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5 lessons from getting my business acquired by Arlene Dickinson.

Joanna Track shares her advice for fellow entrepreneurs at a fork in the road.

Joanna Track

By Joanna Track

One of the reasons I’m such an avid non-fiction reader is that not only do I learn something about the world and/or someone who lived in it, but I get the added thrill of knowing it really happened. People often say, “the truth is stranger than fiction,” but in this case, I can say it’s better.

Once upon a time (about nine months ago) there was an Average Jo, musing about life in my eponymous newsletter, when a message landed in my inbox from the one and only Arlene Dickinson. It said, “I really enjoy your blogs and news approach. I’m a fan.”

After looking up, down and all around to see if I was being Punk’d, I let out a very eloquent, “What in the actual f**k?!”

I played it cool for all of 17 seconds. I then expressed my gratitude for her kind words and encouragement. Little did I know it was the beginning of a fairy tale (dragons and all).

Like most entrepreneurs, and humans around the globe, 2020 had me on one hell of an emotional rollercoaster. With more downs than ups, it was enough for even a seasoned entrepreneur like myself to feel more than a little unsettled. Couple that with my then-impending 50th birthday and I was up to my eyeballs in an existential crisis. 

“Who am I?”

“Where am I?”

“What do I want to do with my life?”

“WTF?!?!?!”

And other deep questions filled my mind.

Then, December came. It was cold, dark and gloomy. We were back in lockdown. Many of our clients who had crawled out of the woodwork in the fall went back into hibernation. My energy, motivation and bank account were dwindling. I was tired — mentally, physically, emotionally. 

And then, “Ping!” My entrepreneurial inspo slid into my DMs: “How’s biz?”

“Funny you should ask…,” I thought. But in that moment, I had a choice. I could put on a brave face and pretend I was fine. Or I could be vulnerable. Open up and speak the truth, and maybe, just maybe, admit that I didn’t have all the answers.

I did just that.

I felt I was at a crossroads and needed to make some decisions about my future. I valued her opinion, so I asked if she would be open to a discussion in order to get her perspective. And she said YES!

I spent the next few days preparing. In order to ready myself for the meeting, I rewatched episodes of Dragons’ Den, watched interviews, read articles, and spoke to people who knew her. I documented my own story and figured out my asks. And let me be clear, I was not asking for money. A word of advice to anyone and everyone who ever gets a moment like this with someone they respect and admire — there are many things more valuable than money, like sound advice, perspective and encouragement. That was what I was after. 

In this particular fairy tale, I hit the treasure trove. It was an intense and insightful conversation that led to us discussing an alternate route: a prospective partnership and an opportunity that I could have never imagined.

And the rest is history… in the making. I see it as a reinvention — for me, for my brands, my team and for Arlene’s ecosystem of companies. It will not be without its ups and downs, its twists and turns. But like I said to her on the day of the announcement, “It’s like having a baby! Hard, but so worth it.”

Part of what attracted me to this merger was the opportunity to learn from someone I wholeheartedly admire. In the short time I’ve gotten to know Arlene, I’ve already reaped the benefits of seeing her as a leader, a negotiator, a mentor, and an entrepreneur. I see so much of myself in her. Not only who I am now, but who I want to be as I continue on this journey. And while this post is not intended to be a romance novel, I want to acknowledge and share my gratitude for her support, encouragement and belief in me. The next chapter will be incredible!

While I look forward to what’s ahead, I’ll never forget what I’ve learned along the way. I could go on for pages, but who’s got the time? I’ve got a boss now! (You’ll have to wait for the book.) In the meantime, here are a few thoughts that I hope may help you if you’re finding yourself at a fork in the road:

Keep on keeping on.

Not the most original phrase, but in this instance, it’s so important to remember. If you create a good product, habit, relationship, or whatever, keep investing in it. Consistency and integrity are key. For almost five years, my team has given blood, sweat and tears to ensure The Bullet arrived in your inbox every day with just the right amount of news and humour. It was the product that caught Arlene’s eye, not my devilish good looks. 

It’s more important to be kind than nice (but be nice when you can, too!).

Even though being an entrepreneur can be lonely at times, there is no success without an amazing team. I’m blessed to have the best in the business. They are the most dedicated, hard-working, passionate group of people and without them, I wouldn’t be where I am. (I’d also be a lunatic laughing to myself all the time.) I’ve always treated my relationships with great care. I can’t always tell them, or give them, what they want, but I’ve always been committed to kindness, transparency and opportunity. If there’s something in it for me, I make sure there’s something in it for them. I make myself open and available to them and expect the same in return. If not for those guiding principles, they would have jumped ship long ago. But I’m so glad they stayed for the ride.

You always have a choice (even if you don’t like the options).

In almost every instance, you are where you are based on your own choices. And you can stay where you are, or change where you are, depending on what YOU choose. You may not like the options, but there are always options. And every choice comes with pros and cons. You need to determine what you can live with and what (or who) you can’t live with. Doing nothing is also a choice but will most likely lead to nothing. Choose wisely.

Let yourself be vulnerable (sometimes).

I’m not implying that you should open up the kimono every single day (c’mon, you need to leave some things to the imagination), but you need to give a little to get a little (or a lot). You need to consider what’s the worst that can happen and then go in prepared for it. You might be pleasantly surprised. Or not. But you don’t know until you try.

Lady luck is just around the corner, you just need to look (and be prepared).

The saying goes, “Luck is when preparation meets opportunity.” I was prepared by delivering my product, looking at all my options, and putting myself out there. And I seized the opportunity of meeting with Arlene appropriately. I was prepared and humble and I made the best use of the precious time. 

Over the past few months, many people have said versions of the following, “It’s amazing how the universe works, how Arlene came just when you were hitting rock bottom,” blah, blah, blah. I’m not belittling talk of the “universe” or “signs,” but it got me thinking. I believe the universe is always sending us signs, but it’s when we’re feeling down that we’re more apt to look for them. We open our eyes (and ourselves) to new possibilities.

So, don’t wait for the universe to send you a sign, go look for it. I found mine: it’s a Dragon and she’s on fire.

Joanna Track is the founder and executive publisher of The Bullet, Canada's digital destination for your quick shot of daily news, and co-founder & chief strategist at content creation agency, Newsworthy Co. She is known for her prior entrepreneurial pursuits, Sweetspot.ca and eLUXE, two of Canada's most well known online destinations for women. This article first appeared in her blog, Your Average Jo, and has been reprinted with her permission.