TrenchLife: The road to entrepreneurship & starting your day one

The Coach Next Door - Jenna Zeng
10 min readMar 18, 2022

Grit: the ability to keep working towards a goal, overcoming challenges, and sticking with it even when thing’s get hard.

Would you describe yourself as gritty? By definition, that is what Garry Gallimore is.

“Whatever I desire in life I’m going to have to put my shoulder to the wheel and work and sweat it out until I get the results I desire.” — Garry Gallimore #TrenchLife

We had the opportunity to sit down with Garry Gallimore, the CEO and founder of TrenchLife Apparel. He is a successful family man, entrepreneur, and business owner.

Business, athletics, whatever your goal, Garry shares how to start and continue on the path of relentless success. This is a man you’ll want to listen to!

In this article we discuss:

  1. Turning your passion into a business
  2. The one thing you need to run a successful business for the long haul
  3. Why you should quit comparing your successes to others’
  4. How to show up daily in your business
  5. The supporting cast that inspires greatness
  6. The power through growing and giving back within your community
  7. Actionable steps on how to get your business up and running

Who is Garry Gallimore?

Garry is a decorated athlete having won two bronze medals overseas while playing basketball for Team Canada and was named defensive player back-to-back years in a row with Usports.

Not only does Garry share his inspirational story, but he also gave us actionable tips on how to turn your passion into a business, how he carries himself through adversity in business and how to build the proper foundation for a long and lasting business by ensuring the proper supports are in place for you to thrive.

From family and friends, to believing in yourself, Garry shared a story of growth through action every day.

Turning passion into business

Garry was able to turn his passion into a business as a vehicle to share a message of TrenchLife: Since Day One.

Since day one — what does that mean?

While Garry was abroad to play basketball and represent Team Canada, he had one message that stuck with him through all the adversities and unknowns of his athletic career: TrenchLife: Since Day One.

Garry stated that we all have a day one and anything you want in life you must work for it, you must be willing to sweat for it and be willing to get dirty and uncomfortable; it’s a message of growth and development towards success by taking one step at a time.

Whatever you’re doing, we all have a day one — you just need to get started.

What the TrenchLife looks like

Initially the TrenchLife was a motivational mantra to Garry when he was a professional athlete playing basketball.

During trying times of whether or not we would get the opportunity to play for the team, or when the demand required of his body and mind was high during the season, he always fell back on to these simple words: TrenchLife.

Fast forward from this initial self-motivational message to himself to several years later where he’s now a successful business owner and embodies a message that has had a much bigger impact of his life, family, and community than he could have ever imagined — he’s created a movement.

From humble beginnings of selling shorts from the truck of his mother’s car, to building a thriving apparel business, Garry has seen it all and done it all himself to build his business and brand since day one.

Currently for his ‘day’ job Garry works as an OC Transpo Rail Operator, and when he’s off duty from this job he’s right back to the grind and is the visionary behind TrenchLife Apparel.

Despite only having 24 hours in a day and a jampacked schedule, Garry is in the trenches grinding and building his vision one brick at a time.

The one thing you need to be successful

In 2022, literally overnight, it’s never been so easy to start a business.

Within hours we can have a website up and live, social media accounts for marketing and ads can be running in minutes and voila! Suddenly you’re a business owner!

We no longer need to rent a physical space to sell a product or service– in fact when polled, 65% of people said they preferred online shopping than in-person.

Best of all, you’re in the driver’s seat and you can now control how fast you scale your business and how much you get paid.

One question: what should you do?

Maybe you’re in the idea phase, already have a business, or know you want to own something of your own, but you aren’t quite sure what yet.

The one thing you need to be successful is: passion.

“When you want to succeed as bad as you want to breathe, then you’ll be successful.” — Eric Thomas

Without passion you will not be successful

Life is busy. That is a fact! If you asked any entrepreneur if there is enough hours in a day, they would all say “NO!”.

Garry knows this well, as he is required to wear many hats in his business. He’s the head marketing, merchandising, logistics, communications, customer service, and on and on… Basically you name it, and he likely does it!

Read more: Story of a naive entrepreneur: my 20K mistake

Is it all fun to do? Nope. But the fuel that keeps Garry moving forward is his passion.

Passion cannot be forced or bought. These are gifts that you are born with to share with the world through message, acts or services.

Garry has embodied his passion through all three: message, acts and services.

He’s in the trenches daily working and demonstrating that we all have a day one — you just need to get started.

He laid it out simply: if you can look back and be further from your day one and closer to your end goal, then you are successful.

His passion behind the message is what drives him to show up daily and keep on working.

So, what’s your passion?

Quit comparing yourself to others’ highlight reels on social media

Growing a business is hard. It’s not for the weak or weary and you’ll question your sanity many times.

Garry spoke about the many logistical problems from manufacturing overseas, to the cost of running a business and scaling and growing it as quickly as he’d like.

It can be easy to hop online and compare what you’re doing to a colleague or competitor and quickly spiral while watching the ‘best of’ highlight reel that everyone is posting — we all do it!

Garry cautions to avoid getting wrapped up in this comparison game and to focus on putting your head down and keep working at your business.

Cue Grandma’s voice saying, “mind your own business!” and it’s never been so relevant.

Be wary of the comparison game and tread lightly when others try to pull you into it as well [more on that below].

You’re never going to be good at everything

Learning to balance work, life and more work is a difficult act to nail.

Like many of you, Garry has many other priorities pulling at the waist-side and this can be so hard for a business owner to balance.

Read more: PSA: You’re not good at multi-tasking & why you should quit

Patience and consistency are key to nurturing your business in the early stages.

Remember: small steps daily = leaps forward over time.

“Most people overestimate what they can do in a year and underestimate what they can do in ten years” — Bill Gates

Showing up day after day putting in the time and effort will pay off. Stay the course and be relentless towards your passion.

Showing up every day means growing every day

Although other priorities like family might overshadow the growth we may like to see, staying consistent is the key to scaling and growing any successful business.

Despite working a full-time job, being a husband and father to three young children, Garry still shows up and then grinds it out every day.

Garry reminds us that consistency and progress are the small steps that matter.

Be committed in the long haul. If it’s 1, 5 or 10 years will you see it through?

Surround yourself with inspiration

Garry is an athlete by trade and a team’s man. You can tell by the way he speaks about the people who have inspired him the most, his very first team: his family.

His perspective on his family was so beautiful and genuine; he shared that for you to grow yourself, you must show and pay respect to the people that surround you and lift you up.

From an early age Garry found direction from his parents and siblings, and then later in life adding to the mix are his children and wife that continue guide and uplift him.

Overall it’s safe to say that these supports have made a profound influence in how he operates and carries himself and the general success of TrenchLife Apparel.

Think about the people that make you feel like the best version of yourself when you’re around them. Be with them, surround yourself with this support system and you’ll see the results.

When inspiration is low and doubt is high

Not everyone is going to be in your corner.

If we’re not surrounded by the right people, the road of entrepreneurship can be a lonely one.

Read more: New year, new goals and a whole lot of analysis paralysis

We hear this story so often of the eager entrepreneur excited to share their idea and/ or business with friends and family, and then suddenly they’re met with comments of doubt, worry and comparison to other businesses within the same breath.

The sad part is that when met with this doubt, the eager entrepreneur is no longer eager or excited.

They’ve taken on these doubts that aren’t even theirs and now suddenly belief in their idea and themselves is quickly fading.

Cutting people off

The truth of the matter is that not everyone will want to see you succeed. And that’s OK.

We know people will naturally compare you to others in the same field that you’re in and point out that you’re not where this big successful person and/ or business is — yet.

The fatality of this comparison can make you sublimely feel like you’re never doing enough.

In your business there is no room for people with ANTs [automatic negative thoughts].

When instead of words of encouragement, it’s negativity being spewed, Garry advises to not be afraid to cut people off.

Do not let others stop you on your day one.

In life if you do anything people are going to judge. Alternatively, if you fail to do anything people are going to judge. Either way, you can never please everyone. All that matters is that you please yourself.

Growing a community

Through his message, Garry has been able to impact not only his life but the lives of the people around him.

He’s built a brand that is well on its way to building authority within the community and the apparel business.

He believes that growth means lifting others up with him, and he’s found many way to give back to his community as his own success grows.

He mentioned that TrenchLife Apparel supports by donating some profits to a local shelter in Ottawa and he donates the old season’s clothing to those less fortunate in the community.

Garry taught us that being busy is no excuse that you cannot be of service to or within your community.

How to turn your ideas into actions

We have our passion, and we’re in the right frame of mind, so how do we get started?

Garry outlined the necessary steps to staring a startup the right way for the long haul.

  1. Find your passion
  2. Preparation: research the market, competition, fees, licenses, operating costs, etc
  3. Surround yourself with great support systems/ remove the ones that aren’t serving you
  4. Start your day one
  5. Stay the course — don’t give up on yourself.

Read more: How to Start a Side Business:Tips from a Successful Real Estate Investor & Doubling his Productivity

TrenchLife: Since Day One

This means we all have a day one, now what happens next? What are you going to write for your story? This all depends on what you do now.

“The big secret in life is that there’s no big secret. Whatever your goal, you can get there if you’re willing to work.” — Oprah Winfrey

Garry is such an inspiration to us, and we have found so many great takeaways for ourselves in both our personal and business lives from this amazing interview!

Now you should connect with Garry!

He is keen on sharing information, so if you have comment or questions, please reach out!

Follow TrenchLife Apparel HERE.

Want to shop? Check out the TrenchLife Apparel website HERE.

Being in the digital era we’re in it’s never been a better time answer your calling!

If you’ve been thinking on an idea, we urge you to just do it! Put your passion out there to serve your purpose to the world.

We’ll be waiting.

Much love,

Jenna Zeng, Team StaffNet



The Coach Next Door - Jenna Zeng

A bubble tea obsessed, toddler mama and a mindset coach. I'm here to support with all things and personal development & parenthood.