The Maestro Experience™

The Maestro Experience


Be You! Claim the extraordinary version of what you want to do. Awaken your deepest needs and your greatest talents. Go on an journey of growth like no other. 

Three Indicators That You're Stuck
As An Artist, Creator, Or Innovator

Best Coach For Authors Artists USA

Rabid Demons

Your demons are pounding on the door. What if one gets loose? That CAN’T happen! Then your self-doubt kicks in with vivid reminders of your failures and flaws. What if you’re an imposter? You feel so lost and the noise is exhausting. 

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Intense Overwhelm

You’re very talented. People compliment your work all the time. You earn good money. But you never get to the point where it all just works. You’re constantly getting pulled into the day-to-day. Why does this keep happening?

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Endless Plateaus

Your trailblazing rocks! But why does it rock? Honestly, you don’t have a clue. You kind of get it but not really. Not enough to go to the next level. And that lack of clarity is driving you nuts! You need answers. Good ones!

Speak Your Truth

“If Brene Brown & Gary Vaynerchuck Had A Baby, That Would Be Bob”

Creative Life Coach Bob Olmstead Profile Pic


Creative Life Coach

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Living a creative life, giving birth to bold ideas, earning a living, it can be a tough journey. At times, you may feel invisible to the world. A few questions to consider.

Are you settling for the status quo? Do you have things to say to the world? Do you live your truth without apology? Have you found a platform that resonates and gets results? Is your creative life independent & free?

Raise your voice or stay stuck. That’s the choice you have to make. 

You don’t need to conform. You don’t need to behave. And rebelling against the status quo is a good thing! But you need to bring something real to the table.  

Which is never about “becoming” something. It’s about trusting yourself. It’s about believing in your voice and vision. Only then will your work elevate and set you on fire.

It’s not about the tools. It’s about what you have to say to the world.

Share Your Wisdom


Six wall shattering experiences that will elevate your work and transform your life. A profound awakening of your deepest needs and your greatest talents. 

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Module #1


The Hero’s Journey with you playing the lead role. What’s your backstory? What informs you on a daily basis? What magic do you bring to your work? We begin by clarifying the value you bring to the world on a daily basis. 

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Module #2


Priorities that serve rather than enslave. Feeling fully alive. Meaningfully connecting with your work and life. We continue our work by aligning your decision making process with the things that energize you and give your life and work meaning. 

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Module #3


Running on autopilot, living in reaction, the lifeblood of the status quo. To break free you’ll  learn how to make things happen no matter the odds. The key skills; intention and intensity. Master those and nothing will stand in your way.

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Module #4


Walt Disney’s hallmark talent was doing the impossible. What’s your hallmark talent? In this  barn burner, you’ll learn how to crush your comfort zones as a way of life. To do that, you’ll need to learn how to effectively break the rules to get epic, mind bending results. 

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Module #5


Now that you’re painting outside the lines, it time to craft your Hallmark Experience. This is your Big Move moment, the thing you will become known for as person and/or brand. So we spend a lot of time clarifying how to do that in an authentic, magical, and compelling way. 

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Module #6


The person most likely to sabotage your success is you. Our final expedition focuses on bringing down your armor, honoring your brokenness, and staying in touch with the things that deeply anchor you. It’s kind of like assembling your True North Survival Kit.  

Jody Muniz Nutritional Designs

To call Bob our superhero is an understatement. His “Jedi” senses are wickedly accurate. With his guidance, we now offer the kind of customer experience that used to live only in our dreams.

Jody & Sunday Muniz
Nutritional Designs
Award Winning Nutritionists & Business Owners 

Kareem Badr Improvisor GM Hideout Theater

Bob did an amazing job of rapidly getting to our challenges. The result of our first meeting was the focus and inspiration that would motivate and fuel everything we do. I couldn’t recommend working with him enough.

Kareem Badr
The Hideout Theater
Award Winning Improvisor & Business Owner


It’s not about an egocentric guru holding you accountable, it’s about a shared experience of growth and discovery. 

It’s about the stories you want to tell, the wisdom you want to share, and the projects you want to make happen. 

It’s about owning your authentic voice without apology: personally, professionally, and creatively. 

It’s about handcrafting a platform specific to your passions and talents, whatever that looks like, wherever that takes you.

It’s about honoring your brokenness versus avoiding it, while staying in touch with the things that anchor and feed you. 

Boldly Create Without Apology


I only work with ambitious, committed people. Individuals that are passionate about elevating their craft. Bold imagineers looking for the tools that will help them soar.

If you are willing to invest in your future. If you have a vision or an idea that you want to bring to life. If making a difference matters to you, then welcome home. 

No hype. No get rich schemes. Just a deep dive to unlock your full potential. It’s an experience that will empower you as much as it pushes you. 


Own Your Voice • Elevate Your Craft • Live With Purpose & Passion
$ 675 Monthly
  • A Profound Journey Of Discovery & Exploration
  • Powerful Work On Awakening Your Full Potential
  • Rooted In Your Deepest Needs & Greatest Talents
  • Driven To Find The Big Move That Changes Everything
  • Handcrafted To Shatter The Walls That Keep You Stuck
  • No Quick Fixes. No Get Rich Schemes. No Snake Oil.
  • One (2) Hour Discovery Call To Kick Off Your Expedition
  • Two (60) Minute Phone Coaching Sessions Per Month
  • Ongoing Online Collaboration To Sustain Your Progress
  • (4-6) Deep Dive Worksheets Per Module
  • (2-3) Big Moment Workbooks Per Module
  • (15) Minute Emergency Triage Phone Calls As Needed

The Maestro Experience™ Will Help You Find Your Place In The World As An Artist, Creator, Or Innovator

Dr. Allison Chase Psychologist

Bob seems to “get” human behavior, which makes it safer to deal with the down and dirty stuff that creates road blocks. It was his ability to take me, as a frustrated “worker bee”, and move me into my role as an "owner" that has made the difference.

Dr. Allison Chase
Eating Recovery Center

Karim Currey Social Entrepreneur Digital Artist

Bob knows how creative minds think, and he knows the ins and outs of business. I am a very passionate driven being and I am known to jump from one thing to another on raw passion. Bob was able to quickly reel me in, point it out and sort it out. I am grateful for Bob’s coaching.

Karim Currey
Gifted Multimedia
Social Entrepreneur

Frequently Asked Questions

You listed creative life coaching but The Maestro Experience™ doesn’t sound like coaching? 

Coaching is but one of many tools I use to guide you on this incredible adventure. And that’s what it is, an adventure. An unconventional adventure of discovery and growth that will impact every area of your life. Buckle up! You’re in for one heck of a ride.

Deep Dive Worksheets? What are those? 

Your best discoveries, your greatest breakthroughs, will come from the journey itself. I am but your guide. The Deep Dive Worksheets play a very important role to that end. They facilitate the kind of “aha” moments that set the stage for some epic growth and discovery.  

What is a Big Moment workbook? 

Big breakthroughs rarely happen in a vacuum or randomly. They happen as a result of well fertilized soil. Each Big Moment Experience (which comes with a workbook) has been handcrafted for maximum impact. There are only two to three per module and they always happen at the end of a module. Their primary purpose is to facilitate significant breakthroughs that meaningfully impact your life.  

Online collaboration– how does that work?

Online collaboration is a private, cloud based space where we can chat, share files, assign tasks, and keep the fires of momentum burning. It’s also a great space for asking questions, such as when you’re stuck on a worksheet. Or to get additional support, when you’re feeling a little overwhelmed. 

How long does it take to complete the program?

That varies greatly based upon any number of factors. The typical range is (9-18) months. Honestly, most people don’t want to rush the experience. They end up getting so much from it that whatever it takes, it takes, and they are ok with that reality.

Do I have to sign any contracts?

Yes, I have a standard Letter Of Agreement that must be signed to engage my services. That said, my LOA will not obligate you (financially) to pay for the full term of my program. That’s not how I do business. Meaning, once your monthly or quarterly fee is paid, you are under no contractual obligation to continue.

What happens if we’re not a fit? 

There are two reasons I offer a free Rapid Clarity Call. First, to give you chance to benefit from my expertise free of charge. The second is to determine if we’re a good fit. Personality issues popping up after joining the program are extremely rare.

© All Rights Reserved – Robert Olmstead Enterprises, INC.

The Maestro Experience™  Covers Meaningful Monetization, Personal Branding, & Living A Creative Life That Feeds You | Schedule Your Free Rapid Clarity Call
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