The $30 Million Mistake Even Elite Players Make

Coaches universally praised Shedeur Sanders' elite athleticism. Projected third overall, he fell dramatically to 144th.

Why did an undeniable talent lose millions? He didn't check his playbook, literally or figuratively.

The Two Failures

First, literal. During a pre-draft meeting, the Giants handed Sanders instructions deliberately filled with errors. He missed every flaw, then was defensive about it.

Second, inherited. Sanders adopted his father’s bold approach without Deion’s Hall of Fame credibility, even skipping the "Draft Combine." Deion earned confidence through a legendary career. Including the Combine. Shedeur hadn't.

Same approach, wrong context. That assumption, and the slide to the fifth round, cost him $30 million in guaranteed contract value.

The Business Parallel

What happens when elite teams scale successful go-to-market (GTM) strategies without confirming that credibility transfers?

Markets shift quietly, then quickly. Deals once done in a single call now require consensus. Top reps improvise pitches mid-call to save meetings. Sometimes great execution and impeccable GTM Strategy fails because the Market has changed. And we often don't see this mismatch until we're asked why the quarter was missed.

Run a Red Team

Before adding headcount or launching another campaign, pause.

Run quarterly Red Team reviews. The simplest approach is to engage three sharp, internal operators who didn't make the plan, to break the go-to-market plan. Give them your strategy, buyer profiles, assumptions, and results. Their job: expose outdated assumptions, find weak spots, and show where reps are improvising to compensate. No fancy slides, just a lively, one-hour pressure-testing conversation.

Without regular Red Teams, here's what can quietly happen:

• Event sign-ups flatten, despite proven messaging.
• Top reps rewrite pitches mid-call.
• Deals once quick to close now require multiple revisions, longer cycles.

By the time you see it clearly, catching up becomes your only move. And catching up is so much more complicated than staying ahead.

A Common Strategic Error: Scaling Before Fit Is Proven

Don't believe the ground shifts underneath smart teams? Here's how it caught some of the best companies off-guard.

Slack scaled viral adoption then tried to layer on a sales-driven motion after the fact.

The shift was real: Salesforce acquired Slack for $27.7B. Salesforce sold through enterprise push, but Slack had grown through buyer-led pull. The new Enterprise Sales strategy was forced, not tested.

Chuck Ganapathi ( Gainsight COO, ex- Salesforce ) stated bluntly: " Slack is experiencing only modest growth, despite the current boom time for collaboration and remote work... if Slack couldn't gain ground in the midst of this monumental shift, when would it?"

They didn't run the wrong playbook. They ran an unvalidated one at scale, with real users, under real pressure. It cost time, retraining, and internal trust.

HubSpot crushed SMB markets with inbound strategies. When they pushed into enterprise, those tactics stalled.

Enterprise buyers weren’t clicking quick CTAs or bingeing blogs; they wanted governance, integration, and control. Deals slowed. Sales cycles stretched, acquisition costs spiked, and teams scrambled, burning months fixing a strategy built for the wrong audience.

HubSpot eventually adapted, but they paid with lost quarters, higher costs, and missed revenue opportunities.

Scaling assumptions without validation doesn’t just risk revenue. It costs irreplaceable time, internal credibility, and market leadership.

Dropbox's earliest growth came from users doing the selling for them.

Dropbox ’s early success was user-led growth: refer a friend, gain more storage. Users became their salesforce, fueling explosive adoption.

But this tactic became Dropbox’s biggest obstacle in enterprise markets. IT departments flagged it as shadow IT with no control, no visibility. The viral growth engine, perfect for consumers, stalled badly in enterprise. Dropbox was forced to overhaul its product, build admin controls, and reposition itself entirely.

The cost to Dropbox wasn’t just investment dollars; it was critical months lost trying to regain trust and traction in a suspicious enterprise market.

Figma watched all of this and did the opposite.

Figma appears to have watched these missteps carefully. They refused to scale prematurely. Instead, they waited until users naturally adopted the product across teams. Only after their strategy was proven by market pull did Figma layer in sales and marketing to scale further.

Figma didn’t scale, hoping for a fit. They scaled only after the market demanded it.

Personal Miss: When Fit Didn't Transfer

I learned this lesson the expensive way.

At Apex Fintech Solutions Solutions, we launched Fractional Fixed Income APIs to fintech platforms already in our orbit. Nick Franzese ran a phenomenal launch — a true master class in Partner and Product Marketing from beginning to end. The results were fast. The buyers knew us and the messaging landed, making the need clear and obvious.

Nick's team generated early wins in a new segment as well — treasury platforms. Same product. Similar product message. I modified Nick's ready-made playbook, targeting that new segment. But the response was silence. It turned out, they didn't know us. They didn't know why it mattered.

It wasn't a product-market fit issue. It was a go-to-market fit miss. Our strategy assumed brand awareness that didn't exist. That assumption turned into lost time.

The lesson was simple: brand awareness doesn't transfer across segments, and a strategy that works with one buyer might be invisible to the next.

The Boardroom Test

The pattern is clear across companies of all sizes. Which brings us to the topic every board should be covering.

Make GTM fit a standing board agenda item. Not just metrics and execution, but also strategic fit. Every CEO, CMO, and CRO should be ready to answer three questions:

1. What GTM assumptions are we operating on?
2. When were they last tested?
3. Where are we seeing early signs of market changes?

If you don't ask, your board will. With less time, and fewer options.

What assumptions are you running on that haven't been tested? Your results next quarter might depend on asking that question now.

The Red Team review takes an hour. The cost of not doing it? Quarters you can't get back. Or $30 million.