Running an Agency Is a Team Sport (And Most Founders Build the Team Backwards)
Interview: Travis Caldwell on focus, differentiation, hiring for culture, and why “everyone sells”
Haus Advisors Live with Travis Caldwell (Agency operator, former marketing leader/CEO, 15+ years in agencies)
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Prefer the highlights? Key takeaways and summary below.
TL;DR – Key Takeaways
A super common agency trap: trying to be everything to everyone, which spreads your team thin and kills delivery quality.
In dev agencies especially, letting clients dictate your tech stack can leave you supporting a dozen stacks and burning your team out.
Differentiation usually isn’t the tool or the output — it’s your approach to solving problems (how you think + how you work).
“Everyone is in sales” doesn’t mean everyone cold DMs people. It means everyone can help create growth through referrals, relationships, and reputation.
If you’re starting (or restarting) an agency, have a 1-, 3-, and 5-year plan so you don’t build a messy business by accident.
Hiring is less about skill (you can train) and more about culture + emotional intelligence (harder to teach).
Ops lesson that hits hard: producers need protected focus time. If you plan for 6–7 billable hours/day and then add meetings, you’re basically planning burnout.
Meet the Guest
Travis Caldwell has spent 15+ years in agency life across marketing and custom web development. He’s worked in ops, delivery, and leadership — all the way up to CEO.
Right now, he’s exploring launching an agency/services business that supports agencies, especially those in the 10–15 person range, with operations, forecasting/finance, delivery, and people systems.
Episode Summary
1. How Travis got into agencies (and why he stayed)
Travis came up through the marketing track — starting in e-commerce, then email marketing, including an early role at Zulily (startup intensity included), then nonprofits, and eventually into agency life.
His first agency “real” experience was at Vermilion in Boulder, where he helped build out the digital marketing practice. That meant doing a little bit of everything (PPC, email, social), managing a bunch of clients, and learning what it means to be billable — where deadlines actually matter because clients are paying.
That was the hook for him. He fell in love with the agency ecosystem.
2. The most common mistake: “Sure, we can do that.”
Travis didn’t call out any single “we totally screwed this up” moment, but he did name a pattern he sees all the time — especially in smaller, founder-led shops:
They take whatever work walks in the door.
And in dev agencies, that turns into a nightmare fast:
If the market dictates your tools, you end up with a dozen different stacks across clients, and suddenly you’re maintaining everything forever while your team gets stretched thin.
His point wasn’t “pick a vertical or die.”
It was simpler: know what your core strength is, and have the self-control to protect it — even when a dream client shows up.
(He basically said: if Nike walks in… you’re probably going to try to make it work. Which is exactly why this is hard.)
3. Differentiation is usually your approach, not your output
This was one of the more grounded takes on differentiation:
In agencies, we’re all solving problems.
The “thing” we deliver can become a commodity.
But your approach — how you think, how you run discovery, how you reduce risk, how you communicate, how you implement — that’s the differentiator.
He gave a great example from his prior world:
Bear Group’s founder had a clear why: bringing CMS capability to non-enterprise clients through open-source tech. That clarity kept the company anchored as the world shifted.
4. If you started over today: be intentional early
Travis’s advice to his past self wasn’t “get a better logo” or “buy business cards.”
It was: stop winging it.
Have a 1-year goal, a 3-year goal, and a 5-year goal so you don’t wake up with an 8-person agency you “didn’t mean to build,” doing random work for random clients, while you’re stuck learning HR tools instead of doing the craft you’re actually good at.
And I liked how you (David) tied it back:
A vision makes you more proactive. Without one, you’ll accept bad-fit work to keep the lights on… and then five years later you’re paying the price.
5. New business: everything works and nothing works
Travis’s take on growth was refreshingly honest:
Agency growth is weird. It’s not DTC. It’s not clean B2B SaaS.
Attribution is messy and delayed.
Sometimes you run an email campaign and the payoff comes two years later. Sometimes a great client leaves, joins another company, and comes back around later. It’s long-game stuff layered with short-game needs.
He referenced the classic paid / owned / earned model as a helpful frame — but also called out that it’s messy because things like partnerships can overlap all three.
His “conviction” was basically:
What you put time and energy behind tends to work.
If you starve a channel, it dies. If you invest, you’ll usually see reciprocity and momentum.
He also called out macro realities (like election years) slowing down decisions — and the need to adjust strategy accordingly (lean harder into relationships, referrals, upsells when net-new is harder).
6. Hiring: culture fit is the real gate
Travis is very “culture first,” and he explained how he made it real:
He loved being the first call candidates had (even as CEO), because it set the tone and helped assess fit early.
Skill can be trained. Emotional intelligence is much harder to teach.
Candidates are interviewing the company too — and if it’s not a fit, you want to learn that fast.
To make culture fit less “vibes only,” he used:
core values-based questions (one question per core value)
scenario questions about communication and conflict
EQ assessments to get another signal alongside gut feel
7. Ops: stop planning burnout into your delivery model
This one is worth repeating because it’s so common:
If you plan for 6–7 billable hours/day and then stack 2–3 hours of meetings… you didn’t “get busy.”
You set that person up to fail.
His point: protect maker time. Sometimes the best work happens after a walk, not in another Zoom.
He compared agency ops to a sports team:
Everyone’s a “player,” but they have different positions and strengths. You don’t move a great left fielder to first base just because you’re short on first basemen — and you don’t need three first basemen.
Ops is putting the right people in the right seats so they can win.
Notable Quotes
“Custom web development… you can write code a lot of different ways… and you can stretch your team super thin.”
“By and large… it is your approach that is the differentiator.”
“Everyone’s a salesperson in agency life.”
“If we stack in 2 hours of meetings… that’s how you end up with burnout.”
Learn More / Get in Touch
Want to connect with Travis?
He said the easiest place is LinkedIn — search Travis Caldwell and message him there.
He’s also exploring a new offering to support agencies (especially around 10–15 people) with:
operations
forecasting + finance
delivery
people systems / professional development
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