Blue Shirt Leadership Podcast

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Bill Lennan

Bill Lennan-Self-Confidence and the Journey of Becoming an Entrepreneur

Welcome to today’s episode of the Blue Shirt Leadership Podcast. On today’s episode, we welcome back to the show Bill Lennan. Bill is a former mechanic, first responder, and tech solution developer. Currently, Bill is coaching people toward self-confidence by training them on their emotional operating system.

Notable Quotes on Becoming an Entrepreneur:

“I started thinking about how to improve things. I always thought about how do I improve the business here. Where is the friction in the business process?”

Ask “How can this business grow, where are the places where there are underserved markets, where there are opportunities.” 

“Start off wherever you start and be grateful for the experience, and not try and compare yourself to somebody who’s been doing it for 5 years or 10 years or 20 years and just be grateful that you get to experiment.”

Show Notes:

00:00-01:11 Kyle introduces today’s guest, Bill Lennan. Bill has been on the show before, so check out that episode if you haven’t heard it yet, and be prepared for some powerful insights on today’s show. 

01:12-04:34 Bill answers the question “How does someone start their entrepreneurial journey in a way that’s not terrifying?” He tells a little bit of his story and how he got started on the journey of becoming an entrepreneur.

04:35-08:15 Bill and Kyle talk about the two things that successful people need to consistently be thinking about. They discuss networking, becoming comfortable talking to people you don’t know, and constantly thinking about how your business can benefit other people and naturally bringing it up in conversation.

08:16-12:46 Bill talks about gaining self-confidence and the importance of starting small and building on your experiences. 

12:47-14:20 Bill and Kyle wrap up their conversation. Bill leaves us with some last words by reminding us that taking small baby steps will get us where we want to go. 

Connect with Bill online at or by email at You can also find him on TikTok at @billlennan.


#entreprenuer #buildingselfconfidence #startwithbabysteps #entrepreneurialjourney #businessowner #becominganentrepreneur


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