Skip to content

Many Hats: An Honor or Warning?

  • January 12, 2026

I was on a call the other day with a founder who told me, with a mix of pride and exhaustion, "I wear a lot of hats."

We’ve all heard it. In the startup and small business world, it’s treated like a badge of honor. It implies you’re scrappy, agile, and capable. But when I hear "I wear a lot of hats," I don't hear heroism. I hear a bottleneck.

I hear someone who is the CEO, the CFO, and the CMO all at once. And usually, that means they are doing three jobs poorly instead of one job well. Let's be real, no once can be everything all at once. 

Here is the unsexy truth about the "DIY" approach to marketing and growth.

 

The Horrible Catch-22

Most small businesses are stuck in a loop. I call it the "horrible catch-22".

You need more sales to fund a real marketing budget.

But you can't generate those sales without effective marketing.

So, you try to bridge the gap yourself. You write blog posts at midnight. You try to manage a CRM between sales calls. You "DIY it all" because you don't have the resources to hire a dedicated team.

The result? Inconsistent, sporadic marketing efforts. You post on LinkedIn for a week, get busy with delivery, and then go silent for a month. You build a landing page, but the "contact" form dumps leads into a spreadsheet that nobody checks.

You aren't building a funnel; you're building a leaky bucket.

 

The Skill Gap You Can’t Google Your Way Out Of

The other problem with the "Many Hats" theory is that digital marketing has become stupidly complex and channel-specific dependencies .

Ten years ago, maybe you could wing it. Today? Effective marketing requires navigating audience-building techniques, email privacy regulations, and complex content strategies.

Startups often face a significant skill gap here. You might be a visionary product founder, but that doesn't mean you know how to set up HubSpot workflows to automate lead nurturing. And you shouldn't have to.

From Data Silos to Revenue Operations

When business owners try to force it, they end up with "messy information" and data silos instead of insights. They spend hours on manual data entry that could have been automated. It’s a waste of the one resource you can't get back: your time.

You Don't Need a CMO. You Need a Roadmap.

 

Strategic Marketing Consulting vs. The Full-Time Hire

Here is the pitch (you knew it was coming, but let's be pragmatic about it).

Breaking this cycle doesn't require raising a Series A so you can hire a VP of Marketing. It requires a strategic partner who can embed with your team and build the roadmap for you.

That is what we do at Tough Terrain Media.

  • Marketing Consulting: We don't just "run ads." We fix the operational agility of your business.
  • Funnel Optimization: We look at your funnel to find exactly where people are getting lost and fix the user experience.
  • CRM Optimization: We turn your CRM from a digital graveyard into something that actually helps you close deals.

We provide the external expertise to break that "catch-22" so you can invest in growth without overstretching your internal capacity.


Partner with a Fractional Growth Strategist

If you are tired of the "hustle" and want to build something sustainable—where your marketing supports your sales rather than competing with it —let's talk.

You keep the CEO hat. We'll handle the growth strategy.

Related Posts

You may also like this

Lean Into CRM

September 3, 2025
Are you a business owner or part of a small team juggling multiple tasks to keep your company running? It's easy to get...

From Megaphone to Magnifying Glass: Why Smart Startups are Changing their Marketing Game

January 14, 2025
Remember the good old days when marketing was all about shouting from the rooftops? Blasting out emails, churning out...

Is "Industry Expertise" Sabotaging Your Business?

January 21, 2025
We've all been there. A meeting room filled with industry veterans, each armed with years of experience and a deep...
Free Guide

Beyond SEO: Conquering the AI Search Disruption with Generative Engine Optimization

A White Paper and Technical Guide to Generative Engine Optimization for Enterprise Success