Fail Faster, Succeed More!

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🇺🇸 Salute to Our Troops! Thank You for Your Service & Happy Veterans Day!

Hey, Coach Will Here…

This week hits close to home for me, and I am guilty of this more than once. I keep seeing it happen to some of the brightest people I know, over and over again.

“Entrepreneurs are convinced failure is the enemy.”

They dodge it like the plague.

They want perfect plans, perfect launches, perfect products, like waiting for the stars to align before pulling the trigger.

Here’s what happens next. They freeze. They keep spinning their wheels.

They pour time and money into "getting it right" and never actually doing anything risky, anything real.

Then, suddenly, the market moves, the window closes, and their perfect plan becomes yesterday’s news.

Failing faster is the only way to win sooner and zero in on your success!

But the reality is that most founders hear this and immediately aim to fail less. That’s the trap.

They think failure is something to avoid.

No. Failure is feedback. It’s the fastest way to learn what works—what the market actually wants and what’s just bulls***.

Skip the fancy presentations and test your ideas in the muck. Screw up fast. Learn more and faster.

Adapt or die. Simple as that!

💥 The “BIG” Mistake

Here’s where most screwed up: they treated failure like a bug to fix instead of a feature to embrace.

They build everything for “launch-perfect,” ignoring that real progress is iterating through mistakes.

This situation was a real setback, as it made decision-making sluggish, led to analysis paralysis, and used up resources on perfecting things no one was interested in.

Instead of learning quickly from experiences, they stuck to their assumptions and missed valuable opportunities.

If you don’t fail early, you’re just slow-dying in plain sight.

🎯 Playing Games….

This isn’t new. It’s the same damn story playing out every decade.

Remember ERP in the ’90s? Companies bet millions on systems nobody wanted or used. CRM in the early 2000s was the same thing?

Same crap, different day—massive rollouts that sputtered because nobody tested what the real user needs.

Big Data frenzy in 2010? The pattern repeats: hype, overspend, underdeliver.

Everyone chasing the next shiny “thing” without bothering to figure it out on whether it actually helped.

Look at Netflix versus Blockbuster. Netflix failed in technologies, models, and picks early—and fast.

Blockbuster, stuck with the “perfect” video rental store model, wondered why it was gasping for air.

Kodak clung to film, ignoring digital because it was too scary to fail forward and adapt.

The pattern is always the same: excitement, overspending, disappointment—because they ignored failure as a learning tool.

If you want to win fast, you have to fail more.

💡 The Fix…..

Here’s how you avoid the quicksand most founders swim in:

Question 1: Are you testing assumptions or just building hopes?

If you're not testing the riskiest assumptions—market fit, pricing, distribution—you’re just going through the motions. Identify your biggest leap of faith and challenge it with reality as soon as possible.

Example: Instead of building a full product, launch a simple MVP that proves people want this thing.

Question 2: Are you failing in a way that feeds learning?

Failing isn’t just crashing paths—it’s failing with purpose.

Did you capture what went wrong? Did you adjust? Did it sharpen your next move? Failure without learning is just pain. No gain.

Question 3: Are you balancing ‘Fix It’ vs ‘Figure It Out’?

Your Founder's Compass should help you stay adaptable.

Fixing things means quickly addressing current problems with familiar solutions—like minimizing losses and resolving quality concerns, so you can keep moving forward smoothly.

Figure It Out means exploring new territory with creativity and tests. You need both to keep momentum.

Put it all together and you get a feedback loop that’s brutal, fast, and keeps you ahead of the herd.

Fail more, learn faster, and change direction quickly. That’s how you win.

🚀 AltLevel™ AI Power Prompt

Copy this prompt and paste it into your favorite AI tool.

Use this to stop guessing and start failing with purpose.

➡️ Next Steps

Step 1: Identify your single riskiest assumption. Don’t guess—list ‘em all, then pick the one that could kill you.

Step 2: Design a minimum test (survey, landing page, prototype). It must cost near zero and launch this week.

Step 3: Set a strict deadline for feedback and learning. No dragging this out.

Step 4: Decide what ‘fail’ means before you start. Be ruthless about changing direction if the test bombs.

Do these four steps by Monday. Don’t wait for the perfect time. That time doesn’t exist.

Fail fast. Win faster.

📊 Quick Poll

🎬 THAT’S A WRAP

Why "playing it safe" actually keeps you stuck while your competitors move ahead (it's counterintuitive, but true), plus that same pattern that seems to catch entrepreneurs off guard every decade—and honestly, most of us fall for it at least once.

I shared my simple framework for testing ideas quickly and affordably so you can figure out what works without betting the farm, along with some practical steps you can take this week to start learning faster instead of just hoping things work out.

Here's the thing: The businesses thriving right now aren't the ones avoiding mistakes—they're the ones learning from mistakes faster than everyone else.

While others are still overthinking and planning, you could be three experiments ahead, already knowing what actually moves the needle.

It's not about taking crazy risks. It's about taking smart ones.

➡️ Remember, fail more to win faster. No shortcuts. No excuses.

Coach Will - The Strategist

P.S. Here’s the kicker: no one starts out loving to fail. But every founder who wins quickly gets addicted to it—because it’s the only way to keep winning.

You don’t need more tools. You need to get comfortable losing fast.

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