When Failing Fast Fails Executives

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“You dare to fail fast.” read the job description for a leadership role at a burgeoning startup. Pretty stark, isn’t it? “You dare to fail fast.” What exactly does that mean?

Be innovative, screw up, learn from it, grow.

Somewhere along all this failure, you’re also supposed to keep your job—or keep your business afloat—while celebrating all the mistakes you made and how you’ve learned from them.

In spite of the contrarian argument I present, I do get it. The problem is failure doesn’t pay the bills. Success does.

And for millions of leaders and entrepreneurs, failing fast doesn’t provide a game plan for success. It’s a tired eschewal—an avoidance to sharing real solutions to hard business problems.

Is failing quickly a healthy cliche to repeat over and over? Or does this mantra only hold merit with companies that are force-fed millions of dollars in VC capital—and therefore have plenty of cash to smooth over their financial mistakes and repeated failures?

Those that tout the fail-fast ethos often have enough money in the bank to buy time until they know what they’re talking about (and develop a real solution). Or they don’t—and we never hear about them or their ideas again.

Most do not have the luxury to fail.

Can you afford to take 20:1 VC odds on a unicorn or disappearing act with your livelihood? When does failure become reckless?

Famous Quotes Are Meaningless

There is a quote from WWII legend Gen. George S. Patton that drives me up the wall: “A good plan violently executed right now is far better than a perfect plan executed next week.”

Okay Patton—So I’m sending one hundred thousand troops into “violent execution” because it’s “far better” than next week’s perfect plan? Seems reckless, mate.

When is a moment of pause for strategic clarity warranted? Or is violent execution a reminder that indecision is a decision—and analysis paralysis may be your demise, anyway?  

This gets twisted further when you read about CEOs – or maybe you even worked for one – who love to talk about jumping off a cliff and building an airplane on the way down. (They stole that line from Reid Hoffman, one of LinkedIn’s co-founders who popularized it a few years ago, by the way).

And, I get it. Failures are inevitable as you take risks in business, and they should be embraced. But when you experience a big failure—famous quotes don’t provide solutions or offer a sound rallying cry for your team feeling the pain.

The Inside Story Of Failing Fast

As the CEO of a startup that has since closed, I’ve walked these shoes.

At Discover Podium, we pioneered personal career agents for busy tech executives. We started with no capital and bootstrapped over $1M in revenues the first year. We grew to over 20 employees. The growth we experienced was exciting and motivational.

We developed a software patent and earned the interest of millions of dollars in angel and venture capitalist investment. It seemed that nothing could slow us down.

Enter 2020.

We met the pandemic at our highest profit peak, and our revenue shrank to zero overnight as lockdowns were announced. Anyone that was fortunate enough to have a job was afraid to leave. Meaning, our clients were more difficult to come by.

How do you look 22 employees right in the Zoom and share that your violent execution was likely a flash in the pan? (Spoiler: you don’t. Call everyone directly)

After a few hundred personal phone calls to customers, we managed to avoid layoffs. While we squelched the hemorrhage, the future couldn’t be more uncertain. Afterall, we only needed 15 days to slow the spread…

Rather than cut deep and run—I took time to perfect a plan. I didn’t want our staff and their families to feel the full brunt of whether or not they would have a job. Sorry Patton, casualties can be avoided.

Everyone onboard knew that startups were risky places to work; however, I chose to give our staff the option to find less-risky work over time. Our remaining staff would help each other find that work, while everyone kept their salaries.

I knew this would be the death of Discover Podium. But it was a plan far better than violently asking the team to work double time to save the business—then discarding them like garbage if it didn’t work out.

An orchestrated surrender. The death of a dream. A strategy of compassion.

8 arduous months later, the entire team transitioned. Many into higher paying roles, which still brings me a smile.

The fail fast ethos would have everyone fired early to protect the profit lines. A slower more strategic approach meant bringing humanity back into business. A hill we should all be so lucky to die on.


What To Remember For Next Time

Here’s what I took away from an epic failure—these require more than a quote about failing fast and dusting yourself off.

Be calm: Communicate the failing situation with a calm demeanor. I didn’t want to create panic by not saying what was happening, or by saying too much. Be authentic and rise to the responsibility.

Don’t experiment so aggressively: I overdid violent execution, recklessly. I’d change the price of our services. I’d work on different packages until they got confusing to sell. I was too fast to hire and too slow to fire. Which gave me a new saying: “Disaster accelerates trends that are already in motion.” We were already likely to fail, COVID made sure it happened faster.

Listen to your gut: I often ignored my gut to appease advisors or to collect damning evidence to make a more perfect decision. Yes, Patton warned me about this! However, acting impulsively—and yes violently—can be equally damaging. Balance is key. You must put in the time to consider the data and your intuition to foster your decisions—but also make sure you make the decision and execute. You need both.

Make calculated bets: It’s smart to take risks and approach your business with experiments. Just don’t forget the “why” and overcorrect things. Taking risks in a measured, thoughtful way works well. The alternative is flailing. Making reckless bets for the sake of failing quickly can only be afforded (often) by those flush with cash—and repeated failure will demoralize your culture. VC fed startups beware.

Was It Worth It?


I wouldn’t take back the 100-hour weeks. I wouldn’t cut-and-run sooner so my bank account would have an extra zero. I wouldn’t change the way I handled our finances.

I may not have a multi-million dollar business anymore, but failing with Discover Podium was still the most fulfilling work I’ve done. Plus, I learned about what to avoid with my current company, ThinkWarwick.

I’ve never been more engaged as I was when I led our team through a crisis. I learned what was truly important: how to take care of people instead of working for my own financial success—even though “business is business” and other shallow quotes gave me an excuse to be an asshole.

Fail quickly? Not so fast.

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