Portrait of a Generation Z Entrepreneur

How the recession gave birth to the most entrepreneurial generation we’ve seen yet

Jonathan Denney
SV Entrepreneurs’ Corner
6 min readAug 14, 2014

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When the recession hit in 2008 I was still in middle school. I saw a lot of people lose their jobs, but like most teenagers, I didn’t really understand what was going on. It wasn’t until high school when I started working to earn money that I began understanding our economy and what had just happened…

Job security went out the window. My friends and I were now on an academic track that would lead to loads of student debt, with no promise of a decent paying job. My older siblings’ friends were graduating college and heading straight for Starbucks for work.

I remember asking myself “Is this really how I’m going to become successful?” one day in a math class in high school, frustrated because I knew the homework my teacher was giving me was taking away from me learning to code websites, and sell my digital services.

I knew there had to be a better path.

You see, I’m right at the beginning of Gen Z. We’re born no earlier than 1995, native to the Internet and with career paths greatly affected by the economic crash of 2008. “Go to school, get good grades and get a good job” was no longer always viable career advice. We’ve learned to take 20th century ideals with a grain of salt.

It’s a new millennium. A new age, the information age. The economy started to shift in 2008. What was being taught in school started to become obsolete, resulting in a massive unemployment rate. My generation was bound to be drastically different.

Generation Z is the entrepreneurial generation.

In 2010 “The Social Network” came out, presenting the idea of online entrepreneurship to millions of young people. Social networks and tech companies were the only success stories we had heard of recently, so we naturally started looking up to the wave of tech entrepreneurs that emerged.

Young, hip, disruptive, techie and dropout entrepreneurs became our idols.

Then Steve Jobs passed away in 2011, at the peak of his success. The dropout entrepreneur became socially acceptable by our society. The idea that you don’t have to go to school to become successful was now mainstream. And with unlimited access to the Internet at all times, more and more of us began finding relevant, up-to-date education online.

It’s 2014 now and we’re in a boom in the tech industry. Startups are everywhere. Older crowds say it’s the Dot-Com bubble all over again, with companies being scooped up for 9+ figures left and right.

A huge percentage of young people are choosing entrepreneurship over more traditional career paths. The word “Entrepreneur” doesn’t have that bad connotation it used to have.

In the next decade, there are going to be a lot of success stories.

While not technically a breakout success story yet, here’s the beginning of my story as a Gen Z entrepreneur…

I got started probably much earlier than most in my generation. In 2010, my sophomore year of high school, I was motivated to buy my first car. At 15 years old I couldn’t easily get a job just yet, so I started looking for alternative ways to make money. With nothing but a video camera and a computer, I started providing video services online and offline.

I was able to save up enough money for a 2004 Mustang in 3 months. The hustle had begun.

Filming skateboarding with friends as a kid led to developing video skills. Those video skills led to providing services as a freelancer in high school. And eventually, because businesses paid more for web design, I started to learn how to develop and design websites.

In time, that led to running a WordPress hosting business, and then starting a digital marketing agency.

At 19 years old, I’ve decided that I’m not going to college. It’s simply not worth it. I’m well aware of the many benefits of going, such as awesome networking and the social experience. But the tuition is ridiculous, the opportunity costs of going are huge, and unfortunately the ROI doesn’t look all too good.

A degree helps you become an employee. I don’t want to be an employee. Growing up in the recession, I know that being an employee provides false financial security. Why have one source of income to depend on, when you can have multiple sources from your own business, and be building wealth at the same time?

I’d rather continue my education as an entrepreneur. I’d like to think learning how to function in the real world, having started and ran 2 businesses, has put me ahead of my class in school in some aspects of life. As if reality is sort of postponed until they’re dropped right into the world of post-grad life.

Although I would never encourage anyone to drop out of school…

Here are reasons why I encourage my fellow Gen Z’rs to start a business…

1 — You learn how to sell

If you don’t know how to sell, you will end up working for someone who does. That’s capitalism.

Once you learn how to sell one thing, you’ve learned how to sell another. The process is the same. Only the offer changes. The offers you sell may be products, services, startup ideas, or even your skills as a team member. In this world where you’re always selling something to someone, you might as well be good at it, because most people aren’t. Being good at selling gives you a massive unfair advantage.

2 — You learn how to deal with people

Books can’t teach you people skills. Dealing with people teaches you people skills. Running your own business is largely about relationships and social dynamics, and that’ll benefit you dramatically throughout your life in many areas.

3 — You learn how to solve problems

Life is a series of challenges, obstacles and problems to face. There’s many ways to overcome these challenges, and running a business makes you very good at it. You learn to accept your current situation, decide what to do based on the resources and knowledge you have, and ruthlessly execute.

4 — You learn how to have grit

Starting a real business that actually generates revenue and provides value is really f*cking hard for most people. It takes an uncommon work ethic and mindset to make it possible. That’s why most people are employees. They don’t have the grit to persist on their own and succeed.

So many valuable lessons are learned in the process of failing over and over again while building and running a business. You’ll really develop your ability to persist through the shit periods that you’re bound to experience, and it’s all worth it.

5 — You learn how to hustle

While working for someone else, you get a steady pay check. This makes you lazy. It’s really easy to get up, go to work, do what you’re told to do and get paid a fixed amount. But there’s no growth in that!

As a Gen Z’r, you’ve barely started your 20’s. You don’t need a BMW or the latest iPhone. Sacrifice money now for personal growth. It’ll pay off later far more than you can imagine.

And when you run a business, you have business expenses, personal bills and the responsibility of other people’s income. And there’s no fixed check guaranteed to come every two weeks. Every day you wake up and have to figure it out. You learn how to find opportunities everywhere to stay afloat. This instills patterns in your work ethic and mindset that we call “hustle”.

6 — You learn how to become a better decision maker

You have to actually think about what is the right thing to do, with the risk of potentially making a wrong decision. As an entrepreneur, you’re truly accountable. There’s no margin for error. And when you do make the wrong call, you learn how to deal with the consequences to avoid doing it again. Those experiences are invaluable.

Since a bigger percentage of the Gen Z population is skipping college, in the coming years you will see many successful businesses emerge from the influx of young, scrappy entrepreneurs.

And most importantly, the entrepreneurs behind those businesses will continue to pump out awesome innovation and strengthen our economy for decades to come.

And more of the next Steves and Zucks will had been driven by education from their experience functioning in the real world, and from the Internet, rather than just school.

This is why Generation Z will be the most entrepreneurial generation we’ve seen yet.

Want more? Follow me on Twitter and on Medium.

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