Author’s Note
Welcome to another exciting week of marketing! Remember: If you have questions, just hit ‘Reply’. I read every email. Have a great week!

Ask Matchbook

This week's questions from readers:

Q: My agency wants a 6-month contract. Is that normal?

A: Yes, 3-6 months is standard. Agencies need time to test, optimize, and prove results. But make sure the contract has clear performance milestones and an out-clause if things aren't working by month 3. If they're pushing for 12 months upfront with no flexibility, that's a red flag.

Q: Is it normal for my agency to ask me to write the ad copy?

A: No. Writing ad copy is the agency's job. If they're asking you to do it, they're either (a) understaffed, (b) lazy, or (c) not actually good at what they do. You should provide input (offers, messaging, brand voice), but they should be creating the copy. Use the Vendor Scorecard to clarify responsibilities before you sign.

Today you’ll read about:

  • Marketing feels risky because you lack a buying framework

  • Agencies sell expertise you can’t easily evaluate

  • Trust erodes faster than money is lost

  • Structure removes fear and improves decisions

One thing I didn’t appreciate until I spent time around a lot of small business owners is how emotionally loaded marketing decisions are.

From the outside, marketing decisions tend to look like straightforward business choices, but it’s rarely that clean. There’s usually hesitation baked into the process.

I’m guessing you’ve felt that too, to some extent.

You want to grow and you know marketing is part of that, but right before you commit, there’s this quiet tension. It doesn’t feel like the decisions you’re used to making in your business. It actually feels closer to gambling.

There are real reasons it feels this risky.

You’re buying something you can’t inspect

Most business purchases are tangible.

You can see inventory. You can test equipment. You can watch work being done. Which means that even if it goes wrong, you understand why.

Marketing isn’t like that.

You’re paying for a process you can’t fully observe (not to mention you don’t perfectly understand), with results that are promised but not guaranteed.

That alone creates friction, and not because you don’t trust people, but because you don’t have a clean way of evaluating what you’re buying.

Which is where the anxiety and nervousness around marketing show up.

Every option sounds confident

If you talk to three agencies, you’re going to get three explanations for why their approach is the best.

None of them are necessarily wrong. They’re just describing what they know how to do.

But you’re the one trying to decide between competing expertise while also running payroll, dealing with customers, and keeping the rest of the business moving.

And since there’s NO way for you to magically become a marketing expert overnight, you HAVE to rely on third party expertise. Agencies know that, which is why they all make sure to sound so confident on sales calls, because confidence sells.

The pressure isn’t just financial

When owners talk about bad marketing decisions, they rarely focus only on the money. They’re also usually (a) frustrated over trying something that didn’t work and (b) afraid of falling behind competitors.

Those feelings alone aren’t the problem, the problem lies in feeling those things while at the same time losing complete trust in the way out: Marketing.

I’ve heard variations of the same sentence more times than I can count:

“I don’t know who I can trust.”

Once that trust erodes, owners either churn through vendors trying to fix it, or they pull back entirely and decide marketing just doesn’t work for businesses like theirs.

Both paths are expensive and neither solves the problem.

This gap didn’t appear because everyone’s evil

It’s easy to jump from a bad experience straight to “agencies are bad.”

Some are bad, yes. But most people selling marketing services genuinely believe in and are experienced in what they’re offering. They’re not going around trying to scam you.

The problem is actually structural.

Marketing expanded faster than the average business owner could reasonably keep up with. Channels multiplied. Tools multiplied. Specialization exploded. Agencies adapted to sell expertise inside slices of that world.

What never developed alongside it was a neutral buyer framework.

Owners are expected to become informed purchasers in a landscape that is ever-evolving and without anyone in their corner.

The hidden cost isn’t just the first mistake

Losing money hurts when a hire goes wrong, but what sticks longer is what happens after.

  • Abandoning channels that would have worked if you’d given them more time or worked with a better agency.

  • Staying too long with vendors you don’t believe in because you’re afraid to start over.

  • Investing heavily in lead generation before you have systems in place to handle the leads.

Each of those experiences chips away at trust. Trust in agencies, but also trust in your own decision-making.

Reframing the solution

To fix this, most owners either (a) throw in the towel on marketing or (b) assume they need to buckle down and learn marketing techniques themselves

Both are gonna end up hurting more than helping.

Yes, it would be amazing if you as the business owner knew everything there is to know about ads, SEO, and email marketing, but you don’t have to.

What you need right now is to learn how to ask the right questions.

That’s a buying skill, not a technical skill.

And buying skills are more easily learnable. They’re also the primary skills I talk about in weekly newsletter issues (I’m biased, but I recommend reading them).

Need more help?

Not sure which channel makes sense for your business? Get a Channel + Readiness Review.

Tried marketing before and it didn't work? Book a Marketing Reset.

Ready to find an agency but don't want to vet them alone? Matchmaking is for you.

Already working with an agency but something feels off? Get an Agency Reality Check.

Bottom line: You’re not bad at marketing just because you think it sounds risky.

The owners who eventually get comfortable with marketing aren’t the ones who magically become experts. They’re the ones who build a way to think about decisions before they sign anything.

My goal is to get you there.

Till next time,

-Jason

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