From high school dropout to award-winning entrepreneur, Stephen Santi, Founder and CEO of Auto Mate Insurance, has defied the odds and redefined success on his own terms. His journey is a powerful reminder that “nothing is impossible” when determination meets purpose. Today, he not only leads one of the most innovative insurance companies in the market but also dedicates himself to inspiring and empowering others to chase their dreams—no matter how far-fetched they may seem.

“Some of the most rewarding moments in my life come from hearing that I’ve inspired someone to take a leap toward their dreams,” Stephen shares. “If I can help others reach their goals—even if it takes an extra step—I consider that a true win.”

Rising Against All Odds

Stephen’s path to success wasn’t paved—it was carved through grit, setbacks, and self-belief.
“I’ve never thrived being told to do low-impact tasks. I’ve always wanted to make a real difference—and that meant taking risks,” he reflects. “At times, I’ve stepped out onto platforms that didn’t exist yet. Sometimes I landed; other times, I fell hard. But every failure taught me how to prepare better for the next step.”

For Stephen, success isn’t measured in dollars—it’s about impact. Along his journey, he met individuals who challenged conventional thinking and equipped him with the tools to build his dream life. Through Auto Mate Insurance, he’s now doing the same for others—empowering clients to take control of their insurance needs with transparency, ease, and confidence.

Turning Trials into Triumphs

Stephen’s entrepreneurial journey has been anything but smooth.

“My first business looked great on paper but left me mentally and financially drained. My second was taken from me at the height of its success,” he admits. “But without those hard lessons, I wouldn’t be where I am today. Auto Mate is my third startup—and a reminder that failure is not the end.”

He believes that growth is forged in adversity, and success comes to those who stay adaptable, work relentlessly, and continue to learn.

Reinventing Insurance with Auto Mate

Auto Mate Insurance offers home, auto, and business insurance through a broker model with access to 70+ carrier options. With a 4.9-star Google rating, Auto Mate is trusted by clients and even fellow agents who turn to them when they need expert solutions.

“Our mission is simple—make insurance better, easier, and more accessible,” Stephen explains. “We provide free education, professional guidance, and the best value in the market.”

To achieve this, Auto Mate has invested heavily in digital infrastructure and automation, enabling lightning-fast service and 10x the options of a traditional independent agent.

Disrupting the Industry Through Access and Innovation

At the heart of Auto Mate’s success is its commitment to accessibility and availability. By partnering with over 70 insurance providers, the company ensures clients get precisely what they need—regardless of complexity.

Moreover, their franchise and independent agent program is designed to help agents thrive.

“Having experienced the early pitfalls of the industry, I wanted to give others a better way to go independent—complete with support, connections, and resources. We’re very proud of that,” Stephen says.

Looking ahead, the company is investing further in digital tools and AI-driven customer support, including 24/7 assistance, automated messaging, and live chat—tools that proved crucial during the COVID-19 pandemic.

Leading with Vision

As CEO, Stephen is the driving force behind Auto Mate’s growth and innovation. His role spans everything from strategic leadership to hands-on collaboration with agents, vendors, and major clients.

“Every day is different, and I thrive in that. Whether I’m solving problems, onboarding big accounts, or mentoring agents—I love what I do,” he shares.

His most treasured accolades? The words of those he’s inspired—friends and former colleagues who’ve started their own ventures or dared to dream bigger because of his example.

Balance, Team Culture, and Personal Growth

Stephen believes strongly in the power of balance.

“When I’m happy internally, it shows in my work and relationships,” he says.

He carves out personal time to reflect, recharge, and grow—habits he encourages within his team. Auto Mate’s culture promotes goal-setting, recognition, and team input, creating a motivated and connected workforce.

“We hand out awards, listen to our team, and support their individual growth. When they thrive, our clients do too.”

Building a Legacy

Stephen’s long-term vision goes beyond business. His personal mission is to found a nonprofit that teaches real-world skills to underserved communities—giving people the knowledge and tools they need to change their lives.

“I believe in teaching people to fish. If I can help someone learn a skill that changes their life, that’s success,” he concludes.

Through Auto Mate and beyond, Stephen Santi is rewriting the rules—not just for insurance, but for what’s possible when heart, hustle, and hope come together.

Company Name: Auto Mate Insurance
Founder and CEO: Stephen Santi