The New Reality Of Customer Acquisition


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In this episode of Tales from the PROS, I chat with Dan Olson, who is the CEO of, a successful entrepreneur who has spent over 15 years in the digital marketing industry. He is passionate about creating and empowering successful relationships between businesses and trusted marketing services providers. We talk about Dan's story of how he built and scaled UpCity to becoming a leader in its space, the challenges of building up a successful business and the sacrifices he made during the process, he explains how to differentiate yourself in a competitive market, advice to other business leaders, and much more.

  1. Dan, I am glad that we have finally been able to connect on here, although I am aware of what you do, can you tell us more about your story?
  2. My company is currently a customer of UpCity, what triggered you to differentiate your business platform and strategy from other digital marketing agencies? Since we all know it’s heavily saturated.
  3. In your experience with marketing and helping startups and companies for so long, what do you see as their biggest challenges they have in common on marketing or business perspective, and what guidance or advice do you give to help them?
  4. Any advice, tips, or strategies on how to market yourself or your brand in today’s competitive digital age?
  5. What stage of growing and scaling UpCity would you say has been the most challenging for you? And what stage has been the most enjoyable?
  6. Did you build UpCity from the ground up? If so, do you think bootstrapping is a good idea or is it smart to look for outside funding?

Three How's Explained:
  1. How do you define failure?
  2. How do you define your story in one sentence and in one word?
  3. How do you define success?