Why Great Leaders Raise Up Generations | Russell Evans

Rich Wilkerson Jr. | Success Isn’t the Goal. Lasting Is.

In this episode of Lead to Win, Pastor Jeff Little sits down with Rich Wilkerson Jr. for a conversation on calling, resilience, and playing the long game in leadership. Rich shares why success isn’t the ultimate goal — lasting is. From processing pain to guarding your heart, this episode will help leaders reframe the story they’re telling themselves and stay faithful to what God has called them to do. TIMESTAMPS 0:00 - Wanting To Last 3:20 - Playing The Wrong Game 6:05 - Esau Spirit And Outdoor Identity 10:20 - Skee Ball Church And Hidden Talent 14:55 - Growing Up In A Ministry Family 21:10 - Pain Trials And Forgiveness 27:45 - Reframing Stories And Trust 33:10 - Discernment And Almost Right 37:40 - Success Redefined As Faithfulness 41:55 - Calling Chose You 45:50 - Exegeting Miami And Loving The Crowd 49:45 - Habits Resilience And Leadership Landmines 58:45 - Final Thanks And Subscribe LEAD TO WIN RESOURCES More Resources: https://leadtowin.com/ Win With People: https://leadtowin.com/pages/win-with-... Register for Leaders Gathering: https://leadersgathering.leadtowin.com/ Information on Milestone Church: https://milestonechurch.com/ FIND US AT: https://leadtowin.com GET IN TOUCH: Contact us at info@leadtowin.com FOLLOW PASTOR JEFF Instagram: https://www.instagram.com/jefflittle/ Facebook: https://www.facebook.com/pastorjefflittle FOLLOW LEAD TO WIN Instagram: https://www.instagram.com/leadto.win/ Musicbed Sync ID: MB01EIB335NJCWV

The Secret to Leading Young People Well

In this episode of Lead to Win, Pastor Jeff Little sits down with Tyron Caswell to talk about reaching the next generation, building a lasting student ministry, and creating environments where young people can encounter Jesus. Pastor Tyron shares pieces of his own story, the early days of Milestone Church, and practical wisdom for pastors and leaders who want to lead with vision, authenticity, and consistency. LEARN MORE ABOUT MILESTONE COLLEGE https://milestonecollege.org/ APPLY FOR RESIDENCY https://milestonechurch.com/ministries/residency/ TIMESTAMPS 0:00 - Finding Your Strength And Staying Consistent 2:10 - A Crisis Moment And Meeting Jesus 6:30 - From Secular Jobs To Church Planting 18:00 - How To Build A Student Ministry 24:00 - Creating Environments For Encounter And Growth 32:30 - Milestone College And Hands On Leadership 39:00 - Developing Leaders And Next Steps LEAD TO WIN RESOURCES More Resources: https://leadtowin.com/ Win With People: https://leadtowin.com/pages/win-with-... Register for Leaders Gathering: https://leadersgathering.leadtowin.com/ Information on Milestone Church: https://milestonechurch.com/ FIND US AT: https://leadtowin.com GET IN TOUCH: Contact us at info@leadtowin.com FOLLOW PASTOR JEFF Instagram: https://www.instagram.com/jefflittle/ Facebook: https://www.facebook.com/pastorjefflittle FOLLOW LEAD TO WIN Instagram: https://www.instagram.com/leadto.win/

Why Great Leaders Raise Up Generations | Russell Evans

In this episode of Lead to Win, Pastor Jeff Little sits down with Russell Evans, founder and global senior pastor of Planetshakers, for a powerful conversation on culture, honor, and raising up the next generation. Russell shares how great leaders build beyond themselves by creating a culture that releases people, honors every generation, and develops sons and daughters who carry the vision forward. From leading a global church movement to empowering young leaders, this conversation unpacks why lasting leadership is not built on celebrity or personality — it’s built on family, honor, obedience, and a heart to see others go further. If you’re a pastor, leader, parent, or anyone passionate about developing people, this episode will challenge you to think differently about legacy, culture, and what it really means to build for generations. TIMESTAMPS 0:48 - A Back Row Story On Humility 3:50 - Russell Evans Origin Story 11:43 - Culture Takes Time And Heart Work 25:40 - Honor As The Key To Family 34:02 - Sound That Shapes Atmosphere And Faith 42:12 - Skill Without Shortcuts DNA Process 52:22 - The Struggle That Forms Leaders 57:38 - Raise Sons And Daughters Not Celebrities LEAD TO WIN RESOURCES More Resources: https://leadtowin.com/ Win With People: https://leadtowin.com/pages/win-with-... Register for Leaders Gathering: https://leadersgathering.leadtowin.com/ Information on Milestone Church: https://milestonechurch.com/ FIND US AT: https://leadtowin.com GET IN TOUCH: Contact us at info@leadtowin.com FOLLOW PASTOR JEFF Instagram: https://www.instagram.com/jefflittle/ Facebook: https://www.facebook.com/pastorjefflittle FOLLOW LEAD TO WIN Instagram: https://www.instagram.com/leadto.win/

It's Not About the Platform | Betsy Caswell

In this episode of Lead to Win, Pastor Jeff Little sits down with worship leader Betsy Caswell for a practical and honest conversation about worship, platform, character, and serving the local church. Together, they unpack why worship leadership is about more than talent, songs, or stage presence. It’s about purity of heart, alignment with vision, serving people well, and keeping Jesus at the center. Betsy shares wisdom from years of leading worship, developing teams, and building a culture where the platform is never the goal — it’s simply a place to serve. TIMESTAMPS 0:00 - What A Worship Win Looks Like 0:36 - Why Worship Shapes Church Theology 6:35 - Betsy’s Story From Music To Jesus 13:38 - Discipleship Before Platform Opportunity 18:31 - Training Worship Leaders With Dev Night 23:44 - Lead To Jesus With Eyes Open 30:34 - Serve Local Church Over Comparison 37:13 - Alignment With Pastor And Team Culture 42:57 - Heart Integrity Beats Production Value 51:55 - Final Thanks And Subscribe Request LEAD TO WIN RESOURCES More Resources: https://leadtowin.com/ Win With People: https://leadtowin.com/pages/win-with-... Register for Leaders Gathering: https://leadersgathering.leadtowin.com/ Information on Milestone Church: https://milestonechurch.com/ FIND US AT: https://leadtowin.com GET IN TOUCH: Contact us at info@leadtowin.com FOLLOW PASTOR JEFF Instagram: https://www.instagram.com/jefflittle/ Facebook: https://www.facebook.com/pastorjefflittle FOLLOW LEAD TO WIN Instagram: https://www.instagram.com/leadto.win/

What You Actually Want For Your Kids

In this episode, Pastor Jeff, Brandy, Caleb, and Hannah unpack one of the most important questions a parent must ask: Are you shaping their behavior… or their heart? Learn how to look beyond outward actions and understand what’s really going on beneath the surface. When you focus on the heart, you’re not just managing moments but shaping who your child becomes over time. TIMESTAMPS 0:00 - The RV Vacation From Hell 4:20 - Why We Teach On Family 10:20 - What Parenting The Heart Means 19:00 - Finding The Heart Under Pressure 20:05 - Moving From Cop To Coach 28:50 - Parenting The Heart With Technology 33:30 - Repairing Connection With Adult Kids 39:15 - Hope, Next Steps, And Closing THE RELUCTANT LEADER EPISODE https://www.youtube.com/watch?v=wisaGThTjKk&t=1s LET'S TALK FAMILY SERMONS https://www.youtube.com/watch?v=ZUcmyRGfTvk LEAD TO WIN RESOURCES: More Resources: https://leadtowin.com/ Win With People: https://leadtowin.com/pages/win-with-... Register for Leaders Gathering: https://leadersgathering.leadtowin.com/ Information on Milestone Church: https://milestonechurch.com/ FIND US AT: https://leadtowin.com GET IN TOUCH: Contact us at info@leadtowin.com FOLLOW PASTOR JEFF Instagram: https://www.instagram.com/jefflittle/ Facebook: https://www.facebook.com/pastorjefflittle FOLLOW LEAD TO WIN Instagram: https://www.instagram.com/leadto.win/