What I’m stealing from the startup world

By Christine Wong

My new boss woke me up at 2:30 a.m. last night demanding that I do some work for him.

After I changed him into dry pajamas, put clean sheets on his bed (the Thomas the Tank Engine ones had pee on them) and read him one Curious George story, he finally let me go back to sleep.

Technically, I guess he’s not really my only new boss. He’s just one of them. The other new boss I have is me. I am now my own startup.

Ben: He kinda is the boss of me.

After writing about the startup scene for the past year and a half, I’m now joining it, not in the technology sector but in the sense of starting my own freelance media business. Here’s what I’ve learned from the startup world and plan to incorporate into my own new venture:

It’s not going to be easy. The day you decide to give The Man the heave ho and strike out on your own, it’s high fives all around. But a startup venture means less infrastructure, fewer resources, no employee benefits, no coworkers to bounce ideas (or dumb jokes) off of, no access to expensive kickass enterprise grade IT, no IT department uber geeks to come to the rescue when your WiFi’s down, no corporate structure to back you up both figuratively and literally. The startup founder is ‘It’ and the buck (or lack of bucks) stops with him or her.

You have to be tenacious. How many times does the average startup get turned down for VC or angel funding? Or apply and reapply to an incubator or accelerator? Or contact media types to get some buzz started about their company? Lots. And lots. And still more. (Note: See important appendix to this item below under “Be prepared to shift gears.”)

Bootstrapping is key. At least in the early stages. When every penny spent comes directly out of your own pocket (or indirectly out of a startup investor’s pocket), it pays off to spend wisely and sparingly. So I will not be rushing out to acquire that $1,995 leather, elk hair and tubular stainless steel retro office chair featured in the Globe. For now.

Storytelling is selling. The best story pitches I’ve had from startups always entail great storytelling. Not just “here’s a press release; all the information is in there” kind of stuff. I’m talking about setting up a compelling story that somehow personalizes the company, its founder(s) and its product. If you want to sell your startup to potential investors and customers, figure out the intriguing human part of the story that’s in there waiting to be told. Then tell it well and tell it often.

Be prepared to shift gears. I’ve written about startups that basically died out because they either didn’t realize there was no real market for their product or simply refused to give up on a weak idea. But I also just wrote about Spently, a Toronto startup that switched from a focus on the broader mobile commerce space to a smaller niche creating enriched digital receipts that can be used as marketing tools and delivered to shoppers via email. They saw their space getting crowded and figured out a narrower spot they could really try to make their own. That willingness to refocus and refine your strategy is sometimes the ultimate key to survival.

The lines between startup life and real life are blurry. For startups, resources are usually so tight that every waking moment has to be spent on ways to develop, market and sell the fledgling product. That means missing Aunt Lillian’s birthday dinner or working through the night or getting friends and family to be guinea pigs in testing the latest incarnation of your app, social media site, crowdfunding platform or whatever.

And that’s why Ben, even though he’s only three and a half (in both years and feet tall), is really my second boss (assuming I’ll be my own ‘first’ boss). Since I’ll be working from home, there will be times when I have to interview CEOs on the phone while he’s at home beside me sick. I won’t have the resources to always juggle my own Me Inc. startup business and Ben Inc. as easily because my house will be my office as well as the unfortunate setting for a series of potty training accidents.

Technology is your friend. When I started working here 18 months ago I didn’t know big data from Big Daddy, RAID was just a bug spray (not a data storage system) and the cloud was only where rain came from. Now I’ve learned that mobile and cloud-based technology – from Dropbox to smartphones to Wave Accounting – has made it easier than ever before to get a startup off the ground.

Embrace the freedom. Starting a new company or venture gives you a blank slate. So appreciate the opportunity to write whatever story you want on there. Expect it to be tough but don’t forget to enjoy the best parts of it either.

Remember who helped you. Canada’s startups have formed an impressive community whose members support each other in countless ways. In that spirit, I will thank everyone at, parent company IT World Canada, and sister site Computer Dealer News, especially Fawn Annan, Michael Atkins, Brian Jackson, Dave Webb, Paolo Del Nibletto, Brian Bloom, Howard Solomon and Tyson Dover.

Thanks also to others who inspired me with their own work within the media or startup fields, including Jill Dempsey, Mark Evans, Michael Tippett, Andrew Deluce, Andrew Macdonald, Mathew Ingram, John Reid, Victoria Lennox, Shane Schick, Nestor Arellano, Harmeet Singh, J.D. Speedy, Jeff Jedras, Alyssa Richard, Heather Payne, Lauren Schneider, Valerie Fox, Julie King, Christine Dobby, Krista Napier, Aliza Pulver and too many others to fit into this space.

Christine Wong
Christine Wong
Christine Wong has been an on-air reporter for a national daily show on Rogers TV and at High Tech TV, a weekly news magazine on CTV's Ottawa affiliate. She was also an associate producer at Report On Business Television (now called BNN) and CBC's The Hour With George Stroumboulopoulos. As an associate producer at Slice TV, she helped launch two national daily talk shows, The Mom Show and Three Takes. Recently, she was a Staff Writer at and is now a freelance contributor.

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