We recently had the chance to connect with Sam Stilley and have shared our conversation below.
Sam, a huge thanks to you for investing the time to share your wisdom with those who are seeking it. We think it’s so important for us to share stories with our neighbors, friends and community because knowledge multiples when we share with each other. Let’s jump in: What do you think others are secretly struggling with—but never say?
A lot of entrepreneurs are quietly wrestling with mental health battles no one talks about. There’s this constant pressure to stay sharp, lead with confidence, and always have the answers. But behind the scenes, it’s a rollercoaster. One day you’re on top of the world, the next you’re questioning everything, your decisions, your direction, even your worth.
What people don’t realize is how lonely it can get. Even when you’re surrounded by a team or in a room full of people, you feel like no one truly understands the weight you’re carrying. You start suppressing emotions just to stay functional. And over time, that emotional detachment shows up in your relationships—less patience, less empathy—not because you don’t care, but because you’re stretched thin trying to keep everything afloat.
Most founders won’t say it out loud. They’re afraid it might shake investor confidence, make the team uneasy, or give off the impression that they’re slipping. But the truth is, a lot of them are just pushing through quietly, hoping they don’t break before they make it.
Being an entrepreneur is often glamorized, but what’s rarely acknowledged is how much it can take from you if you don’t have the right support or space to breathe. And sometimes, just admitting that you’re struggling takes more courage than launching any company ever will.
Can you briefly introduce yourself and share what makes you or your brand unique?
My name is Sam Stilley, and I’m a self-made entrepreneur and investor based in Houston, Texas. I’m the co-owner of Amstill Roofing, the largest residential retail re-roofing company in Houston. We built our reputation on integrity and delivering results without shortcuts. I’m also the founder of The Forge Hobbies and Games, which in 2024 became the University of Houston’s fastest-growing alumni-owned business in the world, a passion project that turned into a thriving retail and community hub for tabletop gamers, driving over 30,000 transactions a year in-store.
Beyond the businesses I operate, I invest in small-sized companies with strong fundamentals and clear paths to scale. I’m also a commercial real estate investor focused on assets that offer long-term cash flow and strategic growth potential. Whether I’m expanding a brand or acquiring a property, my approach stays rooted in operational discipline, values-first leadership, and a relentless work ethic.
What makes my journey unique is that I built everything from the ground up. No handouts. No shortcuts. Just faith, grit, and a clear vision for what I wanted to create. Today, I’m focused on scaling Amstill Roofing further, creating success in new ventures centered around artificial intelligence, empowering the growth of strong teams, and investing in opportunities that align with what matters most to my core values and a legacy built the right way.
Okay, so here’s a deep one: Who saw you clearly before you could see yourself?
My father. He’s always believed in me, even in the moments when I couldn’t see the path forward. At one point, we were broke, and that’s when he trusted me the most. He put his future, our company, and everything we had on the line because he believed in what I was capable of becoming.
From a very young age, he poured into me as both a mentor and a father, always guiding me with wisdom, discipline, and encouragement. But more than anything, he built me on the foundation of faith; raising me to know and follow Jesus Christ as my Lord and Savior. That foundation shaped the man I became and gave me the strength to rise even when the odds were against me.
Was there ever a time you almost gave up?
Absolutely. I was around 25 or 26 when I was hit with a $6.5 million lawsuit. At the time, that number far exceeded my net worth, the value of my company, and even my father’s combined. It stemmed from a catastrophic incident at a commercial property, and it came down to just my word against the other party’s. There were no easy outs; only stress, fear, and the weight of a situation that felt impossible.
For over a year, I carried that burden through countless sleepless nights, hundreds of thousands in legal fees, and the constant fear that everything my father and I had worked for could be destroyed. The pressure was suffocating. I dreaded each new day, and the uncertainty stretched into months that felt like years. It was the most gut-wrenching experience of my life.
But by the grace of God, I made it through. I was eventually able to provide enough evidence to prove I hadn’t caused the issue. Around age 27, I was finally able to walk away from it, changed forever by the experience, but not broken. That season taught me what it truly means to stand in the fire, hold your integrity, and trust in something bigger than yourself.
I think our readers would appreciate hearing more about your values and what you think matters in life and career, etc. So our next question is along those lines. What’s a belief or project you’re committed to, no matter how long it takes?
I’m fully committed to building a life rooted in faith, discipline, and long-term vision. At the core of that is my belief in putting myself and one day, my future family on a foundation grounded in Christianity. That means raising my future children with the highest probability of success: spiritually, emotionally, and practically.
Everything I’m working toward now—the sacrifices, the long hours, the risks—is aimed at creating generational stability. I’m committed to securing financial freedom, building a healthy lifestyle, and setting up a life where my future family is deeply cared for, protected, and positioned to thrive. I want to honor them not just with what I’ve built, but with the man I chose to become in the process. I may not have them yet, but they’re already the reason I don’t quit.
Before we go, we’d love to hear your thoughts on some longer-run, legacy type questions. What is the story you hope people tell about you when you’re gone?
I don’t want to be remembered for my business success, my leadership, or my ability to endure and achieve. Those things fade. There will always be someone richer, more accomplished, or more recognized. What I truly hope people remember is how much I laughed. How much I loved to joke around, be playful, and bring out the kid in others.
I want to be remembered for my spirit, who I was at my core. Not the cars, not the houses, not the accolades. I want people to say, “He could make anyone smile.” Because that’s what matters most. The world will try to steal your joy and dull your spirit in the name of success. But I believe we’re meant to hold on to the fun, the laughter, and that childlike wonder no matter how far we go.
At the end of the day, everything else is just noise. Life is short. Have fun. Stay true to yourself. And never let the kid inside you die.
Contact Info:
- Website: https://www.amstillroofing.com
- Instagram: @samstilley
- Facebook: https://www.facebook.com/sam.stilley
Image Credits
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