Nowadays just about everyone wants to be an entrepreneur—just ask the 72 percent of millennials who have considered starting their own business.

The entrepreneurial lifestyle seems to be the gold standard for freedom and flexibility, affording the luxury of doing what you want, where you want, with whomever you want.

Caribbean coconuts and cafe wifi, anyone?

While entrepreneurship can certainly appear sexy from the looks of Instagram, the truth is starting and building a business isn’t easy. It requires tenacity, commitment, and the ability to keep your cool when everything (no really… everything) falls apart.

There’s a good reason why 8 out of 10 entrepreneurs crash and burn within the first 18 months. So before you take the plunge, it’s wise to know if you’re actually cut out for the job.

One founder says starting a company is a job reserved only for the masochistic.

Meet Liz Wessel, a 25-year-old Ivy grad and the founder and CEO of WayUp, an online platform pairing employers with prospective students that raised over $10M in funding and was named one of the 30 Most Innovative Companies Changing the World by CNN. Wessel is also a TEDx speaker, Forbes Under 30 honoree, and the youngest-ever member of Clinton’s campaign committee.

This week on Unconventional Life, Wessel shares candidly about what it really takes to be an entrepreneur in 2017.


Born and raised in NYC, Wessel says she’s had a knack for entrepreneurship her entire life.

Her first major venture took off in college, when she launched PennEats as a sophomore at UPenn. The company partnered with local restaurants to offer students a 10% discount, and eventually became so successful that it franchised to other campuses across the US.

While in school, Wessel noticed an opening to solve an even bigger problem: the disconnect between job-seeking students and employee-seeking companies. “Why would businesses need to recruit through schools when students are very capable of talking to businesses directly without a middleman? I started seeing this trend where businesses wanted to work directly with students without needing to go through an institution,” Wessel says.

Thus, WayUp was born. In only two years since its launch, it has become one of the world’s leading platforms for job pairing, serving 1 Million+ students and boasting the highest job-pairing rate on the market with 1 in 3 applications resulting in a hire.

Wessel is a weathered entrepreneur who has navigated both the calm and chaos of business. She says it has demanded of her tremendous personal growth and stretched her in ways a traditional job cannot.

“You’re starting from nothing,” Wessel  says. “I don’t think everyone in the world would ever be interested in it. It’s really kind of masochistic. You have to be willing to go through a lot of pain.”

If you’re interested in starting a business, it’s important to be prepared for the full reality of entrepreneurship. The lifestyle you desire comes at a price—are you willing to pay it?

Below, Wessel shares 5 ways to know if you’ve got what it takes to be successful in entrepreneurship.

1. You’re willing to put yourself out there. You know what your strengths are and you aren’t afraid to own them. You’ve learned valuable lessons from your experiences that serve you well today and you know how to convey your wisdom. You’re not afraid to face rejection and are both persistent and resilient. You can take a lead from cold to hot at warp speed because of the way you carry yourself and believe in the value of your offering.

2. You’re willing to do whatever it takes. When it’s crunch time, you’re willing to put in long, arduous hours behind a computer screen or on the phone with clients to make magic happen. You’re willing to educate yourself and acquire the technical and personal skills you need to be the best you can be, at any cost. You’re willing to scrap together resources from unlikely places. You and your goal are inseparable and you see success as inevitable.

3. You’re willing to take risks. You aren’t afraid to invest time and money in an idea you believe in, even when it’s missing a fail-safe guarantee. You know that success takes faith and trust as well as action in alignment. Though entrepreneurship can feel like a roller coaster ride, you’re not afraid of heights or rickety turns. The exhilaration of weightlessness is what propels you to commit to the ride.

4. You’re sensible. You are grounded in your risk-taking by sensibility. You bounce your ideas off of other people and consult those who are more experienced than you. You are open to feedback and are equipped with research before you take action. You always look before you leap and try to engineer optimal conditions for success.

5. You’re not afraid to speak your truth. You are deeply connected to your inner truth and intuitive voice. You know that everyone in the world cannot possibly understand you, and isn’t meant to. You are not interested in holding back or diluting your message. You are willing to bring all of yourself to the table and know that it will resonate like a lock and key to the people you are meant to serve.

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Jules Schroeder
I am the Founder of CreateU, an online platform out to reimagine higher education in collaboration with the People+ Planet Project affiliated with the United Nations. At 26, I am creating a movement to empower Millennials to prosper and profit from doing what they are most passionate about through my podcast Unconventional Life, that profiles successful Millennials who earn their living in non traditional ways. I launched my first 6-figure company at the age of 18 and first 7-figure company at 22, while serving as a marketing consultant for many top companies. I am known for being a trailblazer and Millennial innovator with a unique ability to spot trends and create innovative global solutions. You can learn more about me at www.julesschroeder.com