The Sales People Podcast

From Cold Calls to CEO: The Solo Founder’s Path to a Million-Dollar Startup


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In this episode, we sit down with Josh, founder of Playbook, to explore his transition from making over 150 sales calls daily to establishing a successful startup. Josh shares insights into the challenges and rewards of being a solo founder, the importance of a consultative sales approach, and strategies for scaling a business in the Middle East.


Topics Covered:

  • The grind of high-volume sales calls and lessons learned
  • Overcoming obstacles as a solo founder
  • Developing a customer-centric sales strategy
  • Adapting to the Middle Eastern market dynamics
  • Building a team aligned with the company’s vision


Show Notes Timestamps:

  • 00:00 – Introduction and Episode Recap
  • 04:15 – Josh’s Journey: From Sales Rep to Founder
  • 12:22 – The Realities of Solo Entrepreneurship
  • 18:35 – Crafting a Consultative Sales Approach
  • 26:45 – Navigating the Middle Eastern Market
  • 33:10 – Team Building and Scaling Strategies
  • 41:20 – Closing Thoughts and Advice for Aspiring Founders


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Tune in to gain valuable insights from Josh’s experience and learn how determination and a strategic approach can lead to entrepreneurial success.

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The Sales People PodcastBy Ben Kinerman-Daltrey