Previous Lecture Complete and continue  

  Introducing You, The Bite-Sized Entrepreneur

I never intended to be an entrepreneur. I just had an idea.

At the time, I was a freelance tech journalist living in San Francisco. A friend of mine was struggling to remember a quote. I asked, innocently, “Isn’t there an app for that?” There wasn’t, and I found myself turning into an entrepreneur for the same reason most creators do: I realized something I needed did not exist and, if I didn’t create it, it might never exist.

The odd part wasn’t the journey to creating what would become the app So Quotable: it was who was actually making the journey. I wasn’t a young, hooded Harvard dropout like Facebook’s Zuckerberg, nor was I a brash, brilliant college dropout like Apple’s Jobs, nor a rich, hip L. A. kid like Snapchat’s Spiegel.

I was a journalist and author, an African American man in his mid-30s who, aside from negotiating rates with magazines, had no business experience.

In fact, at the time, I was about to propose to my now-wife. By the time So Quotable ramped up to launch three years later, I had bought my first home, married that long-time girlfriend, and we had our first kid. In the midst of the launch, a colleague helping out on the tech side bailed, and I found myself learning Apple’s iPhone programming language with one hand while rocking my newborn in my other, spare arm.

I wasn’t sure if the app – or even I – would make it to the finish line, but I also had not felt so alive in a long time. I’d wake up in the middle of the night with new ideas and realize elegant solutions to my app challenges during dinnertime. It was like I had two babies instead of just one. It was the passion to make my mark: I wasn’t staying up late and getting up ridiculously early to watch my favorite show or to have “me” time. It was a nobler cause.

I was also doing things my way. Instead of staying in Silicon Valley, ditching my girlfriend, and dressing like a college student, I moved out of Silicon Valley, settled down behind my proverbial white picket fence, and created the type of entrepreneurial life that I envisioned.

And, to my surprise, it worked. So Quotable launched in time for my first TED talk and gained a great cult following. The success connected me with two others to launched Cuddlr, a social plutonic app for connecting for hugs. Cuddlr hit #1 on the Apple App store twice, got us on the cover of The Wall Street Journal, and was acquired less than a year after it arrived. I handled the Cuddlr launch through daily 4 a.m. Skype calls with my international colleagues, with occasional breaks to coax my new toddler back to sleep.

The truth is that the success didn’t happen with the media coverage, the TED talk, or even the Cuddlr acquisition, but from doing and completing the work. As they say in Silicon Valley, real creators ship – and the product shipped! As soon as I met someone, told them about So Quotable, and said “You can download it off the Apple App Store now”, I won.

You absolutely have the ability to follow your passion, fulfill a public or personal need, and make a legacy for yourself within the structure of your 9-to-5, your family life, or your daily grind. Never before have we been more capable to pursue our passions within the time we have. Like kids jumping double dutch rope, we have more room for our dreams than we think – it’s just a matter of good strategy and timing. And perhaps that side hustle we create will become the foundation for the rest of our careers.

Bite-sized entrepreneurs incorporate brilliant startup techniques into their daily lives, giving themselves the focus and drive to pursue new passions while still being true to where they are in their personal and professional needs. The belief that you have to sacrifice your livelihood to leave your entrepreneurial mark is a lie. It isn’t about losing the life you have, but adding value to create the life you want.


There are many things a bite-sized entrepreneur is not. She is not a dilettante, dabbling in various pursuits to combat boredom or gain prestige; a bite-sized entrepreneur doesn’t give up when things get difficult. She is not a shallow businessperson, keeping the dedication superficial; a bite-sized entrepreneur dedicates every available ounce of free time to understanding her passion. She is not an obligated creator, getting her ego too invested into the idea to change; a bite-sized entrepreneur gives her passion space to transform organically into the business it was meant to be. Finally, she is not a patient person, assuming that one day she’ll have all the time in the world to pursue her true passion; a bite-sized entrepreneur ain’t waiting until retirement.

I’d love to be your guide on your entrepreneurial journey. Like my Inc. Magazine online column that inspired this book, I am giving you simple, digestible, and actionable insights that can be interwoven into your current life structure. You can flip through the 21 strategies in any order, though you may notice a natural flow if you read it straight from top to bottom. All of these ideas are explored with people who have successfully executed what you currently feel: A calling to create something bigger than yourself within the parameters of your current life. Everyone’s journey is different, which is the point: Realizing your business aspirations is not, and should not, be a one-size-fits-all process.

Let’s make an impact on our own terms. Today.

-Damon Brown, August 2016