We paint a picture of Jolly Productions in Episode 3 of Founders: Behind the Hustle!6 min read

4 minute read

Founders: Behind the Hustle is a video series highlighting small business owners as they share their unique stories and tell us why they’re driven to run their own businesses. Each episode provides a personal perspective on the hard work that goes into running a business, as well as the rewards that come with it.

In this episode of Founders: Behind the Hustle, we’re taking a closer look at Jolly Productions, a Toronto-based company specializing in hand-painted outdoor advertising, portraits, and sign painting. This week’s founder, Chris Jolly, discovered his entrepreneurial drive after seeing a mural painted for the first time. “Just through word-of-mouth, I just started picking up jobs. I invested in equipment, and more jobs started coming my way, and then suddenly it felt like a real business, and then I ended up getting a studio, and then…it just happened. It just fell on my lap.”

And while Chris believes that running his own small business was the right path for him, he also recognizes the risks that come with that journey.

“There’s a pretty big risk…the hours that go into the pre-production, just to mix everything and do the patterns. “We’ve had so many different things happen, where you have to think on the fly.”


And while all entrepreneurs must be able to think on the fly and deal with any surprises that may arise, it can be overwhelming at times. That’s why we’ve outlined three situations you may encounter if you run a small business similar to Chris’, and provided some tips on how to deal with them.

Handling late work or errors

No matter how much effort you put into your work, or how many times you double check it, sometimes mistakes happen. We’re all human, after all. As a result, work can sometimes be finished late or oversights can be made, like spelling your client’s name wrong on a billboard.

These types of errors could expose your small business to costly lawsuits from your clients. If a client suffers a loss because of errors in your work or they believe your service failed to meet the agreed upon      expectations, they could file a suit against your small business. If your business is found legally liable for negligence in the service you provided to a client, you may also find yourself tangled up on a long and costly lawsuit. That’s why professional liability coverage is so important, as it can help protect your business from the costs associated with these types of lawsuits.

Any business that provides a service for a fee should consider having professional liability coverage. This could include copywriters, photographers, graphic designers, web designers, IT consultants, and management consultants.


Falling victim to vandalism or burglary

It’s a scene out of small business owner’s nightmares. You head into your workshop one morning only to find the front window smashed and your equipment gone. Your space has been vandalized and you have been robbed.

While there are numerous precautions one can take to attempt to stop this from happening, including surveillance cameras, locks, and alarm systems, sometimes these steps just aren’t enough. That’s where commercial property insurance comes in. It doesn’t just protect the building you use, but a long list of things inside including equipment, inventory, furniture, computers, and other electronics. It can also protect things outside of the building including outdoor signs, fencing and landscaping such as gardens, trees and shrubs.

The right commercial property insurance policy can help with repair costs, replacement costs, and unexpected losses that occur because of natural disasters, fires, winter storms, and hail. If you suffer a loss, you may not be able to sustain operations right away. Your commercial property policy may include business interruption coverage to help you mitigate your loss of income by helping you keep up with bills, payroll and other expenses until you’re back on your feet.

Dealing with your commercial vehicle breaking down

Getting to the job is just as important as the work you do once you’re on site. Which is why if your work vehicle breaks down, or you find yourself in an accident leaving you with no way to transport yourself and your supplies to the worksite, your business could suffer.

That’s why commercial auto insurance is so important. Some of the common, standard coverage options include:

  • Injuries to you, your employed drivers, and passengers. Your commercial auto insurance policy could help with medical expenses and lost wages that are caused during a covered accident.
  • Loading and unloading liability, which is particularly important for small business owners who transport products to customers or events.
  • Replacement car coverage. If you’re involved in a covered accident and require a temporary rental car to continue your day-to-day operations, your commercial auto insurance policy can help with this cost.

Many small business owners think they’re protected under their personal policy, but it’s important to understand the differences between the two types of coverage so you’re not leaving yourself vulnerable to risk. The type of vehicle, vehicle ownership, how the vehicle is used, and whether or not you drive for a ridesharing service are all factors that go into determining what kind of coverage you need.

Stay Jolly

While the risks associated with running your own business can be stressful, it’s important to be as prepared as possible, so that you can enjoy work everyday and remain jolly. Having the right protection in place for your professional services business can help ensure that you’re not sweating the small stuff, and keep you focused on your customers instead.

We want to thank Jolly Productions for participating in our series Founders: Behind the Hustle! Be sure to visit their website, and follow them on Facebook, Instagram, Pinterest, and Vimeo to view their paintings and ads. Don’t forget to check out the rest of the Founders: Behind the Hustle series.


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This blog is provided for information only and is not a substitute for professional advice. We make no representations or warranties regarding the accuracy or completeness of the information and will not be responsible for any loss arising out of reliance on the information. Terms, conditions and exclusions apply to coverage. See policy for details.