Anthony Matacotta

About Me

Hi, I’m Anthony, founder of To The Sky Coaching—where you're never meant to navigate life’s biggest transitions alone. For over a decade, I’ve served as an officer and aviator in the United States Marine Corps, leading in high-stakes environments where clarity, confidence, and courage weren’t optional—they were essential. Now, I help ambitious professionals, leaders, and those at major crossroads reclaim that same sense of direction in their personal and professional lives.

My path to coaching wasn’t a straight line. It was born from living the exact struggle many of my clients face: outward success, inner dissatisfaction. Despite rank, recognition, and responsibility, I felt stuck—disconnected from the life I should want and craving something more real, aligned, and free.

That internal turbulence led me to study transformational coaching, human performance, and the psychology of fulfillment. I worked with powerful mentors and read the best minds in the industry. Then I tested everything in my own life.

The result? I learned how to chart a new course—and now I help others do the same.

Coaching with me

Results & Goals

What You Get

1. One-on-One Private Coaching Sessions

Each 60-minute session is tailored to you and guided by a proven methodology rooted in leadership psychology, confidence science, and real-world strategy. You’ll be challenged, heard, and stretched.

2. The Flight Plan: Custom Growth Framework

After our first deep-dive session, you’ll receive a personalized "Flight Plan" that outlines your goals, blind spots, and a development path built around your values and ambitions.

3. In-Session Breakthrough Tools

From silence to metaphor to bold reframes, I use master-level coaching techniques to help you get under the surface of what’s holding you back—and launch you toward lasting change.

4. Between-Session Access

You don’t grow on a schedule. That’s why you’ll have access to me via messenger or email between sessions for those moments when you need a quick recalibration or reminder of your power.

5. Strategic Leadership Support

Whether you’re navigating a promotion, managing a team, or making a pivot, you’ll have a seasoned leadership expert in your corner—someone who understands what it takes to lead in high-stakes environments.

Why This Coaching Works

Most confidence and leadership problems are not solved by reading more books or faking it until you make it. They’re solved by:

Getting radically honest about what you want.

Breaking the beliefs that keep you small.

Taking action with aligned courage.

I help you do exactly that. This is not therapy, mentoring, or life advice. This is transformational coaching—a guided, focused journey where you shift who you're being so you can change what you're doing.

How I like to coach

I’m not here to give you all the answers—but to help you see the ones already inside you. I sit beside you, not above you. I challenge you without ever judging you. And I don’t let turbulence keep us from reaching cruising altitude.

I coach from a place of deep presence, direct truth, and real respect. You’ll get honesty without ego, encouragement without fluff, and structure without rigidity. You won’t get a script, a workbook, or a one-size-fits-all formula. You will get a highly customized, high-trust experience where we explore what’s real, what’s possible, and what’s next.

What it feels like to coach with me:

• Grounded but bold. I hold space for real reflection and real action. You’ll leave each session with new clarity—and often, a next step that feels both scary and exciting.
• Challenging but safe. I’ll call out the patterns keeping you stuck, not to expose you—but to set you free. You’ll never be shamed, but you will be stretched.
• Focused on who you're becoming. I’m not here to fix you. I’m here to help you see the leader, partner, creator, or human you’re becoming—and claim that identity with confidence.

Bottom line?

I believe you're capable of more than you think—and I’ll never stop holding that belief, even on the days you can’t see it yourself.

Offerings

Coaching

I offer one-on-one coaching in two core areas: Leadership Coaching and Confidence Coaching. Both are designed to help you break through stagnation, align your actions with your values, and take bold ownership of your life and career.

Leadership Coaching

For professionals, executives, and aspiring leaders who want to sharpen their leadership presence, navigate transitions, or step more fully into positions of influence.

You’ll get:

• 60-minute private Zoom sessions
• Clarity on your leadership identity and goals
• Real-time feedback and practical strategies
• Between-session support via email or voice message
• Optional leadership assessments or exercises tailored to your role
• Available as:
• Individual sessions
• 4-,6-, and 13-session packages for deeper transformation

🔥 Confidence Coaching

For individuals feeling stuck, uncertain, or disconnected from their inner power — whether in career, relationships, or self-image. We’ll work to dissolve limiting beliefs like imposter syndrome and build lasting, grounded confidence.

You’ll get:

• 60-minute private Zoom sessions
• A personalized confidence roadmap
• Tools to rewire self-doubt and imposter syndrome
• Between-session support to help integrate insights
• Available as:
• Individual sessions
• 4-, 6-, and 13-session packages for sustainable growth

Professional and life experience

While I don't hold a formal coaching certification, my clients don’t come to me for textbook techniques — they come for grounded insight, leadership clarity, and transformation that sticks.

I bring over 12 years of leadership experience as a U.S. Marine Corps officer, where I’ve led teams in high-stakes environments, made life-or-death decisions under pressure, and mentored service members through career and personal crossroads. I’ve flown missions around the world as a helicopter and transport pilot, and now serve in a strategic leadership fellowship in the U.S. Senate — a position earned through trust, performance, and character.

I'm also a husband, father, and committed student of personal growth. I've studied the work of transformational thinkers, ancient and contemporary, and bring that same depth of presence and inquiry to every coaching conversation.

My coaching style is not about telling you what to do. It’s about helping you see what’s really possible — and then supporting you as you rise to meet it.

Fee description

I offer coaching on a session-based model so you can scale your investment based on your commitment and goals.

• Individual Session: $99
• 4-Session Package: $350 ($87.50/session)
• 6-Session Package: $499 ($83.17/session)
• 13-Session Package: $999 (76.85/session)

Each session is 60 minutes, held via Zoom, and includes follow-up support by email or voice message between sessions.

Military members and veterans receive a 25% discount on all packages.

If you're not sure what's right for you, let’s connect for a free 30-minute discovery call