Jake Sanders on the Road, Cigars, and Community

From Creekside Podcast Ep. 040: Cigars in Cars with Jake Sanders of Crowned Heads, aired Dec 26, 2025. Recorded at Creekside Cigar Co. in Maineville, Ohio.

On this episode of the Creekside Podcast, Dave takes a drive down US 22 with Jake Sanders of Crowned Heads. Between cigars and stories about the road, they talk about the friendships that grow through the cigar business, what makes a lounge feel welcoming, and Jake’s hopes for the future of cigar retail. It’s a conversation about how relationships and hospitality can matter as much as the products on the shelf.

Why did Dave and Jake take a drive down US 22?

US 22 connects Creekside with places that are part of both Dave and Jake’s lives. Jake says the road runs through Zanesville, where he lives, and stretches toward Pittsburgh. Rather than treating the drive as just a way to get somewhere, they use the time to talk about the work, friendships, and plans that connect them.

Jake spends two to three weeks a month on the road, with much of his schedule shaped by events and visits to shops. He enjoys getting off the interstate, seeing small towns, and noticing what makes different parts of the country distinct. For him, those trips are also a chance to meet people, ask questions, and learn about the places he passes through.

The car gives the conversation its own setting: Jake’s Cadillac DTS, which he calls the “Rolling Cigar Lounge.” He describes it as a comfortable way to cover the miles while keeping wear off his truck. The drive feels like a natural extension of the relationships that have formed between Jake and the Creekside crew.

How do cigars help people connect?

Dave and Jake return to an idea that sits at the heart of the episode: a cigar lounge can bring together people who might not otherwise share a conversation. Dave recalls friends who don’t smoke cigars coming to Creekside and enjoying the mix of people in the room. During one evening, people with different jobs and backgrounds joined the conversation around a shared interest.

For Jake, those encounters are one of the meaningful parts of his work. Traveling and smoking with people can help make a conversation feel less formal and create common ground. He values the chance to experience local communities and hopes people can get to know one another beyond assumptions made from a distance.

They also describe the pace of the hobby as part of its appeal. A lounge offers a place to sit, talk, and spend time with other people rather than rushing through an interaction. That shared experience is a big part of why both men value the cigar community and their work in it.

What makes a cigar lounge experience memorable?

Hospitality is a recurring theme. Jake talks about growing up in a family where hosting and serving guests were treated as an honor. That background shaped his interest in the experience customers receive, not just the transaction. Dave sees a similar commitment in the Creekside crew: welcoming people, asking what they are looking for, and helping them find a good fit.

They discuss how independent shops can build lasting relationships through attentive service. Creekside can’t compete with the largest online retailers on price, Dave says, so the shop has to earn loyalty by making the visit worthwhile. The team’s goal is for customers to feel good about their time in the lounge and want to return.

Jake says business relationships work best when both sides show care and follow through. He wants to be more than a person who takes an order; he wants to understand how the retailer and brand can help each other succeed. Dave says that practical, personal approach has made Crowned Heads an important part of Creekside’s growth.

What is next for Creekside and Jake?

Dave shares that Creekside is developing more exclusive and custom cigars, including a planned collaboration with Warped and a Creekside cigar of its own. He also describes the Creekside Collective, an idea for connecting cigar lounges that care about the customer experience. The group could help participating shops learn from one another and make it easier for cigar consumers to find welcoming places to visit.

Jake, meanwhile, reflects on his path into cigar sales and the possibilities ahead. He says his sales reports were up 50% through November compared with the prior year, and credits the retailers and relationships that helped make that growth possible. He is still considering what his next step might look like, but says he is drawn to the hands-on work of helping a brand, its retailers, and its consumers succeed.

For both of them, the conversation points back to the same principle: good business can be personal. A cigar, a welcoming lounge, or a thoughtful visit on the road can open the door to friendships and shared work that last beyond a single transaction.

Key takeaways

• Jake spends much of each month traveling for events and retailer visits, and enjoys exploring small towns along the way.
• Dave and Jake see cigar lounges as places where people from different backgrounds can find common ground.
• Hospitality and attentive service are central to the kind of lounge experience Creekside wants to offer.
• Creekside is working on future custom cigars and developing the idea for a network of like-minded lounges.

Cigars from this episode

• Blood Medicine — Bear Run: Dave says he is smoking it and that Jake Sanders came up with the name.
• Crowned Heads — Mil Días Classic: Jake identifies his cigar as a “Classic Mil Días,” though the transcript garbles the name.

Shop, smoke and listen with Creekside

• Shop the cigars from this episode
• Join the Creekside Cigar Club for boutique cigars picked by our crew every month
• Visit our cigar lounge at 1381 US-22, Maineville, OH, open seven days a week
• Subscribe to the Creekside Podcast on YouTube and catch every episode