First off, I hate that title, I’d usually write “How to become financially successful,” but, everyone wants to be rich.

Back in 2012, when WatchMojo

was $1M in the hole (and I had indebted myself to the tune of $500K to keep the lights on), I had the delusional conviction to write about how entrepreneurship was all about “Getting Rich or Die Trying.”

These days, entrepreneurship isn’t a fringe endeavour for misfits, crazies, and oddballs. More kids want to be entrepreneurs than doctors or lawyers. But very few people understand what becoming financially successful actually requires.

It isn’t about hacks, shortcuts, even hustle. Rather, it boils down to a way of thinking and operating that most people simply don’t adopt—or abandon too early.

1. Pyramid of Priorities

Success is relative, fluid and subjective; to me, being rich was never the definition of success. But given that for many it is, this articles will explain how you can become successful in that sense via entrepreneurship. For starters, if you start off prioritizing Profit, you most likely will fail. Why? Near term profits draw competition, and competition evaporates profit. If you want to build a foundation, it always starts with your Principles, because when said and done, that is all you have to start with.

To succeed, you need

  • ambition
  • vision
  • execution
  • persistence
  • luck
  • timing
  • focus (once you know what to focus on)
  • resilience.

Most people invert the pyramid. They chase scale before they’ve built anything worth scaling.

2. Skate to Where the Puck Is Going

Entrepreneurship is not about reacting to the present. It’s about anticipating the future. Whatever you are thinking of, others around the world are as well.

The winners:

  • see inflection point and structural shifts early
  • recognize patterns (ie history rhymes)
  • position before consensus
  • endure the period where they look wrong
  • accelerate and amplify once the timing makes sense

Timing matters—but direction matters more.

3. Timing Is Everything

You can be right and still fail—because you were too early or too late. If you’re building for today, you’re already late. You need to be a few steps ahead of a market, not ten. There’s a balance there that is more art than science.

Google wasn’t the first search engine—it was a late entrant in a crowded field that ultimately dominated. YouTube wasn’t the first video platform.

Markets move in cycles:

  • technology: capability
  • capital: capacity
  • people: conviction
  • behaviour: culture

The best investor and entrepreneur are social scientists, recognizing changes in consumer behaviour.

The skill is not just vision—it’s synchronization.

When:

  • capital is available
  • demand is forming
  • infrastructure is ready

That’s when things compound. WatchMojo was in the third wave of content creators, first wave were so ahead they were DOA.

4. Be Long-Term Greedy

Short-term thinking is expensive. From an old article, “Being Long Term Greedy“:

“Most players are short-term greedy. Short-term greedy types are solely interested in making as much money as possible right now and are likely willing to cut corners. Their mantra is, I want what I want, now! Short-term greedy people almost always lose much more than they win, certainly over the longer term.

Long-term greedy means being a professional, which includes doing your homework, keeping your word, cleaning up messes, honoring relationships with clients and employees. In other words, doing the right thing for no reason all the time.”

The truly wealthy are:

  • patient
  • disciplined
  • willing to defer gratification

They don’t optimize for:

  • quick wins
  • short-term cash
  • immediate validation

They optimize for: equity, control, and compounding

5. Put People Ahead of Profit

This sounds soft. It’s not. From an old article:

When I say “people ahead of profit,” it doesn’t mean don’t care about profits, it just means don’t focus on profits especially if it comes at the expense of your real asset, which are people – particularly in businesses that thrive off of intellectual property and goodwill (brand equity). Aside from it being the decent thing to do, reality is if you want your business to be valued more, that means you have to treat your clients as well as you can… and that starts with treating your employees as well as you can and understanding that [their] people (their kids, etc) come before [your] bottom-line (it may not be PC, but this is why eventually I matured and parted ways with employees who weren’t team players, because they adversely affect your A-players.

Businesses are:

  • relationships
  • trust networks
  • human systems

If you prioritize profit over people:

  • you burn bridges
  • you lose optionality
  • you cap your upside

If you prioritize people: profit becomes a byproduct.

6. Be Realistic: No One Is Focused on Helping You

I don’t want to sugarcoat things, at the same time:

a) I’ve been genuinely humbled, flattered, and honestly blown away by the messages of support and encouragement. But I also recognize where that comes from—the utility and emotional pull the Expos, and their potential return, represent for people. That’s why I view this as more than a project; it’s a civic duty, almost a purpose. If this was a personal project, no one would care (nor should they). Short of Lucifer himself leading the charge, people support you if there’s a clear benefit to them.

Selfishly, as a competitor, it’s also liberating. It allows me to unshackle myself and operate without restraint—déchaîné, as we say in bon québécois. Patrick Roy didn’t care what people thought. Maurice Richard wasn’t optimizing for optics. They had a level of drive and tenacity that most people simply couldn’t comprehend.

b) That said, I’ve also been struck—if not shocked—by how small-minded, self-interested, and passive many people can be. I don’t focus on them, I am human so sometimes I’ll react, but I quickly adjust and course correct.

Entrepreneurs often assume others think like they do… until they realize almost no one does.

Ultimately,

People are not:

  • against you
  • plotting against you

They’re simply: focused on themselves.

Once you accept this:

  • you stop expecting help
  • you stop taking things personally
  • you operate with clarity.

7. The Paradox: You Must Prioritize Others

Here’s the contradiction:

No one is focused on helping you. Yet your success as an entrepreneur depends on helping others: clients, employees, suppliers, investor, community.

This is where most people fail.

The right mindset:

Ask: “How do I create value for them?”

Do that consistently—and it compounds.

8. Master Delayed Gratification

This is where the separation happens. It takes

Missionaries and Mercenaries

to win.

Mercenary mindset:

  • hourly pay
  • immediate reward
  • short-term thinking

Missionary mindset:

  • equity
  • ownership
  • long-term upside

You can’t build wealth if you constantly choose: cash today over value tomorrow. This is also why I say entrepreneurship is a privilege, as it’s hard to adopt a long-term value when you have bills to pay and mouths to feed. It’s not a coincidence I became an entrepreneur after I got married but before I had children.

9. Perspective + Positivity

Entrepreneurship is:

  • uncertain
  • volatile
  • emotionally draining

If your perspective is fragile, you won’t last.

You need:

  • persistence
  • resilience
  • optimism grounded in reality
  • the ability to zoom out

This isn’t motivational—it’s functional. The glass is filled as it is, it’s up to you to view it as half full or half empty.

10. Humility Wins

The fastest way to fail: thinking you’re above the work.

No task is beneath you:

  • early sales
  • customer support
  • fixing problems

Ego kills execution.

Humility:

  • keeps you learning
  • keeps you adaptable
  • keeps you grounded

11. Optionality Is Power

Don’t celebrate prematurely.

Don’t build a single path—build multiple paths, multiple avenues, multiple doors.

Optionality reduces risk and increases leverage.

Redundancy minimizes risk.

12. Momentum Compounds

Success rarely comes from one big move.

It comes from:

  • consistent action
  • repeated exposure
  • stacking small wins

Momentum creates: credibility, opportunities, luck (which isn’t luck, but probability).

Final Thought

None of this is complicated.

But almost none of it is followed consistently.

Most people:

  • chase shortcuts
  • prioritize comfort
  • avoid risk
  • think short-term

Wealth doesn’t come from knowing these principles.

It comes from: living them, repeatedly, over time.