Worst Day on the Job: When Michelle Sklar had to close her brick-and-mortar winemaking shop

The seasoned entrepreneur opens up about the emotional and financial reality of closing her New Westminster shop—and what she learned from the failure

Michelle Sklar, head of marketing and communications at Innovation UBC and chair of Vancouver Entrepreneurs Forum, has built many startups over her career and advises budding entrepreneurs on bringing their own ideas to life. But when it came to going all-in on a brick-and-mortar winemaking business with her husband in 2019, they eventually had to make the tough call to close it down. “I have many stories about knocking on doors when it was minus 50 or selling a company under the worst possible conditions when I was under 30,” Sklar says. “Life is always about lessons, and people like to say things get easier, but I think maybe we just get better at making decisions, and sometimes those decisions are hard.”

In the fall of 2019, my husband and I bought a business. He wanted a career change and I’d mostly been the main entrepreneur, so it was his turn. We acquired a winemaking business in New Westminster—“The Wine Factory”—and were getting into this brick-and-mortar business experience. We were very excited. We love wine, we love making things and we had this beautiful space that was actually an old jail cell.

But then COVID happened. We were only three months into running our brick-and-mortar business, and we had to make a massive pivot in how we were going to build our customer base. Though it was always something that had played a big role in my job at UBC, being in this situation taught us firsthand about the importance of customer relationships and how we were going to grow that base.

It was a really tough slog. We couldn’t quite get the lift. We introduced a new product to engage a younger demographic. It was bumping along, but it wasn’t necessarily enough to sustain the overall business. Brick-and-mortar comes with so many operational costs that are different from running a software company. We were in an area that was always massively under construction. We were just not getting any reprieve whatsoever—we still see this all over Vancouver, especially with businesses on Broadway near the construction of the train line.

So, in 2023, we decided to close the business.

It was a tough day. There were a lot of emotions, as you can imagine. My husband and I have run businesses together and have done great projects together. We’re seasoned entrepreneurs, and seasoned in our own maturity, so I think a lot of it was pride. But my husband was working seven days a week. We were also at a point in our lives where we were really weighing work-life balance. A big part of that reflection was being clear on what’s important to us: having a thriving life and not being encumbered by something that just isn’t working.

When I’m supporting a company, I always share that sometimes you have to call it. But making that tough call felt like the worst day. We’d put a lot into this, we had a great community around us, but we needed to make a responsible decision. I’ve supported founders who had to wind down their businesses, and it’s hard. So, for me, it was: we’re going to get through it, and we’re going to get through it with grace, and we’re going to get through it with integrity. At the end of the day, people will remember you for that integrity.

What I learned is that it’s not always about making easy decisions. On a day-to-day basis, business owners make tough decisions all the time. We’re managing people, we’re managing vendors, we’re managing customers, all these things—and it can be taxing.

No matter what, we are not insulated from the feelings we feel and the desire to make something successful. But you need to listen to your gut. Failure is hard. We don’t talk enough about it. In our world, shame is often attached to failure. For me, today, it’s more of a badge of honour. Now when I talk to founders, I can share my own experiences of failure. We probably learn more from the things that don’t work out than we do from the wins.

Closing this business was probably one of the best decisions that we’ve made, because we needed to make it, and we needed to live with it, and we needed to be accountable to it. If I were to pursue a new entrepreneurship opportunity, I probably wouldn’t do brick-and-mortar again. Small businesses are vital, but they’re hard. Right now, I’m at a great place with my work at Innovation UBC, and my husband is enjoying semi-retirement. For anything we do moving forward, we need to answer the question “will this bring us joy?” If the answer is yes, then we will probably explore it, warts and all.

This interview has been edited and condensed.