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Geniecast Blog

For Aspiring Entrepreneurs: Here’s Why You Should Take the Plunge

Posted by Geniecast on Aug 2, 2016 10:40:46 AM

Jump in — the water’s fine. 

These are the words of author, successful entrepreneur and Geniecast Genie Damon Brown. Damon-Brown_1.jpg

Today Damon celebrates the launch of his new book, “The Bite-Sized Entrepreneur.” In the book, Damon shares a refreshing perspective on entrepreneurship — he challenges the belief that entrepreneurs have to sacrifice family, friends and fun to achieve success. And, he’s not theorizing either. Damon wrote the book based on his experience developing and launching the Cuddlr app.

We checked in with Damon to learn more about “The Bite-Sized Entrepreneur” and his approach to entrepreneurship.   


“The Bite-Sized Entrepreneur” is written to help aspiring entrepreneurs turn their passion into a smart side hustle. Define the phrase "smart side hustle" in your words.  

A “smart side hustle” is something you are passionate about that grows organically. A side hustle should not be something you immediately lean on for income — the pressure to make a profit can crush its potential growth and you may find yourself making compromises before you even start. The smart part is trusting the process and understanding that passion is the hard part; if you are truly connecting to your love, then other people will recognize your genius and pay to be part of your experience.

Why do so many entrepreneurs have trouble balancing their work and home lives?  

Entrepreneurship demands so much from you that it can easily take over your life. That’s why people believe entrepreneurship cannot be done within the context of their current life.

In my case, spending years working with multiple freelance clients and, later, juggling being the primary caretaker of my first son and my career, helped me get grounded in my priorities. Hopefully, some of that influenced the book and can give insight to others. 

What inspired you to tell your story? 

It was the previous years spent in Silicon Valley. I was there when the iPhone first came out, as well as the iPad, and I lived down the street from colleagues and friends who became six or even seven figures richer seemingly overnight. The most interesting part was how the amount of sacrifices you made at that moment became a point of pride. Staying up for three days straight to work on your startup was something that you would be given credit for. I dedicate a whole chapter to this in The Bite-Sized Entrepreneur.

I was strictly an observer — as a journalist for outlets and as a friend to many entrepreneurs — but I didn’t really take the plunge until I left Silicon Valley. I programmed and released a small quote app, So Quotable, and that led to me connecting with two other folks to release the social meetup app, Cuddlr. Our app went to number one in the Apple store and got us a ridiculous amount of press as well as lots of users. We sold it in 2015, less than a year after we started.

Mind you, both So Quotable and Cuddlr happened as I became a first-time father and my son’s primary caretaker (my wife had a traditional 9-to-5). Every day I said to myself, “I’m there for my son, yet I’m helping lead the number one app in several countries. This isn’t supposed to be happening!”


I realized that, as I say in the book, “The belief that you have to sacrifice your livelihood to leave your entrepreneurial mark is a lie.” There are many reasons why we want to believe it, from feeding our ego to putting off taking a risk. It took me leaving Silicon Valley to understand that.

What was the most surprising thing that happened during the development and launch of the Cuddlr app? 

The amount of people who said the app was what was missing in their lives. I spent much of my cofoundership handling our user communication — of which there was a lot! — and we saw firsthand how many people were craving a way to connect with others that wasn’t just for dating or hookups.

Before this book, my two most notable titles were "Our Virtual Shadow: Why We Are Obsessed with Documenting Our Lives Online" and "Porn & Pong: How Grand Theft Auto, Tomb Raider & Other Sexy Games Changed Our Culture." I’ve done two TED talks about technology bringing us closer. I care about how tech is evolving our intimacy and our connection to the world. It was breathtaking to be on the forefront of a service giving hundreds of thousands of people new ways to connect. It is still humbling now.

What was one memorable challenge you faced, and how did you address it? 

It would be a tie between an aggressive media cycle and our loyal customers. I’ve spent years as a journalist, so I thought I understood media, but there is nothing like being on the frontlines of a controversial product or service.

As the name implies, Cuddlr was meant to connect people for platonic hugs. The media was more than skeptical! Our best move was actually before the app came out: We published an essay describing our intention and also gave an exclusive interview to a journalist we trusted would understand our intention. The media had a proverbial field day with our quirky concept, which actually helped our popularity, I’m sure. It was tough being in the hot seat, though, as we were one of the most talked-about apps from September 2014 to well through the holidays.

Satisfying our customers was equally difficult; although, for me, it was because our service should rightfully reach a higher standard. I mean, we are connecting people for a physical interaction — from college students to retirement-age folks. If the app crashes, then that connection may never happen.

Again, I was on the front lines for many of our user challenges, so I saw and supported them firsthand. But I also held us to a higher standard than, say, a food delivery app or a car service app. According to some users, we were directly impacting people’s lives. Moving on from the app was both sad and relieving.

If you could give just one piece of advice to a young entrepreneur (besides reading your book!), what would you say? 

Pursue it now. It will not get easier later. You may get more money later, but you also will have less energy as you get older. You may get more wisdom later, but you also may miss an opportunity.

Cuddlr was an immediate, whirlwind hit, but I helped develop it with my knowledge of technology and intimacy from my books. Those books came from my time as a journalist, and that journalistic interest came from me pursuing the topic I found most fascinating. Imagine if I didn’t start following my passion when I was young?

Do you have a daily mantra? If so, what is it? 

I don’t have a mantra, but this is top of mind for me: I have no intention of looking back a year from now and seeing myself in the same place. A year before So Quotable came out, I didn’t know how to program an Apple device. A year before we sold Cuddlr, I didn’t know anything about being a co-founder. A year ago this week, we had sold Cuddlr and I just started my column for Inc.com, Sane Success. That column heavily inspired this book. Who knew? I didn’t, and I think that’s the point. It is about doing the work. Luck and opportunity will reward your efforts.

You've written 17 books. Which is your favorite? In 20 years, which do you think will have had the largest impact? 

As I said in a recent Inc. column, that’s akin to choosing your favorite kid! I’m currently in love with "The Bite-Sized Entrepreneur," simply because it came together organically. It sprung from my regular column, so the ideas in it have been developed over the course of hundreds of articles and discussions. For lack of a better term, I don’t think I’ve ever had a book workshopped so publically. The ideas in it are time tested and entrepreneurially approved.

Porn & Pong would probably be my long-time favorite. It was my first major book and my first book tour. It also took five years to write, which, considering I was pretty young, was a good chunk of time. It also taught me to listen to my gut: When I started the book, the average person I mentioned it to would say “intimacy and video games have absolutely no connection.” But by the time it was released, the average person would say “this didn’t exist already?”

The book is now, along with Brenda Brathwaite’s "Sex In Video Games," considered the definitive resource for understanding how interactive gaming helped create our tech-driven intimacy today. It is now in university curriculums across the country.

As with Cuddlr, I was fortunate enough to see where the culture was shifting. I believe we all have that gift about something. Our only job is to trust what our vision is saying.

Were you always a writer (that is, the guy people wanted to sit next to in English class)? 

My folks joke that I was born with a pencil in one hand and a joystick in the other. I have always been a storyteller. I have always loved technology and its impact on culture. The stories I tell today, whether as a writer or as an entrepreneur, are a reflection of those two loves.

If someone were to make a movie about your life, who would you want to play you? 

I’d love to see who the director would pick! If anything, I’d like to see it similar to the Bob Dylan bio pic “I’m Not Here” — five or so different actors depicting the many people I have been. I still have the same core, but my expression of that core is consciously and constantly evolving.

Who's your biggest inspiration in business? 

I get inspired by many people, and not necessarily people the public would know. It’s one of the reasons I love being on book tour, doing public speaking through Geniecast, and using social media to communicate. I believe every single person has a gem of knowledge to share. It is just a matter of listening. 

Any chance you'd give us a hint at your next project? 

It is The Bite-Sized Entrepreneur Series, so there are other ideas in the works. Also, if you have read the book, you know I have many projects percolating on index cards. I’m as excited to find out what the next thing will be as others are, but there are always things in the works. 

"The Bite-Sized Entrepreneur" has my full attention right now. I’m excited that it can potentially inspire the next entrepreneur to take the plunge. I want to tell them, “The water’s fine.”

Engage with Damon Brown via Geniecast. He has three programs available: "The Bite-Sized Entrepreneur" Interactive Discussion, Book Discussion: The TED Book "Our Virtual Shadow" and How Technology Ignites our Intimacy


Topics: entrepreneurship