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Turning a Side Hustle into a Full-Time Small Business, with Jonathan Kaylor

Measure Success Podcast

Release Date: 07/05/2022

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Jonathan Kaylor is a Midwest native, and his family have called the Pacific NW home since 2013. For nearly two decades, Jonathan led Customer Service and Inside Sales Teams for Banking, Manufacturing, and Distribution companies. Through Passages to Success, Jonathan is excited to be a student, storyteller, and advocate for Entrepreneurs and Small Business Owners. Outside of the BOB, Jonathan can be found enjoying coffee, beer, or wine, while sitting at the piano, strumming his guitar or cooking a great meal with friends and family.

Instagram: https://www.instagram.com/bizoverbeer/


In This Episode: 

Taking the dive from the corporate world into entrepreneurship is perhaps more popular than ever, especially after the COVID-19 pandemic. But to turn a side hustle into a viable business, entrepreneurs need community, knowledge about potential pitfalls, and confidence to take the plunge.

Our guest this week is one who made that jump: Jonathan Kaylor led customer service and inside sales teams for banking, manufacturing, and distribution companies for nearly two decades. Now, through his Passages to Success business networking community, he’s a student, storyteller, and advocate for entrepreneurs and small business owners.

Tune into the full episode for more about the most common challenges small business owners face, the advice Jonathan gives to those who have reached a plateau in their business growth, why building a superior company culture is so important to actually scaling a business, and more.  

 

Here’s a Glimpse of What You’ll Learn: 

 

  • How Jonathan’s “Business Over Beer” podcast was born, and how the COVID-19 pandemic changed his business model
  • Why Jonathan’s focus has been on micro-enterprise businesses and side hustlers, especially when they’ve reached a “plateau”
  • The two biggest challenges Jonathan sees small business owners struggling with 
  • Why business growth and business culture are inextricably linked 
  • The “invisible weight” that small business owners and CEOs carry around
  • How Jonathan measures success with his community of small business owners
  • What gave Jonathan the confidence to leave the corporate world and start his podcast and business 
  • The boundaries Jonathan has set outside of work, and how those help him measure success in his personal life

Resources Mentioned in This Episode: