At My Favourite Home Away from Home - The W Montreal



Welcome to my site, to my story! First off, happy 2020! These last 6 years of living an entrepreneurial life has definitely been quite the journey. If you were to ask me if I would do it all over again, without hesitation, my answer would be 100% YES; the good and bad!


Here in Canada, I am known as Montreal's girl boss but I am working on taking over the world. More importantly though, I am a sister, daughter, friend and of course, human. I have made mistakes, changed the rules and have learned lots of lessons! I don't think outside of the box... because there is no box with me. I tend to shoot for the moon, because I know that I'll fall amongst the stars if I don't hit it (this time). In a nutshell though, here is my story!

xoxo Samantha

The Beginning: Re-writing the Rules

My favourites seasons are the cooler ones.

Frosty mornings & toasty mugs.



When I was 14, I realized that I could change the rules. My sister (Tracey) and myself REALLY wanted a Trampoline! We begged our parents. "It's not your birthday!" they replied. We were determined we'd get one. We'd work hard and buy it ourselves! But how?! That same evening we walked over to the park for our baby sis ; Emma-Lee's T-ball game. Our Dad was the coach. I remember it so well. The umpire was a "no show" and the scorekeeper was freaking out. I ended up umpiring my first Softball game with Tracey. Jackpot! At 14 I became the first certified provincial Umpire under the age of 18. We bought our trampoline that Summer.


I loved working for myself, I loved being independent, I loved seeing results from my hard work. Throughout High School I had many, MANY jobs - the thing is, I loved them all so I kept them all. It was as though I was collecting them. Was it that I didn't know how to say "no" to new opportunities, or the fact that I wasn't being challenged anymore? Upon Cegep I had 7 jobs. I was an Umpire, a Math tutor, a Shadow, a Party Animator, a Secret Shopper, a Model for Soft Lips... oh, and took on the Manager job of a slipper kiosk in our local mall during the holiday break. I LOVED it!! I loved organizing, managing my team, hiring... It was my passion!







At 17, I started cegep at John Abbott College. I was in honours Science. I loved it. This was the unexpected catalyst to my bath & body company - my first company 5 years later. Learning different formulas, mixtures and elements. My sisters and I even created a body cream from scratch with ingredients from the kitchen all together that year with some of my knowledge! We all had severe allergies and eczema so this was so much fun! 

I was then recruited. It was at our local gift shop: "Le Panier", it was so popular and loved by everyone, it was the place to be! They were offering me a "big girl" salary and were extremely flexible with my full time school schedule. At first, I was unsure. They were insistent and so I accepted. Within 2 weeks I was promoted and managed a team of 7 girls - some who were even older than me. It was great! With that, I gave up my 6 other jobs... 

When I turned 18 I was head hunted.     

February 15, 2020

February 13, 2020

February 11, 2020

February 9, 2020

February 7, 2020

February 3, 2020

February 1, 2020

January 30, 2020

January 28, 2020

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School & Work


My First Taste of Marketing



A brand new chain of stores was opening in Canada. The owners and District Manager tried to recruit me as the Key Holder of Diva Canada. It was pink and white. I was in LOVE! It a full-time position. I obviously couldn't take that on with school. I declined. The next day, they came back to me with an immediate pay raise and the approval to take this position on 25 hours a week as I continued full-time classes.  I accepted.


The Assistant Manager and Store Managers were very nice. Nice, but kind of lazy. Was it because they were much older than me? No, the entourage of "older" adults in my life were absolutely not like these women. When the store was dead, they would chat… come to think of it, when it was busy, they would too! They would even comment about me coming to “hang out” and chat with them. I remember trying it. I remember 30 seconds into the conversation wanting to re arrange a wall bay, wanting to prep the Closing Procedures, wanting to organize the back-store. I couldn’t just sit around and talk. I felt like I was wasting time. I needed to be busy and productive. I guess they didn’t enjoy working with me and started scheduling my shifts in a way that would not be combined with theirs. They would work together, and I would work the opposite shifts. After a week, the numbers soared. Our store was #1. We had gone from 2nd to last in Canada to #1! Our conversion was through the roof – well on my shifts. I learned how to properly delegate to the part-time employees and it was fun! I loved being apart of a team, actually I loved leading a team and achieving the best results. On my 10th shift I walked into the store, as the District Manager Approached me. “I’ve fired the Store Management and you’ve been promoted.” I became store manager of 22 employees at 18!


At My Favourite Home Away from Home



I was the youngest manager by at least a decade, but our store was soaring - we were the TOP of all stores - exceeding our targets! The other stores were struggling though. I was then given specialty projects and would start contributing to the marketing and brand growth strategies to the other stores! I loved this company and loved the promise that I would be growing with them and transitioning to their head office by the end of the year! The following month, as I went to open up the store - the Mall Manager approached me with the news that the whole company filed bankruptcy! What?!?!


I was beyond heartbroken. I told myself I would not go back into retail - I had put too much love and energy into this company. I was really hurt! I got over it quickly, though! 


Timing was sort of right. VIA Rail Canada was hiring University summer students - I was about to start business school at Concordia University! My last 5 years in Management reinforced my love of business. VIA Rail prioritized "kids" of the Directors within so I got lucky - I got an interview and happily accepted my position in Labour Relations! My Summer was filled with working with actual professionals! Real life business men and women. I inhaled as much knowledge as I could before the Summer came to an end. 


... but when it came to an end for the students... it didn't seem to for me. They asked for me to stay on. With a real career and salary and benefits and .... YES! I worked at VIA Rail! I started University part-time. I was one of them now. Part of a team of professionals. You needed a completed degree to work at VIA....I didn't have one yet. (Rewriting the rules again - jackpot!) 


Even though I was in Legal, my tasks encompassed visual creations, graphics, web, putting together presentations and documents for my Boss. I thrived and thoroughly loved this. I got to be creative. What fun!


When I turned 23 the Marketing Director offered me an internal promotion that I couldn't refuse: Marketing & Leisure Events in Toronto. 




I moved to Toronto that Summer! I was so thrilled and on top of the world. I moved in with family right downtown Toronto. Jack (Layton) to be exact. It was such a blast! I loved every single aspect of my job and of Toronto! As I traveled throughout Ontario I started working with many different media sources, I really learned the power of social media… In fact I advocated for VIA Rail to start their very first Instagram platform. I created the first post! I was loving what I was doing and really reinforcing passion for marketing, event planning and management! I hosted my first big event on board the train, it was a poker stars event. My love for poker commenced here! 


Over the next couple of years, I would jump on board the train to come back home to Montreal for the weekend and for my Monday classes at Concordia then would head back to Toronto for the rest of my work week. 


The next year, we found out that Jack was sick. It hit me hard. He is my role model to this day. I made him an all nature body butter to use!! He loved it and joked that I could start a company with it. There was a need for natural products in Toronto. I created my first body butter that he brought with him to a Toronto event that day. That evening, he came home and announced that I needed to produce 4 more butters. Four of his friends wanted a body butter too!





































Fast forward, my evenings turned into producing and shipping orders. My days blended to nights that blended to early morning filled with pumpkin spice lattes. I would literally come home from work at 7 PM and go to bed at 2 AM. It was crazy exciting but I also realized that I needed to make some big decisions. I couldn't even take classes that semester. There was no time. It was all work, work.... work! I was starting to burn out.


That September evening I decided that I was ready for business ownership. I had proven that I could make ends meet with my current orders and decided that my path was about to change. I worked hard and put together a business plan. 72 pages to be exact. I made the decision. I would leave Via Rail and pursue Sugar & Spice full-time! How scary! How exciting! I moved back to Montreal, the West-Island. And with that, in 2013, Samantha w/Love was born!










It was magical! It was the busy holiday season. I signed up for local craft fairs, met with shops and made amazing sales! Then came January. No sales. I was freaking out. It wasn't supposed to happen like this! Time to take out my business plan. Amongst the many pages of planning, was a marketing plan. As I started looking into marketing outlets in Montreal, I realized that this is my expertise. marketing and social media were my thing! No one knew this better than me! It was at that moment that I realized that I needed to create some sort of community page to find local customers. I started flocking through West Island Facebook pages to see what was out there. There were a ton of groups but in fact, there were no pages. Why not create a West Island Facebook page, create relationships, build my customers, and then shut it down once it serves it's purpose?


What's Up West-Island was born in 2014. I started gaining followers. First 10, then 100, then I remember my 1000 like (We now have an organic reach of about 250,000 a week - and are the largest Community Blog!!). As the likes increased I started promoting my body products within it. There was a request from other business owners to create a spring craft show. It was then that I created my first event - I had been doing event planning at VIA for the last couple of years - it was fitting. It went extremely well. The business owners that I met asked if I could post their businesses on my new Facebook page. What happens next is sort of a blur. What's Up sort of a snowballed. People started messaging me asking about everything local, my opinion on other start up businesses and even restaurants. I had so much fun responding. I then realized that I was now the "go-to" for everything in my community! WHOA!








Hello Corporate World

Goodbye Montreal - Hello Toronto!!

Company # 1: Samantha with Love

Unexpected Company # 2: What's Up West-Island

Some of my Products... Candles & Whipped Body Butters

Follow Samantha with Love here

Follow What's Up West-Island here

Getting Sick & Lessons

What's Up World Formed these Babies (many more to come!)

The 2014 & 2015 years sort of all merged together! I was running two companies completely full time. I went through all of the learning curves that there were for start up business in the retail and in the service industry! Trying to learn how to run both types of industries as a start up was definitely a challenge! I was pulling 20 hour days. A few months in I had to hire my first employee. Three months later, I hired two more, six months later I had six employees working under me. It was awesome but truthfully I felt as though I was just batting the balls back. I had become like a robot. I wasn't enjoying life. I was absorbing stress and even though I was doing what I loved I wasn't exactly happy. 


That year, due to excessive stress, I was diagnosed with an autoimmune disorder that I've been struggling with ever since! I had to step back a tad and realize that if my foundation wasn't solid my companies couldn't be. That year, I also started struggling with bullying for the first time in my life. It was horrible. I learned that sometimes success didn't always come with all things pretty. Much more on all of this in my blogs and on my channel, but these were the toughest two years of my life.  That being said, I learned what not to do as a business owner! I ended some toxic relationship and sort of reset my mindset. Positivity and happiness were what I needed and what my teams needed. There was no more room for anything else!!




On New Year's Eve of 2016 I remember everything. I was reminiscing on the past two or so of years of being self-employed and realized that this was real. That this was really happening. That I was really my own boss, was making my own rules, and was even supporting other employees! I was also making real money. What fun! What a dream! I really never expected this and was so proud of myself for getting to this level. 


I was working with many different people, business owners and employees. At the beginning of that year I was being approached by many of the West Island business owners for help on structuring, marketing and coaching. It was this year that I started what became my third company.


Due to demand, my sister Tracey and myself started a digital strategy company that just took off. Tracey is the smartest cookie I know. She graduated top atMcGill University with a knowledge management Masters - she earned a ton of awards, to say the least   She works with the top companies in the world, including NATO and the UN. She and I formed a solid duo. I started taking on start up, medium sized and some pretty big brands with her. Over the next year we did a lot of behind the scenes for them all. It was such fun until I realized that I couldn't sustain these three companies on my own. I was drowning again and my other companies weren't getting the love that they deserved.




At the beginning of this year (2017) I had to sit back and

really reevaluate what was making me happy. To be honest,

going in to help other businesses was fun while it lasted but I

needed more. I was sort of getting tired of repeating the same

information over and over again. There must be a better way of

inspiring everyone at once. That's when it happened. I was

approached by a large publishing company from Toronto.

This became a new pivotal moment for me.


I was asked to start blogging. I was asked to create a personal

brand so that they could highlight a Montreal entrepreneurs

lifestyle. What an exciting opportunity! This made sense. This

way I could communicate a strategy or a thought once

and many could benefit! Awesome! That being said, I didn't

have a personal brand or blog or anything to really work from. 

Everything that I was highlighting was being conveyed through

What's Up West-Island or past clients brands.I had been

working so hard on building the behind the scenes  of my

clients platforms over that past year or so that I didn't have anything to show for myself. I guess it was time to start my personal brand. WHOA! Where to start? I decided to start writing my own personal thoughts and reviews on my personal Facebook going forward as well! I got really great responses and the fun requests started rolling in.


I was receiving awesome West-Island requests and started highlighting products, was being invited to awesome events, travel and stay at local hotels, snap pics in cute hoodies, eat pretty much everywhere.. it was so fun! I was writing about these things. Ok, I guess this was blogging? Ok, cool. This was fun, but I wanted a bit more. It felt a little superficial. That week I wrote a real post. I wrote something from the heart. This is when things took a turn. How fun!! I LOVED it! I loved being myself, I loved writing about my personal experiences, struggles, raw life struggles. Real start up hurdles, mean girls... YES! This is what I wanted to d! 





I started a personal Instagram. The captions were real and from the heart. I made new friends and gained 1000 followers that first week. I loved it! I loved writing! I loved being able to be 100% open and honest and in creating connections with others who could relate! I started playing around with the Insta stories too. I realized that it was so much easier to connect with people that way - to build relationships and to meet other girl boss friends. I loved Insta! SOLD.

















As I continued writing and connecting with the influencers and new friends and started learning the ropes of photography and video I was presented with an opportunity that was life-changing. That May, I left North America first time in my life to go and blog/review for a brand new travel company targeting female entrepreneurs! I was brought out to Jamaica. This trip changed my life. 





JOZU was a surreal experience. I met so many incredible influencers and entrepreneurs from around the world and made lifelong friends. I also went through a lot of personal growth on this trip being extremely vulnerable and scared and heading out f my comfort zone with someone who was brand new in my life... to be discussed in my diaries and on my channel another day. I had never been outside of Canada or the USA and it literally changed my perception of the world. My adventures were just incredible. I can't wait to be discussed in my diaries.





As I prepared to come back home to

Canada, I was approached by a new

friend that I had made there with such

an exciting idea. He wanted to bring my

What's Up business model out there.

He was already a part of the tourism world

in Jamaica and wanted to incorporate

what I had created in Montreal out there.

He saw something that I hadn't. Oh my

God! We were going to start a new

community in another Country!! What's

Up Jamaica!


As I settled back in at home to tackle this new plan, I opened up my inbox and had a message from one of my current What's Up Managers. She wanted to start her own Community page in her neck of the woods.... WHOA! What a coincidence. It was then that I made the decision: Why not start communities all over the world - real and raw people running them and helping the communities connect? This is how the vision for taking over the world, one community out of time commenced. Spring 2018, this started coming to fruition.





What's Up World was officially created to umbrella my new endeavour ...

that month: What's Up Glengarry was formed! In August came What's

Up NDG. September was used to focus on Jamaica - which will be 

launched on January 1st. My goal is to create a new What's Up every

single month with the most incredible leaders! Right now we are 

recruiting the following managers to run: Toronto, Ottawa, Cornwall

& Townships! What FUN!!


2016 & Company #3


My Sister Tracey & BFF

Autumn 2017

My Instagram

Leaving Canada & USA for the First Time

What's Up World?!

Jamaica. Enough said.

New Communities

Present Day

Fast forward to now. October 2018. My day-to-day is a little bit crazy but I'm having the time of my life. I've actually just launched a podcast with my friend and have started writing a book! I used to focus on the destination and would never feel happy at the end of the day because I wasn't yet at that "top goal" which realistically takes time. Rome wasn't created in a day, right? I've come to realize that, with me and with any leader in any industry, the main "goal" will never be achieved as us girl bosses continuously strive for more and for better.


So... step back, toast to everything that you've achieved thus far and ENJOY THE JOURNEY! Life is about the experiences. Yes I'm an entrepreneur and proud to be considered a local influencer but above all I am just following my heart and doing what I love doing best. It's pretty neat that one can turn their passion into their career. I'm super proud that I've been able to establish this. I'm also super fortunate to be meeting others who have done the same and realizing that the world is our oyster. Trust me though, if I was able to do all of this... any else can! On that note...


... before I conclude, I'd like to interrupt. This may be the most important part of my story. The one that I want you to know about. I just finished proofreading the above. Yes, I am super happy with my path so far and the success of my teams, clients and of myself but I also need to bring one more thing to fruition and into the light. I am human. I've made mistakes, I've taken on too much, I've overpromised and under delivered. Not because I didn't want to... but because the world of entrepreneurship was a new one for me. There's a reason why it takes years to get a degree and to become an "expert" in something. It takes times and practice and mistakes and learning... there are lots of learning curves in anything and everything and I went through the curves of 3 different types of businesses... ALL AT ONCE - Yikes!! I had to wear a ton of different hats - Management, Marketing  Finance, Legal, Admin, Owner, Employee... etc The good news: I finally feel as though I'm there now. I have arrived and have things are where they need to be. Phew!! I've struggled with health. I was diagnosed with 2 auto immune diseases... these were triggered by the unstoppable stress and 20 hour work days throughout the first year of self-employment. Don't try and take on 3 start-ups all at once = you can get sick. I went into a bit of a burnout but snapped back... with a different outlook! It's not all peachy... and instagram posts aren't always reality. 

I've also struggled with relationships and friendships. I've brought (and let)

the wrong people into my life and I've had to let go of people due

to a variety of different reasons... even a 10 year friendship. I've had people

come into my life just to try to leverage off of what I've built. It's not 

always easy to detect at first. I've had, actually HAVE, three girls who have

made it their mission to bully me excessively too - there was even a FB

feed allocated to how horrible of a person I am... trust me, waking up to

daily screenshots from my real friends highlighting the new messages 
about me on this feed wasn't exactly the peak of my day. Finally, I've

had to actually get a restraining order against a girl who was charged

with criminal harassment. She disliked me because I reminded her of the

"popular girl in high school" who wouldn't give her the time of day. Really?

Yes, really. The self employment realm isn't easy. Yes, you get judged when

you're out there for the public to see. This is the truth though and apart

of the journey. It happens to everyone.. and the more you climb the

success ladder, the more prepared you best be. 


Why am I telling you all of this? ... because this is apart of my story. I'm raw and real and wear my heart on my sleeve at times. It's apart of my lessons and apart of being an entrepreneur and a LEADER. There will be struggles, there will be drama, there will be days where you ask yourself if it's really worth it. It is. When you wake up every day with a spring in your step, looking forward to your "to do's" you will realize that YES, it is worth it. Life is fun and life is short and should be filled with people who support you and love you unconditionally. You should be choosing to do what you love every single minute of it with the people who lift you up.


... that being said. I am EXTREMELY excited to welcome you to my JOURNEY and to my GIRL BOSS world.To introduce you to my friends and to my favourite places, practices and more!! I can't wait to see what the future holds!

Most Importantly...

The Old Port of Montreal.

Samantha xoxo