Retainers Beat Rollercoasters: How a Video Agency Scaled Profitably (Without Losing Its Soul)
Interview: Kyle Bush on Scaling a Video Agency with Profit, Process, and “Make It Cool to Care” Culture
Behind the Agency Podcast with Kyle Bush, Founder & CEO of Cumberland Creative (Nashville-based video production agency)
Watch
Prefer the highlights? Key takeaways and summary below.
TL;DR – Key Takeaways
Kyle didn’t “dream of owning an agency.” He fell into it through skate videos → business dev → jump ship in 7 days.
Their early edge was simple but rare: one partner sells + runs the business, the other delivers. That breaks the feast/famine loop.
They scaled headcount based on retainer revenue, not big project spikes. Freelancers absorbed the project swings.
A painful lesson: when a key contact changes, treat it like a brand-new client. Rebuild trust from zero.
Another lesson: never respond emotionally (especially about contracts). Cool off, check facts, then reply.
Video is naturally project-based, but Kyle believes retainers are less stressful and more “build-a-real-business” friendly.
Their value prop: trim the fat, obsess over client experience, and make budgets go further.
Hiring: early on, hire for character, teach skills. Later, you need character + skills (harder).
Culture stopped being cheesy when they implemented an operating system + values and actually enforced them.
Kyle rejects the “agencies can’t be profitable” mindset. He thinks stability and a good lifestyle are totally possible.
Meet the Guest
Kyle Bush is the founder and CEO of Cumberland Creative, a Nashville-based video production agency.
His story starts in a place you don’t hear every day: skateboarding. In skate culture, videos are everything. Kyle started filming skate videos as a kid, fell in love with the craft, then later stumbled into agency life through a Lyft passenger connection that landed him an internship at a top Nashville ad agency.
From there, he ended up in business development at a video company, saw the writing on the wall, and… launched Cumberland Creative within 7 days.
Episode Summary
1. From skate videos to “oh… this can be a career”
Kyle’s path wasn’t “I want to be a founder.” It was more like:
loved making skate videos
got older, kept the video obsession
felt trapped by the idea of office life
got a lucky connection into an agency internship
saw video shoots happening in a professional setting
light bulb: this is a real career
That’s a pattern I see a lot: people don’t pick the agency world… the agency world kind of recruits them.
2. The 7-day jump: why they could pull it off
They weren’t starting from scratch skill-wise. Kyle could sell and concept. His partner could direct, shoot, and edit. They already had a working rhythm from the previous company.
They also had a clear early rule:
“We’re going to stay busy—even if we’re working for free.”
And a second rule that a lot of creatives don’t internalize until pain forces it:
“We’re going to be profitable and scale profitably.”
Kyle mentioned reading Rich Dad Poor Dad around that time, and it shaped their mindset.
3. How they avoided the classic agency feast/famine trap
This is one of the most practical parts of the convo.
They only grew overhead and headcount based on retainer revenue, not project revenue.
Retainers = the “bedrock”
Projects = bonus volume
Freelancers = elasticity to handle spikes
That meant they could sell strategically without panic. No “we just landed a big project, hire fast” followed by “oh no, it ended, layoffs.”
Analogy: It’s like only signing a lease you can afford on your salary, not on your best month’s commission check.
4. A mistake that still haunts him (and the fix is useful for everyone)
Kyle lost his favorite client after a marketing director change—not because the work got worse, but because he treated it like “business as usual.”
Two lessons:
When a key stakeholder changes, treat it like a new client. Re-onboard them. Re-earn trust.
Never respond while you’re emotionally lit up. He replied quickly, assumed contract terms without checking, and it rubbed the new director the wrong way.
That part hit because it’s so human. Everyone’s “professional” until it’s their favorite client and the email lands at the wrong moment.
5. Value prop: trim the fat + obsess over client experience
Kyle’s take on the video production industry is blunt: there’s a lot of ego and fluff.
Cumberland Creative tries to win by:
giving “white glove” service
taking stress off the client
making the budget go further
cutting the BS out of production
Their current positioning line (his words, basically):
“the only production partner obsessed with our client experience and success.”
6. Retainers in a project-based industry: two viable paths
Kyle laid out the two roads video agencies tend to take:
Path A: high-end project-based production house
small core team
scale up with contractors per shoot
less overhead
can be very profitable
but often harder to “step away” / less sellable as an owner-agnostic business
Path B: retainer-based production partner
package ongoing content needs
build a team + leadership structure
more predictable revenue
less stressful
typically aimed at companies with recurring content needs (not Super Bowl ad buyers)
Kyle’s opinion: for most agencies in the $500k–$2M range, trying to survive purely project-based can be brutal unless you’re already “world class” with constant inbound.
7. Sales and marketing: relationships still win, inbound isn’t enough
Kyle is honest here: they’ve been strong at sales, less confident in marketing.
What worked:
trade shows
niche networking
proactive outreach with creative ideas
“more hands you shake, more deals you make”
They also ran PPC/Google Ads successfully around 2018–2019, but saw performance dip more recently (he mentioned changes tied to Google’s AI shift).
Big takeaway: even when inbound worked, it still wasn’t enough to carry the whole pipeline. Their engine is mostly:
repeat customers
referrals
8. Hiring and retention: character first, then level up to character + skill
Kyle’s approach early was:
hire from people you know
clients, freelancers, interns
hire for character, teach skills
They’ve had low churn, but he’s now feeling the next-level challenge:
you eventually need both the right character and the right skill set
recruiting becomes a real craft
Retention comes down to culture—and he gave a great example: culture changed when they implemented an operating system, mission/vision/values, and held people accountable to it.
He referenced Unreasonable Hospitality and the idea of:
“Make it cool to care.”
And crucially: don’t just say values—hire and fire by them.
9. The contrarian mindset Kyle rejects
This was one of my favorite endings. Kyle basically said:
A lot of agency owners normalize break-even survival like it’s the best you can do.
He rejects that completely.
He believes you can build an agency that:
makes real profit
supports a good lifestyle
isn’t soul-sucking
and still does great work
I’m with him on that. “This business is supposed to be miserable” is one of the most damaging stories agencies tell themselves.
Notable Quotes
“Treat them like a new client and start the process from ground zero.”
“Never respond to a situation whenever there’s heightened emotion.”
“We only grew headcount and expenses based on what retainer revenue could cover.”
“Make it cool to care.”
“I wholeheartedly reject the mindset that creative agencies can’t be profitable.”
Learn More / Get in Touch
Email → kyle@cumberlandcreative.co (note: spelled from audio; double-check before publishing)
Cumberland Creative → (search “Cumberland Creative Nashville”)
Kyle also mentioned he’s building:
a community for video agency owners
coaching for video agencies in the $500k–$2M range
Want More Interviews Like This?
Subscribe to the show on [YouTube link]
Join my newsletter for weekly insights → [Newsletter link]
