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Welcome to the Reboot podcast. Weā€™re proud to say that todayā€™s episode is brought to you by
Justworks. Justworks helps businesses take care of their benefits, healthcare, payroll and HR. Itā€™s
super-simple and powerful. We use it and we love it. And this podcast really is way more than
just Jerry; so we wanted to take this opportunity to introduce you to more of our team, and hear
their experience in using Justworks.
Ali Schultz: Iā€™m Ali Schultz, and I am the COO of Reboot. Justworks makes my life insanely
easy. Itā€™s every HR solution I have ever wanted in one place including my benefits, and I donā€™t
have to think about HR things at all.
Dan Putt: And how does your experience with Justworks compare to other providers that
you may have used in the past?
Ali Schultz: I have tried two of the largest HR solutions in the market, and the time that it has
taken out of my life to use both of those programs is maddening to me. Back then, at least a
couple of years ago, I remember thinking to myself, ā€˜This really doesnā€™t need to be as
complicated as it is and I was hoping that someone would create what Justworks has created. I
feel like it has kind of given life and a new-found sense of joy and freedom to HR professionals
around the globe.
Dan Putt: Well, you hear how much Ali loves Justworks and a happy Ali is a happy Reboot.
If you are ready to grow your business and not your busy work, head over to
Reboot.io/justworks. Youā€™ll find out more about how we use Justworks and how it could work
for you. Thatā€™s Reboot.io/justworks.
ā€œEveryone thinks of changing the world, but no one thinks of changing himself.ā€ ā€“ Leo Tolstoy.
It sounds so obvious, perhaps even tongue-in-cheek, but it also seems to be forgotten enough that
it needs to be said aloud again. Investors are human too. They, like the entrepreneurs they back,
can ride the rollercoaster of emotions that often come with starting a company; anxieties, fears,
excitement, the temptation to merge sense of self with success or failure. What challenges and
problems can these emotions create? What tensions can arise between entrepreneurs and
investors? Whatā€™s the opportunity for entrepreneurs and investors in recognizing and addressing
them? Weā€™re very excited to have only our second investor on the podcast, the wonderful Bijan
Sabet. Bijan is a partner at Spark Capital, a Boston-based VC firm that has backed 108
companies including ones we all use and love, such as Twitter, Trello and Tumblr.
In this discussion, Bijan and Jerry explore some of the tensions that often arise between investors
and entrepreneurs, the emotional perspective of the investor, and the importance of purpose in
artistry. As a bonus, it includes Jerry reading a blessing at the end, so stick around for that; for
full links, notes, quotes and more, head on over to reboot.io/podcast. Now, enjoy their
conversation.
Jerry Colonna: Hey Bijan, itā€™s good to see you again; itā€™s been a long time.
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Bijan Sabet: Great to see you; hi Jerry.
Jerry: Yeah, and thank you for coming on the podcast. Now as I was saying before we
started recording, you are actually only the second investor Iā€™ve had on. So, itā€™s
actually kind of fun and as a former investor and someone ā€“ weā€™ve been friends
for a while, Iā€™ve been interested in really exploring more of that relationship
between investors and entrepreneurs, and I really appreciate your coming on to
spend some time talking about that, and to really talk about, perhaps some of the
areas where youā€™ve seen some problems, and some of the areas where youā€™ve
seen where it works well. But before I jump in on that, I just wonder what your
reaction would be to this notion that the tension that can exist between investors
and entrepreneurs is really a problem; am I seeing that correctly?
Bijan: Yeah, I mean, it certainly exists for sure. You know, itā€™s funny, this week, this
very week is our tenth year anniversary as a venture capital firm at Spark.
Jerry: Oh congratulations.
Bijan: Tomorrow, actually the 15th is our ten year. So itā€™s a moment for me to kinda
reflect on the whole bunch of experiences and all that and yeah, the tension can be
real and sometimes itā€™s even there before this relationship starts. Thereā€™s this
thing in the blogosphere, or on other things where itā€™s like, hey, you know, be
weary of the VC or you just kinda have this dynamic that is sometimes set up in a
funky way.
Jerry: So, even before the relationship starts to unfold, and what Iā€™m hearing you say is
that thereā€™s an almost fear that steps into that; am I naming that correctly?
Bijan: I think so. I mean you have ā€“ and obviously thereā€™s fear on both sides but you
know, there are some examples where these relationships start with an open mind
and a positive you know, disposition I guess, or frame of mind. But thereā€™s
somewhere you can kinda feel this guarded world where itā€™s like, ā€˜Hey Iā€™m
raising capital, Iā€™m gonna wrap this up in the next ten days and you know, weā€™re
having our meeting this week and weā€™re accepting term sheets next weekā€™ and
you just feel this wall where you know, little bit of fear, concern, you know, all
the stuff and it just creates a very tough dynamic to break through. At least from
my standpoint, it creates ā€“ itā€™s very hard to engage that way. As you know, these
are very long-term relationships, and if it starts that way, howā€™s it gonna last?
Jerry: Yeah. What do you think the root of that is? Where does that come from?
Bijan: You know, I think that in all of these things, thereā€™s some curls of truth to this
stuff; I mean, thereā€™s plenty of examples of relationships, business relationships,
investment experiences that didnā€™t go well and so people try to learn from those
lessons and pass them on, but I think as they get cherry-picked these lessons, and
as they get kinda reassembled, some of the context is lost. So, you know, the
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lesson can be like, ā€˜Hey you got to focus on your business, donā€™t waste time with
investorsā€™, you know, thereā€™s some merit to that and to be thoughtful about it, and
to be mindful of your time but then taken to its extreme, you can get a version of
that thatā€™s not awesome. I think probably a lot of this is based on ā€“ thereā€™s like a
lot of good lessons then it just gets kinda messed up along the way.
Jerry: And what if you learned ā€“ I mean I guess ten years ā€“ and Spark is your first
Venture Capital firm; is that right?
Bijan: Yes, I really enjoyed your chat with Fred where you know, you had all these
different experiences over different history; yeah but for me, this is it. This is all
Iā€™ve known.
Jerry: So looking back over those last ten years, you know, we didnā€™t plan for this to be
a moment of reflection but great, fantastic. So looking back at those last ten years,
what are some things that you might have done to contribute to some of that fear
in that relationship?
Bijan: Yeah, well look, I mean the beginning ā€“ actually Fred told me this early on; I met
Fred Wilson before there was Spark Capital. We had a mutual friend, Steve Cain,
who introduced Fred when he ā€“
Jerry: Sure, and letā€™s be fair, I introduced Steve to Fred.
Bijan: Thatā€™s right, thereā€™s a real connection here and Fred I met, he was in Boston
raising money for his first USV fund and before that fund organized, I met him
and we stayed in touch but after I became a venture capitalist and we had our fund
up and running, I remember he said something to me in passing about like, you
know, one of the worst things is a VC who had operating experience, who has no
board seats and no venture experience. Like that was a lethal comment or some
version that ā€“ Iā€™m probably getting the exact quote wrong, but basically he was
talking about me. Maybe intentionally or unintentionally, but you know, an
investor with no other board responsibilities, loads of time at his or her disposal,
but yet has a track record and an operating experience, that creates a scenario that
can be very tough for investors, new investors were you suddenly want to add
value, care about these investments, you care about your firm, you care about all
these different voices that are coming at you. And you know, Iā€™m sure I know Iā€™ve
learnt a lot in the last ten years, but in the beginning Iā€™m sure I was just like, you
know, much more kinda hasty about things than I hopefully am today.
Jerry: So was there something about having been an operator that made you more hasty?
Bijan: I think the natural thing, at least my own experience, and that Iā€™ve seen is that you
ā€“ itā€™s a very you know, different job, and so when you no longer have an
operating role in these companies but you kinda feel this closeness to the
company, that you know, itā€™s like, ā€˜Hey thereā€™s thing not working out here. I
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know how to fix that thingā€™ and that can be a really tough situation because then
youā€™ve gone from, you know, a partner to an unwanted guest in the house.
Jerry: Yeah, you know, Iā€™m recalling a similar experience I had when I first became a
VC, it was probably my first year with Fred at Flatiron, and I had made ā€“ one of
our first investments was an investment I made in a company called Mainspring.
The co-investors there, the lead co-investors were Bill Kaiser from Greylock and
Paul Maeder from Highland, two pros, gentlemen, thoughtful people who taught
me so much about being a good investor. And I remember I came out of an
operating background, I had an editorial background, and our first business model
at Mainspring was basically an information service in the IT space, and I made
the mistake of ā€“ a really rookie mistake of saying, Iā€™m gonna help ā€“ and Iā€™m using
that term loosely ā€“ by jumping in and Iā€™ll go up there one day a week and Iā€™ll be
the, sort of, quasi-editorial person there. And itā€™s so great you know, doing this
and John Connelly, who is an incredibly effective and thoughtful CEO, someone I
have learned a lot from as well welcomed that. He welcomed the additional
thoughts; I mean, I didnā€™t feel like an unwelcome guest, but maybe I wasnā€™t
always as conscious of the feeling. But I remember Bill Kaiser pulling me aside at
the end of a board meeting one time and he said to me, ā€œWhat the hell are you
doing? Like you actually have to choose; are you gonna be an operator or are you
gonna be an investor? You could be a really good operator, but as long as you
hold that chair, as long as you take that role, youā€™re actually preventing the
company from filling that role.ā€ And it was a shock and I was really grateful for
that lesson because I could see, if I had let my ego go forward, ā€˜cause really what
ā€“ for me what I was going through was, this venture business, this is scary and I
donā€™t really know what Iā€™m doing, shhh, donā€™t tell anybody.
Bijan: Yeah.
Jerry: But this other thing, this operating role, that I know stone-cold.
Bijan: Right.
Jerry: So rather than actually thinking about whatā€™s in the best interest of the company, I
was trying to manage and massage my own fears by getting all involved, and
thinking well about myself by telling myself that I was helping.
Bijan: Yeah.
Jerry: Does this resonate at all?
Bijan: Oh yeah, itā€™s such a great point; I mean, if I were to contrast Fredā€™s comment
about the worst thing as an idol ā€“ former operating - now turned investor, my
worst nightmare is a VC on the board with me that has a situation where the rest
of their portfolio is on fire and this is the shiny company because then you are
really in a pickle where you can feel that like unnatural angst and pressure being
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put on to this company for reasons that have nothing to do with the company. But
you see it and VCs are humans and they get stressed and nervous like anybody
else and when the rest of the portfolio is on fire and you have this one great
company, and all of a sudden they have this unnatural expectations on this
company, and ā€“
Jerry: So itā€™s almost like their whole reputation as an investor, if not actually the return
on investment on the fund ā€“
Bijan: And sometimes those are completely intertwined.
Jerry: Right. And so then thereā€™s this intense focus on ā€“ as a company, and you said
youā€™ve seen that and I wonā€™t ask you to name names of course, but what happens
in the boardroom when that kind of ā€“ or what happens in that dialogue when that
kind of pressure is involved? What happens for the CEO, or for the entrepreneur?
Bijan: Well, you know, itā€™s a very tough situation because all of a sudden, the patience
level in the boardroom getā€™s very thin, the fuse gets very short; I mean, these
startups, very few, I mean, you know, weā€™ve backed 108 companies in ten years
and you know, Iā€™m very proud of our track record, but like you know, most donā€™t
work out as you would hoped and then once that you work out require a lot of
time and patience. And when the patience is gone, you know, it creates a very,
very problematic situation. So thatā€™s the thing I see in this scenario where a VC is
on the board, that company is doing, you know, well or reasonably well given all
the challenges in front of them, but yet they have all this, you know, angst put on
them because of what the investor ā€“ you know, the baggage that comes along and
thatā€™s very hard. I mean, I donā€™t have a quick little one-liner on how to deal with
that but I do ā€“ I have seen it and I think when that dynamic gets all messed up,
everything gets harder.
Jerry: Yeah, I relate to that; I both remember it when I sat on so many boards but also
really working as a coach now with entrepreneurs and often times, they are
surprised when I say something that you just said which is that remember the
investor is human. And what I mean by that is of course everybody knows we are
human, but what is surprising is they donā€™t necessarily realize, the entrepreneur
doesnā€™t necessarily realize that the investor is just as subject to anxiety as they
are. And that they too have investors, they too have expectations and sometimes, I
think itā€™s easy to forget that because the power dynamic that exists creates a
license in effect to be aggressive.
Bijan: Right. I think thatā€™s right, thatā€™s a great point, and I think the part that becomes
non-obvious potentially to people that havenā€™t been in this role ā€“ and look VCs,
thereā€™s a lot of very nice things about the life of a venture capitalist but I think itā€™s
ā€“ thereā€™s a hard way or ā€“ I donā€™t want to say unfair, but thereā€™s this way of
looking at a VC and like, theyā€™ve got a portfolio. If this company doesnā€™t work
out, theyā€™ve got more and so you kinda maybe not appreciate that anxiety that
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they have because you know, that portfolio that that fund has, is separate and
distinct but safe from that individual who maybe only has as few investments, and
they feel like their ego and their reputations is intertwined with the success of this
outcome; you know, what Iā€™m saying.
Jerry: Mm-hmm.
Bijan: I think it can easily be chalked up to be like the VC you know, why do they have
to be nervous, they have a bunch of other companies, you know, and thatā€™s not
how real humans interact with these.
Jerry: Well, you know, I think you hit upon another important point which I often
experience when working with clients, you know, we spent a lot of time working
with clients and talking about the emotional rollercoaster that they often ride
where the highs are abnormally high and the lows are abnormally low. And I
often attributed to this phenomena of merging a sense of self-worth with the
success of the enterprise and you know, Iā€™m a Buddhist and one of the things that
we always sort of seek is the kind of equanimity where we are separate from the
action, where our sense of purpose or our sense of being is separated from that.
And listening to you describe it, it feels evocative of the same phenomena which
is you know ā€“ and this is hard because the perception of VCs is that they have so
much money or that they have so much power that theyā€™re not necessarily ā€“ they
donā€™t necessarily warrant sympathy or empathy, and yet theyā€™re just as subject to
the vicissitudes of marrying their sense of self-esteem and self-worth to
achievement of some sort of goal. And one of my favorite quotes comes from
William James, and Iā€™ll paraphrase it now, and what he said was, ā€˜Weā€™re not
annihilated by failure. We are only annihilated when we merge a sense of self-
esteem and self-worth with the attainment of the goal and then fail to achieve the
goal.ā€™ Itā€™s not failure itself, itā€™s not the loss in the portfolio, itā€™s not the loss of this
particular company or a bad investment, or an investment gone bad; itā€™s when my
whole sense of my own being is tied to that achievement.
Bijan: Right, thatā€™s exactly right, yeah.
Jerry: So you resonate with that.
Bijan: I do, I have experienced it firsthand, Iā€™ve seen it firsthand with others, itā€™s a real
challenge and I donā€™t know if this has always been the case so you know, as a
relative newcomer to this field, ten years, you know, we know plenty of people
have practiced this work for longer, but in todayā€™s world, where everything is
public and talked about, and discussed, and ranked, and so much public theater
around you know, VC and you know, this whole business we are in, I feel like
that constant shining a light on, you know, peopleā€™s work performance, I know
why it easily gets caught into the personal sense of worth, you know, when the
two get intertwined in a destructive way; ā€˜cause all of a sudden itā€™s like the highs
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are incredibly high and the lows are incredibly low, and if you arenā€™t able to be
mindful about this, you can get lost, you can really get turned around.
Jerry: So without going into any specifics or giving you the latitude to talk about that,
you know, I think one of the challenges is that when you have a high-profile
portfolio company that has really examined, and explored, and investigated by a
media that quite frankly is kind of prurient in its fixation on the inner workings of,
what one person I know calls, ā€˜Every single shit-show called an entrepreneurial
startupā€™, right?
Bijan: Right.
Jerry: Thereā€™s this exacerbating effect of like ā€˜Oh, you come out of a board meeting and
you find out that the contents of that board meetings are now in TechCrunch.
Bijan: Yeah, yeah, right.
Jerry: And you know, you are trying to experience that. I imagine youā€™ve had your own
experiences with that.
Bijan: I have and you know, I got to tell you, I think thereā€™s some areas that Iā€™m very
happy that I feel like I have gained a healthier perspective on all of this, things
that weā€™re talking about, in terms of patience and perspective and you know, kind
of not ā€“ treating each particular startup that I work with has its own unique thing.
I mean, thereā€™s a lot of examples there where Iā€™ve seen people try to replicate
what works in one company into another and it doesnā€™t work that way. But the
one thing that I still struggle with is like you know, having a thick skin
consistently, you know, about some of these things. I mean, you know, when
youā€™re working with a high-profile company, or a set of companies and you know
people turn on you as it often can be the case, I mean, look at Dick Costolo, I
mean, he went from hero ā€“ I mean, when he took the company public, literally the
press was saying, this was the anti-Facebook IPO. It was this masterful thing he
did, he built the business model out of nothing, he took the company public in a
way that allowed public investors to get appreciation on the value, and it was
masterful. Three quarters later, you couldnā€™t find one piece of good news about
him. Itā€™s just really intense and I know Dick and I know he ā€“ it probably infected
and hit him really hard, and you try to develop a thick skin about these things and
keep a healthy perspective, but Iā€™ll tell you, when they go after you it takes a
special person to be able to withstand those blows.
Jerry: Itā€™s enormously difficult and I remember just thinking about Dick, Iā€™ve only met
him a few times and thoroughly enjoyed him each time, and this is not even a
dialogue about his performance but itā€™s really about the phenomena of not really ā€“
Iā€™m a former reporter so sometimes I can be hard on my journalist friends; I will
say this again about myself, Iā€™m embarrassed by the way I wrote as a journalist in
my twenties because I thought I actually understood business, and I would opine,
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and I would say things that had no basis in reality because thatā€™s the expectation.
And so I am empathetic to the challenge that they have, and yet sometimes I do
wish that people would, you know, use that old adage of walk a mile in
someoneā€™s shoes before they are really willing to criticize. What is it truly like to
sit on the board of directors of a publically traded company? What is it truly like ā€“
especially if youā€™re not a sociopath; and there are sociopaths in the world, thereā€™s
no question about that, right? There are people who are so disconnected from
values and morals and things like that ā€“
Bijan: Yeah.
Jerry: ā€“ but as Iā€™ve gotten older, Iā€™ve come to understand that there are far few
sociopaths in the world than I used to think. So maybe Iā€™ve become a little wiser,
right, and thereā€™s so many people who are just subject to this ā€“ to quote
Shakespeare, to the ā€œSlings and arrows of outrageous fortune.ā€ Itā€™s just one day
you are a hero, the next day youā€™re a goat; and the fact of the matter is youā€™re
never really quite the hero and you never really quite the goat.
Bijan: Right, thatā€™s right. Yeah, I saw David Karp ā€“ you know, we backed David Karp
when he was 19 years old ā€“
Jerry: David Karp from Tumblr?
Bijan: From Tumblr and you know, he was ā€“
Jerry: 19?
Bijan: 19 yeah, and you know, he publically ā€“ you know, theyā€™re saying heā€™s God or a
goat on any given day and heā€™s 20-22; I mean, can you imagine trying to deal
with this? I give him so much credit for the strength that he has to have a vision,
build a company, you know, run the company, and then you know, manage it and
with all this going on, you know, with all sorts of critics. And you know, it just
takes a tremendous amount of personal strength and character. I think itā€™s easier to
overlook just how strong these people are. I know I havenā€™t lived up to my own
expectations in those areas and it can be really tough.
Jerry: I just want to call attention to something; the fact that you are sitting here saying
these things conveys a kind of empathetic understanding that to me speaks to the
carefulness with which you hold your authority and hold your responsibility.
Yeah, ā€˜cause a lot of those 19-year-old kids, they end up on my couch or they end
up on the couch of another coach.
Bijan: Yeah.
Jerry: And I will tell you, you know, there are hearts hurt.
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Bijan: Right.
Jerry: And so the thick skin may be there, but on the inside too, they are really feeling it.
Bijan: Right.
Jerry: They are really feeling it.
Bijan: In fact, Iā€™ve emailed you twice in the last two weeks I think about two ā€“ so Iā€™m a
big advocate for founders getting, you know, a personal coach and somebody that
really is connecting with them in a way thatā€™s most helpful. I mean, itā€™s just so
important and it feels like ā€“ I donā€™t know if itā€™s just where I am right now or
whatever probably, Iā€™m sure you see it, itā€™s just, I feel like there is an acceptance
of this level of assistance that maybe wasnā€™t the case ten years ago or something
like that.
Jerry: It definitely feels that way and I think that thereā€™s been a consistency from the
elders in the community; myself, you, Brad Feld, Fred. Many of the people who
have come on the podcast say this, you know, when thereā€™s a kind of leadership,
when people are willing to talk about the challenges that they go through, thereā€™s
a beautiful byproduct which is ā€“ oh wait, it normalizes the fact that this is really
difficult, and then it makes it possible for people to then share amongst
themselves because you know, I think itā€™s great the amount of interest thatā€™s in
coaching right now. I think itā€™s fantastic, and there arenā€™t enough coaches in the
world.
Bijan: Thatā€™s right.
Jerry: And so one of the things that ā€“ and weā€™re doing this at Reboot where we have
these facilitative peer support groups, but Spark can do it within its own portfolio.
You know, people do this in a variety of ways; God damnit, talk to each other!
Bijan: Right.
Jerry: Actually, if David Karp could speak to Dick Costolo, or if Dick Costolo could
speak to David Karp, to name two of the folks ā€“
Bijan: Yeah.
Jerry: ā€“ and just go, ā€˜Damn, that was hard.ā€™ ā€˜Yup, that was hard, thatā€™s hard.ā€™ ā€˜Okay,
great.ā€™ Then we move forward.
Bijan: Right.
Jerry: To break down the sense of isolation that exacerbates the problem for everybody.
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Bijan: Right.
Jerry: One of the wishes I have, and Iā€™ve been talking to Brad Feld about doing this, is
to actually do a bootcamp for investors. Not so much in the same kind of any of
the training, but to really dive deep into the ways in which you know, what
lessons weā€™ve learned and how can we serve better. Because I really believe in
that servant model that you know, when you take a board seat and you hold that
seat, youā€™re in service, often times to the community thatā€™s built up around the
product ā€“
Bijan: Thatā€™s right.
Jerry: ā€“ as much as it is around the company you are in service too.
Bijan: Right. Yeah, I think that perspective is so important and not intuitive thing
initially, you know, you feel like you know, who am I supposed to ā€“ like whatā€™s
the most important thing I should be doing right now as an investor, as a board
member, and thinking through the community as part of the answer to that
question is really impactful because you know, sometimes you just get caught into
this like founder versus VC thing, or ā€˜Is this the right CEO for the positionā€™ but
like, you got to kinda ā€“ thereā€™s many, many more factors involved in these things
and I think, thinking about the community as an integral part of that decision-
making is just so important.
Jerry: I think that when we hold a sense of service, it kinda breaks down the ego
attachment thatā€™s really behind marrying my self-esteem to the success of the
investment. So weā€™ve discussed like the problem that occurs when my self-esteem
and the self-perception is tied to the success of this one company, or this multiple
investments or something like that, the problems that grow from that are
enormous.
Bijan: Right.
Jerry: And so whatā€™s the antidote to that? Well, the antidote in some ways, I think is to
really focus on the larger purpose, the larger mission and we often ā€“ I donā€™t often
hear about investors thinking about say, ā€˜larger purposeā€™. Whatā€™s the goal here,
beyond return on investment? But really you know, I think of our mutual friend
Brad and his commitment to startup communities ā€“
Bijan: Right.
Jerry: ā€“ and his commitment to the notion of entrepreneurialism as a way for economic
development, which means personal achievement; it means making a difference
in the lives of individuals. This is a larger issue which is, since we are all
members of the ecosystem, my little company Reboot as well, we are all members
of the ecosystem, whatā€™s our obligation and our responsibility to supporting this?
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Because thereā€™s something very precious around these kinds of companies that we
are building; you know, Twitter was an important ā€“ ask the people in Iran if
Twitter is important.
Bijan: Yeah.
Jerry: Or Tunisia; right?
Bijan: Right.
Jerry: Ask those people and thatā€™s ā€“ ask the people if Facebook is important.
Bijan: Right. Yeah, look I totally agree, I mean when Wall Street talks about, you know,
monthly active users and add impressions and all this stuff, what gets lost is when
people like Dick talk about, with utmost sincerity, that he wants Twitter to be the
free-speech wing or the free-speech party. He means that not as a cool, little
sound-bite but like that he really believes in like power to the user, and like
fighting back against governments including our own that are asking for
unwarranted information and things like that. That has nothing to do with, you
know, ā€œshareholder valueā€ or hitting your quarter but you know, when you think
about its importance and significance, those things, you know, you really have to
cherish and celebrate.
Jerry: So when you think about that, and you know, from my lips to Godā€™s ears, youā€™re
not retiring any time soon, and you got another few years maybe five, maybe ten,
maybe twenty, whatever youā€™ve got as an investor, what do you want to take
forward?
Bijan: Take forward in terms of bring to this community or ā€“
Jerry: Yeah. I mean, you spent the first few years learning how to do this job, and you
do it pretty well I might add, and so here you are.
Bijan: Right. Well, yeah, no matter what, I donā€™t feel like my service to entrepreneurs is
going to fade away. I hope to be doing this for ā€“ in whatever shape or form, it
happens for a very long time. And for me, you know, one thing Iā€™ve been thinking
about lately is like you know, if you think about the founder and the entrepreneur
as an artist, like literally as an artist, then a bunch of things become like almost
kinda clear, which is like, you know, their importance to the community is one
thing, the idea that like this is my latest thing to jump up and down about but like
you know, when you see one company excel at a certain way, thereā€™s this
tendency to be like ā€˜Hey, this is how they did it, we should do it this way too for
the next company.ā€™ And ā€˜This company brought in a world-class COO so we
should do that hereā€™ or ā€˜This person you know, upgraded the CEO ā€“ the founder
to an operating executive ā€“ā€™ or something; and when you start having that
mindset, then you forget that these companies are started by artists so. If you
Reboot020_Investors_Human_Too
Page 12 of 15
really think about founders and artists, the idea they are just making these changes
and exporting ā€œbest practicesā€ suddenly becomes important because you canā€™t just
do an organ transplant with an artist. Like, they are an artist, you know, so I kinda
feel like if we can kind of remind each other that we are not dealing with just
Computer Science for the sake of Computer Science, we are dealing with people
that are creating things out of whole cloth and then if thatā€™s the mental model,
then I just feel like our approach to how we interact with each other, how we
conduct ourselves, how we gain a different level of empathy, I just feel like a lot
of understanding starts to ā€“ has a chance to breathe a bit. You know what I mean?
I donā€™t know if this makes any sense but ā€“
Jerry: I think it makes a ton of sense and I have to say you know, as a lot of listeners
know, Iā€™m recording this over Skype so I get to see your face as weā€™re talking
even though we are stripping out the audio; and Iā€™m looking over your shoulder,
two beautiful photographs which ā€“ and I know you, and know you probably took
those photos, is that right?
Bijan: These two, no, I donā€™t hang my own because I just like to celebrate other peopleā€™s
work but yeah.
Jerry: But you have an appreciation for photography as art, as an expression, and I know
thereā€™s a hashtag you often use on Twitter which is something around film, right?
Bijan: Yeah, ā€˜believe in filmā€™, yeah.
Jerry: ā€˜Believe in filmā€™, yeah and thereā€™s a belief that you have in that ā€“
Bijan: Yeah.
Jerry: ā€“ and so that part of you ā€“ and like I wish everybody could see your face right
now ā€˜cause you just lit up; thereā€™s an artist in you, my friend.
Bijan: Well, thanks; I donā€™t know about that but I have a lot of respect for these artists
that we get to work with; right?
Jerry: Yeah, and so it might be safe to say that as you go forward, respecting that artist
is something that perhaps you are stepping into even more so now.
Bijan: Yeah, I think thatā€™s right. It becomes much more ā€“ it has bigger importance than,
you know, everything. Everything else kinda just finds its place when you kind of
think about that in those terms, you know, itā€™s not about you know, just about
shareholder value. I mean, you know, I think you get lost in these ā€“ the other
thing that I think gets lost is like ā€“ and I really ā€“ Iā€™m mindful of your time but like
ā€“ have you ever heard people cite fiduciary responsibility like an act to do
whatever they want?
Reboot020_Investors_Human_Too
Page 13 of 15
Jerry: Yes.
Bijan: Itā€™s like, ā€˜Hey, I have a fiduciary responsibility to treat you like shit ā€“ā€™ or ā€“
Jerry: Right.
Bijan: ā€“ like you know, itā€™s like I feel this fiduciary is a way just to protect, you know,
try to convince yourself of like youā€™re not connecting with the situation at hand,
youā€™re just wielding a weapon.
Jerry: Right.
Bijan: And I just feel like we have to somehow, like you know, remember what we are
doing here, like what is our job here? And the way you described as service is,
you know, Iā€™m stumbling around this a bit, but like thatā€™s exactly the way, thatā€™s
the organizing principle and then things just you know, find their place. The
community service to the artist, the service to the ā€“ thatā€™s what we are doing.
Jerry: I think thatā€™s beautiful and hearing you say that calms me because Iā€™ve been
thinking about reading something to you for a while now, and I wasnā€™t sure
because itā€™s a little bit odd, but itā€™s Jerry and they are used to it, and so here it
goes. Thereā€™s an Irish poet and a former Catholic priest named John Oā€™ Donahue,
and lately Iā€™ve been reading a number of his blessings. He collected a series of
blessings ā€“ he passed away in 2008 and he wrote a series of blessings in a book
called, ā€˜To Bless the Space Between Usā€™ and lately Iā€™ve been reading, ā€˜For a
Leaderā€™ to a number of clients, and the folks who came to our co-founder
bootcamp just a few weeks ago but this is one I was actually thinking of reading
to you as an investor.
Bijan: Okay.
Jerry: And this blessing is called, ā€˜For One Who Holds Powerā€™.
ā€œMay the gift of leadership awaken in you as a vocation,
Keep you mindful of the providence that calls you to serve.
As high over the mountains the eagle spreads its wings,
May your perspective be larger than the view from the foothills.
When the way is flat and dull in times of gray endurance,
May your imagination continue to evoke horizons.
When thirst burns in times of drought,
May you be blessed to find the wells.
May you have the wisdom to read time clearly
Reboot020_Investors_Human_Too
Page 14 of 15
And know when the seed of change will flourish.
In your heart, may there be a sanctuary
For the stillness where clarity is born.
May your work be infused with passion and creativity
And have the wisdom to balance compassion and challenge.
May your soul find the graciousness
To rise above the fester of small mediocrities.
May your power never become a shell
Wherein your heart would silently atrophy.
May you welcome your own vulnerability
As the ground where healing and truth join.
May integrity of soul be your first ideal,
The source that will guide and bless your work.
For one who holds power.ā€
Bijan: Wow, thatā€™s quite powerful. I hope you link to it in your show notes or your
podcast notes.
Jerry: We will. You know, one of the things I like about this is that it speaks implicitly
about the responsibility for one who holds power. To lead from a soul, and to ā€“
you know, I was thinking about this when you were talking about, you know,
entrepreneurs as artists, and allowing the passion and creativity to go into work.
So ā€“
Bijan: Thatā€™s great.
Jerry: ā€“ thatā€™s my blessing for you my friend.
Bijan: I will take it, thank you.
Jerry: Well, thank you so much for joining us in this, it was ā€“ itā€™s been a blast and itā€™s
always fun to see you and talk with you.
Bijan: Same here.
Jerry: Thank you for coming on the show.
Bijan: Thank you so much.
Jerry: All right.
Reboot020_Investors_Human_Too
Page 15 of 15
Bijan: See you soon.
Jerry: Be well.
So thatā€™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 youā€™d like to be a guest on the show, you can find out about that on our site
as well. Iā€™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
youā€™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]
ā€œHow 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.ā€
[End of audio 0:44:30]
[End of transcript]

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Reboot Podcast #20 with Bijan Sabet - Investors are Human too

  • 1. Reboot020_Investors_Human_Too Page 1 of 15 Welcome to the Reboot podcast. Weā€™re proud to say that todayā€™s episode is brought to you by Justworks. Justworks helps businesses take care of their benefits, healthcare, payroll and HR. Itā€™s super-simple and powerful. We use it and we love it. And this podcast really is way more than just Jerry; so we wanted to take this opportunity to introduce you to more of our team, and hear their experience in using Justworks. Ali Schultz: Iā€™m Ali Schultz, and I am the COO of Reboot. Justworks makes my life insanely easy. Itā€™s every HR solution I have ever wanted in one place including my benefits, and I donā€™t have to think about HR things at all. Dan Putt: And how does your experience with Justworks compare to other providers that you may have used in the past? Ali Schultz: I have tried two of the largest HR solutions in the market, and the time that it has taken out of my life to use both of those programs is maddening to me. Back then, at least a couple of years ago, I remember thinking to myself, ā€˜This really doesnā€™t need to be as complicated as it is and I was hoping that someone would create what Justworks has created. I feel like it has kind of given life and a new-found sense of joy and freedom to HR professionals around the globe. Dan Putt: Well, you hear how much Ali loves Justworks and a happy Ali is a happy Reboot. If you are ready to grow your business and not your busy work, head over to Reboot.io/justworks. Youā€™ll find out more about how we use Justworks and how it could work for you. Thatā€™s Reboot.io/justworks. ā€œEveryone thinks of changing the world, but no one thinks of changing himself.ā€ ā€“ Leo Tolstoy. It sounds so obvious, perhaps even tongue-in-cheek, but it also seems to be forgotten enough that it needs to be said aloud again. Investors are human too. They, like the entrepreneurs they back, can ride the rollercoaster of emotions that often come with starting a company; anxieties, fears, excitement, the temptation to merge sense of self with success or failure. What challenges and problems can these emotions create? What tensions can arise between entrepreneurs and investors? Whatā€™s the opportunity for entrepreneurs and investors in recognizing and addressing them? Weā€™re very excited to have only our second investor on the podcast, the wonderful Bijan Sabet. Bijan is a partner at Spark Capital, a Boston-based VC firm that has backed 108 companies including ones we all use and love, such as Twitter, Trello and Tumblr. In this discussion, Bijan and Jerry explore some of the tensions that often arise between investors and entrepreneurs, the emotional perspective of the investor, and the importance of purpose in artistry. As a bonus, it includes Jerry reading a blessing at the end, so stick around for that; for full links, notes, quotes and more, head on over to reboot.io/podcast. Now, enjoy their conversation. Jerry Colonna: Hey Bijan, itā€™s good to see you again; itā€™s been a long time.
  • 2. Reboot020_Investors_Human_Too Page 2 of 15 Bijan Sabet: Great to see you; hi Jerry. Jerry: Yeah, and thank you for coming on the podcast. Now as I was saying before we started recording, you are actually only the second investor Iā€™ve had on. So, itā€™s actually kind of fun and as a former investor and someone ā€“ weā€™ve been friends for a while, Iā€™ve been interested in really exploring more of that relationship between investors and entrepreneurs, and I really appreciate your coming on to spend some time talking about that, and to really talk about, perhaps some of the areas where youā€™ve seen some problems, and some of the areas where youā€™ve seen where it works well. But before I jump in on that, I just wonder what your reaction would be to this notion that the tension that can exist between investors and entrepreneurs is really a problem; am I seeing that correctly? Bijan: Yeah, I mean, it certainly exists for sure. You know, itā€™s funny, this week, this very week is our tenth year anniversary as a venture capital firm at Spark. Jerry: Oh congratulations. Bijan: Tomorrow, actually the 15th is our ten year. So itā€™s a moment for me to kinda reflect on the whole bunch of experiences and all that and yeah, the tension can be real and sometimes itā€™s even there before this relationship starts. Thereā€™s this thing in the blogosphere, or on other things where itā€™s like, hey, you know, be weary of the VC or you just kinda have this dynamic that is sometimes set up in a funky way. Jerry: So, even before the relationship starts to unfold, and what Iā€™m hearing you say is that thereā€™s an almost fear that steps into that; am I naming that correctly? Bijan: I think so. I mean you have ā€“ and obviously thereā€™s fear on both sides but you know, there are some examples where these relationships start with an open mind and a positive you know, disposition I guess, or frame of mind. But thereā€™s somewhere you can kinda feel this guarded world where itā€™s like, ā€˜Hey Iā€™m raising capital, Iā€™m gonna wrap this up in the next ten days and you know, weā€™re having our meeting this week and weā€™re accepting term sheets next weekā€™ and you just feel this wall where you know, little bit of fear, concern, you know, all the stuff and it just creates a very tough dynamic to break through. At least from my standpoint, it creates ā€“ itā€™s very hard to engage that way. As you know, these are very long-term relationships, and if it starts that way, howā€™s it gonna last? Jerry: Yeah. What do you think the root of that is? Where does that come from? Bijan: You know, I think that in all of these things, thereā€™s some curls of truth to this stuff; I mean, thereā€™s plenty of examples of relationships, business relationships, investment experiences that didnā€™t go well and so people try to learn from those lessons and pass them on, but I think as they get cherry-picked these lessons, and as they get kinda reassembled, some of the context is lost. So, you know, the
  • 3. Reboot020_Investors_Human_Too Page 3 of 15 lesson can be like, ā€˜Hey you got to focus on your business, donā€™t waste time with investorsā€™, you know, thereā€™s some merit to that and to be thoughtful about it, and to be mindful of your time but then taken to its extreme, you can get a version of that thatā€™s not awesome. I think probably a lot of this is based on ā€“ thereā€™s like a lot of good lessons then it just gets kinda messed up along the way. Jerry: And what if you learned ā€“ I mean I guess ten years ā€“ and Spark is your first Venture Capital firm; is that right? Bijan: Yes, I really enjoyed your chat with Fred where you know, you had all these different experiences over different history; yeah but for me, this is it. This is all Iā€™ve known. Jerry: So looking back over those last ten years, you know, we didnā€™t plan for this to be a moment of reflection but great, fantastic. So looking back at those last ten years, what are some things that you might have done to contribute to some of that fear in that relationship? Bijan: Yeah, well look, I mean the beginning ā€“ actually Fred told me this early on; I met Fred Wilson before there was Spark Capital. We had a mutual friend, Steve Cain, who introduced Fred when he ā€“ Jerry: Sure, and letā€™s be fair, I introduced Steve to Fred. Bijan: Thatā€™s right, thereā€™s a real connection here and Fred I met, he was in Boston raising money for his first USV fund and before that fund organized, I met him and we stayed in touch but after I became a venture capitalist and we had our fund up and running, I remember he said something to me in passing about like, you know, one of the worst things is a VC who had operating experience, who has no board seats and no venture experience. Like that was a lethal comment or some version that ā€“ Iā€™m probably getting the exact quote wrong, but basically he was talking about me. Maybe intentionally or unintentionally, but you know, an investor with no other board responsibilities, loads of time at his or her disposal, but yet has a track record and an operating experience, that creates a scenario that can be very tough for investors, new investors were you suddenly want to add value, care about these investments, you care about your firm, you care about all these different voices that are coming at you. And you know, Iā€™m sure I know Iā€™ve learnt a lot in the last ten years, but in the beginning Iā€™m sure I was just like, you know, much more kinda hasty about things than I hopefully am today. Jerry: So was there something about having been an operator that made you more hasty? Bijan: I think the natural thing, at least my own experience, and that Iā€™ve seen is that you ā€“ itā€™s a very you know, different job, and so when you no longer have an operating role in these companies but you kinda feel this closeness to the company, that you know, itā€™s like, ā€˜Hey thereā€™s thing not working out here. I
  • 4. Reboot020_Investors_Human_Too Page 4 of 15 know how to fix that thingā€™ and that can be a really tough situation because then youā€™ve gone from, you know, a partner to an unwanted guest in the house. Jerry: Yeah, you know, Iā€™m recalling a similar experience I had when I first became a VC, it was probably my first year with Fred at Flatiron, and I had made ā€“ one of our first investments was an investment I made in a company called Mainspring. The co-investors there, the lead co-investors were Bill Kaiser from Greylock and Paul Maeder from Highland, two pros, gentlemen, thoughtful people who taught me so much about being a good investor. And I remember I came out of an operating background, I had an editorial background, and our first business model at Mainspring was basically an information service in the IT space, and I made the mistake of ā€“ a really rookie mistake of saying, Iā€™m gonna help ā€“ and Iā€™m using that term loosely ā€“ by jumping in and Iā€™ll go up there one day a week and Iā€™ll be the, sort of, quasi-editorial person there. And itā€™s so great you know, doing this and John Connelly, who is an incredibly effective and thoughtful CEO, someone I have learned a lot from as well welcomed that. He welcomed the additional thoughts; I mean, I didnā€™t feel like an unwelcome guest, but maybe I wasnā€™t always as conscious of the feeling. But I remember Bill Kaiser pulling me aside at the end of a board meeting one time and he said to me, ā€œWhat the hell are you doing? Like you actually have to choose; are you gonna be an operator or are you gonna be an investor? You could be a really good operator, but as long as you hold that chair, as long as you take that role, youā€™re actually preventing the company from filling that role.ā€ And it was a shock and I was really grateful for that lesson because I could see, if I had let my ego go forward, ā€˜cause really what ā€“ for me what I was going through was, this venture business, this is scary and I donā€™t really know what Iā€™m doing, shhh, donā€™t tell anybody. Bijan: Yeah. Jerry: But this other thing, this operating role, that I know stone-cold. Bijan: Right. Jerry: So rather than actually thinking about whatā€™s in the best interest of the company, I was trying to manage and massage my own fears by getting all involved, and thinking well about myself by telling myself that I was helping. Bijan: Yeah. Jerry: Does this resonate at all? Bijan: Oh yeah, itā€™s such a great point; I mean, if I were to contrast Fredā€™s comment about the worst thing as an idol ā€“ former operating - now turned investor, my worst nightmare is a VC on the board with me that has a situation where the rest of their portfolio is on fire and this is the shiny company because then you are really in a pickle where you can feel that like unnatural angst and pressure being
  • 5. Reboot020_Investors_Human_Too Page 5 of 15 put on to this company for reasons that have nothing to do with the company. But you see it and VCs are humans and they get stressed and nervous like anybody else and when the rest of the portfolio is on fire and you have this one great company, and all of a sudden they have this unnatural expectations on this company, and ā€“ Jerry: So itā€™s almost like their whole reputation as an investor, if not actually the return on investment on the fund ā€“ Bijan: And sometimes those are completely intertwined. Jerry: Right. And so then thereā€™s this intense focus on ā€“ as a company, and you said youā€™ve seen that and I wonā€™t ask you to name names of course, but what happens in the boardroom when that kind of ā€“ or what happens in that dialogue when that kind of pressure is involved? What happens for the CEO, or for the entrepreneur? Bijan: Well, you know, itā€™s a very tough situation because all of a sudden, the patience level in the boardroom getā€™s very thin, the fuse gets very short; I mean, these startups, very few, I mean, you know, weā€™ve backed 108 companies in ten years and you know, Iā€™m very proud of our track record, but like you know, most donā€™t work out as you would hoped and then once that you work out require a lot of time and patience. And when the patience is gone, you know, it creates a very, very problematic situation. So thatā€™s the thing I see in this scenario where a VC is on the board, that company is doing, you know, well or reasonably well given all the challenges in front of them, but yet they have all this, you know, angst put on them because of what the investor ā€“ you know, the baggage that comes along and thatā€™s very hard. I mean, I donā€™t have a quick little one-liner on how to deal with that but I do ā€“ I have seen it and I think when that dynamic gets all messed up, everything gets harder. Jerry: Yeah, I relate to that; I both remember it when I sat on so many boards but also really working as a coach now with entrepreneurs and often times, they are surprised when I say something that you just said which is that remember the investor is human. And what I mean by that is of course everybody knows we are human, but what is surprising is they donā€™t necessarily realize, the entrepreneur doesnā€™t necessarily realize that the investor is just as subject to anxiety as they are. And that they too have investors, they too have expectations and sometimes, I think itā€™s easy to forget that because the power dynamic that exists creates a license in effect to be aggressive. Bijan: Right. I think thatā€™s right, thatā€™s a great point, and I think the part that becomes non-obvious potentially to people that havenā€™t been in this role ā€“ and look VCs, thereā€™s a lot of very nice things about the life of a venture capitalist but I think itā€™s ā€“ thereā€™s a hard way or ā€“ I donā€™t want to say unfair, but thereā€™s this way of looking at a VC and like, theyā€™ve got a portfolio. If this company doesnā€™t work out, theyā€™ve got more and so you kinda maybe not appreciate that anxiety that
  • 6. Reboot020_Investors_Human_Too Page 6 of 15 they have because you know, that portfolio that that fund has, is separate and distinct but safe from that individual who maybe only has as few investments, and they feel like their ego and their reputations is intertwined with the success of this outcome; you know, what Iā€™m saying. Jerry: Mm-hmm. Bijan: I think it can easily be chalked up to be like the VC you know, why do they have to be nervous, they have a bunch of other companies, you know, and thatā€™s not how real humans interact with these. Jerry: Well, you know, I think you hit upon another important point which I often experience when working with clients, you know, we spent a lot of time working with clients and talking about the emotional rollercoaster that they often ride where the highs are abnormally high and the lows are abnormally low. And I often attributed to this phenomena of merging a sense of self-worth with the success of the enterprise and you know, Iā€™m a Buddhist and one of the things that we always sort of seek is the kind of equanimity where we are separate from the action, where our sense of purpose or our sense of being is separated from that. And listening to you describe it, it feels evocative of the same phenomena which is you know ā€“ and this is hard because the perception of VCs is that they have so much money or that they have so much power that theyā€™re not necessarily ā€“ they donā€™t necessarily warrant sympathy or empathy, and yet theyā€™re just as subject to the vicissitudes of marrying their sense of self-esteem and self-worth to achievement of some sort of goal. And one of my favorite quotes comes from William James, and Iā€™ll paraphrase it now, and what he said was, ā€˜Weā€™re not annihilated by failure. We are only annihilated when we merge a sense of self- esteem and self-worth with the attainment of the goal and then fail to achieve the goal.ā€™ Itā€™s not failure itself, itā€™s not the loss in the portfolio, itā€™s not the loss of this particular company or a bad investment, or an investment gone bad; itā€™s when my whole sense of my own being is tied to that achievement. Bijan: Right, thatā€™s exactly right, yeah. Jerry: So you resonate with that. Bijan: I do, I have experienced it firsthand, Iā€™ve seen it firsthand with others, itā€™s a real challenge and I donā€™t know if this has always been the case so you know, as a relative newcomer to this field, ten years, you know, we know plenty of people have practiced this work for longer, but in todayā€™s world, where everything is public and talked about, and discussed, and ranked, and so much public theater around you know, VC and you know, this whole business we are in, I feel like that constant shining a light on, you know, peopleā€™s work performance, I know why it easily gets caught into the personal sense of worth, you know, when the two get intertwined in a destructive way; ā€˜cause all of a sudden itā€™s like the highs
  • 7. Reboot020_Investors_Human_Too Page 7 of 15 are incredibly high and the lows are incredibly low, and if you arenā€™t able to be mindful about this, you can get lost, you can really get turned around. Jerry: So without going into any specifics or giving you the latitude to talk about that, you know, I think one of the challenges is that when you have a high-profile portfolio company that has really examined, and explored, and investigated by a media that quite frankly is kind of prurient in its fixation on the inner workings of, what one person I know calls, ā€˜Every single shit-show called an entrepreneurial startupā€™, right? Bijan: Right. Jerry: Thereā€™s this exacerbating effect of like ā€˜Oh, you come out of a board meeting and you find out that the contents of that board meetings are now in TechCrunch. Bijan: Yeah, yeah, right. Jerry: And you know, you are trying to experience that. I imagine youā€™ve had your own experiences with that. Bijan: I have and you know, I got to tell you, I think thereā€™s some areas that Iā€™m very happy that I feel like I have gained a healthier perspective on all of this, things that weā€™re talking about, in terms of patience and perspective and you know, kind of not ā€“ treating each particular startup that I work with has its own unique thing. I mean, thereā€™s a lot of examples there where Iā€™ve seen people try to replicate what works in one company into another and it doesnā€™t work that way. But the one thing that I still struggle with is like you know, having a thick skin consistently, you know, about some of these things. I mean, you know, when youā€™re working with a high-profile company, or a set of companies and you know people turn on you as it often can be the case, I mean, look at Dick Costolo, I mean, he went from hero ā€“ I mean, when he took the company public, literally the press was saying, this was the anti-Facebook IPO. It was this masterful thing he did, he built the business model out of nothing, he took the company public in a way that allowed public investors to get appreciation on the value, and it was masterful. Three quarters later, you couldnā€™t find one piece of good news about him. Itā€™s just really intense and I know Dick and I know he ā€“ it probably infected and hit him really hard, and you try to develop a thick skin about these things and keep a healthy perspective, but Iā€™ll tell you, when they go after you it takes a special person to be able to withstand those blows. Jerry: Itā€™s enormously difficult and I remember just thinking about Dick, Iā€™ve only met him a few times and thoroughly enjoyed him each time, and this is not even a dialogue about his performance but itā€™s really about the phenomena of not really ā€“ Iā€™m a former reporter so sometimes I can be hard on my journalist friends; I will say this again about myself, Iā€™m embarrassed by the way I wrote as a journalist in my twenties because I thought I actually understood business, and I would opine,
  • 8. Reboot020_Investors_Human_Too Page 8 of 15 and I would say things that had no basis in reality because thatā€™s the expectation. And so I am empathetic to the challenge that they have, and yet sometimes I do wish that people would, you know, use that old adage of walk a mile in someoneā€™s shoes before they are really willing to criticize. What is it truly like to sit on the board of directors of a publically traded company? What is it truly like ā€“ especially if youā€™re not a sociopath; and there are sociopaths in the world, thereā€™s no question about that, right? There are people who are so disconnected from values and morals and things like that ā€“ Bijan: Yeah. Jerry: ā€“ but as Iā€™ve gotten older, Iā€™ve come to understand that there are far few sociopaths in the world than I used to think. So maybe Iā€™ve become a little wiser, right, and thereā€™s so many people who are just subject to this ā€“ to quote Shakespeare, to the ā€œSlings and arrows of outrageous fortune.ā€ Itā€™s just one day you are a hero, the next day youā€™re a goat; and the fact of the matter is youā€™re never really quite the hero and you never really quite the goat. Bijan: Right, thatā€™s right. Yeah, I saw David Karp ā€“ you know, we backed David Karp when he was 19 years old ā€“ Jerry: David Karp from Tumblr? Bijan: From Tumblr and you know, he was ā€“ Jerry: 19? Bijan: 19 yeah, and you know, he publically ā€“ you know, theyā€™re saying heā€™s God or a goat on any given day and heā€™s 20-22; I mean, can you imagine trying to deal with this? I give him so much credit for the strength that he has to have a vision, build a company, you know, run the company, and then you know, manage it and with all this going on, you know, with all sorts of critics. And you know, it just takes a tremendous amount of personal strength and character. I think itā€™s easier to overlook just how strong these people are. I know I havenā€™t lived up to my own expectations in those areas and it can be really tough. Jerry: I just want to call attention to something; the fact that you are sitting here saying these things conveys a kind of empathetic understanding that to me speaks to the carefulness with which you hold your authority and hold your responsibility. Yeah, ā€˜cause a lot of those 19-year-old kids, they end up on my couch or they end up on the couch of another coach. Bijan: Yeah. Jerry: And I will tell you, you know, there are hearts hurt.
  • 9. Reboot020_Investors_Human_Too Page 9 of 15 Bijan: Right. Jerry: And so the thick skin may be there, but on the inside too, they are really feeling it. Bijan: Right. Jerry: They are really feeling it. Bijan: In fact, Iā€™ve emailed you twice in the last two weeks I think about two ā€“ so Iā€™m a big advocate for founders getting, you know, a personal coach and somebody that really is connecting with them in a way thatā€™s most helpful. I mean, itā€™s just so important and it feels like ā€“ I donā€™t know if itā€™s just where I am right now or whatever probably, Iā€™m sure you see it, itā€™s just, I feel like there is an acceptance of this level of assistance that maybe wasnā€™t the case ten years ago or something like that. Jerry: It definitely feels that way and I think that thereā€™s been a consistency from the elders in the community; myself, you, Brad Feld, Fred. Many of the people who have come on the podcast say this, you know, when thereā€™s a kind of leadership, when people are willing to talk about the challenges that they go through, thereā€™s a beautiful byproduct which is ā€“ oh wait, it normalizes the fact that this is really difficult, and then it makes it possible for people to then share amongst themselves because you know, I think itā€™s great the amount of interest thatā€™s in coaching right now. I think itā€™s fantastic, and there arenā€™t enough coaches in the world. Bijan: Thatā€™s right. Jerry: And so one of the things that ā€“ and weā€™re doing this at Reboot where we have these facilitative peer support groups, but Spark can do it within its own portfolio. You know, people do this in a variety of ways; God damnit, talk to each other! Bijan: Right. Jerry: Actually, if David Karp could speak to Dick Costolo, or if Dick Costolo could speak to David Karp, to name two of the folks ā€“ Bijan: Yeah. Jerry: ā€“ and just go, ā€˜Damn, that was hard.ā€™ ā€˜Yup, that was hard, thatā€™s hard.ā€™ ā€˜Okay, great.ā€™ Then we move forward. Bijan: Right. Jerry: To break down the sense of isolation that exacerbates the problem for everybody.
  • 10. Reboot020_Investors_Human_Too Page 10 of 15 Bijan: Right. Jerry: One of the wishes I have, and Iā€™ve been talking to Brad Feld about doing this, is to actually do a bootcamp for investors. Not so much in the same kind of any of the training, but to really dive deep into the ways in which you know, what lessons weā€™ve learned and how can we serve better. Because I really believe in that servant model that you know, when you take a board seat and you hold that seat, youā€™re in service, often times to the community thatā€™s built up around the product ā€“ Bijan: Thatā€™s right. Jerry: ā€“ as much as it is around the company you are in service too. Bijan: Right. Yeah, I think that perspective is so important and not intuitive thing initially, you know, you feel like you know, who am I supposed to ā€“ like whatā€™s the most important thing I should be doing right now as an investor, as a board member, and thinking through the community as part of the answer to that question is really impactful because you know, sometimes you just get caught into this like founder versus VC thing, or ā€˜Is this the right CEO for the positionā€™ but like, you got to kinda ā€“ thereā€™s many, many more factors involved in these things and I think, thinking about the community as an integral part of that decision- making is just so important. Jerry: I think that when we hold a sense of service, it kinda breaks down the ego attachment thatā€™s really behind marrying my self-esteem to the success of the investment. So weā€™ve discussed like the problem that occurs when my self-esteem and the self-perception is tied to the success of this one company, or this multiple investments or something like that, the problems that grow from that are enormous. Bijan: Right. Jerry: And so whatā€™s the antidote to that? Well, the antidote in some ways, I think is to really focus on the larger purpose, the larger mission and we often ā€“ I donā€™t often hear about investors thinking about say, ā€˜larger purposeā€™. Whatā€™s the goal here, beyond return on investment? But really you know, I think of our mutual friend Brad and his commitment to startup communities ā€“ Bijan: Right. Jerry: ā€“ and his commitment to the notion of entrepreneurialism as a way for economic development, which means personal achievement; it means making a difference in the lives of individuals. This is a larger issue which is, since we are all members of the ecosystem, my little company Reboot as well, we are all members of the ecosystem, whatā€™s our obligation and our responsibility to supporting this?
  • 11. Reboot020_Investors_Human_Too Page 11 of 15 Because thereā€™s something very precious around these kinds of companies that we are building; you know, Twitter was an important ā€“ ask the people in Iran if Twitter is important. Bijan: Yeah. Jerry: Or Tunisia; right? Bijan: Right. Jerry: Ask those people and thatā€™s ā€“ ask the people if Facebook is important. Bijan: Right. Yeah, look I totally agree, I mean when Wall Street talks about, you know, monthly active users and add impressions and all this stuff, what gets lost is when people like Dick talk about, with utmost sincerity, that he wants Twitter to be the free-speech wing or the free-speech party. He means that not as a cool, little sound-bite but like that he really believes in like power to the user, and like fighting back against governments including our own that are asking for unwarranted information and things like that. That has nothing to do with, you know, ā€œshareholder valueā€ or hitting your quarter but you know, when you think about its importance and significance, those things, you know, you really have to cherish and celebrate. Jerry: So when you think about that, and you know, from my lips to Godā€™s ears, youā€™re not retiring any time soon, and you got another few years maybe five, maybe ten, maybe twenty, whatever youā€™ve got as an investor, what do you want to take forward? Bijan: Take forward in terms of bring to this community or ā€“ Jerry: Yeah. I mean, you spent the first few years learning how to do this job, and you do it pretty well I might add, and so here you are. Bijan: Right. Well, yeah, no matter what, I donā€™t feel like my service to entrepreneurs is going to fade away. I hope to be doing this for ā€“ in whatever shape or form, it happens for a very long time. And for me, you know, one thing Iā€™ve been thinking about lately is like you know, if you think about the founder and the entrepreneur as an artist, like literally as an artist, then a bunch of things become like almost kinda clear, which is like, you know, their importance to the community is one thing, the idea that like this is my latest thing to jump up and down about but like you know, when you see one company excel at a certain way, thereā€™s this tendency to be like ā€˜Hey, this is how they did it, we should do it this way too for the next company.ā€™ And ā€˜This company brought in a world-class COO so we should do that hereā€™ or ā€˜This person you know, upgraded the CEO ā€“ the founder to an operating executive ā€“ā€™ or something; and when you start having that mindset, then you forget that these companies are started by artists so. If you
  • 12. Reboot020_Investors_Human_Too Page 12 of 15 really think about founders and artists, the idea they are just making these changes and exporting ā€œbest practicesā€ suddenly becomes important because you canā€™t just do an organ transplant with an artist. Like, they are an artist, you know, so I kinda feel like if we can kind of remind each other that we are not dealing with just Computer Science for the sake of Computer Science, we are dealing with people that are creating things out of whole cloth and then if thatā€™s the mental model, then I just feel like our approach to how we interact with each other, how we conduct ourselves, how we gain a different level of empathy, I just feel like a lot of understanding starts to ā€“ has a chance to breathe a bit. You know what I mean? I donā€™t know if this makes any sense but ā€“ Jerry: I think it makes a ton of sense and I have to say you know, as a lot of listeners know, Iā€™m recording this over Skype so I get to see your face as weā€™re talking even though we are stripping out the audio; and Iā€™m looking over your shoulder, two beautiful photographs which ā€“ and I know you, and know you probably took those photos, is that right? Bijan: These two, no, I donā€™t hang my own because I just like to celebrate other peopleā€™s work but yeah. Jerry: But you have an appreciation for photography as art, as an expression, and I know thereā€™s a hashtag you often use on Twitter which is something around film, right? Bijan: Yeah, ā€˜believe in filmā€™, yeah. Jerry: ā€˜Believe in filmā€™, yeah and thereā€™s a belief that you have in that ā€“ Bijan: Yeah. Jerry: ā€“ and so that part of you ā€“ and like I wish everybody could see your face right now ā€˜cause you just lit up; thereā€™s an artist in you, my friend. Bijan: Well, thanks; I donā€™t know about that but I have a lot of respect for these artists that we get to work with; right? Jerry: Yeah, and so it might be safe to say that as you go forward, respecting that artist is something that perhaps you are stepping into even more so now. Bijan: Yeah, I think thatā€™s right. It becomes much more ā€“ it has bigger importance than, you know, everything. Everything else kinda just finds its place when you kind of think about that in those terms, you know, itā€™s not about you know, just about shareholder value. I mean, you know, I think you get lost in these ā€“ the other thing that I think gets lost is like ā€“ and I really ā€“ Iā€™m mindful of your time but like ā€“ have you ever heard people cite fiduciary responsibility like an act to do whatever they want?
  • 13. Reboot020_Investors_Human_Too Page 13 of 15 Jerry: Yes. Bijan: Itā€™s like, ā€˜Hey, I have a fiduciary responsibility to treat you like shit ā€“ā€™ or ā€“ Jerry: Right. Bijan: ā€“ like you know, itā€™s like I feel this fiduciary is a way just to protect, you know, try to convince yourself of like youā€™re not connecting with the situation at hand, youā€™re just wielding a weapon. Jerry: Right. Bijan: And I just feel like we have to somehow, like you know, remember what we are doing here, like what is our job here? And the way you described as service is, you know, Iā€™m stumbling around this a bit, but like thatā€™s exactly the way, thatā€™s the organizing principle and then things just you know, find their place. The community service to the artist, the service to the ā€“ thatā€™s what we are doing. Jerry: I think thatā€™s beautiful and hearing you say that calms me because Iā€™ve been thinking about reading something to you for a while now, and I wasnā€™t sure because itā€™s a little bit odd, but itā€™s Jerry and they are used to it, and so here it goes. Thereā€™s an Irish poet and a former Catholic priest named John Oā€™ Donahue, and lately Iā€™ve been reading a number of his blessings. He collected a series of blessings ā€“ he passed away in 2008 and he wrote a series of blessings in a book called, ā€˜To Bless the Space Between Usā€™ and lately Iā€™ve been reading, ā€˜For a Leaderā€™ to a number of clients, and the folks who came to our co-founder bootcamp just a few weeks ago but this is one I was actually thinking of reading to you as an investor. Bijan: Okay. Jerry: And this blessing is called, ā€˜For One Who Holds Powerā€™. ā€œMay the gift of leadership awaken in you as a vocation, Keep you mindful of the providence that calls you to serve. As high over the mountains the eagle spreads its wings, May your perspective be larger than the view from the foothills. When the way is flat and dull in times of gray endurance, May your imagination continue to evoke horizons. When thirst burns in times of drought, May you be blessed to find the wells. May you have the wisdom to read time clearly
  • 14. Reboot020_Investors_Human_Too Page 14 of 15 And know when the seed of change will flourish. In your heart, may there be a sanctuary For the stillness where clarity is born. May your work be infused with passion and creativity And have the wisdom to balance compassion and challenge. May your soul find the graciousness To rise above the fester of small mediocrities. May your power never become a shell Wherein your heart would silently atrophy. May you welcome your own vulnerability As the ground where healing and truth join. May integrity of soul be your first ideal, The source that will guide and bless your work. For one who holds power.ā€ Bijan: Wow, thatā€™s quite powerful. I hope you link to it in your show notes or your podcast notes. Jerry: We will. You know, one of the things I like about this is that it speaks implicitly about the responsibility for one who holds power. To lead from a soul, and to ā€“ you know, I was thinking about this when you were talking about, you know, entrepreneurs as artists, and allowing the passion and creativity to go into work. So ā€“ Bijan: Thatā€™s great. Jerry: ā€“ thatā€™s my blessing for you my friend. Bijan: I will take it, thank you. Jerry: Well, thank you so much for joining us in this, it was ā€“ itā€™s been a blast and itā€™s always fun to see you and talk with you. Bijan: Same here. Jerry: Thank you for coming on the show. Bijan: Thank you so much. Jerry: All right.
  • 15. Reboot020_Investors_Human_Too Page 15 of 15 Bijan: See you soon. Jerry: Be well. So thatā€™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 youā€™d like to be a guest on the show, you can find out about that on our site as well. Iā€™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 youā€™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] ā€œHow 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.ā€ [End of audio 0:44:30] [End of transcript]