Chapter 1

1. Getting Started

What Brought You to the Threshold of Becoming an Entrepreneur?

I suspect there are as many pathways to becoming an entrepreneur as there are entrepreneurs. Regardless of what brought you here today, your entrepreneurial journey has started, and you are on your way to achieving the success you have envisioned and deserve. My journey has been a unique process with lots of twists and turns that have taken me to the brink of despair one day and incredible heights the next. Glean as much as you can from my experiences to maximize the potential of your journey—and don’t forget to enjoy yourself!

My First Step

After two years of working in specialized recruiting, where I played matchmaker for clients and candidates, I’d been asked to help a multinational open its operations in Toronto, Canada. I was super excited, a little bit mystified, and completely unsure of what I was supposed to be doing. So there I was at twenty-five, a manager in charge of five employees with the responsibility to build a new division for a public company.

And my training? “All right, get after it.”

That didn’t seem to matter to my director. After his sparse words of encouragement, he smiled and walked away, leaving me at my desk with little clue of what to do and a whole lot of questions.

But, if my only marching orders were to get after it, then that was exactly what my team and I were going to do. I began by setting up a basic two-step strategy:

1. Sell, sell, sell.
2. Deliver excellence without exception.

It didn’t amount to much, but it spoke to our position as the new kid on the block. As a startup expanding into a new marketplace, we needed to be aggressive with our large-client acquisition right out of the gate. Further, if we were going to keep those clients and gain some traction, we needed to do things the right way.

Miraculously, our two-point plan worked. Soon, our Toronto office was the most successful in the company, even competing head-to-head with both the New York and LA markets. For the next two years, we enjoyed nonstop growth.

As our startup grew, so did my responsibilities and skills. First, the company began flying me out to California to sit on one of its committees. Then, before I knew it, I was being introduced not only to the various members of the C-Suite, but also to the chairman of the board.

That’s when they dropped the bombshell. “We want to offer you a new position,” they said. “We still need to write the job description, but once we do, we’ll send that along with our formal offer.”

It arrived the next week, and it was certainly generous. Not only would I be making tons more money—a $60,000 boost to my base salary, plus a huge variable component—I would also get to travel to our other branches to help them get established in new markets.

My jaw hit the floor. A huge pay bump and the chance to rack up those airline miles? To my twenty-seven-year-old mind, it all sounded too good to be true. As it turned out, I was right.

Second Thoughts

As excited as I was by the opportunity, my gut was telling me something wasn’t right. The feeling began when they asked me to sign the offer, then and there, which struck me as odd. I stalled, asking if I could take the night to go home and think about it. The entire ride home, I kept asking myself over and over: do I want this?

Every fibre of my being screamed no, yet I didn’t understand why.

My husband didn’t understand either. Newly married, we were young, ambitious, and ready to build our careers and start a family. To him, the opportunity was a slam dunk. “The pay boost alone is reason to go for it,” he said. “Why would you turn it down? Because of the travel?”

It wasn’t the travel—at least, not directly. The truth was, while I enjoyed my success at the company over the past couple of years, I wasn’t exactly thrilled with the company itself. I enjoyed recruiting, but I didn’t believe in my company’s approach, which was formula-driven. It was a numbers game. My team and I were expected to make an outrageous number of cold calls each week and interview as many people as we could.

This unrealistic workload told me my company didn’t care much about its employees, nor did it care about delivering the best results for its clients. All it cared about was its bottom line—which was quite healthy—and it pit salespeople against each other to reach it. This, of course, led to remarkably high turnover. So many people were coming and going that they had to change the key code to get into the office each week!

I had succeeded there, but I had no illusions about the kind of company I worked for, but now that I had a chance to rise up the ranks, it was a time of reckoning.

If I didn’t believe in our company and its process, how could I travel around the United States and preach it to others? Besides, promotion or not, did I really have any job security in that kind of environment?

But there was more to the story—though it took me years to understand or admit it.

Afraid to Speak Up

During my time at the company, I was often the only woman at the table and surrounded by a ton of men. This in itself wasn’t a problem, as I have no problem hanging out with the right group of guys, but the men at the table were not them. Being the only woman in the room at a company with a toxic culture and an outdated view of women is something entirely different. Some of my male colleagues simply didn’t know how to make room for a woman’s voice at the conference table.

I was often afraid to speak up—and when I did, my voice would literally become a liability. I have a young-sounding voice. It’s no big deal to me, but especially when I was younger, every time I would speak up in meetings, one of two things would happen: one of the men in the room would say, “Oh, listen to her cute voice. Mandy, you’re so cute.” Or, I’d start to speak, and then someone else would talk over me, rolling up my suggestion into his, as if he were the one who had thought of it all along.

In both cases, their behaviour was unprofessional and insulting.

I’d like to say that was the worst of my treatment, but sadly that’s not the case. There were many instances when leadership and coworkers would cross the line, saying wildly inappropriate things, making passes, and even groping me.

I’m not naïve. I knew that behaviour like this from anyone was inappropriate. But, like many women then and now, especially young professionals, I didn’t have the confidence to say anything. I never reported any of this behaviour because I thought no one would believe me. Even now, reporting sexual harassment can put a woman at risk of losing her job. In the early 2000s, it was all but guaranteed.

If I had reported what I’d experienced, I would almost certainly have been accused of lying or seeking attention, and I didn’t want to be fired for someone else’s inappropriate behaviour.

Instead, I did what many young women do in similar situations: I locked the experiences away in a box and didn’t think much about them for years. Only my sister knew what had happened. Of course, denying these experiences doesn’t make them go away. That growing pit in my stomach wasn’t just about taking a promotion with a company I didn’t truly believe in. It was also the dread of knowing that if I took the job, I would be subjecting myself to similar treatment for years to come. I wouldn’t fully understand this feeling until several years later, but it was there just the same, and I knew I couldn’t ignore it.

The next day, after a long night of soul-searching, I signed the contract—and then walked over to the nearest paper shredder and destroyed it.

These days, when I hear stories of women coming forward decades later with their own stories of harassment, I understand. When you’re a young woman, and all you’re trying to do is make your way, it can be hard to understand what has happened to you, and even harder to say anything about it.

On My Own—And Loving It

The moment I shredded that contract, I knew that my time with the company was over. It was time for me to set out on my own. But before I told them as much, I needed to lay the groundwork for my next steps. So, I took a half-day, headed off to the bank, and asked for a line of credit.

I’d been doing well the past few years, but my husband and I had just spent all our money on our wedding. We had no savings and no assets to leverage for a small business loan.

Instead, I just said we were planning to upgrade our furniture and needed a little help. The second the bank approved me for an $8,000 line of credit, I walked into my...