We caught up with the brilliant and insightful A.j. Weinzettel a few weeks ago and have shared our conversation below.

A.J., looking forward to hearing all of your stories today. How did you come up with the idea for your business?

In the summer of 2019, I fell head over heels into the world of wine. It started with a passion project—a weekly newsletter where I’d dive deep into the story of one winery each week. These weren’t just surface-level write-ups; they were longform features, 1,500 to 2,500 words, peeling back the layers of these incredible people and their dreams. Wineries, I discovered, aren’t just businesses—they’re personal journeys. They’re people raising families, nurturing vineyards, and pouring their hearts into every bottle. I was hooked.

Then came 2020, and everything changed. When the pandemic hit, wineries had to quickly adapt, shifting from walk-in tastings to reservations. It was a massive pivot, and for a moment, I was genuinely excited to see technology stepping in to support this industry I’d grown to love. But as someone who’s been in tech since 1993, I couldn’t resist taking a closer look at the system everyone was flocking to.

What I found was disappointing. This platform wasn’t built for wineries; it was a restaurant reservation system. The result? A difficult user experience that didn’t serve the unique needs of wineries. Worse yet, it came with a hefty price tag—one that made it inaccessible for many boutique wineries, the very places whose stories had inspired me in the first place.

I couldn’t shake the thought: wineries deserve better. These are businesses built on hospitality, on making every guest feel like family. Their reservation platform should enhance that experience, not add frustration. And so, the idea for Block 55 was born.

I set out to create a reservation platform designed exclusively for wineries. Not restaurants. Just wineries. My goal was simple: to build a tool that’s intuitive, affordable, and elevates their digital hospitality. Block 55 isn’t just about taking reservations—it’s about helping wineries tell their stories, foster connections, and grow their businesses without breaking the bank.

What got me most excited was the opportunity to solve a problem no one else was tackling with the care it deserved. Wineries don’t just need a reservation system—they need a partner that understands their industry, their challenges, and their guests. Knowing I could offer that made this endeavor feel not just worthwhile, but necessary.

A.J., before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

I’m A.J. Weinzettel, and my journey has been one of passion, purpose, and innovation. My professional roots are in technology—I’ve been in the industry since 1993—but my heart has always been drawn to storytelling and connection. That passion led me to explore the world of wine in 2019 when I launched a weekly newsletter featuring longform stories about wineries. Each week, I shared 1,500 to 2,500 words about the incredible people behind the wines—their dreams, struggles, and triumphs. It wasn’t just about the wine; it was about the heart and soul poured into every bottle.

Then, in 2020, the pandemic turned the wine industry upside down. Wineries, traditionally known for their walk-in tastings, had to pivot overnight to a reservation-based model. While I was initially thrilled to see technology playing a larger role in the wine world, I quickly realized the solution many wineries turned to wasn’t built for them. It was a restaurant reservation system awkwardly retrofitted for wineries. The user experience didn’t align with what wineries needed, and the price made it inaccessible for many boutique operations—the very places that captivated me most.

That’s when I decided to bridge the gap. I founded Block 55, a reservation platform designed exclusively for wineries. It’s not just another reservation system—it’s a tool built with wineries in mind. Block 55 simplifies the booking process, enhances digital hospitality, and empowers wineries to tell their unique stories while fostering deeper connections with their guests. What sets us apart is our commitment to affordability, ease of use, and the belief that every winery—no matter its size—deserves a platform that works for them, not against them.

I’m proud to say that Block 55 solves real problems for wineries. It allows them to retain ownership of their customer data, provides seamless integrations with industry-specific tools like Commerce7, VinoShipper and Bottle360, and enables guests to book in seconds. At the core, we’re not just selling software; we’re creating solutions that allow wineries to thrive in an increasingly digital world while preserving the personal touch that makes the wine industry so special.

What I’m most proud of, though, is the impact we’ve had on wineries. Seeing our platform help businesses streamline their operations, grow their revenue, and strengthen their relationships with customers is incredibly rewarding. At the end of the day, Block 55 exists to support the wineries that inspired me in the first place—the ones whose stories I fell in love with and whose success fuels my own passion.

For anyone considering Block 55, I want them to know that we’re more than just a service provider. We’re a partner, invested in helping wineries grow and succeed while preserving what makes them extraordinary.

Are there any books, videos, essays or other resources that have significantly impacted your management and entrepreneurial thinking and philosophy?

Two books that have profoundly impacted my entrepreneurial thinking are This is Marketing by Seth Godin and The War of Art by Steven Pressfield. These books have become cornerstones of my mindset, and I revisit them often—especially during my road cycling sessions. There’s something about the rhythmic nature of cycling, the steady hum of the wheels on the road, that clears my mind and allows the insights from these books to truly sink in.

Seth Godin’s This is Marketing reshaped the way I think about business and connection. It’s not just about selling; it’s about serving. Godin’s idea of finding your “smallest viable audience” and creating something truly remarkable for them has guided how I’ve approached Block 55. I’m not trying to be everything for everyone—I’m focused on being the best for wineries. It’s a lesson in empathy, in deeply understanding your audience, and in building something that resonates on a human level.

On the other hand, Steven Pressfield’s The War of Art is like a battle cry for anyone creating something new. It’s a book about overcoming resistance—the fear, doubt, and distractions that can hold you back from pursuing your work with focus and courage. As an entrepreneur, resistance shows up constantly: self-doubt, the temptation to play it safe, or the fear of failure. Pressfield’s words remind me to push forward, to trust the process, and to commit fully to the work.

What I love most about listening to these books on repeat is how they reveal new insights each time. Depending on where I am in life or in my business, a particular phrase or concept will hit me differently. It’s like they grow with me, offering guidance exactly when I need it.

Cycling has been such an important part of my life—not just for physical health but for mental clarity. When I’m on the road, it’s my time to reflect, to problem-solve, and to soak in the wisdom from these books. The combination of movement, fresh air, and inspiration has sparked some of my best ideas for Block 55.

These books—and those long rides—remind me that building something meaningful is a journey. It takes perseverance, focus, and a willingness to keep showing up, no matter the challenges.

Let’s talk about resilience next – do you have a story you can share with us?

Resilience has been at the heart of my journey with Block 55. When I first started, I was so excited to build a reservation platform for wineries. I poured countless hours into the first iteration, and when it was done, I thought I had something great. But here’s the truth—it sucked. It didn’t meet the needs of wineries the way I envisioned, and deep down, I knew it wasn’t the product I wanted to bring to market.

Trashing that first version was one of the hardest decisions I’ve ever made. It felt like starting over. But looking back, it was also the best decision. I realized that the only way to build something truly valuable was to stop assuming I knew the answers and start listening.

That’s when I shifted my approach. Over the past few years, I’ve engaged with over a hundred wineries, sitting down with owners, managers, and staff to understand their unique challenges. I asked them about their workflows, their frustrations with existing tools, and what their dream reservation system would look like. Those conversations became the foundation of what Block 55 is today—a product built for wineries, by wineries.

The process wasn’t easy. It meant setting aside my ego, staying open to feedback, and being willing to iterate again and again. But that’s what resilience is all about—picking yourself up, learning from the hard moments, and pushing forward with a clearer sense of purpose.

Today, Block 55 isn’t just a reservation platform—it’s a solution that reflects the voices of the wineries it serves. Every feature, every integration, and every design choice was guided by the feedback of real people in the industry. I’m proud to say that Block 55 is more than just a product; it’s a partnership with the wineries that inspired me to create it in the first place.

The experience taught me that resilience isn’t about never failing—it’s about what you do when things don’t go as planned. It’s about having the courage to start over, to listen, and to build something better than you ever imagined.

Contact Info:

• Website: https://block55.app
• Instagram: https://www.instagram.com/block55.app/
• Facebook: Coming Soon
• Linkedin: Coming Soon
• Other: https://bsky.app/profile/block55.bsky.social

  I haven’t expanded my socials very much at this point. February will be the launch of everything social

Image Credits

I took all of these photos or had someone hold my camera for the pictures