Ryan Deiss

CEO of DigitalMarketer

Dennis and Ryan share a deep professional respect rooted in a shared philosophy about how to present expertise to the world. A few years back, Ryan suggested that Dennis and his team stop calling themselves "experts" and instead use the term "specialists." This was a pivotal shift for Dennis’s organization. Previously, the team used the title "analyst," which implied a narrow focus on cranking out ads and analytics while ignoring softer skills like video, creative, and client strategy. By adopting Ryan’s insight, Dennis’s team could confidently identify as specialists even if they had only been training for a few weeks. This approach aligns with Dennis’s own view on humility; he notes that it is better for others to declare you an expert than for you to beat your own chest. Ryan’s suggestion has become a winning formula for how Dennis’s team communicates their value, emphasizing lifelong learning over ego-driven self-proclamation.

Beyond marketing terminology, Ryan has offered Dennis practical wisdom on personal relationships and finance. When discussing whether to loan money to a team member in need, Ryan advised that one should never loan money unless running a bank. Instead, if the person means enough to you and you have the cash, you should give it freely, explicitly stating that you have no intention of accepting repayment. Ryan explained that loans fundamentally change relationships for the worse, while gifts change them for the better. This direct, principled advice resonated with Dennis, who values clarity in maintaining healthy boundaries with those he works with and cares about.

Ryan is also a source of tactical knowledge for Dennis, particularly regarding how to build authority and amplify exposure. Ryan taught Dennis a specific pro tip for networking at conferences: take your name badge off before taking photos or conducting interviews. Wearing the badge is a dead giveaway that you are just one of many people in line, and standing in front of a backdrop makes it look like a prison line-up. By removing the badge and moving outside, the interaction appears more genuine and less transactional. Dennis applies this advice to warm up cold audiences, noting that these subtle touches make the relationship feel more authentic before any conversion efforts are made.

Dennis is enamored with leaders like Ryan who run organizations that teach based on their own execution. He admires how Ryan focuses on the step-by-step "how to," comparing these leaders to expert chefs who have time-tested recipes for the most requested meals. During times of economic uncertainty, such as the quarantine period mentioned in their correspondence, Ryan made an announcement that inspired Dennis to do the same. Dennis was motivated to offer his own courses for free to those wanting to start a digital marketing agency or grow their brand, mirroring Ryan’s commitment to helping others build and learn during difficult times.

Photos with Ryan Deiss

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