Stephen Scoggins is a serial entrepreneur, author, coach, and host of the Build podcast. Having once started his business while sleeping in his car, Stephen built his construction company from the ground up and successfully exited in late 2023, selling at just under nine figures. Now, he invests in other entrepreneurs, mentors high-performing founders, and speaks across stages nationwide, sharing practical wisdom on scaling, exits, and personal transformation.

On this episode we talk about:

How Stephen went from homelessness to building and selling a near nine-figure company

The lessons learned from exiting a business: why you should always build as if you plan to sell—even if you never do

What buyers really want: systems, predictable cash flow, culture, and efficient operations

The importance of restructuring, optimizing, and “going back through with a fine-tooth comb” before an exit

Stephen’s new focus on family office investing, real estate, equity stakes, and founder mentorship

Why a year-long entrepreneur “test period” is Stephen’s preferred way to find investible founders

The five hidden enemies of entrepreneurs—impatience, arrogance, ignorance, fear, and insecurity—and how conquering them changes the game

How to discern between arrogance and confidence, and how confidence comes from consistency, not credentials

Tips on hiring for executive roles, including how to vet candidates even if they’re smarter or more credentialed than you

The value of coaching and mentorship at every stage—even after an exit

Practical steps for employees and early-stage entrepreneurs to identify their superpowers, solve real problems, and launch a business with little capital

Top 3 Takeaways

Build to Sell, Even If You Don’t: Always design your business with predictable systems, clear financials, and a scalable team—whether or not you ever plan to exit.

Self-Awareness is the Real Secret: The most dangerous enemies in business are internal—impatience, fear, arrogance, ignorance, and insecurity. Master yourself to master your business.

Mentorship Multiplies Success and Saves Pain: Investing in coaches and mentors is the cheapest and most powerful way to accelerate growth and avoid costly mistakes.

Notable Quotes

“If you’ll focus on building as if you’re going to sell, you’ll end up with the kind of company buyers—and you—actually want.”

“Arrogance is self-seeking. Humble confidence comes from serving others and showing up with consistency.”

“Most of my painful lessons, including losing over a million dollars to embezzlement, could have been avoided by listening to my mentors sooner.”

Connect with Stephen Scoggins:

Website: stephenscoggins.com

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