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June 3, 2025 22 mins
Creativity and strategy can seem like two sides of the same coin when it comes to business scaling, but they run well together when combined. I discuss how to do that in this episode with my guest, Lysle Wickersham. Lysle’s unique crossover skill set and insights not only transform startups and SMEs into scalable, successful ventures but also redefine the very essence of creative capitalism, masterfully blending positioning strategy with storytelling and building intangible equity to drive growth and build enterprise value.     Lysle is an combination of two career paths that led him to his current business. He grew up as a creative director in integrated communications and brand development and advertising and eventually built a large agency that he ended up selling. After that Lysle ran a couple of tech companies connected to venture capital groups. He founded an investment bank and did a strange crossover for a creative person into mergers and acquisitions working with private equity and venture, a more strategic endeavor. What felt natural to him was the integration between the pragmatic side developing sound business strategies and the creative side of expressing the attributes of a company that builds the emotional connections. The truth is if you do both of those things well, that’s where the money is. Where to Start When it Comes to Blending Creativity and Strategy Creativity and strategy don’t run at the same time; it’s a linear process. To be creative you first need to be strategic. Every business must start with core positioning. Who is the target market that you’re trying to reach? All of this at first is connected to the founder by the company’s goals and visions and what they want to be and build. You take that and decide who would buy that and who’s going to scale with you so you can grow. You need to ask: What is the context that you are in the market in other words what space are you playing in, what’s your primary point of differentiation and what’s the proof that you can deliver on that point of differentiation? You must be able to deliver on that brand promise. If you do that stuff well and you have that core foundation that naturally leads to the attributes of your brand that align with your positioning and audience. That means answering questions such as: What do you look like? What do you sound like? What are the brand values from that you can discern your primary messaging? All of that then moves into things such as brand identity and communication strategies. The marriage between the two comes when you know who you are as a business and how you tell your story in a way that emotionally resonates with your potential clients. That’s the natural connection between the strategic foundation and the creative expression of that foundation. How to Know When You’re Ready to Scale It’s kind of an abstract way to look at the word, everybody wants to scale or grow. Every business’ goal is to get bigger and make more revenue. That’s a natural progression. There is no specific trigger for that. When you’re figuring out positioning for your business you want to make sure that the audience you want to build has room to grow. Then there’s market potential. That’s where there’s white space competitively where you can be different and be desired. All those things must go into consideration when you’re figuring out how to position a business to raise capital. You’re looking at the size of those marketplaces, how big they are, and what your potential to attract a piece of that market is. All those things must be calculated, especially if you’re talking to investors and you want to present a financial story to them about how your company can grow. How to Differentiate Yourself in the Marketplace That is the connection between strategy and creativity. When you create your positioning one of the core functions of that positioning is to articulate your core point of differentiation.
Mark as Played
Transcript

Episode Transcript

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(00:00):
Welcome to the Idea Climbing Podcast.
Creativity and strategy can seem like two sides
of the same coin when it comes to
business scaling,
but they run well together when combined. I
discuss how to do that in this episode
with my guest, Lyle Wickersham.
Lyle's unique crossover skill sets and insights not
only transform startups and small to medium sized

(00:20):
businesses into scalable, successful ventures, but also redefine
the very essence of creative capitalism.
Lyle masterfully blends positioning strategy with storytelling and
building intangible
equity to drive growth and build enterprise value.
We dive into topics including how to know
if you have a viable profitable business idea
with which to grow, how to uniquely differentiate

(00:43):
yourself in a crowded marketplace,
the one thing above all else that you
need to do to be both creative and
strategic when scaling your business, and other golden
nuggets of advice. You're gonna love this show.
Lyle, thank you for making the time to
do this podcast. I appreciate you.

(01:05):
My pleasure. Happy to be here, Mark.
And today, we're gonna be talking about how
to creatively
and strategically
scale a business.
Before we get into tips,
tricks, strategies, things like that, I'd love to
know when it comes to being creative and
strategic with scaling a business,
why do you get how did you get
so good at it? What's your story in

(01:26):
that world?
You know,
I'm really kind of an amalgam of two
career paths that led me to this place,
but I I grew up as a creative
director and integrated communications, brand development, and advertising
and and built a pretty large agency that
I ended up selling.
And after that run, I had a chance

(01:46):
to run a couple of tech companies,
connected to some venture capital groups, and founded
an investment bank, and kind of did a
strange crossover for a creative person into,
mergers and acquisitions and working with private equity
and venture and and scaling businesses and creating
value in those businesses to improve transaction multiples.
And,

(02:08):
what felt natural to me was this integration
between,
the pragmatic side, developing sound business strategy,
and the creative side of expressing
the attributes of a company that build the
emotional connections.
And the truth is if you do both
of those things well,

(02:29):
that's really where the money is buried.
When it comes to blending creativity and strategy,
where do you start? Does one come first?
Are they running tandem? What does it look
like? Yeah. No. It doesn't they don't
really run at the same time. It there's
there it's a bit of a linear process.
So
to be creative, you first need to be

(02:51):
strategic. Right? So every business has has to
start with
core positioning.
So, you know, who is the target people
you're trying to reach? And all this first
is connected to a founder or a company's
goals and visions and what they wanna be
and build.
And you take that and you go, I
will who who's gonna buy that? How do
you who's gonna scale with you so you

(03:12):
can grow?
What is the context
that you are in the market? In other
words, what space are you playing in?
What's your primary point of differentiation?
And what's the proof that you can deliver
on that point of differentiation?
Proof that you can deliver on the brand
promise.
If you do that stuff well
and you have that core foundation, then that

(03:35):
naturally leads to alright. What are the attributes
of my brand that
that align with that positioning,
with that audience. What do I look like?
What do I sound like? What's my the
brand values?
You know?
From that, you can discern your primary messaging,
and all that stuff then moves into things
like brand identity and how do I do

(03:56):
communications and all that stuff.
But the marriage between creativity and strategy comes
in, hey. I I know who I am
as a business.
Now how do I tell that story in
a way that emotionally resonates with the people
that I want to buy my stuff?
So there's a natural connection between the strategic

(04:16):
foundation and the creative expression
of of that foundation.
What does it take to build that foundation
to be ready not scaling yet, but how
do you know when you're ready to scale?
What does the foundation look like to say,
okay. Now I need to look at scaling?
Well, it's kind of a,
abstract way to look at the word. Right?
Everybody wants to scale or grow or whatever.

(04:38):
So, I mean, every business's goal is to
get bigger and make more revenue and, you
know, so that's kind of natural.
So there is no specific
trigger for that. But when you're figuring out
positioning for a business,
you certainly wanna make sure that that positioning,
that audience, what you wanna build has room

(04:59):
to grow, that there's market potential,
that there's white space competitively
where you can be different and and be
desired.
You know, all those things have to go
into consideration.
And when you're figuring out how to
position a business to raise capital, you're actually
looking at the size of those marketplaces, how

(05:21):
big are they, what is my potential to
attract the piece of that market, how big
is it. All those things have to be
calculated,
especially if you're talking to investors and you
wanna be able to present a financial story
for how your company can grow.
Well, once you get start to get that
stuff in place, as far as messaging and

(05:42):
everything else you just mentioned,
when does when does the scaling actually well,
better yet, before we get to scaling,
how do you differentiate yourself in the marketplace?
Once you know your sandbox, how do you
separate yourself from anyone that sounds like you?
Well, that is that is
the connection between strategy and creativity.

(06:03):
So when you do your positioning, one of
the core functions is articulating your core point
of difference.
So you've gotta nail that right away, and
that takes market research, understanding the competitive environment,
and and figuring out what is the place
where I can put a stake in the
ground, and I can own this position, which
naturally includes your point of difference.

(06:24):
So,
you know, a lot of this, Mark, is
connected to understanding how you build equity, and
equity over time is really how you create
wealth.
And equity happens by
owning space in people's minds, which which are
what brands do. And, generally, brands do that
through
creating emotional connections

(06:45):
as well as having a good product or
a good service. I mean, those become table
stakes, but sometimes the differentiator
can
be emotionally driven. What's the true difference between
Reebok and and Nike? Well,
Nike has been unparalleled that renting space in
our mind and having a position of, you
know, performance and

(07:06):
and and they just have dominated.
And they own that space, and nobody can
really take that away.
And these are the emotional connections. And the
objective of doing positioning and that kind of
stuff early on
is that it allows you to own that
space and and stay in that space and
own
it because that's how we remember things. That's
how our memory systems work.

(07:27):
So consistency over time is key. So you
do that strategic foundation work in the beginning,
and it informs how your brand lives and
breathes,
and you stick with it and stay with
it over time. And that's how you create
alignment, and that's how you get consistency, and
that's how you build equity.
So how do you if someone's listening or
watching, they realize, okay. I love what you're

(07:47):
saying. As far as getting
started with owning space in people's minds,
where can the smaller companies get started in
that realm?
It's really
it's really,
a simple process. It's not necessarily easy to
execute, but the process is really simple.

(08:09):
What is my IP or my assets? What
am I building? What's my product and my
service?
Who's gonna buy that?
How many of those people are there? How
big is that up market opportunity?
What what is it about what I do
or how I do it that is uniquely
differentiated
that I can own, then I can tell
people this is how I do it, why

(08:31):
I'm better,
and what is the proof that that I
can deliver on that. If you do that
foundational work from the beginning, your foundation is
laid.
You know? Because the idea is to to
refine that, define that, and then stay with
that over time.
So any small business can go through that

(08:51):
process. I don't care whether you're a plumber.
You can go through this process. Right? There's
all these people in in my market, or
they're all plumbers. And what is it the
way I do business that differentiates me that
will make people remember me?
Right? And that
that's not a complicated process. It just takes
doing your homework and

(09:11):
figuring out what that
is, determining your messaging structure around those points
of difference,
and then being consistent over time. So anybody
can do this.
Well, once you get I'm sure there's a
little more to it. Well, once you get
into it and you realize, okay. I've got
some mind space. Something's starting to happen here.
How do you maintain it and not just

(09:32):
be like a blip where you have a
really good marketing initiative? Oh my gosh. Everyone
knows us for a minute
and dip. How do you maintain mind space
once you start to get it? Think about
think about it this way. So if you
if you define your positioning and you define
your brand attributes,
building brand and building equity is not about

(09:54):
spend. It's about how you run your business.
So if you're a business and your value
proposition is
some sort of superior customer service,
then then how your phone people act, how
your salespeople act, every point of engagement
with your customers
reinforces

(10:14):
the position that you've created.
Right? And that builds space in people's mind,
and that that's what you become. So it's
really not about a blip in marketing.
It if you do this process well, you
have defined the core pillars that hold up
your company. What are the the key things
that make my company what it is? You
create clear messaging structure that aligns with that

(10:36):
positioning so that you make sure every piece
of communications
is supporting
consistent messaging. You hope make your salespeople
aligned with what is the important messaging that
needs to be communicated about what makes us
different. So it's really not about marketing activity
as much as it is about having that
foundational
consistency
across the enterprise and in the market.

(10:59):
That's really how it works.
So how do you know when to scale?
At what point of building and creating a
foundation
what's the trigger for, okay, we've got the
foundation.
I'm ready to scale. What does that pivot
point, tipping point look like? I don't think
that that's necessarily
the right way to ask the question.

(11:19):
So everybody
who's
growing a business or founding a business is
always looking to scale. That's the objective. Right?
So,
there is no point in time where suddenly
it's okay
to scale.
If you're structuring a business from the beginning,
you know, one of the first things that
you're doing is look making sure that you
have a scalable market for what you're creating.

(11:43):
So
so, really, you're you're you're trying to scale
from the get go. There's no, reason that
you're not thinking that way. So the first
thing that you're doing is, hey. I'm building
this or I have this.
Is there a market for what I wanna
build?
How many how much how big is that
market? How much of that market can I
take? Can I scale within that market?

(12:05):
So everybody's making that decision about where and
how they can scale from the beginning.
So there's no trigger point where suddenly you're
ready to scale versus not scale. There may
be a time when you're ready to
make noise in the market
and get things ramped up and stuff, but
you better have figured that out,
in the beginning.

(12:27):
Sort of a broader sense of any stage
of the business since, completely, it makes perfect
sense what you just said. You're always wanting
to scale.
What is the starting point of scaling then?
Not necessarily, like I said, the foundation. You're
all if you're a one person shop, but
for what if I hear you right, you
wanna scale. That's how you build the business,
how you own more of the marketplace. Everybody
wants to grow.

(12:48):
Everybody wants to grow. Right? So,
you know,
if a one person business might be a
little bit of a different con conversation,
you know, you're not really looking at the
market the same way as a as a
larger enterprise that's looking to scale and grow
and expand.

(13:08):
But, really, the first thing that you're doing
is, you you know,
in any business, identifying
a market where there's opportunity for you to
be successful.
So, I mean, those are the first steps
in in saying, hey. I have a viable
idea here.
And part of that assessment is that you
have a defined market opportunity

(13:29):
in which to grow.
So, otherwise, you don't have a business. Right?
So it's kind of fundamental to the very
beginning of the process.
How often should you evaluate and reevaluate the
market opportunity?
That's a good question. You know, markets evolve
all the time.

(13:49):
And once you're in market and growing, you're
you're constantly watching, you know,
the performance indicators of adoption of if you
have a tech product, you're watching the market
to see what's going on, you're following trends.
You know,
it's very much of a leadership responsibility
to make sure you're paying attention
to how markets evolve, how tastes and trends

(14:11):
change, and, you know, that's just part of
growing and running any business.
What do you do when a competitor sees
what you're doing and they they wanna take
market share away so they try to copy
you or sound like you? Is that a
pivot? Do you stick to your guns? What
do you do in that situation?
Yeah. It's another great question. I mean, at

(14:32):
the end of the day,
the objective of establishing
core positioning from the beginning
means you've picked your space in the ground
and you own it and you speak to
it consistently over time.
Generally, if you do that well, you preempt
competitors
from taking your space.
Right? Because, you know, two people can't say

(14:53):
the same thing and nobody wants to be
second in with the same position. So that
really
isn't a differentiated strategy for a competitor.
So if you do that properly,
then you own your space, and and you
can have some safety in that.
If people are really treading on your turf,
yeah, you stick to your guns, and you

(15:14):
stay focused, and you own your position, and
you don't don't let that waiver and,
make sure that you have a very strong
point of differentiation.
So
Well, when you get to that point, when
it comes to scaling,
are there plat are you always scaling, like,
even if it's a whatever degree angle, not
super high angle,

(15:35):
are you always scaling, or do are you
hitting plateaus,
breathe a little bit, reevaluate,
then scale again, plateau scale, or is it
one constant stream no matter what the angle
is? What does scaling look like? I certainly
can't speak to every business out there, but,
I don't think that,
businesses scale
in a consistent linear fashion.

(15:56):
I mean, there are ups. There are downs.
Things change.
You know, a lot of people will say,
well, for the most part, your business is
going up or it's going down. It rarely
flatlines.
And so most of the time, you're you're
trying to grow.
But, sure, there are trends. There are ups.
There are downs.

(16:17):
And things change all the time, and you
just gotta be able to evolve with with
the changes.
Well, with what you just mentioned with growing,
could you unpack a little bit about as
far as growth? Is it benchmark related? What
how do you how do you measure to
say we're on track with growth?

(16:37):
You know, there's a wide range of answers
to that from if you're a publicly held
company and you have fiduciary responsibility to shareholders,
that's a whole another conversation.
If you're a small business,
you know, the
KPIs or the OKRs,
you know, the objectives and key results that
you

(16:57):
choose to use to determine
what success is for you
can be different for for anybody.
But, you know, goal setting is a critical
part of leadership in any business,
and they've gotta be able to sit down
and say, hey. Our our growth goal for
this year is x, and this is what
we're looking to do. And then you evaluate

(17:18):
the company performance and people's performance against reaching
those
goals. So there is really no singular answer
for that. Mhmm. For a small business,
it's often very directly connected to,
you know, the stakeholders'
personal goals and
attaining this level of growth, and that's where

(17:38):
I wanna be, and there's nothing wrong with
that either.
So,
there is no set in stone answer for
that kind of question.
Well, you mentioned goals a few times. What
makes
how would you what would how would you
define a what makes a good to great
goal? What are the characteristics of a goal?

(18:00):
But, again again, it's personal.
Mhmm. It really is personal. So if you're
sitting down with a stakeholder
and you're trying to help them figure out
how to grow, which is a lot of
what I do with businesses,
You know, the first questions are always, what
are you looking to accomplish? Where do you
wanna take this? You know, what do you
have in the pipeline in terms of research

(18:21):
and development? What are you building?
You know? Do you have a
thing that you're trying to get to? Well,
then let's figure out how to get to
that place, and then what are the the
objectives that we wanna put in place that
we can then measure
that will
tell us how well we're doing in reaching
those objectives.
So each situation is completely different.

(18:45):
Is it the same thing for growth as
far as you said? The everything could be
different for different companies.
But as far as growth, do you really
do you recommend the the key performance indicators,
the KPIs?
What do you recommend to measure growth? And
I've realized it's gonna be a personal choice,
but in that business,
what kind of KPIs
do you suggest? Like, when you work with

(19:05):
clients, what kind of things do you suggest
they put in place?
Well,
you know, at the highest level, you know,
everybody's looking for,
you know, profitability
and and revenue growth. You know? I mean,
that's that's what we want. It's it's sort
of naive to think that we're everybody's out
there building business, and and they don't wanna
create wealth or make more money.

(19:27):
You know, that that's why we all do
what we do. We we work to to
make money and and, you know, we try
to build businesses to increase the business's value
and pay people well and keep people. You
know? So, at the simplest level,
you know, profitability,
and revenue growth,

(19:47):
are are tops. So, certainly, there are ton
of other
metrics that you're looking at,
and some people have different priorities. You know,
some people wanna, you know, build a
a certain kind of workplace or have more
altruistic
goals for their business, and that's okay too.
But, again, it's it's really

(20:07):
it's a personal decision. Of course, you know,
again,
publicly traded companies are a little bit of
a in a different ballgame. But you know?
Of course.
We have covered a lot of ground in
a short period of time. When it comes
to being strategic
and creative with scaling,
we talked about a lot whether it's reinforcing
something we said, maybe something we haven't touched

(20:27):
on yet. So I was like, I get
it. I love what I hear. This was
a lot. If you were to say, when
it comes to creative and strategic scaling, at
least do this one thing, at least do
this. What would you tell people to do?
I I would basically say
build
that core foundation
early.
Figure out what your brand's value proposition is,

(20:49):
what its core positioning is.
Do it early, and then stick with it
consistently over time because
consistency
comes from
alignment. Alignment comes from having that strategic foundation
clear and defined,
and that's how you build equity.
And equity ultimately is where

(21:10):
significant value and wealth happens.
So, yeah, do it early. Start early.
This has been excellent. If people wanna find
you online, what place or places should they
go to?
Well, I'm probably the only Lyle Wickersham
on LinkedIn, so I should be be pretty
easy to reach, and you can certainly connect
with me through my website,

(21:31):
brandthink.biz.
Thank you again, Lyle. I appreciate you. This
has been excellent.
It's a pleasure, Mark. Thanks for having me.
And scene.
Thank you for joining us today. I hope
you enjoyed the episode. I also hope that
you'll subscribe to the Idea Climbing podcast and
rate us on iTunes.

(21:52):
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