PLAY FREE Apply

A 9-Month Men's Experience

Play Free

Build what you want. Become who you are. Enjoy the fucking ride.

For ambitious men who have done the inner work and are ready to climb their next mountain, with greater confidence, deeper self-trust, and a brotherhood that has their back.

Apply to join Play Free An application-based men's coaching experience.

You've done the work

Now it's time to play.

You've spent years working on yourself.

You've gone to therapy. Hired coaches. Read the books. Attended retreats. Confronted your past. Learned to recognize your patterns.

You've developed a level of self-awareness most people never reach.

And yet…

  • You still find yourself overthinking decisions.
  • Questioning yourself when things don't go according to plan.
  • Putting unnecessary pressure on yourself to succeed.
  • Feeling anxious about the future, even when things are going well.
  • Or carrying the weight of your business, career, and family without having many places to put it down.

You know better. But knowing better doesn't always mean living differently.

And maybe that's where you are right now.

You're not looking for another breakthrough about your childhood.

You're looking to build something meaningful. To make your next move. To pursue your next mountain. And you'd love to actually enjoy the process.

Welcome to PLAY FREE.

Imagine

What if success didn't have to feel so heavy?

Imagine waking up excited about what you're building.

You have a clear vision. You know what matters. You're disciplined and committed to doing the work.

But you're not gripping the outcome.

You don't spend your days worrying about what might go wrong. You don't need every client, investor, colleague, or partner to validate your worth. You trust yourself to figure things out.

When challenges arise, you meet them with curiosity instead of panic. When you fail, you learn. When you succeed, you celebrate.

And when life gets heavy, you have other men you can call.

Men whounderstand your ambition.
Men whowill lovingly challenge your bullshit.
Men whowill celebrate your wins without comparison.
Men whowill remind you who you are when you forget.

What if you could be deeply committed to your mission and completely free in how you pursue it?

That's what we're here to practice.

Introducing

Play Free

A nine-month coaching and brotherhood experience for men pursuing their next mountain.

PLAY FREE is a men's group for men who are ready to move beyond simply understanding themselves and start living with greater freedom, courage, and self-trust.

This isn't about becoming more productive. It isn't about fixing yourself. And it isn't about abandoning your ambition in pursuit of inner peace.

It's about integrating the two.

Outer excellence
Inner freedom
Discipline
Play
Ambition
Presence
Courage
Tenderness
Personal responsibility
Genuine support

Over nine months, we'll explore the subconscious patterns that influence how you work, lead, love, and live.

We'll challenge the beliefs that keep you playing small, playing safe, or playing from fear.

And we'll support each other in pursuing meaningful, measurable goals.

Because the goal isn't simply to achieve more. It's to become the kind of man who can pursue what he wants without losing himself along the way.

Your mountain

Bring your mountain.

Every man enters PLAY FREE with something meaningful he wants to create, change, or accomplish.

Maybe you're:

  • Launching a business you've been dreaming about for years.
  • Scaling your agency and learning how to lead instead of doing everything yourself.
  • Making a bold career move.
  • Building wealth without sacrificing your health or relationships.
  • Becoming a more present husband, father, or leader.
  • Rediscovering your creativity, desire, and sense of adventure.

Whatever your mountain, you'll spend nine months pursuing it alongside men who are equally committed to their own.

We'll work on the external challenges. But we'll also pay attention to what's happening internally.

The fear of failure The need for approval The constant comparison The perfectionism The pressure to prove yourself

Sometimes the biggest obstacle isn't the mountain. It's the way we've learned to climb it.

The route

The nine-month journey

Our experience unfolds through nine monthly themes designed to move you from awareness into courageous, aligned action.

Month 1: See Clearly01Month 2: Trust Yourself02Month 3: Choose Courage03Month 4: Own Your Desire04Month 5: Find Your Center05Month 6: Deepen Connection06Month 7: Build Freely07Month 8: Lead Fully08Month 9: Play Free09BASE · AWARENESSSUMMIT · INTEGRATION
  1. Month 1

    See Clearly

    Awareness before action.

    Recognize the unconscious patterns influencing your decisions, behaviors, and relationships.

  2. Month 2

    Trust Yourself

    Reclaim your inner authority.

    Stop outsourcing your confidence to results, approval, and external validation.

  3. Month 3

    Choose Courage

    Move with fear, not from it.

    Learn to take meaningful action without needing certainty or guarantees.

  4. Month 4

    Own Your Desire

    Build the life you actually want.

    Reconnect with your vision, your ambition, and the things that genuinely matter to you.

  5. Month 5

    Find Your Center

    Stay grounded when life gets loud.

    Develop the capacity to navigate pressure, uncertainty, and setbacks without losing yourself.

  6. Month 6

    Deepen Connection

    You don't have to carry it alone.

    Strengthen your relationships, practice vulnerability, and learn to receive support.

  7. Month 7

    Build Freely

    Discipline without rigidity.

    Create, execute, and pursue your goals with focus, creativity, and greater ease.

  8. Month 8

    Lead Fully

    Bring your whole self to the table.

    Develop the confidence, emotional intelligence, and presence to lead from authenticity rather than fear.

  9. Month 9 · Summit

    Play Free

    Integrate everything you've learned.

    Celebrate your progress, recognize who you've become, and create a new relationship with ambition, success, and freedom.

The experience

Two group sessions every month

One circle goes deep. One circle moves the work forward.

The Work

90 MIN

Our deeper coaching circle.

A confidential space to talk about what's really happening in your life. We'll explore our monthly themes, examine subconscious patterns, challenge one another, and create new possibilities.

Sometimes the conversation will be about money. Sometimes leadership. Sometimes:

marriagefatherhoodsexresentmentbeing the one everyone depends on

Nothing is off the table. You don't have to arrive with a breakthrough to share. You can simply arrive as you are.

The Mountain

60 MIN

Our progress and accountability circle.

This is where we bring our real-world ambitions into the room.

  • What's working?
  • What's not?
  • Where are you stuck?
  • What decision are you avoiding?
  • Where are you making things harder than they need to be?

We'll celebrate wins, work through challenges, and help each other move forward with greater clarity and confidence.

Weekly

Your Journeyman

You'll be paired with another man in the group. Someone to walk alongside you throughout the experience.

You'll connect weekly to share progress, talk through challenges, and hold each other accountable to your commitments.

Not another person to impress. Someone who knows what you're building and genuinely wants to see you succeed.

Monthly

Practices between sessions

Each month, you'll receive reflection prompts and practical exercises to help integrate what we're exploring.

These aren't assignments designed to keep you busy. They're opportunities to practice a different way of being in your actual life.

Always on

A private brotherhood

A dedicated space to connect with the other men between meetings. Share wins. Ask for perspective. Vent about a hard day. Get support when you need it.

Sometimes the most valuable thing isn't another coaching session. It's knowing you don't have to figure everything out alone.

Fit

Who this is for

FOR Men who

Have already done meaningful inner work.
You're familiar with therapy, coaching, men's work, or other forms of personal development.
Are building something meaningful.
You have a goal, vision, or next chapter you're actively pursuing.
Want to experience greater ease.
You're ambitious, but you're tired of letting pressure, fear, and overthinking drive the process.
Value brotherhood.
You want genuine relationships with men who can celebrate, challenge, and support one another.
Are willing to be coached.
You can receive feedback, examine your blind spots, and take responsibility for your choices.
Want to enjoy your life now.
You're no longer interested in postponing your happiness until you've achieved the next milestone.

NOT FOR Men

Looking for a quick fix.
There are no shortcuts or magic formulas here. We're interested in meaningful, sustainable growth.
Unwilling to be challenged.
You'll be supported, but you'll also be invited to examine your assumptions, patterns, and blind spots.
Who want someone else to do the work.
I'll coach you. The group will support you. But you're responsible for your decisions and actions.
Looking primarily for therapy or intensive healing work.
There may be emotional work along the way, but PLAY FREE is a coaching experience focused on your present life and future direction. It is not a substitute for mental health treatment.
Who value time spent together over insight experienced.
We allot 90 and 60 minutes for each container, but we might end early. If you've received your insight, you've received the value. The goal is to integrate it.
Who aren't willing to support others.
This isn't a room where everyone shows up just to receive. Brotherhood requires reciprocity, respect, responsibility, and genuine care.

You don't need to have everything figured out. You just need to be willing to show up honestly, take responsibility for your life, and support the men beside you.

Meet your guide

Jomar
Gomez

Coach · Entrepreneur · Husband · Dad

10 yrscoaching founders, executives, athletes, and creatives
$2Mrevenue across my businesses
$5M+of growth for my clients
2kids, one marriage, and businesses he owns and operates today

I've spent over a decade coaching high performers, including founders, executives, and leaders across industries.

I've helped build startups, including one that generated $10+ million in revenue and another that reached a $9 million valuation. Today, alongside my coaching practice, I'm also building and scaling businesses as an owner and operator.

And I'm a husband and father of two.

On paper, I've accomplished some pretty cool things. But here's what I've learned:

Achievement doesn't automatically create peace.

I've experienced burnout, self-doubt, professional setbacks, and the pressure of trying to be everything to everyone.

For years, I believed that success required me to perform a certain version of myself.

  • The confident leader.
  • The successful entrepreneur.
  • The strong husband and father.

But the more I tried to control everything, the further I drifted from myself.

Through ancient wisdom and modern approaches to healing and transformation, I began discovering a different way.

  • I could be ambitious without being consumed by ambition.
  • I could be strong without abandoning my tenderness.
  • I could lead without pretending.
  • And I could pursue extraordinary things without making my worth dependent on achieving them.

That's the work I bring to PLAY FREE.

I'm not here to be your guru. I'm here to coach, facilitate, challenge, and walk alongside a group of men committed to living more fully.

Because I believe real success is the integration of outer excellence and inner peace.

And none of us has to figure that out alone.

Your investment

Nine months. One meaningful mountain.

A brotherhood that has your back. PLAY FREE is a nine-month commitment to yourself, your ambitions, and the kind of man you want to become along the way.

  • 18facilitated group coaching sessions over nine months.
  • 9monthly themes focused on self-trust, courage, leadership, and personal freedom.
  • 1dedicated Journeyman for weekly connection and accountability.
  • ↻Monthly reflection practices and integration exercises.
  • ∞Access to a private community of men committed to growing together.

The full experience $3,200

Pay monthly

$355.56/mo

Nine monthly payments totaling $3,200, with the final payment adjusted to $355.52.

Pay in fullSave $320

$2,880

Save $320 when you commit upfront.

Rolling admissions: joining after the program starts? The monthly option is $450/month. See the FAQ.

By application

Ready to Play Free?

We're intentionally bringing together a group of men who are committed to pursuing meaningful goals while supporting one another along the way.

Because the quality of the men in the room matters, participation is by application or personal invitation.

Already received a personal invitation? You can enroll directly through a private channel available to you.

Questions

Frequently asked

Is this a traditional men's group?

Not exactly.

PLAY FREE combines the depth and connection of men's work with the clarity, accountability, and practical application of high-performance coaching.

We're not gathering solely to process emotions, nor are we simply exchanging business advice. We're creating a space where men can pursue meaningful goals while developing greater self-awareness, confidence, and freedom.

Do I need previous experience with men's work?

You don't necessarily need to have participated in a men's group before.

However, this experience is designed for men who have already invested meaningfully in their personal development and are comfortable with honest reflection, emotional conversations, and receiving feedback.

What if I don't have a clear goal yet?

That's okay.

You should have a general sense that there's something meaningful you want to pursue or change. Part of our early work will be clarifying that vision and translating it into a commitment you can act on.

Is this primarily about business?

No.

Many men in the group may be entrepreneurs, founders, or professionals, but your mountain can involve any meaningful area of life: business, leadership, relationships, fatherhood, creativity, purpose, or personal freedom.

What matters is that you're committed to pursuing something that matters to you.

What if I just need a place to vent and get support?

That's welcome.

You don't have to show up with a perfectly articulated challenge or a major breakthrough to work through.

Some days, you might need coaching. Other days, you might need to get something off your chest, hear another man's perspective, or simply be reminded that you're not alone.

The intention is to create room for both honest support and meaningful action.

Can I join after the program has started?

Yes. PLAY FREE has rolling admissions.

You can join at any point during the nine-month experience, once your application has been reviewed and we've confirmed it's the right fit.

If you join after the program begins, the monthly payment option is $450/month.

What kind of results can I expect?

Each man will establish a meaningful goal or commitment for the nine-month experience.

We'll track progress toward that goal while also examining how you approach challenges, decisions, relationships, and uncertainty. The aim is both external progress and internal growth.

Your specific results will depend on your circumstances, choices, and participation.

How much time should I commit?

Plan for two facilitated group meetings per month, weekly check-ins with your Journeyman, and time for personal reflection and action between sessions.

Consistency matters more than perfection.

Is everything confidential?

Confidentiality is a foundational expectation of the group.

Every participant will be asked to respect the privacy of the other men and keep personal disclosures within the group. We'll establish clear agreements around confidentiality, communication, and mutual respect before beginning.

What happens after nine months?

We'll take time to reflect on what you've accomplished, how you've grown, and what you want to carry into your next chapter.

The intention is for you to leave with stronger relationships, greater self-trust, and practices you can continue using long after the experience ends.

And if you want to continue the journey, you'll have the opportunity to join the next PLAY FREE cohort when enrollment reopens, typically two to three months after your experience concludes.

Because the work doesn't end after nine months. And neither do the relationships you've built.

The invitation

Nine months from now, you could have made meaningful progress toward something you've wanted for years.

  • You might have launched the business.
  • Made the career move.
  • Become a more confident leader.
  • Strengthened your relationships.
  • Or finally stopped allowing fear and self-doubt to make so many of your decisions.

But perhaps the most meaningful change won't be what you've accomplished. It will be how you feel while accomplishing it.

More grounded.More connected.More confident.More yourself.

Not because everything went according to plan. But because you've learned to trust yourself regardless of the outcome.

And you've discovered what becomes possible when you stop trying to do it all alone.

The next mountain is calling. You don't have to climb it the same way you climbed the last one. It's time to Play Free.

Nine months. One meaningful mountain. A brotherhood that has your back.
Build what you want. Become who you are. Enjoy the fucking ride.

PLAY FREE · A 9-Month Men's Experience Guided by Jomar Gomez