March 23, 2023

#71 Scaling Startups: Lessons Learned from Two Decades of Experience with Benjamin Friedman

#71 Scaling Startups: Lessons Learned from Two Decades of Experience with Benjamin Friedman
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In this episode of the podcast, we sit down with Benjamin Friedman, a startup veteran who has spent over two decades helping tech founders build and scale their companies. Benjamin shares his insights on the foundation that a startup must have before it's time to start thinking of scaling, the common mistakes that founders make, and the characteristics that a successful founder should have. He also talks about how to avoid burnout and be resilient, gives an example of a company that did it all right, and shares his thoughts on whether every startup needs to seek funding to grow. Lastly, we discuss his recently published book, Scale: Reach Your Peak, which offers over 130 articles on leadership, growth, sales, marketing, operations, finance, and teams.


Find more about Benjamin here:

https://www.webuildscalegrow.com/

https://www.linkedin.com/in/benjaminbfriedman/

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Hello and welcome to a new
episode of the CTO show with

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Mohammed.
I'm your host Muhammad.

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And as you know, in each
episode, we explore different

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topics Trends inside strategies
in areas like digital

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transformation emerging texts
and startups and

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Entrepreneurship.
And as, you know, sometimes I

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would have guessed with me who
are thought leaders in the areas

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of intrapreneurship.
And technology.

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And today, I'm very thrilled to
have with me today from New York

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City.
Benjamin Friedman, who joined me

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to talk more about how to scale
a start-up and take it to the

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next level.
So first of all, thank you very

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much.
Benjamin for being with me on

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the show today, if you can just
give little bit introduction

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about yourself and what you,
what you do.

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Sure, thanks so much Matt for
having me here, glad to talk

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with you and your audience.
So, I've been working with

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scaling startups over 20 years,
most of that time has been as an

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employee, but recently, as a
consultant I've worked with a

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number of Technology startups.
I've also consulted for a number

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of startups working with
technology companies as their

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customers a B2B set up and I've
been really on this Journey to

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figure out the best way to scale
and grow businesses thinking

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about how to do that efficiently
quickly.

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My Foundation was business
operations and finance.

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But being in the startup world,
I found myself across different

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areas of leadership.
So, looking at sales marketing,

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any aspects of client service,
really thinking about how

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holistically to grow the
company.

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So that everyone's working came
together and you're moving past

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the stage of a bunch of people
working together in a room and

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starting to think more like a
company so that you can grow as

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quickly as possible.
That's cool.

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If there any specific
vertically, you focus on or you

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work with any any kind of
startup.

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So I Ministry agnostic for your
audience.

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One of my gigs was at a B2B SAS
company that did data analytics.

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I was there for three years as
CFO, I put in a lot of Of

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infrastructure on the business
operations and finance side.

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Then I left.
As the next fundraiser, was

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really applied to developing the
product and a couple years after

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that they were acquired by VIP
WordPress part of automatic.

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So that was a nice success
story.

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Okay, that's cool.
Now from Europe experienced

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Benjamin, What is the
foundation?

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I would say that a company
should be built on so then we

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can tell them.
Okay guys I think we you are

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ready to go to the next phase.
What is this Foundation?

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Especially when you would work
with with a client.

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Sure.
So the way I think about this

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might be a little different than
some of your audience, but I

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always want to focus in on
first.

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What is the founder problem fit
in?

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Is this person so consumed with
solving a problem that no matter

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what happens, they will continue
on their journey and because

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you, and I know a lot of things
will happen along the way the

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market will change.
The investors might change the

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team might change, but the
founder and the problem, they're

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trying to serve us all rather
are the constant that will be

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the throughput in their Journey.
So I look at that and I say,

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okay, how does that transformed
into vision and values?

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Our they going to Assistant, we
strive to tackle that problem.

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And then from there, it's
starting to look at the pieces

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necessary in order to solve the
problem.

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I'll one of the biggest
challenges for Founders is

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knowing where to apply limited
resources.

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And so I want to see that the
founder has thought about how to

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apply the right pieces to
immediately starting to solve

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that problem.
Yes you're going to need all the

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different functional areas.
I talked about before but what

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are the two or three things
you're looking to do immediately

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in order to demonstrate?
Rate that you can get traction

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on solving this problem and
generate product Market fit.

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Okay.
Would that be like in the area

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of placing?
The right resources is like

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sales marketing and you know,
Market I would say analysis or

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is it like more into just
overall structuring and funding

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for the company?
I mean, the area that you try to

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help your clients with Yes, so
by the time I'm working with,

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most of my clients, they've
attained some product Market or

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service Market fit, and now
they're looking to take a

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fundraise or they're looking to
take their revenues and really

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apply them to reach the next
level.

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So, I'm talking with the founder
and trying to decide where are

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their areas of strengths and
where are their areas of

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weakness?
So I can supplement their work.

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And one thing that I found in my
my own journey is that a lot of

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times Founders who are Amazing
at getting this company off the

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ground and making something
happened at going from 0 to 1 or

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in this case, 0 to 1 million.
They then have to be a

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completely different person in
order to scale the company to

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the next level.
And some Founders can do that.

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It's a distinct skill set which
some people are Renaissance

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leaders and they can switch
gears and do things very

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differently.
But for most Founders, they're

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much more excited about the
product Market fit.

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Or Business Development or the
next fundraise and they would

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rather Outsource to some extent
scaling, the company and

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building the infrastructure.
And that's where I partner with

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Founders and say, okay, you do
what you're best at and bring me

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in to focus on some of the other
areas.

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That's cool.
Now, another fact that everyone

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knows that and it's coming, it's
not only in the US because I

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follow the, you know, tech
companies in the US.

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But I've seen it in every single
market and even here in in In

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the Mena region or witnessed
region.

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We know for a fact that
approximately get, we can say,

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only ten percent of startups
will succeed, right?

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What do you think is the common
mistake that Founders?

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They do that.
You have seen it happening.

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Multi-tap multiple times across.
You know, you've you'll carry.

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So what are your takes on this
and maybe some advices to new

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founders Yes, certainly I think
one thing is that Founders have

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to really be curious about how
to do their role better and how

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to approach the market better.
So on the one hand you're going

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to get a lot of feedback and
you're going to have to ignore

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it in order to keep pushing
forward.

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But on the other hand, you do
have to be open to certain

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advisors, certain leaders,
certain facts, and Trends in the

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market and take that information
into account and it's a fine

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line, right?
Perseverance.

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And understanding hit that
middle where some people are

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saying, don't do it.
In some people are saying do it,

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but as a Founder, a lot of
people run into trouble where

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they just keep pushing and they
follow the sunk cost cognitive

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bias and decide they're just
going to keep going, despite a

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preponderance of evidence.
Number two, is that ability to

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shift?
I mentioned earlier that nobody

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almost.
Nobody is perfect all around.

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Perhaps, there is somebody out
there but the same Who's great

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at fundraising ad sales at
product development, at

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understanding the technology at
managing teams is highly

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unlikely and so the founder has
to recognize where to find

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people to compliment them and
support those aspects of the

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business, otherwise you'll see a
company grow and fall pretty

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quickly.
And then I think the third area

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is really not recognizing how to
delegate to the team around you

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and find the areas where they
need to.

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Level up as quickly as you a lot
of people think of Delegation is

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like, here you do this instead,
I didn't go gation is a lot of

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work on the founder of the
leader has to sit there and say,

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okay what is the destination?
We're trying to reach.

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Let me give him some pointers
about staying on their Lane and

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not running into too much
trouble, but let me avoid

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setting the path.
If you picture a mountain we're

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trying to get to the top of that
mountain.

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You don't tell people.
This is the exact path to take

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you say.
There's a top of the mountain

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Beware of the Rocks, falling
over here.

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And otherwise come to me is
needed in order to reach the

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mountain of your own because I
have another Mountain.

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I have to scale.
Yeah I agree with you on this

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point.
Now this you know, let me think

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about the next question and it
is.

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Sometimes we see this happening
because there is kind of a lack

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of leadership skills with the
founders.

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Like what do you think?
Are, you know, the

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characteristics or the
personality that the founder

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himself or herself should have
so they can be outside as joy to

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do these changes.
Yeah, so I think two important

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ones come back to feedback.
One is feedback from peers and

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advisors are you really need to
surround yourself with a handful

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of people who will not just be
cheerleaders, but they will

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actually sit there and tell you
Do what you need to hear.

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Not what you want to hear, and
that's very important.

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It's not necessarily people.
You want to hang out and have a

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conversation with outside of
work but you want to talk to

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these people from time to time
and say, Hey I want your honest

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opinion and they're going to
tell you what's wrong with you

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and your ideas and you need to
be open to that feedback.

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The second type is talking with
your team and with your eventual

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customers, you know?
If you don't have the product

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out there, yet your future
customers.

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If you do, you have to hone in
on your existing customers?

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And again, you have to ask the
hard questions, what's good

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about this but also, what will
make it better.

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What problems are you seeing
this product solve?

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What is it that we could do?
That would make your life

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easier.
And really constantly taking

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that feedback and be able to sit
through it and find the best

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pieces of evidence because you
will change.

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You will change as a leader,
your product and team will

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change over time.
And so, you have to be

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constantly Only open to the
feedback as the markets and the

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customers evolve you want to do
the same.

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Yeah.
Now I gave this brought the

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second question or the next
question from my side.

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Now while the company is on this
journey to grow whether it's

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from 0 to 1, 1 to 10, or 100 or
even to become a unicorn.

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We hit a lot about, you know,
like Founders being like burnt

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out and, you know, like a lot of
pressure.

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So All I would say found the
should be paid if you would like

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to call it kind of a resiliency
to this pressure and avoid a

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burned-out.
I love that question and the

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topic of resiliency is so
important.

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I mentioned earlier, that the
founder problem fit is essential

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to a successful Journey.
The other thing we have to

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recognize is that the other
constant in that journey is

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ourselves, and so making sure
that we are We are taking care

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00:11:36,000 --> 00:11:40,100
of ourselves for the long term.
You asked earlier about some

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fumbles and sometimes when
founders are just thinking about

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success, their only goal is to
make money, they lose track of

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the day-to-day and that includes
taking care of ourselves.

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So that, that end, I think you
have to look at it, physically,

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mentally and emotionally.
And so physically, it's making

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sure you exercise your diet,
your sleep.

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A lot of times we're tempted to
think, oh, if I work on this

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one, Our, I'll get so much
further but that becomes

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detrimental to your long-term
goals mentally.

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It's making sure that you have
people, you can talk to and work

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through some of the problems.
And just recognize, you're going

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to be bad days for no reason,
and have an outlet for that, and

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then emotionally.
It's being able to channel your

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passion productively, but if it
becomes too much, then again,

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it's being able to seek help
sometimes Founders, get

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professional help and that ends
up allowing them to run.

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Run the marathon and reach the
Finish Line.

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Yahoo, it's very informative now
because you you have this long

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experience, also Benjamin like
even if you cannot name the

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company name, I mean, but what
would be the best scenario?

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You know, of something that you
have seen where, every single

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right step was was done.
Like, do you have anything in

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mind on that?
Sure.

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So I want to work with an
e-commerce company and they came

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up with a new way to make
payments online and they started

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very small.
The fact the founder was doing

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consulting and then he brought
in a co-founder and they started

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growing and all along the way.
There were several things in a

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journey that made a lot of sense
to me.

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So one was all the founders were
willing to experiment, but

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mitigated the risk.
So they'd say, okay.

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We're going to put a lot of
money towards this experiment.

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We'll try a new product, will
try reaching out to a new

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region.
New demographic will spend X

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number of dollars.
Well, we're not going to go

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crazy with this experiment and
if it doesn't work, they were

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going to stop running the
experiment on the second thing

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that I really admired was their
recruiting strategy.

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And I found that the third
co-founder and quotes was a

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person in charge of recruiting
Because she did an absolutely

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incredible job of bringing
people into the company who were

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more intense and knowledgeable.
And eager to solve these

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problems than even the existing
Workforce, and everybody was

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already wound up.
So, what she did is she found

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out what was the position we're
looking for describe an ideal

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employee for that role.
I'm going to bring in some

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people who meet minimum criteria
and she would test them on

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standardized levels and say,
okay, these people are capable

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of the job.
Now you talk to them and see if

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they will be a great fit in the
company and then the last piece

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of that, As we did recruiting
and rounds.

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So we would bring in a bunch of
people and then we would rest

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for four to six months.
Let those people get acclimated

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and then bring in the next round
of people and now is super

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helpful because it gave everyone
a chance to ramp up to acclimate

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find out.
If somebody's not working out,

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we can adjust and then bring on
the rest of the people.

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Instead of, you know, we see a
lot of technology companies now

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that brought in a ton of people
and now of course are in a

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position where they have to let
go.

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A lot of them, because they
weren't thinking Through in a

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regular basis.
Yeah, that's a really insightful

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I would say.
And the question I want to ask

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you now, if you allow me as a
lot of times, you know, people

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think that Raising fund is a
destiny, right?

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And I see this, a lot of.
So actually, I covered this in a

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previous episode by myself.
And you see, like, people only

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knows like, okay, we gotta go to
avert when Venture capitalists,

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you know, get some money.
But while sometimes, maybe it's

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not the good time to do that and
especially with all the, you

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know, macroeconomics that's
happening currently.

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So, do you think like it's a
Destiny for every startup at

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some stage?
To get some funds.

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I love this question as well and
it's funny.

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I'm going to start with an
analogy, I don't know if

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everyone in the audience is
married, but I think people get

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it.
A lot of people see a wedding as

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the destiny in a relationship.
Two people meet, they fall in

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love and they get married and
that's where the story ends.

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But many of us who've been
around for a while.

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Know that Dad is just one of
many milestones in a

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relationship.
That hopefully will last a long

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time.
And those people we see who are

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happy happy enough that they
stay together.

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They support each other for a
long time.

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The wedding has nothing to do
with that.

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Fundraising is the same thing.
Fundraising is like a small

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wedding, a bunch of people,
raise some money, there's a

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celebration, there's a bunch of
Articles and it may be a chance

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to grow the company.
It may be part of the journey

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but in and of itself it is not a
celebration and Some Founders

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and maybe this is implied in
your question.

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For some Founders Fund Raising
is the exact wrong thing to do

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and I would say, here's the
thing.

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You have to think about the
trade-offs, immediately, you're

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trading off equity for cash.
If you think that that cash is

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going to exponentially drive
your journey, it's really going

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to help you solve the problem
that much faster.

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It's going to be part of your
solution then great you know

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think about it, go forward.
If you're doing it because you

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feel like having that money will
solve the problem, then you

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should rethink what you're doing
there again, if you're focused

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on solving the problem, you're
coming up with a minimum viable

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product, you're putting it out
there for people to use, you're

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seeing if this has an impact in
solving the problem.

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Then once you've gotten that
fit, you can say, okay, I'll

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draw in money because now I want
to exponentially solve the

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problem.
That I know I can solve in this

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particular small.
Subset then it makes a lot of

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sense.
The final point is that you're

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bringing on investors into your
journey, those people are going

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to have strong opinions and you
have to be ready to manage that.

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If there are strategic investors
who are going to help you in the

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00:18:00,200 --> 00:18:02,100
journey.
Great, that's awesome.

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If they're people with money who
are going to make your life more

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difficult and solving that
problem, then that's a downside

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00:18:08,600 --> 00:18:09,900
that you really need to
consider.

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That's cool.
So before we come to the end, I

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00:18:13,800 --> 00:18:17,100
know that you have, put some
handbook called scale.

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I'll reach your Peak, right?
And you've put like multiple

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00:18:20,100 --> 00:18:23,100
articles over there.
Can you like tell us a little

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00:18:23,100 --> 00:18:28,100
bit about this handbook and you
know, what's the context of of

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00:18:28,100 --> 00:18:30,500
the topics you covered there?
Sure.

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Thanks so much.
Yes, I put together book after

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00:18:33,800 --> 00:18:37,600
about three years of writing.
It's really I started the

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process wrestling with one
topic.

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00:18:40,000 --> 00:18:45,500
After another customer success
product Market fit fundraising

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00:18:45,500 --> 00:18:47,100
like we talked about these are
all set.

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It challenges that I've run into
myself and with clients and I

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00:18:52,800 --> 00:18:55,500
started to write about each one
and then I realized okay there's

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00:18:55,500 --> 00:18:58,200
a theme Here.
Founders who have gotten some

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traction are now being asked
questions about running a

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business.
So before they were building a

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00:19:03,808 --> 00:19:07,500
product and now they're running
a business and this book looks

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00:19:07,500 --> 00:19:10,700
at all the different challenges
that those Founders May face.

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And it doesn't in a very modular
way.

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So if you have a particular
question about say public

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00:19:16,100 --> 00:19:19,100
relations, You can go and read
for five minutes.

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00:19:19,500 --> 00:19:22,600
Learn from the research, I did
and add it into the book.

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00:19:22,800 --> 00:19:26,700
It's a concise piece on public
relations, and you can take that

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00:19:26,700 --> 00:19:29,000
with you and then you can go
back to the book and three

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00:19:29,000 --> 00:19:32,000
months and six months as you
start to think about another

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00:19:32,000 --> 00:19:36,000
challenge, it gives you a
framework for how to start to

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00:19:36,000 --> 00:19:40,100
resolve that and some immediate
next steps for you to bring on

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00:19:40,700 --> 00:19:42,500
good.
That's, that's really also like

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00:19:42,500 --> 00:19:45,300
about believe.
It would be very helpful before

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00:19:45,300 --> 00:19:50,100
we close like For today.
Benjamin anything else you want

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00:19:50,100 --> 00:19:53,400
to add any advice want to say?
And also want to ask you like

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00:19:53,400 --> 00:19:57,300
where people can find more about
because my audiences worldwide

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00:19:57,300 --> 00:19:59,900
by the way.
So it, so if anyone wants to get

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00:19:59,900 --> 00:20:04,700
in touch with, Yeah, sure.
I would say my final piece of

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00:20:04,700 --> 00:20:09,400
advice and this is covered a lot
in the book is really hone in on

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yourself what you want out of
this journey, what you can bring

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to this journey, there are some
ways that we can grow and

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00:20:16,600 --> 00:20:18,500
develop.
And there are other ways we're

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00:20:18,500 --> 00:20:20,200
going to need people to support
us.

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I'm bringing on people to
support me and my clients all

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the time.
I've worked with fractional

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00:20:25,500 --> 00:20:30,000
ctOS, and, and other experts,
because I know my limits, right?

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00:20:30,200 --> 00:20:32,700
We have to think about Out that
as we're going on this

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entrepreneurial journey and then
to your other question, you can

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00:20:36,500 --> 00:20:41,600
visit w-w-w dot, we build scale,
grow.com.

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00:20:41,700 --> 00:20:44,600
You can see a lot of my work
there and then I'm posting on a

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00:20:44,600 --> 00:20:47,100
regular basis on LinkedIn.
That's great.

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00:20:47,100 --> 00:20:51,500
I will make sure that I will put
this into a episode description

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00:20:51,500 --> 00:20:54,600
and also a link for your
LinkedIn profile.

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Well, that's really very
insightful.

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Very out.
Say eye-opening conversation, I

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00:21:00,900 --> 00:21:03,700
hope Today for my audience,
whether they are listening to

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00:21:03,700 --> 00:21:07,300
the podcast or watching on
YouTube, thank you very much

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00:21:07,300 --> 00:21:13,100
Benjamin for your time today and
I appreciate it for my audience.

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Thank you for tuning.
And as usual, if you have any

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00:21:16,100 --> 00:21:20,000
feedback about this episode or
about the show in general, you

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00:21:20,000 --> 00:21:24,000
can get in touch with me, either
by email or on LinkedIn or

375
00:21:24,000 --> 00:21:25,700
Twitter.
I'll be more than happy to

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00:21:25,900 --> 00:21:29,400
discuss that with you if you
want to come to the show and

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00:21:29,400 --> 00:21:31,600
join me.
Like what Benjamin When did

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00:21:31,600 --> 00:21:33,500
today.
So I'll be also more than happy

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00:21:33,500 --> 00:21:36,900
to discuss that with you.
And don't forget to subscribe to

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00:21:36,900 --> 00:21:40,200
the YouTube channel and also to
the podcast which is available

381
00:21:40,200 --> 00:21:42,200
on audio podcast platform.
Thank you very much.

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00:21:42,200 --> 00:21:31,900
And until we meet next time,
When did today.

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00:21:31,900 --> 00:21:34,700
So I'll be also more than happy
to discuss that with you.

384
00:21:34,900 --> 00:21:38,500
And don't forget to subscribe to
the YouTube channel and also to

385
00:21:38,500 --> 00:21:41,500
the podcast which is available
on audio podcast platform.

386
00:21:41,500 --> 00:21:43,600
Thank you very much.
And until we meet next time,