$55 Million with only 5 employees - Kris Dehnert
Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
Podcast Summary
In this episode of The Proven Podcast, Chris Dennard shares his remarkable journey from selling print-on-demand t-shirts to building Dugout Mugs into a $55 million business with only five employees. (00:54) Chris reveals how he bought back his company from bankruptcy and transformed it into a lean, highly profitable operation that produces premium baseball bat barrel mugs for every MLB stadium, major corporations, and celebrities. (42:33) The conversation covers his multiple business ventures, including a $20 million t-shirt empire with just six people, and his philosophy of building systems where he's not a critical component. (30:03) Throughout the discussion, Chris emphasizes his commitment to being present for his family while scaling businesses through strategic partnerships, efficient systems, and leveraging technology like AI for customer service.
- Main Theme: Building scalable, profitable businesses with minimal staff by focusing on systems, delegation, and staying true to personal values and family priorities.
Speakers
Chris Dennard
Chris Dennard is a serial entrepreneur who has built multiple million-dollar businesses with remarkably small teams. He previously created a $20 million print-on-demand t-shirt empire with only six employees and helped write Teespring's affiliate program. (02:33) Chris currently owns Dugout Mugs, a $55 million company that transforms baseball bat barrels into premium mugs, serving every MLB stadium and major corporations like Coors, Miller, Coke, Pepsi, T-Mobile, and Capital One. He also owns Big Golf, a golf company where he holds 60% equity, and has a cigar line, demonstrating his ability to build synergistic lifestyle businesses.
Key Takeaways
Create Systems You're Not a Component Of
Chris's primary philosophy is building businesses where he becomes irrelevant to daily operations. (30:03) He believes that if you're mission-critical to your business, you've created a prison, not a business. This approach requires identifying each team member's core competency and allowing them to operate independently within their lane. Chris keeps a Post-it note above his computer that says "fire yourself" as a constant reminder. The goal is to be the beneficiary of the system rather than a necessary component, which allows for true scalability and personal freedom.
Hire the Person, Teach the Job
Rather than hiring for specific skills, Chris focuses on identifying people's superpowers and natural competencies, then building roles around their strengths. (12:05) He uses the example of George, who is naturally meticulous and OCD, so he put him in charge of logistics. Eric ran commercial kitchens and understands processes, so he handles operations. Chris believes that asking someone to work outside their core competency results in mediocre work that takes twice as long, using the analogy of writing with your non-dominant hand. This approach eliminates the need for micromanagement and creates more efficient, motivated employees.
Focus on Direction, Not Directions
Chris gives his team broad direction about company goals and vision rather than specific step-by-step instructions. (13:47) He ensures everyone understands and has ownership in the collective vision, then steps away and lets them drive toward that goal in their own lanes. This requires asking better questions upfront to ensure alignment, but once established, it empowers employees to think and operate freely. The key is creating shared ownership in the vision so team members are naturally motivated to achieve it without constant oversight.
Ask Three Critical Questions Consistently
Chris regularly evaluates his business by asking: "What's going right? What's going wrong? What do we need to do different?" (19:05) He applies this framework to identify specific areas for improvement, like recognizing they weren't leveraging their social media presence effectively despite having 2.5 million TikTok followers and 800,000 email subscribers. This simple questioning framework helps maintain focus on the most impactful issues and prevents getting lost in vanity metrics or less important activities.
Leverage Multiple Currencies Beyond Money
Chris operates with the understanding that there are many currencies beyond cash, including time, experience, fulfillment, and family relationships. (09:09) He makes business decisions based on whether opportunities fit his lifestyle goals, particularly spending time with his children and maintaining work-life integration. This philosophy influences his partnership choices, business structure, and daily operations. He emphasizes that making money your North Star is foolish since it's just printed currency not attached to anything substantial, while other currencies like family time and personal fulfillment have lasting value.
Statistics & Facts
- Chris built Dugout Mugs into a $55 million per year business with only five employees, demonstrating extreme efficiency in revenue per employee. (00:08)
- His previous print-on-demand t-shirt business generated over $20 million in sales with just six people at their highest point, including three designers, one ads specialist, one customer service person, and Chris himself. (02:33)
- Chris made $1.5 million in residual income at 50 cents per shirt through Teespring's affiliate program on approximately 3 million t-shirts he never touched, designed, or sold directly. (40:48)
