P&L: Priorities & Lifestyle Episode 30

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P&L: Priorities & Lifestyle Episode 30 –

Appreciating the Luck that Comes with Success with Jay Holstine

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Jay Holstine is the CEO of Peer Group Advisor and a coach at Vistage, an organization that has catered to CEOs and company presidents for over 50 years. The company’s goal is to provide resources that can help business leaders grow their businesses. As a coach, Jay meets with members once a month to offer in-person sessions that explore what clients are going through, the questions they have regarding expansion, and potentially hidden opportunities. Before becoming CEO, Jay was a managing director at Compass Advisory Consultants. 

Jay joins me today to describe his entrepreneurial journey and what made him appreciate his luck shortly after selling his business. Jay discusses what it was like growing up with entrepreneurial parents. He explains how having a peer group would have improved his business trajectory. He shares some of his professional regrets and his thoughts on working as a consultant for another company. Jay also reveals why some of the best business meetings don’t have a host or speaker.

“One of the things about successful entrepreneurs is they feel like they can do it again and again without appreciating that there was some unbelievable luck.” – Jay Holstine

This week on Priorities Lifestyle:

  • Why Jay decided to become an entrepreneur
  • Shifting from being a consultant to a business owner
  • Why transitioning to entrepreneurship wasn’t tricky for Jay
  • Why it’s challenging to lay people off in a software business
  • Being an entrepreneur and having a partner who is averse to risks
  • Why having a peer group can help create better business decisions
  • Jay’s ventures shortly after selling his business and why they weren’t as successful
  • How luck plays into entrepreneurial success
  • Some of Jay’s regrets after selling his business
  • Jay’s present career and his role in the Vistage team
  • Books for business owners that Jay has recently read
  • The best kind of business meeting

Our Favorite Quotes:

  • “If your parents are entrepreneurs, you don’t see risks the same way you would if they worked for a corporation.” – Jay Holstine
  • “I have a tendency to go fast, but it can be really bad if it’s not the right direction.” – Rob Schulz
  • “It’s important to have that skill that brings the best out of the people you’re mentoring and have them ask questions, so they can help solve problems for themselves and those around them.” – Rob Schulz

Connect with Jay Holstine:

About Rob Schulz and P&L Podcast

The P&L Podcast is a show for business owners. In each episode, host and financial planner Rob Schulz sits down with business owners and the professionals that serve them to talk about business building, life, money — and the all-important transition out of the business, which inevitably happens to everyone who has ever founded a company. 

Email Rob at rob.schulz@schulzwealth.com with questions, comments, and to schedule a one-on-one conversation. 

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