right, you are my people. Don’t fuck with my Tracy, right,
because I will take you out. Is that a bully? Absolutely. Does that ego-aggrandize?
Does that feel good? Yes. And on the whole, I’d rather live in a community where
people say about one another, “Don’t fuck with my people.” Does this resonate
with you?
Tracy: Yeah. You know, so I was in Israel last week, and we learned – we learned this
great Yiddish word called ‘Mishpuha’ and people around me have been, you
know, I’ve been mishpuha-ing them all week, but basically what it means is, its
family, but it’s also extended family. And so you can use it to describe your
friends, your close friends and all of a sudden, I came back and I looked at this
team and I said, “You are my mishpuha,” right? And there is something that is –
that I want to fight for that is here, that is more than just runway.
Jerry: Yeah, yeah. So, you’re homework assignment with regard to both openness
around the compensation and this, is to lean into even further, the authentic nature
of it. When you tell people, “You are my mishpuha,” let them know that
sometimes, you are going to end up being paternalistic or maternalistic; that
sometimes you’re going to end up being ego-aggrandizing and sometimes you’re
going to be – end up being altruistic and compassionate. True authenticity is about
embracing even the parts of ourselves that we do not like, and dancing with those.
You know, as you’ve heard me say other times, it’s like a 10,000 Volt power line.
Right, you can pick it up and you can electrocute yourself, or you can pick it up
and plug it in and light up the city. Pick it up. So, there’s a part of you that’s a
Brooklyn bully. No wonder I loved you. That’s right. You know what I mean
when I say, don’t mess with my people.
Tracy: Yeah, totally. And that – it’s funny because there is a part of me that in embracing
that side, that sort of, that side that you can label good, you can label for evil,
there is excitement, there is energy in that.
Jerry: Yes.

Page 17 of 20
Tracy: You can just – you can just feel it, right? You know, I once – like last – a few
weeks ago, I just let myself be angry for a whole day and boy, I mean, I could
have punched a wall and I didn’t, but I just felt angry and I – and I was energetic
and so I think there is a way. I think ‘dancing’ is a really – it’s a weird, but great
word for it, because you can’t just completely act unfiltered but you have to – you
have to play with it. You have to let it out to play.
Jerry: That’s right. That’s right. You have to let it out to play; the anger, the frustration,
the frustration with the world as it is and how it is not what you want it to be. That
power is an awesome power. That power of so many entrepreneurs. Why the hell
do you guys work so hard if not to change the world from what it is into
something you’d like it to be? Right, and sometimes, in that power, you’re going
to tap into what other people, what you yourself may label as a negative force. It’s
only negative when you operate from a place of disconnection from your true
feelings.
Tracy: Mm-hmm and I felt that. You know, when I was fundraising, the – this links me
back to this feeling that I had when I was fundraising, and even for a few months
after, even a bit today, lacking the feeling, and the word that I used to describe it
is feeling vibrant.
Jerry: Yes.
Tracy: Seeing the whole color spectrum, feeling the whole range; because it was like, I
need to control this emotion because it was sad, and I was sad, and I just didn’t
feel the whole range, the emotional range. I didn’t – I felt like I didn’t see colors, I
didn’t see depth. I still feel like I’m kind of coming back from that.
Jerry: Yeah, so the – accessing that vibrancy of aliveness, right? It, you know, the
mistake is to think that we’re going to step into this kind of work, this self-
awareness work, this discovery work and that we’re going to make everything
good.
Tracy: Yeah, right.
Jerry: Right, and peaceful There’s a power in those rough edges. There’s a power in the
conflict. If you have an organization that is truly built around love, then even
conflict is acceptable because the totality of everybody is acceptable. Now, how
someone handles the conflict is a really important thing. So, “I’m angry” is very
different than me annihilating everybody around me. Okay, to me the truest
asshole is the one who is so disconnected from their deepest feelings that all they
do is like, spray bullets of anger against everybody.
Tracy: Yeah.

Page 18 of 20
Jerry: Right, whereas if they say, “God damn it, I hate it when the competition beats us
to these things. What can we do as a team to beat the competition?” That’s not an
asshole. That’s vibrant energy.
Tracy: Yeah, that’s a self-aware person too.
Jerry: That’s right.
Tracy: And that’s where, you know, sometimes I’ll look at – I’ll direct anger and go,
“Why am I angry about that? I’m not actually angry about that. There’s something
else.”
Jerry: That’s right. Well then that’s that radical self-inquiry. That’s that self-awareness.
So, another thing that I would suggest and I’m sure that as they pull the notes
together for this podcast, we’ll talk about a wonderful book, ‘Embracing the
Shadow’ by David Richo, really learning how to access even the negative parts of
ourselves because everything that is bad is actually really for the good.
Tracy: Yeah, and what I did find in is when I faced that image of me eating lunch alone,
and when I was able – and as I was fundraising, I would actually – I would
imagine it, some fun NLP stuff, but I would – I would actually look at it. I would
look at that image of myself and I would embrace that; that 10-year-old and I
would actually walk around of the bathroom and I would take her down the street
and you know, I would buy her a pastry, as a good friend of mine suggested I
think about. And in that, I did that before every single fundraising pitch, because
it unlocked something in me that I still can’t really describe except for these like,
that 10,000 Volts that – that tingly, that something on the edge of excitement and
anger and rage and creativity.
Jerry: And how old is the bully in you?
Tracy: I don’t know.
Jerry: Right, because what would be really kind of, cool is if those two little girls met.
Tracy: Mmm, oh damn, wow.
Jerry: Right, and you held both of their hands and that bully protected that other girl,
and together you took a step forward. That would be –
Tracy: That feels like the definition of alignment.
Jerry: Amen, sister.
Tracy: Yeah, wow, it’s a super powerful image. That’s cool, what a gift. Thank you
Jerry, it’s awesome.

Page 19 of 20
Jerry: Thank you, Tracy. You know, you, again and again astound me with your self-
awareness and your willingness to lead by example, and really put yourself out
there, and you are giving a gift to the Tracy Lawrences sitting there right now,
listening to this podcast.
Tracy: Yeah.
Jerry: And you’re telling her – if you could tell her something, what would you tell her?
Tracy: My gosh, I mean, the first thing that popped in my head was like, was about –
something about self-love, right? Give yourself a – give yourself a break. Give
yourself a hug.
Jerry: Yeah, give yourself a break.
Tracy: It’s just – it’s just that that little thing. Treat yourself, you know, 2015, but just
something for you. So, it’s kind of, nice to see it mirrored back because I’m not
always the best at doing that for myself.
Jerry: Me neither, me neither. Thank you.
**
A few words on investing in yourself and your leadership from –
Ben Uretsky, CEO and co-founder of DigitalOcean. We business leaders make so many
investments into our company and very few into ourselves, and if you think of yourself as a
leader for the business, then every investment that you can make into the leadership team, into
the co-founding team gets leveraged out so many times over the company itself. And think about
when was the last time that you made an investment in yourself, because I think what happens
when you become an entrepreneur is, you start to make countless sacrifices and investments into
the business that you’re building and you almost forget about the self. It’s important to realize
that the company is a collection of people on a unified mission, and sometimes you need to
reinvest back in yourself to actually accelerate the company.
You can learn more about our 2016 boot camps including co-founder boot camp, March 2nd
through the 6th, at reboot.io/bootcamps.
**
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
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

Page 20 of 20
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 0:57:12]
[End of transcript]

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