Lead to Win with Jeff Little

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/

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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/

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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/

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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/

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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/

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