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“There’s a reason I am in this business and there was a reason I wanted to stay in this business.
I just wasn’t sure I was making the biggest contribution I could make, trying to wear someone
else’s loose shirt and khakis.”
Welcome to the Reboot podcast.
That statement from one of our guests in this episode, Bryce Roberts, not only made me a laugh
a bit, but I winced as I recalled my own blue shirt and khaki moment. I mean, literally, I was
wearing blue shirt and khakis. Between the summer of my freshman and sophomore year of
college, I wore blue shirt and khakis almost every single day. I cold-called my way into creating
an internship with a financial advisory firm that had never had an intern before. I thought it was
critical for me to get started early on the money-making path, and I knew financial advisors
made money, so I thought it seemed like a reasonable first step.
So, every morning, 6am, I threw on my [Inaudible 0:01:16] khakis and a long-sleeved blue shirt
and checked myself in the mirror. I remember vividly just how the pants and shirt hung off me
like a boy wearing his dad’s suit and I realized now, looking back, that was perhaps true. I
wasn’t just putting on the ill-fitting clothes my dad or others may have wanted me to wear, I was
putting on an ill-fitting life; not because going that career path is wrong, not at all, but it was
wrong for me. I was choosing to do what I thought I should do, what others wanted me to do
instead of what truly resonated with me and who I was. I didn’t know what I was supposed to
wear then, but I knew by the awkward, itchy boy looking back at me at the mirror, that I had to
wear something else.
Our guests today, two VCs, Bryce Roberts of OATV and Indie.vc, and Chris Marks at Blue Note
Ventures, also found the suggested outfit was not a fit for them. They both tried on the standard
issue of the VC world and found themselves like I did, each knowing they were wearing the
wrong thing. They both set out on a new path, one that aligned with who they are and what they
valued. In a conversation with Jerry, and each other, they explore the challenges of their journey.
Today’s podcast may leave you asking yourself, “In my own work, what are my values? What
are my priorities? What am I wearing today?”
**
Before we dive into today’s conversation with Jerry, Bryce and Chris, just wanted to remind you
all to head over to Reboot.io/podcasts. You’ll find quotes, links, and even the transcript for this
episode; and if you haven’t already, sign up for a free, five-day email course, Reboot Your 2016,
which contains audio-guided journaling exercises from Reboot coaches that will not only help
you reflect on 2015, but dive into 2016 in a new way. But before we start, a quick word about
our bootcamps.
A few words on investing in yourself and your leadership from:
“Ben Uretsky, CEO and co-founder of Digital Ocean. 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

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when was the last time that you made an investment in yourself. I think what happens when you
become an entrepreneur, you start to make countless sacrifices and investment into the business
that you are building and you almost forget about yourself, and 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 bootcamps at reboot.io/bootcamps.
**
“Be yourself, everyone else is already taken.” – Oscar Wilde.
Jerry Colonna: Hey Chris, hey Bryce, it’s great to see you again. Thank you so much for
joining the call today. It’s been a while since I saw both of you; I guess, Chris I
just saw you a few weeks ago, you are here in Boulder, but Bryce, I haven’t seen
you probably couple of months, a year?
Bryce Roberts: Yeah, we’ve talked on the phone, but yeah, in person, it’s good to see your
face again.
Jerry: Yeah, you too. So, let’s take a minute and introduce yourselves; Bryce, if you can
go first, and tell us who you are, and this will give the listeners a chance to sort of
separate the voices.
Bryce: You bet. This is Bryce Roberts, I founded a venture capital firm 10 years ago,
called O’Reilly Alpha Tech Ventures with Tim O’Reilly and Mark Jacobsen and I
am currently a VC and that’s pretty much it.
Jerry: Great. And Chris?
Chris Marks: Sure, my name is Chris Marks, I founded a venture fund called Blue Note
Ventures a little over a year ago, I have been doing venture capital for about 15
years, and I am here in Boulder, Colorado.
Jerry: That’s great. Thank you so much and you both have been friends of mine for a
while; Bryce a little bit longer than you, Chris, but I have always enjoyed our
conversations and really the explorations that we have had. I was excited about
the idea of getting, well, first of all getting two VCs in the same place, we’ll see
which one of you get to cry first, but, I was excited because I have been fascinated
with the endeavors that both of you have undertaken, on the one hand Chris, with
Blue Note and your thoughts around authenticity and authentic leadership and
Bryce, the Indie VC initiative and your thoughts about that. So, let’s, maybe by
way of just sort launching in, why don’t you tell us a little bit about what those
initiatives are and Chris, if you don’t mind, why don’t you go first and tell us a
little bit about Blue Note.

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Chris: Sure, as I mentioned, I started Blue Note a little over a year ago. Blue Note is an
early stage venture capital fund, we invest in great technology companies and
serve entrepreneurs committed to authentic leadership. So, that was kind of a
vision I came to after lots of thought around what I liked about venture and what I
didn’t like, what had worked over the last 15 years and what hadn’t worked, and
several uncomfortable coffee discussions with you, Jerry. That’s really where I
landed; I have been – I did a first close in the fund around the end of last year, a
second close a few months ago, we made our first couple of investments and the
idea there is really to model a relationship and an authentic set of values for the
entrepreneurs we work in the entrepreneurial committee in general and to identify
those entrepreneurs and those businesses that kind of fit that model in that mould.
Jerry: So, thank you for that and I am going to just jump in on that; so uncomfortable
conversation with me? I do remember a walk in Madison Square Park in New
York where I sort of kind of, called you on it; didn’t I?
Chris: Yeah, you did more than once. I think, it all started with you know, couple of
years ago, we get together maybe every month when you were in Boulder, and
we’d talk about Reboot and where we are going with that and then you’d say, “So
how’s the new fund coming?” And I think it was six months in a row where I
said, “Well, you know, I haven’t really started yet, it’s getting there, I’m thinking
about it” finally I think it was that sixth meeting where you looked at me and said,
“So what’s really going on? Why haven’t you started this?” The truth that you
helped me see is that I really wasn’t excited about doing just another venture fund
and so then it took a few more cycles and a little bit more conversation to figure
out exactly what I was excited about, and yes, that walk in the park in New York
was one where you asked me, I think, ten times in the course of that – we did a
few loops around that park –
Jerry: Yes.
Chris: – about ten times, why I wasn’t doing it, why I wasn’t doing it, and so, yeah, that
was helpful.
Jerry: Well, I remember that well and I’m really proud of the fact that, you know, as a
friend, I was able to just sort of, kind of jump in there and help you a little bit with
what I think is connecting to a deeper purpose.
Chris: Yeah, I agree, I appreciated the support; as always, you were there to ask the hard
questions and get to the right answers. So, it’s been an exciting ride ever since.
Jerry: So, Bryce, you know, I have the good fortune of being able to watch both of you
on video and I saw you staring at the screen, looking at him and kind of smiling;
what do you think of what Chris was just sharing?

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Bryce: You know, I think our business doesn’t really reward people publically for
thinking differently. I think, yeah, if you look at the people who really have had
an impact on the venture business over the last several decades, they are people
who took a lead and broke a mould and tried a different approach, and so
frequently in venture capital in the work that we do, our incentives are to keep
doing stuff that works and that’s been working, and dissuade you from trying to
do much of anything different than what you have been doing. And so I love
hearing from fellow practitioners, people who care about founders that they want
to do something different, that are willing to kind of put themselves out there and
take some risks. History suggests that we’ll get rewarded for doing that, so I – my
smile was, “a fellow traveler” someone who is willing to question the status quo.
Jerry: Yeah, and you know, if you don’t mind sharing a little bit of your own story with
regard to Indie VC because I see some parallels here, am I crazy?
Bryce: No, I don’t think so at all; I mean, you know, as we’re having this conversation
and you are accounting kind of how you two got connected, I am reminded of
how we got connected which was probably what, four years ago now, and that
was – you know, I was going through a pretty major decision point around my life
and my work and career, and there were a lot of really conventional opportunities
in front of me, to continue to run, you know, all of these, other opportunities in
the venture world that I was confronted with. It was during that time that I was
starting to really reflect on my years as a VC and my experience working with
entrepreneurs and recognizing that, you know, a lot of ways like, I was playing
somebody else’s game. And that was very eye-opening for me that there is a
reason I am in this business, and there was a reason that I wanted to stay in this
business. I just wasn’t sure I was making the biggest contribution I could make
trying to wear someone else’s blue shirt and khakis.
Jerry: Now, for listeners who don’t know, the blue shirt khaki uniform is well-known in
the venture business.
Bryce: Yeah, I mean, at the time we got connected, I was playing by the rules; I’d moved
from Salt Lake City, Utah where we had started OATV, we had moved to the Bay
Area, I was living in San Francisco, I have a big family, we were trying kind of to
come to terms with putting our roots down in San Francisco. As much we enjoyed
aspects of being in San Francisco and as much as we enjoyed the aspects of
working fulltime in San Francisco, it was just, you know, the body was rejecting
the organ and I was struggling with that. And so, it gave me an opportunity, I
think through our conversations, it gave me an opportunity to explore, okay, I’m
trying to play the game like everybody else is supposed to play it, and all these
years that I am supposed to doing the venture, I am doing exactly what people
told me I should do and I’m not happy. And so maybe I should jump to another
fund or maybe I should try something different. And I think what was – I think
what kind of set the course for the Indie VC stuff that you were referring to is the
difference that I chose was to be me and to try to embody through my work and

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my personal life, that I have always felt a relatively strong connection to who I
was, what I value, how I want to live my life, and I think at that point in my
career, I started in the venture business young, I had started to fund relatively
young, I hadn’t really given myself permission to own it and to be the boss and to
make decisions the way I want to make decisions and be held accountable for
those. And so, ultimately, I decided, this was back in 2012, I decided to move
from San Francisco back to Salt Lake City; so my family has been here since – for
the last three years and I think that move – really making that move and
recognizing that like, it was okay. You know, the investors came back for the next
fund, my partners didn’t bail on me, the companies didn’t flounder because I
wasn’t around, I wasn’t seeing less interesting – fewer things that were interesting
to invest in, but then by embracing that, it really, you know, kind of showed me
that as I – the more I embraced who I was and let that reflect in my work, that
good things happen. That made me think about it as, you know, I’m thinking a lot
about the founders that I work with and are they able to express themselves in the
most real, relevant way possible or are they kind of trying to fit this mould and
fortunately a couple of years ago, Aileen Lee from Cowboy Ventures gave it a
name: what were they trying to be? They were trying to be a unicorn; they were
trying to fit this profile of a company and profile of a founder and they would –
we’d study incessantly the moves that Zuckerberg and [Inaudible 0:15:31] and all
these guys were making on their way to creating massively valuable companies
and that became the pattern recognition. That became the really well-worn,
understood – that became the blue shirt and khakis. That became a very well-
understood way and not just understood but the way to being an entrepreneur. So
I started to wonder if that was healthy or if we could somehow – you know,
because when you look at the numbers, when you look at the numbers, 0.07% of
the companies in Aileen’s study had become a billion-dollar or a greater valued
company. So if you take that slice of entrepreneurship, which is actually a
relatively narrow slice in the grand scheme of startups and people who are trying
to launch businesses, if you look at that and you say, okay, applying those same
filters, applying those same values, applying the same focus, that VC tends to put
on an entrepreneur, will recognizing that that venture product and the way that is
constructed, it works for 0.07% of entrepreneurs who, as we know, it’s those
unicorn companies that drive all of the values that is created for the LPs that
invest in asset clients. And so, the Indie VC experiment was to say, okay, that’s a
pretty well-understood path, but it’s a relatively narrow slice and yet, those people
benefit significantly from the resources that a venture investor brings to
[Inaudible 0:17:06] and so you have these two worlds that aren’t connecting; this
kind of bootstrap, entrepreneur and this kind of, value added, networked VC and
yet, if you get on that VC track, it’s a very narrow path that you get to follow
essentially. And so, can we cast a net a little bit wider, could we open up – you
know, create a different funding model that said, we’re gonna give you – we’re
gonna release the pressure valve. If you aren’t a unicorn and you can’t reach that
kind of value in the next five to seven years, we have this option that if you’ve
created a business that you love, you want to continue to grow it, maybe you
don’t want to raise any more outside money, you can start making the cash

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distribution to us as your investment partner that we cap at a certain point. But the
encouragement is to build a long-term, durable business, not to focus on how do
you get to the next fundable milestone, because how many board meetings have
we sat in, you know, directly after someone has taken outside funding; whether
it’s a million dollars, ten million dollars, and someone at the table brings up, okay
what milestones do we need to have to hit to raise our next –
Jerry: To get to the next valuation increase.
Bryce: – to get to the next valuation increase, to be able to bring in that next amount of
investment dollars. and so after having watched that process kind of chew up and
spit out so many founders who I have really loved working with, and who
probably had some great businesses in there that just didn’t fit the mould, I
thought, let’s try something different. In the same way that I think differences
have – you know, people who try things differently have overly benefited here in
the venture world, I think potentially there is an opportunity to do that. So at the
first days this year, I put up kind of a landing page talking about this project, this
little experiment we did at a site called Indie.vc and kind of laid out a little of the
thinking. It was very raw, there was no indication of who was behind it, but the
day that I published it and it went live, so people started emailing about it and the
next thing I knew, it just blew up. So, where I was kind of expecting tens of
people to kind of find it and submit for it, we had 500+ people submit to it. There
was no press, no nothing, just you know, kind of spreading through people’s
networks and I think the opportunity for me, that you and I have talked about, and
that I think is really interesting is that we’ve tapped into something. I don’t know
what it is, but we have tapped into something and I think we owe it to ourselves to
play it out a little longer and see, you know, who else kind of rallies around this,
who else does this speak to and who can we help bring those ideas, those values
that they have into their businesses, that may or may not look like what a
traditional [Inaudible 0:20:05] investor would be interested in backing. So, that’s
Indie VC.
Jerry: So thank you for that. So, I want to connect these two thoughts and then expand it
because I think the two of you have done something really remarkable, and
notable which is that both of you have tapped into your own experiences, quite
frankly, to empathetically connect with entrepreneurs in a different way. Both of
you, in a sense, are calling for people to not wear somebody else’s suit, somebody
else’s ill-fitting suit and create structures to try to manifest that and see what can
happen, even if it’s not the traditional way of going about doing things. Am I
seeing this correctly? You are both nodding. Chris, am I seeing this correctly?
Chris: Yeah, I think that’s a good way to put it. I mean, breaking from the mould, as
Bryce was just describing is – it’s hard to do in this industry. You know, I
remember, Jerry, when we were talking about it, I think your line was, “When you
are standing at the urinal, just look straight forward.” It’s tough because you
wonder about the acceptance in this industry like anywhere else and you wonder

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what other people are going to say or how the market is going to react to it. As
Bryce said, you put something out there and then you just sit back and you wait to
see how it is accepted or not, but the comfort you can get in knowing it’s
something you are – that reflects genuinely where you are coming from, makes it
worthwhile and I think that you know, both of these – again, another thing that
Bryce was talking about that I can relate to is this idea of – and you know Jerry, I
looked a long time for someone to do this, for someone to kind of launch this next
fund with and what it comes down to at the end of the day is, if you want to do it
the way you want to do it, you want it to be reflective of your passions and where
you want to go. You just kind of have to do it and I think that’s how a lot of
entrepreneurs get to that point of staring over the cliff as well and taking that first
step can be the hardest part. You know, I know it was for me and it sounds like
Bryce gave it a lot of thought as well, but, I think that vein of kind of taking that
step outside the norm and doing it for something that we both believed in, kind of
runs through both those stories for sure.
Jerry: Yeah, I see that and having known the two of you, I knew that you were both in
parallel working through the same kinds of issues and you know, in a sense, I see
this parallel paths of each of you on a journey to find and manifest the true self.
‘Who am I really and how does that show up in the work that I want to bring
forward to the world?’ Normally when we think of that existential question, the
Hollywood picture is that you would each leave your business and go off and do
something. But no, it’s about actually reshaping the businesses that you were
doing in a way so that the suit fits better and that whether it’s Indie VC or it’s
OATV being run out of your home in Salt Lake, where you and your family take
precedence over playing the game, you know, or Chris you being brave enough to
actually launch your fund, kind of by yourself, with an investment thesis that is
not typical, where investment thesis is calling for the kind of a different approach
of leadership? We don’t know if these experiments will work out financially, but
that is not the calling to doing that seemed to be larger for each of you. You are
both nodding.
Chris: Yeah, I’ll just say, you know, in my past life, before I got into venture, I was a
corporate lawyer, I was a deal lawyer, and you know, I was taught that you do
that without any emotional connection to what you are working on otherwise it’s
dangerous and when I got into ventures, I’m sure, Bryce found in his early years,
it was much the same. The idea was to really let the spreadsheets do a lot of the
decision-making for you and kind of the relationship was really based on the
negotiation and the capital that got you involved in the deal in the first place. And
so breaking down some of that, you know, kind of the evolution of getting away
from that and kind of recognizing that the relational piece of it can actually be a
strength, and I do think it’s a strength, we don’t know whether these plans will
work out financially, but I wouldn’t be doing this if I didn’t think of it as a good
investment strategy at the end of the day. If any of my old peers are listening to
this, [Crosstalk] but you are right, I mean, the evolution away from the traditional

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model and the evolution away from what is known and comfortable had made a
lot of people lot of money and had been very successful was the challenge.
Jerry: Bryce, any response to that; any thoughts on that?
Bryce: Yeah, I think in this business, you got to process the risk a couple of different
ways; one is, you know, will I have support from investors? Will I have support
from LPs, and so with OATV, we built a great franchise over the last decade. We
have three funds, we turned away more money on our last fund than we took in. I
mean, it’s just been a great performing fund and we have been able to do well,
and I know Jerry, when you and I talked about it, okay, I want to kind of make
this pretty big transition, like there’s something here and I want to keep tugging
on it, and I need to give this Indie VC idea a little more space to kind of see what
it has to offer. I remember we talked about what could happen with the LPs and
you said, “Okay, what’s the worst they could say?” And I said, “Well, they could
say no and that would be pretty terrible.” “Well, what if they did? Would you not
do it?” They did say no. A lot of them said no actually with the transition and so
to go from a fund where you are turning away more money than you are taking in,
to a fund where you are scrambling to get, you know, even a handful of your old
LPs to believe in what it is that you are trying to do and the change you are trying
to make, and the impact you want to have and what that would mean in terms of
financial returns. They did say no, but you know what, some didn’t. And so now
we’ve got the real believers, now we’ve got the people who actually care about
this and are invested in this in a way and also it gives us an opportunity to go and
find the people who can be most out of there from an investor standpoint. So that
is the one risk; will they go away, will they believe in what it is that we are trying
to do and on the flip side of that, I imagine, Chris thinks about this a lot too,
which is, does what we are saying even matter? Do you know what I mean? Will
it attract the very best entrepreneurs or did the best entrepreneurs, are they just
going to go to [Inaudible 0:27:58] anyway? Did they just want to play the game
everybody else plays or, is there something about the way that we talk to
founders? Is there something about the way that we that we work, or we embody
values, or that we reflect those things in what we write, what we [Inaudible
0:28:13] what we say, whatever it is, will those signals, you know, transmit and
magnetize the right entrepreneurs, the founders who really want to have an
impact, the founders who can build big, durable companies with our involvement,
or will it scare them off? That’s the big [Inaudible 0:28:33] we won’t know for a
long time on that, but you know, my hope is, and I think what we have seen so
far, at least in our little experience, I don’t know if Chris is finding in his is that
yeah, the caliber of entrepreneurs is fantastic. I mean, I wrote a post recently
called ‘The Peace Dividend of the Seed Surge’ which was – we have had seven
times more founders raise a million dollars or more over the last ten years, and
many of those have felt now, what it means to take on piles of venture capital.
Seven times more people have felt what that pressure feels like. They have tried
to fit into that unicorn costume over and over again, and maybe they want
something different the next time around and you know what, when you look at

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Aileen’s study, it’s the second and third-time entrepreneurs who tend to be
making the big, breakthrough companies. And so if you look different, if you give
them an alternative path, maybe they’ll attract the right kinds of folks and I can’t
help but think that it will.
Jerry: What do you think Chris? What do you think about what Bryce has said?
Chris: Yeah, I would agree with that; I mean, both on the – I felt it heavily on the LP
side for sure; you know, when I would lay out my vision for Blue Note Ventures
in the leadership piece in particular, the reaction was always very obvious to me.
It was either resonating with someone, in which case the pitch would tend to go in
one direction, or it was absolutely not resonating, in which case I knew it was
probably not a great use to be there over time. And that was very hard for me at
first, for sure, when I was looking to get those first anchor LPs and I was
operating with the fear that it wasn’t going to get to a point where it could be real.
That was hard for me to stick to the script, but I did and much like Bryce, I think
at the end of the day, the people who are onboard are the true believers and
wanted to come along for the ride and wanted to be part of the vision. So, I was
excited about that. On the entrepreneur side, I absolutely believe that it will
resonate with the right people, and I think one of the primary drivers of that is
because of the entrepreneurs themselves that we have worked with. That
continues to be the best source of idea-flow and the best – I think for any
entrepreneur, I’m trying to understand what it is like working with an investor, the
best thing you can do is talk to other entrepreneurs they’ve worked with. I mean,
it’s out there, it’s available, it’s a real thing. Everyone has their own style, not just
the two of us; everyone is a little bit different in the way they do it, the way they
go about it, and you know, I’m a firm believer that if you stay true to who you are
and you interact with the entrepreneurs in a way that comes from your heart and
speaks to who you are, then that message gets out there.
Jerry: You know, I’m glad you shifted it, Chris, to that, because – and I’m going to
sound a little bit like your older brother, guys, ‘because I’m older than both of
you. This is – from where I sit, and I’ve been coaching now for ten years, the
number of entrepreneurs who speak to the same issues that both of you have
spoken to, and Aileen did us all a favor by giving us language around this
unicorn, but she did not identify something new. She identified a phenomena
that’s been going on, I think, as long as human beings have been together, which
is, this phenomena of ourselves pretending to be someone we are not and who we
pretend to be depends on different society factors. When I was coming of age as
an adult, it was pretend to be Bill Gates, and then it was pretend to be Zuckerberg,
and then it was pretend to be this one and pretend to be that one and pretend to
this one, and the result is this constant diminution of self to the point where
people walk around going, “Who the fuck am I? I’ve been pretending to be
someone else for so long that I have disconnected from who I truly am.” And the
pain of that – in Buddhism we call it ‘dukha,’ this existential pain of being just
disconnected in the truest sense of our own values. That is not a phenomenon that

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is limited to these times, to the unicorn times. Now I say this because – I’m going
to say something to you guys that I often say to other coaches who are just
beginning, this experience of pain that you both had, of trying to raise money
from LPs and facing rejections, of trying to do things differently, of trying to fit
and wear a different suit that is more fitting for you, do not forget that feeling.
The entrepreneurs are dealing with that every single day. And you get to have a
superpower, you get to have a distinct competitive advantage because you get to
know what it’s like to walk in their shoes, not in some theoretical way of “I
understand what it’s like to build a company” yeah, that is important because
you’ve both been entrepreneurs in your own way, but to get to know what it’s like
every day to have to make choices around family or friends or face rejection, and
that is an experience that I think entrepreneurs will resonate with because when
they come to my office and they sit on my couch and they cry, what they are
really looking for is a partner. You know, Chris, you started to say something
before you said “The entrepreneurs for whom we work – or we work for –” and
then you corrected yourself and you said “work with” but I think your first
instinct was spot on.
Chris: Right. Yeah.
Bryce: Jerry, how do we help them connect to that? You know what I mean?
Jerry: Yeah.
Bryce: Because as you know, the coaching-client relationship is different than a VC,
“I’m your boss” “I’m your board member,” “My job as a board member is to hire
and fire you” right? How do we give them a place, empower them – and that is
right, I mean you and I have gone back and forth on this a little bit which is you
know, I don’t come from an operating background. [Crosstalk] I’m not going to
be that board member who is saying, “Hey, I’m looking at your margins right
now, and I know like, this is going on or that is going on” you know, or “Hey, I
was in that – when I was a CEO I knew exactly how to handle this and here is
what you do” right?
Jerry: Right. Okay, so I’m going to coach you Bryce; what feeling do you have behind
the observation, “Hey I don’t come from that operational background, I can’t talk
to you about margins.” What feeling about yourself is implicit in that statement?
Bryce: That I don’t look like some other VCs and essentially don’t come from the same
background that people say you are supposed to have, to be super VC.
Jerry: Right and so therefore, you are inadequate in some capacity.
Bryce: Sure.
Jerry: Right, so hold on to the connection to that feeling.

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Bryce: Mm-hmm.
Jerry: I’m slightly inadequate, I’m less than.
Bryce: Mm-hmm.
Jerry: Okay, is it true?
Bryce: Of course not.
Jerry: Of course not.
Bryce: Of course not, and we both know the person across the table from me is feeling
the exact same way.
Jerry: Exactly.
Bryce: Right?
Jerry: Right, and so what you are really asking is, how do I help them or the first thing
we do and Brad Feldt and I talk about this a lot in the VC bootcamp that we are
going to do this spring, but the first thing you do is take care of your own internal
insecurities. Do not do the violence and project them on to the entrepreneur.
“Because I feel inadequate, I am going to over state what I am about to say and
get aggressive.” “Your margins suck.” “Well, what the fuck do I know? I’m just a
VC. I haven’t run a business in 15 years.” Right?
Bryce: Right. But I just read Fred’s post –
Jerry: Right, exactly and we are all –
Bryce: “You are supposed to care about your gross margins.”
Jerry: – laughing because we have all sat in those board meetings with a blow hard starts
talking. And so rule number one, get control of your own feelings, acknowledge
what’s going on. So, a simple thing is, “Hey, I don’t have any experience in this
particular area, but what occurs to me is this question.” One of the things that I
always observed is that board members tend to ask too few questions and make
too many statements. You know what I mean guys?
Chris: Yeah, I know what you mean. You know, when I first laid out the idea for Blue
Note Ventures, a lot of people would come to me and say, “Well, that sounds
great; how are you going to know who the authentic leaders are?” And I got this
very uncomfortable, queasy feeling in my stomach and that was the last thing I
wanted to be, was in a position of ordaining who was an authentic leader and who

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was not. And a lot of it came down to that very feeling and what I realized Jerry,
to your point, was, first things first, let me try and model what I wanted to be first
–
Jerry: God bless you.
Chris: – in terms of some of those traits that – and look it’s all aspirational. We can talk
about it all day long; I’m never going to be – Bryce is never going to be, Jerry you
are never going to be, although you might, I’m not sure, you might be one
exception, but we’ll talk about that another time. We are never going to all get
there, so the question is, along that aspirational journey, how can you model it.
And I’ve also found along the way is when you try and do that, it’s the quickest
way to get the entrepreneurs you are talking to and the entrepreneurs you are
working for, to go there as well. It creates a much safer environment for them, it
creates a much more open dialogue, and it kind of immediately breaks down some
of the barriers that create the exchange that you and Bryce were just talking about,
which gets nowhere fast.
Jerry: That’s right. So, I think you said it incredibly well; Bryce, to your question, you
know, how do we help, first understand what’s going on for you. What I often call
‘radical self-inquiry’ what the heck is – oh, my insecurity just got triggered. Now
I’m about to speak, in that moment I have a choice, I could be aggressive or I
could be supportive and generative in the relationship. Second, to Chris’ point, to
really connect back into the experience that the entrepreneur is having, what is
going on? I’m reminded of Thich Nhat Hanh’s quote, “Peace begins with me.”
Someone has to be brave enough to go first. Someone has to be brave enough, in
the middle of that board room, to say, “I don’t really have the answer, but here’s a
guess.” Create space. I could be wrong, I’m just going on a gut feel here, or “Hey,
I have four other companies in my portfolio, and I am doing that crazy thing that
VCs do which is pattern matching. Because I have four other companies,
therefore I think I know the truth.” The truth is invented every single time in
every single investment. There are things to learn that you can carry over, but a
kind of spaciousness around that and I think that the first way it happens is that
you have to get control of your own insecurity, which are constant and inevitable
and always there. I don’t know, does this resonate with the two of you? I could be
wrong. See what I did there?
Bryce: Yeah, I mean, as you probably experienced, often times, there’s two
conversations going on in the board meeting. There is the business of the board
meeting and then there is the show of the board meeting. You are now on a board
with someone who has a great investment track record, and you want them to see
you as just super sharp, and the next time you want to show them the thing you
are really excited about, they are going to lead it, you are going to look really,
really smart, your LPs are going to think you are really smart and you’ve built this
relationship there right in front of your CEO, right in the board meeting, by

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making that super insightful question about their margins. And those are two very
different things, those are two different –
Jerry: Well, I think –
Bryce: – conversations.
Jerry: I think you speak to another thing that investors can do to help the entrepreneurs,
just like CEOs can do to help themselves and help their staff. Don’t use the
organization to deal with your unresolved issues.
Bryce: Right.
Jerry: You know, Carl Jung said that the worst thing a parent can do is to ask their
children to finish their business for them. Well the worst thing a CEO can do is
use the organization to manage their unresolved issues, same thing with investors.
Don’t use that situation to prove that you know what you are doing as an investor.
Your first obligation is actually to return – to make a return on investment to the
share holders, which include the receptionist who is sitting on a few options, not
just your LPs. You are smiling and nodding Chris, you recognize this.
Chris: Yeah, I mean, it’s incredibly common behavior, as Bryce was talking about, the
two conversations going on, it captured some element of most board meetings
I’ve sat in for the last 15 years, so it absolutely happens. And even if you are
lucky enough to create a more authentic relationships with the CEO or the
founders, it often still rears its ugly head in certain settings like the board room,
where other people are involved and sometimes that can be just be inevitable. But
I mean, you know, getting to the point where you are today in your career, and for
me, there are a lot of little learning moments along the way, but one of them that
stands out as we are talking about this, which a CEO who I am still invested into –
with today, and he is building a great company, and it’s been a great pleasure, but
along the way there was a time early on where I felt like he was making decisions
for the company based on some personal things going on in his life and rather
than address that with him, I was – I was on the other tier of conversation. I was
trying to just point out how stupid the decisions were in the midst of the board
discussion, and thankfully, we had enough of a relationship underneath all that to
unwind it later and figure it out, and it really became an instructive moment to
me. And again, one of the impetuses behind where I went with Blue Note, just
because it happens all the time, it’s just human nature, it’s just inevitable, and you
know, I guess, one of the things I try and do now early on when I’m talking
entrepreneurs again is really understand why they are doing what they are doing.
We have talked about why we are doing what we are doing, why are they doing –
and there is always a business reason, market opportunity, this and that, but why
else? I may agree with it or I may not, but at least I know what it is and then I can
help put the decisions that are being made in that context and they need to be. To
ignore it is to just ignore you know, a really powerful force in the CEOs life and

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you can’t help him with it or her with it, or you can’t – you know, you are just
limiting your effectiveness if you chose to ignore that side of it.
Jerry: I think you just named something also that is equally powerful here, which is, by
having done the work yourself and connect it to your own sense of purpose, “why
do I do what I do,” It opens you up to ask that question in the relationship,
whether it is a potential investee or it’s a potential, or it’s an existing CEO. It’s
really powerful and as many folks who have listened to the podcast know, one of
the things that I often encourage people to do is connect back to those underlying
psychological forces at work because they tell us a lot, and if we surface them,
they really a great source of power. I did not know this at that time the story I’m
about to tell you, but it does recall something for me which was, in the early days
at Flatiron, everybody is trying to copy everybody else’s business model and this
one guy came in pitching his company and what it was basically a Yahoo-like
service. The only difference was that every time you opened up the home page,
that pinged – the server was registered and you got entered in a contest and you
got to win 10000 – every day somebody would win 10000 dollars. So, basically
what he was doing was buying traffic. And I remember being so repulsed by the
business model, it was – there was not a single value-add to the experience except
appealing to this notion of you know, make it your home page and every time you
open up your browser, you get entered in to win. And I said to him something
really, I think, important, and I said, “Why are you doing this business?” And he
said to me, “I went to business school and the people I went to business school
with – I am much smarter than they are and the people I went to business school,
a whole bunch of them have launched internet businesses, and they are wealthy
and I want to be wealthy too.” And that was his reason and I did not fund the
business. But now that I have been a coach for so long, what I would have done is
talk to them about the sense of inadequacy that is implicit in that, and said that
perhaps there is a different way to approach that sense, than just trying to mimic
and prove himself as smart as his grad school classmates.
Bryce: I have the flip side of that.
Jerry: Tell me.
Bryce: So, I met this entrepreneur which was – similar situation, got turned off you
know, by – less about what they were building just kind of more their ethos. Long
hair, kind of pony tail, said he was day-trader, wasn’t – had like all of these really
clever spins on what he was building and really sold himself as this kind of savvy,
stock-trading, day-trading kind of person. I was really turned off by the whole
veneer of what was going on, but I didn’t take the time, like you did with this
entrepreneur to kind of peel back those layers and figure out what was going on.
So, many years later, it’s Perry Chen from Kickstarter; I was talking to Fred and I
was like, what did I miss? Like he saw it before you did, how did I miss this?
[Inaudible 0:50:04] said you missed Perry and fortunately I still kept a
relationship with him, and I reached out and I said, “How did I miss you?” He

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said, “I couldn’t tell you that I was a waiter; I couldn’t tell you that I was an artist.
I had to come up with some incredible persona that someone would fund.” And so
that is the other part of it too, is that sometimes you miss the right ones and other
times you get – you know, other times you miss them for the reasons we both did
with these and we didn’t take the time to unpack it with them and figure out who
they were and unfortunately, just the volume of things we end up looking at in our
business, some of those do slip through the cracks.
Jerry: That’s a funny story, that’s a hysterical story. Thank you. Well, thank you both so
much for this. This was a really, really great conversation and I know people are
going to enjoy it. As I said to you before the call, I wanted you guys to meet for
such a long time and I finally made it happen by way of this podcast.
Chris: Yes, we did.
Jerry: Now you understand why?
Chris: Absolutely yeah.
Jerry: And so go off and go do good things together.
Chris: We will.
Jerry: All right.
Chris: Thanks for all of your support through all – it sounds like from this conversation,
we both benefited tremendously having you in our corner, so thanks for
everything Jerry.
Jerry: Well, it’s my pleasure. It’s just a delight to work with people that I really care
about and I care about both of you.
Bryce: Same.
Chris: Likewise. Thanks Jerry.
**
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
affected you. So, thank you again for listening, and I really look forward to future conversations
together.

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[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 0:53:17]
[End of transcript]