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Startup Opportunities

KNOW WHEN TO QUIT YOUR DAY JOB


Second Edition







Sean Wise and Brad Feld









Wiley Logo











To Amy and Marisa,
our wives, who are by far the best opportunities we have ever invested in

Foreword

“Dear Chris. I have an idea that will revolutionize a $34 billion industry . . .”

Do you know what that is? An email I will never open. No matter how elegant the prose that follows, I see a snippet like that in Gmail and immediately hit Archive.

Why? As you’ve heard me say for years, “Ideas are cheap. Execution is everything.”

At some point, each of us has had that moment where we say, “Wouldn’t it be cool if . . . ?” Every single human being is capable of churning those out. In fact, I am certain some of you once thought, “Wouldn’t it be cool if I could push a button and have a car and driver show up?” “Wouldn’t it be cool if people could rent out their houses for just a couple days at a time?” “Wouldn’t it be cool if there were an API for payments?” “Wouldn’t it be cool if you could make phone calls and text into your app by using just a little bit of HTML?”

You came up with those ideas, so why aren’t you a billionaire founder on the cover of a magazine? You even bought the endearingly vowel-free domain name, so why aren’t you going public?

Because all the value, all the magic, all the accomplishment, and everything else that matters in entrepreneurship comes in the grueling months and years following the “Wouldn’t it be cool if . . . ?” question.

Since I started making seed investments in 2007, I have been obsessively focused on founders. I spend tons of time with them and go deep in the areas I know well. I never worked on Wall Street or at P&G, and I suck at Excel. So, if we team up, I’m not your supply chain manager or ads optimizer, nor will you catch me estimating Q3 sales five years out.

If we work together, I am there to help you make your product easy and real.

Back in the day, it was expensive to start building a company. Software was proprietary, founders had to buy pricey servers, and they even had to run their own equipment racks in a speedy data center. All of this meant entrepreneurs needed to raise lots of money before they could build anything.

The result? Ideas were splayed across 60-page business plans written by investment banking trainees. Aspiring CEOs were forced to run the investor gauntlet and have every assumption questioned. Hand-wavey bullshit artists with dog-eared copies of Getting to Yes and Starting with No on their genuine faux leather coffee tables drove the painstakingly Socratic process.

Today, with open source, AWS, GitHub, and coffee shops with free Wi-Fi, there are few barriers to taking an impulse and slapping some code on it. Just $99 will get you a solid logo and smooth-looking homepage that makes it look like you know what you’re doing. No more professional networking connections needed, no fancy B-school degrees, and no slick-talking pitch doctors. These days, builders gonna build.

Raise a glass to the democratization of it all! And best of luck to all the now unnecessary investment bankers with incredible PowerPoint and personal grooming skills who have since moved back to New York City to apply their talents to some predatory lending scheme or mass layoff.

But the downside? Too many of you who are founding stuff are skipping the part where smart people beat the shit out of your idea over and over again before anything gets built.

When I first got into this investing business full-time, I was holed up at Brickhouse on Brannon in San Francisco hearing back-to-back pitches. Small teams who could show me live code were impressive. I loved being able to play with a site or an app rather than merely considering a hypothetical.

Yet, almost everything they showed me was irretrievably misguided from the get-go. I met hundreds of entrepreneurs who didn’t even know their own competitive landscape, let alone have the ability to describe to me in plain English why they would win the space. It was devastatingly clear: They hadn’t done the intellectual work that would be the foundation for everything that came next.

In 2008, I’d had enough of these frustrating conversations, so my wife and I moved to Truckee, a small mountain town near Lake Tahoe. Our thesis was that instead of running from coffee to coffee, we’d identify the most intriguing minds in startups and invite them up to our house for weekends. We would go deep with the founders whose thinking challenged ours. Whether we were skiing, hiking, cooking, playing music, or snowshoeing, we were also spending that time batting around visions and predictions and controversial points of view. We would sit around for hours in our hot tub, which soon became known as the “jam tub.” For days at a time, we just jammed on ideas, pushing one another’s reasoning, testing assumptions, and forging moments of clarity and inspiration.

We soon realized that this worked elsewhere as well. Whether we were in Austin, San Francisco, Montana, New York, Paris, Oxford, Boulder, or Vancouver, making time for meaningful group discussion was not only the most fulfilling way to spend time, but it was leading to more genuine friendships and, ultimately, much better ideas across the board.

So who was in those jam sessions? Founders from Twitter, Instagram, Twilio, Uber, Lookout, Stripe—you get the picture. Sure they are legendary companies today, but consider what those early jams were like. For example, as obvious as Uber may seem today, extensive creativity, original thinking, and robust debate were necessary to hone in on the real problems in the industry and focus a solution to build.

These great entrepreneurs didn’t just come up with a great idea. They started with a notion and bounced it around a lot before ever starting up the business. Who they bounced it around with was vital. Early co-founders, advisors, friends, and mentors made a huge difference. What they did with the idea mattered. If they just sat on it, it died. But if they ran around and talked to a bunch of prospective customers or users, it got better. If they actively listened to feedback and incorporated some into their plans, it got even better.

The most successful founders are listeners, thinkers, and tinkerers. They are iterative, reflective, and rigorous. They passionately believe they are right but enjoy when their assertions or conclusions are shredded. The very best feel that yes is boring, and they thrive when wrestling with no.

So take that cute, naive idea of yours and throw it to the wolves. Let your friends slap it around. Ask your peers to tear it up. Meet with fellow entrepreneurs and invite them to bury it. Take what’s left after your mentors spit it out and head back to the whiteboard. Stay up all night jamming. Do this again and again and again, and you’ll realize why founders of billion-dollar companies may be lucky, but their success is never an accident.

I hope to see your name among theirs soon.

Chris Sacca

Montana

March 2017

Preface

Entrepreneurs dream of the magical moment in the creative process when they have a flash of clarity about how to solve a problem or make an innovative product. They often have an interesting story about this moment, and the origin stories of some successful companies have become legend. Yet, this moment of clarity often obscures the massive amount of work required to go from an idea to a real startup. From the outside looking in, a great company appeared out of nowhere. But the entrepreneur knows differently and remembers what had to happen to get from the idea to even the most embryonic startup.

As investors, we hear a simple question from entrepreneurs multiple times a day: “What do you think of my idea?” Sometimes the idea is well formed; often it is vague. Some have already been prototyped, others are just a few sentences in an email. Some have been thoroughly researched by an entrepreneur with deep domain knowledge, others are something completely new and different that the entrepreneur is exploring.

While it is easy to have an idea, it is incredibly hard to translate that idea into a successful business. The startup phase of a company requires a wide variety of activities to go from idea to successful startup. In the past few years, many books have been written about this process, including foundational ones such as The Lean Startup by Eric Ries, The Startup Owner’s Manual by Steve Blank, and Disciplined Entrepreneurship by Bill Aulet.

Nevertheless, we continue to hear some version of the same question over and over from aspiring entrepreneurs: “Is my idea any good?” Sometimes it’s phrased as “How do I know if my idea is good?” or “When I have an idea, how do I know if it’s good?” Often, this morphs into “I have the following three ideas. Which is the best one?”

Many of these entrepreneurs aren’t ready to stop what they are doing and dive all the way in to chase their new idea. Some have full-time jobs and are trying to figure out how this entrepreneurship thing works. Others are playing around with multiple ideas at the same time and trying to pick one or are stuck in the ideation phase, coming up with ideas and looking for external validation, but are unwilling to commit to working on a specific idea yet.

Ultimately, they are asking some form of the question “Will there be enough demand for this product that people will use it and pay for it?” Even after being pointed at books and approaches like the Lean Startup, they still have questions about whether their idea is any good.

It’s not a simple question to answer. Most successful companies go on a long and winding journey to find the answer. A founder used to write a comprehensive and tightly structured business plan that evaluated all aspects of the potential business. This document took hundreds of hours to write and tried to set up the theoretical case for the business without testing anything.

While business planning isn’t obsolete, the business plan is. It has been replaced by methodologies such as the Business Model Canvas, Business Model Generation, Lean Startup, Lean Launchpad, and Disciplined Entrepreneurship. Each of these methodologies uses a structured, experimental approach with quantitative feedback loops from potential users, customers, and partners to evolve an idea to a foundation upon which a startup can be built.

But that still leaves us with the questions “Is the idea any good?” and “Should I pursue this idea?”

It is possible to get to a better starting point if you spend some time in the opportunity evaluation phase. Before you even begin testing the idea and building on it, there are some fundamental questions you can answer. Through our work at Techstars, Dragons’ Den, and as early stage investors, we have found ourselves asking entrepreneurs the same set of questions repeatedly. While many of our conversations were short and detailed answers often weren’t forthcoming, we found that even the simple act of being asked the questions often helped the entrepreneur improve the idea.

It is not enough that you think your idea is a good idea. Others need to agree with you so that they will work with you either as partners, employees, investors, advisors, or customers. However, many entrepreneurs are afraid to share their idea with others for fear that it might be stolen. But as you’ll see in a moment, ideas need oxygen. In addition to engaging supporters and getting feedback, opening up ideas up and sharing them with trusted advisors as you are having the ideas can help evolve these ideas into something that you can build upon to create a startup.

Our goal with this book isn’t to replace existing methodologies. Instead, we want to complement them by giving you a context and a set of tools to help you evaluate your idea before you start putting any meaningful energy into it. Think of this exercise as the precursor to the Lean Startup or the Lean LaunchPad methodologies. We want this to be the book you read before diving into one of these methodologies, especially if you are a first-time entrepreneur.

The audience for this book isn’t just existing entrepreneurs or investors but a much larger class of readers—those who have yet to quit their jobs and take the leap into entrepreneurship. Hopefully, we will help you pick a better idea to build a startup around.

Trust Me, Your Idea Is Worthless

by Tim Ferriss1

Earth-shattering and world-changing ideas are a dime a dozen. In fact, that’s being too generous.

I’ve had hundreds of would-be entrepreneurs contact me with great news: They have the next big thing, but they can’t risk telling me (or anyone else) about it until I sign some form of idea insurance, usually a nondisclosure agreement (NDA). Like every other sensible investor on the planet, I decline the request to sign the NDA, forgoing the idea, often to the shock, awe, and dismay of the stunned entrepreneur.

Why do I avoid this conversation? Because entrepreneurs who behave this way clearly overvalue ideas and therefore, almost by definition, undervalue execution. Brainstorming is a risk-free, carefree activity. Entrepreneurship in the literal sense of “undertaking” is not. Strap on your seat belt if you’re signing up for a startup. It’s a high-velocity experience.

If you have a brilliant idea, it’s safe to assume that a few very smart people are working on the same thing, or are working on a different approach to solving the same problem. Just look at the number of different travel apps on your iPhone or the number of diet and exercise sites on the web for an example of this.

Overvaluing the idea is a red flag, particularly in the absence of tangible progress. Sure, I miss out on investing in some truly great ideas with this attitude, but that’s okay with me; I don’t invest in ideas. Nor does Warren Buffett. I’ll lose less money than those who do. I can largely control my downside by investing in good people who, even if they fail this go-round, will learn from mistakes and have other fundable ideas (ideas I’ll likely have access to as an early supporter). I do not have this advantage when investing in ideas.

One popular startup dictum worth remembering is “One can steal ideas, but no one can steal execution or passion.” Put in another light: There is no market for ideas. Think about it for a second: Have you tried selling an idea lately? Where would you go to sell it? Who would buy it? When there is no market, it is usually a very sure sign that there is no value.

Almost anyone can (and has!) come up with a great idea, but only a skilled entrepreneur can execute it. Skilled in this case doesn’t mean experienced; it means flexible and action-oriented, someone who recognizes that mistakes can often be corrected, but time lost postponing a decision is lost forever. Ideas, however necessary, are not sufficient. They are just an entry ticket to play the game.

Don’t shelter and protect your startup concept like it’s a nest egg. If it’s truly your only viable idea, you won’t have the creativity to adapt when needed (and it will be needed often) in negotiation or responding to competitors and customers. In this case, it’s better to call it quits before you start.

Your idea is probably being worked on by people just as smart as you are.

Focus on where most people balk and delay: exposing it to the real world. If you’re cut out for the ride, this is also where all the rewards and excitement live, right alongside the 800-pound gorillas and cliffside paths. That’s the fun of it.

David didn’t beat Goliath with a whiteboard. Go get among it, and prepare to bob and weave.

Note

CHAPTER 1
What Is a Startup?

The word startup has become an increasing part of the popular lexicon in the past few years. While it has been around for a while, it has recently become ubiquitous for those discussing entrepreneurship and new company creation. But not all new companies are startups.

There is a big difference between two types of entrepreneurial endeavors: (1) local businesses, also called SMEs (small- and medium-sized enterprises) or lifestyle businesses; and (2) high-growth companies, often referred to as startups or gazelles,1 a term first used by David Birch in 1979 and refined in 1994 to refer to companies with a minimum of $1 million of revenue that were at least doubling in size every four years.

Local businesses are what they sound like. These are the businesses that you find in your city whose customers are close to the business, such as the corner grocery, local bookstore, nonchain restaurant, or locally owned gas station. Occasionally these local businesses start to expand and turn into multigeography businesses, resulting in a large enterprise, but many are local businesses for the duration of their existence.

In contrast, high-growth companies rarely have a local focus. While they are often started in one location, and, at inception, usually only have a few people involved, the founders of these companies aspire to grow quickly, independent of geographic boundaries. Their customers are all over the world, and regardless of whether the company ever expands geographically, the business is rarely constrained by geography.

In the United States, until recently, all startups were referred to as small businesses. This is a historical artifact of the U.S. Small Business Administration, commonly referred to as the SBA. Until 2010, the U.S. government didn’t differentiate between types of entrepreneurial businesses. Thus, the SBA was helpful to some companies but useless to many others, especially the high-growth ones. Government at all levels (federal, state, and local) didn’t understand the potential impact of startups as a separate class of company, so all small businesses were lumped together.

In 2010, President Barack Obama announced Startup America2 and thus the word startup catapulted to the forefront of everyone’s mind. Through the support of the Case Foundation and the Kauffman Foundation, the Startup America Partnership was launched. This was a private partnership that executed a three-year plan, chaired by Steve Case (the founder of AOL) and led by Scott Case (unrelated to Steve), to define, support, and spread the message of startups throughout the United States.

Today, a startup is recognized as something distinct from a small business. For the definition of startup, we turn to the czar of customer development and grandfather of the Lean Startup movement, Steve Blank, who has coined what we think is the best definition for the term: A startup is a temporary organization formed to search for a repeatable and scalable business model.3

Let’s break down Steve’s definition and explore the different parts:

Steve says this in another delightful way: “A startup is not a smaller version of a large company.”4 Instead, a startup is a series of experiments in search of a scalable business.

How to Use This Book

Our goal with this book is to help you figure out in advance which ideas are worth experimenting with. While this book is intended to be read from beginning to end, we have organized it so that you can read each chapter independently. We want to provide you with a structure to evaluate the idea you have in a formal and comprehensive way while allowing you to quickly think about the key issues that will come up.

We aren’t trying to create a new methodology for starting a company, nor are we trying to replace approaches like Lean Startup. Instead, we are taking a step back and engaging earlier in the process. This book is intended to be read before you read The Lean Startup or participate in a Lean LaunchPad process. We’ll provide plenty of context around different approaches and resources for getting your business off the ground, but our primary focus is in helping you with the prestartup, or the opportunity evaluation phase, when you are still deciding whether to put energy into the startup.

In addition to our perspectives, we’ve included examples from entrepreneurs and the investors who funded them at very early stages. Many of the examples are of companies that have grown substantially. By going back to a point in time near their inception, you can get a sense of how and why the entrepreneur and the investor decided to pursue the opportunity. Other sidebars include expert analysis from practitioners or academics of some of the more important elements in the opportunity evaluation process.

Our primary professional focus is in investing in high-growth startups. Brad’s experience, through Techstars and Foundry Group, is primarily in high-tech companies. Sean’s experience, through Dragons’ Den (Canada’s version of Shark Tank) and his own investing, is primarily in consumer products. To make this book applicable for anyone interested in starting a company, we’ve used examples from each of these domains.

Who This Book Is For

We wrote this book with first-time entrepreneurs in mind. However, we have received feedback from experienced entrepreneurs that this book has been helpful to them while thinking through their next opportunity.

As entrepreneurship engages a wider range of younger people in our society, we see a dramatic increase in entrepreneurial activities from high school and college students. This book is aimed at them and is intended to be used as a part of an entrepreneurship curriculum.

This book is for educators, particularly those teaching entrepreneurship and opportunity recognition and evaluation courses. If you are a teacher whose students often ask, “How do I know if my idea is worth pursuing?” then this book is for you.

This book is also for friends and family who support the entrepreneur on her complicated and challenging journey. If you are an entrepreneur, you can use it as a source of dialogue with your spouse, your siblings, your parents, and your children.5

This book is for fans of Dragons’ Den and Shark Tank. If you have wondered how the judges choose which companies to fund, you’ll enjoy this book.

This book is also for investors, especially angel and early-stage investors, as they try to better understand a new business. In the same way that the entrepreneur can use this book to help shape an opportunity, an investor can also use these concepts to help evaluate an opportunity.

Most of all, the book is for all those who have a passion for entrepreneurship, especially those of you who know that only the very best opportunities deserve your blood, sweat, and tears. Ideas may be worthless, but your time, energy, and focus are not. Friends only let friends work on great opportunities.

Notes