If you don’t swing, you don’t hit.
- Sales
- Capital
- Hiring
- Cash flow
- Marketing
- Operations
- Firing
- Systems
- Technology
- Leadership
- Margins
- Compliance
And eventually, how to stop trying to do everything yourself.
I’ve built an eight-figure business. I’ve raised millions in private capital. I’ve built technology companies, software platforms, sales organizations, marketing systems, development teams, executive teams, and products used throughout the financial trading industry.
But none of it happened in a straight line. I’ve made expensive mistakes. I’ve taken risks that worked and risks that didn’t. I’ve hit ceilings. I’ve had to pivot. I’ve had to rebuild.
As a kid, while my friends were doing what kids normally do, I was taking apart bicycles, rebuilding BMX bikes and finding people in the neighborhood to buy them. Before I was old enough to have a traditional job, I was helping at the local corner store, counting worms and preparing fishing supplies for customers heading out on the water.
Then I started working in my father’s businesses. My family operated resorts, and I grew up around tourism, fishing and hunting. I guided. I drove boats. I worked with guests. I helped fishing television crews. And when my father traveled to sports shows and conferences — before the internet became the primary way businesses generated customers — I watched him sell.
Eventually, I was helping book trips, talk with customers and close business myself. I didn’t know it at the time, but I was learning some of the most important skills I would use later in life.
- How to work
- How to sell
- How to connect with people from completely different walks of life
- How to communicate
- How to serve customers
I’ve always been comfortable communicating. Put me in a room with people and I’ll talk. Put me on a microphone and I’ll communicate. Put me in front of a customer and I’ll find out what they need.
Some of that came from experience. Some of it came from watching my father. And I believe some of it was simply a gift God gave me. That ability eventually became one of the foundations of my career.
Because no matter how sophisticated a business becomes, somebody still has to communicate the value. Someone has to sell the vision. To customers. To employees. To partners. To investors. To the market.
My career didn’t begin behind a desk. After my family’s businesses were sold and I left home, I went to Alberta and worked in the oil fields. I worked for AKITA Drilling out of Nisku on large drilling rigs throughout Northern Alberta and even into the Northwest Territories.
I started at the bottom as a leasehand. I moved to roughneck. Then motors. Eventually I was responsible for major operating systems on large drilling rigs.
It was hard, physical work. Long hours. Extreme conditions. And an environment where everyone had to do their job because the person beside them depended on it. I spent years doing it. And I’m grateful I did. It taught me a version of work ethic that you can’t learn from a business book.
But I also knew I wanted something different for my life. So I went back to school.
I completed a three-year advanced diploma in business finance with studies focused on corporate finance and statistics. I completed the educational requirements associated with financial-planning studies and also passed Canadian securities licensing examinations, although I ultimately chose not to pursue a career practicing in those fields.
Instead, finance led me toward the financial markets. And the markets eventually led me toward technology. I became Director of Business Development for a quantitative trading software company in Calgary. That role became one of the most important business educations of my life.
I wasn’t only learning sales. I was seeing how a software company actually operated — development, product, sales, marketing, affiliates, webinars, funnels, customers, management and technology. I was watching all the pieces interact.
There was no venture round. No office full of employees. No giant team. No safety net. I started with roughly $10,000 of available credit and an idea.
And I didn’t immediately quit my job. I built in parallel. During the day, I worked for the company employing me. At night and on weekends, I built the company I wanted to own.
There wasn’t immediate money in it. There wasn’t applause. There was just a vision and a willingness to work on it when nobody was paying me to do so. Eventually I reached the point where I knew I had to make the swing. So I did.
Ideas are everywhere. Demand is different. I understood the financial trading industry. I understood the customer. I understood how difficult trading was. And I understood that traders continually searched for better strategies, software, education, coaching and technology.
There was existing demand. So instead of trying to convince the world that it needed something completely new, I built solutions around problems people were already trying to solve.
For me, software became an extraordinary business model. Build the intellectual property once. Continue improving it. Build distribution around it. And create margins that could fund growth. That doesn’t mean my model applies to every company. It means I learned a principle that does:
When I started developing trading applications, I studied the competition constantly. What were they selling? What did customers like? What was missing? Where could we build something materially better?
I didn’t want to create another generic tool in a crowded market. I wanted our products to stand apart. And when I believed we had built something superior, I wasn’t afraid to charge more for it. Higher pricing didn’t always mean more customers. Sometimes it meant fewer. But it could also mean better customers, stronger margins and more revenue.
- Sales
- Technology
- Operations
- Finance
- Executive leadership
- Marketing
- Product
- Customer success
- Management
Getting a company started requires one set of skills. Building an organization requires another. Eventually, I couldn’t personally sell everything. I couldn’t manage every developer. I couldn’t oversee every customer. I couldn’t create every campaign. I couldn’t make every decision.
So we started building departments. That required processes. SOPs. Dashboards. Accountability. Meetings. KPIs. Reporting. Management structures. And delegation.
This is where a lot of founders struggle. The same founder mentality that gets a company off the ground can eventually become the bottleneck preventing it from growing.
I’ve always believed strongly in revenue. Not vanity metrics. Not attention for the sake of attention. Not growth that has no path toward economic value. Revenue.
If you have something that’s working, don’t become so distracted by everything you could build that you stop feeding the engine that’s keeping the company alive. Sometimes one division is working while another is still being built. One offer is producing cash while another needs development. One acquisition channel is performing while another hasn’t found product-market fit.
Don’t abandon the larger vision. But understand what is paying for that vision. Double down on what is cash flowing while you build what comes next.
One of the biggest reasons our companies grew was consistency. We marketed aggressively. We sold aggressively. We ran webinars constantly — at different points, three or four every week. Multiply that across a year. That’s hundreds of opportunities to educate customers, demonstrate products, answer objections, create relationships and generate revenue.
People sometimes told us we emailed too much. We marketed too much. We ran too many webinars. But those systems became fundamental to our customer journey and our revenue.
- Organic content
- Setters
- Affiliates
- CRM
- Conversion metrics
- Paid acquisition
- Closers
- Tracking
- Media buying
- Webinars
- Funnels
- Dashboards
A technology company isn’t just a collection of developers. You need product leadership. Development. QA. Infrastructure. Research and development. Project management. Prioritization. Documentation. Release cycles. And an operating system capable of keeping everyone aligned.
We’ve used agile operating frameworks, regular development scrums, structured QA processes, product roadmaps, and recurring management meetings to keep technology organizations moving. But the lesson isn’t that every company should copy our exact meeting schedule. The lesson is that every growing company eventually needs an operating system.
- What are we building?
- Who owns it?
- How do we measure completion?
- What matters most right now?
- Why are we building it?
- When is it due?
- What is blocking us?
I’ve built small teams. I’ve built larger teams. I’ve hired people who became critical to the organization. I’ve hired people who weren’t the right fit. I’ve promoted leaders. I’ve made hiring mistakes. And I’ve learned how important it is to protect the standard of the organization.
You want A players. But keeping A players isn’t simply about demanding performance. They need ownership. Clarity. Resources. Accountability. Trust. And room to do the job you hired them to do.
One of the hardest transitions for me as a founder was understanding that delegation isn’t simply giving someone a task. It’s giving qualified people responsibility and then allowing them to own it. Today, some of the most important things happening across our businesses are possible because I have executives and leaders I trust.
- Accredited investors
- Valuation
- Securities counsel
- Pro formas
- Data rooms
- Compliance
- Reporting
- Private placements
- Share structures
- Financial models
- Investor presentations
- Due diligence
- Cross-border considerations
- Investor relations
Raising capital taught me that having a great company isn’t enough. You have to understand how to communicate the opportunity. You need the numbers. You need the story. You need the structure. You need the documentation. And you need qualified legal, accounting, securities, tax and financial professionals around you.
Through that process, our businesses have raised millions of dollars in private capital. Today, I’m going through another evolution as we work toward a larger institutional Series B round. That brings another level of scrutiny. Another level of diligence. Another level of financial discipline. And another level of learning.
Since starting my first technology company, the businesses I’ve built have generated eight figures in revenue. I’m proud of that. But I also think it’s important to explain what that means. It doesn’t mean every year was perfect. It doesn’t mean every decision worked. It doesn’t mean I personally have eight figures sitting in a bank account. It means we built an eight-figure business.
And building it taught me something that applies at almost every level: every business eventually hits a ceiling. Sometimes the ceiling is sales. Sometimes it’s marketing. Sometimes it’s the product. Sometimes it’s capital. Sometimes it’s management. Sometimes it’s margins. Sometimes it’s the founder.
- Recurring revenue
- Intellectual property
- Technology
- Customers
- Distribution
- Repeatability
- Margins
- Processes
- Brand
- Data
- Management
- Scalability
I believe founders should understand what makes a company valuable — including the ability for the business to operate beyond the founder. Those things create options. Maybe you sell. Maybe you recapitalize. Maybe you acquire. Maybe you raise institutional capital. Maybe you continue operating it for decades.
I don’t believe the entire purpose of entrepreneurship should be chasing an exit. If you’re constantly thinking about selling the business, you can lose sight of building something worth owning.
One of the most expensive mistakes a founder can make is believing they need to figure everything out themselves. I made that mistake. There are lessons I learned through years of trial and error that someone with the right experience could have explained to me in an afternoon.
That doesn’t mean every advisor is valuable. They’re not. Titles are cheap. Opinions are everywhere. Strategic advisory is different. The right person, with the right experience, addressing the right problem at the right time can change the trajectory of a company.
- Avoid a bad hire
- Prepare for a capital raise
- Restructure a team
- Fix an inefficient sales structure
- Challenge a financial assumption
- Identify the actual constraint
- Identify the wrong business model
- Introduce the right partner
- Stop you building the wrong thing for twelve months
- Building from zero
- Pricing
- Marketing systems
- Development operations
- Founder delegation
- Investor relations
- Strategic partnerships
- Finding demand
- Margins
- Webinars and funnels
- Hiring and leadership
- Cash flow
- Financial modeling
- Scaling and pivoting
- Product development
- Sales organizations
- Technology teams
- Building executive teams
- Raising private capital
- Data rooms
That’s an important distinction. I’m not standing on the other side telling you I figured everything out. I’m running companies. Building technology. Managing teams. Raising capital. Developing products. Making decisions. Solving problems. Making mistakes. And moving into new stages of business that require me to learn all over again.
I’ll share that journey through my content. The wins. The mistakes. The frameworks. The systems. The decisions. And the lessons I’m learning while they’re still happening.
If you’re a founder, entrepreneur, executive or someone trying to build something of your own, follow along. Ask questions. Challenge ideas. Comment. Get involved. You may find something from my experience that saves you a few mistakes of your own.
It took me to an oil rig. Back to school. Into finance. Into trading. Into software. Into entrepreneurship. Into leadership. Into raising capital. And into building an eight-figure technology business from an idea that started with roughly $10,000 of available credit.
But the number isn’t the lesson. The lesson is everything required to get there.
- Find the demand.
- Protect the margins.
- Hire great people.
- Ask for help.
- Build something valuable.
- Generate cash flow.
- Give them ownership.
- Raise capital when the opportunity justifies it.
- Learn how to sell it.
- Build the systems.
- Know your numbers.
- Keep adapting when the business hits another ceiling.