We caught up with the brilliant and insightful Lillian Oler a few weeks ago and have shared our conversation below.

Hi Lillian, thanks for joining us today. Being a business owner can be really hard sometimes. It’s rewarding, but most business owners we’ve spoken sometimes think about what it would have been like to have had a regular job instead. Have you ever wondered that yourself? Maybe you can talk to us about a time when you felt this way?

**Are you happier as a business owner? Do you sometimes think about what it would be like to just have a regular job?**

Absolutely, I’m happier as a business owner. But let’s be real—happiness doesn’t mean it’s always easy. Running a business is like having a front-row seat on the world’s wildest roller coaster. The highs are exhilarating, but the lows? They’ll make you question everything.

Sometimes, I think about what it would be like to be an employee—especially when things get really hard. I think about the people who can show up to work every day and do their same role with passion and commitment—all for someone else’s vision. There’s something admirable about that level of dedication. But for me, I like having my own business to pour my efforts into.

There was a moment recently that made me pause and wonder what life would be like if I just clocked in somewhere, did my work, and left it all behind at 5 p.m. No midnight emails, no worrying about payroll, no *”great, we need more sales this month”* or *”we’re so booked I can’t even keep up with all these requests”* moments.

I remember it vividly. It was a Thursday night, and I was already exhausted. I’d spent the day juggling bookings, marketing systems, networking, and planning for both **Assemble Cocktail Workshop** and my upcoming **pop-up bar concept**. That morning, a last-minute cancellation for a big private event hit my inbox, followed by a major website issue that needed troubleshooting—before I had even finished my coffee. Then, just as I sat down to finally catch up on emails, I got a one-star review from someone who had never even attended one of my workshops. It felt unfair, and honestly, it stung.

For a split second, I thought, *What if I just had a job?* What if I could just show up somewhere, do my work, and let someone else make the decisions? No responsibility beyond my role. No personal stakes. Just a steady paycheck and PTO.

But here’s the thing—I know myself. And that life wouldn’t suit me. I’d last maybe a month before I’d get an idea, start brainstorming, and feel that itch to **build** something again. I *love* creating experiences for people. I love watching a group of strangers bond over cocktails they just learned to make. I love the thrill of pushing boundaries, testing ideas, and seeing something I imagined come to life.

The frustration, the long nights, the stress—they’re all part of it. But so is the **freedom**, the **creativity**, and the deep satisfaction of knowing that everything I build is mine.

So yeah, I think about it sometimes. But then I remind myself: The best things in life aren’t the easiest. They’re the ones you pour your whole heart into. And for me, that’s this business—and whatever comes next.

Lillian, 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’ve always worked in hospitality and naturally found ways to make spaces more engaging, whether behind the bar, creating unique guest experiences, or stepping into roles that didn’t even exist yet. I started my career in Santa Cruz, California, and later moved to Napa Valley, where I worked in a variety of establishments, gaining experience in bartending, service, operations, and guest experience. But what I truly excelled at was spotting gaps in businesses and evolving my role to fill them. I never just clocked in and out—I found ways to solve problems, refine experiences, and improve the business as a whole. The places where I lasted the longest were those that recognized my strengths and allowed me to carve out a role that gave me both purpose and validation. That’s something I have carried with me into business ownership.

Fast forward to 2021, when the world was starting to emerge from pandemic restrictions. People were eager to reconnect, but the way we gathered had changed. I saw an opportunity to create interactive cocktail workshops—an experience that was more than just drinking at a bar. It was about learning, connecting, and creating something together. With limited resources but a clear problem to solve, I launched Assemble Cocktail Workshop in Boerne, Texas.

What started as small group classes quickly grew into something bigger. People wanted something real, something hands-on, something that felt personal. Today, our focus has evolved beyond just cocktail classes—we specialize in corporate team-building experiences and private events because that’s where our impact is strongest. Companies, friend groups, and celebrations come to us not just to learn about cocktails, but to bond, collaborate, and experience something immersive.

Beyond workshops, I have expanded into pop-up bar activations, designing seasonal and themed bar experiences that create buzz, nostalgia, and fun. So far, I have successfully launched Frosted Jack Christmas Tavern, a cozy, festive cocktail experience that became a local favorite; Assembled Heart, a romantic, moody pop-up for the Valentine’s season; and Bettina’s Sailing Club, a tiki-inspired cocktail bar launching in June. Each of these pop-ups is carefully designed, from the cocktail menu to the ambiance, storytelling, and guest experience. They are more than just bars—they are destinations that transport guests to another place, even if just for a night.

What sets my work apart is that I don’t just serve drinks—I create experiences. Whether it’s a cocktail workshop, a pop-up bar, or consulting with other businesses to refine their beverage programs, my focus is on authenticity, connection, and innovation. People are craving real, meaningful experiences, and I deliver that through thoughtful design and storytelling. Every experience I create is about bringing people together in unexpected, interactive ways. I don’t settle for what has been done before—I build concepts that feel fresh, exciting, and different from the norm.

I am proud that I took a small idea and turned it into a thriving business that not only supports me but also provides opportunities for others in the hospitality space. I have built something that blends education, entertainment, and hospitality in a way that feels unique, engaging, and meaningful. And I am still evolving.

If there is one thing I want people to know about Assemble Cocktail Workshop and my work, it is that you’re not just coming in for a drink—you’re stepping into something special. Whether you’re learning to make a cocktail, experiencing a pop-up bar, or collaborating with me on a concept, I want it to feel like something you’ll talk about long after it’s over. And that is what keeps me going.

We’d love to hear about how you met your business partner.

I first met Paula Hayward when she became my landlord at the space where I originally leased for Assemble Cocktail Workshop. She saw my vision and decided to take a chance on it, which, looking back, still amazes me. At the time, I had nothing but an idea—no track record, no revenue, not even a proven concept. I don’t think I would have rented to me, so I’m beyond grateful that she did.

After two and a half years, as the business landscape shifted and Assemble transitioned primarily to a mobile model, I no longer needed a dedicated space and chose not to renew my lease. But I always kept in mind something Paula had mentioned in our early conversations about Assemble—she had obtained a liquor license and had a vacant space just down the road, where she hoped to open a casual cocktail bar. As the owner of a busy bakery, though, the bar never quite came to life.

After experiencing a few business setbacks and projects that didn’t come to fruition, I reached out to her with an idea. I asked if she wanted to take a couple of months to finally finish out the bar space and collaborate on a pop-up together. To my relief—and excitement—she agreed. From that moment, we hit the ground running and launched our first pop-up in just 35 days.

Looking back, it feels like the universe aligned everything perfectly. When I first opened Assemble in 2021, there was no way I could have predicted that our paths would intertwine like this, but somehow, everything came together at exactly the right time.

Can you tell us about a time you’ve had to pivot?

Pivoting has been a recurring theme in my journey—both in business and in life. I’ve always been someone who sees gaps and opportunities, and rather than waiting for someone else to fill them, I figure out how to create a solution myself.

One of my earliest pivots came when my husband and I had our youngest baby while living in Napa Valley. At the time, there was a major shortage of infant childcare, especially options that accommodated the unpredictable hours of hospitality workers. So, I opened a daycare. I used my resources, skills, and understanding of the industry to create something that not only solved a problem for my own family but also met a real need in the community.

Years later, when we moved to Boerne, I found myself in a similar situation. The town had very few entertainment options, and after the pandemic, people had a renewed interest in **hands-on, social experiences**. I recognized that gap and launched Assemble Cocktail Workshop—bringing people together through interactive cocktail-making classes. The timing was right, and people were eager to connect in ways that felt both fun and meaningful.

As the business evolved, I had to pivot again. While cocktail workshops were still in demand, I saw a greater opportunity in corporate team-building and private events. That shift made more sense for long-term growth, booking capacity, and financial sustainability. Then, as the landscape changed once again, I saw another opportunity—collaborating on pop-up bars. Rather than forcing something that no longer fit perfectly, I embraced the next natural evolution of my work.

I think I’m good at pivoting. It’s something that comes naturally to me. The real challenge is **filtering through all the ideas** that come up along the way. I have to remind myself to stay focused long enough to give each venture the time it needs to **gain momentum, build consistency, and scale properly**. That’s the part I continue to work on, but I know that every pivot has led me to where I’m meant to be.

Contact Info:

• Website: https://assemblecocktail.com
• Instagram: https://www.instagram.com/assemblecocktail/
• Facebook: https://www.facebook.com/assemblecocktail
• Yelp: https://www.yelp.com/biz/assemble-cocktail-workshop-boerne

Image Credits

Melissa Levy