Skip to Main Content
The Review

CBC Dragon Michele Romanow, Upside’s Jennifer Couldrey on bouncing back


Tag Archives: Dragons Den

CBC Dragon Michele Romanow, Upside’s Jennifer Couldrey on bouncing back

Life as an entrepreneur is tough. Constant bootstrapping, non-stop criticism and never-ending capital raising can be overwhelming.

For those that make it — the Bezos, Musks and Zuckerbergs of the world — fame and fortune await. For those that don’t, failure can be a financially (and emotionally) crippling nightmare.

That puts a lot of pressure on founders to always be selling, dealing and, more importantly, winning. But sometimes failing can teach an entrepreneur their most useful lessons. In a world where more than half of all startups shut down knowing how to bounce back has quickly become a badge of honour instead of embarrassment.

If you’re going through a hard time or just not sure if you’ll make it through 2018 here’s some advice from the pros about how to beat back the bad times.

The f-word

Michele Romanow knows better than most the demands founders face. The e-commerce entrepreneur has launched four successful companies before the age of 30. She also regularly wheels and deals investment money as an investor on CBC’s hit show, Dragon’s Den.

When things go south it’s easy to turn negative, but surrounding yourself with entrepreneurs who see the bigger picture and can offer up advice is crucial to long-term success. Invest in people and resources that can help you deal with the inevitable ups and downs ahead of time. “It’s important to have great co-founders and surround yourself with other entrepreneurs who have been successful,” she explains.

“I think when you have people who have done that it makes it so much easier to remind you that ‘oh, there was this time that didn’t go right, but it got better. You always have to be swinging for the fence.”

Keeping your ego in check is also important. Most stories about high-flying entrepreneurs that go from rags to riches gloss over the dark times. Understanding that success doesn’t happen overnight will light a fire under your belt. “You go to 100 meetings and you get three term sheets. That means you’re gonna hear 97 nos and every time you hear a no you have to keep going.”

The art of bouncing back

Jennifer Couldrey works with startups every day.

As the executive director of the Upside Foundation — an organization that inspires high growth companies to give back by donating equity to charity — she gets a first-hand look at some of Canada’s best up-and-coming startups. Sometimes they succeed and end up giving back, but other times they fail.

When it comes to failure she believes investing in personal relationships can act as a great way for entrepreneurs to take their business to new heights. While putting in hard work is important, personal connections can help a business get back on track when it loses its way.

She knows first-hand how real-world connections can help an initiative succeed. A social media campaign she created for “Giving Tuesday” in the organization’s early years failed to take off because few people knew how to engage with the foundation.

“It absolutely did not work the way I wanted it to, but what it taught me is that you can’t depend on the internet to make things happen,” she says. “Especially in the early days, everything is about relationships. It’s about having those connections. Most people who contributed to the campaign did so because I asked them to,” she explains.

Finding people who can help

Couldrey’s experiences are a good lesson for entrepreneurs who can’t seem to find traction for their company’s products or service. “You can move online, use social media and automate things once you have a core set of established relationships, and then use tools like Twitter to maintain and enhance relationships. Until you have those initial in-person relationships you can’t think people are going rally behind you.”

Meanwhile, personal relationships also help ward of self-doubt. In a world where mental health is rarely discussed one-on-one relationships help entrepreneurs ensure that professional failures don’t encroach on their personal life. An entrepreneur’s self-worth should not be dictated by their company’s failings.

“A lot of people wrap up their identity in the success off their business. You have to delineate so that if your company fails you don’t feel like a failure as a person. You have other areas of your life where you feel valuable, like in your personal relationships, so you can keep going when things go wrong.”