Bill Woolsey on the Red Letter Disciple Podcast

077: Bill Woolsey on the Pitfalls of Entrepreneurship, Clarifying Your Calling, and How to Overcome Fear and the Scarcity Mindset

With decades of experience starting and leading ministries, churches, and networks, Bill Woolsey now invests his life in men and women who want to reach people for Jesus in new, creative ways. In 2009, he led the launch of FiveTwo, a network that helps men and women grow their God-given dreams into ministries and businesses that last. To learn more about the podcast or access the show notes, visit


Today’s episode partner is FiveTwo. The FiveTwo team has grown healthy churches for over thirty years. They understand how to grow churches in a rapidly changing culture without burning out staff and lay leaders. 

Every major church denomination in the U.S. has experienced a decline since the 1960s, a trend the pandemic didn’t initiate but rather accelerated. What are we, as people who love the local church, to do about this reality?

FiveTwo has spent the last four years identifying the four key cultural trends thriving churches address. And they’ve helped countless churches actually address these trends and THRIVE. They’ve put all their learnings along with case studies into a free resource which you can download at today. Discover how well your congregation is managing these forces and what you can do to grow. 

Also, don’t miss my FREE webinar with Bill Woolsey, Founder and President of FiveTwo. We’ll discuss those four trends in detail and discuss how churches can use these trends to grow their churches. Click here or the image below to register.

Resources mentioned in the episode: 

Red Letter Disciple Podcast: Episode 20 Bill Woolsey on the #1 Reason Why Ventures Fail

Seven Steps to Start: A Sacramental Entrepreneur’s Guide To Launching Startups That Thrive (Sacramental Entrepreneur Series) by Bill Woolsey

Red Letter Disciple Podcast: Episode 32 Jessie Cruickshank on Brain Science and Discipleship

Key insights from the episode: 

If you have Jesus, you have more than enough. – Bill Woolsey

When you’re starting new things, money is the biggest fear. – Bill Woolsey

Obedience often precedes Jesus’s miracles. – Bill Woolsey

We have to understand that faith steps include failure. – Bill Woolsey

Fear of losing personal well-being and security keeps people from thinking big. – Bill Woolsey

Fail fast but not fatally. – Bill Woolsey

The line between pastor and boss can be very challenging. – Bill Woolsey

12-14% of the US population are entrepreneurial in their field. – Bill Woolsey

Entrepreneurs don’t have to love risk, but they need to know how to mitigate risk. – Bill Woolsey

You can only spend a dollar once. – Bill Woolsey

Bill Woolsey’s Challenge: Discern what group of people or organization you’re passionate about and do one small thing you could do to help them. 

Are you following Jesus? 

Many want to be greater followers of Jesus but don’t know how. We extensively studied everything Jesus commanded of us and located five key targets to which Jesus invited His followers. The five targets are Being, Forgiving, Serving, Giving, and Going.

In partnership with LifeWay Research, we created a Red Letter Challenge Assessment that will measure you according to these five targets. And the best news of all: it’s free! You will get results back immediately and be presented with the next steps to help you become an even greater follower of Jesus.

You can take the FREE Red Letter Challenge Assessment here.

Watch the entire season for free: 

We’ll be uploading every episode of The Red Letter Disciple on our YouTube Channel. If you aren’t subscribed already, you can do so here.

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