· NEWSLETTER ·
#78
The Brand Mistake That Costs You Customers
June 2, 2026 · 4 min read

Happy Tuesday! This week I sat down with Chris Willow, founder of Wayfront (which thousands of agencies might know better by its old name, SPP / Service Provider Pro).

Wayfront has been used to sell over $500 million in agency services, and just went through its own rebrand.

Hits a little close to home for us, given we did the exact same thing a few weeks back.

In this episode, we covered why agencies should productize one thing until $1M, why brand advertising is wildly underlooked in 2026, and the one ingredient nobody talks about. Let's dive right in:

Watch the full episode here: https://www.youtube.com/watch?v=DsgYuOw3qGo

The Brand Mistake That Costs Your Brand — Chris Willow on Jolly's TLDR Podcast

1/ Wrong Category Is Worse Than No Category

Chris's old brand "Service Provider Pro" accidentally conjured pest control and home services in people's heads. A category, but the wrong one.

His take: having no category association at all is fine. Having the wrong one is fatal.

That landed hard for me, because we just renamed Jolly SEO to Jolly Search for the same reason. "SEO" was too narrow, and too easily dismissed as "the thing AI is killing."

If your brand name implies a category you don't actually serve, that's not neutral. That's a tax you pay every time someone hears your name.

2/ Brand Advertising Is Wildly Underlooked Right Now

Chris was blunt on this one:

Nobody buys on the first touch. They get in your funnel, research you a month later, come back a year after that. The "clean attribution funnel" is fiction.

This is the exact reason we lean into earned linkbuilding over paid placements. Brand mentions in front of the same audience for years compound. A one-off paid click does not.

He also called out the obvious one nobody admits. If your brand is three letters (SPP, ABC, XYZ), every dollar you spend on ads gets remembered as a string of letters, not a company. The brand never sticks.

3/ Until $1M, Do One Thing

Chris's mental model for agency growth:

Pick one service. Be loud about that one service. Become the go-to person for it. Your positioning, your homepage, your content, your hires, all sharpen around that one spear.

He says you can run an agency to seven figures on that alone, and only then start adding sibling services.

This is exactly what unlocked Jolly. We tried being a "content agency that also does PPC and a little linkbuilding" for a year. Went nowhere.

When we pivoted to "Done-for-You HARO", Jolly grew 5x in 2 years:

Jolly's monthly orders fulfilled, Sep 2019 to Jul 2021, growing 5x with the Done-for-You HARO pivot inflection in April 2020

If you're under $1M and feel scattered, that's your sign.

4/ You're Selling Taste, Not Hours

The reframe I keep thinking about:

Clients aren't paying you to do the work. They're paying for the seal of approval that you did the work. Your taste, your vetting, your reputation.

That changes how you think about delivery. AI helping in the middle? Fine. Another agency white-labeling underneath you? Also fine, as long as you stand behind the result.

I needed to swallow this one. For years I prided myself on "100% in-house at Jolly." Clients didn't actually care. They just wanted the outcome.

Side note from Chris: if you refer a client out to another agency and they screw up, it reflects on you.

Want to refer clients to an agency you can trust? Here is our partner program.

5/ Patience Is The Secret Ingredient

Chris closed with the line that's been rattling around my head all week:

"If you're in the game long enough, it works out. Not many people stick with it these days."

Every founder I know oscillates between "we're crushing it" and "are we even a real company." The DMs telling you you're killing it usually don't match how you actually feel.

But on a long enough timeline, the brand compounds. The reputation compounds. The relationships compound.

That's the whole game.

Until next week,
Greg

P.S. Curious what "earned linkbuilding" looks like in practice (the thing Chris and I were both nodding about under brand-building)? Hit reply and I'll send you live examples.

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