Entrepreneurship is Game Selection with Serial Entrepreneur Xavier Helgesen

Guest:

Xavier Helgesen

Entrepreneurship is Game Selection

The biggest mistake a founder can make:

Choosing the wrong game.

When you start a business, you're not just launching a company – you're choosing a game to play. 

And each game comes with its own set of rules: margin profiles, competition levels, capital requirements, and more. Yet, many entrepreneurs rush into this decision too quickly, resulting in years spent grinding at a game that’s rigged against them from the start.

I didn’t fully understand this until well into my second decade as a founder. Like me, Xavier Helgesen has been starting and building businesses for over 20 years. We've both created businesses from various places:

  • From our dorm rooms, fueled by “hey, that would be cool” inspiration. He launched an online bookstore; I started a late-night crepe stand—both aimed at college students.
  • From our hearts, driven by a desire to make the world a better place. Both of us launched for-profit social enterprises in Africa.
  • From our wallets, focused simply on trying to make money. The goal was straightforward: provide a good product or service profitably.

Xavier’s idea that "Entrepreneurship is Game Selection" hit home for me: You need to be very deliberate about which game you’re signing up to play.
Picking the wrong game can cost you years—maybe even decades. On the other hand, choosing the right game sets you up for countless opportunities and successes.

The Trap of Following Your Passion

One of the biggest myths in entrepreneurship is “follow your passion.” While passion can provide energy, it can also lead you into a game that's inherently a poor business choice. As Xavier pointed out, just because you love guitars doesn’t mean opening a guitar shop is a smart move. Loving music is great; opening a small retail store and hoping customers will walk in is not.

Passion Emerges with Mastery

But here’s the thing: passion isn’t static. It can grow and evolve from developing mastery in a field, even if it wasn’t your first love. Sometimes, passion emerges not because you chose something you loved from the start, but because you became exceptionally good at it.

Choosing the Right Game

So, how do you choose a game that is wise to play?

Focus on Your Unfair Advantages.

Where do you have a unique edge? What is it about your skills, network, or resources that gives you an advantage over the competition? Find a game where these unfair advantages can shine.

Leverage Unique Insights.

Do you have a unique perspective or insight about a market opportunity or trend? Is there something you know that others don’t see yet? These insights can help you play the game more effectively and achieve disproportionate success.

The Bottom Line

As a founder, you're always choosing a game. Choose it carefully. Define what winning looks like, ensuring that it aligns with your values and has both impact and financial implications that feel authentic to you. But be intentional and set yourself up to win on your terms.

Your decision will set the stage for your entrepreneurial journey and determine whether you spend your time slogging through a game stacked against you or thriving in a game where you have a real shot at success.

Choose wisely. Your future depends on it.

"For more from Xavier, check out his company Enduring Ventures and his writing on X.

Get in touch

Matt acquires or invests in cash-flowing digital businesses with $1-$5M in EBITDA.

Occasionally, he takes on advisory engagements for interesting projects. If this is of interest, feel free to share more.

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