Howard Gray
Seeking the groove.
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Coaching

Coaching isn't advice - it's structured space to discover what you already know but can't quite see yet. Whether you're scaling a venture, stepping into leadership, or navigating a major transition, the right conversations at the right time change everything.

I help creative entrepreneurs and executives turn uncertainty into strategy, ideas into execution, and challenges into opportunities.

Two ways we can work together

Track 1: Strategic Coaching

Big-picture clarity, positioning, and growth

  • Best for: Founders, creatives, and executives navigating inflection points in their career or business.
  • Focus: Strategic clarity, identity, positioning, and scalable growth.

Think of this as calibrating the inner engine - who you are, what you stand for, and where you're going.

Track 2: Groove Theory Coaching

Designing moments that move

  • Best for: Speakers, facilitators, and designers of transformative sessions.
  • Focus: Storytelling mastery, executive presence, and delivery—turning your ideas into live experiences that stick.

This is about the performance layer - how you show up, land your ideas, and make it count when it's live.

Who I work with

I specialize in working with creative professionals who are ready to level up:

  • Founders & Entrepreneurs → From startup founders to independent creators, navigating growth, positioning, and business strategy
  • Creative Professionals → From brand strategists to international DJs, scaling their work and increasing their impact
  • Executives & Emerging Leaders → From agency directors to tech VPs, stepping into leadership and communicating with confidence

How coaching helps

Working together, we can help you:

  • Clarify your positioning & messaging → Get crystal-clear on who you are, what you offer, and why it matters
  • Transform ideas into viable ventures → Turn what's in your head into something real and scalable
  • Master storytelling & communication → Elevate your pitches, presentations, and workshops to world-class level
  • Navigate leadership & career transitions → Step into new roles with confidence - without losing your creative edge
  • Overcome creative resistance & imposter syndrome → Stay in motion when self-doubt creeps in

How we work together

My coaching philosophy

I believe the answers you need are already inside you - my job is to help you access them. Great coaching isn't about giving advice; it's about creating the right conditions for breakthrough thinking. I provide structured space for you to think clearly, challenge your assumptions, and move forward with confidence.

What to expect

  • First Session: We start with a strategic deep dive—understanding where you are, where you want to go, and what's really in the way.
  • Ongoing Sessions: Each session is tailored to where you are in the moment. We might dive deep into strategy, work through a specific challenge, or practice a presentation. Between sessions, you'll have clear actions and accountability.
  • Format: 90-minute sessions via video call (or in-person if you're in NYC). Sessions are focused, practical, and designed to create momentum.

Most clients see significant clarity and momentum within the first month, with sustainable systems in place by month three.

Investment

Strategic Coaching (Track 1)

  • Investment: From $6,000 (3-month minimum)
  • Format: Strategic deep dive + bi-weekly sessions
  • Includes: Personalized action plans, accountability, and frameworks to scale sustainably

Groove Theory Coaching (Track 2)

  • Investment: From $4,500 (project-based)
  • Focus: Developing signature talks, workshops, and presentations
  • Includes: Co-development sessions, delivery coaching, and audience engagement strategies

I only work with a small number of coaching clients at a time to ensure deep, high-impact sessions.

What makes this different

I've been in nearly every seat at the table

I'm not just a coach - I've been an entrepreneur, manager, freelancer, consultant, and employee. I've built ventures, led teams, and worked across startups, creative studios, and Fortune 100 companies. This means I don't just understand business and creativity - I've lived both sides of the equation.

I coach from lived experience

I've felt the highs and lows of launching a business, hitting frustrating plateaus, dealing with creative resistance, and navigating difficult leadership transitions. I coach from experience, not just theory.

Coaching is a craft - and I take it seriously

  • ICF-certified professional coach (Coaching for Transformation, Leadership That Works, NYC)
  • 300+ workshops designed & delivered for Fortune 100 companies, startups, and creative leaders
  • Continuous professional development because this work demands both solid foundations and ongoing growth

My approach is practical and results-driven

  • Practical & Action-Oriented → No fluff, no drawn-out introspection - just sharp insights and real action
  • Supportive but Challenging → I'll push you when needed, always in service of your growth
  • Big-Picture + Tactical → I help you see the system, then act on it

What they say

I started working with Howard during a period where I was dealing with a whole new context and a lot of questions I was trying to work through. I started slightly skeptical about using a coach, but through Howard’s great balance, poise and wisdom, I felt quite safe in exploring these challenges.

Howard is great at asking the right questions in the right way, enabling me to talk my way through issues and nudging me through to these ‘aha’ realisations.

I’ve uncovered and discovered new things, changed thinking and realised that in fact the root of some of my challenges and questions originated from somewhere I did not expect.

Breaking down my next steps into easy manageable accountable actions hugely simplified what was overwhelming before.

– Alex F., Startup Founder, Sustainability

Howard is an absolute master at his craft when it comes to "workshop coaching”. His knowledge and suggestions are brilliant and his guidance has helped me refine and elevate my workshop content. I HIGHLY recommend you work with him - you will be very pleased with the results.

– Jeff Salzenstein - Keynote Speaker & Former ATP Top 100 Tennis Pro

Next Steps