The Entrepreneurial Roller-coaster and the Sacrifices

by / ⠀Personal Branding Startup Advice / September 27, 2012

“How did you do it?” is a question I often hear after telling people that I run my own media company at the age of 27.  An expectant grin awaits some sort of magical, oversimplified answer that just doesn’t exist.

I typically respond simply- “hard work”, “took a chance”, “found a great opportunity”- knowing that most people don’t really want to hear a long story that started 3 years ago with a leap of faith. People like to maintain the image of entrepreneurs after the big pay day, rather than thinking about those scraping by to get there; an epic blockbuster conclusion rather than a self-discovery indie story. Especially in today’s world of digital entrepreneurs, the illusion of overnight success and a sexy jet-setting entrepreneurial lifestyle is more rampant than ever.

In truth, a large part of “how I did it” boils down to several years of making sacrifices that would make most people extremely uncomfortable. For those of us without large resources to pull from, a sustainable idea; the tactical execution of that idea; and good old persistence only goes as far as the time you can buy yourself by scraping by. Sure, building computers out of a garage or illegally squatting at AOL headquarters can sound pretty exciting, but how many people would really be willing to give up a cushy lifestyle for the chance to build their own company?

Three years after starting my own entrepreneurial journey, I now run a hyperlocal digital licensing network with locations up and down the east coast; I love that part of growing our business is helping other ambitious people launch and grow their own businesses.  One of the topics that we tackle before launching is how much they’re willing to sacrifice to establish and grow their business.

For me, quitting a very comfortable job at a hedge fund in New York City was just the beginning. I’ve invested years of my personal savings, lived in basements for more time than I’d like to admit, and worked several part time jobs to keep afloat while pursuing my business.  When looking for apartments, I wasn’t so much concerned with hardwood floors or basic amenities. Instead, I was busy precisely calculating the number of months I could afford to keep the place with my savings alone if I were to re-invest all of the profits from my business back into the company. Only after reaching year 3 of profitability with my business did I allow myself to “splurge” on a no-frill 1 bedroom apartment, which I split with my boyfriend.

A recent article in The Atlantic called Millennials “The Cheapest Generation” for their reluctance to make large purchases, such as cars and homes. While some of my cohorts voiced outrage over the title, I actually felt a hint of pride. Do I think I am cheap? No, I do not, but I do think I am resourceful and even a bit scrappy when necessary.  I believe that scrappiness is what allowed me to build a network of 15 magazines in 3 years time. Rather than slow down growth by taking a larger paycheck, I’d prefer to re-invest to speed up growth.

When I quit my finance job, I vividly remember a co-worker enviously saying to me, “You’re so lucky! I wish I could do that.” I nodded politely but at the time, all I could think was, “Lucky? This guy has no family or mortgage holding him back. What does he mean he wishes he could do this?” Looking back now, I realize that to him, giving up a certain lifestyle simply wasn’t an option. He knew his threshold and accepted it.

I know that the ambitious goals I’ve set for my company will require more personal sacrifices in the future. Will it be easy? No. Will there be brief moments of weakness when it doesn’t seem worth it? Yes. But after three years aboard the entrepreneurial rollercoaster, I also know that when I achieve one of my goals, all of those sacrifices will make the success that much sweeter.

Tina Paparone  and Angela Giovine are the founders of Happenings Media, a network of hyperlocal digital lifestyle magazines.  Run by local publishers, each digital magazine serves as a lifestyle and entertainment resource their community while providing innovative digital marketing services to local, regional, and national advertisers.

About The Author


Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.

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