3 Ways to Immerse Yourself in Startup Life

When I speak to recent grads of high school, undergrad or masters programs, I'm often asked the exact same question: "Should I pursue my own business now or work for a startup?" 

I think the prevailing assumption is that entrepreneurs are autonomous to the max -- to the degree that they would never work for anyone, ever. This type of thinking prompts many recent grads to ask if entrepreneurship is really for them since they feel like they might want to work for someone else first, before they start their own enterprise. They want or need to test-drive the entrepreneurship proposition first. 

So that perfectly brilliant people won't be turned off from pursuing their dream or labor under the assumption that to be an entrepreneur, they must be all or nothing, founder or employee, I sought the perspective of some entrepreneurs, founders and staffers at startups. 

LP Maurice, the CEO and co-founder of Montreal-based bus travel company Busbud, tells me he thinks that first working at a startup is helpful for those hoping for eventual new-business launches. Those who come to know and understand the unique challenges and opportunities faced by startups are much more likely to succeed in their own endeavours later, he says.

Through his mentoring work, Maurice has seen firsthand the confidence gained by would-be entrepreneurs and the  insights they unearth about previously unidentified skills and gifts after placing themselves in a challenging startup environment. 

Related: 9 Lessons You Won't Learn in Business School

Toronto-based Satish Kanwar, director of product at Shopify, an Ottawa company that offers software for creating an online store, speaks of the opportunities found by those who choose to work in a startup before taking the plunge themselves: “One of the best things someone can do is date a company first to see if you like startups and the entrepreneurial space before you commit to it,” he says.

Kanwar and Maurice are co-organizing Thursday's Startup Open House, staged simultaneously in Montreal and Toronto, with the aim of accelerating this kind of speed dating between startups and students, young professionals and would-be entrepreneurs. More than 3,500 participants will get a look behind the curtain at some 250 startups to see what entrepreneurial life is all about. Hicham Ratnani, COO of Montreal-based men's clothing ecommerce startup Frank & Oak, wrote me that the event is a great vehicle for gathering up entrepreneurs “to discuss and share big wins and opportunities." 

This idea of dating before committing is good for both parties. It can also be a great opportunity for startups to find the very best talent.   

So if you're considering a career in entrepreneurship, opt for one of these three ways to discover if life in the startup world should be your next big step:

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1. Simply go ahead and start a company.

You could say just launch your startup, saying, Screw it. Let's do it! This is also known as the blind date method.

2. Work for a relative's or friend's business.

Perhaps Aunt Selma’s flower shop needs a front-counter person. Try out working for a startup or small business. This is akin to being set up on a date.

3. Immerse yourself in the startup scene.

Try "speed dating" by checking out an open house event attended by entrepreneurs or finding a co-working space and sitting in the coffee area to chat up those nearby. Then figure out which company might be a good fit for you in providing valuable experience. This approach to learning about startups is akin to using dating app Tinder.

In the end, there is great value to finding where you fit in along the entrepreneurship spectrum. So if you're wondering, just put yourself out there. Go date a startup.

Related: What I Learned From Being a Broke, Unemployed Graduate