Simon Whitbread

Jaime Jay welcomes Simon Whitbread to today’s podcast. Simon is the founder of The Business Conversationalist. Tune in to learn how you can optimize your business conversations and get the results you want!

The Start of a Journey

Simon used to work for a large insurance company in the UK. He loved working on things that inspire, develop, and grow people.Simon Whitbread The Business Conversationalist

People start a business, and replicate what they do in a corporate world but as a self-employed person.” -Simon Whitbread

He launched his own business about 6 years ago, and spent the last 4 years sharing the importance of conversation and relationships within small businesses.

From Corporate to Individual Credibility

Over the years of being an entrepreneur, Simon learned several timeless lessons. One thing was the sense that organizations do business with organizations.

It wasn’t off the back of my own credibility; it was the organizational credibility.” -Simon Whitbread

Once you start having your own journey, all the credibility you had from the corporate world disappears. That’s when you start building your own credibility. Build relationships off the back of who you are.

Challenges to Growth

Simon Whitbread The Business ConversationalistOne of the challenges that Simon encountered as an entrepreneur was the importance of structure and politics. He shares that when one becomes self-employed, that means nothing to anybody.

It’s the individual personal stuff that makes the biggest difference.” -Simon Whitbread

Another difficulty was pricing. There’s a struggle in moving from a steady salary to an unpredictable pay. Simon discusses how this was so.

Listen to know how you can optimize your business through The Business Conversationalist. Connect with Simon Whitbread at Remember to let Simon know you heard about him on Stop Riding the Pine!

The Business Conversationalist
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Here are the highlights of my conversation with Simon Whitbread if you are in a hurry:

  • Who is Simon Whitbread? ([5:07])
  • Lessons learned from differences? ([7:18])
  • Dealing with pricing? ([9:22])
  • Dealing with expectations and clients? ([12:03])
  • What is The Business Conversationalist? ([13:56])
  • Significance of conversation within an organization? ([19:50])
  • Simon’s Breakaway Moment? ([26:40])
  • Simon’s piece of advice? ([36:43])

Special Mentions:
(iTunes Shout Out) Silly Bands Rock Go by Them

Thank you to Alexis Ayala, for providing the incredible editing for this episode. If you need to find an audio editor, send Alexis an email at

Interview ValetThank you to our awesome sponsor, Interview Valet, A professional concierge guest booking podcast service for hosts and guests – You be the Guest, We do the Rest! Check out their new website at

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