Secret to Startup Failure Read online

  “I came, I saw, I failed.”

  “Success is one-percent inspiration, ninety-nine percent failure.”

  “If you haven’t succeeded yet, keep failing.”

  “The unfailed life is not worth living.”

  “When in the wrong, fail as the wrong men do.”

  “Be the failure you want to see in the world.”

  “To every success there is always opposed an equal failure.”

  “Call no man happy until he fails.”

  “A success is worth a thousand failures.”

  “You can fail all the things some of the time, and some of the things all the time, but you cannot fail all the things all the time.”

  Fail Fast. Fail Cheap. Fail Happy.

  SONIA LIN

  Secret to Startup Failure: Fail Fast. Fail Cheap. Fail Happy. by Sonia Lin

  © 2014 by Sonia Lin. All rights reserved.

  Cover design by n23art

  Edited by Marta Tanrikulu

  Illustrated by Sonia Lin

  All rights reserved. No part of this publication may be reproduced, distributed, or transmitted in any form or by any means, including photocopying, recording, or other electronic or mechanical methods, without the prior written permission of the author or publisher, except in the case of brief quotations embodied in critical reviews and certain other noncommercial uses permitted by copyright law.

  Although every precaution has been taken to verify the accuracy of the information contained herein, the author and publisher assume no responsibility for any errors or omissions. No liability is assumed for damages that may result from the use of information contained within.

  http://EntrepreNos.com

  eISBN: 978-0-9914265-0-8

  To all entrepreneurs

  who are crazy enough to keep failing.

  CONTENTS

  PREFACE

  WHO THIS BOOK IS FOR

  HOW TO USE THIS BOOK

  HOW THIS BOOK IS DIFFERENT FROM ENTREPRENO’S, THE WEBCOMICS

  CHAPTER 1 GETTING READY

  KNOW THYSELF

  CHAPTER 2 IMPRESSIONS VS. REALITY

  THE END OF THE TUNNEL

  FRIENDSHIP

  NETWORKING

  THE PERFECT LAUNCH

  NO MATTER WHAT, YOU’VE STILL GOT PIZZA

  CHAPTER 3 CO-FOUNDERSHIP

  DO YOU NEED A CO-FOUNDER?

  CO-FOUNDER’S DILEMMA

  MATCH MADE IN HEAVEN

  GOOD COP, BAD COP

  ALL IS FAIR IN LOVE AND … STARTUP

  DISTANCE

  TRUST

  COMMUNICATION

  CHAPTER 4 DEMANDS OF STARTUP CULTURE

  RAPID DEVELOPMENT

  LOGO MATTERS

  HOLIDAY CONFERENCE CALL

  THE BURNING ENTREPRENEUR

  LEAN STARTUP

  THE FIRST 100 LIKES

  THE ROLLERCOASTER RIDE

  CHAPTER 5 PRODUCTIVITY ISSUES

  PRODUCTIVITY DEBATED

  EVERYONE WORKS DIFFERENTLY

  BRAINSTORMING

  COLLABORATION

  THE OMNI OUTLOOK

  CHAPTER 6 IMBALANCE

  STAYING ABOVE WATER

  GET SET, GO!

  CONNECTIVITY

  BOTTOM LINE

  ALWAYS OPEN

  CHAPTER 7 PUBLIC RELATIONS PROBLEMS

  WINNING SOCIAL MEDIA STRATEGY

  TO PITCH OR NOT TO PITCH

  STEALTH MODE

  DIRTY LAUNDRY

  CHAPTER 8 WORKING ENVIRONMENTS

  HOME

  COFFEE SHOP AND LIBRARY

  CO-WORKING SPACE

  OFFICE

  EVERYWHERE ELSE

  CHAPTER 9 SUSTAINABILITY

  YOU ARE HUMAN

  THE TEAM

  BEYOND THE TEAM

  PLANNING

  PRODUCT DEVELOPMENT

  INFRASTRUCTURE

  CHAPTER 10 WRAPPING UP

  RETHINKING

  ACKNOWLEDGEMENTS

  ABOUT THE AUTHOR

  PREFACE

  This book germinated from the webcomic series EntrepreNo’s: Secret to Startup Failure that I have been maintaining to illustrate and ridicule the lack of work-life balance in a startup. While my own startup experience serves as the major inspiration of these comics, the readers of the series — who are mostly entrepreneurs, developers, and people with other roles who are influencers and enthusiasts in the startup scene — have been expressing how accurately these comics reflect the ups and downs of their startup life, in a subtle and funny way that only startup people understand well.

  This book is meant to take the comics further into advice on different aspects of a startup life while serving as a light, enjoyable read. It doesn’t teach success. It doesn’t teach how to code or run a business. It’s about sustainability at all levels that serves as the foundation for long-term success in an entrepreneurial career. While the title “Secret to Startup Failure” is meant to be tongue-in-cheek, as so many startup resources and experts are trying to give advice on success rather than failure, there’s a dose of secrecy implied, as the startup world for many people is still a black box despite what a thriving community it is today. This book is going to help people who are in the dark.

  It couldn’t have been more mysterious to me when I first treaded into the startup scene as someone who had never devoted my studies to business or computer science, in a city where I had barely lived for a little more than one year after finishing my Master’s degree. It was Chicago, where Groupon had just become a household name, where business schools were starting to breed entrepreneurs — including Northwestern, where I had just graduated from — where startup events were starting to burst the calendar and be hard to choose among. Life was filled with possibilities, and we — my co-founder and I — took nearly every single one of them. We had immense passion and energy, and we did everything deeming a startup successful and never slacked on the hours. We achieved some milestones that looked like a sure ticket to success — top prize of a business competition, national media coverage, endorsements from numerous organizations, and on and on. This early prodigy also enabled us to attract talent that injected new energy to the startup on a continuous basis.

  After all these endeavors and achievements, the startup still failed to grow into a sustainable business. It seems like we tried too hard, but we got it all wrong. None of us had worked in a startup and we had no idea what productivity and growth look like. We mistook red tape for growth. We mistook politics for discussions. We mistook fame for validation. So many years of experience, coming from so many talented individuals we were able to recruit, rendered a startup that looked nice and professional instead of producing something real. We were already operating like a corporation, but without a steady revenue stream yet, and the attention needed for the product was constantly diverted to trivial discussions that continuously drained our resources.

  And above all, we were not happy, and our lives were completely out of balance. We wanted everything done right and well, yet we never got to that point because we already had taken too many matters into our own hands. The company wasn’t driven by passion to create a change anymore. It drowned in its self-defined infinite loop in which the condition could never be met, and one simply had to try to escape before being further stuck. It’s not a lifestyle worth living again, not because it was crazy, but because it was crazy AND it didn’t get us a successful, sustainable startup.

  What I believe was missing from it was balance — what distinguishes work from life, day from night, different times of the day from each other, what regulates our rhythm and sets a limit on our indulgence when technology and connectivity trick us into thinking we’re invincible. We needed bala
nce to give perspective, to separate the important from the trivial, to contrast good and bad, to give the peace of mind to set priorities when overwhelmed by possibilities. We needed balance to give distance for mutual respect and appreciation, freedom for ownership and creativity, room for trial-and-error, as those are what separate startups from all corporations, that leverage individual power to defy the masses and create unique value.

  While there is much literature out there about startups, it won't make you laugh, but this one will. While there are enough experts telling the secret to startup success, this book tells you how to fail safely in preparation for the next big success. While everyone is saying you are not doing enough, this book says to make smart decisions on how to spend limited time and energy for sustainability — and nobody should care about that more than you.

  So here’s my secret to startup failure — fail fast, fail cheap, and fail happy.

  Sonia Lin

  January 2014

  EntrepreNos.com

  WHO THIS BOOK IS FOR

  This book is for those who want to change the world and need a better idea of what a startup life is about — besides the story of a garage and a bunch of college kids the world is feeding them. While there are many rewarding, successful career paths out there that are equally demanding, those who choose this path deserve a salute for the possibility of no reward and a tumultuous life waiting ahead. This book is so they know it can really be that cool, not because they are going to rule the world, but because it’ll probably suck, and they’ll still power through it and make a difference.

  This book is also for those who have been on an entrepreneurial journey that turned out less successful than expected. As the book is based on the belief that long-term sustainability is the real game, not the short-term validations that are more noticeable, it reminds them they are on the way to their big break and they are not alone. This book will give them a new perspective on many funny and trivial things in a startup life that at times can seem like life or death.

  This book is also for those in the startup world who want to be happy. While there are many sources of happiness, the one stressed in this book is the one that cannot be messed with — physical and mental health. Health is what helps sustain people with reason and purpose, what makes them logical with perspective, what makes them smart with humanity. I argue it is the thing that produces way more positive results in the long term than any benefits or recreation facilities in the company, and ultimately makes the distinction between lines of code and a true innovation that changes the game.

  HOW TO USE THIS BOOK

  This book is best enjoyed when randomly stopping at a section or page that will give either inspiration or warnings when one’s deep in the woods. This book is not a step-by-step guide to creating a business, failing a business, or accomplishing anything. The chapters that describe different aspects of a startup life do not follow any particular order, as they are things to consider no matter at what stage one is in the startup life.

  This book serves as a reminder of the potential pitfalls of one’s startup life, and is suitable for any phase of a startup, and any kind of a startup. It can sit on one’s desk as a casual read — at the risk of finding out the startup matches all symptoms when it’s too late to make one’s way out.

  Last but not least, this is a book for one to laugh. It can sit at the startup office as a convenient warning for a volatile colleague who needs a subtle way of hearing of the need to regain balance — at the risk of triggering more danger because that person is likely to yell, “I DON’T HAVE TIME!”

  HOW THIS BOOK IS DIFFERENT FROM

  ENTREPRENO’S, THE WEBCOMICS

  While the book germinated from the webcomic series EntrepreNo’s: Secret to Startup Failure, which is well-known among the startup community for conveying the humor and ironies of the startup life, this book is the pro version of the comics, and serves three purposes:

  It’s relevant

  The book takes on common themes in a startup life where varying levels of failures may exist, offering everything from a productivity boost to working environment tips, which are not only more relatable, but also no less important than big strategy talk to the sustainability of one’s startup life.

  It’s deep

  The book is intended to lend insights into a startup life that is captured in snippets in the comics. While the humor only makes it more enjoyable, the lessons implied are not to be overlooked; here they are explained in full.

  It’s logical

  The book focuses on various aspects of failure and explains why understanding them is equally worth one’s attention. It not only points out areas where failures potentially occur, but also recognizes areas where it’s okay to fail to meet one’s unrealistic standard in order to achieve long-term success.

  Chapter 1

  Getting Ready

  What one absolutely needs to know about starting up a business

  Know Thyself

  Forget other things that they all say are important to start a business — enough capital, connections, education, and so on. They will be figured out if you get one thing figured out first: yourself.

  One may wonder why this even worth mentioning — ‘Why wouldn’t I know myself? If not, who would?” However, today’s workplace is mostly constructed upon people’s expectations of the role one plays, not so much about who that person really is. Name any role and there are expected attributes attached to it — consultant: eloquent and diplomatic; engineer: analytical and factual, and so on, which we call professionalism. Coupled with the blurring line between the workplace and personal life, one may end up spending more time complying to the expectation than being oneself to the point that one’s preferences and aspirations get buried into the day-to-day activities coming into the role or multiple roles one plays.

  Starting an entrepreneurial journey means you’re adopting a role free of a lot of constraints and expectations from a conventional job. Also, if this is a full-time venture, you’re blessed with a wealth of time that even the wealthiest and most successful person cannot have. What does this mean?

  That means you’re responsible for defining everything. What is the best use of the unique skillset that you know the best? Which areas do you need to hire pros for, and what can you slap together by your own? What would you need to work on to truly own that area? What working conditions do you thrive in? How much work is too much for you? How long without adequate sleep and food can you stand while staying reasonably lean and frugal? Who would you enjoy working with, or maybe it’s better to be on your own? Chances are that one has never been pushed hard enough to learn all this when being employed, as a lot of variables were fixed. Now the entrepreneur has to define all the conditions out of a sea of uncertainty.

  Tip:

  Check out the book Identity Economics: How Our Identities Shape Our Work, Wages, and Wellbeing by George Akerlof and Rachel Kranton, which is about how people make choices based on who they want to be, instead of economic incentives alone; it also explains how people submit to the norm of the group they belong to, or try to be part of, and suffer from the resistance to it.

  Besides, clarifying one’s motivation for starting a business could help narrow down the limitless options one is overwhelmed with. Some want to be king, some want to be rich, some want freedom, some like to invent.

  One’s preferences and motivation may not be entirely clear until going further down the entrepreneurial path. Along the way, there are distractions, as well as possibilities, that implore the entrepreneur to look within with deeper understanding. Before starting the journey, it’s important to make time to ask oneself, “What makes me happy? Why am I doing this?”

  Besides that, happy starting up. Seriously.

  Chapter 2

  Impressions vs. Reality

  The startup industry has become the new entertainment industry, where those who make it are glorified as stars and featured on media, with their valuations skyrocketin
g overnight. With success stories like these, it’s tempting to associate the startup industry with glamor and an indulgent lifestyle.

  While it’s up to every individual to decide how to live off their success, coming to the startup scene out of the motivation to be treated like a rock star will most likely lead to disappointment, as the strain on resources before a reliable revenue stream is established is more likely to require austerity.

  The End of the Tunnel

  Everyone’s heard that startup life is intense, crazy, and inhumane. However, all this has to pay off somehow, right? Money-wise, maybe, but there’s a great chance of startup founders and employees working their butts off only to find wilderness at the end of the tunnel.

  Aside from the uncertainty of success, normal friendships might be hard to hang onto when startups go by a different norm that seems like a different world than the outside 9-to-5 life. Once startup founders succeed, friends flock to them all of a sudden as it’s already hard enough for these startup people to surface from the dungeon, let alone to finally come out in glory; if they don’t make it, they’re probably forever forgotten. Either way, they’re already out of the loop in having conversations with normal people, and even great friendships can hardly sustain a life spent in this wonderland called the startup world.

  Friendship

  Networking

  Compared to college friends to party with, the folks entrepreneurs run into at those startup meetups may be ones they’d want to build relationships with on this bumpy ride. One reason is that these people share common themes and issues faced in building a startup, another being that the startup circle is a small, exclusive one, making it a supportive community. The open-source culture in Silicon Valley might have had its influence, which then shaped how startup people connect and collaborate on ideas.