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Creating Connections: The Journey of Old Pal with CEO Rusty Wilenkin

Unveiling the Story Behind a Rising Cannabis Brand

In a recent episode of the podcast Branding Like a Boss, host Angela Pih spoke with Rusty Wilenkin, the founder and CEO of Old Pal, a trailblazer in the cannabis industry. Old Pal has expanded its reach to over 16 states across the United States, aspiring to become a household name in the rapidly growing cannabis market. Wilenkin shared invaluable insights into his journey, the strategies behind Old Pal, and the challenges they face as they navigate this competitive landscape.

From Ambition to Reality: Rusty’s Path to Old Pal

Wilenkin’s love for the cannabis industry began soon after he graduated from college. Initially planning to pivot to a career in finance, he quickly found himself returning to his roots in cannabis by working at Kiva, a prominent cannabis company, while also exploring his passion by running a small growth operation in California’s desert. His experiences from the medical marijuana days to the legalization of adult use in 2018 inspired him to partner with Jason to launch Old Pal. Wilenkin noted, “We felt comfortable and had the idea of launching our own brand at that time.” This leap paved the way for what would become a beloved cannabis brand centered around community and connection.

The Brand’s Essence: Community and Timelessness

The naming of Old Pal is deeply rooted in friendship and camaraderie. Rusty explained how they engaged creative partners from Austin, who collaborated with them to create a brand focused on community rather than the hyper-competitive, trend-driven nature often seen in the cannabis space. The name Old Pal reflects their desire for a timeless brand that evokes feelings of connection and gathering with friends. Wilenkin recalled, “It was about spending time with friends and creating meaningful moments, and Old Pal encapsulated that perfectly.”

Staying Focused on Brand Integrity

One of the defining features of Old Pal is their asset-light model, which sets them apart from traditional vertically-integrated companies within the cannabis space. Rather than owning farms, Old Pal partners with cultivators to leverage their unique expertise, allowing the brand to stay focused on marketing and maintaining high-quality products. Wilenkin emphasized the importance of transparency with their partners, stating, “We want to do right by the people, the plant, the partners,” ensuring that quality is maintained while focusing on brand growth.

Expanding Horizons: Challenges and Strategies

Old Pal’s rapid expansion has been filled with valuable lessons, particularly regarding the complexities of market dynamics and regulations. Rusty explained that every market requires unique strategies, and staying informed is vital. By maintaining strong relationships with their partners and implementing consistent marketing strategies, Old Pal has successfully navigated various state regulations while expanding their product lines. Wilenkin asserted, “We’re not going to do anything unsustainable or crazy. We’re going to keep just staying steady.”

Building Lasting Consumer Relationships

Creating a strong customer base has been integral to Old Pal’s success. Wilenkin and his team prioritize exceptional customer service, ensuring that any complaints or issues are addressed promptly. Their approach has successfully turned past dissatisfied customers into brand ambassadors, fostering customer loyalty that is essential in the cannabis market. The brand’s commitment to feedback reflects their philosophy of creating consumer trust and ensuring consistent product quality across all markets.

Team Dynamics: An Engaged Workforce

Wilenkin noted that despite being a small team of just nine people, Old Pal fosters a culture of openness and respect. This dynamic empowers employees, allowing them to take ownership over their work without stringent oversight. Wilenkin shared, “Everyone’s sort of treated like adults. If you’re getting your stuff done, this is not a company where we police when you’re working.” This internal culture and employee loyalty are critical, ensuring that the team remains invested in the brand’s long-term success.

Exciting Times Ahead: Future Plans for Old Pal

As 2025 unfolds, Wilenkin revealed that Old Pal has exciting plans, including the relaunching of products in Michigan and Missouri, continuing to expand their hemp line, and introducing Old Pal-specific genetics. Moving into new markets, like Florida, further solidifies their growth strategy. The brand aims to maintain consistency across its products while also being open to adaptations that cater to individual market needs.

Conclusion: The Future of Old Pal

With Wilenkin’s visionary leadership and Old Pal’s established commitment to community, quality, and authenticity, the brand is poised for a bright future in the cannabis industry. As they continue to navigate the complexities of market dynamics and consumer preferences, Old Pal remains dedicated to fostering genuine connections—ultimately transforming how cannabis is experienced and shared among friends.

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