Why Founders Can't Commit to a Position (It's a Leadership Problem)

The hardest part of positioning isn’t figuring out the right answer. It’s living with the fact that every option is flawed and choosing one anyway. Most founders can do the analysis. What they can’t do is commit — and that, more than any framework gap, is why so many companies stay blurry for years.

Rob Kaminski, co-founder and managing partner of Fletch PMM — a bootstrapped consultancy that has run this exact exercise with more than 600 early-stage B2B startups — has seen the pattern enough to name it. When Angelina Yang asked him the one thing he keeps telling founders that they never seem to execute, he didn’t reach for a tactic. He went straight at the psychology of the decision. “There’s a difference between understanding good positioning and messaging and then actually having the leadership skills to execute,” he said. “That’s probably the biggest issue.”

Smart founders arrive, then freeze

The failure isn’t ignorance. In Rob’s experience the founders are sharp — “they actually kind of know their stuff.” Run them through a positioning exercise and “they’re oozing with insights, they help us shape and frame all these different strategies.” And then the exercise stalls at the only step that matters. “But then they don’t choose. And that’s just bad leadership.”

That’s a deliberately provocative framing, and Rob means it. He ties the whole job of a founder to this exact moment. “The reason why founders and executives get paid the big bucks isn’t necessarily for their in-the-weeds smarts. It’s because they have to make these tough choices that require trade-offs.” Positioning is where the trade-offs are unavoidable, so it’s where leadership either shows up or doesn’t.

Every option is supposed to feel bad

Part of why founders freeze is that they’re waiting for an option that doesn’t have downsides. It never comes. Rob recalls a founder who nailed it after being shown six or seven genuinely different strategies. “He said, ‘You know, Rob, all six of these suck. And it’s not your fault. They all just suck because they all have trade-offs.’”

That’s the real nature of the decision, and Rob has a phrase for it: choose your hard. “Go into a competitive space and see if you could battle it out. Go into a non-competitive space and hope that you could educate. And then the spectrum in between, they’re all really hard.” There is no version where you get certainty, which is exactly the wrong thing to want in this job. As Rob puts it, “If you wanted certainty, you should have been an accountant, not a founder.”

Refusing to choose has a name: too many ICPs

The most common way indecision disguises itself is a bloated list of ideal customers. Founders convince themselves that serving everyone is the safe, opportunity-maximizing move. Rob sees the opposite. “You’ll hear things like, ‘our ICP, we have six of them,’ and then they go and list them out.” His read is unsparing: a company with six ICPs “is either extremely successful and has the team and resources to go after different segments, or they’re kind of a delusional early-stage startup that doesn’t really know who they’re serving just yet.”

Because markets don’t reward breadth from unknown companies. “Markets are wildly fragmented,” Rob says — every buyer is in a unique situation with a unique toolset and its own baggage. Trying to speak to all of them at once makes you “harder to buy” and “your story will be less believable.” And the thing an early startup can least afford is confusion, “because the main issue you’re gonna have is no one knows who the heck you are at this point.”

The 10-day chicken-out

Even founders who do commit often un-commit before the strategy has a chance. This is the part Rob finds most frustrating. “The most frustrating thing for me is to see a really good strategy only being run for 10 days.” They love it, they launch it, and then “we check back with them and they’re back doing the old broad thing. They basically chickened out.”

The uncomfortable truth underneath all of it is that positioning doesn’t pay off on a startup timeline that satisfies impatience. “This stuff takes eighteen to thirty-six months to truly carve out a reputation,” Rob says, “and most founders don’t have the staying power for that.” The only exception is an unfair distribution advantage — real fame, a large network, or a product-led growth loop. Absent that, the work is repetition: “You just have to repeat yourself over and over for years until people suddenly are like, ‘Man, that’s the person that always talks about X.’”

Which reframes the whole problem. The founders who win at positioning aren’t the ones with the cleverest angle. They’re the ones with the nerve to pick a flawed option and the stamina to stand behind it long after it stops feeling exciting.

FAQ

Why do most founders fail at positioning?

Not from a lack of understanding — most founders grasp the strategy well. They fail at the commitment step: shown several viable positions, they refuse to pick one. Rob Kaminski calls this failure to choose “bad leadership,” since making trade-off decisions is precisely what founders are paid to do and where positioning succeeds or dies.

What does “choose your hard” mean in positioning?

It means every positioning option carries real downsides, so the choice isn’t between good and bad — it’s between different kinds of hard. A competitive category means fighting incumbents; a new one means expensive education; the middle is its own struggle. Founders wait for a painless option that doesn’t exist. Accepting the trade-offs and committing is the job.

Is having multiple ICPs a bad sign for a startup?

Usually yes. A company claiming six ideal customer profiles is either large enough to resource all of them or, more often, an early-stage startup that hasn’t decided who it serves. Because markets are highly fragmented, trying to address everyone makes you harder to buy and your story less believable when nobody knows you yet.

How long does it take for positioning to pay off?

Roughly 18 to 36 months of consistently repeating the same message before a market strongly associates it with you. Most founders quit before that. The only shortcut is an unfair distribution advantage — existing fame, a large network, or a product-led growth loop. Without one, reputation is earned slowly through repetition, not clever phrasing.

Why do founders abandon a positioning strategy too early?

Impatience. Rob describes founders who love a new strategy, run it for about 10 days, see no instant traction, and quietly revert to broad, generic messaging — they “chickened out.” Positioning compounds over months and years, so pulling the plug after days guarantees it never gets the runway it needs to work.

What makes positioning a leadership problem rather than a marketing problem?

Because the blocker isn’t analysis — founders can do that — it’s the willingness to make an irreversible-feeling trade-off and stand behind it. Leadership is defined by making hard choices under uncertainty. When a founder understands all the options but won’t commit to one, the failure is in leadership, not in the marketing craft.

Should a startup try to serve everyone to maximize its market?

No. Serving everyone makes you harder to buy and your narrative less credible, especially before you have brand recognition. Markets are fragmented into buyers with unique situations, tools, and constraints. A narrow, believable position aimed at one segment beats a broad one aimed at all of them, particularly when no one yet knows who you are.

What’s the risk of not committing to a position?

You stay invisible. Without a clear, repeated position, the market can’t file you anywhere or recommend you to anyone, and no amount of feature-listing fixes that. Indecision often hides behind long ICP lists and constant messaging changes, both of which reset any recognition you’d otherwise be building.

How do the best founders make positioning decisions?

They accept that all options have trade-offs, pick the one they can most defensibly execute, and hold it long enough to compound — even when it stops feeling exciting. They treat the choice as the leadership act it is, rather than waiting for certainty. As Rob says, certainty is for accountants, not founders.