May 27, 2026

Ep 23 - Aleksandrina Ikonomova - Exited Founder & Angel Investor

Ep 23 - Aleksandrina Ikonomova - Exited Founder & Angel Investor

In this episode of the Founders & Funding Podcast, Philip speaks with Aleksandrina Ikonomova, exited founder, startup mentor and angel investor.

Aleksandrina brings a rare combination of perspectives to the conversation, she has built and exited her own companies, works with VC portfolio startups on turning around underperformance, and invests her own capital into early stage founders. She shares what she really looks for when investing, why the best founders are defined by their relationship with the problem they are solving, and what it actually takes to survive the emotional and operational demands of building a startup. They also discuss when fundraising makes sense and when it doesn't, why being coachable is not always the compliment people think it is, and what ruthless execution really looks like in practice.

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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 Alia, welcome to the Founders
and Funding podcasts.

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Hi there, thanks for having me.
It's my pleasure to have you on,

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Arlie.
Just to kick us off, could you

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tell me a bit about your company
and your role?

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Yes.
So currently I work with Bisana

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Labs, which is an agency
operators agency that works with

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VC portfolio companies on their
underperformance or to say and

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we go in, help them with
operations, improve their

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metrics and either prep them for
the next fundraise or we prepare

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them for an acquisition.
So my partner has been in M&A

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specifically for SAS Technology
over 20 years and I myself am an

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exit founder and this is pretty
much what we do at the moment.

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And I also enjoy invest on the
side in some of the companies.

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Fantastic.
And what does an average day

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look like right now?
It's a very interesting

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question.
When you work with start-ups,

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there's rarely average anything.
But usually because with the

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start-ups, we work on a weekly,
monthly and quarterly basis.

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So Mondays and Wednesdays are
for strategies.

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So we analyze what we've done
during the week and because we

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have big batches of start-ups,
so we have to divide it, one at

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the beginning, one in the middle
of the week.

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So we sit down, we look at the
experiments that we've mapped,

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we look at the results and we
decide whether to continue, what

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have we learned?
Is there anything to put in our

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playbooks or is it something
that we have to adjust to move

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faster, etcetera.
Then we look at how the tools

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are performing, is everything
working OK, what decisions were

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made during the week, etcetera.
Then on the rest of the day, so

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it really depends.
It's just putting fires down,

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talking to Obcs, fixing juice
and things like that.

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So it really depends on the day.
But as a person, on a personal

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note, since I have to be very
focused and agile, but I'm the

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network a lot, I wake up on my
own very early.

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So six, I'm already up whether
I've went to bed in the next the

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previous evening at 2:00 AM.
So my my internal watch is

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already waking me up at 6:00.
I have a very strict morning

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routine when it comes to just
getting in in the right

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headspace.
So I usually meditate, breath

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work, writing down thoughts,
ideas, anything and then just

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sit down look at the tasks for
the day.

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I'm I'm notion obsessed person
so I have everything in notion.

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Everything is tracked hour by
hour, everything is written

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down.
Everything is whatever I can

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have automated with Co work, of
course.

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And yeah, just hands down
working until I want to say 678

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depending on the day.
Because most of the days I also

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have a lot of networking events
that I have to go to.

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Not have to, but usually want to
because that's where we meet

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with other founders, other Angel
investors and other VCs and come

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back home, work a little bit
more and go to bed and repeat.

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Well, it sounds like a really
good routine for success and

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certainly working for you and
and you're certainly working a

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lot of different, different
areas.

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And so I suppose talking about
some of these startups that

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you've invested in and why were
they the right choice to invest

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in?
Umm.

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So I, I've just just to give you
a little bit of context.

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So I have been an entrepreneur
for seven years now.

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I've done multiple companies in
different industries.

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Some were very successful, some
not so much.

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And I exited last year.
My biggest exit was last year.

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And that's when I decided to
give back to the community by

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investing a little bit.
I do smaller checks up to 10K

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and I do early stage, so there
needs to be some kind of

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attraction or at least very
clear signal why the founder

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thinks it's worth pursuing that
problem or solution and why they

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want to dedicate the next 20
years of their life in that

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specific area.
Because it's becoming very

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popular and modern to become an
entrepreneur, to fundraise, get

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in that.
I would say a rat race.

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It could be sometimes without
giving, like having a clear

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thought process.
Why would I do that?

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So for me, it's quite important
to of course, to see that the

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founder really has, I wouldn't
say passion is the right word,

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but is really irritated with the
problem.

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Like they really are pissed off.
Excuse my language with the

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problem or with how things are,
and usually it's tied to a

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personal story.
No, I, I was a bad founder

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because I was easily distracted
by by the next interesting idea,

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next interesting problem,
etcetera.

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I'm just very good at operations
and say, oh, so that's that's

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why I managed to sell a company.
But the best founders I see,

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regardless if I invest in them
or not, are people who could

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very clearly describe me, the
relationship they have with that

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problem, if I could say so.
And then it's of course an

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operational level.
So seeing if the founder can

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manage their own gals, can they
properly manage themselves,

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their emotions?
Because it's a very emotional

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ride.
And it's very difficult to

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predict whether they will be
able to do that when times get

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calmer because a lot of founders
naturally thrive in gals.

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But when things get calmer, they
tend to create that kills

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themselves.
So it's an interesting aspect of

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it, but that's usually the job
of the later stage investors to

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figure out how to navigate that
situation.

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So yeah, that would be that way.
Pretty much it.

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How they execute, how they
learn, how quickly they fail,

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test, experiment, do things and
what is their relationship with

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the problem?
Yeah, I know.

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Certainly I think from the sit
ups I've worked with, I've

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always seen the ones that have a
bigger problem to solve and ones

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that have really experienced the
problem or obsessive or fixing

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this and they're the ones that
are going to be successful and

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small problems don't result in
in companies wanting to to pay

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to solve them.
In terms of those those

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companies, the startups you've
invested in early, do you have

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any examples?
Is there a company or two you

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could talk about that you've
invested in as examples?

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Yes.
Umm, well, I haven't asked for

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permission to specifically speak
about them publicly, but I can

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give an example of a company
that for me executed very well.

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So one of the they have they had
to change their ICP dramatically

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because they like they had like
very long sales cycles.

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It was B to BAI software that
replaced a certain workflow, but

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it didn't.
So it did solve the problem for

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the I, the first ICP that they
went after.

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But the problem was that there
were so much, so many COM

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competitors there.
It was so difficult to the

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decision maker.
The decision maker is very

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different from the user, so 3-4
steps ahead.

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So usually they weren't as
embedded in the industry as they

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would have have to in order to
succeed.

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They did have a one or two big
clients, which was a great

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success, but that wasn't enough
for them to be able to move as

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quickly as it's needed at this
stage.

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So we sat down.
It's a company that I've also

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worked with.
We sat down and we assessed that

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and we had to dramatically
change the ICP and the

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propositioning and the way they
marketed themselves, the way

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they approached their ICP,
etcetera, which could be very

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uncomfortable when you're like
the early stages and they did.

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And at the beginning the
results.

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So it was easier to get to the
ICP.

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The calls were much more
frequent.

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They received feedback much
quicker, which was very

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important in terms of product
building because with the big

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companies that wasn't the case,
but the revenue was slower

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because they had to change their
pricing as well, much slower.

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But in the long run, that was
the right decision.

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And doing something like that
requires a lot of self trust and

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a lot of like willingness to
solve the problem regardless by

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anything.
So that's for me is a brilliant

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example of someone who looked at
the long term game instead of

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just, you know, because a lot of
founders just go for a certain

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market because they think that
would sound more interesting to

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an investor instead of thinking,
OK, how can I improve my

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metrics?
How can I improve my nostal

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metric?
How can I improve cash flow

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instead of just thinking, OK,
what would sound great to an

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investor so they can invest in
me?

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So that's that's a great example
for me for a brilliant founder.

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It certainly is.
And what is the best way to fund

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a startup's journey?
So in terms of do you think it's

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better to start bootstrapping or
to start trying to get into

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investment?
Or is there a preferred path you

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think that that works for
startups?

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I don't think there's a
straightforward way for every

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startup.
So it really depends on the

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industry, on the capabilities,
on the level of experience of

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the founder.
Now it's becoming more more

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easier to build things and test
things.

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So what what was used to
consider pre seed is no longer

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valid.
So you cannot just go with an

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idea unless you're like for
Timex the founder, that's that's

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different ball game.
But you have to have like a very

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solid proof that you know what
you're doing, or at least you

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have some kind of a very strong
signal that it makes sense to,

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to, to build this.
And again, it really depends on

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the, on the, on the industry and
it really depends on the country

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as well.
So for me, when I moved to the

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UK, I've, I realized like how
easy it is to get UK grants,

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which was shocking to me.
I'm coming from Eastern Europe,

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I'm Bulgarian.
So the government doesn't take

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care of you as much.
It's all grind, make money and

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then figure it out and then even
try to fundraise because the VCs

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there are not as risk takers as
they are in the UK.

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In Europe general, we have a
problem with that anyways.

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So it really depends where you
are, what you're building, how

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quickly can you prove that the
problem is relevant to a bigger

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market, how how quickly you can
embed yourself in the market.

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All these factors come into
play.

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And I don't think every startup
should fundraise.

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I don't think everyone is
solving such a big core,

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significant problem for the
world that it requires A

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fundraising, I think.
And not every nervous system is

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built for fundraising as well,
because when you fundraise, this

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means that you have to put up
with investors who are not

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always the easiest people to put
up with.

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They're very demanding.
They require very high level of

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agency, very high level of
execution, very high level of

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sometimes investors don't know
that what they're saying, what

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they're doing either.
So you have to be like very sure

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of yourself that you are the
best person to make a final

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call.
So it really have to has to do

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also with are you capable of, of
dealing with all that?

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Because it's very, very
difficult journey.

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Yeah.
And that leads me to the next

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question of do you think who the
founders are, what, what skills

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they possess that impacts if you
should invest or what the kind

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of investment they should get.
So if you find that there were

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technical founders, if they
don't have those kind of

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technical skills, maybe the more
sales focused because that

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impacts if they should fundraise
or not.

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That again, depends on the
business.

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So whether or not you should
fundraise depends on is your

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business investable?
Do you really want to go that

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route?
And it doesn't matter if you're

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technical or not, if you have
been 20 years incorporate or

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not, it really doesn't matter as
long as you understand the game

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that you're playing.
And the game is much bigger than

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just fundraising for your
startups because I'd, I, I don't

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see enough entrepreneurs
understanding that it's a, just

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a huge vehicle.
What I mean by that is that you

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fundraise from your VCs, but
your VCs fundraise from LP.

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So those returns are expected
for too many, from too many

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people.
So you really have to understand

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that you're getting yourself
into a system that requires a

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certain level of execution speed
and people will push you and

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pull you in different
directions.

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And you have to be very stable
and sure of yourself in order

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to, to be able to, to play that
game while building a company.

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Because at some point even on,
especially on the later stages

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becomes a lot about politics,
especially in Europe.

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So you see like the best
founders that have fundraise

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that are coming from Europe,
they're a little bit I would say

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they, they know how to set
boundaries very clearly.

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So I have, for example, I don't
like the term coachable founder.

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For me, that's a really bad
thing because that means that

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he'll listen to everything
everyone has to say.

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And this is not a good thing for
someone who is leading Unicorn,

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let's say.
So for me, the founder has to

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be, to some extent, I would say
agreeable.

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Easy to work with, yes, but not
coachable because I like

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founders who tell me you're not
right because this, this and

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that.
And they know that like that

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chosen, they know what they're
doing and they have trust in

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their own discernment.
Although you never know what

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you're doing actually with the
startup, do you?

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That's a good point.
And how can companies attract

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investors effectively?
By building a successful

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business.
So if you, so if you have

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traction, that could be revenue
or not, depending again on the

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business and the business model.
If you're building something

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meaningful, people would like to
invest in you.

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If you're if you're sure about
what you're doing, if you're

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confident about what you're
doing, even if you don't know

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what you're doing, people will
want to invest in you.

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So of course there are
strategies of to prepare a good

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data room, to clean it properly,
to organize everything, have an

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eye to the detail, be a great
leader, create the formal

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effect.
So fundraising should happen for

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me in 2 to 3-4 months maximum.
If you've done the work and you

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should prepare like it's a
marathon and you should have

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someone that would be like your
Co founder essentially would be

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running the business while you
go out and fundraise because

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it's a full time job.
But attracting the right

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investors is it starts with
like, talk to them before even

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opening the round.
First of all, they can give you

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some good advice on how to
improve your metrics or what

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they would like to see.
Because after all, they've seen

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a lot and they know how the
industry is changing, what's

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moving, what's not.
Talk to as many people as

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possible.
Spread the word that you're soon

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to be opening a fundraiser.
Make sure your business is

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having the traction that it
requires to to have attraction

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in order to be fundable and
investable.

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Build everything systematically.
Build like a good data room.

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Show that you're someone who
understands all the aspects

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because as soon as you
fundraise, your business goes to

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the next level.
It cannot be as scrappy as it

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was in your, you know, 2 bedroom
apartment where you have 6

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people together.
In order to build the company,

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it just requires a different
type of decision making process.

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It has to be like a little bit
more sophisticated than that.

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So make sure you have all those
points together and then create

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the formal, so-called formal
which usually happens when you

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close like your lead and after
that go after the the smaller

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funds or the angels etcetera.
I see that Angel investments are

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also changing.
So less and less angels are

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willing to put the first check
before you have even built

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anything.
So idea based checks are more

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rare.
They kind of come in with with

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the seed receipt funds together.
So have at least one fund and

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build a relationship beforehand.
And that's really great advice.

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I'd finish up if you'd one key
piece of advice to share and

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fund in a startup, what would it
be?

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One key piece of advice.
That's a very difficult question

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for your data.
Make sure you know what is

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working, what you're working on,
why is it working or why it's

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not working, and be ruthless in
executing based on the

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information that you're
gathering.

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And that that's how you build
intuition because there are a

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lot of people are saying that
founders know best date because

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they have intuition, but
intuition is also memory.

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So you expression gets better
with more with the more

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information that you get.
So try to follow key, all the

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key metrics.
Why something is working when it

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why not be very, very, very
honest with yourself.

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So a good example I can give is
like founders love talking to

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people and that that that
doesn't mean that those people

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are your ICP.
So be very ruthless and saying

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like, is this person actually a
buyer or a good partner for my

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business or am I just spending
time talking to them because it

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feels productive when in fact
I'm just being busy.

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So be absolutely ruthless in
being clear on the metrics that

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matter.
Follow them relentlessly.

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Have a system based on which you
assess.

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What have I done?
Is it working?

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Is it not?
If it's not, why is it not

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working or why is it working?
And what's the next step to

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build upon on that and keep
track of all that?

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Because this is this compound
effect at the end of the day

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00:19:27,200 --> 00:19:30,560
will help you not repeat and go
in circles with the same

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00:19:30,920 --> 00:19:35,240
decisions and same same
mistakes.

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That's really great advice to
finish on.

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Alia, thanks so much for coming
on the podcast.

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I think you shared a lot of
really great advice, some of

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which a lot of which I haven't
heard before.

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So I think there'll be a lot for
for founders and investors to

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take away from the conversation.
Maurice, thanks for having me

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and happy to help.
Thanks, Alia.

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Hi, Thanks for listening to this
week's episode of the Founders

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00:19:58,680 --> 00:20:01,160
and Funding podcast.
If you'd like to be a guest or

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00:20:01,160 --> 00:20:03,240
have a guest suggestion, please
get in touch.

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00:20:03,920 --> 00:20:04,280
Thank you.