Adventures in Disruption: How to Start, Survive, and Succeed as a Creative Entrepreneur

Adventures in Disruption

How to Start, Survive, and Succeed as a Creative Entrepreneur

Sam Aquillano

Copyright © 2023 Sam Aquillano

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Print ISBN: 979-8-9896363-0-3

eBook ISBN: 979-8-9896363-1-0

Audiobook ISBN: 979-8-9896363-2-7

To Nicole, who taught me how to follow my heart.

Contents

Title Page

Copyright

Dedication

FOREWORD

INTRODUCTION

CHAPTER 1

CHAPTER 2

CHAPTER 3

CHAPTER 4

CHAPTER 5

CHAPTER 6

CHAPTER 7

CHAPTER 8

CHAPTER 9

CHAPTER 10

CHAPTER 11

CHAPTER 12

CHAPTER 13

CONCLUSION

ACKNOWLEDGEMENTS

FOREWORD

By Michael DiTullo

There are a lot of books about startups and entrepreneurship, why should you read this one? Read this book because Sam Aquillano has the courage to tell you the candid, unvarnished truth about how hard it is to start something and why you shouldn’t let that stop you. It would have been so easy for Sam to have never left his corporate design job at Bose. Working at a company like that is a coveted position for any industrial designer. He could have stayed and lived a happy life, but that just wasn’t an option. I know it wasn’t because I was in that same position. I was a designer at one of the most well-known companies in the world, Nike, and I was very happy there. There was just this little itch at the back of my mind that would never seem to go away. At a certain point, I knew I would have to leave to start my own company even though in many ways I didn’t want to. I just had to.

​Do you have that feeling? Of course you do. You wouldn’t be reading this if you didn’t. One of the biggest secrets that Sam lets you in on in this book is that there are many people out there with the same feeling you have. The sense that they could build something no one else has ever built before, that they could fly on their own. Find a few other people like yourself and start something. Not because it will be easy, it won’t be, but because you just have to fly.

​American philosopher, artist, and publisher Elbert Hubbard once said, A little more persistence, a little more effort, and what seemed hopeless failure may turn to glorious success. This book is all about persistence, not of one person, but of a group of people, all bonded to a common cause. If you start something, you will need that group of people that are more than friends, they are more than partners; they are fellow adventurers who will never let you give up. There will be times when the going will get tough, you will have doubts, and there will be challenges that will force you to change course and make a new plan. Having those like-minded individuals around you will ensure there is always someone there ready to keep pushing. What you are about to read is a first-hand account of Sam and his team’s journey that will include the trials they faced, the lessons they learned, and tips for you to use in your own journey.

​You might have noticed the word creative right in front of entrepreneur on the cover. You might not be a designer, a copywriter, or an engineer; but if you are an entrepreneur, you are creative. By definition, your goal is to create something that never existed, so you will need to be in that creative head space. Sam is about to tell you how he and his team used low-stakes creative approaches at every turn to take safe risks, try things out—even if just for themselves—and how they turned the people they were pitching to into believers. When your vision becomes their vision, you win.

INTRODUCTION

To read is to voyage through time.

— Carl Sagan, author, astronomer 

How does someone start a museum? 

​I was sitting across from one of my students, Billy Vespa, in a hotel ballroom at a design conference in the fall of 2009, and I had just told him my big idea. He was one of the first people with whom I shared my business idea, even though it had been rattling around in my brain for over two years. But he asked the right question at the right moment. My friend and long-time collaborator, Derek Cascio, and I were just ending our tenure as volunteer leaders of the Boston chapter of a national design organization, and Billy knew Derek and I were not likely to sit idle for long.

​He asked me what we were going to do next: I know you and Derek always have something cooking. Indeed we did, I told him: Our plan is to start a design museum here in Boston. 

​How does someone start a museum? he asked. I replied, I have no idea. 

​But over thirteen years, and with a lot of help, we launched and built Design Museum Everywhere, a new kind of museum to bring the transformative power of design everywhere—and I mean everywhere. Over the course of our entrepreneurial adventure, we redefined what it means to be a museum in the 21st century. We’re online, nomadic, and accessible to all. Instead of a single museum location, we pop up exhibitions and special events in places like galleries, retail environments, public spaces, lobbies, schools, and more in cities across the country. And we’re everywhere you find content: virtual events, online articles, podcasts, videos, and even a quarterly print magazine on design impact. We disrupted the entire notion of what a museum is. In place of a building, we built a global community of design thinkers and changemakers. It was the ultimate adventure in creative entrepreneurship.

​Creative entrepreneurship is the pursuit of launching and growing not just new businesses but new kinds of businesses—sometimes the business model hasn’t even been invented yet! Creative ventures require creative thinking, problem solving, and the ability to identify and capitalize on opportunities.

​I was once pitched by a marketing consulting firm that thought they could help take Design Museum Everywhere to the next level. The big case study they showed as proof was their work for a company that sold yachts. It was an impressive presentation if you had a simple business model, like selling yachts. I had to explain to them the complex quilt of business models we employ at the museum. A mix of membership, advertising, subscriptions, ticket sales, sponsorship, grants, and donations—each revenue stream with its own unique variations needed to be woven together into the beautiful patchwork that is our business model. But that’s what it takes for creative ventures to survive and succeed.

​Think about Airbnb. A model for creating a business where individuals rent out their homes or apartments to travelers just didn’t exist until co-founders Brian Chesky and Joe Gebbia—two industrial designers—made it happen. They were living in San Francisco in 2008, struggling to pay their rent, when the Industrial Designers Society of America international conference came to town, and they realized designers attending the conference (including me) needed a cheap place to stay. So they set up a website called AirBed & Breakfast, and the first listings were the three air mattresses set up in their living room. From there they went on to disrupt the entire hotel industry.

​Then there’s ArtLifting, started by my friend Liz Powers and her brother Spencer. ArtLifting is a social enterprise that empowers artists who are houseless or have disabilities by selling their artwork and providing them with a source of income. Liz studied art therapy, and while volunteering at shelters, she noticed many of the residents were talented artists, but they lacked the means to sell their work. ArtLifting was created as a platform for these artists to sell their artwork and earn a fair wage. Now that’s life-changing, disruptive innovation!

​Creative entrepreneurs like Brian, Joe, Liz, and Spencer are driven by their passion for impact, change, and bringing new ideas to life. You are a creative entrepreneur as well. Even if you won’t admit it to yourself (yet), I know it’s true. I know you have a business idea—or two or three—in that head of yours. I know because you’re human, and our natural inclination is to create, to make, and to build. But starting something is hard, risky, and clouded in uncertainty. Entrepreneurship can be so overwhelming with endless possibilities that most ideas stay locked in people’s minds alongside self-doubt and worry—denying the rest of us their impactful creations. 

​Now imagine a world where you have launched your dream business idea. Imagine you broke through self-doubt, recruited people to your cause, proved the naysayers wrong, and built something incredible that brings people joy and utility and makes real change in the world—something you can be proud of. That’s a pretty great world. I like living in that world, the land of possibilities. When you’re in that time and space of utilizing your passion, collaborating with partners, and offering something to people they truly value, it’s magical.

​I hope my entrepreneurial story can serve as a guide. I’ll share the real story, not a glossy, spruced-up startup mythology. You’ll hear how I deliberately got my idea out of my head and shared it with others, even if it took over two years; how my co-founder, Derek, and I built a community from day one; how we pivoted constantly and maintained a culture of adaptability to find and create opportunities every step of the way. I’ll add some insights and advice along the way so you can apply what you learn and accelerate past the mistakes I made.

​I wrote this tale of our journey because over the course of the thirteen years I ran the Design Museum as its founding executive director, I got a lot of questions just like Billy Vespa’s: How did you start the Design Museum? I’ve sat across from so many aspiring entrepreneurs over the years—in coffee shops, Zoom meetings, and classrooms at Babson College, Wentworth Institute of Technology, and Massachusetts College of Art and Design where I taught design and entrepreneurship—and shared this story.

​Folks who know me know I live and breathe design—I consider it my calling, and I’ll share how I found it and combined it with my entrepreneurial nature and business acumen to create new initiatives. But let me be clear—I didn’t start the Design Museum alone. Without the dedication of countless individuals, this story wouldn’t be possible. This isn’t a quick path to success with a ten-step plan for launching your new idea. And I’m not here to pretend any of this was easy—that’s not real. 

​I do believe that every new business has three foundational assets: your team, your community, and your brand. Your team believes in the business, supports you, and makes more things possible than you could ever hope to do alone. With a team, one plus one equals three (or more). You’ll read about my co-founder and our team in chapter two. A community believes in you, feels deeply connected to your vision, and will evangelize the business to the world—every business needs a community to help lift it out of obscurity, and I’ll show you how we built ours in chapter three. Your brand is how you present your venture to the world. It’s visual, yes, but it’s more than a logo. It’s how the essence of your work permeates everything you do, and it’s what sticks in the mind of your customers, bringing them back for more. Brand is so important you’ll read about it in chapters one and three, and in chapter eight I share the unique way we developed our brand identity.

​Of course, every business also needs to make money. In chapter ten, I go into detail on how we monetized our unique approach into a sustainable business model. Finally, in chapters twelve and thirteen, you’ll see how we achieved product-market fit and grew our business and value to our community.

​I promise an interesting, insightful, real story about the entrepreneurial adventure that resulted in a creative, disruptive organization. I hope it inspires you to make your business idea come to life. Let’s start at the beginning—the real beginning—when the idea for Design Museum Everywhere was just a dream stuck in my head. Here’s how I got it out.

CHAPTER 1

Survive the Commencement Paradox

You are the first customer for your own idea.

The hardest thing about getting started, is getting started

— Guy Kawasaki, author, entrepreneur, and evangelist

When is the beginning? You might think it’s at the start, but no. When we’re talking about launching an idea, business, organization, venture, you name it, the beginning and the start are much more complicated. Take this book for example. The process of writing this book began in June 2014 when I was invited to speak at TEDxFenway about the museum I founded, Design Museum Boston (now called Design Museum Everywhere, but more on that later). At the time, TEDx events were popping up around the world as independently organized versions of the main, very exclusive, annual TED conference. As the founder of a growing startup, I was honored to speak, and I knew that any opportunity to talk about my business in front of an audience of any size was something to lean into. The event organizers invited me to talk about the Design Museum, but I had something else on my mind: helping others get to the same place I was, having started something I was super passionate about and working like hell to make it survive and succeed.

​I was introduced to the TEDxFenway stage by Anita Walker, Executive Director of the Massachusetts Cultural Council. She said something like, Please welcome Sam Aquillano to talk to us about a new kind of museum he has started. I got on stage in front of a few hundred people and proceeded to let them know, Actually, I won’t be talking about Design Museum Boston, at least not directly. Out of the corner of my eye, I saw the organizers’ faces turn white (sorry, organizers). I proceeded to remind everyone about the theme of the event, grit, and that the grittiest thing I could think of was entrepreneurship. I proceeded to give my talk, titled, The Laws of Zero-Stage Entrepreneurship. In that short, eleven-minute presentation, I gave ten bits of advice for starting a business, particularly a business that no one thought could ever exist. Those ten points pretty closely match the chapters of this book.

​I finished my talk, and as I walked offstage, I knew in my gut that I should write a book about my experience starting Design Museum Everywhere and provide advice for new entrepreneurs. But it took me seven years to start writing it—why? It would be easy to say a lot happened and got in the way of launching this publishing venture. In the seven years since I gave that talk, I got married, had three kids, bought a house, and grew a startup nonprofit museum to a level of sustainability and impact of which I never could have dreamed—these are important reasons, but they’re beside the point. The truth is it took me seven years to convince myself that I should do this, that I had something to say and contribute to this space, and that my experiences could be helpful to others. I was filled with fear and self-doubt, and I didn’t follow the advice I’m writing in this book for you (I wish I had!).

​Business, particularly starting a business, is one of the most complex things there is. But when you boil it down, you realize a lot of business is about convincing people to do something—convincing people to join you (hiring), convincing people you have the right strategy (leadership), and convincing people to buy what you’re selling (marketing and sales). But as so often happens in the stories of entrepreneurship we tell each other, we gloss over the internal struggle. Starting something is deeply personal, and the first person you need to convince is yourself. You are your own first customer of this new idea. Are you going to buy in?

​I didn’t buy into my own idea immediately. For me, there was a sizable gap between the beginning and the start. 

———

To understand the beginning of the Design Museum, you need to understand more about me. I was a creative kid from two creative parents—surrounded by a big Italian-American family that prioritizes family and community. My dad began his career as a draftsman before succeeding in corporate finance. My mom is incredibly creative and can do wondrous things with arts and crafts. My parents supported my earliest creative endeavors and showed me the value of hard work. My mom taught me how to draw and helped me and my siblings enter the annual Parent Teacher Association youth art contest every year. I won the state trophy in fifth grade—a very proud moment for a ten-year-old artist finding his creative place in the world.

​I’ve always been entrepreneurial. In elementary school, I sold baseball cards to the other kids on the bus. When I was thirteen, I got a spiral-bound notebook and wrote Book of Ideas on the cover. On the first page, I wrote, I’m going to change the world. I filled that notebook with ideas for products, businesses, video games, and more. In high school, I got one of the first consumer CD burners—I handed out little slips of paper at school with ten lines on them. My classmates could list any ten songs, and I’d make them a mix CD for $10. (Not the most legal business. I understand that now.) And all through my teenage years, my brother Steve and I ran a lawn and landscaping business called Earthworks Lawn Care. 

​I was a creative entrepreneur before I knew what that meant. As a junior in high school, I had no idea design was a potential career, I didn’t even know design was a thing. I knew I liked to draw and come up with ideas and make them happen. Not knowing about design, I toured colleges and universities around New England, New York, and Pennsylvania, looking at mechanical engineering departments. My parents and I thought engineering was my best bet at a career doing something I enjoyed and was good at. No offense to the mechanical engineers of the world, but it wasn’t my cup of tea. As I heard presentations from faculty and got tours from engineering students, there just wasn’t enough art or creativity—I needed something different. It was the last school I visited with my parents, Rochester Institute of Technology (RIT), where I made the discovery that would change my life. We toured the engineering department, of course, and I felt that same feeling of dread—was this all the world and the economy had for me? 

​But it was in the financial aid office, as my parents were discussing options with a staffer, that I found it. Sitting in the waiting area, there was a big display of pamphlets to my right—a pamphlet for each major at the college. And there it was, a pamphlet with some products on the front and a sketch of an ice boat. I didn’t even know what an ice boat was. I grabbed it, opened it, and proceeded to read about the field of industrial design, where designers work to envision the form and function of the products we all see and use every day. I had struck gold. This was it. I only applied to RIT, mistakenly thinking that RIT was the only school on the entire East Coast that offered industrial design.

​I struck gold twice because it was also at RIT where I first met Derek Cascio—a lifelong friend and the person with whom I would start the Design Museum. Derek is truly one of a kind. He’s not a large person (quite the opposite, he’s a skinny Italian guy). He’s bald, although he did have hair when we first met, with a beard. He has more energy in his pinky finger than a normal person expends in a typical year. He’s fueled by coffee—I rarely see him without a paper cup in his hand, and he’s one of the best designers I know. He can design and draw anything and tell you the story behind things that only exist in his imagination. Watching Derek’s Instagram live sessions, where he narrates as he draws products, robots, and monsters is now one of my favorite pastimes. My kids love it, too.

​Derek simultaneously believes people should be responsible and take care of their own business and that he can help every human with whatever they need. If Derek had a tagline, it would be, I’m here to help. As a kid, he was always drawing characters and developing stories, so when it came time for college, he enrolled in the top-tier animation program at RIT. With him in animation and me in industrial design, our paths didn’t cross in the classroom. My roommate in the cramped RIT dorms, however, was in animation, and Derek would swing by to chat with Anthony about classes and assignments from time to time. Derek told me later that he was always looking over my shoulder as I was sketching a product or making a little foam model—he was intrigued by design. That year, Derek sort of realized animation wasn’t enough for him. He wanted more, so he transferred out of RIT and moved to Boston to look for other academic opportunities and be closer to home. I didn’t think I’d ever see him again.

———

​At RIT I launched my first entrepreneurial effort in design. During my junior year, I and a handful of fellow design students—Don Lehman, Laura Ori Fowler, and Chuck Cerankosky—were on the road from Rochester, NY, to Bridgeport, CT, in Don’s old, blue minivan. And we were excited. The Industrial Design Society of America’s annual national conference was completely out of reach for students and young designers, owing to the ticket cost and travel required. But the regional conferences took place at design schools in each region and were billed as an