MB008: Simplifying how to reach your students with Rob Hastings from Onlessons.com

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In this episode we talk about effective communication, selling your first venture and how you pivot in the development of you business with Rob Hastings from Onlessons.com.



The Pre-Brief: Rob Hastings is the Founder of OnLessons.  He graduated from the US Naval Academy in 2005 as a Surface Warfare Officer and separated in 2011.  After founding and selling his first company, he founded OnLessons.com, an online platform that connects students and teachers by making scheduling and paying easier.


  • Service members can be scared to start a business because they are used to having an organization that takes care of you.
  • His first venture, Papereditnow.com came from his parents influence, who were English teachers.  The business offered online paper editing.
  • If you cannot communicate through the written word then you fail in being able to share your message.
  • Learning to pivot once assumptions are proven wrong.
  • Understanding the barriers to entry that are being created in your systems
  • Finding the super users, the 20% that generate 80% of the volume.
  • The benefits of not taking capital investment and choosing to bootstrap

 Rob’s Advice for military entrepreneurs:

Don’t be afraid to do it, find your customers and ask them what they think.

 Resources for this episode:

How to reach Rob.


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