The Maestro Experience™

The Maestro Experience


Own Your Voice. Elevate Your Craft. Live With Purpose & Passion.

To create something extraordinary. Something that matters and stands out. The people that aspire to that level of impact are the maestros of the future.  Artists to business owners. Authors to social entrepreneurs. Creators of all types …

Three Indicators That You're Stuck

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. 

Coaching Authors Los Angeles

Intense Overwhelm

You’re talented. People compliment your work. They hire you. But you never get to the point where it all just works. Some problems never get fixed. It’s as though the world is speaking in a language you’ll never understand. Why is this happening?

Coaching Authors Austin

Endless Plateaus

Your trailblazing rocks! But why does it rock? Honestly, you don’t know. You kind of get it but not really. Not enough to go to the next level. And that lack of clarity and progress 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

Tiny Buddha Bob Olmstead Creative 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 your 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 good thing! But you do 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 you build the kind of creative life that will 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 powerhouse experiences that will empower you to live & create from a place of purpose & passion. A heartfelt journey that will impact every area of your life.

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Module #1


The Hero’s Journey with you playing the lead role. What’s your backstory? What informs your decisions on a daily basis? What anchors your view of the world? This module gets to the very essence of the value and wisdom you bring to the world in all areas of life. 

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Module #2


Good self care. Priorities that serve rather than enslave. Feeling fully alive. What moments fill you with a deep sense of meaning & connection? What sets every fiber of your being on fire?  This module will help you get fed personally, professionally, and creatively. 

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Module #3


Autopilot is not your friend. Nor is living from a place of reaction. It’s how you end up stuck in the rat race. The key shift is habitually taking purpose-driven actions. In this module, you will align what you want with how you live, lead, & create. 

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Module #4


Walt Disney’s brought his cartoons to life in the form of Disneyland. If there were no rules, what would your big move be? What’s standing in the way of you doing that now? In this module, you identify in great detail, the big move that will change everything. 

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Module #5


How to bring your big move to life in a vivid and powerful way? It’s time to start a wildfire! Think about your audience. What would blow their mind? And how to do that in a way that deeply connects? In this module, you will handcraft the experience that becomes the hallmark of your brand. 

Best Creative Life Coach Seattle

Module #6


The person most likely to sabotage your success is the person in the mirror. How to stop getting in your own way? How to embrace success? In our final module, we zero in on honoring your brokenness and staying anchored to the things that matter most. 

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
$ 475 Monthly
  • Comprehensive Creative Life Coaching
  • Powerful Work On Your Craft & Platform
  • 100% About Your Deepest Held Passions & Talents
  • Designed To Break You Free Of The Status Quo
  • No Quick Fixes Or Get Rich Schemes
  • One (90) Minute Discovery Call To Kick Off The Process
  • Two (60) Minute Phone Coaching Sessions Per Month
  • (4-6) Deep Dive Worksheets Per Module
  • (2-3) Big Moment Workbooks Per Module
  • Ongoing Online Collaboration To Sustain Your Progress
  • (15) Minute Emergency Triage Calls

Are you looking for more comprehensive support? Upgrade to weekly calls at $900 a month or save $300 every (3) months by paying $2,400 a quarter. 

The Maestro Experience™ Will Help You Find Your Place In The World In A Real & Tangible Way

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.

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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