Upshots: Branding Your Startup with John Cantwell

With a record 5.5 million businesses starting up last year alone, it's not easy for early stage companies to stand out. Fortunately, John Cantwell, a creative director who specializes in brand and copy startups, is here to share his secrets behind building a memorable and authentic brand. In this Upshots episode, John shares his approach to harnessing the core ideas of founders and key team member to create a brand that resonates deeply with both its creators and its audience.

"A brand is the sum total of everything you do, everything you make, everything you say, everything you put out into the world. And it takes a while to shape that." - John Cantwell

PDF cheat sheet @ bit.ly/upshotscantwell

Connect with John on LinkedIn, check out his work at g-w.studio, and his most recent project itsdandi.com.

Follow Unserious in your podcast app, at unserious.com, and on Instagram and Threads at @unserious.fun.

Episode Transcript

Speaker 1 (00:19):
This is Unserious you can start using right away.
Our guest today is JohnCantwell, a creative director
focused on brand and copy forearly stage companies.
Happy Monday, John.
What's the big idea for thisweek?

Speaker 2 (00:32):
Hey, micah, happy Monday.
We are going to talk aboutbranding your startup.

Speaker 1 (00:37):
That sounds like a good creative conversation.
Who is this for?

Speaker 2 (00:40):
Well, first, obviously, it's founders.
When you're a founder of anearly stage company, thinking
about brand, thinking aboutbranding, is one of your very
earliest considerations.
Second, creatives.
I myself am a creative.
I have a background as acopywriter.
Now I'm a creative director,and what I have found through
the years is that the way thatyou work with a really early

(01:02):
stage company is very differentthan the way that you would work
with a really large company, amuch more established brand.

Speaker 1 (01:09):
So I think we all have a handle on why branding is
important at this stage.
Why is focusing on startupbranding so important right now?

Speaker 2 (01:16):
This is a really tough, interesting, challenging
time for early stage companies.
You have a bunch of differentthings happening all at once and
they're related to each other.
On the one hand, you have allof the AI companies coming
around and there's so much noisearound AI, and so in that world
, then you have to do the hardwork of figuring out how do you

(01:36):
communicate value.
And then I think the secondthing is it's just a
tremendously challengingenvironment for most early stage
companies right now.
They are being held to a much,much higher standard than they
ever have been historically interms of revenue, in terms of
growth rate and the way thatthey allocate their dollars.
On the one hand, investing inyour brand can be a fairly

(01:57):
expensive thing.
It may not deliver immediateROIs, but at the same time, it
can be a really, really, reallyvaluable accelerant to things
that matter, a lot likeaccelerating your GTM efforts,
helping you get to productmarket fit and product language
fit faster.
Hiring great people yeah, andit doesn't mean you're going to
be that stuff forever.

(02:18):
Your customers are going tochange and you'll need to adapt
accordingly, but not having tostart every communication with
the same question of like, whatare we?
What are we saying?
It saves a lot of effort andjust lets you start kind of
putting things out into theworld and seeing what's
resonating faster, which isgreat.
The most important thing.

Speaker 1 (02:36):
Yeah Well, why don't you walk us through your
approach to branding yourstartup?

Speaker 2 (02:42):
I've been working with early stage companies for
about five years.
I've done it working in-houseas an embedded fractional
creative director, and then I'vealso done it in an agency
capacity.
And before I get into it, Iwant to say I am talking more
about building a brandfoundation from a language
standpoint, thinking about yourmission, thinking about your
vision, thinking about a brandidea, thinking about your brand

(03:06):
promise.
So the very first thing that wedo is a fixed set of questions
that we ask, and the questionsare strategic, of course, but
really what we're trying to dois get a brain dump from the
founders, from the leaders ofthe company, the marketing
people, the folks that live itevery day, because what I found
is that a lot of the ideas arejust in their head and it is

(03:30):
really useful to just get themto sit down and put it on paper.
That is a really usefulexercise.

Speaker 1 (03:38):
What kinds of questions are you asking?

Speaker 2 (03:40):
How would you define your mission?
How would you define your, yourvision?
Um, how would you define youroffering?
How would you define yourcompetitors?
A lot of times, uh, when you'retalking to very especially, very
early stage companies, their,their nearest competitors, or
other companies that are at thatstage, or at least that's how
they think of themselves but thethe reality is that is not how

(04:02):
a potential customer views thelandscape.
They're not looking at you andthe four other seed stage
companies.
They're thinking about theirworld, their lived experience
and what they're trying to getout of work, their life,
whatever.
And then there are somequestions that are a little bit
more, I would say, emotional innature.
And then, there, there are somequestions that are a little bit
more, I would say, uh,emotional in nature.

(04:22):
And it's not like you know,it's not therapy, it's not
telling me about your dad, butyou do.
You do want to get a sense.
You do want to get a sense ofthe overall personality of the
people involved, because,especially at the really, really
early stages, these companiesare reflections of their
founders.
It's so personal and you wantto build a brand and a brand

(04:47):
story that, at the end of theday, feels authentic to the
people that are going to beusing it.
If it's not, if it's not rightand not authentic to the people
that are going to use it,they're not going to use it.
Yeah, they're going to throw itaway.
They'll sniff it out, yeah.
Yeah, use it or lose it.
Yeah, if you don't use yourbrand, um, it will never do the
things that you want to do.
That's sort of one of the thesilent killers of brands is when

(05:09):
people feel like stuff isn'tworking.
Then you start to resent thebrand rather than evolving it so
that it can continue to changeor they do their own thing.

Speaker 1 (05:18):
How many, how many pitch decks have you seen?
That deviated pretty far fromwhat was provided by the brand
team.

Speaker 2 (05:24):
Folks go rogue, you know I mean, and I think even
with that you have to have adegree of humility too, because
you know, say, a sales team,they're doing prospecting with
10 people a day and they got tobe banging out these sales decks
.
You can't expect them to do itthe way your best, most designed
deck is going to be.
Yeah, has to work.

(05:46):
Yeah, you can make the bestbrand guide in the world, but if
folks don't feel A like theyunderstand how to use it and B
feel excited to use it, sure,it's just going to be wasted.
Ooh, that's good.

Speaker 1 (05:59):
Yeah, All right.
So we're asking some strategicand emotional questions here.
What's next?

Speaker 2 (06:08):
I pretty much jumped right into starting to build out
the brand book and mission,vision, brand positioning
statement, boilerplate, a brandpromise statement, sometimes a
manifesto, which I call businesspoems.
If it feels appropriate, I tryto move very quickly on that and
get to a B1 draft as fast asthe schedule allows, basically

(06:30):
so that I can get it in front ofthe people on the team.
I want them to then havesomething to respond to very
quickly so that we can starttalking about things tangibly
rather than an abstract term.
Okay, so I'll do one last passat the brand guide.
And there you go.
Now you have a pretty goodpackage of materials that can
help you kind of live as a brand.

Speaker 1 (06:51):
And to your point about keeping momentum and
moving it along quickly.
I mean, people get excited.
I'm always excited when I seethose first mission statements
and some copy and the firstversion of the website.
It starts to feel real and thatgets me more excited about
participating in it.

Speaker 2 (07:08):
It starts to feel real, which is very important.
The risks are real, but none ofthem are insurmountable.
That's the good news.
If you are building a startup,you are not going to be the most

(07:29):
objective observer of yourcompany, so it's really useful
to get an outside perspective.
And what about expert advice?
I hesitate to call myself anexpert.
You did, I did, thank you, so Istill haven't done it.
I remain hesitant, but I havedone this a lot and I think be

(07:53):
humble.
There is oftentimes a reallysignificant gulf between how
much you care about your companyand how much everyone else in
the world cares about yourcompany, and it's going to take
a long time to bridge that gapand to get other people excited.
So a brand, at the end of theday, is the sum total of
everything you do, everythingyou make, everything you say,

(08:15):
everything you put out into theworld, and it takes a while to
shape that.
This is a long tail game, forsure.

Speaker 1 (08:22):
Well, this is really great stuff and, you know, on
serious still, being an earlystage startup by that definition
, really timely for us as well.
So thank you for being on today.

Speaker 2 (08:32):
Appreciate it.
Thank you, it was great talkingto you, micah, for being on
today.

Speaker 1 (08:37):
Appreciate it.
Thank you, it was great talkingto you, Micah.
You can connect with John onLinkedIn and check out his brand
identity work at g-wstudio.
That studio is a suffix nowCrazy.
His newest project is an AIworkforce intelligence platform
called Dandy, which you cancheck out at itsdandycom.
In the show notes we'll have alink to the PDF cheat sheet that

(08:58):
accompanies every Upshotsepisode.
This podcast is brought to youby Unserious Group.
We're a communications andstrategic consulting practice
that helps companies and leadersnavigate the rapidly changing
workplace by lowering the stakesand working more efficiently,
playfully and creatively, and weare open for business.
So check out unseriouscom andlet's be work friends.

(09:19):
At Unserious, we make work play.