Ditch the Nice Guy Act and Become a Leader with Jake Isaacs

Explicit content warning

01/24/25 • 39 min

Hector and Jake Isaacs, the co-founder of Gathering the Kings, have a real heart-to-heart about what it means to be a man these days. Jake opens up about figuring himself out, ditching old ideas about being a guy, and how a tough challenge changed how he sees his purpose, leading others, and relationships. They get real about the stuff guys don't talk about, the myths that hold them back, and the tough truths about being genuine in today's world. It's raw, honest, and will make you think long after the episode's over.

Chapters:

00:00:00 – Kicking Off with the Guest Who Redefines Growth
00:02:04 – Why Jake Isaacs’ Journey Starts with Reading
00:03:03 – What Happens When Identity Becomes Your Shield
00:04:08 – Childhood Stories That Shape Who We Are
00:05:44 – Misaligned Marriages: Hard Lessons from Jake’s Past
00:08:12 – The Dangerous Myth of ‘Happy Wife, Happy Life’
00:12:53 – Are Nice Guys Really Finishing Last?
00:14:37 – Unpacking the Power of Polarity in Love
00:18:43 – The John Mayer Script for Love: Myth or Reality?
00:19:47 – Building Family Mastermind Moments That Stick
00:20:42 – Loneliness, Brotherhood, and the Male Crisis
00:21:40 – How Vulnerability Can Change the Game for Men
00:23:49 – Why Owning Your Story Is a Superpower
00:25:19 – Lessons from a Lifetime of Reading and Reflection
00:28:05 – Mentorship as the Secret to True Growth
00:32:36 – Silent Retreats and Darkness: A Different Kind of Growth
00:37:53 – Redefining Modern Masculinity: The Big Takeaway

Links and Resources:

Jake on LinkedIn
Jake on Instagram
Gathering the Kings
Gathering the Kings on YouTube
Hector Santiesteban on LinkedIn
Hector Santiesteban on Twitter

Thanks so much for joining us this week. Want to subscribe to Modern Masculinity? Have some feedback you’d like to share? Connect with us on iTunes and leave us a review!

Chapters:

00:00:00 – Kicking Off with the Guest Who Redefines Growth
00:02:04 – Why Jake Isaacs’ Journey Starts with Reading
00:03:03 – What Happens When Identity Becomes Your Shield
00:04:08 – Childhood Stories That Shape Who We Are
00:05:44 – Misaligned Marriages: Hard Lessons from Jake’s Past
00:08:12 – The Dangerous Myth of ‘Happy Wife, Happy Life’
00:12:53 – Are Nice Guys Really Finishing Last?
00:14:37 – Unpacking the Power of Polarity in Love
00:18:43 – The John Mayer Script for Love: Myth or Reality?
00:19:47 – Building Family Mastermind Moments That Stick
00:20:42 – Loneliness, Brotherhood, and the Male Crisis
00:21:40 – How Vulnerability Can Change the Game for Men
00:23:49 – Why Owning Your Story Is a Superpower
00:25:19 – Lessons from a Lifetime of Reading and Reflection
00:28:05 – Mentorship as the Secret to True Growth
00:32:36 – Silent Retreats and Darkness: A Different Kind of Growth
00:37:53 – Redefining Modern Masculinity: The Big Takeaway

Links and Resources:

Jake on LinkedIn
Jake on Instagram
Gathering the Kings
Gathering the Kings on YouTube
Hector Santiesteban on LinkedIn
Hector Santiesteban on Twitter

Thanks so much for joining us this week. Want to subscribe to Modern Masculinity? Have some feedback you’d like to share? Connect with us on iTunes and leave us a review!

Previous Episode

Facing Myself Without Booze with Kristian Nylund

Kristian Nylund shares his journey of overcoming the hardships of alcohol dependency, how to handle societal pressures, and redefining himself as an authentic and present father. He talks about the deep insecurities that shaped his choices, his battle to align with his true identity, and the freedom that came with sobriety. Tune in to hear about the hidden struggles of men, the importance of vulnerability, and how the right support system can make all the difference.

Chapters:

00:00:00 - A Candid Beginning
00:01:50 - Steps Toward Sobriety
00:02:43 - The Turning Point for Growth
00:04:01 - Living Authentically Every Day
00:06:42 - Sobriety’s Ripple Effect
00:07:15 - Unmasking Insecurities
00:13:44 - Alcohol: Cultural Norms and Choices
00:16:35 - Choosing a New Path
00:22:22 - Sobriety in Isolation: COVID’s Lens
00:23:54 - Reading Life’s Subtle Clues
00:24:38 - Moderation’s Perpetual Loop
00:25:12 - Drawing a Line in the Sand
00:26:44 - Unpacking Emotional Weight
00:31:47 - Strength in Shared Struggles
00:33:22 - Building Connections That Matter
00:35:01 - Redefining Yourself, One Step at a Time
00:40:55 - Wrapping Up the Journey

Links and Resources:

Kristian on Instagram
Sober Identity Podcast
Hector Santiesteban on LinkedIn
Hector Santiesteban on Twitter

Thanks so much for joining us this week. Want to subscribe to Modern Masculinity? Have some feedback you’d like to share? Connect with us on iTunes and leave us a review!

Next Episode

Love, Lies & The Narcissist’s Game with Marshal Gillen

Marshal Gillen, an award-winning speaker, speaker trainer, and men’s coach opens up about the wreckage and rebirth that followed his last breakup—140 days since his life fell apart, but who’s counting? He and Hector discuss the struggles men face in toxic relationships, the mind games of narcissistic abuse, and the brutal realization that maybe self-worth was never really there to begin with. This is for the guy who feels like he’s losing himself, the one searching for answers, and the one ready to take his power back. No fluff, no filters—just the raw truth about healing, masculinity, and starting over.

Chapters:

00:00:00 – Where It All Begins
00:01:56 – A Familiar Face, A Different Man
00:02:21 – The Armor We Wear, The Weight We Carry
00:04:18 – Love, Need, or Trap?
00:04:59 – The Invisible Chains We Call Love
00:06:21 – The Mirror That Love Holds Up
00:08:21 – When a Boy’s Tears Dry Too Soon
00:11:33 – The Wounds We Deny, The Patterns We Repeat
00:21:18 – Dancing in Circles with a Ghost
00:25:11 – The First Domino to Fall
00:27:24 – The Unbreakable Knot of Pain and Love
00:30:49 – When the Past Knocks, Will You Open the Door?
00:35:32 – Who Are You Without the Pain?
00:39:22 – Four Steps, A Lifetime of Change
00:40:22 – The Purpose Waiting on the Other Side
00:43:41 – Brotherhood, Sanctuary, and the Art of Being Seen
00:47:33 – Faith, Strength, and the Masculine Soul

Links and Resources:

Marshal on LinkedIn
Marshal on Instagram
All of Marshal’s Links and Resources for N.A.R.C. Support
Sacred Kingdom Church
Hector Santiesteban on LinkedIn
Hector Santiesteban on Twitter

Thanks so much for joining us this week. Want to subscribe to Modern Masculinity? Have some feedback you’d like to share? Connect with us on iTunes and leave us a review!