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Introduction

Why This Book?

I sat in the upstairs dining area of the original Giordano’s Deep Dish Pizzeria in Chicago, surrounded by signed pictures of celebrities, athletes, musicians, actors, politicians, and I’m fairly sure, a few local gangsters. The world-renowned pizza, smothered in fresh tomato sauce and layers of cheese, turned out to be nearly as deep as the conversation I was having with my friend, Greg. We were both entrepreneurs—me having started my first multimillion-dollar media agency at only twenty-six, and Greg having built a successful venture in Japan around the same time. My agency did everything from logo and branding design, radio and TV commercials, and trade shows, to heavy back-end database work. We specialized in interactive multimedia and rich internet application development. I even ranked second on an international certification for multimedia development. I loved being on the cutting edge of technology. I still do. It turned out for Greg and me that running our businesses was a part of our genetic makeup—the thought of not being some kind of entrepreneur just never occurred to either of us. If you’ve picked up this book because of the title, you likely know this feeling well.

Over the course of our dinner that evening, we wondered aloud, “Why doesn’t everyone start their own business?”

For Greg, a guy whose monthly checks were bigger than most people’s annual salaries, his entrepreneurial motivation was simple: “The reason I do my own thing is that I’m too lazy to do it the traditional way. I have to figure out a better and faster way to do business, so I don’t have to work as hard as everyone else.”

We both laughed heartily at the joke, but it held a golden nugget of truth: there is a better way to do business—to work smarter instead of harder. It is possible to start a company without the traditional years of headache and heartache.

And that’s what this book is about: teaching you a better and faster way to create explosive growth in your business.

When Giordano’s Pizza was founded in 1974, the Dow was at 580, and Warren Buffett was telling everyone, “This is the time to start investing.” We didn’t have the internet, so there wasn’t the wealth of knowledge we have now about the principles required to start and grow a successful business. Without a relationship with someone like Warren Buffett, most startups stayed small or floundered. Take the story of Giordano’s: two brothers, Efren and Joseph, took their mother’s famous “Italian Easter Pie” recipe from Torino, Italy, to the US and opened their first restaurant. The pizza was so good they called the recipe a “sacred tradition,” and I can attest it is one of the most savory pizzas I’ve ever eaten. The pizzeria received accolades from the New York Times, Concierge Magazine, CBS, NBC, and others. No question they had a recipe for an incredible pizza, but what about one for an incredible business? How many mistakes did they have to learn “the hard way”? How many sleepless nights did it take until they finally made it? If only their mother had left a “success tradition” recipe to follow as well.

Having a personal success recipe is a superb way to think about this book: a linear plan for building an amazing business and avoiding the painful and slow slog through the trenches, pitfalls, and numerous rookie mistakes. Had I been able to share this recipe with myself twenty years ago, I might have avoided several blunders launching and growing my first multimillion-dollar company. Viewed from the outside, I was winning awards, filing patents, working with most of the Fortune 500, expanding internationally, and being written up in magazines as one of the 40 under 40 entrepreneurs to watch. On the inside, however, I was nervous about how I would make the next payroll. I wouldn’t wish that amount of stress and hand-wringing on anyone. And since I can’t go back and mentor my younger self, I want to share my entrepreneurial recipe with you—a recipe grounded in principles and tested in the real world, that you can follow to accelerate revenue and profits.

There is a better way to do business today and you don’t have to know Warren Buffett to take advantage of it. With the right mix of motivation, skill, and team members, it doesn’t matter if you’re crafting the world’s best pizza or cooking up your own entrepreneurial dream.

And yet entrepreneurship is fraught with peril: 30 percent of all businesses in America fail in the first year and 50 percent fail in the first five. The truth is most businesses don’t fail—entrepreneurs quit. The reason they quit is because the entrepreneurial process has sixteen pitfalls baked right in (pun intended). Each one of the pitfalls is an inflection point toward wild success or shutting the doors. Most entrepreneurs who have made it past the five-year mark have figured out how to navigate at least half a dozen pitfalls. The ones that make the news because of rapid growth fly past these pitfalls masterfully. That’s what this book is about.

Like Mama Giordano’s “Sacred Tradition,” the recipe for navigating past these pitfalls didn’t come from the halls of an elite culinary school (a.k.a. an MBA) but the hard-won experience of trial and error in the real world (mixed with a few years leading the global marketing effort for one of the world’s premier leadership companies). And yet nearly all entrepreneurs (including myself) contend with these pitfalls every time they set out to build a new business.

In my case, I remember thinking my business was special…that I was creating something that had never been done before. It was easy to take that belief and assume it would be enough to fuel the momentum to succeed. Destiny, here I come!

But it wasn’t so easy, despite my business truly being one of a kind and with a modus operandi that was even more unique. Very few companies around the world were creating interactive media the way we were, and the creators of the software we used said they’d never seen a more advanced Rich Internet Application (RIA). So, with a new patent and industry awards under our belt, it makes sense that it would all have fallen together perfectly. Only it didn’t, and I wasn’t prepared for the price I had to pay to make it all happen.

Later, as I reflected on this experience and the experiences I was seeing as a consultant, I could see a pattern at work: my start-up clients were experiencing the same pains I had pushed through years before. For example, they would typically hit an invisible ceiling within the first couple of years. They were experiencing the same personnel issues within the first few years. My clients were trying to find the path to rapid growth in the same way I had experienced it. They found similar challenges at each financial milestone (such as five, ten, and twenty million in revenue), as well as other inflection points that I had experienced—and often in the same order.

If you feel that pull toward starting your own business and are ready to jump into the start-up waters (or, having already jumped in, you’re feeling you may be in over your head), I’ve written this book for you as a:

•Visionary looking to take your idea, product, or service and turn it into a viable business

•Business owner looking for rapid growth and revenue

•Founder of a start-up looking not only to survive but thrive in the days to come

The Paradox

“No is the amplifier of Yes.”

—Crawford Cragun

“Entrepreneur’s Paradox: You have to give up being the best in the world at building your product to be the best in the world at building your business.”

At the core of this book is a paradox: what got you into business is the very thing that will actively prevent you from succeeding in business.

That’s right—you, the entrepreneur, are typically one of the most proficient people in the world at a particular skill, craft, product, or idea. You’ve thought of or created something that has never been done before, especially in the way you’ve conceived it. When others find out about how great your idea is, they ask for, even demand, your product or service. In fact, they often love the product or service so much they compel you to start a business repeating that expertise over and over again. It can be thrilling knowing you can contribute to the world and seeing how many people appreciate what you do and the way you do it. But such a passion can create its own kind of trap. In the beginning, everything feels exciting and the business appears to be thriving (if it weren’t for this honeymoon phase, I’m not sure anyone would start a business). But that newfound freedom can quickly shackle you with grueling hours and endless to-do lists. And where you thought you would find personal and financial independence, there’s stress, erratic cash flow, and bills instead.

This book will show you how that initial spark of brilliance and entrepreneurial spirit can be the very thing that inhibits entrepreneurs from achieving their goals—regardless of industry or business type. But by recognizing and working through the chapters in this book, you can learn to work through the Entrepreneur’s Paradox and experience growth equal to the passion that gave it life.

Who This Book Is For (And Not For)

This is not a management technique book. I have not aimed it at large corporations or start-up founders who have already had multiple equity events or an IPO. Although many in the corporate world will find this book helpful, I’ve written it for those in the entrepreneurial trenches. I wrote this book for start-up entrepreneurs looking for a way to create rapid growth and break through to the next level. It is for founders of companies typically in the first two to ten years of business. And it is for first-time entrepreneurs needing a tool to avoid many of the missteps that doom new ventures. As a result, after reading this book, you will walk away with:

•Proven ideas for your company to achieve rapid growth

•Life-changing directions to follow as a new entrepreneur

•Awareness of how you can either inhibit or energize your business goals

•A clear path to navigate past the pitfalls standing between you and success

You’ll also find this book includes links to many online resources, calculators, infographics, and tools for the “Overcoming the Pitfalls” sections at the end of each chapter to help you self-assess and move your business forward. Some principles relate to the business, and many relate directly to you as the entrepreneur. And by the way, if you’re reading this well above your mid-twenties and think it may be too late to start your entrepreneurial journey, take heart. According to the Wharton Knowledge Group, you’ll enjoy some advantages that come with age and experience.1 It’s both never too early and never too late to answer the call and take this journey.

So, get ready to dig in and go deep as an entrepreneur—not unlike digging in and going deep with that Chicago pizza. Because it’s one thing to have a world-class offering, and quite another to build the world-class business around it. Pull up a chair, take a seat at the table, grab a slice, and let’s get to it.

The Entrepreneur’s Paradox

“Man conquers the world by conquering himself.”

—Zeno of Citium

I awoke at four thirty with the grid pattern of my keyboard imprinted on the side of my face. Sleep-deprived and groggy, I was the only one left in the office. The keyboard had become my unintentional pillow repeatedly for nearly three days, and I found myself in a kind of bleary-eyed delirium. I wanted to sleep, but there was too much work to do.

I’d started my new company to find freedom, wealth, and excitement, but instead I found myself in a prison of my own making. My entrepreneurial dream had been marked by insane work hours, sleepless nights, no after-hours teammates, grueling deadlines, and difficult clients. I often wished I had more time for my family, church callings, writing and playing music, and pushing harder on triathlons.

I’d traded a really great boss at Ancestry.com for a crack-the-whip, ruthless tyrant: me! I’d also exchanged normal work hours, stable cash flow, and time with my family for marathon work sessions away from home, crazy amounts of stress, and erratic cash flow. This prison of my own making—my personal gilded cage—held a single sign over the barred door which read, “Entrepreneurship.”

I pushed through that morning to finish the project on time, staying focused on the usual high quality it demanded.

From the outside, my business looked like it was succeeding. I’d received the “Entrepreneur of the Year” award from the Chamber of Commerce and was listed as one of the “40 under 40” taking advantage of the fast-growing economy in the Silicon Slopes (a technology hub at the base of the Wasatch Mountains in Utah). I had been written up in magazines like Utah Business and Business Q and was recognized as one of the leading interactive website and multimedia developers in the world. A professional international certification ranked me second in the world in Adobe Flash. All the trappings of success, right? Turns out, not so much.

How did I get here?

I didn’t have the answer that morning, and it took several years and more than one painful lesson (including losing my first company to a corporate coup) to help me see how I’d trapped myself despite all my talents, passions, and work ethic. Once I’d lost the company, I pushed the reset button and reevaluated my world view. I changed my paradigms and took a hard look at my professional life from a more objective point of view.

That’s when the epiphany came. I’d been caught in a paradox—the Entrepreneur’s Paradox, to be more precise. In short, I was good at what I did—really good. But this was the reason my business wasn’t succeeding.

Think about it for a moment. If you’re highly skilled at something, people view you as an expert and want your hands-on efforts. Clients see you and not the business as the most expedient path to that “magic” you sold them in the first place. My clients were no different. They wanted me, Curtis. They weren’t really interested in the services of my business. I had employees, tools, and a few systems in place, but our corporate clients wanted me, personally, to do the work. After all, I had been the one doing the work for other clients in the past. As a young and inexperienced entrepreneur, I had made the mistake of assuming that “doing the work” and “growing the business” were the same thing. But they are as different as night and day.

With this new (and hard-won) insight, I realized that, if I wanted to succeed in business, I had to stop being the sole expert, the sought-after specialist, the best in the world. I had to give up part of my identity.

The Entrepreneur’s Paradox applies not only to me, but also to countless others who attempt the leap from world-class expert and specialist to business owner. You simply can’t be the best in the world at your craft while being best in the world at running a business. As the saying goes, “No man can serve two masters.” And that’s exactly what I, and most entrepreneurs, have tried to do.

Our personal passions are often at the heart of a new business venture. One of my friends is a chocolatier because of his love for chocolate. Another started a travel expedition company because she loves to travel and has a true talent for immersing people in unique cultural experiences. Another friend started a video game company because of his love and talent for gaming. Still another started a mobile app company because he has a passion for clean design and journaling and wanted to help people around the world tell their stories. Passion is great fodder for the entrepreneurial engine.

In the years between that first business epiphany and the writing of this book, I’ve coached many passionate entrepreneurs. Without fail, they all talk about how unique their business is—that they have the secret sauce that will differentiate and propel them past their competitors. And it’s often true. But what tends to always be true is the timeline these entrepreneurs will go through. Their stories are almost always the same and move in predictable chapters and verses.

Entrepreneur’s Island

All entrepreneurs start somewhere else in life. They usually start at an established company. Most get a little taste of entrepreneurship when they take a small break from the “normal” world. Instead of waking up each day to go to the same office and see the same boss and do the same thing day in and day out, they get a taste of something new and exciting, tapping into their skills and being rewarded emotionally and monetarily. It’s like taking a vacation to a tropical island where breaking waves offer adventure and pristine white sand beaches and which seems like a little piece of heaven. It’s exhilarating because it represents many of the things we enjoy and are passionate about. It comes with a rush of new experiences and we are often praised for our accomplishments there, because we are typically very skilled at what we do. Most will occasionally jump to the island for a fleeting moment of thrilling experiences and then bounce back from this “special” world to the ordinary, safe, and comfortable world (i.e., our day jobs). In today’s vernacular, this is often called freelancing, moonlighting, or even having a “side hustle.” Yet, we still feel the pull of this island and can’t wait to go back.

For others, this desire becomes so strong we leave the comfort of the ordinary world permanently—selling our homes on the mainland and moving to the island! At first, it’s a paradise. We wake up whenever it feels nice, set our schedule according to what suits us best, and have fun doing what we love. This is the life! And people really appreciate the artistry with which we build our sandcastles, fish for food, and make the most delicious coconut drinks (i.e., the products or services we offer). Even better, the demand for our products grows.

Then, one day, as we are sitting on our beach chair, we hear a rustle in the vegetation from behind. We turn to catch sight of an alligator creeping out of the jungle and heading straight for us! The alligator threatens our livelihood, peace, and food. Springing into action, we’re forced to wrestle it away from our beautiful beach and the delicious fish cooking over the fire. Not only will this beast crush our castles in the sand, but it will deprive us of food and all we’ve accomplished. The alligators show up in the form of unrealistic deadlines, unplanned emergencies, keeping customers happy, cash flow issues, and a host of other activities that require our time, energy, and focus. We didn’t realize life on Entrepreneur’s Island came with a cost! When we saw the shimmering blue ocean waves, we had no idea there were alligators native to our little patch of paradise.


Over time, more alligators begin to show up. It seems the longer we live on the island and the bigger the fish we reel in, the more alligators we attract. Long gone is the fantasy of sipping drinks from coconuts and basking under the ocean sun. Instead, each day brings a new assault and a greater struggle to wrestle these alligators away. The cost of maintaining life in paradise is to spend a greater portion of each day wrestling these unwelcome intruders. And to make matters worse, it seems that when one gets a bite, it attracts even more!

Fed up and tired of being surprised day in and day out, we decide to find the home of these alligators and deal with the problem head-on. That means leaving the beach and entering the jungle. If it can keep our beach safe, it’s worth the effort. Trudging through the dense brush, we find the swamp the alligators call home. There’s little choice but to jump in and start wrestling, and this is how we spend the majority of the day: resolving client concerns, answering emails, returning phone calls, reconciling bank accounts, filing taxes, finishing projects, fixing projects, looking for new projects, scheduling travel, building a website, invoicing…the list of alligators is nearly endless. But we wrestle them one by one, even though it means returning to the beach later and later each day. What’s strange is that we actually become quite good at wrestling alligators and keeping them off the beach, even though it’s a beach we see less and less of.

This isn’t where we wanted to be when we left the comfort of a stable job. We wanted to be in a place of freedom, flexibility, wealth, praise, and excitement. Well, we got the excitement for sure. We’ve entered our personal version of Groundhog Day: wake up, wrestle alligators, go to bed, repeat. It’s exhausting and doesn’t feel like that magical island we sacrificed everything to move to.

Draining the Swamp

“Alligators: The urgent demands and important tasks incumbent to running your business and which can’t be ignored.”

Entrepreneur’s Island is made up of an idyllic beach where you wanted to spend your time, a thick jungle with a swamp full of alligators you were forced to wrestle, and several tall mountains in the distance you hardly noticed (if at all). So after months (or years) of wrestling alligators, it’s time to make a choice: swap your title from “entrepreneur” to “alligator wrestler” and learn to accept the reality of your work life, or find a smaller section of beach, less inviting to alligators, where you can downsize and go back to a simple (smaller) life. Or reject both those options and choose a third alternative. For me, this is when the words of my friend Greg started resonating in my head: There is a better way. Stop wrestling alligators.

If you want to stop wrestling the alligators, you must “drain the swamp.” Because, once you drain the swamp, the alligators will leave on their own. But it isn’t easy. As the saying goes, “It’s hard to drain the swamp when you’re always eye-to-eye with an alligator.”

So, how do you break free and escape? First, you have to recognize the why behind your alligator wrestling. And it begins with the fact that you are the expert and that becomes your identity. I’ve seen entrepreneurs hold tightly to being the magazine editor rather than the magazine owner, the brilliant programmer rather than the brilliant business person, the game-changing engineer rather than engineering an incredible company. Most entrepreneurs hold tightly to the identity of being the best in the world at building a product or offering a service, rather than being the best in the world at building a company. But being the expert means you have to be the person performing the tasks every day. People love you for it, and you love the feeling of creating something amazing. But in reality, this is diving into the swamp.

Because you’re the expert and actively engaged in alligator wrestling, you’re essentially doing everything by yourself. Trust me, I get it. I know the feeling of producing something that has never been done before. I know how fulfilling it is to produce something beautiful, creative, and exceptional. The trouble is, as long as you are the one producing the product or service, you have no time to drain the swamp. The way out is to create systems and processes, including training others to create the product or deliver the service as well as you do, so you can create a business equally as amazing as your product. More on that in future chapters.

The paradox is that these talents and skills were what brought you to the beach in the first place. These are the things that served you in creating your company but now are holding you back and keeping you stuck. These are the things you have to let go of in order to be able to take a step back and figure out how to drain the swamp.

A New Identity

Marshall Goldsmith coined the phrase, “What got you here won’t get you there.” In entrepreneurship, what got you here will actively prevent you from getting there. It will be so dominating in your life that you won’t even be able to see that there is a whole new world of possibilities beyond the swamp. It’s time to redirect your passion for the product or service you create and focus it toward building a sustainable business free from nightly keyboard imprints on your face.

Part of changing your identity is acknowledging that you are not your business. Although your business is a living, breathing organism, and has a life of its own, many entrepreneurs will take the identity of the business upon themselves. Here’s an easy survey to assess whether you’ve assumed your business’s identity:

•Did you name the company after yourself?

•Do your bank account and the company bank account share the same number?

•When your business is doing well, do you feel like you are succeeding?

•Is your business defining you?

•Does every success feel like it is your personal success?

•Does every business failure feel fatal to you, personally?

You are not defined by your business, and the healthiest and fastest way to grow your company is to disassociate your identity from the identity of the business. You are a piece of your company. Arguably the most important piece, but still just a piece. If the business were a person, you’d be the heart and often the brains of the company, but you are not the company. Be willing to let the business have its own identity independent of you. Set up a separate bank account. Think about rebranding your company with a catchy descriptive name that is not your own. Surrender the fact that your company can and needs to thrive without your direct labor. With this mindset, you will grow faster, be healthier, and see the results you are looking for.

You must let go of these two parts of your old identity (I am the best in the world at my craft, and me and my business are the same) and take on a new one. I am independent of my company and not afraid to let others take over tasks that are meaningful and important; I am the business builder and no longer the product builder. Instead of you being the most skilled at travel, interactive technologies, programming, guitar building, video games, or whatever you identify with, you’ll need to stop the full-time job of fighting alligators and focus all of your attention on being the business builder—the one who drains the swamp. This means you will need to:

•Build a team. Hire a full-time assistant and other skilled individuals you can offload tasks to. Look into hiring or recruiting interns as well, as many universities provide a mechanism to trade work experience for credit. Many of them can transition to employees as they graduate, and you’ll already have a positive and effective working relationship.

•Delegate responsibilities. Use full-time, contract, and on-call professionals (such as an accountant and lawyer) to engage in their areas of expertise.

•Implement software and systems. Equip tools, systems, and processes so critical parts of the business can run efficiently and without your constant attention.

•Train your team. You’ll need to bridge the gap as the “expert” and help instruct, coach, and mentor your staff to deliver high-quality products and services and deliver premier customer service just as you would.

Taking actions like those listed above will help you shift from service provider and/or product builder to that of company builder. Your charge is to get out of the day-to-day. Make a commitment today to start draining the swamp and never return.

Remember, draining the swamp is a process. It will take time figuring out how to make sure the secret sauce you bring to the business is disseminated to others. Spend your days focused on the bigger picture rather than focusing myopically on the creation of the product or service. For me, in my first company, this meant I needed to stop being the best in the world at building interactive media. I had to abandon that persona and the praise and excitement that went with it. This kind of identity shift is a difficult task. It’s not familiar or comfortable, especially at first. I understand. Yet it’s critical if you are going to take your business to the next level. Because once you’re past the swamp, there are mountains to climb. Remember those mountains on Entrepreneur’s Island you hardly took notice of? That’s where we’re headed next. So come along, we’ve got quite the journey ahead!

The Entrepreneur’s Paradox: Apply the Principle

•Reinvent yourself as an entrepreneur and not just a skilled specialist or artisan. Stop building the product and start building the business.

•Write down the reasons your product is successful, capturing the recipe you’ve used to make it successful, for example:

-I pay attention to detail in my work.

-I think outside the box when creating my product.

-I’m passionate about what I produce.

-I know what my customers want in the product.

•Write out how these principles can apply to your business as a whole.

•Take one of your full workdays and track all the activities you engage in. Write down everything you do and how much time you spend on each. Mark the FEEDING THE ALLIGATORS column for any activity that doesn’t lead to the strategic enhancement of the company and mark the DRAINING THE SWAMP column for any activity that boosts your business strategy.

•With your list of weekly activities in front of you, start creating a permanent “To Don’t” list. Identify at least ten things you will stop doing or will delegate to others so you can free up your time to focus on creating a better business.

-NOTE: If you are part-time freelancing, moonlighting, or running a “side hustle,” you may not have the resources to hire everybody on the list. If you’re making over 10K a year, spend a few hundred dollars and hire an accountant. Then scale from there.

ActivityTime SpentWrestling AlligatorsDraining the Swamp
Sorting mail15 minutesx
Working on my five-year business plan1 hour, 10 minutesx
Arranging travel for upcoming client visit50 minutesx
Create onboarding process for new employees2 hoursx
Payroll1 hour 35 minutesx
Finishing the logo for a new client2 hours 20 minutesx
Create an org chart of positions needed to take the company to the next level1 hour 30 minutesx
Bookkeeping and filing quarterly taxes1 hour 35 minutesx
Meeting with client and revising graphics for website2 hours, 50 minutesx
Formatting spreadsheet to make it look more presentable35 minutesx
Meeting with a mentor or coach for lunch2 hoursx
Identifying a plan to overcome the top three stumbling blocks2 hours 10 minutesx

A printable activity tracker can be found on the web at EntrepreneursParadox.com/ActivityTracker


1 Nov 12, 2. (n.d.). The Average Age of Successful Entrepreneurs Is Actually 45. Retrieved September 14, 2020, from knowledge.wharton.upenn.edu/article/age-of-successful-entrepreneurs.

The Entrepreneur's Paradox

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