How to Sabotage your Own Startup

How to Sabotage your Own Startup

by Random Entrepreneur

A true story is based on this book.Available on

# 0

Most startups do not succeed and most of them never deliver a positive return to investors. The reasons for failure can take many shapes: no product-market fit, running out of money, not the right team, poor product, you name it. Many of these reasons, however, have a common source: Founders (unconscious) self-sabotaging behavior.

The advice from startup accelerators is largely prescriptive. In contrast, this book seeks to induce an epiphany to help founders act using a via negativa approach, that is, identifying elements on their actions that are very close to spy-grade tactics for sabotage.

The notes and tips included in this book come from the Simple Sabotage Field Manual, published by the Office of Strategic Services (OSS) of the United States in 1944, which was also used later on by the CIA. The techniques outlined in the manual describe how to sabotage (enemy) organizations from the inside.

The idea is that once you are aware of how your own behavior, and of others in your startup, aligns with professional spy tactics for sabotage, then you can act upon it and remove those practices (i.e., via negativa) to give a better chance of success to your company and, perhaps, also to your life.

Random Entrepreneur

Via negativa: "the principle that we know what is wrong with more clarity than what is right, and that knowledge grows by subtraction. Also, it is easier to know that something is wrong than to find the fix. Actions that remove are more robust than those that add because addition may have unseen, complicated feedback loops."– Nassim Nicholas Taleb.

# 1

Talk as frequently as possible and at great length

Illustrate your points by long anecdotes and accounts of personal experiences, specially when talking to customers.

"The Mom Test" is overrated.


# 2

Delay the product launch until it is 100% completed


# 3

Never permit shortcuts to be taken in order to expedite decisions


# 4

Bring up irrelevant issues as frequently as possible


# 5

Haggle over precise wordings of communications, minutes resolutions


# 6

Refer back to matters decided upon at the last meeting and attempt to re-open the question of the advisability of that decision


# 7

Advocate caution and be reasonable

Urge your team to be reasonable and avoid haste which might result in embarrassments or difficulties later on.


# 8

Be worried about taken responsibility of any task or action

Raise the question of whether such decision lies within the scope of the team or whether it might conflict with investors or the board.


# 9

Demand written orders


# 10

Misunderstand instructions

Ask endless questions or engage in long discussions about trivial matters.

Quibble over them when you can.


# 11

Do everything possible to delay the release of new versions or your product

Even though features are ready to ship, don't deliver them until the version is completely ready.


# 12

Don't provision additional computational resources for your online services or app

... until the current ones have been virtually exhausted, so that the slightest increase on demand will mean a shutdown.


# 13

Order high-quality hardware, over-specialized services, and tools which are hard to get.

If you don't get them argue about it.

Warn that any viable alternative, e.g., open source, will mean inferior work.


# 14

In making workload assignments, always prioritize unimportant tasks

See that the important tasks are assigned to individuals with mismatching skills.


# 15

Insist on perfect work in relatively unimportant product features

Send back for refinishing those which have the least flaw.

Approve other defective features whose flaws are not visible to the naked eye.


# 16

Make mistakes in communication so that tasks will be assigned to the wrong team in the company


# 17

When training new employees, give incomplete or misleading instructions


# 18

To lower morale and with it, production, be pleasant to inefficient employees

... give them undeserved promotions and discriminate against efficient employees; complain unjustly about their work.


# 19

Hold conferences and networking events when there is more critical work to be done


# 20

Multiply paperwork in plausible ways

Start duplicate efforts.


# 21

Multiply the procedures and clearances involved in issuing instructions, tasks, payments, and so on

See that three people have to approve everything where one would do.


# 22

Apply all regulations to the last letter


# 23

Make mistakes in quantities. Confuse similar names.Use wrong addresses


# 24

Prolong communication with customers, providers, investors, regulators, ...


# 25

Misfile essential documents


# 26

In making copies, make one too few, so that an extra copying job will have to be done


# 27

Delay communication


# 28

When possible, refer all matters to committees, for further study and consideration

Attempt to schedule their meetings as large as possible – never with less than five people.


# 29

Spread disturbing rumors that sound like inside information


# 30

Work slowly, underperform, and procrastinate

Think out ways to increase the number of steps necessary to do your job.

Use a small and fancy laptop instead of a powerful server to complete computational intensive tasks.


# 31

Contrive as many interruptions to your work as you can

When working on a task, take needless time to do it. Check and test everything twice as often as you need to.

When taking breaks, spend a longer time than is necessary.


# 32

Even if you understand the language, pretend not to understand instructions in a foreign tongue


# 33

Pretend that instructions are hard to understand, and ask to have them repeated more than once

Or pretend that you are particularly anxious to do your work, and pester your team with unnecessary questions.


# 34

Do your work poorly and blame it on bad tools: software or hardware

Complain that these things are preventing you from doing your job right.


# 35

Never pass on your skill and experience to a new or less skillful employee


# 36

Snarl up administration in every possible way

Make mistakes or omit requested information.

Produce incoherent documentation and instructions so that they will have to be done over.


# 37

If possible, join or help organize a group for presenting employee problems to the management

... involving the presence of a large number of employees at each presentation.

See that the procedures adopted are as inconvenient as possible for the management.

Organize more than one meeting for each grievance, bringing up problems which are largely imaginary, and so on.


# 38

Make it hard to find how your product works


# 39

Mix good and useful features with superfluous and redundant ones


# 40

Give lengthy and incomprehensible explanations when questioned


# 41

Report imaginary spies or danger to the authorities


# 42

Act stupid


# 43

Be as irritable and quarrelsome as possible, without getting yourself into trouble


# 44

Misunderstand all sorts of regulations


# 45

Build something people do not want



The artwork, illustrations, and images of this book are openly licensed under a Creative Commons CC BY-SA 4.0 license.

The text of this book is based on notes from the "Simple Sabotage Field Manual". Office of Strategic Services (OSS) / CIA, United States, 1944, which is in the Public Domain.