In this episode of Lead to Win, Pastor Jeff Little sits down for a conversation on what it really takes to build a generational church.

They talk about the importance of raising young leaders, creating a culture where multiple generations can grow together, and helping the next generation find their place, purpose, and people. From longevity in relationships to spiritual mothers and fathers, this conversation unpacks why generational leadership is not just about passing down information — it is about walking with people, giving them room to grow, and building something that lasts.

Whether you are a pastor, ministry leader, parent, business leader, or young adult trying to understand your calling, this episode will help you think differently about leadership, discipleship, and the kind of legacy you are building.

TIMESTAMPS:
0:00 - Showing Beats Telling
1:01 - Haircut Counsel And Mullet Stories
3:20 - Building A Culture Of Young Leaders
5:55 - First Night Preaching To 756
6:37 - From Cafeteria Church To Campuses
8:08 - A Bible Study That Sparked Faith
15:12 - Calling And Who You Walk With
19:10 - Opportunities To Shine And Grow
23:12 - Marriage And Ministry As One Team
28:29 - Expansion That Creates More Leaders
36:32 - Invest First And Earn Trust
42:03 - Open Your Life And Multiply Impact
47:14 - Conference Invite And Subscribe Reminder

LEAD TO WIN RESOURCES
More Resources: https://leadtowin.com/
Win With People: https://leadtowin.com/pages/win-with-people
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/

MB01EHWP3SVLB48
MB01OQ7ZOYK7ONK

In this episode of Lead to Win, Pastor Jeff Little sits down with Holly Wagner for a powerful conversation on leadership, pain, resilience, and learning how to stand through hard seasons.

Holly shares from decades of ministry experience, including planting and pastoring Oasis Church in Los Angeles, walking through cancer, navigating betrayal, and learning how to keep going when life and leadership feel heavy. She unpacks why hard seasons are not always destructive, how pain can become part of your purpose, and why leaders have to pay attention to the health of their soul.

Whether you are in ministry, business, parenting, or any season where you feel pressure to quit, this conversation will encourage you to push through the hard, manage your soul, and keep showing up with faith, joy, and endurance.

TIMESTAMPS:
0:00 - Choosing A Different Path
0:56 - Fly Fishing And The Learning Curve
2:45 - Connection To Milestone And Texas
7:55 - From Duke Medicine To Acting
13:40 - Planting A Church In Los Angeles
15:59 - The Black Belt Myth Of Growth
20:40 - Facing Cancer While Leading People
24:50 - Stop Asking Why Start Asking How
27:05 - Grief Loss And Betrayal Collide
31:05 - Learning To Fight With Love
37:10 - Mentoring Leaders With Real Honesty
43:00 - Manage Your Soul And Your Rhythms
52:30 - Enjoy The Journey And Closing

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](mailto: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/

MB01S7YB2Y7TQIG

In this episode of Lead to Win, Pastor Jeff Little sits down with Michael Miller, founder and senior leader of Upper Room, for a conversation on pioneering, prayer, calling, and staying faithful when the path is unclear.

Michael shares the story of how a prayer room in Dallas became a church, what it takes to lead when you do not have all the answers, and why comparison can pull leaders away from the assignment God actually gave them. He also speaks to the next generation of leaders about hidden battles, spiritual formation, and the importance of being planted in the right soil.

Whether you are pioneering something new, developing young leaders, or trying to stay faithful in an uncertain season, this conversation will help you lead with clarity, conviction, and a deeper dependence on God.

TIMESTAMPS:
0:00 - Old Friends And Shared Roots
3:10 - Wedding Photos And Preacher Tie Talk
6:00 - Late Night Prayer And Early Risk
7:40 - The Call To Pioneer In Dallas
12:25 - Leading With Clarity In Uncertainty
16:54 - When People Line Up Outside
18:34 - Songwriting As A Fruit Of Calling
20:20 - Second Generation Leaders And Structure
24:50 - What Young Adults Need Most
30:37 - Soil, Process, And Hidden Battles
33:50 - Apprenticeship And Coaching Trees
36:05 - Spiritual Parents And Learning To Pray
39:24 - Defining Winning As A Leader
43:58 - 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/

MB01OQ7ZOYK7ONK

In this episode of Lead to Win, Pastor Jeff Little sits down with Todd and Julie Mullins of Christ Fellowship for a practical conversation on building healthy teams and shaping culture with intention.

Todd and Julie share why culture cannot just be caught — it has to be taught. From clarifying expectations to communicating values often, they unpack how leaders can build teams people want to be part of and create a culture that is life-giving, healthy, and clear.

TIMESTAMPS
0:00 - Culture As Soil For Vision
3:30 - The Team Question Everyone Asks
8:50 - The Origin Story Behind The Church
15:10 - Succession And Scaling To Multisite
21:30 - Culture By Design Not Default
27:55 - Turning DNA Into Leader Values
35:40 - Communicate Often And Celebrate It
42:10 - Accountability When Culture Slips
49:10 - Hiring On Purpose And Onboarding Fast
56:05 - Clear Expectations And The 30 60 90
1:01:55 - Lead People Holistically And Close

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/

MB01KTGA8DJ2NXM
MB01UVECBC9UVOL

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

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/

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/

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/