The Red Letter Disciple

020: Bill Woolsey on the #1 Reason Why Ventures Fail, How to Build Courage and Equip Entrepreneurs, and How Mother Theresa and Mark Cuban Work Together


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Bill Woolsey is excited about seeing other people’s creative ideas come to life. After serving as a pastor, Bill started Five Two, an organization which helps entrepreneurs start things! Their proven approach clarifies, equips, and activates the unique callings of others. To learn more about the podcast or access the show notes, visit www.redletterpodcast.com

Creating content is one thing. Distributing it is another. Carey Nieuwhof, through the Influence Kickstarter, helped my organization clarify who its target is, and this has been a game-changer for our business. Carey Nieuwhof and The Art of Leadership Academy are offering this free mastermind that will help you amplify your reach and impact online by: 

  • Identifying your dream audience
  • Learning how to get them to notice you and connect with you; and 
  • Figuring out which platforms are worth your time and effort and which aren’t 

To register for free, visit influencekickstarter.com. Building online influence doesn’t have to be intimidating or complicated. And it also doesn’t have to be gimmicky or ruin your integrity. 

Resources mentioned in the episode: 

Five Two 

Soaring Educational Services 

Faith at Work Devotional from Five Two


Key insights from the episode: 


Billions of people don’t think the way you do, and many of them live right next door to you. - Bill Woolsey


87% of the people in our churches don’t know their spiritual gifting. - Zach Zehnder


Five Two wants to help you clarify, equip, and activate your calling. -Bill Woolsey


The number one reason the young people from my church didn’t come back was that there were no other young people there. - Chris Johnson


The number one reason ventures fail is that they have something nobody wants. - Bill Woolsey


If you can get “Who is this for?” right…you’re there. - Bill Woolsey


Encourage means to literally “pour in courage.” - Bill Woolsey


Five Two: 111 new ventures since 2015  99,505 introductions to Jesus


What’s the platter you are going to serve Jesus on? - Bill Woolsey


Bill Woolsey’s Challenge: If God only allowed me to minister to just one type of person, who would that person be, and what would they be like?


Are you following Jesus? 


Many want to be greater followers of Jesus but don’t know how. We did an extensive study of everything that Jesus commanded of us and located 5 key targets into which Jesus invites 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! Not only will you get results back immediately, but you will also 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. 


Some not-so-key insights: 


Mother Theresa and a friendly Mark Cuban would definitely not have dated. - Chris Johnson


Zach is starting a competitor ministry to Five Two called Seven and a Few.



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