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Three Ways My Failed Startup Benefited My Career

I left the corporate world to build my own company — but I returned when I realized I could have the same ground-up impact even without the 'founder' title.

I started my career studying computer engineering, but the longer I spent in front of a computer coding, the more I found myself drawn to business classes. I became absorbed in a business’s foundational issues: strategy, commercialization, and financing. Instead of focusing on the technology behind a business, I wanted to focus on its challenges as a whole.

Fresh out of school, I joined an entrepreneurial investment bank. The Canaccord Genuity banner was effectively a license to operate — we helped companies from around the world raise money and make strategic transactions. While I was there, Canaccord became Canada’s largest independent dealer. Concerned about losing my entrepreneurial drive within a financial juggernaut, I made the move to a smaller, boutique investment firm. When that company retrenched to Toronto in 2012, I side-stepped, joining Chrysalix Energy Ventures to learn the ropes of asset management.

After advising founders for almost a decade, I was still gravitating toward entrepreneurial opportunities. That’s when a buddy and I came up with the idea for Coastr — a platform designed to help retailers better engage with clientele via mobile, Bluetooth, and social media. We wanted to personalize the service industry by connecting serving staff with patrons. Some of our early investors called it “Aeroplan for the restaurant industry.” Coastr quickly became the most challenging career move I’d ever made. For the first time, I was responsible not just for doing my job well, but for ensuring that my employees would make rent. I did everything I could to keep my company afloat: I moved back in with my parents, I never took a salary, and I worked around the clock.

Cut to today. Coastr didn’t pan out, and although I’m no longer pursuing my own company, I’ve found a place within an established organization where I can have the same ground-up impact I was seeking — driving change from policy through to technology adoption and helping countless companies succeed. Here are three big lessons I learned along the way.

1. Being an entrepreneur isn’t just a profession; it’s a mindset.

I wrestled with the decision to return to a corporate role because I craved the rush of driving a team toward a common goal and seeing immediate results. It turns out that I didn’t have to give that up when I finally let go of Coastr. Back in the corporate world, I found the tenets of entrepreneurship were still highly applicable and would help me ultimately succeed.

Entrepreneurship gives you a comfort level with risk, an eye for the bigger picture, and a knack for capitalizing on quick wins that lead to larger opportunities without getting distracted by shiny objects. According to a survey by the National Association of Colleges and Employers, entrepreneurial traits are the most sought-after skills by employers. I rely on my entrepreneurialism as often today as I did when I was sharing a 100-square-foot office with my co-founder back in our Coastr days.

2. Build yourself a runway — then double it.

Canadian businessman and philanthropist Milton Wong once said: “Money’s only good for buying freedom.” And he was right. It’s important to feel supported and safe while you’re figuring out your next move.

Building a business is really, really hard. It’s going to cost you even more in time and money than you anticipate, and getting to a point where you can pay yourself a decent salary is likely a long way off.

I assumed raising money would be easier than it was. Everyone wanted to be a part of the next round when we had proven a market fit. I learned the hard way just how critical it is to build out a financial buffer of at least a year. At Coastr, we needed more room to pivot and make dramatic changes to our platform, but we were living month-to-month off of personal savings and small investments from friends and family. I was constantly balancing a long-term strategy with proof of short-term momentum. Investors wanted to see more than the lines of code that had been written; they wanted to know how many customers had signed up and how many users had been onboarded. Meanwhile, I was trying to figure out how I would pay my team’s salaries. Had we built up enough of a buffer, we could have taken a step back and made big changes when necessary.

3. Keep your personal goals front and center.

Whether you’re part of a multibillion-dollar organization or you work at a two-man taco truck, the ability to recognize what you’re chasing, and why — both in your career and beyond — is vital. Building a business requires sacrifices, but your family, your integrity and (bad days aside) your happiness shouldn’t be among them. Your core goals should always be clear and aligned with your greater priorities. If not, it’s time to recalibrate. Secondary only to passion and tenacity is an entrepreneur’s acceptance that it’s okay to fail.

If you’re entrepreneurial, it may feel like you’re stuck choosing between joining something bigger or building something from scratch — I know it seemed that way for me. But entrepreneurialism isn’t squandered just because you don’t have a “founder” title. Use each experience to inform the next big decision, and learn everything you can about yourself along the way — including when something isn’t the right fit. It will help you come out on the other side with something you can be proud of, even if that includes a failed startup.

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