A new breed of entrepreneurship coaches is espousing the benefits of nonstop sharing. But is it really necessary?

FOR ENTREPRENEUR and success coach Chris Winfield, who holds regular conferences on the art of self-promotion, life and content blend together. His commute is the backdrop for a series of videos—live-streamed on Facebook—in which he spouts stream-of-consciousness musings about success and failure in business. A journal entry doubles as a motivational Instagram post. A visit to the candy store with his daughter is the impetus for a lesson on the importance of persistence, a conversation he broadcasts to his followers. Many of the takeaways are so broad, they feel ripped from an inspirational poster.

Winfield is far from the

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