How I Got Where I Am Today

Photo by Jon on Unsplash.

Chasing Dreams & Fighting for Dreams

Failure has a distinct taste. It happens before your very eyes and you feel like there’s absolutely nothing you can do. It steamrolls you. Takes you down. Grinds you to dust.

I’m where I’m at today because of my childhood and experience working with small businesses.

My journey feels like a 20-year emotional battle. But I suppose every moment taught me a lesson. By no stretch do I proclaim to be wildly successful, but I’m definitely making strides in that direction.

Like a flower that blossoms, transformation takes time, energy, and resources. Think of it like evolution.

We all start off as kids with a blissful view of the world. We imagine the world and all its possibility, but then we start to hit bumps (loss of family members, friends, career hits, etc).

Those bumps can crush our dreams, but some of us hang on.

I still fight for my dreams.

And there’s a big difference between chasing dreams and fighting for dreams.

Dream Chasers‘ are the scary people who relentlessly gamble everything they have to achieve their dreams. ‘Dream Fighters‘ are the people who make the sacrifices to achieve their dreams in a calculated and risk-averse way.

So when I advise people to follow their dreams. I mean to fight for them. To make the hard decisions, to take pay hits, to offset $10k from their salary in order to hire the right part-time talent.

Ascendence won’t come easy, but trust and believe in the process.

Shoot for the moon. Even if you miss, you’ll land amongst the stars.

Mowing Lawns & Selling Notes

There’s a great photo my friend Thomas Clark shared on Facebook earlier this year.

I mean. That was it. My parents didn’t give me an allowance. Me and my siblings had to work for our money (and we still do).

Luckily our grandfather supplied a healthy amount of work for his real estate business, Myrman Realties.

I mowed lawns and did landscaping work from age 11 to 20.

But that wasn’t all.

I wasn’t really an ‘academic’ kid. I rarely missed class, but my grades weren’t great.

My mom enrolled me in an afterschool program to get help on my assignments. The tutor made me type my notes.

I can’t remember the exact transition to selling notes, but I mean… I literally had the product. My tutor made me create it.

I slung notes for 1 year. Made about $1,000.

University & The StFX Business Society

Once again my grades weren’t great.

I would need to play the ‘interesting experience’ card if I was ever going to get ahead in my career (or crack down and really focus on my studies).

I chose ‘interesting experience’.

I joined and aggressively worked to grow the StFX Schwartz Business Society.

I eventually became President of the society and worked with an amazing group of people. We held a lot of events, made decent money, and enhanced the StFX experience for business students.

Failure & Stubbornness: Phased.io

My first job after graduating university was working at Volta Labs (an incubator) in Halifax as an unpaid intern. I saw founders start, grow, and close their businesses.

It was a tough place to work. Either your business made it, or it didn’t (and you were out of a job).

I thought the experience would give me a healthy dose of what it’s really like to start a business. After a few months, I thought I had learned enough to go out on my own.

I joined an IT program called UIT Startup Immersion where students learned how to build apps, websites, and run fast-growing technology businesses.

Through this experience, I started an app company called Phased.io – an app for succession planning.

We had government support, community support, advisors, mentors, networks, programming, you name it.

But despite our energy, Phased didn’t have the momentum to traverse the cold, hard market.

We closed our doors.

Finally a Win: SUP Baddeck

I needed to make money.

I had $5,000 in my bank account ($2,500 from my dad) and decided to start a paddle board business in Baddeck, Nova Scotia.

If you recall from my previous article, years before Phased.io, I created a YouTube video teaching people how to paddle board. In my time of need, THIS (paddle boarding) was the only way I knew how to make money.

I started Cape Breton Island Watersports Inc and operated under the brand name SUP Baddeck (SUP meaning stand-up-paddle).

SUP Baddeck was a great chapter in my life. I built a profitable business, fell in love, and repaid my debts.

Where Phased.io was a flop in my life, SUP Baddeck was my redemption of hope.

If not for SUP Baddeck and earning that small taste of victory, I don’t know where I’d be today.

Raising the Bar: Toronto

I had a tech company that failed. I had a watersport company I sold.

Now what?

Was the pinnacle moment of my life SUP Baddeck? Was I going to fizzle out and be someone at a bar who kept looking back on the ‘good old days’?


I decided to venture into the unknown, to play my hand at other businesses.

A business friend of mine was starting an English Language School in Toronto and offered I join the team.

I packed my bags and moved to Toronto 2 weeks later.

We were able to get that business running quite quickly. Still to this date, I’m amazed at how large and fast the international student market is growing.

The experience with that business was good, but more and more it led me to teaching English and helping operate the business (not actually doing much marketing).

I searched for new opportunities and found a promising opportunity in Halifax, Nova Scotia at a small marketing firm.

Once again, I packed my things and moved to another city to join another small business.

The Second Coming of Failure: Halifax

Returning back to Halifax was nice. The city hadn’t changed too much and I already knew my way around. Plus, I got to finally move in with my girlfriend who was studying in Halifax.

It was nice. I plugged away on projects in my evenings and we did date night once a week. I became very cozy.

Also, I was really happy with work. My boss had built a debt-free, investor-free, VC-free organization with net-positive cashflows. Seeing how he ran his organization was incredibly valuable to see. I was learning a lot from my boss.

But all good things eventually come to an end.

Work was getting busier. Expectations were increasing. My sister was experiencing pregnancy problems and my girlfriend wanted more in life.

This was my second coming of failure.

My inability to balance work-expectations with at-home issues snowballed into somewhat of a disaster.

My girlfriend broke up with me and I came crashing down.

I slipped up at work. I made mistakes. I struggled to keep up. Errors happened and I couldn’t explain why.

I saw where things were heading, so I took it on myself to leave.

I submitted my letter of resignation and moved back home with my parents to recalibrate and figure things out.

I don’t know if anyone I worked with in Halifax is reading this, but if they are, I’m sorry I couldn’t turn things around. Reading about your success months later was very pleasing to hear. I wish and hope all the best for you. Thank you.

Back to Marketing Management: Securicy

I returned home for the first time in years. The streets were the same. The stores were the same.

At first glance, I sighed at how little had changed (as cities like Toronto were rapidly growing).

But a lack of change can be a good thing. Cape Breton is my home and it’s exactly how I remember it; a good place to hit the reset button.

As for work, I wasn’t sure what to do. I was most interested in marketing, but I didn’t see any companies I was eager to work with. In a way, I felt like a marketer with nothing to market. That is, I could do marketing, but I hadn’t found the industry I was most passionate about.

I felt like a marketer with nothing to market.

I started volunteering with local businesses to help them improve their marketing operations. I took on some contract work to keep cashflow up, but eventually started working with Securicy – an app for information security programs.

Securicy was accepted as a participating company of Techstars, a business accelerator in Boston, Massachusettes. I originally worked with Securicy as a consultant doing Marketing Analytics, but later joined their team as the Marketing Operations Manager.

The redeeming moment was becoming a manager again. I hadn’t actually been in a management position since leaving my own businesses years ago. I accepted that I would need to work at the bottom, learn from others, and EARN my way to management (instead of just make myself the CEO in my own business).

This was a happy moment in my life.

Where I’m at Right Now: Top-of-Funnel Marketing

Despite the ups and downs over the years, I’m still not done my journey.

While in Boston with Securicy, an investor named Jay sat with me to discuss Securicy’s marketing operations and analytics. His words set me on another path.

I have no doubt in your ability to manage and drive the funnel, but where my largest concern lies is your ability to drive Top-of-Funnel engagement.

He was right. My career taught me how to operate marketing departments, but not how to get engagement, connect with others, and actually help others along the customer journey.

To date, a lot of my career was doing day-to-day tasks, managing CRMs like Hubspot and Salesforce, and reading marketing data to inform managers and investors.

The thing I did not thoroughly understand was top-of-funnel engagement; how to get conversations happening organically.

His words sat in my head for a few weeks, then I got to work.

I began experimenting; posting more content and connecting with audiences.

Whenever I hit a win, I’d bring my findings back to Securicy for implementation.

Campaigns, brand awareness, ads, and lead generation are only part of the marketing puzzle. More and more I see personal branding playing a role in marketing, but probably the most notable win was developing the ability to empathize with people (deeply and emotionally).

Emotional intelligence is a very complex topic, especially when promoting and selling products that people don’t fully understand.

The traction I’ve made to date is a start, but there’s still a whole lot left to uncover.

Fighting for Dreams

I actively work to become one of the world’s greatest marketers, but I’m often conflicted by marketing.

Isn’t the point of marketing to make money?

Having reflected on marketing a number of years now, I understand that the ‘True North’ of marketing is to help others turn their dreams and passions into reliable, profitable businesses.

Whether it’s information security or becoming a popular YouTuber, I work day-in and day-out to help people from all walks of life discover their passions, reach their goals, and to overcome challenges associated with growth.

I’m no longer a marketer with nothing to market. I’m a marketer who helps people achieve their dreams.