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Welcome to the startup field guide and
unusual ventures podcast, where we learn from
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the successful startup leaders of today how
the companies truly found product market fit.
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I'm your host sunk here and in
every episode I'll have into a different aspect
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of earnie stage company building with our
guests. Let's go. So in today's
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episode, our guest is a veteran
of the cybersecurity industry, having led three
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successful companies, the latest of which
is Arctic worth networks, last valued at
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about six billion dollars. A W
N is the leader in the cybersecurity category
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known as m Dr, which is
managed detection and response, which it offers
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as a service. And what makes
the story really special is that the company
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had a pretty row first five to
six years and then finally hit a tipping
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point after which the growth of the
business has been just phenomenal. You can
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compare to very few other enterprise software
companies in history to be growing so fast
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at this scale. So welcome to
our podcast the founder of Arctic Wolf,
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Brian Nesmith brand. Please say hi. Thank you. Pleasure to be here.
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And another reason this episode is special
as I have a co host today
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WHO's my partner and the founder of
unusual ventures, John Dry ones. John,
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say hello. John Actually led the
first venture investment, an Arctic Wolf,
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ten years ago, which was a
seven point five million dollar around just
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as Brian started this company. So
it's this interview is going to be really
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epic. It's very special to have
both of you here together. So,
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going back to that moment in two
thousand twelve, Brian, maybe you can
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kick us off by sharing a bit
about, like what was happening when you
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decided to start optical networks. What
was going on in your mind? You
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have done this a couple of times
before. You know how hard it is.
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What was the opportunity? What got
you excited? Sure, so we
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we have to kind of rewind prior
to the official start date, like you
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often do in these things. They
don't come into existence out of nowhere.
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They come from a set of ideas
I had. Ostensibly retired, I actually
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knew John. We joined a small
company that had its own struggles and so
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it got to go John Through.
That experience really well served me well,
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I think when we talked about the
fundraising, because that was a big part
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of the motivation for me, having
worked with a venture company that, especially
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in a challenging dynamic. How do
they behave? What do they do?
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And it was a real strong proofpoint
for me that the partner you get in
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with matters a lot, and especially
when times can get difficult. I got
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bored. The other way of putting
it, I got retired. I got
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bored. It's called up my co
founder, Kim, Kim Tromblay, who's
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based in Waterloo Ontario, and hey, how's those things going? Post you
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know my previous company and think we
worked together at the previous company. Says
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well, on board too, and
that's a bad formula. Two Board.
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You know kind of entrepreneurial folks.
You know, what are they gonna do?
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They're going to jump in and do
something. And so we we got
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together at her over her kitchen counter
in in Waterloo and brainstorm half dozen different
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ideas. Five of the six would
have made it. One would have been
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a complete, abysmal failure and we
decided to focus on this one. UH,
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mostly because I wasn't as excited about
starting a company that was going to
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be get acquired. Not to say
that we couldn't have got acquired, but
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it wasn't going to be a feature. That had to be a part of
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a bigger company, and so I
wanted to be something it was a little
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more category defining. Didn't have to
be category defining, but I thought that
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could be sustained and grow into a
truly large entity, and maybe that created
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some later challenges for us and what
we were doing, but that was that
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was really the start of everything there. And what was kind of the market
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insight? What were you looking we
decided to start a company? What were
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you looking for in terms of an
actual problem to chase and why? So?
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The actual space we focused focused on. People today call it m Dr,
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that managed detection response. I look
at it is like neighborhood watch for
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your I t infrastructure. So it's
collecting data from the environment understanding when things
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are not doing what they should be
doing. We called it continuous monitoring.
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At the time the essence of the
idea came from my prior company, bluecoat.
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BLUECOAT, the security solution produced really
voluminous locks, like massive locked data,
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huge wealth of information that data.
We found it very rare that a
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customer was able to understand what that
data was telling them, and so that
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was the kernel of the idea.
If you look across everything that's in your
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environment. You know your endpoints,
your servers, your security devices, your
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firewalls, every one of them is
producing data. There's a huge amount of
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wealth in that data mixed with a
massive amount of noise, and so the
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thought process was we could build a
solution that would get through all that and
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draw out the specific items that are
relevant to the end customer. Um and
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you know, and that we called
a continuous monitoring and evolved over several iterations,
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through different names, into what we're
doing. But that was the original
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insight and the thought process of what
we wanted to build. And John,
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as an investor, what was exciting
about the problem area Brian wanted to focus
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on peat your attention. Well,
it actually all started with Brian. You
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Know Brian and I, as he
had said, we worked on a board
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together. I had recruited him to
an early stage company and had worked with
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him through multiple rounds of funding and
unfortunately, not a great exit. I
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don't know if Brian knows this,
but when I was business school at Stanford
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we actually studied cash flow or blue
coat. So I remember him as the
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protagonist in that case. And you
know my mentor, Andy Ratcliffe, and
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Brian worked together. Andy as an
investor and Brian, Brian as the CEO.
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So we we had that history.
And then Brian is on the proud
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father of daughters like myself and also
a lover of soccer. So we had
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hit it off both on a professional
and a personal level. So when he
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came to me I was already positively
inclined about anything that he was going to
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do, although I did think he
was retired. So I was a bit
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surprised when he came. But he
made his very compelling argument, as the
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good founders do, about why the
industry was changing, why there was a
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need for what Arctic Wolf would inevitably
become, and it felt like he had
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what we call that proprietary insight.
He understood the market and how the world
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was evolving and he saw the opportunity
uniquely because of his experience. So a
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combination of those two things, I
was really excited to work with Brian again.
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Well, so, going back to
two thousand and twelve, you've raised
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your seed round from John and then, I think very soon after you actually
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also did a preemptive a which almost
feels like you're back in one but but
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you know, you did this way
back before. It was the norm.
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You had a preemptive a round led
by red point. What was happening on
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the product side? Like, as
a repeat founder, like, how did
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you approach developing the product, testing
the hypothesis? What was the product market
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for journey for optical? Yeah,
so just a slight correction there. So
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the light speed was the a round
with John and then the B round was
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with red point. It was a
fairly simple process. Red Point had missed
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out on the a round. They
did not get selected in the person that
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was leading at just wanted to get
into the D l. So he came
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to me and we weren't actually trying
to raise money at that time and we
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just added the money at that point
in time. Uh. That being said,
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a lot of this is when you
you have an idea of a company.
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You have an idea, if you
think something's gonna want, you don't
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actually know if it's true, like
and you don't really know if it's true
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until you go out and try to
get somebody to pay money to buy it
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from you. And so that's that
to me. Uh, I you know,
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I started with a group of engineers. I was the only non engineer,
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even though I have an engineering degree
I was. I haven't really practiced
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engineering, so I'm no longer can
qualify as an engineer in the truest sense
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of the word. I spent most
of that first year, year and a
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half, selling early like starting to
think about, you know, who's the
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target customer? What's that profile look
like? Um, and a realization,
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especially for a B two B business. Uh, it's it's there's a lot
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of direct interaction with the customer and
so you've got to do a bunch of
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things to kind of help you figure
out how you're going to get that product
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market fit. One of the things
things that I think is a common misnomer
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is, I think it's a question
that comes all the time, how do
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you know you have product market fit? And I don't think that's actually the
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best question. I think what's really
important is what is the process? How
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are you going to go about learning
how you're going to get product market fit?
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Because product market fit is is,
you know, hard work, it's
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intelligence, it's luck. You can't
control everything there, but the process you
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go through and figure out how to
get a product market fit for a B
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two B company, I think is
something that can be done and you can't
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dictate the outcome, but you can't
dictate the process. And so could you
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walk us through, like what that
process felt like? A doctical sure,
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and it's simplest form, and you
see this illustrated if you talk about people
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doing fundraising and say what's Your Elevator
Pitch? I don't think that's good enough.
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So that you think about it is
is you get five seconds to get
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somebody to listen for fifteen seconds and
in fifteen seconds to get a minute,
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in a minute, to actually ask
for a meaning, to talk about what
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you do. So those three sessions
and ultimately the pitch that you're going to
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give them to get them to buy
the product, those have to be scripted
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and you don't have to wait to
have the product that you want to sell
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to do those scripts. You can
go test them, start learning and iterating.
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Uh, and I actually wrote those
scripts out early, early on.
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I was the only one doing that. I was the sales development rep the
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SDR. I was the SDR that
would give them the fifteen second pitch,
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I was the one that would do
the one minute pitch and then I did
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an interesting thing. I created an
alter ego early, early on. That
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was not me. As the CEO
but me as a salesperson. I called
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that person Brian Robinson and Um and
I was I was Brian Robinson doing the
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sales pitch because it's it's for some
customers you get a different dynamic whens the
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CEO selling, but when it's this
sales guy. And so you know,
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I would do that pitch and and
do it as Brian Robinson. And it
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also afforded me if people would ask
for discounts or they'd want help, I
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could say, well, you know, I gotta talk to the CEO and
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we'll see what he can do.
And I did get caught once. I
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fest up immediately, but it happens. But it also it kind of put
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in me the idea that I'm not
the CEO selling right now. What does
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that pitch got to look like?
It's the story itself, not my personality
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or not my title is not going
to get me the meeting. And wrote
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those scripts, did him myself,
before I hired anybody in sales, many,
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many times iterated on them and and
even after I started hiring people into
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those specific positions, still participated fairly
actively in selling right along with those people
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and listening to them. But I
also reserved, even as we're still learning
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that product market fit with as I
hired people, I reserved about capacity for
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an alternate script. So and then
I would hold once a quarter I'd hold
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a free day. Everybody can try
their own script and tell me what work.
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It can't be what we do now
and just trying to find ways to
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iterate and create that rapid learning dynamic. I think I articulate to people you
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can't dictate the outcome. You're going
to get product market fit. You're not
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guaranteed to get it, but what
you can do is control the process and
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be as an efficient as possible about
what doesn't work. And it can be
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frustrating and painful because I guarantee you, anybody that does this, you will
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get a lot more but what doesn't
work than what does work. You may
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go through hundreds of iteration of what
doesn't work and until you find what does
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work. One of the things about
Brian that was so compelling was his perspective
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on the market but at the same
time his willingness to continue to try different
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scripts, as he called them.
Right. So he, he and Kim
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had this fundamental insight about the security
market being broken in the sense that it
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was most companies were cobbling together a
bunch of point products and then building a
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security operations center to try to really
get to the root cause of a lot
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of the most recent attacks. And
he just saw that because he had been
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one of those point product vendors and
he saw the opportunity to build a platform
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that brought a lot of that data
together. But how to articulate that right?
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How to to compel a customer about
the value proposition when they were accustomed
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to buying something else, more of
a point product? It took time,
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it took a lot of time and
it was a creative process that's very difficult,
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difficult to put a schedule too.
But he would always come to us
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as investors with these different these different
scripts right, these different positioning statements,
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these different narratives as he was working
his way through the process and, as
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he said, there's no guarantee of
the outcomes of success, but he knew
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that by following a process and continuing
to iterate and iterate, iterate, he
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was he was maximizing his probability of
finding it makes sense. And Brown,
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I am curious, like, how
do you what were the reactions you looked
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for in a pitch to say,
Oh, this meeting went very well.
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I think my my bios like leaning
in hard versus. They said Nice things,
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but actually that meeting was a complete
like. Could you share examples of
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how have you built your own engage? Well, it so the five second
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pitch. Did you get a fifteen
second pitch? I actually literally tracked that.
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And then the fifteen second do I
get a minute? And I would
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understand. No, they hung up
after fifteen seconds. Okay, well,
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something in the five or fifteen didn't
work. Uh. And then sometimes I
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get to the minute pitch and I'd
say hey, could you take a fifteen
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minute meeting when I'll give you a
more thorough overview? They'd say no,
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you know, they kind of yeah, they're being polite, and I'd say,
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Hey, could you share? Could
you for a minute here, share
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to me? Why not, like, tell me what you didn't like or
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what didn't resonate with you, and
and I would encourage them, because of
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what I would do is I criticized
myself. I think you didn't like this,
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because then that opens the door,
because people are naturally generally polite.
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They won't tell you why they don't
want to do it U and you know,
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ultimately it's very obvious. Your five
second pitch gets you the majority of
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the time of fifteen second and fift
and gets you the minute in your minute
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gets you the full meeting, even
for the full meeting that was scripted and
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pitched. And you know, we
would try to get customers too. We
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did something a little different. In
a typical generally in an enterprise level product,
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people want to do a POC.
I didn't want to do pocs.
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So what we would do is we
would get customers to buy the first month's
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service. And so we did not
do POC S. it's like, I'm
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not going to do a POC.
This is worth it to you, uh,
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and I'll put you on a month, a month subscription and and so
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pay for the first month. And
if you're not willing to pay for the
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first month, then my guess is
the POC would have been a waste of
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our time. So it's every step
of the way asking for the order.
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You know, five seconds, can
you give me fifteen? Can you give
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me a minute? A minute,
can you give me that? You know,
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fifteen minute meeting. And in that
fifteen minute meeting, are you ready
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to buy it, you know,
because I'll only charge you a month and
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if you don't like it, you
can cancel after a month and you can
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move on. And and it's hard, I think as an entrepreneur you don't
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like rejection, you know, and
so you know it's your little baby that
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you're building and you know, they
run it for a month and they say,
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yeah, it wasn't worth it to
me, and you know, there's
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a lot of lessons. You may
have the basic idea right, but I
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guarantee every entrepreneur has to iterate on
even the basic idea to really turn it
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into something that's truly going to be
successful. What was some of those atuations
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like that? You know, do
you remember kind of the very first original
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form of the idea and then how
you guys evoluted based on the feedback?
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It was mostly, I saved marketing
pitches, how we talked about we did
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continuous monitoring, we had soccer as
a service, we had SIM as the
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service. We had even had this
term firebreak, which I think was kind
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of reaching the pinnacle of my team
getting frustrated with me. So it's uh,
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you know. So I as mostly, I'd say, iterations on that
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piece. Ultimately, all that aside, by focusing on the process and measuring
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it, you get to reward yourself
that I've I've learned, things I've I've
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things that I've improving the product,
things that I'm improving how I talk about
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things here. We didn't really achieve
product market fit, and I think this
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is a lesson for people is it's
not always about your iterations. Sometimes the
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market just has to come your way. And for us, you know,
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five and a half years into it, uh, if you know, our
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audience might remember, but the big
ransomware events occurred with the UK hospitals change
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the dynamic of our space because prior
to that, yeah, hackers get into
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your network, they steal your stuff, so what wasn't that big of a
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deal? Yeah, they say it
is a big deal, but they didn't
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really care about it. When those
ransomware events return those hospitals to the dark
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ages, AL sudden everybody woke up
and said, hey, hacker could bring
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down my entire infrastructure, and so
everything shifted. You could just feel the
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win. When you talk to people
that are like, Oh, somebody that
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would watch and tell me when that's
about to happen and warn me and correct
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me and then they just start taking
stuff away from you. They can't stop
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you. They're they're like yeah,
let's do the meeting, yes, let's
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take the next call, let me
get my other team on the phone,
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all those sorts of kind of signals
that tell you on that and those are
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the indicators of it. But ultimately
the real indicators people buy it and they
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keep it installed. It tells you
more than anything. And this was like
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two thousand seventeen eighteen, right about
five six yels after optical was born.
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So what were what was that kind
of you know wandering through the wilderness process
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like, like what, what did
the board conversation sound like when you went
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back and said no, we're still
figuring it out. We didn't get this
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is what made it especially frustrating.
It's not that there was no success.
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So it's like we're getting some traction. And I joke even today, you
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know, we've been doubling for almost
ten years and so every year we're getting
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growth. It's just not in the
traditional model. It wasn't like three times,
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three times, two times, two
times. It's been, you know,
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two X, two X, two
x two X, and out the
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size. We're getting the two x
start to matter, and so not every
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company grows the same way. And
I think that a couple of things.
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One, I have the experience where
I've lived it and I was comfortable being
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fully transparent, like where we screwed
up, where we made mistakes, where
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that was a waste of money,
and okay, well, that wasn't a
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waste of money, but I did
learn something, you know, and moved
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on from that, and that's the
benefit of experience. But I think even
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a young entrepreneur, there's there's no
reason not to be transparent. It's you'll
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just benefit measurably like that, just
even for your own psyche, that you're
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not trying to maintain two sets of
books in your heads about what you told
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your investors versus what's actually happening for
whatever reason, and and we just you
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know. I think that, coupled
with I saw enough proofpoints in the individual,
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not in the overall market, in
the individual where people did rip it
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out of my hands and I believe
that eventually the market would come about.
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I the, you know, misleading
to tell you that I knew was going
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to be the ransomware event that was
going to cause that. But I knew
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something would happen in our space that
would that would trigger that kind of event
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to take place, and so that
transparency and and then also just, you
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know, sharing the anecdotal information about
when it was successful and what made it
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successful and as proofpoints that this is
going to happen. Yeah, I mean,
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Brian, you can't under understate that. I think for our audience right,
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the fact that Brian was brutally honest
and brutally transparent, it actually gave
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us confidence in him right to continue
to persevere. You know, I think
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way too often vcs believe in this
mythical well, it's supposed to triple,
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it's supposed to triple and then double
double. But it's an artificial growth rate
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that you're putting on a startup and
while we'd all love to see those happen,
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it's unrealistic, especially when you're creating
a new category, that that company
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is going to grow according to some
spreadsheet exercise. And so I think what
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happens is rounds happen, valuations go
up and all of a sudden people with
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hindsight say, Oh, we're supposed
to triple, triple, double double,
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and when they don't, they kind
of panic and in this case, because
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Brian was so transparent and so truthful
about the struggles, uh, and,
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you know, the moderate successes we
we continue to have. Believe, I
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certainly did, in him and believing
that eventually the market would come around if
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we could really figure out how to
position and get the narrative right. And
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I think that was that was true. He's underselling his ability to continue to
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do that, but it also was. There was a macroeconomic shift in peoples
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thinking and sometimes it's just about being
around, surviving until that happens and having
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the antidote. You know, in
this case that people really recognize now that
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they needed. Makes Sense and ran
onto a very important question, especially in
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this environment. How did you think
about, like your bull and your teeth
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while you were kind of going through
this uh, you know, more of
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the woodenest spat right, like the
big dipping point hasn't happened yet. You
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can see that. How did you
think about, you know, planning your
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team expansion accordingly, and what did
your team look like, you know,
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in the you know, three,
maybe two or three years in for the
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first two, two and a half
years, it was me and a bunch
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of engineers. So I was selling
and marketing and doing all the pieces that.
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My marketing skills aren't great, my
design skills aren't great, but but
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what I, you know, was
comfortable doing as selling and and doing the
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pitch and and I didn't think I
needed, you know, something too fancy
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to articulate the value proposition to the
customers. So, uh, now does
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it start to iterate and you start
getting a little bit of traction. And
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we started adding resources, paying attention
to the metrics, like you know,
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having five of something, are you
learning any better or any faster than having
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two of something? If two of
some things you're learning fast enough, then
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don't add more. So you really
prove a formula. Although we've raised a
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lot of money, you know,
over the history, through the early you
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know, through all the way up
even the d round, we had not
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raised that much money. We made
it last a good six, six and
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a half years, and it's really
on the last couple of rounds. Did
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the fundraising, you know, increase
in the volumes increase? Uh Uh,
335
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and so it's just being measured and
being honest with yourself, like you know,
336
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it's running a big marketing campaign and
to change it in our particular world.
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Now. I didn't have trouble getting
to people to give them my initial
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five second pitch, you know,
and so that's not my problem then.
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Okay, it's it's that steps to
the to the other funding. To just
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be cautious when you're doing it now. It's very different for a b two
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C or some other type of company. For A B two B company,
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there's no reason you don't need a
big, massive marketing spit, you know,
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spending, launch and all those things
to kind of prove that people really
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want to buy you're selling makes sense
and you know. So kind of looking
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at that time period again, Um, you probably needed to like go out
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raise that next round before the tipping
point had really played out, and so
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you know you have the pressure of
being compared to like the gold standard or
348
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even triple for three years benchmarks.
What was your fundraising process like, like
349
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joint has John has given me a
spoiler alert here that it was really tough.
350
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So would love to dig into that
and it really help all the founders
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who are going to pretty much go
through the same experience in the next eighteen
352
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months or so of fundraising in a
very challenging environment where the standards have been
353
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raised extremely high for, you know, ABC rounds. Would love to hear
354
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from you kind of what your approach
to fundraising in that environment was. So
355
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yeah, the A and the B
round, I think, just my reputation
356
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historical experience, were fairly straightforward.
So we're talking about the B two.
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I'll talk about why we call it
a b to the c and the D
358
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hard would be an understatement. They
were full on agony and you know,
359
00:25:15.880 --> 00:25:18.480
the B two round kind of should
have indicated to me. So I I
360
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and now, at the benefit of
hindsight, I go back and look at
361
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it. Uh. I'd like to
tell you that the venture world is Um
362
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you know that everyone really kind of
looks through to the root of everything and
363
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understands it. Is Willing to swim
against the tide, but it's a momentum
364
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style business, like a lot of
public markets are. Uh. And we
365
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had two negative things going with this. Is that what we were doing as
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a service was delivered as a service. It wasn't a product company and I
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think the experience in the venture industry
and generally with service companies has not been
368
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great. Like it's been pretty bad. Uh. And the second part is
369
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our initial focus when I found through
my iteration small customers were the best fit.
370
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Not so were small, but kind
of the one five employees and that
371
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type of investment has generally not played
out well for a lot of venture investors.
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So even going into the pitch for
the B to the C and the
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D, which is well, you're
selling the small companies and you're selling a
374
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service. Okay. And then on
top of that, uh, you know,
375
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the the metrics, we hadn't grown
into them yet. So we weren't
376
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experiencing that kind of growth that John
alluded to, that they like to see.
377
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And and even though I think we
were getting good traction m the B
378
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two frankly happened, because I think
in the end I talked to probably a
379
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D plus companies in the B two
round and they all said No. I
380
00:26:38.079 --> 00:26:41.839
had a three or four that got
close but ultimated up at no. One
381
00:26:41.880 --> 00:26:45.359
in particular one potenture venture group.
It was a split one partner one to
382
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do it, the other one to
not, and I actually got blackballed by
383
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the other partner, as I come
to find out through history. there.
384
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Uh, and then John and I
we both put some of our personal money
385
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in that kind of set. The
round. The B two was done at
386
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the same value was the b a
year and a half later. So there's
387
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no increase. You arguably could call
it a down round. Uh and the
388
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way, I don't think of it
like that, I know other people do.
389
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We needed the money and I would
have taken the money at that price.
390
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I would have taken the money even
at a lower price. But we
391
00:27:15.480 --> 00:27:18.319
did the down round, I think, with me stepping up, John Stepping
392
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up on the personal side, and
then we created the metrics we were then
393
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got some of the existing investors to
participate, not all of them, Um
394
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and and then we were able actually
with that able to add a few others.
395
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We added a country company out of
Europe and atypical investor and a few
396
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others to round out the round.
So we did the B too. The
397
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C was probably my lowest point in
the company. At that point I went
398
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and talked to hundred and fifty plus
companies. Partly, I think. Now
399
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you've got to remember, still got
the small business, still got the delivered
400
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as a service. Now you've got
the failed success of the B two,
401
00:28:00.200 --> 00:28:03.039
or the failure of the B two, kind of hanging over you as this
402
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rain cloud. Um and I had
talked to everybody and got nos across the
403
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board. Actually went to a session
with John and and John I to his
404
00:28:15.680 --> 00:28:18.119
credit, this company would not be
here without John Going to the wall with
405
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the WHO became the lead ultimately Um
in the sea round and Um and I
406
00:28:25.359 --> 00:28:27.960
think they did as much off of
John's reputation and what they're doing and they've
407
00:28:27.960 --> 00:28:33.160
obviously done very well that investment um
as a result. Yeah, they look
408
00:28:33.279 --> 00:28:38.319
like geniuses, I think. I
think it's fair to say that John looks
409
00:28:38.359 --> 00:28:42.519
like the genius. So as as
the piece there. But you know,
410
00:28:42.680 --> 00:28:45.200
it was, I mean just to
give you sow, disheartening. Was I
411
00:28:45.279 --> 00:28:48.559
had scheduled a two week vacation with
my family to Italy and I canceled it.
412
00:28:49.119 --> 00:28:52.519
Um and the rest of my family
went off to Italy in that vacation.
413
00:28:52.559 --> 00:28:55.759
I'm not sure my wife has forgiven
me to this day for for doing
414
00:28:55.839 --> 00:28:57.839
that. And and it was.
It was as stressed as I think I've
415
00:28:59.000 --> 00:29:02.519
I've been in a long time related
to work related items. Uh. But
416
00:29:02.640 --> 00:29:06.920
then John Stepping in, we made
the pitch. Uh, they did invest.
417
00:29:07.000 --> 00:29:10.319
We had a few other smaller people
follow along with that lead investor Um
418
00:29:10.759 --> 00:29:15.359
and not a very, very small
uptick you know the the pre money.
419
00:29:15.640 --> 00:29:21.200
You know, the valuation was right
around posts the B and the B two,
420
00:29:21.599 --> 00:29:22.920
and we only went up to like
a hundred forty million. You know,
421
00:29:22.960 --> 00:29:26.480
where people are used to jumping hundreds
of millions, you know, even
422
00:29:26.559 --> 00:29:32.720
into the billions of that category.
And then the d round, same thing.
423
00:29:32.799 --> 00:29:37.000
Now this is kind of now two
thousand seventeen. I did get one
424
00:29:37.119 --> 00:29:40.839
particular investor of pe firm that wanted
to invest, but Um, it was
425
00:29:40.880 --> 00:29:44.559
a bit of you give your soul
over to them. They control everything about
426
00:29:44.599 --> 00:29:47.279
it, and we said No.
I said No. I remember sitting in
427
00:29:47.319 --> 00:29:48.880
the board meeting and they're like yeah, you can take this money, but
428
00:29:48.960 --> 00:29:52.359
you don't. You don't have anybody
else ready to do it at this point
429
00:29:52.359 --> 00:29:55.799
in time. But it comes at
a price and we chose not to and
430
00:29:55.880 --> 00:30:00.519
we were able to stitch together around
with blue cloud and STEREOCAP, not your
431
00:30:00.559 --> 00:30:03.599
atypical not your typical investors, and
then we got other people to follow on
432
00:30:04.119 --> 00:30:08.759
Um and then after that it became
pretty easy. Uh, I you know,
433
00:30:10.119 --> 00:30:14.680
I fundraising is either ridiculously easy or
ridiculously hard. I don't there's usually
434
00:30:14.720 --> 00:30:18.599
not a middle ground and these things, and it was ridiculously hard for everyone
435
00:30:18.359 --> 00:30:22.240
and honestly I was a bit surprised. People that I knew and had worked
436
00:30:22.279 --> 00:30:26.079
with before said No. Other folks, I had multiple firms say no more
437
00:30:26.160 --> 00:30:30.119
than a few times. Even as
part of the D round. I had
438
00:30:30.160 --> 00:30:33.400
one particular firm, a very well
known firm in the valley, called me
439
00:30:33.519 --> 00:30:37.119
in say no, call me back
in again and talk to him again and
440
00:30:37.160 --> 00:30:38.480
they said no again, and then
call me back in again. So I
441
00:30:38.559 --> 00:30:41.559
got so I didn't just get one
rejection in that d round, I got
442
00:30:41.680 --> 00:30:45.839
three from that firm. Uh as
they I think we're struggling how to think
443
00:30:45.880 --> 00:30:49.440
about it so and what to do. But you know, if you believe
444
00:30:49.519 --> 00:30:53.279
in it, you know and you
can. You know, you kind of
445
00:30:53.359 --> 00:30:56.359
bet and you've got to be willing
to fail also, like at some point
446
00:30:56.440 --> 00:30:59.960
you know it's yeah, it was
a non zero chance it could have all
447
00:31:00.000 --> 00:31:03.400
failed. Yeah, I think you
have so many follow up questions. Let's
448
00:31:03.799 --> 00:31:07.880
think first, I think question for
John, like what what gave you the
449
00:31:08.079 --> 00:31:14.319
conviction, because you know you have
to decide as an investor and you have
450
00:31:14.480 --> 00:31:18.480
multiple companies that you know, some
of which are struggling, all of which
451
00:31:18.599 --> 00:31:21.759
need your help. You have to
kind of decide like, okay, where
452
00:31:21.839 --> 00:31:26.880
are you going to really, you
know, do something monumentally different? And
453
00:31:27.359 --> 00:31:32.640
so I'm curious what gave you the
conviction to step in with Brian and,
454
00:31:33.200 --> 00:31:34.960
you know, go to the wall, like you said. Well, it's
455
00:31:36.000 --> 00:31:37.359
definitely not that I was a genius. So I think we need to just
456
00:31:37.680 --> 00:31:41.920
make that really clear. Anybody who
knows me knows that's already true. But
457
00:31:42.200 --> 00:31:45.759
honestly, it was mostly about Brian
in the end. You know, back
458
00:31:45.799 --> 00:31:49.680
to that transparency, that that belief
in and you know, we're I'm a
459
00:31:49.720 --> 00:31:53.119
bit of a product nerd myself,
and so I had done a lot of
460
00:31:53.240 --> 00:32:01.440
work around the space and the customer
problems and increasing just had conviction, uh,
461
00:32:02.599 --> 00:32:07.599
both in Brian and the need in
the marketplace and that our solution in
462
00:32:07.720 --> 00:32:09.880
Arctic Wolf was actually the right one. It was just going to be a
463
00:32:09.960 --> 00:32:15.319
matter of time and, you know, not being afraid of the grind right
464
00:32:15.440 --> 00:32:19.160
and you know, as an investor, you you make investments and then you
465
00:32:19.400 --> 00:32:22.319
it's almost like a poker game.
You you turn over some cards, you
466
00:32:22.400 --> 00:32:24.799
have more data and you have to
decide do you want to stay in the
467
00:32:24.880 --> 00:32:28.839
game and keep and keep betting or
do you do? You do you want
468
00:32:28.839 --> 00:32:31.599
to fold based on what you know, and in this case I was really
469
00:32:31.680 --> 00:32:37.200
convinced that the right answer was to
stay in Um, you know, maybe
470
00:32:37.279 --> 00:32:40.240
more than any other investment I've been
a part of. And so over time,
471
00:32:40.640 --> 00:32:45.880
you know, there were those nuggets
of success that continue to give everyone
472
00:32:45.000 --> 00:32:51.079
belief. But to Brian's point,
a lot of times investors don't like to
473
00:32:51.599 --> 00:32:55.039
acknowledge they made a mistake. So
we we did have this overhang where we
474
00:32:55.079 --> 00:33:00.559
had tried to pitch the story before
people said No. Um. Some of
475
00:33:00.599 --> 00:33:04.400
the other early investors, the funds, they you know, despite being multi
476
00:33:04.519 --> 00:33:07.960
stage funds, they weren't stepping up
in a meaningful way, like they just
477
00:33:08.039 --> 00:33:14.799
were a lot of issues that created
headwind for Arctic Wolf Um. And then
478
00:33:14.839 --> 00:33:17.599
when it was obvious Brian was beating
people away with a stick, I mean
479
00:33:17.759 --> 00:33:22.400
just people throwing money at him like
you wouldn't believe. But those three financings
480
00:33:23.000 --> 00:33:28.119
they were lean, they were leaning, you know, scrappy years Um.
481
00:33:28.279 --> 00:33:31.119
So it's just really a credit to
him and the team that they they persevered.
482
00:33:32.119 --> 00:33:36.279
And the follow up question for you, bran, what what do you
483
00:33:36.359 --> 00:33:40.240
think in hindsight? I think two
separate questions. One in hindsight, what
484
00:33:40.839 --> 00:33:45.039
you know? What? What decisions
do you feel like you made that helped
485
00:33:45.119 --> 00:33:51.480
you survive through that phase where you
might potentially be seeing other people trip up,
486
00:33:51.640 --> 00:33:53.720
like how do you survive? And
it's lean and you need to kind
487
00:33:53.759 --> 00:33:59.480
of wait for the market to meet
too in terms of readiness, and then
488
00:33:59.559 --> 00:34:01.559
too, you know, what would
you do differently if you had to do
489
00:34:01.680 --> 00:34:07.359
it again? In terms of the
whole fundraising process itself? Well, he
490
00:34:07.480 --> 00:34:12.000
had an amazing spouse. What's going
right there? That was the real reason
491
00:34:12.119 --> 00:34:15.320
that he go ahead. But I
know you're gonna say that, yeah,
492
00:34:15.840 --> 00:34:19.280
I mean that is a big part
of it too, is that you know
493
00:34:19.360 --> 00:34:24.039
this. These these comment a significant
personal sacrifice, you know, not not
494
00:34:24.239 --> 00:34:29.239
just time but energy and psyche and
stuff like that. You know, and
495
00:34:29.320 --> 00:34:32.599
you can live through some pretty dark
times where just why don't, why doesn't
496
00:34:32.599 --> 00:34:36.039
everybody get what I get? Like, I don't understand this. It's like,
497
00:34:36.239 --> 00:34:39.239
you know what's what's happening there.
Um, you know, I I
498
00:34:40.280 --> 00:34:45.880
know. My my advice is,
uh, you know, for someone here,
499
00:34:45.360 --> 00:34:52.960
is that you know, you you
you know the transparency that's required.
500
00:34:52.000 --> 00:34:54.639
We talked about the board level.
I think also applies to your team.
501
00:34:55.000 --> 00:35:00.199
And even at present day works were
very transparent as a opening about how we're
502
00:35:00.239 --> 00:35:05.800
doing and where we're going. And
and you know, I explained to folks.
503
00:35:05.880 --> 00:35:07.880
Now I had a history with a
lot of these early folks, so
504
00:35:07.960 --> 00:35:13.199
they knew me from prior life and
and know that you know I'm not sugarcoating
505
00:35:13.199 --> 00:35:15.760
when I'm delivering to you like this
is okay, this is pretty dicey,
506
00:35:15.760 --> 00:35:17.559
it may not work. You know
what's going to happen. Um. So
507
00:35:17.679 --> 00:35:22.320
I think that transparency. But I
also think you can't lose sight, as
508
00:35:22.760 --> 00:35:27.079
the senior executives, that you have
to be able to tell a story like
509
00:35:27.159 --> 00:35:30.039
that, this is why it's happening, you know, this is what you
510
00:35:30.119 --> 00:35:31.960
know, to give some explanation for
it and explain what you're doing to try
511
00:35:32.039 --> 00:35:37.199
to fix it or make it better
and and what you're doing so and getting
512
00:35:37.239 --> 00:35:39.719
the team bought in. That,
I mean, that's in a lot of
513
00:35:39.800 --> 00:35:43.280
cases, that's what sustained me.
You know, I saw the team members,
514
00:35:43.440 --> 00:35:45.920
I saw some of the early customers
that we were getting success with,
515
00:35:45.800 --> 00:35:49.360
you know, using the product and
keeping with it. We still have our
516
00:35:49.559 --> 00:35:52.639
very first customer is still a customer
uh. So it kind of highlights,
517
00:35:52.719 --> 00:35:55.400
you know, some of the value
that we got there early on. So
518
00:35:55.480 --> 00:35:59.960
there wasn't that, there was no
you know, if you're getting no response,
519
00:36:00.639 --> 00:36:04.480
that's a different thing that you're getting
somewhat of a response and you just
520
00:36:04.639 --> 00:36:07.639
think that the market is not really
there. And that's probably what sustained me.
521
00:36:07.039 --> 00:36:10.599
I believe that we were getting a
response, the market just hadn't quite
522
00:36:10.639 --> 00:36:15.960
come into its own and and that
if we could just be persistent and patient,
523
00:36:15.079 --> 00:36:17.400
that this is going to pay off
in a big way. And obviously,
524
00:36:17.440 --> 00:36:21.400
with hindsight now we look like geniuses. But it would have been a
525
00:36:21.440 --> 00:36:22.599
hard time to tell you that that
I knew for sure that was going to
526
00:36:22.679 --> 00:36:25.920
happen, but that was my that
was my best assumption. And you know,
527
00:36:27.039 --> 00:36:31.800
going back to kind of the two
hundred plus rejections and those two fundraising
528
00:36:31.880 --> 00:36:36.440
grounds, like, do you feel
like there's something you would have done differently
529
00:36:36.519 --> 00:36:42.719
in hindsight? I think the positioning
of the company. I over emphasized the
530
00:36:43.000 --> 00:36:46.840
delivered as a service Um and where
I think that the venture community in general
531
00:36:46.920 --> 00:36:51.199
wants to see a product and I
think we could have probably emphasized that much
532
00:36:51.239 --> 00:36:53.039
better, especially in the B two
round or we could have made it much
533
00:36:53.079 --> 00:36:57.840
more of the technology and the portfolio, and I think we ended up making
534
00:36:57.920 --> 00:37:00.760
mistakes there that created the overhang that
John highlining. So then we did fix
535
00:37:00.840 --> 00:37:04.039
that as we went into the C
and the D, but it's too late,
536
00:37:04.360 --> 00:37:07.159
like they have a view of it, but now kind of taint what
537
00:37:07.239 --> 00:37:12.119
you're doing and so that that becomes
there. God. So I think this
538
00:37:12.239 --> 00:37:15.679
goes back to you of your comment
that people are not trying to get to
539
00:37:15.800 --> 00:37:19.800
the root of your story. They're
kind of reacting to the first five,
540
00:37:19.960 --> 00:37:23.039
fifteen seconds. So you have to
be very careful what you lead with.
541
00:37:24.239 --> 00:37:29.079
Moving on a little bit to kind
of the board situation, like how how
542
00:37:29.159 --> 00:37:34.519
you're communicating to the team, how
you are handling your board. I'm curious,
543
00:37:34.599 --> 00:37:37.599
John, like do you have advice
for other founders based on like what
544
00:37:37.960 --> 00:37:43.679
was your best experience with Brian?
What would you like other founders who are
545
00:37:43.760 --> 00:37:47.000
going through hard times in terms of
scaling their company, like, what is
546
00:37:47.079 --> 00:37:51.760
it that you need to see to
give you that conviction that you had with
547
00:37:51.880 --> 00:37:54.559
Brian? Well, I think,
I think when things aren't going well,
548
00:37:54.880 --> 00:38:01.360
which in every startup there's a time
when that's the case, as an investor,
549
00:38:02.000 --> 00:38:06.960
you want to be helpful and you
know one of the few few benefits
550
00:38:07.039 --> 00:38:09.920
you can bring is your perspective,
the reality that you've seen a lot of
551
00:38:09.960 --> 00:38:17.000
companies go through their ups and downs
and the truth is you know things are
552
00:38:17.079 --> 00:38:24.440
probably not all going right. So
if the CEO is isn't telling you that
553
00:38:24.559 --> 00:38:30.360
things aren't going right, they either
don't know or they're not telling you on
554
00:38:30.480 --> 00:38:36.639
purpose, and neither is good,
right. And so in this case,
555
00:38:36.719 --> 00:38:40.400
Brian was always very open about the
things he was trying in, what wasn't
556
00:38:40.440 --> 00:38:45.079
working and what was, and that
allowed us to work together on how to
557
00:38:45.159 --> 00:38:51.400
solve these things. Um, you
know, I I never lost belief in
558
00:38:51.519 --> 00:38:53.920
Brian and sometimes I think investors fool
themselves. They think they add value in
559
00:38:53.960 --> 00:38:58.679
all these ways, but I actually
think the single most important thing an investor
560
00:38:58.760 --> 00:39:02.599
can do is continue to give that
founder a sense of belief in them right,
561
00:39:02.760 --> 00:39:07.639
that we're going to get through it. And and for me, you
562
00:39:07.679 --> 00:39:09.880
know, that was that was a
lot easier with Brian because of just how
563
00:39:10.000 --> 00:39:15.639
he handled you know, the openness
right in terms of hey, this isn't
564
00:39:15.679 --> 00:39:19.960
working, this is working. He
always kept US informed, he treated us
565
00:39:20.440 --> 00:39:23.679
like partners in this and Um,
I think that made a huge difference.
566
00:39:23.840 --> 00:39:27.760
So if I had to give any
advice, it would just be you know
567
00:39:27.840 --> 00:39:32.719
that it's it's really along those lines. Treat treat your investors truly like partners,
568
00:39:32.960 --> 00:39:37.280
and the good ones they understand that
there's going to be ups and downs,
569
00:39:37.400 --> 00:39:39.960
but if you want them to help, they need to know what's going,
570
00:39:40.320 --> 00:39:45.360
what's going sideways or wrong, so
that they can the thing I'd add
571
00:39:45.400 --> 00:39:51.119
to the openness is not simply just
speeling raw data. It's your board members.
572
00:39:51.920 --> 00:39:54.480
So you know, part of the
job is is you need to frame
573
00:39:54.559 --> 00:39:59.400
the problem and understand it and and
put it in a way that that they
574
00:40:00.079 --> 00:40:04.639
members, can add value and what
you're doing. And so I like to
575
00:40:04.719 --> 00:40:07.840
talk about like I like to bring
challenges to the board when I think I
576
00:40:07.960 --> 00:40:12.760
have what are the different potential answers
to it, but I haven't made up
577
00:40:12.760 --> 00:40:15.000
my mind yet. So it's that's
it's a little bit of an art form.
578
00:40:15.079 --> 00:40:17.119
So if you get too far down
theline, you've already made up your
579
00:40:17.159 --> 00:40:20.480
mind, then when you bring it
to the board and they disagree with you,
580
00:40:20.559 --> 00:40:22.679
and now what do you do?
But if you bring it to the
581
00:40:22.719 --> 00:40:25.320
board when you can frame the problem. Uh, you know, it's a
582
00:40:25.400 --> 00:40:29.599
mistake for an entrepreneur, I think, to go to the board and have
583
00:40:29.960 --> 00:40:31.719
no idea what to do now.
If you're doing that, basically you're saying
584
00:40:31.760 --> 00:40:35.039
you give up. Uh, you
know, what should I do now?
585
00:40:35.320 --> 00:40:37.960
That doesn't mean you can't go to
some of your investors and you just need
586
00:40:38.000 --> 00:40:40.519
a bit of a pep talk,
like and you can do that. Just
587
00:40:40.679 --> 00:40:44.039
ask say hey, I'm really struggling
right now. Give me a little bit
588
00:40:44.039 --> 00:40:46.320
of a pep talk, and I've
done that before with with board members.
589
00:40:46.400 --> 00:40:49.199
I'm like, I don't even want
to tell you about anything, I just
590
00:40:49.239 --> 00:40:51.199
need a little bit of a pep
talk. Tell me how good I am,
591
00:40:51.280 --> 00:40:52.920
you know, give me some confidence
and what we're doing. But I
592
00:40:53.400 --> 00:40:59.480
I spend a lot of energy and
also just making clear that you know,
593
00:40:59.639 --> 00:41:04.320
by focusing on the process and showing
the measurements, showing the data associated that
594
00:41:04.440 --> 00:41:07.360
process, can't guarantee the outcome,
but I can show you all the work
595
00:41:07.400 --> 00:41:09.639
we're doing in the process and what
we've learned along the way, and you
596
00:41:09.719 --> 00:41:14.199
can have ideas and we're open to
whatever you want to do. So all
597
00:41:14.440 --> 00:41:16.400
those things, I think, are
part of it. So openness is not
598
00:41:17.519 --> 00:41:21.760
it doesn't forgive you not being prepared, not doing the work, not not
599
00:41:21.960 --> 00:41:25.320
getting ready. It's those things as
critical for someone understand, because I think
600
00:41:25.320 --> 00:41:29.599
sometimes someone confuses that. It's like
I'm just gonna dump to you my last
601
00:41:29.679 --> 00:41:31.440
meeting and how that felt. Okay, now, that's not that's not value.
602
00:41:31.800 --> 00:41:36.559
Like frame it help it put in
a form that people can understand and
603
00:41:36.719 --> 00:41:37.599
have a plan. Right, Brian, I mean I would say that you,
604
00:41:38.320 --> 00:41:42.400
despite the problems, you always had
a suggestion or a plan that you
605
00:41:42.480 --> 00:41:46.199
wanted feedback on, as opposed to
just venting. Um. One other thing.
606
00:41:46.239 --> 00:41:49.719
I'm conscious at times on you,
but I also wanted to say that
607
00:41:50.000 --> 00:41:53.280
I would often bring Brian my problems. You know, sometimes it's nice to
608
00:41:53.280 --> 00:41:57.199
think about other people's problems. Is
just a little bit of a restment and
609
00:41:57.440 --> 00:42:00.199
and so I always valued, you
know, an opportunity to kind say,
610
00:42:00.199 --> 00:42:01.519
Hey, Brian and these other companies
are struggling with these things. What do
611
00:42:01.639 --> 00:42:05.920
you think? And Uh, anyway, it just it made it more of
612
00:42:05.960 --> 00:42:09.400
a two way dynamic. I have
a story, not from Arctic wealth,
613
00:42:09.440 --> 00:42:15.559
but from two companies ago. Uh, a venture investor. Um, I
614
00:42:15.599 --> 00:42:20.199
should probably give him credit because I
quote him all the time to other entrepreneurs
615
00:42:20.239 --> 00:42:22.239
that come to me. John Fiber, who booked more, David Ow,
616
00:42:22.320 --> 00:42:29.199
he's now retired, and we this
not the not blue coat, but the
617
00:42:29.280 --> 00:42:31.679
company before that wasn't really playing out
the same sort of thing. And so
618
00:42:31.760 --> 00:42:35.639
we had a board meeting. OPTION
TO A, B and C. Nobody
619
00:42:35.679 --> 00:42:37.800
wanted to see. It was clear
the board wanted to be and the management
620
00:42:37.800 --> 00:42:42.840
team one to day in this conversation
and you know, after a while you
621
00:42:42.880 --> 00:42:45.440
realize you're talking in circles. So
we said that. I called a break.
622
00:42:45.719 --> 00:42:47.679
I go walking down the hall with
John And he looks at me and
623
00:42:47.719 --> 00:42:51.559
said I just want to be clear
that if you choose option a and it
624
00:42:51.599 --> 00:42:53.360
doesn't work out, you're gonna get
fired. And first time, CEO,
625
00:42:53.400 --> 00:42:55.559
it was a little bit taken aback. You know, what am I gonna
626
00:42:55.599 --> 00:42:59.920
do? Uh, and he goes
and then he you know, little dramatic
627
00:43:00.000 --> 00:43:01.920
pause and he goes. But if
you choose, you know, option being
628
00:43:01.920 --> 00:43:05.639
it doesn't work out, YOU'RE gonna
get fired anyway. And his basic point,
629
00:43:05.719 --> 00:43:07.440
and I think this is something I
tell entrepreneurs all the time, is
630
00:43:08.800 --> 00:43:13.559
you know, because it's your industry, it's Your Business and what you're doing.
631
00:43:13.760 --> 00:43:15.920
You've got to be willing to get
fired, and I'm not saying you
632
00:43:15.960 --> 00:43:17.440
got to behave in a bad way, but you've got to be willing to
633
00:43:17.519 --> 00:43:22.800
stand by your convictions and and present
the case, uh, and do it.
634
00:43:22.920 --> 00:43:25.880
And I you know there's I had
another situation with a very well known
635
00:43:27.679 --> 00:43:30.519
persona in the industry that was on
my board and they had presented a plan
636
00:43:30.639 --> 00:43:35.599
for me that I categorically disagreed with
and I said no, I'm not going
637
00:43:35.679 --> 00:43:37.440
to do that and they ultimately resigned
from the board. It was a bit
638
00:43:37.480 --> 00:43:42.400
of a hit for us, but
those are all kind of that developing that
639
00:43:42.559 --> 00:43:45.440
inner strength and the conviction and your
thoughts, being open minded. But you're
640
00:43:45.440 --> 00:43:51.360
still the CEO, like like you
know, and even if the board tells
641
00:43:51.400 --> 00:43:53.280
you to do accident doesn't work out, that's still going to be your fault
642
00:43:53.280 --> 00:43:57.000
as the CEO. So it's you
know, I'd leave you with that advice,
643
00:43:57.079 --> 00:44:00.800
which is listen, but it's still
your call and you need to live
644
00:44:00.840 --> 00:44:06.599
by it. Awesome. Well,
on those awesome words of advice, we'll
645
00:44:06.719 --> 00:44:09.840
wrap this episode up. Thank you
so much for spending time with us,
646
00:44:09.960 --> 00:44:14.440
Brian, and it was really lovely
to see you. Know you and John,
647
00:44:14.679 --> 00:44:19.440
like h take take time to kind
of share all these learnings from ten
648
00:44:19.559 --> 00:44:25.760
years of of of this relationship navigating, you know, the extreme rocket ship
649
00:44:25.960 --> 00:44:32.760
journey of opticalwth networks. It was
a real joy learning about it from both
650
00:44:32.800 --> 00:44:36.159
of you. Thank you so much. Thank you. Thanks. Ada.
651
00:44:44.400 --> 00:44:49.440
You've been listening to the startup field
guide with some here an unusual ventures podcast.
652
00:44:49.920 --> 00:44:53.239
Stay connected with us by subscribing to
the show in your favorite podcast player.
653
00:44:53.719 --> 00:44:58.320
If you like what you heard,
please rate our show and help us
654
00:44:58.400 --> 00:45:01.920
reach more aspiring found earth with lessons
on how to find product market fare.
655
00:45:02.519 --> 00:45:08.920
Thanks for listening. Until next time, H