Failure Diaries: Jennifer Myers Chua

Jennifer looks back at her first big business failure, and how it influenced the success of her current venture.

Dottie Omino
Fuckup Nights Toronto
10 min readSep 29, 2017


Photo by Emily Doukogiannis via Emily D Photography

Tell me a little bit about yourself…

I’m Jennifer Myers Chua, and I’m a Creative Director and Partner at Hip Mommies. We’re a Canadian distribution company that focuses on baby, toddler, and pet products for happy and healthy families. I own the business with my husband, Joey. As part of my job, I scour the globe looking for thoughtful, practical, and intelligently-designed products manufactured in an ethical and responsible way. We then partner with these suppliers to bring their products to families through Canadian retailers. So I work with my husband, I have a toddler, and I’m really passionate about providing Canadian families with the best choices through Hip Mommies.

Who inspires you and why?

Lots of people! But on a day-to-day basis, it’s mostly other parents. I work with a lot of mom entrepreneurs and I find them inspiring because, honestly, it’s really tough owing a business. And when you couple that with the lack of sleep and other psychological impacts of raising a child, it’s even harder. But then, these women do unbelievable things all the time. They go above and beyond to develop these wonderful products that are safe for your little ones. It’s really outstanding to see that in person.

Looking back at your life so far, are there any pivotal moments that helped shape your life or who you are today?

A few moments come to mind. The first was back when I was working towards becoming a chef. I’d moved to Toronto and decided that I wanted to try waitressing to see what the other side was like. One thing I realized was that I’m a terrible waitress [laughs]. But, another thing I noticed was that I was spending a lot of time in the manager’s office designing new menus or signs for our special occasions. That’s when I realized that I loved the creative side of things, and I needed to go to school for something like that.

Unfortunately, I didn’t get into my first choice of Photography, and ended up falling into New Media at Ryerson by accident. There was a clerical error, and they told me they’d find something for me and move me — I just needed to stay there for 2 weeks. This led to another pivotal moment; I actually ended up loving New Media. I stayed for 4 years, got my degree, then started my first business.

Are there elements of your upbringing that have influenced your perception of failure?

When I was a little kid, my dad started a business that he ran with the help of my family. Over the next couple of years, he grew the business and started franchising. By the time I was around 7, he had 47 franchises, so we lived large for a couple of years. But then, my dad made a tonne of epic failures. For one, he put all his eggs in one basket; he depended too heavily on one supplier who ended up going out of business and taking him out with him. He’s also always had some complicated challenges with alcohol and addiction, and he let that take over. So around the time I was between 9 and 15, he started losing everything. We lost our big house, my parents split up, and my mum, sisters, and I moved into a tiny rental. My dad was ashamed and he stopped speaking to members of our family, so we lost family as well.

That experience made me very conscious about failure and what could happen as a result. It made me cautious and definitely affects some of the decisions I make in business. But, it’s also always been a driving force for me. My dad grew up with nothing, really. He didn’t have anything handed to him, and he didn’t have an educational background, but he managed to make millions of dollars before he was 30. So that’s always been back of my mind. Yes, my dad messed up; but if he was able to make a life for himself with nothing, any of us can.

Can you walk me through the failure story you’d like to share today?

When I got out of school, I decided to start a design agency with my boyfriend at the time and his brother. We were pretty young — I think I was about 25 — and we took some big leaps. We rented this swanky downtown loft to use as an office and hacked a living space on top of the bathroom. We reached out to these people who were huge in their industries and just kept trying to get their business. We went to all these crazy networking events to meet people and make connections. And we did pretty well.

At one point, the movie The Secret came out, and we happened to know someone who worked on it. This person told us about some people from California who were making a sequel. They had some interesting connections to Hollywood, so we thought they were pretty legit and we reached out to them. Over a series of Skype meetings, we agreed to partner with them on the brand and creative direction for this movie. They gave us massive amounts of work from designing the posters, packaging, and all the affiliate marketing requirements, to designing both of their personal websites. We negotiated that we’d be paid a certain amount which was really low — just enough to cover rent. But then, we’d get profit-sharing once the movie came out. So naturally, we agreed to everything and worked on the project for almost a year. It was great — we were so excited and passionate about this movie.

Eventually, it was time for the movie release. They were doing the premiere at the Palms Hotel in Las Vegas, so we flew down to attend. Robin Leach was covering it, Evander Holyfield was there, the billboard I had designed was on the Las Vegas Strip, and I was losing my mind! This was everything I’d ever wanted — our business was doing great and we’d just done this huge package for this huge movie. It was all so fascinating. So we arrived at the premiere and went upstairs to the private party they were hosting for those involved in the making of the movie. We introduced ourselves and everyone was kind of shocked because we were so young. They thought we’d been in the industry for a very long time, so they’d expected us to be much older. I noticed that they started treating us differently, but I didn’t pay too much attention to it. Unfortunately, the movie was atrocious; it was badly shot, the production quality was terrible, and it wasn’t actually affiliated with The Secret. We knew at that moment that the movie was going to be a huge failure, but we still expected to get something out of it. We had our contracts, and we were sure some people would still buy the DVDs.

After the premiere, we packed up and left for Southeast Asia. We’d decided to move our company there because Southeast Asia has some awesome designers, and we knew we could pay our subcontractors a good wage and live pretty cheaply there. We’d been in Bangkok for about 3 weeks when we realized that the production company was ghosting us. We’d reached out to them multiple times asking about the sales, but there was radio silence. Finally, we got a letter from their lawyer basically destroying our contract. We didn’t know better at the time, so we just dealt with whatever they gave us. We didn’t consult our lawyer, and we didn’t understand what kind of clauses can break a contract later — we were so naive and so green that we honestly just thought this would work. We’d put in a year of our lives, so we clearly thought we were gonna get paid for it! I think that when they realized that we weren’t as big as they thought we were, and that we probably didn’t have lawyers, they knew they could stick this California production lawyer on us and destroy our contract. And so we ended up getting nothing.

Wow — that must have been devastating. What was the emotional/psychological impact of this experience on you?

I was gutted. Gutted is the word. And I still feel that feeling nowadays when I hear of similar things happening to my clients. It’s just like this pit in your stomach and this feeling of betrayal at how unfair the world can be. I had this optimistic and naive view that there’s a perceived sense of trust when you give someone work. So I was really shocked that they could take advantage of us — especially since I felt like we had a relationship with them. The experience also broke up my relationship, and ended our business. It was really upsetting, and it took me a really long time to heal from that. After a year in Southeast Asia, we came home and had to start over.

Failure is not the be all end all; I think it only makes you a richer person overall.

What helped you get to that point where you were ready to embrace your failure and move on?

After I got back here, I realized that my whole life was different. Before, we’d had this swanky loft, business had been great, and everything was awesome. But then, all that was gone and I was renting a single room — so it was like a real starting over. At one point, I decided that I didn’t need any of that stress anymore. I saw that many of my friends from school had taken jobs, and that they were happy and successful. It made me wonder why I hadn’t just done that instead. So I decided to quit entrepreneurship and started looking for a job. Luckily, I found one in television broadcasting — on the digital side — and I stayed there for 6.5 years.

What encouraged you to try entrepreneurship again?

My husband had been bugging me for years to come on board with him, but I was hesitant. I loved my job — I was a team lead at Food Network Canada and I really enjoyed working with other designers. But then I went into work one Monday morning and I was let go. I was crushed. A few days later, I was very happy to find out that I was pregnant — and very scared about my future. At that point, I started interviewing like crazy. But at all the interviews, they would ask if I was ready for 60-hour workweeks. I realized that I couldn’t do it; I was going to have a baby soon, and I also wasn’t sure if I was down for 12-hour days anymore. So when my husband asked me to come on board again, it just seemed like all the puzzle pieces fell into place. It was the perfect scenario.

What made helped make your transition back into entrepreneurship easier?

It was really tough and scary knowing that I was going to do this again — that I was going to take those risks that come with entrepreneurship. It was a huge test of courage to get back in there. But my husband’s support, encouragement, and trust helped me a lot. When he asked me to join him, he said that I could do whatever I wanted to transform the business — whatever it took to make me happy. And so I did. I changed everything. We dropped all our lines, got new lines, changed the brand, the website, the online store, and the online ordering system. We basically did a massive overhaul and completely revitalized the business. Also, having learned from my past mistakes, I became really obsessed with working with good people that have good intentions. So we now work with amazing people who we can trust, which really makes all the difference.

What were some of the biggest lessons you took from your failure?

Never compromise your values. Lots of people contact us everyday wanting to do business with us, and all we have to do is run each application through our values test. Are their products thoughtfully designed? Are they ethically manufactured? Do these seem like good people? Are they giving back? When we do this, we greatly reduce the chances of making a wrong decision. When I was 25 and I was presented with the biggest contract or potential opportunity of my life, I just took it without doing my due diligence. I think if I had taken my time and done my research, maybe I would have seen that these men didn’t share the same values as we did.

And what about the legal side of things? What advice would you give on that?

I think getting a lawyer on board — even if you think you can’t afford it or if your business is brand new — is helpful. Just get someone to draft contracts for you, or at least get someone to review your contracts, so that you’re protected. In my case, with the production company, I really just didn’t consider that this could have been an issue. I should have had a lawyer review the contract before I signed it. It probably wouldn’t have been that big of a financial burden, and it would’ve saved me a lot.

If your child was reading this, what are the things you’d want her to know about failure?

I definitely want her to fail. I need her to know that you can make huge mistakes, and as long as you’re willing to apologize — if necessary — and do what you have to do to get out of that mess, you can move on. Failure is not the be all end all; I think it only makes you a richer person overall. It opens your eyes to a lot of different things in the world, and it gives you strength, self-confidence, and courage — all the attributes you hope your child would have. So I want her to fail and experience the range of emotions that come with that so she can grow.

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Dottie Omino
Fuckup Nights Toronto

Operations @Amidship. Passionate about creating user-centered products and experiences. Intersectional Feminist. Highlighting women in tech @