Episode 39: How to Stay Relevant When Your Tech Stack Gets Commoditized

Positioning & Differentiation

Nov 12

Written By David Hoos

Behind the Agency Podcast with Hunter Jensen, Founder of Barefoot Solutions

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Prefer the highlights? Key takeaways and summary below.

TL;DR – Key Takeaways

Hunter started as a self-taught dev, freelancing off Craigslist, then built an agency when he realized hours cap out.
Barefoot’s motto: “Lean into the hard stuff” (regulated, complex, high-stakes builds).
They’ve stayed relevant by riding 3–4 year tech waves: web → mobile → IoT/medical → blockchain → ML/AI.
Hunter’s big idea: agencies stay relevant by either specializing or staying ahead of the next wave (Barefoot chose the second).
AI is opening a brand-new market: “traditional businesses” that never would’ve bought custom software before.
Practical AI wedge questions Hunter uses with CEOs:
- “What would be valuable if you could predict it?”
- “What paper-pushing could we automate now that LLMs exist?”
Pipeline shift: cold outbound worked great in 2020–2022… then got flooded and stopped working.
New growth engines that are working: in-person speaking, newsletter-driven small offers, AI-powered personalization, and referrals.

Does This Sound Familiar?

The work you built the shop on keeps getting cheaper. Clients who used to need a custom build can buy a platform now, and the ones who still call you want the same thing for less than last year.

You can feel the floor moving. What's harder is knowing whether to go narrower, go upmarket, or go somewhere new entirely.

Hunter Jensen has made that call four or five times. Barefoot has ridden web, then mobile, then connected devices and medical, then blockchain, then machine learning, and he says the waves run about 3 to 4 years apart.

So his motto is to lean into the hard stuff. Regulated work, complex work, high-stakes builds that don't get cheap quickly.

His framing of the choice is the useful part. An agency stays relevant one of two ways: specialize deeply, or stay ahead of the next wave. Barefoot picked the second, and he's candid that it's the more demanding of the two.

Now, he's also straight about what stopped working. Cold outbound was excellent in 2020 through 2022 and then the channel flooded. What's replaced it is speaking in person, a newsletter feeding small paid offers, and referrals.

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Meet the Guest

Hunter Jensen is the Founder of Barefoot Solutions, a custom software shop based in San Diego. They build complex, data-driven applications — especially in regulated or high-complexity environments (think SEC/FDA-level constraints).

Barefoot has worked across enterprise, startups, and mid-market, with recognizable names like Microsoft, Salesforce, Cisco, and projects like the IMAX website.

More recently, they’ve been deep in machine learning, predictive analytics, and generative AI, and Hunter spends a lot of time speaking, writing, and tinkering to stay ahead of the curve.

Episode Summary

1. From Craigslist PHP gigs to a real agency

Hunter’s origin story is classic “builder brain.”

He dropped out of a computer science program because it wasn’t teaching what he wanted (the internet was moving faster than the curriculum). So he went self-serve: library books + web programming + Craigslist gigs.

That paid tuition. Then after graduation he moved to San Diego, freelanced, had fun… and then had the moment most freelancers eventually have:

You can’t scale hours.

That realization pushed him into building a real business.

2. The main tension: generalist agencies get commoditized

Hunter laid it out pretty bluntly:

If you’re a generalist shop and you don’t evolve, you get eaten alive by:

cheaper competitors
DIY tools
the market’s “good enough” options

So Barefoot made a choice that a lot of agencies say they want… but don’t actually commit to:

They stayed generalist but kept relevance by always moving toward what’s next.

3. Their unique way of solving it: “stay ahead of the wave”

Hunter sees two viable strategies for agencies:

Specialize (vertical or tech stack) and become the known expert
Stay ahead of new tech waves so you’re always in demand before it becomes normal

Barefoot chose #2.

And the key detail: staying ahead includes doing internal “bleeding edge” work that doesn’t make money right away, just so they’re positioned when the market hits the inflection point.

He described a predictable cycle:

There’s a “world wakes up” moment (example: App Store launch)
Then comes an education/strategy phase (“What’s our mobile strategy?” / “What’s our AI strategy?”)
Then the wallets open and big implementation projects happen

He believes we’re moving out of the “AI proof-of-concept phase” and into the “real budgets, real projects” phase.

4. Two questions that get a CEO interested in AI

Hunter shared a few models that are super usable:

A) The “Two CEO Triggers” (for selling AI to normal businesses)

He asks CEOs questions that spark ideas instead of overwhelming them with tech talk:

“What would be valuable if you could predict it? (and do you have historical data?)”
“What paper-heavy process could we automate now that LLMs can reliably extract and transform info?”

It’s basically: “Where are you still doing 2020 work with 2026 tools?”

B) The “3-case-study rule” (for repositioning)

They don’t fully shift messaging until they have real proof.

Hunter likes to have 3 solid case studies in the new area before they overhaul brand and positioning around it.

That’s smart, because it avoids the trap of branding yourself as “the AI agency” before you’ve actually shipped AI work.

C) The “inflection-point positioning” play

Barefoot updates:

website / messaging
content strategy
forward-facing positioning

…right when they’ve got proof and the market is starting to care.

5. Cold outbound worked until 2020, then the channel flooded

Hunter’s not afraid to say the quiet part out loud:

Cold outbound used to work. Then it got saturated post-2020 when everyone moved online.

They tried turning every knob and dial… and it still didn’t work like it used to.

His theory: digital channels got flooded, and it’s insanely hard to get above the noise.

So they’re leaning into what’s working now:

in-person speaking (especially CEO groups)
and smarter “small offers” instead of asking strangers for marriage on the first date

6. Founder energy opens the door on a new wave, then the team runs it

This part was subtle but important:

Hunter personally gets heavily involved in the first few projects in a new technology wave.

Why?

to close them
to make sure execution is solid
to create the proof needed for the next stage (case studies + positioning)

After that, the team can run it.

Founder energy is used like a battering ram to open a new door — not to carry the whole business forever.

7. Why big deals never start with a Google search

Two big things stood out:

Barefoot leans on referrals heavily because when the deal size gets big, nobody “just Googles a dev shop.”
Hunter has leverage most boutique firms don’t: he sold controlling interest in 2019, and now has access to a parent company with ~1,500 engineers, which makes experimentation faster and lets them do highly technical lead-gen projects.

He gave a killer example:

They helped a marketing agency target plaintiff class action attorneys by pulling attorney info out of lawsuit filings (buried in huge PDFs) and generating personalized outreach at scale. The client had them turn it off after a week because they got too much business.

That’s the theme again: new tech turns “intern work” into automation.