Most small business owners look at the challenges they endured in their early start up days as a presumed rite of passage. In the face of adversity and against all odds, they’ve persevered through hard work, dedication, sacrifice, and grit – all while facing a seemingly endless gauntlet of trials, tribulations, and even self-doubt.

If you’re like most entrepreneurs, you’ll find it hard to relate to your traditionally-employed peers with respect to the unique challenges you’ll encounter throughout your career. While this can often lead to feelings of isolation and uncertainty among small business owners, rest assured, you are far from alone! We reached out to 8 pros from across the industry to ask about their start-up stories, the challenges they’ve faced, and how they’d do it differently if they had to do it all again.

Unlike many other venues, we were not backed by a corporation. We were just two gals with a dream! With no capital and minimal venue experience, we dove in with both feet, determined to make our first location work. My partner Shannon and I rolled up our sleeves and put in the time. We painted, lugged, sanded, cleaned, and outfitted The Jam Factory with our own blood, sweat and tears. We started taking venue tours immediately and used the first booking deposits to fund the renovations.

Soon after beginning, my business partner Shannon broke both wrists in a car accident. She had to be spoon-fed at our first catering tastings! With only two usable wrists between us, and an old venue wrought with logistic challenges, combined with a serious lack of funding, it was the strength of our partnership (and friendship!) that really pulled us through those early days.

Fortunately, we made some great industry connections along the way. Those relationships were and are everything to a new venue! In time we were successful enough to expand to a second location, The Richmond. Things have been smooth sailing since! There’s not much we’d do differently. Ideally we’d have secured more capital to be able to hire an accountant and venue staff sooner, so we didn’t have to burn the candle at both ends so much. But it was all character-building so honestly we have no regrets!

Photo of Kristin Light
Kristin LightHead of Relations & Revelry
The Jam Factory & The Richmond


Our biggest challenge when we first started out was trying to achieve a proper work/life balance. We take our work very seriously and it is extremely important for us to reply back to clients right away and ensure they are completely satisfied.

However, eventually, our dedication started to take a toll on our personal lives and mental well being. We realized that maintaining a proper work/life balance is extremely important and is beneficial to us, our clients, and the business as a whole. We created a schedule that we could realistically adhere to and made sure to stick to it! We marked off specific nights of the week which we would do all of our evening appointments. This would allow for other nights to be spent with our families. We also realized the importance of taking some days off to unwind and recharge. Recharging allows us to maintain the focus and creativity our clients expect and deserve. If we had to start over again, we would try to establish the proper balance from the get go, so as not to get overwhelmed and burn out. It’s very important to take time for ourselves so that we can continue loving what we do and we wish we knew this lesson from the beginning.

Photo of Michelle Garber
Michelle GarberEvent Planner
Fab Fete Planning Boutique


The biggest challenge I faced when starting up my company was the ability to stay positive through the inevitable roller coaster ride experienced by start ups. Experiencing wins and validation of concepts was an incredible rush, but it took a lot of effort to navigate through insecurities both personally and from those around me who couldn’t understand why anyone would risk everything in exchange for an uncertain new path. The confidence to persevere through the unpredictability of managing expenses, people, investment, and cash-flow was key along with the realization that I couldn’t do everything myself. I was stronger when surrounded by the right support team. I sought guidance from other mentors, listened carefully to what my customers wanted, and carefully analyzed what was working within my own practices as well as in the larger industry.

Constant continued learning by embracing self realization techniques have been instrumental in reinforcing confidence and keeping me connected to my purpose and passion. I believe the most effective way to learn is through careful analysis of our mistakes. To do so without judgement of self or others is one of the most important things I've absorbed along the way. Likely only possible by having experienced those early challenges.

Photo of John Henriques
John HenriquesFounder and Executive Producer
Images Life Media


I found that I was most challenged with finding my niche in the industry. For me, it was really finding out WHY I was doing what I was doing, what I wanted to focus my attention toward, what type of client I wanted to attract, and how I was going to achieve my goals. Of course, figuring out my niche came from doing a lot of everything and realizing what I hated (like cake pops and donuts) vs. what I loved (painting cookies!). At first, I stressed that not offering my clients each and every option requested would cause me to lose business and send clients elsewhere; in fact, it did just the opposite! I focused my business based on what I was best at and didn't cut corners on execution. This also allowed me to then partner with other like-mind companies whose strengths supplemented the areas of the business that I chose not to focus on (like cake pops and donuts).

If I could do it over again, I would have stopped trying to please everyone all the time. A client who gets you to take them with one day's notice expecting a quick turnaround will not learn to book earlier next time, and making things that aren't offered on my website is just going to cause me more stress than it's worth. Bending to those demands doesn't build my brand nor does it help the client understand boundaries. I would have created the contracts, a pricing list, and business practice rules right from the start and taken myself more seriously. I have since learned so much from my failures, so I don't regret any of it. The important thing is not to waste the lessons it has taught me.

Photo of Christina McKenzie
Christina McKenzieFounder
The Cocoa Cakery


The wedding industry is steeped in tradition that date back centuries. So, my biggest challenge in disrupting an established market like the wedding industry, was two-fold: Firstly, I needed to gather enough research information to know that our service would be embraced by our target market, and secondly, we had to develop strategies to attain sustainable growth targets. We spent months engaging with couples learning what they wanted, as well as speaking with other industry professionals so that when we launched, we already had a reputation in the space.

In the beginning when something went wrong or didn’t work out as planned, some doubt would sneak in. That said, I had a trusted support group of family, friends and other entrepreneurs who knew my goals and who objectively offered their thoughts and direction about the business. Their input helped assure me that we were on the right path and gave me the emotional fortitude to persevere when things weren’t going well.

Time management is essential to the success of any business. So, if I was starting over, I would manage my time more efficiently. I would focus more on planning and developing strategies while outsourcing and/or delegating day-to-day tasks.

Photo of Jim Emerson
Jim EmersonOfficiant
Enduring Promises


When we first opened Encore Catering getting exposure was a challenge. It was all about building credibility and trust in the community. Our mission statement has been the same from day one: to deliver a memorable food experience and a flawless event which exceeds the client’s expectations time after time - hence Encore.

At first, we did anything to receive exposure and flaunt our food. We quickly learned that credibility was achieved through successful events and happy customers. We’ve been multiplying our exposure for almost 40 years thus resulting in an abundance of credibility and exposure, which ensures future catering opportunities.

Photo of Cary Silber
Cary SilberPresident
Encore Catering


Pricing my service and selling was probably my biggest challenge when starting out. I wanted to be paid fairly, but lacked confidence in selling myself. It doesn't take a lot of weddings before you realize how much work is involved, and that you have something unique to offer your clients. Don't compare yourself to everyone else. Charge what you think is fair for your time, and be bold in asking for it. Don't undersell yourself!

Photo of Rebecca Chan
Rebecca ChanOwner and Lead Planner
Rebecca Chan Weddings & Events


Our biggest challenge when we started is very far from where we are today. Party rentals have evolved drastically from those early days of basic chairs and linen-covered tables to a much more modern and complex aesthetic that clients have since come to expect. Back then, customers didn’t fully comprehend that our company was renting furniture and not selling it, so educating Clients and aligning our services with their expectations was one of our largest challenges initially.

As time went on and the market began to mature, we were able to successfully get our product in front of the right people and were fortunate enough to be featured at some very high profile corporate and charity events as well as the Olympic games in Vancouver back in 2010. This propelled us and continues to fuel our growth today.

It’s been an interesting ride over the last close to 15 years and I’m not sure we would have done anything differently. Of course, operating a medium sized independent business brings with it a myriad of new challenges, but like any company, we continue to adapt just as we had when we first started.

Photo of Evan Aranoff
Evan AranoffCo-owner
LUXE Modern Rentals Inc.