The #1 Skill You Need to Build a Successful Business

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Lately, I have been getting a lot of questions about what it takes to take the leap into entrepreneurship and stick with it.

To be honest, the question still surprises me as I am such a newbie at being a founder. While this is not my first attempt, it is the most successful one and the one I have done full time. All other attempts were side hustles.

If there is one thing I have learned over the past year, it is that entrepreneurship isn't something you can learn in school or by listening to a podcast.

It is something you learn by doing the thing.

In my humble newbie founder view, the number one skill one needs to start a company from an idea and scale it to a successful business is not a business skill.

It is a soft skill. That skill is courage.

I say this as someone with an MBA from one of the top business schools in the country and someone who very much believes in higher-education and degrees. My time at Schulich changed my life. I learned hard skills I still use every single day and it opened doors that would never have opened otherwise.

But, no course or textbook can teach you how to start and run your own company.

You can't learn how to pitch your idea to your first client, deal with all the firsts at once - lawyers, loans, investors, vendors, and set up the foundations of your business from a course. Then, there is the endless juggling act of being HR, Finance, Strategy, Customer Service, and Operations all in one day.

And, I won’t get started about founder-led sales of early-stage startups. That alone can have you questioning your sanity about your life choices.

It's like a freefall that never ends. That's entrepreneurship in one sentence. Until you exit stage right.

So, if you're building a new business from scratch, changing careers, or stepping into a bigger version of yourself, here are three ways to find more courage in this season.

1. Embrace the vulnerability of being a beginner. This was the very first thing I had to wrap my head around. Despite having this image of "a seasoned business leader," I had to show up in a space that was unfamiliar. And, I had to be okay with being seen pivoting, trying my hand at something new, and yes, doing it publicly.

It is okay to be a beginner at any age and any stage in your career. You can be a beginner over and over again. The leaders who inspire us most are the ones brave enough to say, "I'm learning as I go." Courage grows when you give yourself permission to start over without any judgement.

2. Do it scared. If you're waiting for the fear to go away before you take the leap, you will wait forever. The fear won't disappear and courage won’t randomly start knocking at your door one morning. It’s not something you find and then act on one day. 

Courage is built by doing it scared.

Every time you do the thing that terrifies you, like send the cold email, make the pitch, launch the product - you're literally building your courage muscle.

The first time I pitched Executiv to a potential corporate partner, I actually felt like I was going to throw up. It got a little better the fifth time around and today the fear is still very much there.  I am just better at recognizing my own patterns and have had more reps getting past them.

My brain now has more proof that I can do hard things. But, I still tell myself over and over again before any pitch that “I can do hard things”. It’s my screensaver. It’s written on sticky notes in my office. It is my mantra heading into 2026.

Courage grows by doing it scared, over and over, until you trust yourself to handle whatever comes next. Every successful founder you admire was terrified too. They just decided to do it anyway.

3. Find a real human who has courageously done the thing you want to do. The most powerful lesson in all of this is that courage is contagious. Being around other courageous humans will make you, by default, more courageous. If no one in your circle has done what you're doing, your subconscious may tell you it's too far-fetched.

For me, what helped was connecting one-on-one with founders who built businesses from zero to millions from scratch. Not those who managed businesses they inherited or ran big corporate businesses, but people who took an idea from zero to one, ran with it, and grew it into a seven, eight, or nine figure business.

Speaking with founders that lived through the early-stage startup pains before launching Executiv gave me the courage I needed to take the leap.

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“Courage starts with showing up and letting ourselves be seen.”

Brené Brown