The full story

In 2019, I decided to start writing about wineries. Not quick reviews, but long, thoughtful newsletters of 1,500 to 2,500 words about one winery at a time. Each week I dug into a single winery’s history, its craft and what made it special.

What started as a passion project quickly became something more. I was getting to know winery owners, tasting room managers and winemakers across the country. These weren’t business relationships. They were real friendships, built on a shared love of the craft.

A couple of years later, I launched a bi-weekly podcast interviewing winemakers. Those conversations gave me an even closer look at the wine industry. I was talking with people who poured their hearts into every bottle and understood hospitality in a way most businesses never will.

I got to see how wineries actually run, behind the tasting bar and in the cellar. Newsletter readers became podcast guests. Podcast guests became friends. I was becoming part of the wine country community, not just someone writing about it.

I’ve worked in tech since 1993, so I was always curious about the tools wineries used. As a guest, I loved booking tastings online. It was easy, clean and quick.

Then I started hearing what was happening on the other side. Through my friends at wineries, I learned the reality: systems scattered in every direction, the most popular software built for restaurants instead of wineries, and costs that made my jaw drop.

$250 a month. Plus processing fees. Plus service fees. Plus, plus, plus.

These weren’t big corporate wineries. They were the family operations and small producers I’d been writing about and interviewing, and they were being asked to choose between good software and financial stress.

That’s when I knew something had to change. These weren’t just businesses to me. They were the community that had welcomed me, taught me and trusted me with their stories.

Before I wrote a single line of code, I sat down one-on-one with wineries to understand what they actually needed. Not what I assumed, and not what seemed logical from a tech point of view, but what would help them take care of their guests.

The result was Block 55: reservation and event software built specifically for wineries, by someone who understands their world. Every feature exists because a winery asked for it, and every design choice starts with hospitality.

Block 55 exists so every winery, big or small, can have a full-featured reservation system without breaking the bank. That idea guides every decision we make.

No share of your sales. No hidden charges. Your guests never pay a booking fee, card payments run through Stripe at their standard rates, and Block 55 itself is one simple monthly plan.

Our tagline, “The Only Winery Experience Platform Built for Wineries by Wineries,” isn’t just marketing. I listen to wineries because I’m part of this community, and our roadmap follows what wineries need. That’s exactly how it should be.