Agency Journey

Ross Crooks is one of the Co-founders of Column Five, a creative agency specializing in brand development and storytelling. There, he oversees creative operations, working with a group of wonderful humans to deliver for some of the most forward-looking companies around today. He is passionate about building a thriving culture based on transparency, trust, and having a good time.

Show Notes

Topics discussed in the episode:
  • The Importance of Crafting a Content Strategy
  • Marketing Content Strategy Best Practices shared by Ross Crooks
  • The Evolution of Column Five's Content Strategy
  • Career Opportunities with Column Five
Resources mentioned in this episode:

What is Agency Journey?

How do world-class agencies continue to grow profitably and hit their goals, even through the choppy waters and challenges of agency life?

How do leaders like Tiffany Sauder, Marcus Sheridan, Jay Acunzo, Shama Hyder, David C. Baker, Nikole Rose, and Zeb Evans think?

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Each episode focuses on crucial aspects of growing an agency like building the right team, delegation, project management, client success and retention, and operating frameworks like EOS.

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All right.
Welcome back to Agency Journey this week.

I've got the pleasure of bringing
on Ross Crooks from column five.

Column fivemedia.
Com.

Ross, thanks for making
time and joining me today.

Yeah.
Thanks for having me.

I appreciate it.

So we got a chance to
meet earlier this year.

You got a really cool story.

And I want to dig into a couple of

similarities in your journey and
some of what we've been through.

But first, could you give us maybe 32nd

minute long kind of overview of column
five and your role at column five?

Yeah, sure.

So column five is a creative agency.

We do a lot of
marketing work for brands, and in more

recent years, that means
kind of working with them from anywhere in

the brand strategy, content strategy
and then into content production.

So we've done a lot of creative content

production in a variety of forms
over the years.

And our client base looks like
a lot of tech brands, but we have a pretty

diverse array of clients in education
and nonprofit space as well.

So it's spread around quite a bit.

And then my role with the company.

I'm a co founder.

I have two partners that I started

qualified with about twelve years ago, and
I oversee our creative teams and our kind

of operations teams were there three
cofounders when you started as well.

That's kind of a trick question.

There were five originally, but we

actually sort of separated from
the other two pretty early on.

So it's been three for most of the ride.
We started.

Andrew, my current business partner.

He and I, along with two other good

friends out of our College dorm room
back in 2011, started our first agency.

I went and met with a friend.
Totally different.

He's a big pole barn builder, so totally

different industry and had lunch
with him like my senior year.

And he said, So you're
starting a business.

How many founders?

I said four.

He's like a year from now when we're

talking, there's not
going to be four of you.

I was like a rude thing to say.
It never works out.

Don't take it personally when it happens,

you guys probably won't be in
business together for the whole time.

A couple of years later, it was the
two of us still great relationship.

It's just hard to get.

A business is a big undertaking,
and not everyone is a fit.

And you don't know all
that stuff going in.

Yes, it really has to be kind of a perfect
balance of equal contribution and

skill sets that work well together and
personalities that work well together.

Right.

We still give each other a hard
time about ownership jokes.

It's classic.

So I was doing some digging
through some of your background.

This theme of, like, data design
or data visualization came up.

You are an author.

We didn't mention that at all, but
you've written a book on infographics.

You started a software that looks
like it was around infographics.

Where did that focus?

Maybe tell us a little bit, I guess, set

the stage on what that
background looks like.

But where does that come from?
Yeah.

Good question.

It's a bit of a long story and
a little bit of an accident.

But what happened, essentially, was

my cofounders and I were all kind
of working in different businesses.

We were all working in
the clothing industry.

I had started a clothing recommends
clothing brand

with one of my partners, and our other
partner was doing the clothing boutique.

And so we're all kind of working together

in the space, trying to make
our first companies work.

And
we started a blog that was sort of like an

art, music, fashion, lifestyle type blog
to be able to cross promote

our own brands, but also, like, bring
partners in and build relationships.

And that sort of thing if you only create

something of value, basically
through sharing and giving media.

And as we got into that and started

creating content for this thing,
we started to get pretty good at creating

and promoting content and getting
it popular, having to go viral.

And that sort of thing,
this is like 2007 2008.

And what happened is a lot of brands
started to see us have success in that.

And some of the early startups that we're
getting into kind of content marketing and

trying to stretch their
marketing dollars a little bit further.

And so they started hitting us up to

create and promote
content for their blogs.

So Mint dot com was a really early one

that was a client of ours that was
kind of a startup at the time.

And we started creating content for them.

And how the data visualization and
infographics focus came was really what

was happening is we were creating,
promoting content and a lot of the social

news sites at the time, which
was like the Redditbid.

Com stumble upon.

And what we were seeing was a lot of
people

really geeking out on old infographics,
like scanning them out encyclopedias,

looking at them in old
newspaper clippings.

But no one was really creating new,
contemporary infographics outside of, like

a few news outlets, like The New
York Times at a very high level.

So as we were writing articles for these
startups, we started to kind of piece

together, hey, we can use this data from
these startups and visualize it

and use contemporary kind of graphic
design to make a more visual artifact.

And that was kind of how we made a name

for ourselves was in kind
of pioneering those common.

Now it's kind of a mainstay in the
marketing ecosystem, but it's kind of

long, skinny blog infographics
kind of develop organically like that.

That's wild.

Remember Noah Kagan, was it meant back in
the day right before our time, I guess.

Okay.
And that's kind of a wilderness.

At what point then does the
agency become, like, was that.

Did you just get enough traction on that

side that that was the evolution
of, hey, we want to start.

We might as well do this for now
as an agency or what's the story?

We were just trying to figure out a way to

work together and do something that was
fun and creative and make some money.

And yeah, that started to get traction.

And so we sort of slow over the next year

or so kind of shuttered our other
businesses and develop something together.

And it started growing really quickly.

So we kind of put all the eggs in that
basket and then so you want to building

out a software. But my impression is it's
an infographic generator, right?

Yeah.

Kind of a web based
design tool that was meant for.

Like, Canva for infographics, basically.
Yeah.

I think there are a lot of similar stuff.
Okay.

Makes sense.
And then is that still active?

There are a few clients that we're still

working actively with, but we're not
actively marketing at our selling yet.

Makes sense.
How was that?

I assume at that point, the
agency already had legs.

Was that the I mean, I feel like every
agency goes through at some point in time.

They're like, we're going to
build the software on the side.

We've got these extra development hours

and resources that we
can do and build it out.

And some of them take and some
of them don't take as much.

Yeah, there's a range.

But with the agency, the main thing the

whole time and software was that
side business or what's your yeah.

We started the agency in 2009
and kind of properly started it.

And then
we started incubating the software maybe

in 2012 or 13 and then spun it out into a
separate company

in 13 or 14 and raised some venture
capital or speed ground for it.

And kind of made it split off the company

and made a separate go of
it with a separate team.

And we did that for three or four years.

And
we have a lot of good traction, but didn't

get quite traction that we needed to
have it survived on its own.

And so we ultimately pulled it back into

the agency and kind of
kept focusing on that.

I can 100% relate.

I mean, we a project management tool.

Starting in 2013,
House spun it out as its own business,

took all the best people from the
agency and moved over to the software.

And ultimately, we weren't that good at
software and consulting and had a choice

to make between one or the other and went
down the road that we were better at the

less lucrative path from
evaluation perspective.

It's hard work.
It's competitive area, especially when

you're in something like
project management or market.

It's like just in this
family busy ecosystem.

That's awesome.

And then so for a little while,
you were also teaching at Columbia, and

you were writing and you're building an
agency and you had a fashion manual.

I'll back up.
I'll start with the book here.

What was the journey to say?

Hey, I need to write a book.

And then was it worth
the effort that it took?

Yeah.
Good question.

You make it sound like everything
happened at once, and it kind of did.

It was like, I think 2012 ish, but yeah,
we had the opportunity to

widely approach us book publisher to
write a book on infographics, and we were

kind of the leaders in that space and had
done a lot of thinking around it and

developed more practices
and things like that.

Other people were creating
infographics for sure.

But I think we were the first people to

start to do it at scale
and really commercialize it.

That was like an exciting opportunity for

all of us to be able to put our name on
something and share what we knew and also

a good kind of marketing tool to have to
say that we wrote a book on the topic.

And yeah, I think it was the exact same
week that Columbia University approached

us to write
to do a course on visualization of

information,
so we couldn't really say no to either.

And so we were developing the course
and writing the book at the same time.

And I was on my honeymoon for some of it

and moving into a new office and
building it out and that sort of thing.

So it was a very crazy time.

But I think looking back, certainly,
I think it was worth the time and effort

to be able to write the book and
the experience of teaching as well.

I kind of wish I had more time to dedicate

to it and obviously
thinking of philosophy and all those

things have evolved quite a bit over
the years from those early days.

So I think I'd love to be able to update
it sometime or to do a follow up.

Right.
Well, I wanted to bring it up because

you're saying Wiley approached
us and Columbia approached us.

And then if you go to com fivemedia.

Com for anybody who's looking at the
site, you can see a bunch of logo.

You guys have worked with LinkedIn and
Uber and Netflix and Dropbox, and you've

got all these big
household names in the tech space.

But those connections obviously don't come

to most four year old agencies
or real estate agencies.

Is this largely a product of networking or
I mean, the combination of you guys were

super early on, a trend
that stuck as well.

And so you got a chance to be first
movers and benefit from that advantage.

But
you're saying things that most agency

owners don't get to live through early on
in their career, which is why I wanted to

have you on, because it's
a fascinating story.

Where did those connections come from?

Yeah, I think a lot of it did come from
being kind of a first mover in that space.

So we were able to be found when people
were looking for execution on that.

The other piece was we were working with a

lot of these kind of scrappy
early stage startups.

So as these people got acquired, we kind
of came into their mother company, right.

So into acquired men.

So we work with Turbocharc and we work
with QuickBooks and these sorts of things.

We work with LinkedIn and Microsoft, and

they came together and
GitHub and things like that.

So I think some of that just happened

naturally through this
sort of M and a cycle.

We had a lot of really good clients early
on that we were friends with and that were

really helpful to us and
just making introductions.

And those people went places.

I think a lot of that is just sort of the
organic things that happen when people

move from company to company
and clients acquire each other.

But I think
the nature of our work has always been

pretty visible because early on it was
like the goal was always to go viral.

So we had a lot of that.

And we had contribution, a lot of
our graphics created by column five.

And so a lot of people would find
us through those sorts of things.

And now that that's
shifted away from the novelty of the

format, and it shifted away from being
able to get credit on everything we do.

It's much more about our own
content marketing strategy.

So creating useful resources on our blog
and kind of pulling people into that

the blog outside of being
beautifully designed.

You guys produce a ton of content
on all these different topics.

I definitely recommend looking at the blog

if you're listening for inspiration
as well as the resources themselves.

So that piece hasn't, even though
infographics

they zoomed up in terms of a trend and
then maybe have cooled off a little bit.

The dedication of content hasn't changed

at all, which is cool to see
from the story.

One of the things that a lot of early
stage agencies struggle with agencies in

general struggle with is
like, who's my market?

What are we doing for them? What's the fit
between what we're good at and what the

market needs and how do we get in front of
people?

Was the tech ecosystem? Was that an
intentional decision or was that kind of

an accident of, hey, there are early
adopters, and you guys are early adopters.

I think it was more just
the coincidence of that.

And even over time, we've asked ourselves

the question of, like, do we need to
narrow our focus because we work on

with a lot of different companies, maybe
100 plus companies in any given year, and

those are all across different
industries and vertical.

So I think there tends to be a tech focus
just because those are people that have

pretty well established
digital marketing practices and

so it tends to be a good fit, but we've
never been exclusive in that way.

Right.
That makes sense how scaled out and are

servicing the volume of
clients that you are.

What does that look like?

Scaling client services to
support that kind of growth?

Yeah.
It's always work in progress.

I think

we've been experimenting a lot even this
year just with reorganizing our teams and

working in different ways that
might better serve our clients.

I think that

what I noticed there, I guess, is that
there's always this balance between the

flexibility of staffing, anyone on
anything at any time with the focus of

having a dedicated team that
works really well together and

have clear established ways of
working and that sort of thing.

So there's pluses and
minuses about those things.

And I think we're trying to figure out
what's the balance of the most pro.

Right.

Looking forward, I was just mentioning,
this is a great time to grow.

We're coming up on the fourth and second

quarter of the best growth
across the board for agencies that I've

seen in the last ten years
being in this space.

But staffing for that is
a challenge at the same time.

That's part of where you're spending some

of your time now, but kind of inclusive of
that and other priorities you're looking

forward to what is the
end of 2021 look like?

What does 2022 look like for the agency?

What are some of the big targets
that you guys have as a firm?

Yeah.

I think recruiting has definitely
been a big one for most of this year.

I think coming out of last year, that was
pretty uncertain.

We were sort of hunkered down and just

making do with what we had
and figuring it out.

And then the beginning of the year hit and

felt like we needed to
grow by 25% overnight.

And so that's been a longer than usual
cycle to get new people in the door.

But we've just had maybe five or six new
people start in the last month or so,

which is really exciting to have some
new faces and to be growing again.

I think what that looks like is
we're really trying to

I think we've been behind in some of the
things that we've been doing just because

we haven't had the staff to be able to be
really Proactive in some of those ways.

So I think it's getting more intentional
and more Proactive with each of our

clients to be able to look forward
into what needs are not being met.

What opportunities are there to grow with

those people now that we
have the capacity to do it?

And one of our big focuses and sort of one
of our this might be going back to your

other question about the evolution, as
well as one of the more intentional shifts

that we've made in the last couple of
years was to start to move upstream from

just a lot of creative content
production into the strategy realm.

And so we've really built out that

practice and those roles on our team
to be able to build the foundation that's

needed to create content and any marketing
down the road, any sort of communication

and understanding at the core of the
brand, what's their sort of

purpose and values, and then
flowing that into a strong content

strategy and then being able to
actually create content for them.

So
some of the roles that we're hiring for

right now, we're hiring a
couple of strategist roles.

We're hiring for a new account director or

maybe two and a new
video producer as well.

So

what is that when you say staffing up and
kind of going upstream

and you mentioned Strategist roles, I'm
assuming that that's maybe strategy roles.

What's the correlation or how
is you guys are scaling up?

How does that set up from an
org chart perspective, I guess.

Do you have because typically, you'll see,

like an account manager or Strategist is
kind of lead of X many accounts, and they

either working in pods or shared
resources underneath them.

But you mentioned account directors.

So is a strategist working across
more accounts to your accounts.

What's an account director's role? How do
you kind of break down those distinctions?

Yeah.

Our account directors are kind of

responsible for growth
in the relationship.

So they're maintaining the relationship

and doing some planning and
budgeting and things like that.

But they're also really responsible for

finding new opportunities and
understanding what else client I need.

Our strategies are really focused on

actually just building out the
strategy in any given engagement.

So understanding

where a brand is at the time, what gaps
might need to be filled in their strategy

and being able to do the research
and make recommendations on that.

But then we can go and kind of execute on
downstream and who coordinates an

execution, usually a
producer role on our team.

So that's sort of our
creative project manager.

It looks a little bit different
on different work types.

Some people are very tactical project
manager, and some are

getting much more into the creative
and helping to guide the team in that.

But, yeah, they kind of help run the show.
That's awesome.

Ross.
I'll look this up real quickly.

The careers page.

I'm trying to remember, but I think

there's a link from the footer that takes
you to the careers page on the site.

Yeah.
Column five.

Comjobs.
Cool.

Okay.
That's even easier.

Awesome.

So if anyone's interested in opportunities
with column five actually just saw

one person who you just hired
is from Erie, Pennsylvania.

Yeah.
So that's where I grew up.

I think we just hired two
Pennsylvania people.

Okay.

We're infiltrating column five.

So that's really happening.

That's awesome.

Well, this has been really fun to
dig into the column five story.

I think as you look at

kind of closing out this year, one
question I've just started asking people,

I did not prepare you for this at all,
but this is just kind of a fun question.

Is around kind of year end

expenses or like write offs
running to a lot of agencies.

This has come up a handful of times here
recently in conversations, folks, I have

made more money than I've
ever made this year.

Where are we running off? Do you have any

fun end of year write offs that you'll
be paying for this year or past stories?

I don't think so.

Usually it's a balance because we have

clients that are trying to
get rid of their budgets.

But sometimes we're playing the bank in

that where we might
take it on the nose from the tax bill.

But we'll take your money and
work through next year, right?

But, yes, sometimes we're also trying

to cash the checks until the
first of the year, for sure.

Yeah.
Nothing big.

We started doing a little more

just in terms of we just got
everyone their own credit card.

So we're having a lot more

kind of put a lot more toward kind of
connection and communication events.

So a lot of times
we'll all order lunch from our own

respective places while we do our town
hall meeting, or

we'll have different celebratory type
events where everyone can just kind of

spend their own meal budget
or that sort of thing.

That's cool.

I'm obviously a tool nerd. Are you guys
using do you run your credit card through

Brexit through Ramp or are
you using something else?

We're using Divi Divi.
Okay.

Yeah.

We just switched over to them
earlier this year.

Makes sense.
That's awesome.

It's been cool to see that just the

business credit card space
changed the last couple of years.

It was like Brex kind of burst on the
scene, and then all of a sudden, Debbie

was the next big one, and Ramp is just
raising absurd amount of money right now.

So interesting to watch that space evolve.

Yes, it definitely seems like a

good evolution because I think it's been
messy for a while or a hard thing to do.

That's awesome, Ross. For folks who want
to connect with you or follow you online

outside of the column five site, is there
anywhere else we should point people?

I don't think so.

I'm not active early on social media,

which is strange for a
person in my position, but.

That.

I have a couple of accounts, but don't use
much, but everything's really through.

It's kind of my focus.
Awesome.

Cool.
We'll make sure all that stuff is in the

show notes, but I
appreciate you coming on.

Being generous with your time.
This is a fun conversation.

Thanks, Ross.
Thanks, Gray.

Appreciate it.
Bye.