Not your fairytale ending, but a damn good chapter

How I grew, lost, learned and made a bold move working with my sister to help pivot her business during the pandemic

In 2020, in the middle of the pandemic, I made the leap into the wonderful, maddening world of small business. Looking back, it wasn’t exactly my most rational move, but, I mean, who was doing anything rational at the time? We were all just juggling families, emotionally frail employees, working from home with our partners and making sourdough starter “for fun”. It was a crazy time, so leaving my very secure job as a CMO and embarking on a small business adventure with my sister felt like the least crazy thing. It was a chance to do something awesome with my best friend and carry on the legacy our Dad had built in the food service space.?

A lot of people said “are you sure it’s a good call working with family?” “Are you sure you want to leave your steady pay cheque to work in the food business, during a pandemic?”. The answer to both those questions is still YES. As heartbroken as I felt last year, I don’t regret taking the leap into entrepreneurship and I am incredibly proud of what we accomplished in a short time, against some very intense headwinds.?

This is not an opportunity for the naysayers to say I told you so. This is not that kind of story. This is about how humans deal with adversity and, frankly, trauma in different ways. This is about how much I underestimated the deep connection my sister would feel to the successful business she had built before the pandemic and how hard it would be for her to embrace the changes needed for the business to grow in a post pandemic world. This is a story about how small business owners are not ok and a reminder that many of them are only now feeling the true loss of “what was” and the emotional toll of 1 million pivots.

The beginning of a beautiful partnership?

For 2+ years, my sister and I worked harmoniously towards pivoting the business, expanding to new communities and rebuilding the business’ foundation to enable renewed growth. We did a lot in a very short period of time, all amidst lock downs and a thousand other challenges. After I left Plenty, I felt an immense sense of failure and went through a period of self doubt. To work through those feelings I spent time reflecting on the good stuff, something that I didn’t really pause to do while I was in it. So, bear with me as I first share the wins and the accomplishments. A few milestones we hit:

• Opened a pop up to test and validate an evolved concept; negotiated a temporary lease and served the Danforth community for 9 months…in the middle of the pandemic
• Opened two new locations under the “market and cafe” concept in communities outside the downtown core
• Built meaningful partnerships with local vendors and launched the Local Pantry featuring small batch, high quality brands from across Canada
• Relocated our PATH location to the bustling Commerce Court West
• Overhauled our delivery and catering systems to provide convenience without compromising quality
• Hired an entirely new front of house team and put strong leadership and HR systems in place
• Built operations systems and oversight for our kitchen to better serve as a commissary to our multiple locations and catering business
• Grew our brand with new branding, packaging, websites, PR, advertising and social growth

Personally, I proved to myself that I could do way more than marketing and I really thrived in an operations leadership role where I had the immense joy of bringing a big vision to life. For my sister, I loved seeing her regain her confidence and embrace her natural leadership and creative strengths. It was wild, messy and all consuming, but our distinct skills came together really well to create something new without losing the essence of what Plenty had become over its first 9 years of life. Our customers responded positively to our shared passion and energy and I really felt like this was something I could do forever, with my sister. Of course there were growing pains and really hard moments, but, for the most part, we were on the same page about what was right for the business, often finishing each other’s sentences in business meetings. It sounds hokey but it was like our Dad was there cheering us on and that made the hole he had left a little more bearable.

High tides don’t rise all ships

The TSN turning point in our partnership came a couple of months after our PATH re-location. At this point, we had now opened 3 new locations in the span of less than 2 years. So, we were both exhausted and just running on adrenaline. But, with a bit of breathing room my response was to say “ok now we need to re-focus on our foundation and drive revenue” and I started to try to execute on a plan around that.?Turns out, with a little room to breathe, my sister had a very different reaction. She started to doubt the business and, understandably, let the emotional exhaustion of the past couple of years just wash over her. In 2020, like many other business owners, she had been faced with fight or flight as her only two options and, with my encouragement, she had chosen to fight. But, in hindsight, how sustainable could that have been? At the time I could see she was struggling, but I stubbornly thought dammit, this is where the hard work needs to start and I’m just going to be the tide that carries us both. I regret not taking a bigger pause to get to the bottom of what was causing so much doubt on my sister’s part. At the time, I let my concern for the business cloud what my sister was experiencing and I tried in earnest to forge ahead.

Let this be a reminder for anyone who is coming off some big wins to check in with the entire team, reset goals, re-define scope, re-visit roles and responsibilities…but mostly create a safe space where you can express fear or doubt even if others are popping bottles.

You don’t know what you’ve got ‘til it's gone

I will be forever proud of what we built together, but looking back, I do worry that one of the things I was most proud of might have set in motion a chain of events that would ultimately lead to my exit. Of all of our shared accomplishments, I’m most proud of having helped pull my sister out of her pandemic funk and loss of zest for the business. After seeing her business disappear (curse you lockdowns) overnight she had gone from being an exceptionally passionate and optimistic business owner to essentially deflated. Joining as her business partner and working together on an evolved version of Plenty put some pep back in her step. I helped give her back her purpose and brought some fun back into it all. I gave her a partnership in the truest sense of the word.?

What I didn’t understand then, was that in her heart of hearts she may not have wanted a partner or at least the realities of what came with it. Plenty had always been her baby and having a partner would ultimately mean sharing ownership and growth, which really isn’t for everyone. But, the pandemic being the crazy time that it was, may have gotten in the way of her acknowledging that truth and she likely (ok, definitely) got caught up in my excitement to create something meaningful together.?

So when things started to go sideways I would eventually pull this hard truth out of her. It wasn’t so much that she didn’t want me there, running the business alongside her. It was that, when the insanity of the pandemic caught up to her and she felt the financial burden of it all, her instinctual reaction was to want to take back 100% control of the business. This was her safe spot. It wasn’t about me at all, it was about what would make her feel confident when everything felt so unfamiliar. While we had both agreed upon the vision and the new location offering, she looked around and thought “this isn’t my business anymore”. She wanted to go back to what the business used to be. To a simpler, more familiar time…as a solo small business owner. These were really hard truths to hear after two years into our partnership and I honestly felt blindsided. So what did I miss?

What would Marty McFly do?

If I had a flux capacitor could I have changed this outcome? Could I have had a more honest, detailed conversation about the realities of partnership and what that would look like beyond 6 months, 1 year, 5 years? Could I have somehow planned for the emotional variables that would impact the business? Would I have still joined the business? Given the circumstances, I honestly don’t know that we could or would have done things differently. As many of you know, not everyone is meant or built to make the shift from solopreneur to partnership and a lot of times the business owner won’t know if they can make the shift until they are living it. Plus, in our situation, the decision to partner was emotionally loaded so I’ve allowed myself some compassion for missing the warning signs if they were there. Regardless, as part of my period of self reflection I’ve spent time looking back to see what I missed and what I could have done differently (ah the joys of personal growth). Here are a few things I still believe we did well to set us up, along with a few lessons learned and one big “shoulda, coulda, woulda”.?

What I believe we did well:

• We had a clear, shared vision and plan to achieve it. Before I officially joined the team we spent a lot of time together getting Melissa’s vision for the business down on paper; where she would like to grow the business to if she had all the resources available and then we boiled that down into a realistic, competitive, achievable plan. You know, your typical strategy work. For two years, we used this vision to guide the business direction and choices we would make and it generally worked in the sense that we were on track to achieve the vision.
• We started with clear roles and responsibilities. When we started working together Melissa was ready to lean into a CEO role as long as it was built around the things she loved most about the business; interacting with customers, experimenting with food and spending time in the stores. Ok so the face of the business, the brand, the product, the store design and customer experience. I was tasked with rebuilding the foundation of the business to set us up for real, sustainable growth. Ok so the backend of the business; store operations, HR, inventory, sales, accounting and marketing. Essentially all of the things that Melissa didn’t want to own but that I was well positioned to lead. I still believe that these roles were perfectly suited to our respective skills and the business’ needs and I stand by that.?
• We had weekly and quarterly goal setting and prioritization meetings. This was a very foreign concept to my sister, but with such a lofty vision, I felt this was something the business really needed to enable rapid growth and keep us focussed on our priorities. I believe that for the period we used this system it really allowed us to stay focussed and make a massive impact in a short period of time.
• Melissa chose to bootstrap and supplement with low interest loans which provided us with the flexibility and freedom to move quickly and creatively. When we looked at various funding models to fuel our expansion, Melissa had always had success self funding and really loved the control this provided. So, we proceeded with this model, fuelling rapid growth while retaining 100% ownership of the business.

What I believe I could have done better (or not at all):

• I took the shared part of our vision for granted. I assumed that since it was on paper and we were executing on the plan, we would continue to be on the same page. I think in our haste to open locations and solidify our new market position, I didn’t think to stop and really check in with my sister. She didn’t give me a reason to, but I could have created opportunities for more space to check in on our vision and strategic plan.?
• We didn’t do a great job sticking to our roles and responsibilities. We slipped into each other’s lanes as we opened our second, then third location. I was very naive when I joined and thought this would be easily avoidable with clear role definition, but, unless you’ve lived it, you can’t appreciate the wild west nature of food service operations. After we opened the PATH, I recognized that we needed a real reset, but by then our roles had been murky for a while and now I know that this contributed to Melissa’s lack of comfort even if she couldn’t pin point it at the time.?
• I let the goal setting and prioritization meetings slide. While I tried to take a less formal approach, the notion of prioritization was quite foreign to Melissa and I believe this structure ultimately created more stress for her. So, counter to my better judgment, I let these meetings slip by the wayside and we went with more informal daily checkpoints. Now in this area, I do think I should have stuck to my guns and helped her with building her prioritization and strategy muscles - maybe we would have uncovered some of the hard truths earlier and worked through those together.?
• After opening 3 locations in 2 years, the business was highly leveraged, more so than it had ever been pre pandemic. Historically, Melissa had opened one location every two to three years, making it easier to have an expedited debt repayment plan in place. We still had a plan in place, but the emotional burden of carrying debt took a huge toll on my sister's ability to remain optimistic about growth plans. Again, I underestimated how much she would compare our post pandemic business with her pre pandemic business model. With my steadfast belief in her and the business, I should have fought for alternative funding models where the burden wouldn't sit squarely on her shoulders.

As I reflect back and try to boil this all down, I think my exit can really be attributed to two important factors that are sort of woven through the above points.?

1. The unforeseen emotional toll of going from solopreneur to partnership, exacerbated by the pandemic. I think there are a lot of things we did that, in theory, should have helped us avoid the pitfalls of a partnership. But, reality is very different from theory with all its nuances, emotions, perspectives, pandemic lockdowns and the added complexities (and generally sh*t storms) of running a food business. So my corporate toolkit, past experience working with founders and that shiny business degree were somewhat helpful, but I definitely underestimated how the emotional toll of the pandemic would impact our partnership and Melissa's vision for the business.
2. Our lack of an exit strategy for our partnership. What would we do if things went sideways? If one of us no longer wanted to achieve the vision we had mapped out? If communication completely broke down and we happened upon a black swan event; in this case, one partner experiencing something intensely emotional they couldn’t articulate. If I had been working with anyone other than my sister, my business school and real world training would have forced me to plan for conflict and a potential breakdown in the partnership. But, because she is my sister, I really couldn’t fathom we’d experience this type of breakdown in our communication and partnership. Which brings me to my next point…

Turns out working with family IS hard, but not how the naysayers might think

Ok so once Melissa admitted she didn’t want a partnership and wanted to pump the brakes on growth indefinitely, I felt I had to navigate the situation very differently than if this were just a business partner. If it had been a business partner I would have gone back to the commitment we had made to each other and to the vision we had been working tirelessly towards. I would have said “we are a partnership, we need to figure out a path forward that is best for the business.” Then we would have revisited the vision, along with the strategic plan and re-focussed. I actually tried that. I tried a lot of things, but nothing worked. I won’t get into the details here, and I know y’all are going to have a lot of opinions, but just know that I don’t think there is anything I could have proposed at the time that would have broken through my sister's fog of concern and unease.

My sister is an incredible, warm, kind and compassionate person who tends to put everyone else’s needs ahead of her own. She practically raised me and was essentially my caregiver for my formative years. So, believe me when I say this was no Waystar Ryco type of scenario. This was my sister going through something that she couldn’t explain to me for the first time in our lives. But, when I say working with family is hard, it’s because, if you know our relationship, I really had no choice but to put her feelings ahead of the business and remove myself from the equation. I was concerned for the future of the business we built on the back of our distinct skill sets, but I ultimately had to respect that we didn’t want the same things anymore and that, as agreed upon, she would maintain veto power as the primary business owner. So, working with family in this instance, was hard because my love for her and concern for her well being led me to make choices that would put her needs ahead of the business and ultimately my own.?

Today she is back to running the business on her own and while she isn't totally clear on the future of the business and she says she misses working with me, I think she is back to a place of harmony where she gets to lead the whole shebang. I believe she will be happiest keeping the business status quo for now and enjoying the beautiful chaos of it all. And, since we all get so caught up in the growth game, she still owns 4 locations and a catering business - that's a big deal team and it's more than enough for her to be happy and fulfilled!

Long story short, the outcome wasn’t what I wanted but I’m happy I went for it

As for me, I was pretty shell shocked after leaving. My first response was to want to jump right back into something new. However, I was experiencing some serious imposter syndrome that left me feeling pretty stuck and not up to the challenge of another entrepreneurial endeavour. I felt Plenty had been my one big chance to show the world that I was capable of entrepreneurship and I really felt like I had failed at it. I don’t think any of you would think that looking at everything my sister and I accomplished over two years but that’s why they call it imposter syndrome. With some space, I’ve been able to feel good about it all and see it for what it was - a bold move and one that stretched me in ways I didn’t know I could stretch.

I recently spent some time reading the article I wrote when I first joined Plenty, about carrying on my Dad’s legacy and building a life guided by courage, optimism and no regrets. In my heart of hearts I think I did that here. I think I helped create something awesome despite many many barriers and I loved every minute of it. I think it was courageous to at least try. Now I know that I am at my core an entrepreneur and I am strong in that conviction.?

So will I do things differently next time? If you know me, I’ve always felt the need to work, to make an impact, to do. I was never great at just being in the moment and I always felt there had to be another goal to work towards. As a result, I’ve had some pretty challenging health issues (hint hint as to what’s next for me) and I generally ignored my body screaming at me to slow down. I told you this wouldn’t be a story about silver linings, but I am appreciative that I ultimately took some time to sit with some really uncomfortable feelings and stopped myself from running to the next opportunity. Well, first I wallowed. And then with some encouragement from my annoyingly wonderful husband, I did my best to embrace the temporary limbo. I did therapy (not my jam, but it did the trick), I spent some special time with my amazing daughter, I took up biking, I did some truly once in a lifetime family travel and just tried to be in the moment for a little while. Having the privilege of taking a few months to just be gave me space to move past my disappointment and see my own biases, blind spots and figure out what I’m really meant to be when I grow up. I certainly don’t have it all figured out, but I have clearer boundaries and balance in my life and I am 100% committed to hanging on to that, whatever comes next.

Thank you for reading, for your support and I hope you’ll continue (or start) to create space within this community for honest, hard conversations about failure, growth and change.