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
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Register for Leaders Gathering: https://leadersgathering.leadtowin.com/
Information on Milestone Church: https://milestonechurch.com/

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GET IN TOUCH: Contact us at [email protected]

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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 [email protected]

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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 [email protected]

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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 [email protected]

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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 [email protected]

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The hardest room to lead is often your own home. In this conversation, we sit down with Pastor Jeff to share the tension every communicator feels when teaching on family: staying honest without dishonoring your story, offering hope without pretending you have a perfect formula, and resisting the pressure to turn principles into rigid methods people can copy and compare.

TIMESTAMPS
0:00 - Welcome And How It Began
3:05 - Why Family Topics Draw Leaders
10:15 - Defining The Reluctant Leader
18:55 - Why Family Feels So Painful
28:55 - Prodigals And The Need For Hope
33:10 - When Kids Become A Bigger Idol
38:20 - Home Stability Expands Leadership Capacity
41:50 - Parenting Principles Beat Parenting Formulas
49:40 - Marking Moments That Make Love Felt

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 [email protected]

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In this powerful episode of Lead to Win, Pastor Jeff Little sits down with leadership coach and pastor Coach Tom Mullins for a conversation on the one thing every leader must protect—integrity.

Drawing from decades of experience developing leaders, Coach Tom shares the lessons that shape a lifetime of influence. From defining your legacy to calling out the champion in others, this episode is packed with practical wisdom for leaders who want to finish well, not just start strong. You’ll discover why integrity is the foundation of lasting leadership, how to build a life that outlives you, and what it really means to lead with honor in every season.

If you’re serious about becoming the leader God has called you to be, this conversation will challenge and strengthen you.

TIMESTAMPS
0:00 - Legacy Starts With Integrity
0:25 - Fishing Trips And McDonalds Laughs
5:00 - Why Coaching Principles Transfer Everywhere
8:05 - Coach Not Boss Leadership Model
12:35 - Building A Coachable Curious Culture
17:45 - Recruiting Team Depth And Developing Leaders
23:40 - Keeping Score And Staying In Growth
24:05 - Integrity Under Pressure In Public Life
30:32 - Crisis Preparation And The Four As
37:01 - Final Charge Call Out Champions

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 [email protected]

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In this episode of the Lead to Win podcast, Jabin Chavez joins Pastor Jeff to talk about the real cost of leadership at the next level. From public success and private pressure to unmet expectations and pushback, this conversation gets honest about what happens when expansion exposes your internal health.

New levels bring new devils.
New influence brings new responsibility.
And if you’re not healthy, growth will reveal it.

Jabin shares practical wisdom on leading through criticism, building the right team, embracing spiritual maturity, and staying grounded when momentum increases. If you’re building something meaningful — in ministry, business, or leadership — this episode will challenge you to focus not just on growth, but on depth.

Because the question isn’t how big you can grow.
It’s how healthy you are when you get there.

TIMESTAMPS
0:00 - Public Success, Private Strain
1:45 - Vegas Church Plant And Building Miracle
5:55 - From Youth Pastor To Senior Leader
9:50 - Discernment, Timing, And Wise Counsel
14:35 - COVID Shock: Becoming A Leader
18:30 - Casting Vision And Inviting People In
23:20 - Growth Surges And Unmet Expectations
28:40 - Clarity Of Vision Over Crowd Noise
33:10 - Designing Spaces For Connection
36:50 - Filtering Feedback And Inputs
41:20 - Tribe, Comparison, And Security
45:10 - Rhythm Over Balance For Sustainability
49:20 - Managing Time, Systems, And Sermons

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 [email protected]

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What if the key to leading with clarity isn’t found in a strategy—but in stillness?

In this powerful episode of Lead to Win, Pastor Jeff sits down with Pastor Jim Lafoon to unpack one of the most important disciplines for any leader: learning to hear the voice of God. From real-life crisis moments to daily decisions, Jim shares how practicing quietness before the pressure comes prepares you to stand strong when it does.

You’ll hear practical wisdom on discerning God’s voice, building a reflex of prayer, cultivating a culture of intercession around your leadership, and why “dialogue is your birthright.” Whether you’re a pastor, business leader, parent, or team builder, this conversation will challenge you to pause, quiet your soul, and give God space to lead you.

If you want to win at what matters most, it starts by learning to listen.

TIMESTAMPS
6:21 - From Monologue To Dialogue With God
11:41 - Sense God Before You Hear God
18:22 - Training To Hear Under Pressure
26:04 - Signs Of A Spreading Revival
27:06 - Posture: Repentance, Holiness, Prayer

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 [email protected]

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What if the thing holding your leadership back isn’t strategy… but your soul?

In this episode, Pastor Jeff sits down with Pastor Steve Robinson to unpack Soul Leadership—how trauma and chronic stress reshape the brain, why leaders get triggered, and how healthy leaders build healthy teams. You’ll learn the difference between self-leadership and soul leadership, why unprocessed pain turns into unhealthy patterns, and how God can bring you from fragmentation to wholeness.

If you’re a pastor, leader, or team builder trying to finish well, this conversation will give you language, tools, and hope.

TIMESTAMPS:
0:00 - Why Soul Leadership Matters
4:25 - The Book’s Big Idea And Audience
8:40 - Katrina, Burnout, And Hitting The Wall
11:30 - The Soul Leadership Cycle
14:20 - Self Leadership vs Soul Leadership
20:00 - Saul’s Wounds, Shame, And Control
29:20 - Moses Triggered: Accusation And Delay
34:20 - Building Resilience Before Crisis
41:00 - You Can’t Pray Trauma Away

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 [email protected]

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