They Didn’t Pivot and Paid the Price

What Companies Like Monster.com, Redbox, and Others Can Teach You About Marketing Smarter

Another one bites the dust.

As of this month, Monster.com—the once-dominant job site—was quietly shut down by its parent company. No big sendoff. No press tour. Just… done. A cautionary tale in real time. But if you think this only happens to bloated corporations, think again. Because the same thing that killed Monster, Redbox, Spirit Airlines, and a dozen others?

It’s probably lurking in your business right now.

And no, this isn’t fearmongering. It’s a mirror.

Let’s talk about why even once-iconic brands collapse… and how to make sure you’re not accidentally following in their footsteps.

The Classic Failures That Still Haunt Boardrooms

Let’s start with a few greatest hits—companies so notorious for refusing to evolve that their names are practically business school punchlines.

Blockbuster

had a chance to buy Netflix in 2000. They passed. Why? Because they couldn’t imagine people ditching Friday night VHS rentals for… streaming.
→ They bet on nostalgia instead of behavior.

Kodak 

actually invented the digital camera. Then buried it, scared it would kill their film sales.
→ They prioritized short-term revenue over long-term relevance.

BlackBerry 

insisted business users would never abandon their physical keyboards.
→ They confused features with emotional loyalty.

These stories are well-worn, yes. But they matter—because they’re still happening. Right now. To businesses with names you do recognize.

The Modern Pivot Fails You Might’ve Missed

Monster.com

At its peak, Monster was the job search. But while LinkedIn doubled down on networks and content, Monster froze in place. Same basic site. Same strategy. The result? Shuttered. Irrelevant. Gone in 2025.

Spirit Airlines

Known for cheap fares and “barebones everything,” Spirit built its brand on being the anti-airline. But when travelers demanded reliability over gimmicks, and their merger collapsed, they filed for bankruptcy. Brand promise? Useless if the product doesn’t evolve with the market. Spirit is still holding on after a failed merger, so perhaps their slow pivots will eventually work out.

Redbox

Those DVD kiosks outside Walgreens? They exploded in the 2000s. But while Netflix turned into a tech giant, Redbox stayed stuck in physical media. When they finally tried to pivot into streaming… it was too little, too late.

Parachute Home

A darling of the DTC bedding world, Parachute opened 26 stores—then abruptly closed 19 in 2025. Why? Because scaling retail only works if your brand can carry it. They skipped the groundwork and unfortunately learned that lesson the hard way.

Tally (Fintech)

Pivoted from DTC debt payoff to B2B SaaS. Lost their core users. Lost their mission. Then lost the business.

Damon Motorcycles

After years of hype and zero product delivery, they rebranded in 2025 as … an AI company? A pivot so detached from their original promise that it practically screamed “we’re out of ideas.”

Lesson across the board? You don’t get to skip evolution. Not as a brand. Not as a business. Not anymore.

The Real Reason These Stories Should Matter to You

Let me be blunt: Most businesses don’t realize they’re falling behind until it’s too late.

Why?

Because your business is still “doing okay.” Because the website still kinda works. Because leads still come in here and there. Because no one’s complaining—at least not loudly.

But meanwhile:

• You’re relying on tactics that peaked in 2018.
• Your brand voice hasn’t grown up with your audience.
• You’re still marketing like someone who’s trying to start a business… not scale one.

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And let’s be honest:

• You’ve been meaning to fix that funnel.
• You know your old SEO isn’t working so good any more.
• You cringe a little every time you send someone to your homepage.

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And you keep putting it off.

Because business is busy. Because you’re tired. Because you “just need to get through this quarter.”

That’s what all these brands said too.

How to Know When It’s Time to Evolve

Here’s the thing: Not every pivot is a panic move. The smart ones? They’re preemptive. Strategic. And grounded in data—not desperation.

If your gut’s already telling you something’s off, consider this your sign.

Here’s what evolving the right way looks like:

• You evaluate what’s working—and what’s just legacy noise.
• You audit your brand, offers, messaging, and digital presence holistically. (Pssst … we have a live workshop that will help you do that!)
• You design strategy for where you’re going—not where you were three years ago.
• You ask someone who’s not emotionally attached to tell you the truth.

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It’s not flashy. It’s not always sexy. But it’s what actually keeps your business in the game.

The Questions You Don’t Want to Ask (But Must)

This is the part where most people click away. Ugh I don’t want to face it.

Don’t! Because these are the questions that might save your business:

Ask yourself:

• Am I coasting on what used to work?
• Is our growth real—or just momentum from old wins?
• When’s the last time we got uncomfortable on purpose?
• Do I even know what part of my marketing is working?
• If my top three lead sources vanished tomorrow, would we survive?

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Ask people you trust:

• What’s confusing about how we show up online?
• What feels outdated in our branding or message?
• What’s missing that would make us feel next-level legit?

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If your stomach clenched reading any of those, you just found your starting point.