Just Go With It: How to Navigate the Ups and Downs of Entrepreneurship

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Copyright © 2020 Mandy Gilbert

All rights reserved.

ISBN: 978-1-5445-1432-1

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To my incredible sons, Isaac and Sam

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Contents

Introduction

1. Getting Started

2. Building the Foundation

3. From Entrepreneur to…Parentrepreneur

4. Making It Work

5. Crash Goes the Economy

6. Invest in Yourself, Invest in Your Business

7. The Idea Machine Is Out of Control

8. Resetting the Culture

9. New Values, New Identity

10. Partnerships, Investment, and New Horizons

Conclusion

Acknowledgments

About the Author

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Introduction

Where Will Your Entrepreneurial Journey Take You?

This book shares my journey as an entrepreneur from the early days of my first business, Creative Niche, to the founding of an international design and tech school, and everything in between. Woven throughout my story are all the real-world, hard-earned lessons I discovered along the way. These are the lessons we entrepreneurs don’t know we need to know when we’re first getting started, and the ones we don’t like to share with others when we learn them (because they’re just too painful!). And, of course, they are the ones we often don’t recognize or even expect to appear, until it’s too late.

All entrepreneurial journeys have similarities, but in the end, they are all different from any other, and mine is no exception. I started my business with an $8,000 personal bank loan and a blurred blueprint for success. I wasn’t a computer science wunderkind that raised a ton of capital, accompanied by a trusted board of advisors and investors to help guide me every step of the way.

I bootstrapped my business from the ground up, and I wrote this book to share my experience with entrepreneurs who have a vision, limited resources, and a pile of energy. This book is for all those small-to-medium sized entrepreneurial companies that aren’t making headlines but are driving economic development through job creation.

It’s for the entrepreneur who started a strategic HR consulting company and wants to get out of day-to-day execution and scale their business. For the one who quit their safe office job to pursue their dream of making the best biscotti there is to buy. The one who is taking over a family business and is feeling stuck on how to turn it around. And it’s for the 100,000 entrepreneurs in Canada and the 1.5 million in the United States, who start new businesses every year. It is for YOU.

Know in advance that while my experience may help you along the way, I don’t have all the answers. Some lessons you’ll have to learn yourself, and sometimes more than once. Just like there is no playbook in life, there isn’t one for business either. It’s your job to learn how to manage both, how to be accountable, and how to lead in good times and bad. Figuring things out on your own takes courage and tenacity—but don’t worry, luckily that’s what entrepreneurs do best!

None of this is going to be easy. Entrepreneurship demands that we take enormous risks, put ourselves out there, and be vulnerable every day, no matter what the outcome is or how we’re feeling. But also, it will be the most incredibly rewarding experience of your life.

We’re about ready to get started, but before we do, I just have one question for you:

How do you spend your time when you’re at work?

It’s okay if you aren’t proud of your answers, and it’s also okay if you aren’t sure how you should be spending your time. That’s why you’re here.

Just know that as your business changes, so must you, along with the role you play within it. In order to remain effective as an entrepreneur, it’s important to always look for new ways to keep your business moving forward—and to keep searching for the most effective use of your time.

The path might not always be linear. In fact, there will be times when it feels like you’re constantly backtracking just to keep your business afloat. Other times, it might feel like you’re stuck, unable to make any progress at all.

Whenever that happens, here’s my best advice and the approach that has kept me sane and successful after all these years: Just go with it.

As long as you are committed to your success, willing to rely on others, and ready to learn, the path forward will eventually present itself.

It Starts with You

During coaching sessions and speaking engagements, I ask the entrepreneurs I am working with or speaking to the same question I asked you: How do you spend your time when you’re at work?

Often, the answers are pretty vague, something along the lines of, I’m not sure, I don’t know, just a lot of stuff, I guess, mostly planning.

If you cringed a little reading the above, then you’re probably thinking the same thing I do every time I hear it: That entrepreneur has no idea what they’re doing!

Of course, whether we like to admit it or not, that’s the reality for many of us—especially in the early going. We get an idea we’re convinced could change the world, we set up a business to make that idea a reality, enjoy some early success, and then we stall out.

There are plenty of perfectly reasonable explanations for this. After all, entrepreneurs have a particular personality. We’re easily excited and easily spurred to action. When we get a good idea, we tend to leap before we look. That is, we’re usually already in the thick of things before we’ve fully thought out our plan—and then before the dust settles and we have time to regroup, we’re off chasing down some other crazy idea.

This mad-scientist-like energy is what makes us so wonderful. But when left unchecked, it’s also what makes us frustrating to the rest of our team, especially after we’ve grown our business and we have employees to look after.

It can be hard for us to admit it sometimes, but many entrepreneurs don’t know the value we’re supposed to be providing to our companies. We don’t know what our own job is—and therefore, we don’t know how to effectively lead, manage, and grow a company.

But here’s the good news: that same mad-scientist energy that got you this far can be harnessed. As an entrepreneur, you already have all the qualities you need to become a dynamic, effective leader. All you need is a nudge in the right direction.

There are very few easy wins in business. The line between struggling and thriving, between success and failure, is often razor-thin. Having a good idea, then, isn’t enough.

The entrepreneurs who succeed are the ones out there on the front lines every day, looking for ways to move the needle for their business. They’re taking care of their teams and initiating strategic projects that will benefit their organization, making everyone more successful and more efficient.

Entrepreneurs like this have one thing in common. They know the business they create is the result of the precedent they set.

If you’re content simply to survive, to pay the bills and live a semicomfortable life, then that’s the business you will create. However, if you’re dead-set on thriving, if you lie awake at night wondering how you can grow your business into something meaningful, then that will be the business you create.

Now, tell me, which business would you prefer?

If you picked up this book, then no doubt you want the latter. Once upon a time, when I was an eager twenty-something looking to break out of my nine-to-five and chart my own path, that’s what I wanted, too. And over the next decade-and-a-half, I fought tooth and nail to make that dream a reality. Today, three businesses and a lot of investments later, I’m proud to say I’ve made it.

My path to success wasn’t easy. Like many entrepreneurs, I was full of ambition but low on practical experience when I first set out on my own. All I knew was that I had a vision for something different and a passion to make it happen. As the years unfolded, I got a lot of things right and a lot of things wrong, but either way, I emerged a little wiser for the experience. Of all the lessons I’ve learned, perhaps the biggest one is that you can’t go it alone.

Being a leader means showing your team you have their backs, that you’re always going to be on the front lines fighting for them, and you’re working hard to lift them up alongside you so that you can celebrate the wins (and, yes, commiserate the losses) together.

However, being a leader also means knowing when to ask for help. It means identifying what you’re best at and then finding the most talented people on your team to do the rest. It also means trusting your team to be your filter when you’re firing off too many wild ideas, and it makes taking their feedback seriously, although, at times, it may be painful. Most importantly, it means being proactive about how you spend your time—and making sure you are always adding the most value possible to your business.

In terms of my experiences contained within these pages, I have endeavoured to fully disclose situations as they occurred with no sugarcoating. Likewise, this book isn’t a how-to manual, although it offers a lot of suggestions. Rather, it is my entrepreneurial biography and is filled with many of the events that led me to where I am now.

It has been an incredible developmental journey with significant emotional experiences, and trust me, it