Don't F**k It Up: How Founders and Their Successors Can Avoid the Clichés That Inhibit Growth

Don't F**k It Up: How Founders and Their Successors Can Avoid the Clichés That Inhibit Growth

by Les Trachtman


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Product Details

ISBN-13: 9781632991294
Publisher: Greenleaf Book Group, LLC
Publication date: 07/07/2017
Pages: 204
Sales rank: 860,205
Product dimensions: 6.00(w) x 1.25(h) x 9.00(d)

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"Don't f**k it up!"

It was the autumn of 2008 and the global economy had cratered.

At the time, I was several quarters into my tenure as the new COO of a company in the government-procurement industry, and my work there had just begun to bear fruit. We'd improved our gross margins and the bottom line was growing. But the credit crisis suddenly put us in a very precarious position, as it did with many other companies that fall. We urgently needed to make some bold moves to accelerate our pace of change. Our borrowing capacity was not sufficient to fund our sales growth. Even with increased sales volume our margins were not sufficient to generate ample enough profits. Our systems and our processes needed an overhaul to handle the larger order volume.

The company's founder was a larger-than-life charismatic leader. He was happy with the progress we'd been making, and although he understood the need for fast action in the face of crisis, he was also very nervous. Change meant we would be breaking from the script he'd created and followed since the company's beginning. One day when we were wrapping up a conversation about the changes, he ended with a few words of caution.

"OK," he said, "but don't f**k it up."

I didn't pay much heed to his words in that moment, but the strain in his voice — joking and at the same time deadly serious — remains a vivid memory. I had heard the founder utter the phrase casually to others in the company. It was his small way, I assumed, of dealing with his feelings of discomfort when giving up control. My guess is that if you've never said this in a joking way to one of your key employees, you've probably thought it.

Over time, however, I've come to realize that seemingly harmless little comments like "Don't f**k it up," "Get it right," or even "Be careful" are among the worst things you can say to an employee. That's because while you may say it as a joke, your employees will hear it very differently. They hear "Don't fail — or else."

They hear you warning them not to take risks, not to try new things, not to attempt anything that might not work.

Is that what you want your employees' marching orders to be? Not if you want to grow and scale your company. You want them to show initiative and take measured risks that yes, occasionally, might not work. There are always unforeseen challenges involved when you blaze new trails, and the people you've hired need to know in advance that it's OK while trailblazing to hit some dead ends and even fall off a few cliffs.


The irony is that every founder knows the need for innovation very well. You created new value in the market by doing things others couldn't or wouldn't do, and you suffered plenty of foul-ups and failures along the way. Growing your business requires your employees to advance with that same spirit of adventure and discovery. Teams innovate and grow their abilities when they are free to experiment and then collaborate on solving the new problems exposed by their setbacks and failures. You want to challenge your team to try things that might fail at first. You want them to become adept at recognizing failure quickly, regrouping, and then trying again. But then realize success.

Success is the brass ring for entrepreneurs. It's what you put in all those long hours for. It's how you keep score. It's how you build wealth and make your investors money. And if you are not careful, it can be what causes your demise.

Whenever you read about a company becoming "a victim of its own success," you'll find this kind of "Don't F**k It Up" culture. Companies squander their early competitive advantages and then disappear because great success in one narrowly defined area can squelch debate and foster a risk-averse mind-set among employees. The founder's comment, "Don't f**k it up," didn't really slow me down because I had known him for years and I was confident about our strategy. Most other people in the company, though, would likely take those same words to heart, as a warning from the big boss. And that can be a big problem, because employees who are taught to mistrust their own instincts are not very likely to trust their colleagues' instincts, either.

Fear of failure can easily poison a company culture. Team-building efforts are useless when everyone's first imperative is CYA — cover your ass.


Dominance in minicomputers made Digital Equipment Corp. (DEC) one of the most profitable companies in the world in the late 1980s. Led by Ken Olsen, its founder, DEC's minicomputers helped usher in a new era in computing, overtaking the once-dominant mainframe. In 1986 Olsen was named America's most successful entrepreneur. It wasn't long after that that Olsen forgot the lessons of his past and shielded himself from anything that might disrupt his own empire. Instead he believed that "the personal computer will fall flat on its face." Obviously, he was dead wrong. The PC flourished, with Digital Equipment missing that revolution. DEC was unceremoniously absorbed into Compaq Computer Corporation some six years later, a victim of its prior success.

Kodak was one of the world's most admired brands in 1996. Its market dominance in film enticed its out-of-touch management team to hang on to obsolete assumptions about the advantages of film-based photos over digital intruders. It might have considered letting the new generation of digital entrepreneurs within Kodak take the reins. But it never believed its empire was at risk or managed to wean itself off its revenue stream from photographic film. Kodak filed for bankruptcy liquidation in 2012, paralyzed by its past.

In 2000 Reed Hastings, the founder of what then was a fledgling company known as Netflix, had the gall to suggest a business partnership to John Antioco and his management team at Blockbuster Video. Antioco is no dummy. At the time, in fact, Antioco was viewed by many as a retail genius. But during Hastings's visit, Blockbuster was feeling pretty insular and didn't believe that this almost unknown company's innovative business model offered any value. In fact, it was reported that Hastings got laughed out of the room. Who is laughing now? Blockbuster went bankrupt in 2010, and Netflix is worth almost $70 billion.

We know there were many people inside each of these companies with bold ideas and the ability to make strategic pivots away from fading sources of revenue, but all of them were hamstrung by their leadership's choruses of "Don't f**k it up!"

"I know more about this company than anyone ever will."

The founder's attention to detail was legendary. From the time he founded his financial services software company, he was intimately involved in virtually every decision that needed to be made, and those decisions had set the stage for the company's success. He was one of those founders who could truly claim that no one knew his company as well as he did.

I came aboard to take over the role of CEO to help this founder, whom we'll call Elliot, take the company to the next level, as it was the kind of fast-growing company with strong fundamentals that could attract the interest of strategic buyers. Once I was there, though, it didn't take me long to recognize that we'd never reach our goal as long as Elliot remained the master of all detail.

One day I was talking with Elliot as we walked past the employee kitchen area when he interrupted me to point out something that had been bothering him. He'd seen tens of milk cartons of several different varieties in the refrigerator, and he wondered how we could possibly need all of this. He recalled the days when one container of regular milk would have sufficed.

I figured this was the perfect moment to set some new boundaries for Elliot's attention (even though I would have much preferred to finish our prior conversation). I told him that if he truly wanted us to succeed in the task I'd been hired for, we should never again discuss the employee kitchen. In fact, I suggested that from now on, he should try not to bother himself with any question that put less than $100,000 worth of company resources in play.

I can't ask you to stop worrying about little things. It's like telling someone not to think about pink elephants. Tiny details would always arise in your mind because your relationship to your business is so intimate. Elliot hadn't yet formulated a strategy for dealing with those thoughts. That's why the bright-line boundary of $100,000 turned out to be an excellent tool for maintaining his new focus: "Is that the exact PMS color of our logo?" Is that a $100,000 issue? No? Then forget it. Like most entrepreneurial minds, Elliot's was both voracious and decisive — as long as it had a target to hit. The $100,000 figure gave him that focus.

Drawing a bright line on such matters can be crucial to developing the mental discipline required for scaling your company. I've found that if you can develop a rule of thumb that truly resonates with you, like an arbitrary dollar figure or perhaps an organizational level ("Nothing done more than two levels below me is worth worrying about"), then you can cut way back on how much of your precious time and attention is wasted on trivia.

That day in the employee kitchen, Elliot had interrupted what could have been an important discussion with his new CEO to ponder the company's milk expenditure. He will never know what valuable thoughts he didn't think during the minutes when he weighed the relative merits of cutting back on the milk options.

It's not easy to step back from your natural habit of having a hand in everything. You built your organization by sweating every detail, and now it feels unnatural to start ignoring those details. Then, once you truly leave those details to other people, you face yet another challenge, because those people are guaranteed to make a lot of mistakes.


Elliot and I often discussed how, in order to meet his goals, people were going to do things in ways he'd never agree with, and some things were going to get f**ked up. But, at the risk of sounding paternalistic, the process of building a team is not that different from raising a healthy, self-sufficient child. It's not possible to be there with them constantly to ensure that they do the right thing all the time. You need to trust that with the right guidance they won't get themselves in too much trouble. And when they do get in trouble, when they fall and skin their knees, it's your role to help without being judgmental. You want them to learn from their mistakes and the resulting painful consequences.

The other important benefit of ignoring these low-level concerns is that it helps your team take over responsibility for them instead. That's how you slowly grow the decision-making muscles necessary to attain scale. The milk question was emblematic of a much larger problem at the company. Elliot's employees had helped feed his mania for details by going to him when they were making even the smallest decisions. The $100,000 mark was a helpful tool in that regard as well. He had to train himself to stop caring about countless small decisions he used to spend days obsessing over.

As a founder, it is completely natural to respond to a question posed to you by an employee or to quickly jump in to solve a tough problem. When you do, you fall into a trap. Making quick, decisive decisions is always faster, easier, and usually results in better decisions. But it encourages reliance on you rather than on an employee's own intellect and capabilities. Pausing to realize that not making a decision, though it may be painful, is the kind of tough love required to help employees build their own decision muscles will be an important ingredient of your organization's growth.

Mistakes can be uncomfortable to witness, and waste can feel even worse. Personally, it drives me crazy to see employees squandering company resources, whether it's the choice of an expensive hotel while traveling on business or leaving the office air-conditioning pumping all weekend. I remind them to be frugal with the accessories we purchase for our computers, subscriptions to unnecessary services, or overnight delivery when we can wait an extra day, but at the same time I try not to involve myself deeply enough in minutiae to know just how much they may or may not be wasting. If I did that, I'd be wasting two things that are much more valuable — my time and my attention.

So, instead of attempting to monitor wasteful behavior, I try my best to do what leaders are supposed to do, which is to set the tone for the entire company. The best way to promote respect for the value of company resources is to make sure you exhibit that respect yourself.

For instance, I make sure that my own expenses and reimbursements are more than reasonable. I don't stay at expensive hotels when traveling on business, and I often drive for six or seven hours to business destinations if flights are too expensive. And when my cell phone failed to survive a quick dip in the Severn River one day, I learned that I could save the company $600 if I waited 30 days to replace it, when my cell-phone account became upgrade-eligible.

The next morning, everyone in the office knew the reason why, for the next month, I would be using my iPad as a clumsy cellphone substitute.

"I could have told you that would happen."

Our management team toured the battlefield at Gettysburg for a leadership exercise about how the battle was fought. We climbedup the ridgeline known as Little Round Top and paused to hear a reading of the speech that Union Colonel Joshua Chamberlain gave to his 20th Maine Regiment before the first day of battle. The monument to that regiment is one of the most popular at Gettysburg because of the famous do-or-die spirit with which the 20th held its ground.

Little Round Top sat at the extreme left flank of the Union line, and a collapse of that flank would have been disastrous for the rest of the Union Army. General Strong Vincent gave Chamberlain explicit orders to "hold this ground at all costs."

This clear statement of intent led to one of the most famously valiant episodes in the three-day battle. On the afternoon of July 3, with Confederate forces making their way up Little Round Top, Chamberlain's men ran out of ammunition. The rebels were firing their guns just 30 yards away when Chamberlain and his fellow officers led a downhill bayonet charge. A Confederate officer aimed his pistol at Chamberlain's face from a distance of just a few feet, but the gun misfired. Sharpshooters from another Union unit arrived in the nick of time to scatter the remaining Confederates.

It was nearly a religious experience for me to walk in the footsteps of the brave soldiers who fought that battle and literally changed the course of American history. The sum effect of General Vincent's clear orders, "hold this ground at all costs," motivated Chamberlain to lead his men to make a bayonet charge with no ammunition. They were told they could not afford to fail, and so they summoned the courage to succeed. Little Round Top was held, and the next day the Confederate Army retreated from Pennsylvania, never to return.

This fundamental leadership imperative, of offering clear goals and clarity of intent, is the most important tool you have in resistingyour natural entrepreneurial urge to involve yourself in every little decision that affects your company. General Vincent knew he couldn't be at Little Round Top himself that day, and with no cellphone service, he entrusted Chamberlain to do his job. But he didn't leave it to Chamberlain to imagine what that job was, or what success looked like. He drew a vivid image of that day's objective — hold the hill at all costs.

On the opposite side of the battle, we learned that General Robert E. Lee was not nearly so clear in expressing his own Commander's Intent, and to this day some scholars believe the South could have won at Gettysburg and perhaps the entire war if Lee's communications to subordinates had been more explicit. The Northern defenses were centered on what was known as Cemetery Hill, and on the first day of battle Lee sent a courier to Colonel Richard Ewell with written orders to take the hill "if practicable, but to avoid a general engagement until the arrival of the other divisions of the army." Having been offered the option of waiting, Ewell decided to rest his tired troops. By the time Ewell finally attacked, on days two and three of the battle, the Northern troops were so well dug in on Cemetery Hill that the Confederate attacks were repulsed with heavy casualties.


Excerpted from "Don't F**k It Up"
by .
Copyright © 2017 Leslie S. Trachtman.
Excerpted by permission of River Grove Books.
All rights reserved. No part of this excerpt may be reproduced or reprinted without permission in writing from the publisher.
Excerpts are provided by Dial-A-Book Inc. solely for the personal use of visitors to this web site.

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