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Starting a business from scratch is an adventure.

In the episodes below we dig deep into the systems, secrets, and stories of remarkable people who dropped everything to start a healthy profitable business.

Jan 1, 2019

Today’s show is the fourth in our series of on-air coaching sessions between veteran executive coach David Quick and an entrepreneur who sits at a crossroads.  A big decision point in his or her business.

Our guest today has built a painless way for your business to share your expertise with the world.  His team includes rock star writers, street-wise marketing gurus, and analytics obsessed techies.  When you put that all together, Content Cucumber has created a one stop shop for building your brand and sharing your perspective with the world.  Our guest today is co-founder Chris Chasteen who started as a financial investor in the project but then felt so connected with it he up his connection to a full-fledged member of the founding team.  

Topics discussed include:

  • Podcasts we’re listening to (4:30)
  • Chris’ Crossroad (7:30)
  • With money out of the equation, which business would Chris choose? (11:30)
  • The steps to making Content Cucumber profitable (17:30)
  • Dave’s tip #1: Setting milestones and the steps to achieve them (26:00)
  • Dave’s tip #2: Prepping for the ownership conversation (32:00)
  • Dave’s tip #3: Create a laundry list of loose ends, if the conversation goes well (35:30)

Mentioned in the episode:


Special thanks to Chris Chasteen for taking the time to share his crossroads with us


Contributors to this episode include:

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Until the next time, We truly appreciate you listening.

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