Ross Simmonds always had a hankering for business and loved the idea of working for himself, fulfilling his own passions, and answering to no one.  He got that wish when he decided that working for someone else’s dream wasn’t worth his time, knowing that he could do everything better.  If following your dream is on your goals list, Simmonds has some words for you!


How did you learn to be this business-savvy at a young age?

I’ve been a student of entrepreneurship since I was a kid. My grandfather ran his own paving company and I was obsessed with the idea that he didn’t have to answer to anyone (except Nanna). I learned a lot from watching how he operated his business and was lucky enough to be mentored by some amazing people from the time I was in high school.

For some reason, lots of people gave me a chance. And when I had those chances, I always made it an effort to take 100% of that opportunity and give it my all. If I could tell young people anything, it would be to always give 100% to any opportunity that comes your way. Especially if it’s a challenge. It might not seem like it’s worth it in the short term but you’ll either make a significant impact or learn more than you could ever imagine.

What made you sick of working a 9 to 5 job?

I’d say the lack of control.

I loved my last employer and loved everyone I worked with. For me, the challenge was simply the fact that I couldn’t control the destiny of the company and felt as if I didn’t have as much control over my own life. I had to work when someone else wanted me to work and I had to work on projects that someone else wanted me to work on.

As my own boss, I have more flexibility and the capacity to allocate my time and resources where I see fit. That’s the key for me. Being able to wake up in the morning and go to bed at night while doing whatever it is I want in between. That’s always been my definition of success.

It’s tough to balance a lot of different passions, and execute on each one well. How do you stay focused with two businesses?

It’s definitely tough but I think it comes down to discipline. I’ve worked in environments where distractions are encouraged and run from the top to the bottom. If you’re not laser focused in the moments in which you need to be producing work and delivering results – you’re never going to be able to compete with someone who has that focus.

I live and die my calendar. I block off time in my calendar for everything from email management, writing, client meetings, team check-ins, personal time,mentoring, you name it and it’s in my schedule.

For me, it’s all about prioritization and task management. I start every day with what I call my “Kill List”, the tasks and items I need to accomplish in the next 24 hours. From there, I knock items off starting with the hardest challenges and tasks. Next to each task, I write down a rough estimate around how much time it will take to complete it and hold myself accountable to shipping something within that time frame. If I don’t meet it, it means I’m going to be up later than I should and likely drinking a whole lot of coffee.


A lot of the Blavity audience are first time or  aspiring entrepreneurs. What advice would you give  them about starting their first business?

The first thing I’d suggest is figure out what the right idea is for you to be chasing. Take the time to get to know what you’re really good at from there and then understand what it is you offer that people would be willing to pay you for. This diagram is a great reminder in my opinion of how to figure out exactly what you need to be working on:

I have a copy of this on my wall in my home office as a reminder of what I’m doing every day. It’s one of the pieces of art we offer at Hustle & Grind and it’s a top seller because people understand the value of finding their purpose. You might not find the Purpose right away but if you can find a profession or vocation at this stage; you’re already two steps ahead.

My next piece of advice would be to embrace the hustle. And when I say hustle, I’m not talking about shady business or ripping someone off – I’m talking about working harder and smarter than the competition. I’m talking about having a willingness to put in the late nights when your friends are asking you to come hang out. I’m talking about putting yourself into uncomfortable situations because it will help your business grow.

It’s not enough to set up a landing page on SquareSpace and send a few tweets to call yourself an entrepreneur. You need to be out putting in the effort and time to create and deliver value to others. You need to be delivering value that results in an income. Too many wantrepreneurs view entrepreneurship as this glamourous endeavour – in reality, it’s filled with some very low lows and some very high highs… You have to be willing to get burned and be willing to hustle.

When and how did you decide to become an entrepreneur?

My first business was when I was in High School and I was selling doo-rags out of my locker at a 100% markup. Living in a small place like Nova Scotia, Canada, we didn’t exactly have lots of options for doo-rag colours. So I went out one day with my Mom and Sister and came across a shop that was selling all the colours of the rainbow for doo-rags. No one else knew of this place at the time so I seen it as an opportunity to bring them back to school and sell them at a premium price. So that’s exactly what I did.

What projects are you currently working on?

I’m currently working on three main projects. I’m running Foundation, which is my consulting business. I’m running Hustle & Grind with my co-founder Findlay, a subscription box service for wantrepreneurs and entrepreneurs looking to achieve success. And a new social media software that I’ll be rolling out in the coming months called Crate.

I’m also working on an eBook called the Hustle Manifesto; how to escape the 9 to 5 in six months or less. In this guide, I’m going to share the information and insights that I wish someone would have offered me when I was first starting out. I think anyone looking to achieve success will benefit from reading the insights and strategies found in this guide. I’m hopeful that my stories and the stories from others can inspire and more wantrepreneurs achieve their dreams.

Entrepreneurship has a  sexy appeal in the media right now, but there is definitely more to the story. Can you talk about the sacrifices attached to building your dreams?

Oh definitely. It’s crazy how sexy everyone thinks entrepreneurship is. Don’t get me wrong, I wouldn’t change it for the world but I know first hand that it requires more sacrifices than most people are willing to make.

I’ve lost touch with a handful of people who I would have once considered my closest friends. I’ve missed out on many events that friends and family would have loved to see me at. I’ve made tough choices and while I’m constantly striving to achieve that work-life integration; I know that I’ve made tough sacrifices.

When you’re in your 20s, there is an opportunity at every corner to be distracted. Friends having birthdays, friends asking you to hang out and events that the former you would have loved to attend. Entrepreneurship forces you to say No more times than you say Yes. You often miss out on those weekend binges of Netflix that your friends have. You often miss out on things that deep down you would love to be at. But when you can control FOMO – You can control your actions and ultimately take steps every day to get closer to achieving your goals.

Why do you think everyone should work for themselves?

Because you’re already your own boss.

Tom Peters said it best, you’re the CEO of the most important company in your world. “We are CEOs of our own companies: Me Inc. To be in business today, our most important job is to be head marketer for the brand called You.”

So when I say, everyone should work for themselves, I’m not saying you shouldn’t have a 9 to 5 – I’m saying you should view yourself as an entrepreneur. You should consider how you market yourself. You should consider the investment you make in yourself as research and development. You should consider the way you monitor your spending habits as the accounting department.

Treat yourself like a company.

What other creative outlets do you partake in?

Writing is my #1 creative outlet right now. Beyond writing online and in my books; I write in a journal to keep track of my thoughts, goals and feelings surrounding life and business. While it isn’t exactly a creative outlet – I’d also point to the gym and dodgeball (yes dodgeball) as two other ways that I’m able to get out of my head and relax.

How important is self-education?

I think self education is everything.

Too often do young professionals assume that once they walk across the stage at graduation that they’ve done enough to get their dream job or start the next big thing. In reality, the journey has just begun and you’re only going to grow if you’re willing to learn. Otherwise, you’re just like everyone else who walked across the stage with you at graduation.

We live in an amazing time. With websites like Quora, Lynda, Codecademy, Slideshare and uDemy – it’s easier than ever to gather insights and information from experts. It’s easier than ever to learn how to program or even write a proposal. It’s easier than ever to learn from people from around the world who have gone through the same struggles and challenges that you’re going through. All it takes is a bit of hustle and a commitment to growth.

Hard work truly pays off to those who commit to it!  There’s just nothing like making your own schedule, living out your passions, and creating a need for the world while getting paid.  With his many businesses such as Hustle & Grind, Simmonds excels at motivating aspiring entrepreneurs, or “wantrepreneurs,” to execute their desires, help others, and establish an income within it.  Despite the seemingly futile process and the mega tough devotion, it is always worth it to pave your own way and accomplish personal goals!  Still don’t want to be your own boss?  The answer should be yes this time! Make sure you keep up to speed with Ross on Twitter too!