How to get past what’s holding you back from starting your business

As a professor of entrepreneurship at the Ted Rogers School of Business at Ryerson, mentor, venture capitalist, international business speaker, and columnist for Inc., I meet and interact with more than 1000 “wantrepreneurs” (first time founders on the cusp of starting a startup) every year. They have loads of different reasons for wanting to launch a startup, but 5 come up again and again:
1. Job satisfaction
2. Personal success
3. Freedom & flexibility
4. Happiness
5. Money

While I don’t completely buy into the order above, these motivations are pretty standard across most of the people I come in contact with. More and more people talk about their employment as indentured servitude; they’re banished to a cubicle, working to enrich others. The word “job “ has become a four letter word to many of my students and few expect to be employed full-time for their lifetime. Most dream about monetizing an unmet market need and becoming the next TikTok, Tinder or Uber.

So what’s holding them back? Why not start a startup?

New entrepreneurs get stuck on any number of things. But from my experience, the biggest obstacles these future entrepreneurs see fall into one of the following five categories:
1. Finding a cofounder
2. Training and education
3. Fear of failure
4. Knowing where to begin
5. Funding.

While I can completely understand the items on the list of motivations above, I have a much harder time buying into the hurdles on this list, especially because today, so few remain true.

With pedagogies that include the “Lean Startup” and “Design Thinking”, the road to customer discovery and validation is now well known. In fact, it is that road that 100 Steps 2 Startup follows. The program helps founders learn how to start a startup, step-by-step, so the ‘training and education’ and the ‘knowing where to begin’ – issues 2 and 4 – are not issues at all.

Similarly, the Issue around funding (reason 5) should no longer be an obstacle to anyone. The cost to starting a startup – testing the assumptions in your business model – can now be done for less than $500. In the “olden days” (like 1998), if you wanted to start an online jewellery store, it would take you months and millions. Fast forward just two decades and now, it would take just $50 and a weekend to launch a jewellery store on

Looking for a co-founder? That’s a relatively easy one to overcome too, given the dozen “founder dating websites” online. These contain profiles and connections that could be vital to establishing your founding team.

So that leaves only the fear of failure. To address that, I can only quote the great Wayne Gretzky: “you always miss 100% of the shots you don’t take”.
It’s true. When starting a new venture, you may fail. But you will 100% fail if you never start at all.

So be brave, take the first steps and get venturing.

Sean Wise headshot

About the Author

Dr. Sean Wise

Dr. Sean Wise is a best-selling author, venture capitalist, award-winning entrepreneurship professor and serial entrepreneur. He spent two decades in the venture capital industry, specializing in supporting high-growth ventures at the seed stage. Dr. Wise was named Mentor of the Year by Startup Canada in 2014. He has written six books and hundreds of articles on entrepreneurship, with work appearing on or in Forbes, CNBC, CNN Financial, The New York Times, Fox News. and the Globe and Mail.

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