Building Bourbon & Business: From Risk and Rejection to Winning Awards

How Resilience, Relationships, and a Passion for Community Built The Winter Park Distilling Company and a Life Well-Lived

 

What does it take to become a successful entrepreneur? If you dream about quitting corporate life for something more meaningful -- you’re not alone. But as Paul Twyford, cofounder of Winter Park Distilling Company, reveals on the B Student podcast, entrepreneurship is about far more than just chasing the next big idea. It’s about grit, adaptability, and investing in people and community -- even when it doesn’t show up in a spreadsheet.

 

Starting with Grit, Not Glamour

Before he was known for crafting award-winning bourbon in Central Florida, Twyford’s entrepreneurial journey began in an unexpected place: the world of dry cleaning. With little money and zero experience, Twyford spotted a simple problem -- lack of convenience in dry cleaning pickup and delivery -- and decided to solve it. Armed with laundry bags, flyers, and a van he bought on credit, he hit the streets, knocking on doors and facing rejection nine times out of ten.

His story challenges the romanticized notions of entrepreneurship. “People have a problem with authority, and they think, ‘I’m going to be my own boss, and it’s going to be glamorous’ -- and then they get to the part about nine doors out of 10 slamming in their face,” Twyford shares. What kept him going was pure determination and the refusal to become just another cog in the corporate wheel.

 

The Takeaway:

Successful entrepreneurs aren’t just idea people -- they must be resilient enough to handle relentless rejection and humble enough to start wherever opportunity presents itself, no matter how unglamorous.

 

Embracing the Unknown – And Imperfect Action

A recurring theme in Twyford’s career is his willingness to leap before he feels ready. After selling the dry cleaning business, he dove into commercial weatherproofing -- again, with zero expertise. His conviction? You don’t need to be an expert before you begin. “Most of my career I haven’t had any clue what I was doing. But I didn’t let that stand in the way,” he says.

Twyford likens true entrepreneurship to “jumping off a cliff with the firm belief you’ll build an airplane before you hit the ground.” He emphasizes that risk tolerance and the ability to take imperfect action are crucial. Every new venture -- like launching Winter Park Distilling -- was approached with calculated optimism and a faith that new skills and solutions would emerge along the way.

The Takeaway:

Don’t wait until you feel ready. The willingness to start, adapt, and learn as you go is a defining trait of entrepreneurial success.

 

The Power of Saying Yes and Serving Your Community

If there’s a “cheat code” to building a rewarding life and career, Twyford believes it’s simple: say yes, especially early on. Many entrepreneurs calculate the ROI of every community involvement, but he’s found that investing in relationships -- through board service, chamber involvement, and volunteering -- pays off in unpredictable yet invaluable ways.

 

“You opt in and pour yourself into your community, trusting the relationships you build are going to be good for your life, whether for business or friendship,” he explains. For Twyford, playing the “long game” with people has been more beneficial than any marketing blitz. His people-first approach has forged a loyal team and a supportive network that consistently comes through, whether or not there’s an immediate business benefit.

 

The Takeaway:

Community involvement might not provide instant or easily traceable returns, but the depth of connection and support you gain is priceless -- and often becomes your biggest asset.

 

Crafting a Unique Product -- and a Legacy

With Winter Park Distilling Company, Twyford brought Florida’s first bourbon to market. Unlike mass-produced spirits, his distillery focuses on small batches and local ingredients -- like Florida corn -- emphasizing quality over quantity. While marketing might get your product noticed, it’s the “juice in the bottle” and genuine story behind it that earns lasting loyalty and national awards. The company's Bear Gully Classic Reserve and Bear Gully Classic Bonfire Bourbon were the first award-winning bourbons in the state of Florida. Winter Park Distilling has earned multiple awards, including a silver medal at the prestigious San Francisco World Spirits Competition.

 

But for Twyford, the true B-side of his record isn’t entrepreneurship or bourbon -- it’s the relationships he’s built along the way. “If you put a gun to my head and asked what’s the most important thing in your life, it’s the people,” he says.

 

The Takeaway:

Stay focused on quality, authenticity and the people you serve and work with. When you do, success -- both in business and life --  becomes far more attainable and rewarding.

 

Paul Twyford’s story is a masterclass in perseverance, people skills and the courage to say yes, even when the outcome isn’t guaranteed. His journey from door-to-door dry cleaning to award-winning bourbon proves that business -- and life -- are best built on a foundation of resilience, community, and a willingness to get a little uncomfortable. Whether you’re a seasoned business owner or an aspiring entrepreneur, these lessons from the B Student podcast are worth taking to heart the next time you find yourself at a crossroads.