March 25, 2026

Ep 16 - Alister Esam - Angel Investor and Founder of Angel6

Ep 16 - Alister Esam - Angel Investor and Founder of Angel6

In this episode, Alister Esam shares with Philip what really drives successful startup investing, from spotting patterns across hundreds of deals to why traction matters more than ideas. We discuss founder traits, funding trade-offs, and the reality behind 10x returns and failed investments.

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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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Hi Alistair, welcome to the
Founders and Funding podcasts.

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Thank you, Philip.
Glad to be here.

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My pleasure to have you on to
set us off, Alistair.

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Talk to me about your company
and your role.

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So I'm not sure it's really a
company, but I'm a, I'm an

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exited SAS founder.
So I have my business with ball

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packs and we people used to turn
up to board meetings with big

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paperbacks and now they turn up
with iPads.

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And we were the guys that did
the tech around that.

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And I exited that in 2018.
And since then I've, I've sort

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of been investing all sorts of
things.

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I've tried everything on the
investing front, ended up with a

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couple of things that I think
work really, really well.

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One of them is kind of share
trading and the other one is

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startups.
And when I did that, I was quite

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surprised how naive the whole
industry is with regards to

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investing.
And it's a really, it's a really

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interesting area where it's not
you can argue isn't very

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efficient at all from an
investor point of view.

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So my first investment failed,
my next investment suddenly gets

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a 10X.
My third fails, my 4th gets a

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10X.
And I keep going because the 10X

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is making it worthwhile.
And I start to see a pattern

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really amongst these investments
that I'm making.

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And the failures get less and
less and the successors seem to

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come kind of more and more.
And now I'm, I'm kind of like

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reviewing hundreds of start-ups
every year and I'm picking the

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best 6.
And so I recently found this

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thing called Angel 6 where
investors can follow my track

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record, follow me, I will share
the investments at no cost with

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them and they can.
And that just helps helps me

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raise more money for the for the
startups I'm investing in, which

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is which is which which helps
them.

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Fantastic.
Well, that's some really great

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experience.
And I think a lot of investors,

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they probably envy, envy the 10
exports.

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Don't you know, they've had
plenty of losses themselves.

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It's very hard to pick and
choose.

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And what does an average day
look like right now?

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So are they typically start work
till about somewhere between

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10:00 and 11:00?
So if I'm at home, I might walk

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in the dog with my wife.
We'll go for a coffee every

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morning.
I'm kind of, I kind of decided

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I've slipped into this not
working very hard life and and

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the investment suits that.
So we're a lot of holidays.

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We've got a holiday home.
We'll go to a lot race cars.

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And so I have 50% of my time's
leisure.

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But when I'm not doing that, I
mean, really it's, it's talking

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to my start-ups, mentoring the
ones I mentor on the board of a

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few.
But a lot of my time is spent

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like sat on my desk.
And I love doing this, looking

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at whether it's the start-ups or
the share trading, just

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reviewing the investments and
working out where the

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opportunities are and trying to
apply an analytical approach to

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that, which not many people do.
So I mean, that's, that's it

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really.
I'm at my desk or I'm having

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fun.
Yeah, well, at that, to be

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honest, I think it's a it's a
good way to to be.

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But I'm very much pro kind of a
mixed lifestyle.

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I think some people can be too
rich with the 9:00 to 5:00.

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I think have your mornings or
your evenings and your weekends

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or even work weekends or take
Mondays off.

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Just I think once the routine I
think supports the the work.

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I think I'm a big believer in
that.

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And I think you've earned that
right to be able to have the

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freedom as well.
So kudos to you.

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My wife quite well illness, my
wife, my wife might argue with

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this, but I I like to claim that
my calendar, everything in my

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calendar, I can just change it
all and move it all and cancel

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it and postpone it because the
start-ups will wait.

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Investing will wait.
You know, nothing's nothing's

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urgent.
So if we want to have a week

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off, we can.
But she'll always say, oh, hang

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on, what about this?
But.

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I think that's, I think that's
the dream life for myself.

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I think that's the way to have
it and talk to me with some of

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these startups that you've
invested in.

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And why Alistair?
Yeah.

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So I've had some some great
startups over the years and most

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of them are still in.
So some some that are doing

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really, really well and
astonishingly well really, you

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know, 2020 times returns on on
all of them.

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So the, the ones that I'm
investing in at the moment, I

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think it seems to get better and
better because the ones I'm

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investing at the moment, I do
this thing where I score the

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startup a few months after I've
invested when the 1st update

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comes out.
Because when you're investing,

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you get very excited.
It's quite an interesting thing.

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As soon as you sign the cheque,
you go and you, I'm a very

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positive person, but you start
to look at, oh, did I make a

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mistake there?
And there's a few where I've

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gone, oh, oh, you know what?
I'm not sure.

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I think that was, I'm not, and I
don't realise it until the

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cheque goes out the door and you
think, oh, big mistake.

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And, and so the way I've started
to score them, it's really

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interesting.
Is that like a month after the

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update comes out, everything has
calmed down.

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You're now looking at it more
objectively.

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What do I, what do I, what do I
now think about that?

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I give them a confidence score
of 100 and that's getting better

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and better.
I mean, the, the three I've

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invested in most recently,
Health key is a, is a

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marketplace for health services.
There's Habitat Learn, which is

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an accessibility based ad tech
focused ad tech company that is

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hopefully kind of being going to
be driven forward by one of the

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IT phobal IT guerrillas.
And another one is your future,

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which is, is Gen.
Z entry level hiring platform

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with kind of a, an IP related
patterns on on kind of how they

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match or with some IP on how
they match kind of profiles to

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jobs.
We ask to competitive space that

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I've been wary about going into
it because there's loads of that

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stuff.
But these three, what excites me

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about them is they've come from
typically in essence of them has

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come from nowhere to something
very, very successful in a very

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short period of time.
They're not asking ridiculous

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valuations because they, they
kind of short track record

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because they've come from
nowhere and the growth rate is

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phenomenal.
And they're doing that growth

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typically without any sales
team.

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You know, this is they're just
about to, to raise to, to, to,

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to kind of accelerate.
So I mean, they, they, they get,

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they, they get really excited,
they're going to be really

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excited.
Fantastic.

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Well, it's, it's interesting.
I think there was a bit of I've

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always felt when you invested in
a startup, when you when you

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first learn about it, when you
know, it's that kind of new

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opportunity.
It's a bit like when you maybe

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you're the car dealership and
you know that he says someone

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else wants to buy the car to be
gone tomorrow.

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There's always a new fear that
window of opportunity will

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disappear, you know, But then
when you take a breath and you

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get home and you think,
actually, if I want to drive

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this scene and like, what's the
what's the mileage of the

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problems with it?
But I think there's some

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similarities there.
And then what is the best way to

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find a startup journey in your
opinion?

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Have you found, you know that
they're better if they they

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bootstrap or if they invest or
get loans or is there certain

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types of investments or or ways
to fund it that you appeal to

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you more?
But I mean, if I, if I, if I

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look at it from Michael, is he
as an investor?

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I like the ambitious ones that
are looking to raise, raise,

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raise, raise, raise, get really
big and grow.

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That's what I like because I
know that's where the money is

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as an investor, it's exciting
and you get amazing returns and

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you, you know, you that way
you're working towards an exit.

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I think it's interesting because
I met one of my, I met one of my

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investments the other day.
That's one of doing, you know, I

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think they're, they're kind of
onto series B now and they are

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the guy said to me, you know, do
you think because it's a

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question as to as a business
strategy, he was asking from a

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business strategy point of view,
do you think we should, you

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know, we should grow like like
massively take on money, just go

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for it?
Or do you think we should sort

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of remain a luxury product,
scale down and, you know, study

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off and get, get to profit and,
and all this sort of stuff?

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And, you know, from my point of
view, if, if you're just looking

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financially, the answer was
grow.

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But for, for the, for the actual
founders point of view, it, it

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depends what you want, because
taking on that money is risky.

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You know, quite often you, I've
had some horror stories where

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you know, the, the, the startup
has done OK, but the CEO got

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fired for underperformance.
And this is the founder of their

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business getting fired from
their own business.

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And, and you know, because
they've signed a deal with the

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VCs that that that allows that
to happen.

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And, and you know, they're
ending up with very, very little

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as a result because they decided
to go for it.

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So it's really, I think it's
really about what your appetite

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for risk is and what your, what
you know, what lifestyle you,

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you want as a founder.
So, so I think it's a difficult

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1, you know, and I think you
have to look at it from that

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personal viewpoint.
Yeah, I think that makes a lot

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of sense.
But look, it's only, it's only

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right that of course when you're
investing into a start up that

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you want to see that hunger for
them to to want to invest and to

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get investment and grow more.
But there is certainly some

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trade-offs and and it doesn't
work out every time.

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You know, it's kind of there's a
bit of a kind of if you look at

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just LinkedIn post, you might
think that everything was rosy

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all the time.
What kind of reality is, is

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certainly not that and to to
look at the founders themselves

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a bit, is there, is there
certain skills that you think

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Finer should possess or that
skills that they might have that

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would attract you to invest more
Alistair?

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It's, it's, I mean, this is kind
of, this is the crux of, I

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suppose my thesis and why I
think it works, which is that

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most angels look at the
investment and they guess 2

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questions.
They go, is the idea good?

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I think they do anyway, is the
idea good?

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So is it a good idea?
Does that work right?

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I, I'm, I'm, I'm crap at
deciding if it's these things

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are a good idea, right?
I think something's a good idea

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and it flops.
And then I think something else

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is stupid and it does amazingly
well.

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I think it's really, really a
skill that I don't know how many

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people have to judge that.
And the second is all the

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question you're asking is, you
know, do you look at the fan?

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Do you think they can do it?
And I just think they're

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terrible, terrible in the
generality.

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I think they're terrible ways to
assess.

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You know, I've got somewhere I
think and it doesn't come across

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as impressive, but I'm watching
the nail it day in, day out.

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And you know, it could be that
they've got a great sales team.

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Could be they've got something
else about them.

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And I just don't think that what
we, what we expect a founder to

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be is, is necessarily always the
right thing that they need to

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be.
So having said that, there are a

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few pass gates that I apply to,
to the founders.

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And one is these, these are
obvious really, but I need to

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trust them.
So there's an element of trust I

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have to build up.
So, you know, always, every,

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every investment.
I mean, I'm even for a coffee, I

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have a chat with them.
They need to be willing to

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listen.
We, you know, we obviously comes

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through on the first call
whether they are or not, you

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know, because if they're not
willing to listen to, to, to me

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and my suggestions, they're not
going to listen to anybody.

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And that's just that's the
recipe for disaster.

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And then there's there's a
combination of investors that I

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really think works really well.
And it's when you have two

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people found US1 is the kind of
out there salesperson that you

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know, can go and get business.
So if I look at that's, it's

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interesting when you, when I
could learn about your future,

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which is a recruitment business,
they obviously got recruiters

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working for them.
Recruiters are just sales mad

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people, all of them and say you
know that, you know that

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person's going to go out and get
the business.

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The second side of it is is the
dev side.

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And when it's a tech, because
everything I do is tech.

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And there was something Bill
Gates said, I think he said

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something along the lines of the
a great developer is 1010

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thousand.
I think you said times more

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effective than a good developer
because they're a media

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developer, because they get the
right architecture, they get the

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right structure, they go faster,
they're just they can just kind

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of handle more in their head.
And and so you know, you, you

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see that not necessarily when
you meet the developer, you see

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it in what they've built in what
in the time scale that they've

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built it.
And if you put those two things

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together, they're the two things
that I think that, you know, can

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swing it for me a little bit.
But I I what I really need to

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see is metrics on the.
Yeah.

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Well, the metrics are the the
biggest insight of all really.

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But that's an interesting point
you made there because I think,

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yeah, like I see a lot of
investors, they look for maybe,

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you know, maybe one sales guy,
one kind of tech product guy.

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But you know, you raised a good
point there that there's there's

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different ways that they can
they can be ineffective.

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Some finders might love with the
laptop which was working with

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terrible public speaking or vice
versa.

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But they can also implement,
they can have a augmented team

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of employees or freelancers they
got to help fix something.

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So I think there's it's
certainly there's room for all

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kinds of founders to succeed.
And how can companies themselves

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attract investors more
effectively?

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For me, everything's about the
metrics.

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So and when I tried it, like I
say, I looked through, do I

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think this is a good idea?
Because if someone's buying it,

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I don't do anything pre revenue.
I want to see, I want to see

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traction.
So if someone's buying it, who

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am I to say whether it's a good
idea or not?

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They they're the, they're the
customers and they obviously

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think it's a good idea.
So I need traction, I need a a

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big growth rate.
I want to see that growth rate

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and, and a scalable growth.
So the ones I'd like that I just

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mentioned, you know, they're,
they're doing that growth rate

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on, on the founder, doing so on
founder LED sales.

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So, you know, when that changes,
they should grow a lot faster.

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I want to see a market size from
a bottom up that, you know, not,

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not a top down.
This is £100 billion market.

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I want to see, you know, how
many clients can, how many

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clients can you sell this to?
How many clients are you likely

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to sell this to?
What are they going to pay?

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And you know, and does it
translate overseas and and a

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reasonable evaluation.
But I know, so that's what I

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want to see.
But I do think that I do think

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that that's not necessarily
that's might might not be the

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exact answer to your question
because, you know, other people

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want to see other things.
And I think if you do do an

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exciting picture, you put a
vision forward and, and you've

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got the idea at Angel level and
even at VC level, at Angel

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level, they people like that
good idea thing.

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I think you will get investment.
I see all the time and I'm

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amazed sometimes they're pre
revenue things with with £7

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million valuations that are just
easily getting the money because

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the people like the idea.
And then I think even at even at

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VC level, I think what people
like at BC level is the is, is a

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believe, they're to believe that
there is a massive market

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opportunity because they want
the big, they want the big

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prizes.
Sometimes I don't think that's

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necessarily sometimes I think
that where there's a, where

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there's a huge market, there's a
lot of competition and, and in

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a, and so there will be other
players.

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And then so big is good, but
huge isn't sort of 10 times

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better necessarily.
But I think VCs do like that.

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Yeah, I think that's a very good
insight.

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And if you'd one key piece of
advice to share and fund in the

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startup, what would it be?
In funding a startup, I think

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it's like, give you an example.
I mean, I had one of my own

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startups come back to me and
it's one, it's one of the ones

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that I've got to be careful what
I say is not going to give the

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name away, but it's one of the
ones that I probably, I'd

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probably after investing,
thought was that such a good

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idea?
And I, I think they will make

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it.
And I think they could be

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massive, but they, they are
struggling a little bit and they

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have got their, their, they came
to me with a, a new pitch deck

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saying we're raising again
because we, you know, we need to

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raise and we're raising at the
same valuation as as last time.

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And, and here's the story and
they showed me the story and it

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was just a fairy story.
It was basically if we, if we

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sell five times as much as we
have been selling, we'll be

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fine.
And it's going well.

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00:15:53,320 --> 00:15:55,720
Well, I don't know where you're
getting that from because how,

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how's that, how, how are you
going to do that?

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You're not explaining it.
It's just like you've literally,

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you've literally just put the
percentage growth figure in that

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gets you to, gets you to
profitability and to and to have

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long enough runway.
And so I think that, you know,

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you, you, I, I think that and if
I look at that and that problem

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was that they were kind of
trying to do that in isolation.

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And so I went back and I sat
down with them and they said,

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look, let's look at this again.
And they, they had ways to

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monetize what they were doing
that they weren't doing.

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And, and that's what they needed
to do.

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And that's the only way out of
where they've got to.

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And they're, they're doing that
now.

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But you know, they were, they
just put their head in the sand

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and they weren't really facing
the brutal truth.

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And so I think, you know, I
think before you go to market

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making claims that, you know, be
honest if you're not going to,

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if it's not going to work,
don't, don't go to market.

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Just work out how, how you can
change it.

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So it does work because there's,
there's always a way to, there's

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always a way to kind of monetize
and, and, and revamp and pivot

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00:16:52,560 --> 00:16:54,840
to make it work.
And sometimes they, they just

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try to get more funding for what
they're doing.

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So, yeah, yeah.
I think that's kind of great

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advice to finish on.
I think a lot of founders,

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definitely a bit of a reality
check because there's certainly

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ways they can get there, but
often they're just strong, the

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00:17:06,880 --> 00:17:09,640
upward graph without too many
ways to get there.

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And Alexa, thanks so much for
going to the podcast.

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00:17:12,720 --> 00:17:14,319
That was a really great
conversation.

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00:17:14,319 --> 00:17:16,760
You should a lot of really
viable interesting for both

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00:17:16,760 --> 00:17:19,000
founders and investors, which is
unique.

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00:17:19,000 --> 00:17:20,720
So thank you for your time.
Thank you.

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00:17:20,720 --> 00:17:21,400
Good luck.
Thanks for me.

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00:17:21,800 --> 00:17:23,440
OK, best of.
Luck.

357
00:17:23,440 --> 00:17:26,599
Thanks.
Hi, thanks for listening to this

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00:17:26,599 --> 00:17:29,480
weeks episode of the Founders
and Funding podcast.

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00:17:29,800 --> 00:17:32,160
If you'd like to be a guest or
have a guest suggestion, please

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00:17:32,160 --> 00:17:33,960
get in touch.
Thank you.