Why Entrepreneurs Succeed by Leveling Up as Leaders

"Wow. I feel like I am starting to really get it... to understand leadership."

This is how I have been feeling lately.
I'm rising, launching several new companies, and also seeing my existing companies evolve.

But what is interesting is that this is not being accomplished by some brute force work ethic on my side...

My businesses are rising because I'm finally understanding what it means to be a great leader.

And in this "epiphany" of leadership, I feel like I have unlocked an entirely new chapter of my entrepreneurial career that is about to be much bigger and better.

In this article, I try to capture this "epiphany" in writing, and teach you what I am learning.

What entrepreneurs do

There is some quote that goes along the lines of:

"Entrepreneurs take resources at one level of value, and figure out how to sell those back into the market at a higher level of value."

At its core, this is what most of business is.

An agency recruits talent and becomes efficient, and then they resell their talent’s labor at a higher cost.
A manufacturing plant takes raw materials, turns them into something, and then sells them at a higher cost.
A consulting firm takes knowledge that they learn in the market, and resells that at a higher cost than they paid to learn it.

This is what entrepreneurs do.
They figure out how to add value.

The more value they add into the world, the more that comes back to them in terms of monetary reward.

But there is a challenge... a roadblock for many entrepreneurs...

It is the roadblock of doing it themselves...

Entrepreneurs are hustlers

As an entrepreneur, you got to where you are most likely due to an insane work ethic, resilience, and large amounts of personal growth.

When a challenge presents itself you tackle that challenge.
There is nothing you can't overcome.

Pulling all nighters?
Working weekends?

You are willing to sacrifice whatever it takes to build your business.

This is what entrepreneurs do, and what makes us succeed...

Garrett J. White has once referred to this as "The Hustler" that exists within all of us as entrepreneurs.

Why entrepreneurs struggle to lead

While being a hustler is a great thing, it also presents challenges.

At some point, there are only so many hours in the day.
At some point, you can't keep creating more value unless you get others involved.

Yet entrepreneurs struggle with this... they operate from this place of intense vigor and work ethic... and so as soon as they involve someone else, it often leads to frustration, slowness, and struggle.

Others don't operate at our level... so we get frustrated.

We just want to do it ourselves.

When in reality, we know we need to grow as leaders and get better at guiding others.

We need to become CEOs.
But we are stuck still being a hustler.

The fundamental shift that entrepreneurs need to make

As entrepreneurs, we have been trained to "Do work, get result."
That works as long as you are doing the work.

But you know what is even more rewarding, and has unlimited upside potential?

"Coach others to do the work, get result"

Guiding and coaching team members to achieve a result leads to far more exponential impact than you could ever have by doing the work yourself.

You can't do it all. But you can coach and guide great people to do it all for you.

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The approach described in this article, shown as a visual guide.

At first, this may sound odd. "Have them do it all for you." But in that statement is massive power.

Elevate your people resources to higher value

This brings me to my epiphany...

Remember our statement about entrepreneurship.

"Entrepreneurs take resources at one level of value, and figure out how to sell those back into the market at a higher level of value."

Now let's apply that to leadership and humans.

"Entrepreneurs take people who are contributing at one level of value, and figure out how to help them contribute at a higher level of value."

Re-read that... slow down and re-read that.

There is gold in that statement!

Let me explain with a story...

Example: Elevating people within Lead Cookie

About 1.5 years ago, I came across two super talented guys named Isaac Marsh and Jeff Doehler. These guys had a small outbound agency that was doing great work.

They were super smart, had great attitudes, and produced awesome results for their clients.

At any given point, Isaac and Jeff were running 3-6 client campaigns at a time.

They were doing ok, and making a living. But they were struggling with the entrepreneurial side of running the business and understanding where to go.

I was wanting to expand Lead Cookie (opens in a new tab), so we ended up doing an odd sort of acqui-hire relationship with them and two VAs they were working with.

When they joined us, they were contributing value to 3-6 clients at a time...

Today, they are contributing value to 50-60 clients at a time....

There were multiple things that had to happen for this increase in value to occur.

First, as a company we had systems, teams, and processes that enabled them to do what they did best, but faster and more efficiently.

Second, we had more opportunities due to our marketing so they were able to support more opportunities than they had been able to attract alone.

But Third, and MOST IMPORTANT...

Through joining our organization, Isaac and Jeff learned and evolved as individuals and leaders which enabled them to contribute at a higher level.

This is how leadership really works in entrepreneurship, you find great people and figure out how to elevate them to a position where they are contributing to the world through their unique strengths.

Example: Elevating my lead Content Strategist

My COO for Lead Cookie was once an events manager for the BBB. Today he runs a team of 20+ team members at Lead Cookie.

One of our account strategists at Lead Cookie had no experience in outbound when we brought him on, just a great attitude. We've trained and coached him into becoming one of the best outbound strategists in the world.

Your role as an entrepreneur is to find great people, and help them contribute more value

This is entrepreneurship and leadership combined.

You find people with great attitudes who are under leveraged.
You move them into positions of greater contribution and value.

This happens in two ways.

1. Business Strategy
2. Leadership / Coaching

Business Strategy

At its most basic level, entrepreneurs hire people and capture value on the work they do by selling it at a higher price point in the market.

So a sound strategy is in place for this to work... BUT it comes with caveats.

Business strategy alone won't take you far.

For example, I know an entrepreneur with a great business model... but there is one problem.
The guy is a total asshole.
On a call he once said to me "How do you get your VAs to stick around? We can't keep anyone for more than 2-3 months."
I was too polite in the moment, but I should have said "That's because you’re an ass and no one likes you."

So strategy alone can create value... but it will only take you so far.

Leadership & Coaching is like rocket fuel for leverage

As Peter Drucker once said "Culture eats strategy for breakfast."

Yes, your business strategy must make sense. But after that, coaching and leading your team is the real accelerator.

With strategy, you just are trying to hire and place people in roles.
But with leadership, you are also working the emotional side.
You are taking talented team members, and investing in them and helping elevate them to new levels of contribution.

For example, if I just focused on strategy, Isaac and Jeff from Lead Cookie would have been stuck as doers of the work...
With leadership and coaching, they have evolved to running Lead Cookie's sales and strategy departments.

If I had just focused on strategy, Jess would just be at the level of project manager.
But with leadership and coaching, she has evolved into a COO for the company and our lead strategist.

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When you invest in your team as a coach and leader, you level them up, and they contribute more value to the world.

How can you elevate more people to contributing higher value?

"Entrepreneurs take people who are contributing at one level of value, and figure out how to help them contribute at a higher level of value."

When you have this lens, you begin to look at the whole world differently. You see someone who has talent, and in them you see potential. You see a bigger future for them and how they can contribute more.

Then you help them close that gap, and guide them to a place of greater contribution.

This leads to exponential leadership growth, and business growth.

But here is the thing...

Leadership is slow.

Leading others is slower than "hustling"... at first.

Remember our conversation about "The Hustler"?

Well here is the thing. As you make this transition, you are going to be frustrated at times. Something that you may have tackled in a weekend might take someone else 2-3 weeks.

People will hit road blocks... mental barriers... skillset barriers...

And this can be frustrating because you want to go fast...

Leading is faster at scale

But here is the thing...

You can "hustle" on one task at a time.
You can "lead" countless other projects at a time.

So when you start leading your first person, you get a bit frustrated. You just want to do it yourself.

But eventually once you are leading 5-10 others to achieve things you otherwise would have done yourself... then you see the exponential power.

Then you realize "I can't jump into the weeds. I can't do this all. It's simply not possible."

And as a result, you learn to lead.
You learn to guide others.

You accept a slower pace on individual projects, because you know the pace of business speeds up when you lead many projects at the same time.

Recommended reading to solidify this mindset shift

This epiphany has been brought on by some reading I've been doing lately. A lot of which comes from Strategic Coach. Here are two resources I recommend and why.

Who Not How by Dan Sullivan (opens in a new tab) (Free at this link) - This book and interview series hit me like a ton of bricks.

The biggest takeaway is that when you want to achieve something, don't ask "How do I achieve this?" ask "Who can help me achieve this?"

One of my favorite questions of the book is "How do I accomplish this goal while doing absolutely nothing?" This question forces you to think as a leader that enables others to accomplish the goals you want to achieve in life.

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Unique Ability (opens in a new tab) - I read this book years ago and it had a profound impact on me personally understanding myself and my strengths. At this point, I have had several of my team members work through this book and exercises themselves.

But beyond the actual exercises, it is understanding the concepts that each individual has a certain set of strengths that are unique to them.

As a leader and a coach, it is my role to help people get into roles and positions where they are using their strengths.

Elevating as a leader is essential to elevating as an entrepreneur

I used to think all of this hype around "leadership" was a bunch of fluffy garbage. Now I get it.

If you want to grow your company, you must evolve as a leader.
If you want to grow in your contribution to the world, you must evolve as a leader.

As one person, you can only do so much.
But as a leader you can create exponential impact and value.

And one final word...

Rising as a leader is fun!
It's rewarding.
You see people’s lives change.
You make more money.
And they make more money.

It's freaking awesome.
So step up your game.

Level up your leadership.
It's the bottleneck holding you back as an entrepreneur.

Looking back in May 2025

In my May 2025 conversation with my former adviser Alex McClafferty (opens in a new tab), he asked whether it had taken me time to trust people after coming from a solo background into building a team. It had. I managed far too closely, and letting go was hard.

I went through an exercise: give someone a clear outcome, "get really good at defining like what success is", then ask what support they need, have them check in with me, and let them get on with it.

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In Pew’s February 2023 survey, workers receiving frequent feedback were more satisfied with the amount they received. The sample excludes self-employed workers. This association does not establish that more feedback caused the higher satisfaction.pewresearch.org (opens in a new tab)

In the same conversation, I said that "there's some level of competency you need in all aspects of the business to be able to hire someone effectively." I went through several painful finance hires, and something similar in operations, before I learned those functions well enough myself. My next operations hire worked because I knew exactly what I was looking for.

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Jake’s historical account, summarized from this article. These results describe his experience and are not a performance forecast.