The Biggest Problem Startup Founders Don’t Know They Have

by | Sep 28, 2025

“Fix our positioning” doesn’t appear on many to-do lists or strategic annual priorities. But the symptoms of positioning problems create daily friction and reduce the impact of any business execution.

Positioning is the clarity you have around these important questions:

  • Who are we really for, specifically? Who do we not market and sell to?
  • How do we describe what we offer to the world?
  • What benefit do we actually deliver to our target customer?
  • How are we different from the competition and alternatives?

This clarity and focus make any execution work better.

Anthony Pierri and Robert Kaminski are the co-founders of FletchPMM, a positioning strategy firm for B2B SaaS companies.

They started Fletch after observing that most founders often confuse positioning with copywriting and marketing, and built their business by helping SaaS leaders make the tough, strategic choices about who they serve and how they win.

Over the last three years, Anthony and Rob have worked with more than 400 SaaS companies, from early-stage startups to scaling-up companies.

Fletch helps founders and B2B SaaS leaders clarify their positioning, sharpen their messaging, and translate strategy into effective homepage design.

In our practical discussion, they help founders see that positioning IS business strategy, not copywriting. It forces clarity and tradeoffs to improve execution.

Anthony and Rob are on LinkedIn every week, reminding us why founders must (eventually) choose one clear path to scale efficiently.

Rob describes how bootstrappers struggle less with positioning than VC-backed founders:

“There is a difference between bootstrappers and VC-funded startup founders in successfully positioning their startups. Bootstrappers are willing to see a narrow opportunity and tackle it with focus, because almost every market is big enough to sustain a $10 million company.

“I don’t care how narrow you get, the world’s a big place. So even with a hyper-focused, verticalized niche, or a use-case play, there’s plenty of money if you do it well, and that’s very appealing to bootstrappers.

“Most VC-funded founders don’t focus as well, which creates problems. However, founders who truly understand positioning and the idea that it can evolve, whether they’re venture-backed or not, start with a very narrow focus to succeed as a leader. “

If your team is struggling with execution in your product, in your GTM, or in your messaging, the likely culprit is vague strategic positioning that makes it all work better—or not.

Focus to Grow Faster. But only always.

Check out this useful interview with Anthony and Rob of Fletch on the Practical Founders Podcast.

Greg Head posted this on LinkedIn on September 28, 2025.

Check out the comments and join the discussion on LinkedIn.

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