We’re excited to introduce you to the always interesting and insightful Chaim Litvin. We hope you’ll enjoy our conversation with Chaim below.

Chaim, looking forward to hearing all of your stories today. Do you take vacations? How do you keep things going – any advice for entrepreneurs who feel like they can’t step away from their business for a short vacation?

In the land of bourbon, business never stops. From distilling to distributing, tastings, lectures, pairings, and other events, there’s always something going on. As the founder of BourbonRabbi, I’ve found that while you need to be deeply committed to your craft, you also have to make adequate time for family. It may seem impossible to get away from such a demanding business, but vacations are not just a luxury—they’re essential.

Family must come first. In the end, the memories we make with our loved ones are what matter most. That said, running a bourbon brand, especially a young one, means there’s always something that needs attention—whether it’s managing schedules, keeping tabs on sales in different states, filing federal or state taxes, or organizing bourbon events. We can’t just stay home and expect barrels to age and bottles to sell themselves. While bourbon is a passion, it’s also a business, and businesses thrive when their leaders are balanced. Taking time off with family isn’t just for fun; it’s a time to recharge and build memories that last, which I believe is more important than the business itself.

For entrepreneurs in the bourbon industry, it’s easy to feel like stepping away for even a few days would be devastating. But I’ve found that, with the right systems in place, it’s not only possible but incredibly beneficial. What works for one business may not work for another, but here are some things I implement to help.

The bourbon industry is unique in its complexity, and there are countless tasks to attend to—from tracking the aging process to rotating barrels, scheduling a bottling run while ensuring the right barrels are ready to go, and making sure bottles, corks, and labels are on site and correct. Over time, I’ve built systems that ensure every stage of production runs smoothly, whether I’m at the distillery or not. Standardizing processes is very helpful for this. Everything from tracking barrel rotations to scheduling bottling lines ensures that all team members know exactly how things should run in my absence. These systems are like a recipe for consistency, ensuring the quality of BourbonRabbi’s products remains high, even when I’m away.

In the bourbon world, trust is everything, especially when it comes to your team. Just like bourbon ages over time, building a great team takes patience. I’ve learned that delegating tasks and trusting my team is crucial. From top to bottom, I’ve hired people I can count on to maintain the BourbonRabbi standards. Giving them the responsibility to manage operations, handle clients, and make decisions allows me to step back without worrying.

While bourbon may be rooted in tradition, running a modern bourbon business requires embracing technology. Whether it’s using cloud-based tools to monitor sales or checking in with my team through virtual meetings, technology gives me the flexibility to stay in touch with my brand while I’m out of town. I might be on vacation, but I can still have my finger on the pulse of the business, checking key metrics or overseeing a shipment remotely.

That said, I also believe in integrating work into vacation when it makes sense. Sometimes, while on the road with my family, I’ll do a tasting, visit a liquor store to sign bottles, or give out merch. It’s a way to keep things moving without feeling like I’m neglecting the business. However, I’m careful to make sure this doesn’t overtake the vacation. The primary purpose is still to relax and spend time with family, so I schedule work activities sparingly, make sure they don’t dominate the trip and get the kids involved. This way, I stay connected to my business without losing focus on the reason I’m taking time off in the first place—family.

Every bourbon producer knows there are key times in the year when things get especially busy—tasting events, festival seasons, or major production cycles. When planning vacations, I always look at the bourbon calendar. Taking a break during slower times helps ensure I’m not leaving during critical moments. Whether it’s after bottling a new batch or before a major event, finding those windows is key to balancing work and life.

At the end of the day, bourbon is a long game. It takes years for a batch to age, and it’s the same with a business. Taking the time to recharge—whether through a vacation or spending quality time with family—ensures you’re playing that long game to the best of your ability. When I return from a break, I’m more energized, focused, and often full of new ideas that help move BourbonRabbi forward.

For those in the bourbon world who feel they can’t take a break, I encourage you to invest in your team, your systems, and yourself. By doing so, you’ll find that not only does the business keep running, but it thrives—and so do you.

Chaim, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

I’ve been working in the bourbon industry for nearly 20 years, but my journey started in a slightly different place: kosher supervision. Over the years, I certified many distilleries and got to know the intricate process of making bourbon inside and out. In 2017, the Wall Street Journal did an article about my work, which really opened doors for me. Soon after, I began receiving requests from distilleries across the country to certify their products as kosher. At the same time, I started leading bourbon trail tours and hosting tastings and lectures all over the world, sharing my passion for bourbon with enthusiasts from all walks of life.

When COVID hit and travel came to a halt, I saw an opportunity to pivot. That’s when I decided it was time to launch the BourbonRabbi brand. I wanted to create something that represented my passion for bourbon and my dedication to offering high-quality kosher options. Now, BourbonRabbi has five bourbons on the market, each crafted with care and tradition, and we’ve expanded to include a large merchandise store for fans who want to represent the brand.

What sets BourbonRabbi apart is our commitment to kosher, quality, and authenticity. We’re a small, family-owned operation, focused on creating a product that not only meets kosher standards but also delivers an exceptional bourbon experience. Our bourbons are locally crafted, with an emphasis on flavor, balance, and craftsmanship, so each bottle stands out.

I’m proud to offer kosher bourbon at an affordable price without sacrificing quality or variety. Whether you’re new to bourbon or a seasoned enthusiast, we aim to provide something special for everyone. One of the most gratifying parts of my journey has been hearing from master distillers and experts in the field who say they enjoy my products. While receiving medals from spirit competitions is an honor, knowing that my peers respect and appreciate the work I do means even more to me.

In short we’re a small operation, working hard to put out bourbons that the world will enjoy. Whether you’re sipping it at a tasting, celebrating with family, or sharing it with friends, I hope our bourbon adds something special to every occasion.

We’d love to hear the story of how you turned a side-hustle into a something much bigger.

My journey into the bourbon industry started as something of a side hustle while juggling multiple responsibilities. For nearly 20 years, I was deeply involved in kosher supervision, certifying distilleries and other food production facilities. At the same time, I was also leading talks, tastings, team-building exercises, and giving tours on the bourbon trail to groups from all over the world. All of this was in addition to my work at my synagogue, Chabad, where I’m the Rebbe’s emissary in Louisville, Kentucky, as well as running my charity, Project Friendship, and, most importantly, being a husband and father to six incredible children.

It wasn’t easy to balance everything, but I believe in the saying, “If you want something done, task a busy person with it.” As my passion for bourbon grew, so did the demand for tastings, lectures, and private events. It started off slow, but over time, things picked up, and I found myself working harder to meet the demand. Despite how busy things got, each new opportunity felt like a natural progression.

In 2021, after years of working in the bourbon industry as a kosher certification specialist, I decided to take a bigger leap and launch the BourbonRabbi brand. That was a turning point where bourbon became more than just a side hustle—it became a full-fledged business. However, even though BourbonRabbi now plays a significant role in my life, my other responsibilities—kosher supervision, Chabad, Project Friendship, kosher, and family—are still incredibly important to me.

There have been several key milestones in scaling up BourbonRabbi. Each new state we enter is a huge accomplishment, but what’s even more exciting is when those states reorder our products. Being accepted into two Costco locations and dozens of Total Wine & More stores were also major achievements that helped grow the brand.

The biggest challenge in turning BourbonRabbi from a side hustle into a full-time business was balancing it with my other responsibilities. When I first jumped headfirst into the bourbon industry, the community was so welcoming, which made the transition easier. But in the beginning, it was tough to push the bourbon work aside to fulfill my other duties. It’s been a journey of constant learning and adaptation, but I wouldn’t have it any other way.

How do you keep your team’s morale high?

Managing a team and maintaining high morale starts with leading by example. Demonstrate the commitment and enthusiasm you want to see in your team. People say dont ask your employees to do somethning you wouldnt. I dont fully agree with this. Trust your team to do the things you dont know how to do. You dont have to be an expert on everything.

Contact Info:

• Website: bourbonrabbi.com
• Instagram: @bourbonrabbi
• Facebook: @bourbonrabbi
• Youtube: youtube.com/bourbonrabbi
• Other: shop.bourbonrabbi.com