Entrepreneurial You: Monetize Your Expertise, Create Multiple Income Streams, and Thrive

PROLOGUE

Why I Wrote This Book

It’s the dirty secret of today’s entrepreneurial economy: being excellent, and even being well known and respected in your field, just isn’t enough.

The internet and our globalized economy have given us the possibility of reaching millions of people, working on our own terms, and enjoying unlimited income potential. But for too many professionals, that’s just not been the reality. Instead, we live in a world where success has increasingly been decoupled from income. In the course of my travels, I’ve run across way too many top-notch professionals who are excellent at what they do, yet struggle to earn what they’re worth. You can be talented and well regarded, but unless you’re very deliberate about the choices you make, you may end up earning little for your efforts.

What went wrong? And how can we reverse that negative trend and reap the potent promise of entrepreneurship? To answer those questions, I interviewed more than fifty successful entrepreneurs, earning high six-, seven-, and eight-figure incomes with solo or very small businesses. This book distills the secrets I learned—practical hands-on advice about how to monetize your expertise and build a sustainable, thriving business in the new economy.

Whether you’re an entrepreneur, an aspiring entrepreneur, or an employed professional seeking to maximize your options, you’ll find in these pages proven strategies that will help you develop new income streams that leverage the work you’re already doing, and open up new opportunities for freedom and flexibility.

The path that led me to write this book started in 2006 when I launched my own marketing strategy consulting business after working previously as a journalist, presidential campaign spokesperson, and nonprofit executive director.

In the early days, I was just happy to be working for myself, from home. My sole focus then was bringing in revenue and getting my business solvent; I took on clients of almost any size for projects of almost any scope. There was the speech I wrote for a nonprofit chairman for $500, the $1,000 communications plan for a government agency, and the multiple times I f lew across the country to do weekend-long trainings for $600 plus airfare (my client was so cheap that on one trip, I had two connections each way). It wasn’t pretty.

I spent the first years of my business hustling fanatically, working long hours, networking face to face in search of business and directly servicing clients on site. As I built my business into a more sustainable venture, I eventually cut out the hundred-dollar projects, and within a couple of years, I was earning a healthy, six-figure income.

But most days I was still stuck in client meetings or driving hours to get to them. I found myself in a common trap for successful entrepreneurs: you’ve built up a business so robust that you don’t have time to do anything but service your existing clients.

I knew that if I kept on the same path, I could continue to grow my business over the years and have a perfectly nice quality of life. In time, I’d go from being thought of as a talented, rising young consultant to being the go-to consultant in my market, and I might even land some of the local blue-chip firms as clients.

But I wanted more than that.

I was frustrated that I couldn’t travel as much as I wanted for pleasure, because I was locked down by client meetings and the expectation (which I’d helped to cultivate) that I’d always be on call. Even though I worked for myself, I didn’t feel particularly free.

I wanted to accomplish two things: to upgrade the clients I worked with to larger companies with bigger budgets; and to extricate myself from the ongoing press of day-to-day client responsibilities and develop a more location-independent business model.

Getting there wouldn’t be simple. It’s easy to step to the next branch if it’s right in front of you. But I had to take a leap of faith. My business to that point had been traditional marketing consulting for local companies with which I had some kind of personal connection, whether direct or through a referral.

I knew it would be very difficult to move beyond that—to jump into a new echelon of elite clients—by moving incrementally along the existing path. I needed to do something different to attract positive attention from people I didn’t already know, to reinvent myself and change my positioning in the marketplace.

To learn how to do that, I interviewed dozens of professionals who had successfully changed jobs or careers or how they were perceived by others. In 2013, that work led to my first published book, Reinventing You, which shares best practices in personal branding and professional reinvention, and answers the question: How can you make big changes, and position yourself for the career you want? The book is essentially a road map to help professionals make the transitions they seek.

But once you shift into your desired field, I realized, there’s another problem to solve: How can you work your way to the top and ensure that others recognize your expertise?

That was the question I sought to answer in Stand Out, my second book. I interviewed many of the world’s top experts, including business luminaries like Seth Godin, David Allen, Robert Cialdini, Tom Peters, and more, to understand how they developed breakthrough ideas and built a following around them. In that book, I laid out a blueprint for how regular professionals can follow those same principles to ensure their own talents get noticed.

As I soon learned, however, becoming a recognized expert these days doesn’t always lead to money. The elephant in the room of modern entrepreneurship is that even people who seem to be at the top of their game aren’t always monetizing successfully. Learning to make money from your expertise is a different skill set from what’s needed to become excellent at your work or well known in your field (two critically important things that I cover in depth in Reinventing You and Stand Out, but that aren’t, on their own, sufficient for big earnings).

That’s why I conceived of these three books as a trilogy, with Entrepreneurial You as the logical and essential conclusion. Entrepreneurial You seeks to address what I believe is the most important question of all: How can you create a long-term, sustainable business that rewards you emotionally, intellectually, and financially?

I want to see more talented people sharing their ideas in the world. But that won’t be possible until they’re able to create lasting, successful careers for themselves. With this book, I share ideas, strategies, and best practices for monetization that I hope make it more likely for everyone to succeed.

I try to practice what I preach. I learned an enormous amount from the entrepreneurs and side hustlers profiled in this book. The year I spent writing Entrepreneurial You has been my most lucrative to date, as a direct result of implementing the techniques I share in this book. I grew my income by more than $200,000 that year, and I continue to experiment with new strategies and channels. Successful entrepreneurship should be thought of as an ongoing pilot, not a finished state.

The changes I’ve made have allowed me to create the business I want today, where I live in New York City (but could live anywhere if I chose) and travel frequently to interesting destinations for work (I wrote the first draft of this prologue on a flight to Aspen, and the final draft on a flight back from Amsterdam).

My current business model—fueled by seven distinct income streams—didn’t just happen. It was a series of conscious and deliberate choices. I hope that by sharing what I’ve learned from the exceptionally successful entrepreneurs profiled in this book, and by recounting a bit of my own journey along the way, you’ll be able to make your own informed choices about what you’d like your business model—and your life—to look like, and shape it accordingly. Let’s get started.

PART ONE

Build Your Brand

CHAPTER 1

The Entrepreneurial Opportunity

I had made it. I was flying back from Asia in a business-class seat, stretched out and sipping a complimentary mimosa. I’d just earned $35,000 for two weeks of teaching at a university overseas. It was intensive—six hours in front of the classroom each day, all while fighting a bad cold. But the amount I earned in those two weeks nearly equaled my entire year’s salary before starting my own business, as a marketing-strategy consultant, in 2006.

In the intervening decade, I’d discovered that entrepreneurship suited me. Within a year of launching my business, I was feeling fulfilled and earning six figures advising interesting clients like Google, Yale University, and the US National Park Service. Since then, I’d been growing my business slowly and steadily—my own vision of the good life.

But shortly after I walked off that flight from Asia, I received an email that made me wonder how well I was really doing after all. It was from my friend John Corcoran, an attorney and blogger in the San Francisco Bay Area who’d immersed himself over the past several years in online marketing. A few times a week, he’d send out helpful articles and other content to his email list, which I always enjoyed receiving.

That month, however, he’d also been promoting two digital courses created by some well-known leaders in the online marketing world. Corcoran had signed up as an affiliate, and if his readers made a purchase, he’d get a commission. Affiliate marketing is a win-win, bringing in new customers and rewarding the person who does so at no cost to the customer. I had emailed him before my flight to find out how his promotion was going.

I ended up converting 32 buyers, he wrote me. That’s about $28K in revenue for five or six emails, one blog post, and one video throughout the month. If I add in other blog-and podcast-related income, I probably earned about $33–34K related to my blog alone last month.

My jaw dropped. He added: I didn’t work any more hours last month than I did in previous months.

I had always thought of online marketing as something vaguely scammy—the world of Nigerian princes and spam emails hawking discounted Viagra. MAKE MONEY ONLINE! their messages would scream—and I’d hit delete. I’d written it off completely.

But Corcoran made me realize I’d been missing something huge. Online marketing done right didn’t have to be exploitive or crass. And it could provide something powerful that I’d been lacking: a way to increase and diversify my revenue and minimize risk in my income stream. Yes, I was already working with multiple clients and doing various kinds of work—consulting, speaking, executive coaching, and business school teaching. But now I saw that I still wasn’t diversified enough.

Most entrepreneurs focus too much on earning revenue from one or two activities (such as consulting and speaking) and overlook other opportunities that can help free them from trading time for dollars. Diversifying can simultaneously enable you to earn more and mitigate risk.

What’s more, the opportunity isn’t just for entrepreneurs: even if you currently work for an organization full time and have no desire to become self-employed, developing entrepreneurial pursuits on the side can provide an additional income stream, as well as unexpected professional development opportunities.

Lenny Achan began his career as a nurse and worked his way up to becoming an administrator at Mount Sinai Hospital in New York City. But his career really took off when his supervisor discovered Achan had developed an app on the side. Achan was worried when he got called into his boss’s office: Had he violated a policy he hadn’t known about? Did they suspect he had been moonlighting on company time? As it turned out, his boss admired his initiative and promoted him to run social media—and eventually all communications—for the hospital.

Similarly, Bozi Dar—who was born in Serbia and now lives in the United States—has a traditionally successful career as a senior marketing executive for a Fortune 500 life sciences company.¹ But he became fascinated by the possibilities of entrepreneurship, and in 2013, he also tried to build an app, which ended up costing him $45,000 in development fees. It never earned a profit, but he learned invaluable lessons in the process about marketing, sales, and business strategy. The next year, he tried a different tack: an online course about how to get promoted at your company.

Dar’s course has been far more successful than his app, earning him $25,000 in its first year alone. But he’s actually seen some of the biggest returns in his day job, where he says his ability to bring a background in technology and digital is highly desirable. It enabled me to completely reinvent myself. He considers himself an intrapreneur, innovating inside his company, and he feels that continuing to operate in a large corporate environment, with its teams and budgetary resources, allows him to tackle high-profile ideas that would be incredibly hard to work on as an entrepreneur. (You can read more about Dar’s story and learn his tips for identifying your areas of expertise in the sidebar Assessing Your Areas of Expertise, at the end of chapter 2.)

Whether we work for ourselves or for others, we all need to find ways to diversify our revenue streams. That allows us to hedge against uncertainty, increase our impact, and earn more.

In my previous books, Reinventing You and Stand Out, I focused on how to develop your personal brand and ensure your expertise is recognized in the marketplace. Now in Entrepreneurial You, I’ll do what other recent books on career development don’t: I’ll show you how to make money in the uneasy economic environment in which we find ourselves today and create multiple, sustainable sources of income.

Many of the entrepreneurs profiled in this book work in the realm of marketing, leadership, and communications. That’s the world I know best, and one that I believe is at the leading edge when it comes to reinventing career paths and creating new strategies for monetization. But there are also plenty of case studies here featuring talented entrepreneurs in food, fashion, personal finance, and more. Regardless of your field, the foundational principles I share apply broadly; my goal is for you to see yourself and find new possibilities in the stories, whatever your current field or profession. Please note that unless otherwise specified, all quotes in the book come from personal interviews I conducted.

Additionally, many of the case studies, especially later in the book, focus on online marketing. That’s by design. Not everyone needs to become an online entrepreneur, and the early chapters of this book focus on decidedly analog activities like consulting, coaching, and professional speaking.

In much of Entrepreneurial You, however, you’ll find a heavy dose of information about internet-based techniques—from podcasting to blogging to online communities. That’s because these are newer paths to monetization and therefore often the ones that talented professionals haven’t yet explored or mastered. Even if you’re not planning on diving into the online world yet, these techniques are worth learning about so you have more options for the future.

Whether you’re a dedicated entrepreneur, a full- or part-time freelancer, or are hatching a sideline apart from your corporate job (and possibly planning your transition out of that job altogether), my hope and intention is for these pages to provide a blueprint for monetizing your expertise, both online and off.

It’s all about learning how to amp up the earning potential of a portfolio career.

Why We All Need Portfolio Careers

Common wisdom tells us that we should diversify our investment portfolios because it’s foolish to put all our money in one stock. But we’re far less careful on the other end. Too many of us rely on one employer for our entire sustenance, just as I once did.

Nearly fifteen years before that fateful flight back from Asia, I was fresh out of grad school and working as a political reporter at a weekly newspaper. Late one Monday afternoon, the human resources director called me into his office; I thought perhaps they were changing our dental plan. Instead, I got laid off, effective immediately—an early victim of the collapsing newspaper industry. HR gave me a box to pack up my desk and one week’s severance pay. I had no idea how I was going to support myself. I had to move fast.

The next morning—September 11, 2001—I woke up and flipped on the television. The day I needed to start looking for a job was the day America changed forever. Planes stopped flying, the stock market stopped trading, and absolutely no one wanted to hire an out-of-work reporter.

That’s when I started to understand the precarious nature of relying on one revenue stream; it could all be taken away instantly. For months, I tried to get another job in journalism, but no one was hiring. I scraped by freelancing; in a good week, I could pull down $800, but more often I brought in half that amount. Finally, I landed a full-time job as the spokesperson on a gubernatorial campaign; I earned what felt like a princely $3,000 per month, until we lost in the primary. I freelanced for another six months until getting hired as the spokesperson on a presidential campaign, which we also lost.

No job, I realized, is secure. Yet working without a guaranteed salary still seemed frightening to me; I saw a lot more risks than opportunities. By then I’d run out of choices, however, so I unwillingly became part of the vanguard of entrepreneurs developing a portfolio career—piecing together freelance work and ultimately starting my own business with various revenue