Leaving Corporate Careers to Build a Thriving Business Empire: The Story of Olive & Fig

Leaving the security and stability of a corporate career was not an easy choice. It meant stepping into the unknown, facing uncertainty, and embracing the inherent risks that accompany entrepreneurship.

Yet, we saw this leap of faith as an opportunity for growth, self-discovery, and the chance to create something extraordinary.

Our departure from the corporate realm marked the beginning of a thrilling and transformative journey.

Armed with our individual strengths, skills, knowledge, and an insatiable hunger for success, we set out to build our own Olive & Fig business empire together!

Here’s our story, the story of Olivia and George, and the idea and determination to build a business together and inspire others along the way.

Quebec City based photographer Veronique Saint Germain,  @veronique.saintgermain


How George & Olivia Met

George and I met a few years ago when we both worked in a whimsical heritage building in Toronto.

I worked at an executive recruitment firm and George at a wealth management firm. It was a small five-storey building with a different company on each floor with approximately 40 people working in the whole building.

I had been working on the fourth floor for a couple of years so was quite familiar with everyone in the building.

Each floor had personal mail delivery (the mail man would come up to each floor to deliver the mail) and one day I came back to my desk after lunch with the third floor’s mail accidentally left on my desk (it was closest to the elevator). 

Being a small and friendly building, I was aware that a new company had moved in on the third floor not too long ago so I decided to head one floor down to introduce myself while hand-delivering their mail. 

I took the elevator to the third floor and with no one at their front reception desk, I called out a “hello?” At that moment someone popped out of their office with a big smile and of course that someone was George.

I gave him the mail, we exchanged a few words and I went back on my way upstairs. 

We did not see each other again for a few weeks.

But one morning George forgot the key to his floor so he was waiting in the building lobby for his colleagues to arrive where we were able to finally introduce ourselves and chat until the elevator arrived.

A few more weeks passed when we ran into each other on our walk to work where we had a conversation about vacations to Greece.

We got to our office building and headed up to our respective floors.

A couple of hours later, I received a call at my desk and to my surprise, it was George! He had researched the company phone number and asked me out to lunch that same day…

Fast forward several years and the George and Olivia of that time would have never guessed in their wildest dreams that they would have met in the serendipitous way they did to join forces to leave their 9-5 corporate jobs to pursue and build a business as well as the lives of their dreams.

This little business went from side-hustle to a full-fledged multiple six-figure business with four employees that is constantly evolving and rapidly growing.

We truly put 100% of our endless love, passion and hard work into Olive & Fig, just as we do our relationship. 

Quebec City based photographer Veronique Saint Germain,  @veronique.saintgermain


How Olive & Fig Came To Be

Olive & Fig was born out of months of self-care and a desire to add more to “Olivia” after a few turbulent years in my personal life.

With my corporate career in a great spot, I found myself with extra time on my hands in the world outside of work and was seeking a creative outlet. 

I have always enjoyed gathering with family and friends, hosting events and the culinary world.

Instagram introduced me to a charcuterie trend overwhelming the Australian market - beautiful, edible food art in the form of grazing boards and boxes. With some research, I realized this grazing trend had not yet flourished in the Toronto market.

There were a few companies that began operating in the same year, but I truly believed there was an untapped opportunity for me at that time and that gut instinct proved to be absolutely true. 

With my love of food and my creative knack, I thought this would be the perfect hobby that could fill my weeknights and weekends. 

The real dive into grazing came in May 2019 when I offered to create a couple of charcuterie boards (one savoury and one sweet) for my niece’s first birthday.

I had a blast creating them and even more so loved the compliments I received. That’s when I decided to become more serious about my small business by finalizing a name (with the help of George!), an email address and most importantly, an Instagram account.

The first photos posted on Instagram were the ones I created for my niece’s birthday party (pictured below) and for family shortly thereafter.


These Instagram posts generated Olive & Fig’s first non-family orders with my first-ever order being a Baby Shower grazing table that George and I completed together.

The more photos I posted, the more interest I received. Instagram was truly integral to the initial success of Olive & Fig and I am thankful that some of our earliest followers still follow us and order from us to this day. 

The rest is history!


We have come a LONG way since these first two charcuterie boards. One of our most popular boards to date is our Olive & Fig Platter.


Our Challenges & Biggest Milestones

The road to building a successful business is riddled with obstacles, and we definitely confronted several of them head-on, especially as first-time entrepreneurs coupled with being first-time entrepreneurs during a pandemic.

However, along with each challenge always came a milestone which acted like a stepping stone, propelling us further along our entrepreneurial journey and igniting the flame of ambition to reach even greater heights.


From Home Kitchen to Commercial Space - A Journey of Growth

With Olive & Fig being only a side-hustle, it was a business that operated from my Yonge/Eglinton condo until I moved into George’s Avenue/Lawrence condo in April 2020 which became Olive & Fig HQ until we decided to resign from our corporate jobs to pursue the business full-time. 

In 2020, especially during the holiday season, working from the condo was stressful, impractical and not big enough to live AND work in.

A picture of our board with our apartment view..

This set-up was driving us absolutely stir-crazy (there are SO many stories here); however, in the midst of the pandemic, it was the only option available to us at the time. 

When we resigned from our jobs and pursued Olive & FIg full-time in September 2020, we knew one of our major challenges was relocating Olive & Fig to a commercial kitchen.

Not having any culinary or business experience, we had no idea where to start.

Luckily, in January 2021, we came across a catering kitchen online that was not able to operate due to the pandemic and was seeking to offset their rental costs.

It did not take us a long time to decide on this kitchen as it was not shared space at the time, it was an optimal location (close to all highways which was perfect for our delivery business model) and the price was right for our small business. 

In the long-term, we would like a space to completely call our own vs a shared space which is a work in progress. But in the past two years, we have learned a lot about what we are looking for in a space and what we aren’t.

As our business and the world evolves, so does our vision for Olive & Fig. 

Growing and making our own charcuterie boards


Delivery Dilemmas - Finding Solutions in a Niche Market

When Olive & Fig first began, I personally delivered every product or often utilized George or my parents if I really needed help.

But when business rapidly grew, George & I were unable to make the products as well as deliver them.

This was an impossible task for us, so we knew we needed to start outsourcing this part of our business. 

We discovered yet another gap in the market - the delivery of multiple products of fresh food across the GTA for specific times.

Of course we knew there were food delivery apps but we quickly learned that their delivery model was limited to a small kilometer radius from business pick-up locations.

We moved onto delivery start-ups that emerged during the pandemic but unfortunately, these start-ups were unable to operate in the way that we needed them to.

Our products could not be delivered in the same way non-perishable products like candles and flowers are. Our products needed to be carefully hand-delivered on a certain day within a certain timeframe often for specific times. 

Our next trial was posting for delivery help in our social networks which was very successful for us during the pandemic.

While we had a lot of interest and recruited some wonderful delivery people, life eventually changed for these students, moms and dads seeking extra work and we were back to ground zero. 

During the pandemic, Uber introduced a “Connect” feature on their app which was created to help people send packages during the pandemic.

Super smart pivot for the company as people were not using Ubers to transport themselves.

We initially utilized this “Connect” feature as a way of delivering packages; however, George would “recruit” the drivers that were the most presentable and did the best job.

George would explain to the drivers what we did, obtain their phone numbers and let them know that we would like to reach out to deliver for us on a regular basis. 

After trust was established between us and the drivers valued delivering our products often commenting they derived pleasure from recipients’ reactions , these drivers became Olive & Fig’s go-to delivery option and our roster grew as they began referring their friends.

Of course, drivers have come and gone, but we have had one of our longest-tenured drivers create their own delivery company in the meantime and we now use his company, D2D Drivers, as our go-to.

Building Our Dream Team - A Testament to Trust and Growth

Hiring employees was not something I could ever fathom when I first started Olive & Fig.  

Not because I did not want to grow a team, but because I thought what I did would be difficult to teach, train and replicate.

I was happily proven wrong when we hired our first kitchen employee, our Head Chef, Jaynie.

Not only was Jaynie a quick learner and picked up Olive & Fig’ style, but she has contributed to our business beyond belief. I have to add in a relevant quote here that was posted at the commercial kitchen months before Jaynie arrived: 

“The best way to find out if you can trust someone is to trust them.” - Ernest Hemingway

Jaynie working her magic in the kitchen.

We have complete trust in Jaynie in every aspect of our business from product development, customer service, employee recruitment & training and representing Olive & Fig in the best way possible.

She has taken our newest employee, Andriana, under her wing and she has absolutely soared under Jaynie’s leadership. 

 We could not be more grateful and proud of the team we have built together. 


Cultivating a Loyal Community and Thriving Brand Partnerships

Building a business is hard, but building a community that supports your business is even more challenging.

This business was originally built on Instagram and word-of-mouth because of the personal connections we have made online and relationships we have genuinely cultivated over the years.

We are thankful to have repeat customers from 2019 that have become like family. Having recently been married, we have had some customers (some of which we have yet to meet in-person) ship us surprise wedding gifts.

It has been an absolutely heartwarming experience building a community of people who genuinely care about you and your business. 

By engaging on social media, providing exceptional customer service and a consistent, high quality product, we believe we have truly differentiated ourselves in this saturated market.

Our differentiators have landed us repeat brand partnerships with companies such as Shopify, Pinterest, Bell Canada, Fable, Canadian Tire, Microsoft, SickKids, Eli Lilly Canada, TD Canada, CIBC, ABC, among many others. 

Making custom boxes for Pinterest

We hope that our Olive & Fig success story serves as a powerful reminder that even in the most challenging times, entrepreneurial spirit coupled with passion, strategic-thinking and a customer-centric approach can pave the way for not only surviving but flourishing against all odds.

However, our journey is not over, it’s only just begun!


Olive & Fig


Leaving corporate careers, Building a business empire, Entrepreneurial journey, Serendipitous meeting, Challenges and milestones, Flourishing against odds, Cultivating a loyal community, Brand partnerships, Passion and hard work, Evolution of Olive & Fig, Entrepreneurial spirit, Success story, Strategic thinking, Customer-centric approach, Thriving against all odds

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