April 29, 2026
Ep 20 - Ross Keating - Co-Founder of Overpath
In this episode of the Founders & Funding Podcast, Philip Smith speaks with Ross Keating, Co-Founder of Overpath.
Ross shares the story behind Overpath, an AI-powered revenue execution platform built to help sales reps work smarter without switching between tools. He talks about raising a VC-led pre-seed round, why speed of execution matters more than ever in AI, and what it really takes to build a founding team that investors will back. They also discuss the difference between bootstrapping and venture funding, and why distribution might be the most important thing an early-stage startup can build.
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Hi, welcome to the Founders and
Funding podcast.
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I'm your host, Philip Smith.
On the podcast, I'll be
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interviewing founders,
investors, startup advisors on
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how to fund the journey of your
startup and some tips and advice
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they have for you along the way.
This podcast is sponsored by
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Perfect Technologies and Laden.
Enjoy the episode.
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Ross, welcome to the Founders
and Funding podcast.
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Thanks.
For having me, Philip.
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Well, it's my pleasure to have
you.
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Just to start us off just for
the listeners.
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You've got a very nice
background of New York there.
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I do.
I'm based in Dublin, but I'm in
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New York for the week.
My wife is over here on work
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rotation at work at the moment.
So over here for the week and
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then back again in a few weeks
time.
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It's a nice opportunity for me
as well to meet some of our
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design partners and to meet some
VCs that view tours are around
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later this year.
Fantastic.
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I thought it was a green screen.
And then, you know, I was, I was
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astonished to see you really,
really are there in New York at
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the moment.
So that's great.
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Yeah, for sure.
And the sun is shining.
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It wasn't over the weekend, so
good opportunity to look at the
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skyline.
Absolutely.
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To start us off, Ross, tell me a
bit about your company and your
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role.
Yeah, sure.
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So I am the Co founder of
Overpath.
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So in Overpath we are building
AI agents for every member of a
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revenue team.
We're building in a new category
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which we're calling revenue
execution.
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And what Overpack does is it
connects if you're a Rep and
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Overpack connects to all of the
channels in which you work.
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So that's your e-mail, your
calendar, your call recording,
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your, your CRM.
And we build this context layer
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on which the agents can live.
So that means the agents can do
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some productivity tasks like
move your deals along in the CRM
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or write your follow up e-mail
or help you prepare for a call.
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But they can also then give you
performance feedback.
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So that could be in advance of a
call, it could be after a call.
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And they are not just reactive,
but they are also proactive.
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So it means because they
understand dynamically the data
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on which you're or you're
working, they can proactively
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intervene in a deal or they can
proactively guide you through
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the the work that you're doing.
What were, what were we?
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The behaviour in the market that
we're looking to capture is
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essentially every Rep is doing
at the moment.
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And that's working with
foundational models like Claude
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and Chachi, BT and and Gemini,
which are fantastic models as we
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all know, but they are not
purpose built for sales and you
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know bring some challenges with
them when you go to integrate
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them at an enterprise level
within sales organizations.
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Fantastic.
I really like that because it's,
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it's, it's, it's fantastic and
innovation and you know, it's,
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it's captured that kind of the,
the, the AI flow and and
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innovation that's happening.
But because our eye driven, I
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think that's really attractive
to companies is that it's it's
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driving that bottom line, which
is that what they're really
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trying to achieve from all the
different tools that they're
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using sounds like it's cutting
through the noise and actually
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getting them to where they want
to be.
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Yeah, I think that's a really
important point.
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You know, the go to market tech
stack that built over the last
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1520 years, it's obviously a
very mature tech stack, but it
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requires reps to context switch
between tools, right?
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So I log into my CRM and then
maybe I go to my revenue
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intelligence tool or maybe I go
to my sales automation tool.
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Maybe I've got a data provider.
And at the same time, we're
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doing a lot of my work in e-mail
or in Slack or over the phone or
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in person.
So the idea with Overpass is
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that we create this AI layer
where I can continue to work
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wherever I choose to work,
right?
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So at the moment we, I do my own
work now in, in Slack, right?
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And our, our first agent, Molly
is live in Slack.
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So I do all of my sales
activities now, pre call, post
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call, deal management, planning
my week from from from within
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that environment.
Fantastic.
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And what does an average day
look like right now?
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An average day right now is, is
scrappy and can change a lot
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given exactly where we are.
So we raised money back in
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December.
So we have been building a team
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and building a product and
starting to build distribution
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since January.
So we're, you know, 3 1/2 four
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months into that.
So my my focus at the moment
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kind of encompasses a number of
of things.
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One of those things is, you
know, using the product.
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So we have a couple of design
partners using it and we're
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using it internally ourselves.
And a lot of what I do is about
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creating fast feedback loops so
that we can get the product not
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only to a point where it is
usable, but where it is driving
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value.
And then secondly, we are
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thinking about distribution very
early, right.
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So we started a video first
content strategy back in
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January.
The 1st hire, that first hire in
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the commercial side that we
brought in Michael Paul, who you
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know is a is a content creator.
He's a, he's a video editor,
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which is probably not a typical
way that a an early stage start
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up goes to market.
But it's really, you know,
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thinking hard about the fact
that technology is getting
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easier and easier to build.
We know that we're building in a
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very crowded space.
So we really believe that, you
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know, building distribution and
building brand earlier than
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typical for a start of our size
is is more important than than
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ever.
So it's a lot of content
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creation and then it's a lot of
outreach, you know, starting to
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build our go to market flywheel,
starting to engage with new
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design partners and you know,
starting to think about how we
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scale our commercial org.
Fantastic.
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Yeah.
Well, look, I think you're
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thinking about it and, and doing
it the right way.
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I think a lot of companies they,
they don't really ever get that
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kind of, we call it kind of
creation, but we're just trying
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to speak to people in a in a, in
a way that they understand that
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that's engaging and that solves
their problems and speaks to the
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solution.
So I think to get that right, I
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think everything else will flow
from there really well.
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And how has the company funded
its journey to date?
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So we did proceeds fundraise
back in December.
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So it was a VC LED round.
So it was led by Elkstone with
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participation from Sure Valley
11 Angel.
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So we raised 1.6 or just over
1.6.
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So it gives us about 18 months
runway, 1820 months runway.
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And you know, it's really
designed for us to build a team,
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to build a prototype to take the
product to market to, to get to
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revenue with a view towards a
seed or or Series A, you know,
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at some point early mid next
year.
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Fantastic.
And what is the best way to fund
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a startup strength in your
opinion?
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You know, I think there's a
there's a danger of, you know,
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falling into a glamour trap
here, right?
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As you know, it's the it's the
VC funded startups that get the
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the the PR in the business.
Post big headlines, yeah.
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Exactly.
But really I think the, the best
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way to, to fund the startup is
dependent on the kind of
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business that you're building.
And you know what that business
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model looks like.
I mean, for example, I have
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another business, the Lenox
Academy, which is a, a services
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business.
It's a, it's a training business
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running for about 3 years.
And you know, that's a very lean
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operation.
It doesn't have engineering
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costs, it doesn't have nobody
marketing costs at the moment.
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Uh, you know, we, we run it, we
run a very lean, lean structure
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there.
So, uh, that was one which, you
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know, has we've been able to run
as a profitable business from
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the start.
It didn't, didn't need capital.
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Umm, and then on the over part
side, obviously, you know,
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there's a, there's a few few
elements to this, but one is
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that because we're, we're
building a team fast, we've got
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R&D costs, we've got
infrastructure costs and we are
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building this business with the
goal of an exponential outcome,
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right, which aligns with venture
capital expectations.
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So it made sense for us to go
out and to do, you know, a
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relatively large precede round.
There's, there's probably a,
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there's a happy medium in the
middle there, right, which
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startups take as well, which is
to do a private round early and
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to go out and really test the
market.
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So I think the best way to fund
the startup aligns with what
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your, your goals are for the
business and what the business
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model needs.
And another mistake that
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startups fall fall into is going
out to market to raise money
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without a real understanding of
what they need the money for or
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without the understanding of how
much they need and, and why they
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need it.
And you know, it's a big, big
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red flag to to AVC or to any
experienced Angel investor as
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well.
Yeah, I've had a few of those
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conversations with, with
founders who, you know, they're
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very eager to get VC funding or
do a proceed, but they kind of
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jump in between what, how much
they should actually, uh, raise
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or, or the rationale for it.
I think it's, you've got really,
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I think valuable and unique
experience there to have both
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bootstrapping business and to
have, you know, raised, uh,
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funding.
So I think it's, uh, it's, it's,
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it's a good journey to have both
experiences, but like there are
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pros and cons to, to, to both.
I think bootstrapping can be
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fantastic if if you can do it.
But I think sometimes, like with
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overpath, this speed is
important because I think with a
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lot of these companies, AI is
moving so fast that if you took
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the time to bootstrap, you might
not have years to just grind
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away at that.
You do need that that speed to
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capture the market before it
moves on.
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You're spot on there.
A big parts of the message when
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we went out to raise was about
speed of execution.
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It was a reason we didn't do an
Angel around early and went
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straight down to the VC route
because, you know, we're
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building in a, in a category
that is a new category, but it's
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one that's forming very quickly
and there's, you know,
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competitors emerging all the
time.
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So this is about how do we build
product fast?
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How do we get to market fast?
How do we build brand fast?
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How do we get a create usage
and, and get a user base
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quickly?
So the speed of execution is, is
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definitely a big factor here,
which also was a, as you say,
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you know, it was a, it was a key
reason to go about fundraising,
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to go back to looking for, to
for venture funding.
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Yeah, yeah, 100%.
It's, it's just, it's just every
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time I talk to a set up now,
there is just that before things
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are moving fast, but things move
at a whole new speed now with AI
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that there really isn't that
much.
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There's a lot more uncertainty
about the future now or like
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what's going to be where is AI
going to be in a year and how
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our companies then operate or
create new startups and how fast
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will it move.
So I think the safest bet now
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and before before maybe it
seemed risky to to raise money,
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move fasting that action now is
probably the the safest journey
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to go uncertainty and to look at
the founding team then a bit as
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well.
Ross, I suppose this is again
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one of those kind of a you know,
broad strong questions.
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But what?
What are the best skills new
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founders should possess?
Yeah so firstly I'm I'm lucky to
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have a fantastic Co founder
German O'Connor uh who has built
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and exited 2 software businesses
already.
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So he built box ever and skill
Co as well.
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So a part of us coming together
as a team, I suppose, was how do
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we combine or how do we create
complementary skill sets, you
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know, that we believe would be
successful for for this
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business.
And so obviously he has the
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experience of scaling and
organizations, gaining a
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technology organization and
going through that deep
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trajectory that a venture backed
company requires.
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And he's also got a technical
background, so he's that he's
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able to to fulfill that.
The technical conversation with
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the product team and the product
conversation with the product
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team.
Yeah, which I wouldn't have been
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able to do, right.
And then on my side, I suppose
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having spent the last three
years building Lennox, you know,
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spent a lot of time with sales
leaders and sales reps
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understanding what the market
dynamics look like, what the
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skills are that are required in
order to be a successful Rep, or
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what the mechanics are in order
to roll out methodology across
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the sales organization.
So I suppose there's a domain
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knowledge there.
And I think maybe as technology
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gets easier to build that
domain, understanding of what
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the problems that your user is
experiencing is more important
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than that than ever.
And similarly, I think as
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technology gets easier to build,
already mentioned this, but
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distribution is more important
than ever, right?
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So obviously I've, I've spent a
lot of time in building Linux,
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but I've also spent a lot of
time posting content on
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LinkedIn.
There's a smaller audience there
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now.
So there's a nice combination
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there hopefully between myself
and Dermot where he's got that,
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you know, kind of deep technical
products understanding.
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He's also done a, you know, he's
done multiple commercial roles
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and CEO roles as well, right?
So he has a commercial
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understanding too.
And then on my side, there's the
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there's the domain understanding
and maybe that the focus on
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distribution.
I think that's a great
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partnership to have.
I think it's always the case you
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can have that or you know, the
Kill funding team have all those
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scales.
But I think if you can, I think
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it complements each other
extremely well.
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If you can, if you can have that
and and to look then back at the
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investment piece, how can
companies attract investors
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effectively?
Yeah, I mean, look, I, I think
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there's a few pieces in this.
We we probably went about it a
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slightly unconventional route.
And so, you know, we went about
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a fundraise before we
incorporated a business or
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before we really had a product
German to spend time building a,
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a prototype.
We certainly didn't have any
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users.
I, I don't recommend that route.
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You know, we were in a, we were
in a strong position given maybe
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those complementary skill sets
or complementary backgrounds
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that I've described there.
So I think the best way that you
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can go about attracting
investment is to, you know, have
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a very strong point of view on
the world that you're that
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you're building for.
So you have a very strong thesis
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on what your industry or your
domain is going to look like in
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three, 5-10 years time to begin
building for that.
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And then really to get traction
right, I think, you know, you
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need proof points, you need
users actively using your
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products, you need customer
conversations.
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The biggest mistake that you can
make is, you know, building
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something in your head or
building something from the
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ideas in your head and not going
to get into the, to the hands
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of, of users, right?
That's something that we've
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tried to do very early, even
kind of post fundraisers.
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How do we get something into the
hands of users when it's really
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scrappy and has lots of hold on?
It doesn't work well, right.
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You know, there's a famous quote
out there that if you're not
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embarrassed by your first
product release, then you ship
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too late.
And you know that that's, it's
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a, it's a painful thing to do,
to sit in front of your users
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and to, to, to hear very tough
feedback about products that had
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bugs in them or features that
didn't exist yet.
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But it's a necessary 1.
And I think for most startups,
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you should do that before you go
out looking for, for money, or
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at least before you go out
looking for meaningful amounts
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of money in order to, to, to, to
scale.
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But then also the other thing is
that at a very early stage,
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really what what investors are
investing in are, are the
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00:16:15,400 --> 00:16:18,640
founders, right?
Yeah, there's only so much,
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00:16:19,440 --> 00:16:22,080
there's only so much information
that you can get about a very,
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very early stage.
There's only so much due
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00:16:23,560 --> 00:16:26,720
diligence that you can do right,
because it's, it's a very short
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lifespan the organizations had.
So really you're looking for
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00:16:31,880 --> 00:16:34,600
the, for the expertise of the
founders.
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You're looking for the vision of
the founders.
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You're looking for their ability
to execute, their ability to
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00:16:37,840 --> 00:16:43,120
hire talent as well, right?
Access to, to, to talent.
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00:16:43,640 --> 00:16:46,720
And so I think, you know, having
that thought process around what
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00:16:46,720 --> 00:16:49,200
your founding team looks like
is, is key, right?
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00:16:49,520 --> 00:16:53,000
If you can get a, a Co founder
with a complementary skill set,
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I would encourage you to do
that.
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I don't think I would ever build
a business solo again.
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But even if you can't get that
Co founder thinking about what
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is the profile of your founding
team, your founding engineering
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team, your founding commercial
team and showing that you have
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00:17:08,680 --> 00:17:13,240
the ability to you know, to to
to acquire that that that talent
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00:17:13,240 --> 00:17:15,800
in the in the business.
Yeah, absolutely.
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00:17:15,800 --> 00:17:18,400
Well, look, I think particularly
for your for yourselves in
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00:17:18,400 --> 00:17:20,960
Dermot, I think for investors,
it's, there's, there's a lot of
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00:17:20,960 --> 00:17:24,319
good rationale for why you would
be great founders to invest in
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00:17:24,319 --> 00:17:26,800
because you've had success, such
a success already.
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00:17:26,800 --> 00:17:29,800
But I think yes, certainly for
first time founders that do face
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00:17:29,800 --> 00:17:33,040
that struggle of why should I
invest in you as a person?
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00:17:33,040 --> 00:17:35,360
So I think trying to build that
credibility throughout your
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00:17:35,360 --> 00:17:39,480
career is something that that
might be needed before we
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00:17:39,480 --> 00:17:41,080
finish.
Ross, if you had one key piece
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00:17:41,080 --> 00:17:43,880
of advice to share on funding to
start up, what would it be?
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00:17:45,560 --> 00:17:48,640
So, but maybe we've touched on
some of this, but you know, it's
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00:17:48,640 --> 00:17:52,880
about having firstly, having a,
a clear objective on what you're
321
00:17:52,880 --> 00:17:55,720
trying to achieve in terms of
the size, why you need it,
322
00:17:55,840 --> 00:17:59,360
what's like what that is going
to do for you, you know, over,
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00:17:59,480 --> 00:18:01,120
over the next period of, of
time.
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00:18:01,120 --> 00:18:03,360
So, so planning exactly what you
need and finding the right
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00:18:03,360 --> 00:18:07,080
mechanism to fund your startup
is, is really important.
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00:18:07,120 --> 00:18:11,680
And then I think the best piece
of advice that I got was to run
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00:18:11,680 --> 00:18:14,880
your fundraising process like a
sales process, right?
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00:18:14,880 --> 00:18:19,760
So to run it like a Sprint.
So when you decide that you're
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00:18:19,760 --> 00:18:22,520
going out to market and you
know, you've built your data
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00:18:22,520 --> 00:18:24,680
room and you've built your deck
and you've built your financial
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00:18:24,680 --> 00:18:29,200
model that you then meet as many
investors that fit the profile
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00:18:30,080 --> 00:18:33,000
of investor that will fund your
startup in a short a time as as
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00:18:33,000 --> 00:18:35,440
possible.
You, you do that for a whole
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00:18:35,440 --> 00:18:38,680
bunch of reasons.
One, you know, you can create
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00:18:38,920 --> 00:18:43,080
competitive dynamics between
investors 2, you, you sharpen
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00:18:43,080 --> 00:18:48,000
your, your pitch very fast.
You get very fast feedback on,
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00:18:48,400 --> 00:18:52,960
you know, whether this is a, a
thesis that is, is landing with
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00:18:52,960 --> 00:18:59,160
investors, but also, you know,
you, you maximize, you maximize
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00:18:59,160 --> 00:19:02,480
your own time efficiency, right?
Like the worst thing that you
340
00:19:02,480 --> 00:19:05,200
can do is to go through an
elongated fundraising process
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00:19:05,200 --> 00:19:06,960
where you're trying to build a
business and then going back and
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00:19:06,960 --> 00:19:08,840
fundraising, going back to build
a business, right?
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00:19:09,240 --> 00:19:13,360
It's just, it's fundraising is
a, is a, is a, you know, it's an
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00:19:13,360 --> 00:19:17,040
all-encompassing thing.
So I think for anyone out there
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00:19:17,040 --> 00:19:19,440
that that that's listening and
is thinking about raising money,
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00:19:20,120 --> 00:19:22,480
build your thesis, get the right
materials together, get the
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00:19:22,480 --> 00:19:25,360
right team together, and then
meet as many investors as you
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00:19:25,360 --> 00:19:27,600
can in a, in a shorter time span
as you can.
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00:19:28,960 --> 00:19:31,080
Fantastic advice.
Ross, thanks so much for going
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00:19:31,080 --> 00:19:33,440
on the podcast.
It was really great speaking to
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00:19:33,440 --> 00:19:34,840
you.
Not at all.
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00:19:34,840 --> 00:19:37,000
Thanks for having.
Me a pleasure Ross.
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00:19:37,000 --> 00:19:39,800
Best of luck with Overpath and
I'll be watching you on LinkedIn
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00:19:39,800 --> 00:19:41,360
to see more.
Thanks, Philip.
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00:19:44,320 --> 00:19:47,360
Hi, thanks for listening to this
week's episode of the Founders
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00:19:47,360 --> 00:19:49,840
and Funding podcast.
If you'd like to be a guest or
357
00:19:49,840 --> 00:19:51,920
have a guest suggestion, please
get in touch.
358
00:19:52,600 --> 00:19:53,000
Thank you.
00:00:01,000 --> 00:00:03,480
Hi, welcome to the Founders and
Funding podcast.
2
00:00:03,480 --> 00:00:06,080
I'm your host, Philip Smith.
On the podcast, I'll be
3
00:00:06,080 --> 00:00:09,840
interviewing founders,
investors, startup advisors on
4
00:00:09,840 --> 00:00:13,520
how to fund the journey of your
startup and some tips and advice
5
00:00:13,520 --> 00:00:17,120
they have for you along the way.
This podcast is sponsored by
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00:00:17,120 --> 00:00:20,640
Perfect Technologies and Laden.
Enjoy the episode.
7
00:00:23,440 --> 00:00:25,720
Ross, welcome to the Founders
and Funding podcast.
8
00:00:25,720 --> 00:00:27,520
Thanks.
For having me, Philip.
9
00:00:28,760 --> 00:00:30,240
Well, it's my pleasure to have
you.
10
00:00:30,440 --> 00:00:32,080
Just to start us off just for
the listeners.
11
00:00:32,080 --> 00:00:34,960
You've got a very nice
background of New York there.
12
00:00:36,240 --> 00:00:38,000
I do.
I'm based in Dublin, but I'm in
13
00:00:38,000 --> 00:00:42,880
New York for the week.
My wife is over here on work
14
00:00:43,440 --> 00:00:46,480
rotation at work at the moment.
So over here for the week and
15
00:00:46,480 --> 00:00:47,840
then back again in a few weeks
time.
16
00:00:47,960 --> 00:00:50,400
It's a nice opportunity for me
as well to meet some of our
17
00:00:50,400 --> 00:00:55,440
design partners and to meet some
VCs that view tours are around
18
00:00:55,440 --> 00:00:57,320
later this year.
Fantastic.
19
00:00:57,320 --> 00:01:00,360
I thought it was a green screen.
And then, you know, I was, I was
20
00:01:00,360 --> 00:01:03,360
astonished to see you really,
really are there in New York at
21
00:01:03,360 --> 00:01:04,400
the moment.
So that's great.
22
00:01:05,720 --> 00:01:07,760
Yeah, for sure.
And the sun is shining.
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00:01:07,760 --> 00:01:10,600
It wasn't over the weekend, so
good opportunity to look at the
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00:01:10,600 --> 00:01:12,640
skyline.
Absolutely.
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00:01:13,080 --> 00:01:16,600
To start us off, Ross, tell me a
bit about your company and your
26
00:01:16,600 --> 00:01:18,880
role.
Yeah, sure.
27
00:01:18,880 --> 00:01:21,440
So I am the Co founder of
Overpath.
28
00:01:21,440 --> 00:01:27,160
So in Overpath we are building
AI agents for every member of a
29
00:01:27,400 --> 00:01:30,040
revenue team.
We're building in a new category
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00:01:30,040 --> 00:01:31,640
which we're calling revenue
execution.
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00:01:32,440 --> 00:01:35,760
And what Overpack does is it
connects if you're a Rep and
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00:01:35,760 --> 00:01:38,480
Overpack connects to all of the
channels in which you work.
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00:01:38,480 --> 00:01:42,040
So that's your e-mail, your
calendar, your call recording,
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00:01:42,040 --> 00:01:45,520
your, your CRM.
And we build this context layer
35
00:01:45,520 --> 00:01:49,360
on which the agents can live.
So that means the agents can do
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00:01:49,360 --> 00:01:54,200
some productivity tasks like
move your deals along in the CRM
37
00:01:54,200 --> 00:01:57,040
or write your follow up e-mail
or help you prepare for a call.
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00:01:57,400 --> 00:02:00,240
But they can also then give you
performance feedback.
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00:02:00,240 --> 00:02:03,200
So that could be in advance of a
call, it could be after a call.
40
00:02:04,000 --> 00:02:09,600
And they are not just reactive,
but they are also proactive.
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00:02:09,600 --> 00:02:13,080
So it means because they
understand dynamically the data
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00:02:13,880 --> 00:02:17,840
on which you're or you're
working, they can proactively
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00:02:17,840 --> 00:02:21,680
intervene in a deal or they can
proactively guide you through
44
00:02:21,680 --> 00:02:24,480
the the work that you're doing.
What were, what were we?
45
00:02:24,480 --> 00:02:27,720
The behaviour in the market that
we're looking to capture is
46
00:02:28,240 --> 00:02:29,880
essentially every Rep is doing
at the moment.
47
00:02:29,880 --> 00:02:32,200
And that's working with
foundational models like Claude
48
00:02:32,200 --> 00:02:37,440
and Chachi, BT and and Gemini,
which are fantastic models as we
49
00:02:37,440 --> 00:02:42,480
all know, but they are not
purpose built for sales and you
50
00:02:42,480 --> 00:02:45,480
know bring some challenges with
them when you go to integrate
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00:02:45,480 --> 00:02:48,120
them at an enterprise level
within sales organizations.
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00:02:49,760 --> 00:02:52,000
Fantastic.
I really like that because it's,
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00:02:52,000 --> 00:02:54,960
it's, it's, it's fantastic and
innovation and you know, it's,
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00:02:54,960 --> 00:02:59,160
it's captured that kind of the,
the, the AI flow and and
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00:02:59,200 --> 00:03:01,480
innovation that's happening.
But because our eye driven, I
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00:03:01,480 --> 00:03:03,960
think that's really attractive
to companies is that it's it's
57
00:03:04,040 --> 00:03:05,880
driving that bottom line, which
is that what they're really
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00:03:05,880 --> 00:03:09,120
trying to achieve from all the
different tools that they're
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00:03:09,120 --> 00:03:12,160
using sounds like it's cutting
through the noise and actually
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00:03:12,160 --> 00:03:13,840
getting them to where they want
to be.
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00:03:14,720 --> 00:03:16,920
Yeah, I think that's a really
important point.
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00:03:16,960 --> 00:03:20,960
You know, the go to market tech
stack that built over the last
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00:03:21,560 --> 00:03:25,240
1520 years, it's obviously a
very mature tech stack, but it
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00:03:25,240 --> 00:03:29,040
requires reps to context switch
between tools, right?
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00:03:29,040 --> 00:03:31,920
So I log into my CRM and then
maybe I go to my revenue
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00:03:31,920 --> 00:03:34,400
intelligence tool or maybe I go
to my sales automation tool.
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00:03:34,400 --> 00:03:36,920
Maybe I've got a data provider.
And at the same time, we're
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00:03:36,920 --> 00:03:41,880
doing a lot of my work in e-mail
or in Slack or over the phone or
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00:03:41,880 --> 00:03:44,520
in person.
So the idea with Overpass is
70
00:03:44,520 --> 00:03:48,120
that we create this AI layer
where I can continue to work
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00:03:48,120 --> 00:03:49,760
wherever I choose to work,
right?
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00:03:49,760 --> 00:03:54,120
So at the moment we, I do my own
work now in, in Slack, right?
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00:03:54,120 --> 00:03:57,760
And our, our first agent, Molly
is live in Slack.
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00:03:57,760 --> 00:04:00,880
So I do all of my sales
activities now, pre call, post
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00:04:00,880 --> 00:04:05,400
call, deal management, planning
my week from from from within
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00:04:05,400 --> 00:04:08,080
that environment.
Fantastic.
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00:04:08,360 --> 00:04:10,440
And what does an average day
look like right now?
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00:04:12,360 --> 00:04:17,519
An average day right now is, is
scrappy and can change a lot
79
00:04:17,519 --> 00:04:20,839
given exactly where we are.
So we raised money back in
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00:04:20,839 --> 00:04:24,080
December.
So we have been building a team
81
00:04:24,080 --> 00:04:26,920
and building a product and
starting to build distribution
82
00:04:26,920 --> 00:04:29,600
since January.
So we're, you know, 3 1/2 four
83
00:04:29,600 --> 00:04:33,000
months into that.
So my my focus at the moment
84
00:04:34,160 --> 00:04:36,120
kind of encompasses a number of
of things.
85
00:04:36,760 --> 00:04:40,360
One of those things is, you
know, using the product.
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00:04:40,360 --> 00:04:42,840
So we have a couple of design
partners using it and we're
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using it internally ourselves.
And a lot of what I do is about
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creating fast feedback loops so
that we can get the product not
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only to a point where it is
usable, but where it is driving
90
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value.
And then secondly, we are
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thinking about distribution very
early, right.
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So we started a video first
content strategy back in
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January.
The 1st hire, that first hire in
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the commercial side that we
brought in Michael Paul, who you
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know is a is a content creator.
He's a, he's a video editor,
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which is probably not a typical
way that a an early stage start
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up goes to market.
But it's really, you know,
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thinking hard about the fact
that technology is getting
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easier and easier to build.
We know that we're building in a
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very crowded space.
So we really believe that, you
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know, building distribution and
building brand earlier than
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typical for a start of our size
is is more important than than
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ever.
So it's a lot of content
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creation and then it's a lot of
outreach, you know, starting to
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build our go to market flywheel,
starting to engage with new
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design partners and you know,
starting to think about how we
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scale our commercial org.
Fantastic.
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Yeah.
Well, look, I think you're
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thinking about it and, and doing
it the right way.
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I think a lot of companies they,
they don't really ever get that
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kind of, we call it kind of
creation, but we're just trying
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to speak to people in a in a, in
a way that they understand that
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that's engaging and that solves
their problems and speaks to the
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solution.
So I think to get that right, I
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think everything else will flow
from there really well.
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And how has the company funded
its journey to date?
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So we did proceeds fundraise
back in December.
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So it was a VC LED round.
So it was led by Elkstone with
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participation from Sure Valley
11 Angel.
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So we raised 1.6 or just over
1.6.
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So it gives us about 18 months
runway, 1820 months runway.
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And you know, it's really
designed for us to build a team,
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to build a prototype to take the
product to market to, to get to
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revenue with a view towards a
seed or or Series A, you know,
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at some point early mid next
year.
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Fantastic.
And what is the best way to fund
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a startup strength in your
opinion?
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You know, I think there's a
there's a danger of, you know,
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falling into a glamour trap
here, right?
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As you know, it's the it's the
VC funded startups that get the
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the the PR in the business.
Post big headlines, yeah.
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Exactly.
But really I think the, the best
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way to, to fund the startup is
dependent on the kind of
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business that you're building.
And you know what that business
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model looks like.
I mean, for example, I have
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another business, the Lenox
Academy, which is a, a services
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business.
It's a, it's a training business
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running for about 3 years.
And you know, that's a very lean
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operation.
It doesn't have engineering
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costs, it doesn't have nobody
marketing costs at the moment.
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Uh, you know, we, we run it, we
run a very lean, lean structure
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there.
So, uh, that was one which, you
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know, has we've been able to run
as a profitable business from
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the start.
It didn't, didn't need capital.
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Umm, and then on the over part
side, obviously, you know,
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there's a, there's a few few
elements to this, but one is
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that because we're, we're
building a team fast, we've got
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R&D costs, we've got
infrastructure costs and we are
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building this business with the
goal of an exponential outcome,
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right, which aligns with venture
capital expectations.
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So it made sense for us to go
out and to do, you know, a
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relatively large precede round.
There's, there's probably a,
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there's a happy medium in the
middle there, right, which
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startups take as well, which is
to do a private round early and
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to go out and really test the
market.
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So I think the best way to fund
the startup aligns with what
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your, your goals are for the
business and what the business
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model needs.
And another mistake that
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startups fall fall into is going
out to market to raise money
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without a real understanding of
what they need the money for or
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without the understanding of how
much they need and, and why they
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need it.
And you know, it's a big, big
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red flag to to AVC or to any
experienced Angel investor as
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well.
Yeah, I've had a few of those
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conversations with, with
founders who, you know, they're
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very eager to get VC funding or
do a proceed, but they kind of
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00:09:18,720 --> 00:09:21,120
jump in between what, how much
they should actually, uh, raise
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or, or the rationale for it.
I think it's, you've got really,
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I think valuable and unique
experience there to have both
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bootstrapping business and to
have, you know, raised, uh,
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funding.
So I think it's, uh, it's, it's,
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it's a good journey to have both
experiences, but like there are
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pros and cons to, to, to both.
I think bootstrapping can be
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fantastic if if you can do it.
But I think sometimes, like with
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overpath, this speed is
important because I think with a
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lot of these companies, AI is
moving so fast that if you took
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the time to bootstrap, you might
not have years to just grind
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away at that.
You do need that that speed to
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capture the market before it
moves on.
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You're spot on there.
A big parts of the message when
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we went out to raise was about
speed of execution.
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It was a reason we didn't do an
Angel around early and went
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straight down to the VC route
because, you know, we're
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building in a, in a category
that is a new category, but it's
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one that's forming very quickly
and there's, you know,
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competitors emerging all the
time.
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So this is about how do we build
product fast?
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How do we get to market fast?
How do we build brand fast?
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How do we get a create usage
and, and get a user base
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quickly?
So the speed of execution is, is
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definitely a big factor here,
which also was a, as you say,
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you know, it was a, it was a key
reason to go about fundraising,
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to go back to looking for, to
for venture funding.
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Yeah, yeah, 100%.
It's, it's just, it's just every
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time I talk to a set up now,
there is just that before things
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are moving fast, but things move
at a whole new speed now with AI
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that there really isn't that
much.
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There's a lot more uncertainty
about the future now or like
199
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what's going to be where is AI
going to be in a year and how
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our companies then operate or
create new startups and how fast
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will it move.
So I think the safest bet now
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and before before maybe it
seemed risky to to raise money,
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move fasting that action now is
probably the the safest journey
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to go uncertainty and to look at
the founding team then a bit as
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well.
Ross, I suppose this is again
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one of those kind of a you know,
broad strong questions.
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But what?
What are the best skills new
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founders should possess?
Yeah so firstly I'm I'm lucky to
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have a fantastic Co founder
German O'Connor uh who has built
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and exited 2 software businesses
already.
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So he built box ever and skill
Co as well.
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So a part of us coming together
as a team, I suppose, was how do
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we combine or how do we create
complementary skill sets, you
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know, that we believe would be
successful for for this
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business.
And so obviously he has the
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experience of scaling and
organizations, gaining a
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technology organization and
going through that deep
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trajectory that a venture backed
company requires.
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And he's also got a technical
background, so he's that he's
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able to to fulfill that.
The technical conversation with
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the product team and the product
conversation with the product
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team.
Yeah, which I wouldn't have been
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able to do, right.
And then on my side, I suppose
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having spent the last three
years building Lennox, you know,
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spent a lot of time with sales
leaders and sales reps
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understanding what the market
dynamics look like, what the
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skills are that are required in
order to be a successful Rep, or
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what the mechanics are in order
to roll out methodology across
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the sales organization.
So I suppose there's a domain
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knowledge there.
And I think maybe as technology
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gets easier to build that
domain, understanding of what
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the problems that your user is
experiencing is more important
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than that than ever.
And similarly, I think as
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technology gets easier to build,
already mentioned this, but
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distribution is more important
than ever, right?
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So obviously I've, I've spent a
lot of time in building Linux,
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but I've also spent a lot of
time posting content on
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LinkedIn.
There's a smaller audience there
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now.
So there's a nice combination
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there hopefully between myself
and Dermot where he's got that,
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you know, kind of deep technical
products understanding.
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He's also done a, you know, he's
done multiple commercial roles
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and CEO roles as well, right?
So he has a commercial
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understanding too.
And then on my side, there's the
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there's the domain understanding
and maybe that the focus on
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distribution.
I think that's a great
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partnership to have.
I think it's always the case you
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can have that or you know, the
Kill funding team have all those
249
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scales.
But I think if you can, I think
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it complements each other
extremely well.
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If you can, if you can have that
and and to look then back at the
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investment piece, how can
companies attract investors
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effectively?
Yeah, I mean, look, I, I think
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there's a few pieces in this.
We we probably went about it a
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slightly unconventional route.
And so, you know, we went about
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a fundraise before we
incorporated a business or
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before we really had a product
German to spend time building a,
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a prototype.
We certainly didn't have any
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users.
I, I don't recommend that route.
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You know, we were in a, we were
in a strong position given maybe
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those complementary skill sets
or complementary backgrounds
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that I've described there.
So I think the best way that you
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can go about attracting
investment is to, you know, have
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a very strong point of view on
the world that you're that
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you're building for.
So you have a very strong thesis
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on what your industry or your
domain is going to look like in
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three, 5-10 years time to begin
building for that.
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And then really to get traction
right, I think, you know, you
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need proof points, you need
users actively using your
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products, you need customer
conversations.
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The biggest mistake that you can
make is, you know, building
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something in your head or
building something from the
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ideas in your head and not going
to get into the, to the hands
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of, of users, right?
That's something that we've
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tried to do very early, even
kind of post fundraisers.
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How do we get something into the
hands of users when it's really
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scrappy and has lots of hold on?
It doesn't work well, right.
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You know, there's a famous quote
out there that if you're not
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embarrassed by your first
product release, then you ship
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too late.
And you know that that's, it's
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a, it's a painful thing to do,
to sit in front of your users
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and to, to, to hear very tough
feedback about products that had
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bugs in them or features that
didn't exist yet.
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But it's a necessary 1.
And I think for most startups,
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you should do that before you go
out looking for, for money, or
286
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at least before you go out
looking for meaningful amounts
287
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of money in order to, to, to, to
scale.
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But then also the other thing is
that at a very early stage,
289
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really what what investors are
investing in are, are the
290
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founders, right?
Yeah, there's only so much,
291
00:16:19,440 --> 00:16:22,080
there's only so much information
that you can get about a very,
292
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very early stage.
There's only so much due
293
00:16:23,560 --> 00:16:26,720
diligence that you can do right,
because it's, it's a very short
294
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lifespan the organizations had.
So really you're looking for
295
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the, for the expertise of the
founders.
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You're looking for the vision of
the founders.
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You're looking for their ability
to execute, their ability to
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hire talent as well, right?
Access to, to, to talent.
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And so I think, you know, having
that thought process around what
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your founding team looks like
is, is key, right?
301
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If you can get a, a Co founder
with a complementary skill set,
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I would encourage you to do
that.
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I don't think I would ever build
a business solo again.
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But even if you can't get that
Co founder thinking about what
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is the profile of your founding
team, your founding engineering
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team, your founding commercial
team and showing that you have
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the ability to you know, to to
to acquire that that that talent
308
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in the in the business.
Yeah, absolutely.
309
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Well, look, I think particularly
for your for yourselves in
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Dermot, I think for investors,
it's, there's, there's a lot of
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good rationale for why you would
be great founders to invest in
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because you've had success, such
a success already.
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But I think yes, certainly for
first time founders that do face
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that struggle of why should I
invest in you as a person?
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So I think trying to build that
credibility throughout your
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career is something that that
might be needed before we
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finish.
Ross, if you had one key piece
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of advice to share on funding to
start up, what would it be?
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So, but maybe we've touched on
some of this, but you know, it's
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about having firstly, having a,
a clear objective on what you're
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trying to achieve in terms of
the size, why you need it,
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what's like what that is going
to do for you, you know, over,
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over the next period of, of
time.
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So, so planning exactly what you
need and finding the right
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mechanism to fund your startup
is, is really important.
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And then I think the best piece
of advice that I got was to run
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your fundraising process like a
sales process, right?
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So to run it like a Sprint.
So when you decide that you're
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going out to market and you
know, you've built your data
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room and you've built your deck
and you've built your financial
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model that you then meet as many
investors that fit the profile
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of investor that will fund your
startup in a short a time as as
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possible.
You, you do that for a whole
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bunch of reasons.
One, you know, you can create
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competitive dynamics between
investors 2, you, you sharpen
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your, your pitch very fast.
You get very fast feedback on,
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you know, whether this is a, a
thesis that is, is landing with
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investors, but also, you know,
you, you maximize, you maximize
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your own time efficiency, right?
Like the worst thing that you
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can do is to go through an
elongated fundraising process
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where you're trying to build a
business and then going back and
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fundraising, going back to build
a business, right?
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It's just, it's fundraising is
a, is a, is a, you know, it's an
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all-encompassing thing.
So I think for anyone out there
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that that that's listening and
is thinking about raising money,
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build your thesis, get the right
materials together, get the
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right team together, and then
meet as many investors as you
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can in a, in a shorter time span
as you can.
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Fantastic advice.
Ross, thanks so much for going
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on the podcast.
It was really great speaking to
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you.
Not at all.
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Thanks for having.
Me a pleasure Ross.
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Best of luck with Overpath and
I'll be watching you on LinkedIn
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to see more.
Thanks, Philip.
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Hi, thanks for listening to this
week's episode of the Founders
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and Funding podcast.
If you'd like to be a guest or
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have a guest suggestion, please
get in touch.
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Thank you.