How Shawn Rider Built Freedom Through Real Estate, Mentorship, and Money Stewardship

You don’t need to be a billionaire to build a free and fulfilling life. You need clarity, stewardship, and a system that supports your priorities. That’s exactly what Shawn Rider has built, and in this episode of The Balanced CEO, we unpack how.

I sat down with Shawn after day one of Tactical Empire and we got straight into the real talk. We covered how he went from a high school teacher grinding side hustles, to a leader running three businesses and a real estate portfolio on just ten intentional hours per week.

Shawn’s story isn’t about luck. It’s about choosing the long game. It’s about building with intention, investing in yourself, and learning how to block your time, grow through mentorship, and master your money.

From Teaching to Ownership: Why the Hustle Had a Purpose

Shawn grew up watching his parents work hard but struggle for time. That stuck with him. He realized early that clocking in for someone else would always come with limits. So, he took the leap and became a teacher, which gave him the structure to build something on the side.

He dove into entrepreneurship while still in the classroom. He watched Gary Vee. He learned from gym mentors. He stacked small wins and spent years working nights and weekends. The goal? Build enough momentum to break free—and he did.

The Power of the Four Fs

Through Tactical Empire, Shawn now mentors other men through what he calls the Four Fs: family, fitness, finance, and freedom. That’s where real leadership begins. You lead yourself. Then you lead your family. And only then do you earn the right to lead a team, a company, or a community.

What sets Shawn apart is how he’s structured his life around these priorities. He’s not chasing hustle for hustle’s sake. He’s not interested in vanity metrics. He’s building a legacy, and he’s doing it through systems that allow his time to multiply, not just be spent.

How He Runs Three Businesses in 10 Hours a Week

Yes, you read that right. Shawn operates three businesses—including a new gym, a mentorship company, and a growing real estate portfolio—with about ten hours of weekly focused work.

How? Through extreme clarity. He time blocks his mornings around rest, movement, family, and reflection. He doesn’t start work until 11 a.m. because he knows when he performs best. He’s created margin on purpose.

He also knows what “enough” looks like. He’s tasted overwork and burnout. He’s tested the limits of too little and too much. Now, he’s found the pace that allows him to keep building without burning out.

Infinite Banking and Real Estate: Freedom Built the Smart Way

We got into the weeds about money strategy. Shawn’s a practitioner of infinite banking, using high cash-value life insurance to store capital and leverage it for investments. This gives him guaranteed growth, access to capital, and long-term protection.

From there, he puts that money into real estate—not just randomly, but through smart partnerships where he brings capital, and the operators bring the knowledge and time. This is how he multiplies wealth without multiplying stress.

As he puts it, “Every dollar becomes a little soldier. And I want those dollars recruiting more dollars while I keep the main thing the main thing.”

Being a Steward, Not Just an Earner

One of the strongest takeaways from this episode is Shawn’s mindset around money. In his 20s, he partied on a budget. He lived within his means, built good habits, and stayed focused on delayed gratification. That discipline is what allows him now to live a life of freedom, generosity, and purpose.

It’s not about never enjoying yourself. It’s about choosing when, how, and why.

Keep the Main Thing the Main Thing

Success doesn’t mean constant growth at all costs. For Shawn, success looks like being present at soccer games, taking intentional trips with his wife and kids, and having margin in his day to think, reflect, and lead. He’s still building. But he’s building smart, not scared.

This episode is a masterclass on how to live with purpose, build real freedom, and steward the blessings you’ve worked for.

Listen to the full episode now on YouTube, Spotify, and Apple Podcasts.

If this episode resonated with you and you're looking for something to help you reflect and realign, you might enjoy my book Labels to Legacy. It’s a practical and personal guide for anyone ready to build with intention.

If you’re in a season where you’re growing something and want a bit more clarity or support, feel free to reach out. I work with leaders who want to keep things simple and meaningful.