It’s so easy, sometimes fun, sometimes painful, and always tempting to compare ourselves to others. As entrepreneurs, the temptation is even stronger. It can at times seem like there’s an endless supply of compare yourself material - from the media, to social media. Ask any Reboot coach...one of the busiest days as a coach is the day a big acquisition or funding announcement occurs. The second busiest is the day after. So what would it be like to let go? What if you stopped trying to be a VC / entrepreneur / father like everyone else? What if you were just you and that was OK? That is exactly the advice our podcast guest offered up to a 34 year old Jerry Colonna - many, many years ago. We’re truly honored to have Brad Feld on the podcast with Jerry today. Brad is an investor, entrepreneur, and blogger who has been supporting entrepreneurs all over the world since 1987. Brad has also been a great Reboot supporter and teacher. In this conversation these two friends talk about VC’s as Dungeons and Dragons characters, Brad’s evolved investment criteria, and the single best piece of advice Brad offered to Jerry that changed his career.

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““I’m successful if I create a unicorn.” What a stupid, fucking phrase. What a stupid idea. That’s
success? Why? What does that mean?”
Welcome to the Reboot podcast.
“Can we live beyond compare?” — David Richo.
I’ve been journaling since I was 17; I’ve been using Evernote as a journal since around May of
2009. In leading up to this episode, I did a quick search of the phrase “compare myself.” 75
entries came up, I have no doubt that if I played with the phrasing a bit more, even more notes
would surface, but here’s a snippet from just one note: “And then when I saw the news in
company X, I felt like ugh again. I’m back in my place where I start to compare myself. I feel the
pressure to do more, I feel inferior, I feel behind, I feel – I don’t know if ‘inferior’ is actually the
right word, I feel like shit. I feel unworthy, it sucks.” It’s so easy, sometimes fun, sometimes
painful, and always tempting to compare ourselves to others. As entrepreneurs, the temptation is
even stronger. At times it seems like there’s an endless supply of compare yourself material,
from social media to media. Ask any Reboot coach, what are the busiest days they see as a
coach? It’s the day a big acquisition or a funding announcement occurs. The second busiest day
is the day after that. So, what would it be like to let go; what if we stopped trying to be a VC, an
entrepreneur, a father like everyone else? What if you were just you and that was okay? This is
exactly the advice our podcast guest offered out to a 34-year old Jerry Colonna, many, many
years ago. We are truly honored to have Brad Feld on our podcast with Jerry today. Brad is an
investor, entrepreneur and blogger, who has been supporting entrepreneurs all over the world
since 1987. Brad has also been a great Reboot supporter and teacher. In this conversation, these
two friends talk about VCs as ‘Dungeons and Dragons’ characters. Brad has evolved in evolving
investment criteria in the single best piece of advice Brad offered to Jerry that changed his
career.
**
Today’s episode, we are proud to say, is brought to you by JustWorks. JustWorks helps
businesses take care of their benefits, their healthcare, payroll and HR. It’s just that simple. We
use it and absolutely love it here at Reboot. And Reboot is more than just Jerry; it’s a full team of
very talented people and JustWorks makes it so easy to take care of that team. So, here’s another
member of the Reboot team.
Jeff: Hi, this is Jeff Riddle; I’m a coach at Reboot.
Dan: So Jeff, how did you become a Reboot coach?
Jeff: It started with pursuing a career in professional baseball and getting injured before I
actually got beyond college and then deciding, “Well, that sucks, I want to do something cool
like be a musician,” and then I toured professionally. That was fun and then I was like, “This is
cool but I want to do something else” and then became an entrepreneur, so it’s through this
process of high performance that I started to realize there’s these common trends, and that got
me really interested in coaching. Now here we are, a full circle, because a decade later, they say

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the best coaches are baseball catchers, which I happen to be, and now I’m doing it in the
executive level.
Dan: So Jeff, how does JustWorks make your job and life easier?
Jeff: Well, it’s basically invisible to me except for when I get an email, about once a month, from
Reboot, and all that email lets me know is that my bank account is bigger. But it’s great because
it makes the process of receiving payment from Reboot so streamlined and easy, and really out o
my awareness, so that I can worry and focus on things that are more important for my business.
JustWorks, as Jeff said, is a right kind of invisible. It just takes care of our payroll, compliance,
our benefits, even our 1099s with ease in top-notch support, so we can focus on things that are
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To learn more and to learn how we use it at Reboot, go to Reboot.io/JustWorks.
**
A quick note before we start today’s conversation with Brad Feld, we are planning a VC-only
boot camp for 2016; so, if this is something that you’d be interested in attending, we’re going to
have limited spots for it, send us an email at hello@Reboot.io and we will send you a note when
we have dates and we have opened applications.
**
Jerry Colonna: Hey Brad, how are you? It’s really, really great to see you my friend.
Brad Feld: Awesome to see you.
Jerry: Yeah. I’m excited because as a lot of folks know, I’m moving to Boulder, so I get
to hang out with my friends Brad and Amy a lot more and looking forward to that.
Brad: It has been in incredible joy to have you around, more the last couple of years and
I look forward to having you around even more and more.
Jerry: Well, I expect to be in the pool, in Sheffield, very shortly.
Brad: As often as you want; even if I’m not here, you know how to hop the fence.
Jerry: That’s it! Well, thank you too for coming on to this; you know, the podcast, we’re
just about a year now, and the podcasts have been really an extraordinary journey
for me, I think for Dan, our producer in this, for Reboot, but also for – there’s
been a little community that’s developed around this, and they followed it, and
just this week I recorded an episode with a guy that I did a podcast interview a
year ago, and contrasting where he was a year ago to here and so, you know, I
really – I’m deeply appreciative of this; you know, this opportunity for us to sort
of riff and gather our thoughts and share our thoughts about different topics. As
you know, I talked with Fred a couple of months ago, and just recently we talked
with Bijan, and so a lot of what we have talked about with them was sort of the

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experience of being an investor, and what’s that like, and I’ve been looking
forward to sort of checking with you, really around the same topic. So, just to
really get things going, one thought I had was to just talk a little bit about, what
does it really mean to be an effective investor? What does it mean to be an
effective board member and to give it even more context, I was talking with
somebody else the other day, someone that you know, I won't name their name,
and we were talking about the board of directors of the company that they are
with, and they had just left one of the companies that we are all investors in. And
he said, “Well, this board is made up of some really great people, but it’s not the
same board that Fred and Brad are on.” And there’s something almost ineffable
about a really well-functioning board, and when that relationship is just clicking,
and you just smiled, so, does that resonate?
Brad: Absolutely resonates; I have a line that I use over and over again about investors
in general, which is that investors are like ‘Dungeons and Dragons’ characters.
You know, we live in this environment, especially right now, you know, where
there’s huge amounts of writing and stuff published, and podcasts about VCs and
angel investors and what investors are like, and I run into this over and over and
over again where founders view – I’ll use ‘VC’ instead of ‘investors’ generally
but, view VCs as a singular archetype. They talk about this notion of ‘a VC’ and
there’s only one ‘a VC’, and that’s Fred.
Jerry: Referring to the name of his blog; right?
Brad: Of course; but this idea that VCs are the same is just wrong; and so you have to
start foundationally with that when you start talking about investors and boards. If
they are like Dungeons and Dragons characters, some are elves, some are wizards,
and some are orcs, and some are dwarfs, and some are trolls – actually a bunch of
trolls, and then you have to go to the next level, which is you have to start
thinking about a VC firm.
Jerry: Yeah.
Brad: A VC firm is not a collection of all wizards, or a collection of all dwarfs, it’s a
collection of different characters, so Foundry Group, you know, you get to choose
which one of us is which, but you know, I’m different than my partner Jason, than
my partner Seth and my partner, Ryan. We have very shared, common, belief
systems, we call them our deeply held beliefs, we have a long relationship with
each other, but we are different. So, the first step is for the founder to think about
the VC as an individual, rather than a collective and a singular archetype, and I
would say the same thing with investors and then I keep going and say the same
thing with board members. It’s not that you are ending up with a thing that
behaves in a consistent fashion, you are engaging with people who are
fundamentally different, have different experiences, have different strengths and
weaknesses, have different skill levels, have different tools and over time,
hopefully, they grow and they evolve and they change. Sometimes they grow

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based on experiences, sometimes they grow based on their knowledge, sometimes
they grow based on changing chemistry, because you know, we are just big bags
of chemicals after all, and most importantly, the interaction and the interaction
effects evolve. And so, when I think about what makes an effective investor, it’s a
very difficult question to answer in the abstract because there’s so many different
characteristics of each individual person that can make them effective or
ineffective, for whatever situation they are in, and really it comes back to the
responsibility of the founder for understanding that her investors are going to be
different as individuals, and that she needs to put real energy into understanding
what drives them probably before they invest in her company. An effective
investor is going to be one who has intellectual and emotional alignment with the
founders, might have a different set of viewpoints on certain things, but is coming
into a situation with a frame of reference that’s, I don’t think ‘congruent’ maybe
is not the right word, but at least it links back to those founders. The ineffective
investor is one who comes in with a completely different frame of reference, and
I’ve experienced that both as an entrepreneur, founder and as an investor, where
you can be a month into a new investor and you realize that that new investor and
the founder – or that new investor and CEO are so off kilter because their
expectations about what they are going to get out of the respective relationship
and how they are going to engage with each other is totally missing. And you
might say, “How did that happen? Don’t you have like an opportunity to learn
each other?” And the answer is yeah, but the investors and many investors are
quite good at selling themselves; you know, firms are good at promoting
themselves, some founders don’t have a lot of options in terms of different
choices for investors. A lot of founders are so busy just scrambling to get a
funding raise that they don’t really think how important it is to dig in deeper in
advance. There’s lots of founders who don’t value the importance of that
relationship until after they are in the relationship and realize they are totally
fucked because it’s going to be a bad relationship that they are going to have to
navigate through. So, there’s a whole spectrum of it, but if you circle all the way
back around, that’s why it’s so hard to say what makes a good investor, at least
for me, because it’s not a global response.
Jerry: I love this, and I love the identifying that the way in which the answer really
depends on the circumstance that we are talking about, and there’s an attribute, I
think, to your analogy that I would extend it which is that founders are Dungeons
And Dragons characters as well. Founders are also an orc, or a dwarf, or an elf, or
a wizard or whatever, and if that’s true – and you just nodded so I’m imagining –
Brad: Yup.
Jerry: – that that’s true, I would say – one of the many things I was writing down as you
were talking was that the question really isn’t what makes an effective investor,
the question should be what makes your board effective or not, your circumstance
effective or not. To borrow or phrase from a therapist over the years, she was

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often fond of saying, “There’s a right way and there’s a wrong way, and then
there’s the way that works.”
Brad: You’re right.
Jerry: And the way that works, requires a kind of awareness of the underlying characters
that you are playing with; their experiences, their anxieties, their issues, that sort
of thing, plus your own stuff and that goes back to my other phrase, the whole
notion of radical self-enquiry, being able to answer honestly, “Am I a troll?” “Am
I an orc?” Does this resonate?
Brad: Absolutely. There’s a profound piece of it for me that I have learnt over a long
period of time, and it goes from when I first started investing as an angel investor,
which was in 1994 and I first started investing as a VC investor, which was in
1996, and the distinction for me between the two is, as an angel investor I was
writing checks out of my bank account, and as a VC investor, I was writing out
checks out of a fund, which included some money from my bank account, but was
also a broader fund. When I made my first 40 angel investments which happened
in 1994 to 1996, I only had two decision criteria associated with whether I was
going to invest in a company or not. I was only investing, at that time, into
internet and software related companies. The only two things were, number one,
did I care about the product? Was the product interesting to me? And number two,
was the founder focused on their product? And I didn’t really have the right words
for it then, and I probably talked about as pretty fuzzy, “Did I like the founder”
was probably what I talked about back then. So, you know, did I care about the
product and did I like the founder, or like the founders? I went through this
period, you know, as an investor, with the first fund I was part of, which was
Softbank Venture Capital, which was turned into Mobius, and that went through
this broad arc of a small start in 1996. I fund-raised in 1997 with four partners and
two assistants, and then by 2000, we’d raised these three funds, a couple of billion
dollars of capital, and had like 60 or 70 people, and then in 2001 the whole world
blew up. And in that cycle, we went from – or I went from this very, very simple
way of looking at things, which was, I am a frame of reference of stuff that I
know really well and then I have these two things that I am choosing. Through
this art – I mean, at one point I remember we had some point system, I'm not
going to remember the point system, but you know, we had some point system
where you – kinda, everybody on a piece of paper, would rate the six attributes:
management, vision and market and you know, we should have a line for bull shit
factor –
Jerry: Or, our own bullshit factor.
Brad: That is probably what I’m getting at, and you added up these points and if it got
above 70 points, I remember that, like 70 points was a threshold that you kept
going and if you did – okay, whatever. And when I wind the clock forward to
2015, 20 years later, the way I describe how my partners and I at Foundry Group

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decide whether something is for us as investors is, first we have a set of negative
filters and they are very simple ones; is it in the US, yes or no? Have you raised
less than three million dollars, yes or no? Is it in one of our themes, which we
define very intellectually for us? And if you get through that filter, you know,
early stage, we don’t have to be your first investor, we only invest in the US and
we only invest in our themes, if you don’t get through that, we pass immediately.
We have a line, “We’d like to say no in 60 seconds.” We don’t want to waste the
founder’s time and we don’t want to spend our time on things that we are not
going to likely invest in. You get through the filter, and this is the magic, and now
the questions are, “Do we have an affinity for the product?” “Are the founders
obsessed about the product?” Not passionate, I think passion belongs in the
bedroom. I like passion, but it’s a different thing and it’s not unhealthy obsession,
it’s obsession, it’s “I’m on this planet to do this thing now.” And then the third is,
“Do they want to be partners with us long term as much as we want to be partners
with them?” So, you take that arc that I’ve gone through, and you link it back to
what you said earlier, for me, and for my partners Jason, Seth and I, our
evaluation process of whether or not we want to work with somebody is very
much like that instinctive process I had in 1994. Invest in an area you know well,
about things that you care about, about people that you want to work with, end of
discussion. One of the things that comes out of that for us as a firm as we learnt
over time is, our job as a firm, as a venture capital firm, is not to invest in every
great company. Our job is to invest in ten companies a year that we think could be
great, and you never make an investment as an investor in a company that you
don’t think is going to be amazing. “Hey, I just invested in this company. It’s a
total piece of shit, but I invested anyway because I felt like it.” That never
happens, and we know that a bunch of things that we are going to do are not going
to be successful. If you turn that around for the founder, I just articulated my and
Jason, Seth and Ryan’s view of the world; I think every investor, individual
investor and every venture investor has a view of the world, whether they realize
it or not. Also, every founder has a view of the world, whether they realize it or
not at the stage they are at. You are helping the founders in a truly powerful way,
and the notion of radical self enquiry and the phrase of radical self enquiry I use
all the time, and when I run into a founder who needs a dose of that, you know, I
tell him to listen to the podcasts as a starting point. And they say, “Okay, that’s
podcast, and I don’t have time to for it” I don’t have time for it and I’ve to listen
to them all. But you have to get your shit together and like the advice I’ve given
you is, go start; like, think about it, think inwards. Within Techstars we do this all
the time; a big part of it is learn yourself first, but then also realize that most of
the people that you are going to interact with on this planet, especially in the
context of entrepreneurship, actually don’t really know themselves.
Jerry: Right.
Brad: And if you start from that perspective and you know that, and part of your
involvement and engagement, whether you are an investor or a founder, is first
know yourself, and then don’t feel responsible for teaching other people

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themselves, but allow yourself to be exposed to them when you are going engage
in a relationship, whether it’s a co-founder, whether it’s an investor, whether it’s
an employee, whether it’s a partner. Allow them to engage with you and while
that’s happening, look for who they are. And if they don’t expose who they are to
you when you are willing to expose who you are to them, be a little more careful.
And if they are willing to expose who they are to you, go to the next level in
terms of depth. That’s why I said it’s so profound; once the founder realizes that
just like the investor is not a singular archetype, there is no right way to be a
founder. There is no one answer. We have lots of heroes, but you know, are you
trying to emulate – pick a hero, Steve Jobs, Bill Gates, Marissa Mayer, Mark
Zuckerberg, Jerry Colonna –
Jerry: Right.
Brad: – you try to emulate them, or you try to learn from them, pieces that inform how
you are, and what you want to be. And for me, the most satisfying experience as
an investor, as a board member, as a partner to a founder, as a partner to other
people in the VC world is to have that kind of engagement, which is not all lovey-
touchy, I mean, you know, there’s plenty of arguments and there’s lots of hard
problems that you have to solve, and there’s lots of stress, but you come at it from
a perspective, knowing yourself first. And then the last thing I say on this is
realizing that if you start down the path of learning yourself, that never ends and
of course we have helped each other through the years, and I have learnt a lot
from you about that, it never ends until they put you in the ground.
Jerry: Yeah.
Brad: And that’s part of the joy of being human; it’s also a part of the pain in the ass of
being human.
Jerry: Yeah, I think it was beautifully said, really, really well said, and you know, a
couple of things I’m taking from that, one is that as a partnership, you guys are
not necessarily only investing in elves. What you are looking for is, who is this
person and perhaps do they even know themselves. And then the second is this
notion of – and we’ve both been riffing on this, is this notion of knowing yourself
as a core attribute of the radical self enquiry, the “Am I an elf? Am I an orc?” And
I would even argue, when I encounter the elf that is Brad, or the wizard that is
Brad, and let’s name it, the troll that is Fred, just kidding –
Brad: Or the troll that is Brad, ‘cause I definitely – I got troll on me a bad day.
Jerry: Right, and do I then become a troll? Because that’s the other thing is, how do I
react to this person? Even if I define myself, that definition is not static because
I’m human and part of my humanity is an experience of change. So, I’m actually
going to alter the question even further and say, in positive theory that what we
are really talking about isn’t effectiveness as much as we are linking authenticity

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to effectiveness, and that there is something po0werful to this notion of
authenticity in the board room, in that partnership. You know, a bunch of people
who kinda know each other, and know themselves, and aren’t afraid to show their
troll side, their wizard side, their elf side, their orc side, and can laugh about the
fact that – right now the troll side just showed up; and create space in that room
and around that table for people to sort of engage with each other.
Brad: Yeah, I think that’s – I think a fun way to think about it, you also have – I think
this notion of many levels of ability to expose oneself, to others in these
environments. So, it’s not that everybody is – you know, let’s use a one to ten
scale, and let’s define authenticity on a one to ten scale, which doesn’t work
really, but let’s just pretend for a sec that it does work, that it’s a single line; you
know, one person is a ten, the other person is a seven, another person is five, they
are just different place – one person is a level three of authenticity, and the other
person is a level 27, and the other person is a level 15 in terms of their own
ability. Recognizing that it’s not just a single dimension; “Did you eat breakfast?”
“How are your bio-rhythms?” “Do you have a headache?” “Did you stay up late
last night doing email?” “Are you under pressure because of ________ at work?”
“Are you under pressure because of ________ at home?” You know, “Is your kid
sick?” “Did you have a fight with your significant other?” “Are you cold because
you like warm rooms and the air conditioner is on?” “Are you warm because you
like cold rooms?” “Did you have two milkshakes at lunch instead of one, and now
you are in a semi-diabetic coma?” You know, “What’s going on?” is an important
part of it and I think that it’s very easy to lose sight of that as – especially in the
board room, as you are the CEO trying to manage the interactions, it’s also easy
to lose sight of that when you hear something that someone says that you know is
maybe directionally correct, but it’s going to really impact negatively somebody
else, on your team that happens to be sitting in the room. Or, when you have your
own – you know, you have an extra milkshake or you are too tired or whatever
and you are having a reaction to something that you know is truth but you are not
ready to hear the truth, or you don’t trust that it’s been said and coming from a
place of support and help, but it’s coming from a place of criticism, and then you
layer on top of this – everybody has different experiences if you are a CEO or a
founder, you are in a board room, everybody knows Mr. Socrates, the board
member. Mr. Socrates can't help herself – Mrs. Socrates; I have in my mind – I’m
going to try it for a month, maybe I’ll do it in September on my blog, instead of
using ‘he’ as the pronoun, always use ‘her’ and ‘she’. So, always use female
gender for pronouns instead of male gender, and it’s interesting how hard it is do
it. I thought coming into this that I was going to try to do it, and I already blew it;
so I’m going to give up ‘cause I blew it, but if you read my blog, maybe
September will be the female gender pronoun, as I try to rewire my brain not to
default so much into a male gender pronoun. But imagine a situation where Mr.
Socrates is one of your board members and at every board meeting, Mr. Socrates
asks 10-20 questions and never tells you the fucking answer, and never makes an
assertion about what he thinks would be a good idea. The questions are good
questions. You know, 20 questions, 10 of them are easily answerable, five of

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them are irrelevant, but five of them are really good questions. As a CEO, how do
you feel? By the fifth board meeting, you want to crack this guy’s head open. You
know, you’re being attacked constantly because this person is asking you
questions, maybe not realizing that that’s the way the person is trying to get you
to an answer, or maybe he is an asshole and he is just asking you questions and
that’s the way he operates. So, getting the next layer down is where the magic
starts to happen. If you form your impression based on just the interactions, and
you never say to Mr. Socrates one-on-one, “Mr. Socrates, here’s what’s going on
in my mind; I’m struggling in our board meeting ‘cause all you do is ask me
questions. It makes me feel insecure. Ten of your questions I can answer, five of
your questions I don’t think are relevant, but five of your questions are awesome.
Do you think I’m stupid? Is that why you are asking me questions or are you
trying to help guide me to an answer? Help me understand why you are just
asking me these questions ‘cause I’d love to know the answers to the ones that are
the really hard questions if you know them, or is just a style?” You don’t want to
be that direct, but figuring out in every situation of every relationship, building
that; when someone is on a board with Fred and I, and we’ve been on a handful of
board together over the years, we are different. We approach things different, we
think about things different. I would say, as investors who have grown up
together, I think we have a lot of shared common values, I think we have a lot of
belief systems that are similar. If you actually look at what we have invested in
over the years, you know, the overlap of the things we have invested in is fairly
small, much of what we have invested in different areas, although some of it
overlaps, so we’ve learnt a lot of different things. But we approach problems in
different ways, our styles are different; that’s incredibly powerful for a CEO who
understands it and is probably maddening for a CEO who wanted to be packaged
and easy. And we’re both very easy to learn because we are so accessible; I would
suggest that Fred is just as easy to learn as I am easy to learn, whether it’s just you
reading his blog or just interacting with him as a human. Now, take an investor
who is not easy to learn; an investor who doesn’t blog, all of the tweets that they
do are just retweets of press releases of things from their portfolio of companies,
as someone who has had success but is out of the limelight, or is someone who
hasn’t had much success yet, but is clearly a very smart person, or whatever it is.
As a founder, you are going to have this collection of different types of people
you have to learn, and you can be passive about it and let them impose themselves
without learning them or, you can try to figure out how to try to learn them in a
way that gets them as a board, working more effectively together. That’s the next
layer down; it’s not just being authentic, it’s not just sending a tone where
everybody is open and honest because people are going to have a range of it, and
that’s not the only dimension that matters, but it’s a good proxy for how to move
into it.
Jerry: So, take this and go back in time, time machine here, you and I first met ’96?
Brad: Yup.

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Jerry: And when we both had much darker hair than we have today, and –
Brad: I still got some length to it.
Jerry: Yours has length, mine has sparseness. You know, and thinking this over, you
know, if I were to give myself advice at that age, the first thing I would say is to
relax because that was always hard for me that it will unfold, but to this point
about authenticity and self knowledge and self awareness and radical self enquiry,
I would be encouraging myself to really accept things, and in fact, what just
popped in my mind was actually a piece of advice you gave me, back in those
days. And you probably won't recall this, but I was struggling and it was like the
first year that I was working with Fred, so it was ’96; so I started as a VC in’95,
and I was really in a tough place because I was feeling this deep and profound
imposter syndrome. I was feeling the sense that I didn’t go to an Ivy League
school, I was really in a realm that I didn’t understand, and you said something
very powerful to me. You said, “Jerry, stop trying to be a VC like everybody else.
Just be a VC like you.” And you know, I mean, this isn’t a correlated fact, these
are coincident facts, but the next year, I was named to FORBES ASAP list of 50
best VCs in the country. And that piece of advice, from my friend Brad was really
powerful for me and in a sense, it’s a less explicated reference to what you have
just been saying.
Brad: Yup. I think that the – I don’t remember saying that specific statement to you, but
I have said some version of that many times over the years, including to myself,
but to lots of other people you know, founders, investors, and the essence of it is
always, the thing that is so powerful is that as an entrepreneur, you get to define
your reality. It’s not unconstrained; you have endless constraints, you have
financial constraints, you have time constraints, you have resources constraints,
you have people constraints, you have intellectual constraints –
Jerry: You have physics.
Brad: Yeah, physics [Crosstalk] but you get to define your own reality and I think that’s
true for all humans, not just entrepreneurs. For many humans, you are in a
different place – you start from a different place, the Warren Buffet, you won the
[Unclear 0:36:38] lottery line, is an important one. I was born a white American –
a white, Jewish American in Blytheville, Arkansas in 1965 to two loving parents
who are still together today, as an oldest son; yeah, I got a lot of genetic whims on
that in terms of my starting point. So, if you view it as a zero sum race, against
seven billion people on the planet, I got a really gigantic head start. But it’s not a
seven billion person race. It’s just not. It’s from where you are as a starting point
to where you go. And you know, I was 31 when I said that to you, you were 33 or
34 because you are a couple of years older than me, and you know, in our thirties,
we have both been successful in our different ways. In our thirties, as a successful
person, all this – in a mode that’s a very powerful potential mode, the notion of
imposter syndrome, the notion of ‘I have to be like that other person’ is very

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powerful and now take it to the founders of the world; ‘I’m a founder, I’m 25
years old, I’m 31 years old, I’m 42 years old, I’m 55 years old, and to be
successful, I have to look like that.’ Bull shit. This is total bull shit. You are
probably already successful if you are a founder because you are pursuing
something that you want to pursue. Start with that and now pursue it in a way you
want to pursue it. Be yourself and recognize that you don’t have to be number
one; that’s not the goal. The goal is to pick a whole bunch of other attributes that
you want to have satisfaction on and as you have more and more success, you
actually can open the aperture of what those goals are, and I've had people say to
me, “But that makes it harder, I have more choices.” And my response is, “Isn’t
that good? Don’t you want more choices?” “I’d rather not have as many choices.”
“Why?”
Jerry: Well, it’s frightening for people because they actually have to define what success
is for themselves.
Brad: Of course, and you know, that’s part of the journey that you go on. My wife, Amy
and I have a foundation and one of the programs we do from our foundation is
something at Wellesley College, where she went to school, which is called the
Anchor Point of Fellows and Global Leadership. So, every year, we have a
program for undergraduates and Wellesley young women who are in their 18-21,
apply for and go on a three-month internship that we fund, somewhere in the
world that has something to do with global leadership, and they have to define
what they are doing. So it’s about leadership including leadership starting from
your own frame of reference and we have a bi-annual conference; we just had our
conference a couple of weeks ago, and Amy says to me as where driving home at
the end of the first day, which was so powerful and so awesome, about 20 women
had gone through this so far, we are now doing about seven a year, she said, “I
just want to tell them all, it’s going to be okay.” They are all in the late teens to
mid-twenties now and they are magnificent. They are incredibly, you know,
interesting, smart, powerful, confident, forward-thinking young women, and we
just went – as people in their late forties say, “It’s gonna to be okay” which is
kind of the same thing, just be you.
Jerry: Yeah. You know, in a sense what I’ve heard you do in a beautiful way, is kinda
broaden and open up the definition of success, and I’m thinking back to the folks
that I know, my children, clients, the folks that I know in their twenties, who are
so locked and not only to what the models are supposed to be of who I’m
supposed to be, but also what is success. And that if you can expand the notion of
what is success, all of a sudden, you can take in that success might be defined as
being satisfied, success might be defined as generally being happy even though
some days I’m sad, success may be defined as we often say at Reboot, quoting
David Whyte, “Good work, done well for the right reasons.” That success is not
everybody coming out the same way. Does that make sense?

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Brad: I’ll give you a couple of more examples. Success is not only the broad arch, it can
be the small things; so, success for me, often on a Saturday morning, is that I slept
for over 12 hours the night before. I love to sleep. I’ve always been a great
sleeper, you know, one of my super powers is I sit down on an airplane, I put my
seatbelt on, I close my eyes and I’m asleep until the wheels hit the ground. As
long as the plane flight is less than five hours, no problem and sometimes if it’s
more than five hours, I can do that without an ambient. You know, it’s a nice
superpower to have because it’s basically time travel. So, you were saying about
success, and it doesn’t have to be externally driven, other people validated,
measures of things that line up against our suicidal check marks. It can be that it’s
11:30 on Saturday, and I just rolled over and I thought to myself, “That felt so
good.” And I know that Amy is off doing her thing ‘cause she likes to get up
earlier in the morning, and when I come out, she’s going to say in her sing-song
voice, “Brad Feld” which is her morning greeting. And she’s not going to be
angry that I slept till 1130, she’s going to know that that was a successful Friday
night sleep for me after a long week of working hard. So, one of the things that is
so vexing, and it’s vexing to me and it’s vexing to most humans is the idea of
success and defining it like the notions that you talk about at Reboot, are
continually changing. Success for me at 24 is different than success for me at 30,
is different for success for me at almost 50, and a successful day is different in
addition to a successful week, or a successful month, or a successful year. The
idea of what success is in the business context with a company, success in a
relationship, success on a board, success for an athletic endeavor, it changes. I
was with a friend yesterday, who just decided – she’s a great cyclist, and she just
did something called ‘The peak to peak’ and she just did it and did extremely
well. She was going to do this incredibly hard bike race, and she just decided not
to do it. She was trained for it, she was ready to go and I said, “Why?” She said,
“I just didn’t feel like it.” And I said, “Because you had nothing to prove?” She
says, “Yeah, I had nothing to prove, and I just didn’t feel like it.” I said, “How do
you feel?” She said, “I feel great that I decided not to do it.” That’s success. She
has nothing to prove, she doesn’t have to go do this incredibly hard bike race to
check off another bike race on the list of incredibly hard bike races that she’s
already chucked off her [Unclear 0:44:51] and if she’d felt like doing it, awesome.
So, it’s getting into that soft headspace about what success actually means, and
letting it be context specific, and if you are founder and you can do that with the
ups and downs, and the roller-coasters, and the highs and the lows and the stresses
and the challenges and the disappointments and the frustrations, you’re going to
have so much of an easier time than if you hold on to this absolute notion of what
success is.
Jerry: So, we had this beautiful conversation, I think, around this notion of authenticity,
where we morphed the notion of effectiveness into a notion of authentic
relationship even in the boardroom, and I could hear in the back of my mind, the
anxious clients that I have, and even the people listening to this podcast saying
things like, “Yeah, that’s all well and good, but I got up ________”.

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Brad: Yeah.
Jerry: And what we’ve done I think, by expanding and altering the notion of success, is
answer that other anxious question which was, if success is only defined as
“becoming a unicorn” to use the common phrase right now, then this notion of
authenticity in the boardroom becomes really challenging. But if success is
defined by a broader set of metrics, no matter how hard that definition process can
be, then all of a sudden, we have this space for, ‘oh success is defined by having a
fucking good time, trying to do something impossible like launch a business.’
Brad: Yeah. And you can take it on that spectrum, even narrower; you have a major
source of anxiety and a thing that’s in front of you that you know you have to
confront. It’s the big, ugly demon in the cave, and you know it’s time to go stick
your head in that demon’s mouth, but you have been resisting, avoiding, and you
wake up in the morning and you say, “Success today is going to be sticking my
head into that demon’s mouth. That’s success and that’s the only thing I got to do
today to have a successful day. All the other stuff today, yeah, I’m going to do
some other stuff today, but success is if I go do that thing.” And you can
repurpose the notion of success and you know, that example is not – it’s not fun,
it’s not satisfying, it’s not going to be enjoyable, it’s not going to give you a thrill,
it’s not going to make you any money, it’s not gone get you – might get you on
the cover of a blog, I don’t know, but you are going to stick your head in that
fucking demon’s mouth, and you are going to deal with that thing, and after you
do that, you are going to have success. And when you can scale the notion of
success up and down, and you can start to focus on you and what you need to
nourish you in the moment, which by the way, you might not have any demons in
the cave right now, and that gives you range of motion to go define success as
something different which might be, today I’m going to walk out of the cave and
just go wander around in the sunlight, whatever the metaphor of that is. And that
doesn’t mean that you shouldn’t define long arches of success and you shouldn’t
have a goal of what success means for your company, but the ultimate definition
of success versus those intermediate definitions get people hung up. “I’m
successful if I create a unicorn.” What a stupid, fucking phrase. What a stupid
idea. That’s success? Why? What does that mean? I mean, do you get on a list and
it’s a list that five years from now is going to be a different list, and then there’s
going to be lots of people who are analyzing who is on the list and now who is not
on the list, why bother with that? What’s the point of that?
Jerry: That’s beautiful, and we’ll start to wrap with this, but the – I’ve always loved
your ‘What fucked up things is going to happen today’ mantra, which I'm sure
we’ll find the blog post in which you first started talking about that and link to it,
but then there’s a corollary now which I’m hearing, which is, ‘What successful
thing am I going to do today?’
Brad: Yeah, I think the balance between those is part of what can help someone be seen
in the context of the general – it’s like general in special relativity. The general

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and special and Saturday, of being a founder is to know that everyday something
new is going to be fucked up in your world and that’s okay.
Jerry: Yeah.
Brad: And that something new is going to be surprisingly awesome in your world, and
that’s okay. Your day isn’t dependant on finding the fucked up thing and solving
it, and your day isn’t dependant on experiencing the awesome thing because being
a founder and creating a company and living a life is a continuous experience of
lots of different things that happen in unpredictable, random and chaotic ways and
if you try to control that, it will be very, very, very hard and very unsatisfying. It
doesn’t mean that you can't control things, but if you let that broad arch unfold
and you participate in the unfolding of the good and the bad, that’s life.
Jerry: That’s beautiful and you know, I will slip in one more thing here which is that
you may not know it my friend, but you are a Buddhist.
Brad: I stand on your shoulders and I follow in your footsteps.
Jerry: Thank you so much for this, this is an amazing conversation and you know, it just
makes me miss you all the more.
Brad: I will see you soon, and we will spend plenty of time paddling around in the pool.
Jerry: You got it.
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.
[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 0:52:44]
[End of transcript]