[Live Training] 9 Strategies to Build Recurring Revenue in your Digital Agency

E138: Overcoming dyslexia and shyness for decades of success with Roland Benson

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Roland Benson founded Benson Design in 1985. He has worked with 1000s of small business owners and entrepreneurs. He found his groove working with smaller companies who didn’t have anyone pursuing them. Now a lot of them are his biggest clients that competitors would love to have. He’s known as the “entrepreneur builder.”

Episode highlights:

  • How Roland adapts to various projects by using an ever-changing team.
  • How Roland weathered the many storms of the last few decades—including 9/11 and the dot com bust.
  • How Roland was coached away from debilitating shyness in a few clever steps.
  • What Roland does with business cards to keep the conversation going.
  • How to start small-talk when you struggle to get into conversations. HINT—take advantage of “small opportunities”.
  • How Roland keeps clients on his team. This process also helps keep his agency front-of-mind for any potential work.
  • Run time: 36:43
  • Best advice received: Trust your gut.
  • Habit that contributes to success: OCD
  • Recommended tools: Audible
  • Recommended book: Marketing Magnet by Dan S. Kennedy



  • “They were doing 2, 3, 4, 5 million dollars a year and nobody was calling on them.”
  • “Hey Dad, isn’t that the guy that bought our house?”
  • “Do what your clients expect and then double it.” (from Ritz Carlton book)
  • “It’s getting out from behind your computer, getting out of your comfort zone.”
  • “You don’t need that many clients…You need good clients, you need to get rid of bad clients.”
  • “I thought I was broken. I thought God hated me.”
  • “Why didn’t you tell us, we would have helped you!”
  • “Before they might have forgotten about us and called someone else.”
  • “I love what small business has done for the world.”


  • Have clients clarify their goals to get started working with you.
  • Move through the fear of admitting what’s holding you back. Many people battle with the same thing, or their own battles! Baby steps are just fine.

Roland’s business card:




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