Blog January 6, 2020

Posted by Brittany Arbutina


“How do you know when it’s time to pull the pin?” Jacky Martin, managing owner of JetSitters, reflects on a conversation she had with another entrepreneur earlier in the week.

“You need to be able to recognize that you’ve tried all the alternatives and now it’s time to call it.” Jacky has had experience with a few other start-up companies and understands the nature of the grind. There is good grinding and bad grinding, “you could have a great idea but if your audience isn’t picking it up, maybe the timing just isn’t right.” This wasn’t JetSitters’ problem.

Big White Sitters, the company’s original name, had only seen a single season of business and was up for sale. Jacky bought it for $500, changed the name, and added enough automation and new sitters to see $30,000 in revenue in her first year, 3x more than the previous owner. “We were lucky to tap into something that made sense—parents needed this service,” Jacky recalls, “I didn’t see that kind of immediate traction with my previous businesses.”


Over the next few seasons, JetSitters would expand to provide pet sitting and baby equipment rental. Other services were trialled but a lack of interest kept them from returning another season. Jacky knew the value of failing fast and not getting stubbornly attached to ideas that weren’t working, something her time in Accelerate Okanagan’s startup programs emphasized.

JetSitters’ problem wasn’t needing more money, activating their audience, or finding enough sitters—it was insurance. “Insurance companies want the lowest risk possible.” Even though they were profitable, incorporated, never had a claim against them or an issue with a sitter or customer, 21 insurance companies turned down JetSitters’ requests. Similar services, who didn’t take the same precautions they did, were driving up the cost of insurance and making companies fearful of covering the startup. Jacky recollects that one claim against a competing service went as high as 4 million dollars. “I want to provide that quality care assurance to our customers and our sitters so they can feel safe using our service,” Jacky explains, “but the cheapest policy we were offered was $125,000 a year. How does a small business work through something like that?”

There’s something to be said about being honest about your business, taking off the blinders and admitting when you’re vulnerable

To address the looming threat of an expensive insurance cost, JetSitters has expanded its reach to four new ski hills. Now, Whistler, Silverstar, Sun Peaks and Banff all have access to JetSitters’ services. “It’s a race between building the business and it’s revenue [to afford the cost of insurance] and not finding ourselves in a catastrophic insurance event,” she explains. “What comes first, 20 successful locations or complete annihilation?”

Jacky’s earlier conversation about pulling the pin comes into a whole new light—how do you emotionally separate yourself from the business and recognize when it can’t move forward anymore? “Depending on how things go [at the new ski hills], I need to determine whether I pivot out of this business and chalk it up as another learning opportunity or start making money, get insurance, and pay my employees a proper wage.”

“There’s something to be said about being honest about your business, taking off the blinders and admitting when you’re vulnerable,” Jacky mentions as our interview winds to a close.  “There’s always a fire. Every day it’s something different. That’s what keeps me going.”

After an exhaustive search, Jacky was finally able to find an insurance company willing to take on JetSitters. Jacky will now be able to provide peace-of-mind for her customers and sitters that her competitors cannot. To accommodate the insurance company’s needs, JetSitters will also be expanding into the United States in the coming year. With a pragmatic mind and strong determination to benefit all involved with her company, Jacky continues to push JetSitters towards the growth it needs to thrive.

Entrepreneurs, like Jacky, are all experiencing setbacks, failures and daunting obstacles. This is the nature of startups, it’s the nature of building something out of nothing. Carving new paths where there was no road is never easy, there are obstacles and dead-ends around every corner. That’s what makes the journey so worthwhile when you finally breakthrough.

Let’s celebrate those challenges together.

Connect with Jacky and learn more about JetSitters.

Connect with Brittany to learn more about our Venture Accelerator Program for startups.

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