Why Beyond The Peak

From High Performance to Founding with Purpose

There’s a question I hear often from founders and entrepreneurs. Sometimes it comes out in words. Other times, it just lingers quietly behind the scenes of their success:

“Is this it?”

It’s not a complaint. It’s a confession.

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And it doesn’t come from people who are failing. It comes from those who are doing well on paper. They’ve built something. They’ve crossed a finish line or two. And still—deep down, they feel the quiet ache of disconnection.

Stephen Covey says it so well.

"You don’t want to climb the ladder of success only to find it’s leaning against the wrong wall."
—Stephen Covey

I know this feeling well. Not because I studied it. Because I lived it.

My Story: From the Tennis Court to the Entrepreneurial Journey

I started in sport—coaching athletes pushing towards being the top in the world. For over a decade, I was immersed in high-performance sports where pressure, discipline, and resilience shaped daily life. But along the way, I noticed something:

Performance doesn’t guarantee peace.

Many of the athletes I worked with were chasing excellence, but at great personal cost. Identity became tied to results. Confidence fluctuated with outcomes. Wins didn’t always lead to joy.

Then came my own transition into entrepreneurship—and with it, my biggest failure. A co-founder betrayal cost me my life savings. It happened right after the birth of our second child. We had nothing. It was humbling. Crushing. And somehow, liberating.

Because that fall stripped away what wasn’t real.

I joined a friend’s small business. Rebuilt slowly. Earned an MBA. Launched a business on behalf of an investor, spearheaded commercial projects (new startups) for a university. Eventually, my journey brought me to where I now coach, advise, and help execute founders and entrepreneurs—across tech startups, bootstrapped ventures, and small and medium-sized businesses. And after thousands of conversations with entrepreneurs, I’ve realized something:

We all feel it.

The tug toward something deeper.

Not just a better business. A better life.

Today, a decade after that season of loss and reinvention, my eldest son is pursuing his own Olympic dream in swimming. At just 12 years old, he’s setting national-level times in Canada—and yet, even at that age, the need to establish identity outside of performance is real.

Injuries happen. Sickness comes. Priorities change. What happens if it all ends tomorrow?

“A gold medal is a wonderful thing, but if you're not enough without it, you'll never be enough with it.”
—Eric Liddell, Olympic champion and Christian athlete

Finding a way to strive for excellence without wrapping your entire worth around your output is one of the hardest tensions we face—whether you’re an athlete, an entrepreneur, or a parent trying to hold space for both.

And this is where best practices in sport psychology begin to mirror what the healthiest entrepreneurs eventually realize:

• Mindset can make or break you. It needs to be trained, not assumed.
• Recovery is part of progress - It is juts as important as the time you are putting in the hard work, if not more important.
• Who you are is bigger than what you do.

These aren’t just theories—they’re survival principles.

What This Newsletter Is About

This isn’t about business hacks or industry trends. There are more than enough out there. And I want to be clear, I am not saying those are not important. What I have realized though, without focusing on what we will be chatting about here, nothing else really matters in the bigger scheme of things.

This is about you, the journey you are on, and the story of your life being written.

The human behind the company.

The leader beneath the LinkedIn title.

It’s about:

• Identity and integrity in a world obsessed with outcomes
• Building rhythms that fuel rather than drain
• Navigating seasons of burnout, boredom, or reinvention
• Learning to lead yourself before leading others
• Creating ventures that serve others and society, not just extract value
• Choosing stewardship over scale, service over self-interest, and purpose over platform

"Success is when those who know you best love and respect you the most."
—John Maxwell

It’s also about building from a grounded, human-centered place—where creativity is used to renew rather than exploit, where leadership is practiced with humility, and where business becomes a vehicle for sustainable impact.

This is a space for reflection, renewal, and real talk.
Because you weren’t made to climb ladders forever. You were made to live with purpose.

Whether you’re scaling a tech product, running a regional service business, or growing a community-centered enterprise—this space is for you.

“Don’t aim to be the best in the world. Aim to be the best for the world.”
—Ben Chestnut, Mailchimp co-founder

I am not saying there is anything wrong with being the best in the world, what I am saying is…

Roger Federer never knew whether he will become the best and be the GOAT, but in being the best for Tennis, he became the best tennis player the world has ever seen (my biased view, I know it is a battle for who really is the GOAT)

A Line That Grounds Me

One lyric that continues to shape my thinking comes from the song “Gratitude” by Brandon Lake:

"Come on, my soul / Oh, don’t you get shy on me / Lift up your song / ’Cause you’ve got a lion inside of those lungs."

It’s a call to live boldly and use your voice for something greater than yourself. A reminder that even when you're discouraged or unsure, there’s something powerful within you—worth expressing, worth building from, worth sharing.

It’s about building in a way that outlasts applause. Living with conviction, not just ambition. Doing the hard work of becoming someone worth following—regardless of outcomes.

Why I’m Writing

I’m not here to teach or coach from a pedestal. I’m here to walk with you, as a peer, as a friend. To ask better questions. To reflect, challenge, and encourage.

Because I believe entrepreneurship can be meaningful.
I believe ambition and wholeness can coexist.
And I believe your business can become the most honest expression of your values.

Let’s build that kind of business. And that kind of life.
Together.

A Question for You to Reflect On

If you stopped building tomorrow—
If the market shifted, or your product failed, or your title disappeared—

Who would you be without your business?

Who will be around you to share your days if the business was not there?

And more importantly:

Do you like the answer?

Until next time,
Jaco

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