Derek Henmi grew up in Marin County, California. Following in his parents’ footsteps, he graduated from the University of Colorado with a degree in Architecture and Urban Planning and began his career designing large-scale commercial buildings. Over time, he became fascinated with the businesses that lived inside those buildings and how they developed and became so successful. Vivid was launched to create solutions for small and medium-sized businesses so that they could compete with larger, more established companies. And then he turned his attention to the wine industry, so that he could help his friends and acquaintances overcome wine-industry-specific challenges. Here’s his story.
You grew up in the Bay Area; tell us about your family and early childhood. What is the derivation of the family name, Henmi? What does it mean in Japanese?
I was born and raised in Marin County, which is a pretty great place to grow up if you like being outdoors and surrounded by good people, food, and wine. I grew up in a creative and entrepreneurial household. Both of my parents are architects, and together they ran their own firm. So, dinner conversations were a mix of design critiques, business decisions, and the occasional debate about whose sketch was better. Henmi is a Japanese last name, but it is not very common. I’m told it has ties back to an ancient samurai clan, so that would be cool!
What were family celebrations like? Was wine on the table? When did you first get a taste of wine and what did you think at the time?
Big, loud, and frequent. I had a lot of family in the Bay Area, so there was always something to celebrate and a reason to gather. Wine was absolutely always on the table and usually the center of attention.
My parents were pretty intentional about introducing my brother and me to wine early on. I think my first real sip was on a family trip to Tuscany, which, in hindsight, set a pretty high bar. At the time, I probably would have preferred a soda, but over the years, I came around. Now I cannot imagine a great meal or gathering without it.
You graduated from the University of Colorado with a degree in Architecture and Urban Planning. What inspired you to go that route?
I did not have to look far for inspiration. Growing up around architects, I was constantly exposed to design, buildings, and the idea of creating something from nothing. What pulled me in was the combination of creativity and problem solving. You are not just designing a building, you are thinking about how people live, move, and interact within a space, and then zooming out to how entire cities function. It is a pretty fascinating lens on the world.
Who inspired you the most as a young child? When did you decide to become an entrepreneur?
Definitely my parents. They built their firm from the ground up, and I got to watch that process unfold in real time. It made entrepreneurship feel less like a big leap and more like a natural path.
I do not think there was a single moment when I decided to become an entrepreneur. It was more of a slow realization that I really enjoy building things and taking ownership of ideas from zero to one.
You’ve worked on several large-scale commercial development projects, such as engineering the design of the Golden State Warriors Stadium and building the Genentech Headquarters. How did you get involved with these projects, and then how did you transition from urban planning to business development and starting new companies?
Early in my career, I was lucky to work at firms that were involved in some pretty iconic projects, including the Warriors stadium, Candlestick Point, and Genentech. Being part of something at that scale is exciting. You can actually point to it and say, I helped build that.
Over time, though, I found myself getting more curious about the business side. How do these projects get funded? How do deals come together? How do companies scale? That curiosity slowly pulled me out of pure design work and into business development, and eventually into starting my own companies. It was less of a sharp turn and more of a gradual shift from building physical structures to building businesses.
Why did you decide, as an entrepreneur, to focus on the wine industry?
Interestingly, wine was not the original plan. When I first started Vivid, the goal was much broader. I wanted to build tools that helped small and local businesses compete in a world that was increasingly dominated by larger, more tech-enabled players.
Over time, we started working with some wineries through friends and family connections. At first it was not some big strategic decision; we were just helping people we knew. But pretty quickly, we noticed a pattern. Wineries deal with many of the same challenges as other small businesses, but with even fewer tools built specifically for them. Most of the technology was either too expensive, too complicated, or just not designed with the realities of a winery in mind. That gap really stood out to us. So we leaned in. What started as a few projects turned into a clear focus, and eventually led us to build Vino, a platform specifically designed to give wineries more accessible, modern tools to grow their direct-to-consumer business. In a way, we did not choose wine as much as we discovered it was the place where we could have the most impact.
Tell us about Vino and Vivid Commerce and how they assist wineries with their sales systems. How did the idea get started?
Vivid Commerce really started with a simple idea. How do we give small and local businesses the same level of tools and capabilities that larger companies have, without the complexity or cost?
As we began working more closely with wineries, that mission became a lot more focused. We saw firsthand how fragmented their sales systems were. Ecommerce, wine clubs, point of sale, customer data, all living in different places, often stitched together with workarounds. It made it hard to operate efficiently and even harder to truly understand and engage with customers.
That is where Vino came from. We wanted to build something specifically for wineries that brings all of those pieces together into one cohesive system. Something that feels intuitive, supports how wineries actually sell both online and in person, and ultimately helps them grow their direct-to-consumer business. At the end of the day, our goal is pretty simple: make it easier for wineries to sell their wine and build lasting relationships with their customers, without needing a patchwork of tools to get there.
You’re also the Managing Partner of The Voyages Venture Capital Firm. How did the company get started, and what types of projects do you fund?
Voyages really came out of the same philosophy that led me to start Vivid in the first place. I have always been interested in supporting small businesses and the people who build them, whether that is directly through software or by backing the founders themselves.
Early on, I started making a few investments in companies that were building tools for small businesses or operating in spaces like commerce and hospitality. Over time, that evolved into something more intentional, and Voyages was born to formalize that effort.
Today, we focus primarily on early stage companies, especially those building technology that helps small and mid-sized businesses compete and thrive. I am particularly drawn to founders who are close to the problem, people who have lived it and are building solutions they wish existed.
At the end of the day, it is all part of the same thread. Whether through Vivid, Vino, or Voyages, the goal is to level the playing field and give smaller operators a real shot at succeeding.
How did you get connected with PGWA? What advice do you have for our winery members to increase their sales in this challenging market?
I was actually introduced to PGWA through one of our local sales reps. From the beginning, I was really impressed by how strong and intentional the Petaluma Gap story is, and it immediately resonated with me. I have always had a personal love for the wineries in that area, so it felt like a very natural connection.
What stood out most is how much pride there is, not just in the wines themselves, but in the identity of the region and the community behind it. That kind of authenticity is incredibly valuable.
In terms of advice, I would lean into exactly that. The wineries that are winning right now are the ones that are telling their story well and building direct relationships with their customers. People are not just buying wine, they are buying into a place, a feeling, and a connection.
From a more tactical standpoint, investing in your direct-to-consumer channels is critical. Make it easy for customers to discover you, buy from you, and come back again. The simpler and more personal that experience feels, the more it will pay off over time.
You recently introduced some of the winery members of the Petaluma Gap Winegrowers (PGWA) to your social club, The Amador, in San Francisco. Tell us about the Club and who its members are. We hope to see you on April 29th at the club for the Petaluma Gap wine tasting!
The Amador is a private social club in San Francisco built around wine, hospitality, and community. It brings together founders, operators, creatives, and people who just genuinely enjoy great wine, great food, and great company.
What has been especially exciting for me is bringing the club and PGWA together. It felt like a very natural fit. On one side, you have this incredible group of wineries with a strong regional identity and story, and on the other, a community of people who are curious, engaged, and eager to connect more deeply with what they are drinking.
Creating that bridge between the two has been really rewarding. It is not just about pouring wine, it is about creating experiences, building relationships, and giving people a more personal connection to the Petaluma Gap and the producers behind it.
Have you ever thought about making wine and launching your own brand? If so, what would you make?
I have definitely thought about it. It is hard not to when you spend this much time around wine, especially growing up surrounded by it. My dad has always been a big wine fan, and his story has definitely influenced me. Back in the day, he actually had his own label called St. Denis, and before that he worked in a wine shop in Sausalito during his college years. Hearing those stories and seeing his passion for wine over the years has always made the idea of creating something of my own feel a little more tangible.
I have gravitated toward Tuscan wines, so I would likely take inspiration from that style. Something balanced, food-friendly, and structured, but still approachable. A wine that feels just as at home at a long dinner with friends as it does on a random weeknight. That said, a really good Pinot is hard to beat, so I would probably have a hard time not doing something in that world as well. For now, I am focused on building alongside wineries rather than becoming one, but never say never.
Are you single or do you have your own family and children? What do you like to do in your free time?
I have a wife, Lauren, and our daughter, Harper, who just turned one. Free time is a bit more limited these days, but I love spending time with my family, getting outdoors, and exploring new wineries and restaurants whenever I can.
