A Profound Awakening Of Your Deepest Needs & Your Greatest Talents

The Maestro Experience For Creative Entrepreneurs

The Maestro Experience ™ is impossible to describe. It’s not coaching, training, a workshop, an intensive study, a spiritual experience and yet, it is all of those things and much more. 

(3) BIG Indicators That You're Stuck


Somewhere along the way, you got lost in the Status Quo. That mind numbing prison called the day-to-day. While the people may say you’re fantastic, you feel dead inside. You’re on autopilot, going through the motions.


Passion is your fuel. You crave work that sets you on fire. But lately, that has not been happening. And daily dull is not your thing. What’s missing? How did you end up here? And how can you break free? Life is short and the boredom thing ain’t working.


Long hours. Hard work. You always bring your best to everything you do. Yet, no results. What the hell is going on? The price of hard work with poor results is starting to get too high. Something has to give. You need real solutions that get results without selling your soul.

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Immerse yourself in your ideas and craft

Awaken your deepest needs and your greatest talents. That’s The Maestro Experience™ but without requiring a traditional sabbatical. Lewis Carroll said it best when he wrote (in Alice In Wonderland), “Have I gone mad? I’m afraid so. You’re entirely Bonkers. But I will tell you a secret, all the best people are.”  Welcome to an experience that breaks the rules and ventures into uncharted territory. 


Explore don’t fix. Constantly fixing things will offer little benefit. What is your current situation trying to teach you? Get curious. Take your time. Ask tough questions. Open new doors. Unlock the deeper truths that will take your life and craft to a whole new level. 


When your pain and your passion become powerful allies, you are born anew. Your life, talent, and impact expand. Your sense of purpose grows. Expanding oneself is willingly shedding one skin to take on another. It’s remaining true to yourself while becoming something more. 


As artists, creators, and innovators, we bring things to life. Art. Change. Brands. And so much more. We succeed and we fail. We rise and we fall. And from this process, we learn. We grow. Our craft elevates to a new level and then … the process repeats. As you create, you are created. That’s how it works. 



Give Birth To Your Best, Most Daring Life And Work

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We hear the advice all the time, speak and live your truth. But what does that even mean? Values or having a mission don’t even come close. What PROFOUNDLY informs you personally? Professionally? Creatively? Our first walk together will focus on achieving absolute clarity on who you are and what you need on a very deep and real level. Clarity is power. 

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Establishing priorities that serve rather than enslave your daily life. Meaningfully connecting with the people and things that consume your time. Getting into The Zone when needed. Our second walk together will focus on bringing more energy and meaning into your life. As that happens, getting fired up will be replaced by being fired up as a way of life.

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Running on autopilot. Constantly reacting versus getting some perspective. Working hard versus working smart. That’s how you stay stuck. In our third walk together, you’ll learn how to beat the odds and get stuff done. It all comes down to intention and intensity. Master those and you’ll be able to accomplish almost anything.

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Maestros are known for their bold moves and their incredible work. That’s how they build powerhouse brands. Yes, there’s a bit more to it than that but, those are the two KEY ingredients. Our fourth walk together will bring those traits to life in your leadership and brand. And we’ll do that in an authentic, compelling, and magical way.   

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The person most likely to sabotage your success? You! Our fifth and final walk together will focus on the three habits most critical to your success practice: bringing down your armor, honoring your brokenness, and staying in touch with the things that anchor you. These three habits will keep you on solid ground no matter how successful you do or do not become. 

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


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

Maestro is the things you want to create, the wisdom you want to share, and the impact you want to have. 

Maestro is claiming your authentic voice without apology: personally, professionally, and creatively. 

Maestro is breaking down walls, raising your voice, and facilitating the change you seek.  

Maestro’s primary purpose is to inspire an awakening that opens the door to your best, most daring life and work. 



I only work with motivated, committed people. Individuals that are passionate about living the best version of their lives. Bold imagineers looking for tools to do their best work.

Are you willing to invest in your future? Do you have a passion to bring to life? Does making a difference matter to you? Do you like to push your comfort zones? If yes, then welcome home. 

No hype. No get rich schemes. Just a deep dive to unlock your full potential. A heartfelt experience that will help you explore, expand and create in a way that will forever impact your life. 


Give Birth To Your Best, Most Daring Life & Work
$ 650 Monthly
  • A Profound Journey Of Discovery & Exploration
  • Powerful Work On Awakening Your Full Potential
  • Rooted In Your Deepest Needs & Greatest Talents
  • A Process That Will Greatly Elevate The Strength Of Your Brand
  • 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 Sabbatical
  • Two (60) Minute Phone Coaching Sessions Per Month
  • Ongoing Online Collaboration To Sustain Your Progress
  • (4-6) Deep Dive Worksheets Per Expedition
  • (2-3) Big Breakthrough Workbooks Per Expedition
  • (15) Minute Emergency Triage Phone Calls As Needed
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 list various time frames, why is that? 

People progress at different rates. This program allows for and even encourages taking your time. Remember, this is a part-time sabbatical not a quick fix, so I give yourself the time you need to get the results you are looking for. 

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  facilitate growth and set the stage for our Big Breakthrough process.  

Big Breakthrough Workbooks? What are those?

Big breakthroughs rarely happen in a vacuum or randomly. They happen as a result of well fertilized soil. Each Big Breakthrough Workbook (which comes at the end of each expedition) has been handcrafted for maximum impact. Their primary purpose is to facilitate the kind of growth that will significantly  impact your life and work. 

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 (12-22) months. Honestly, most participants don’t want to rush the experience. They end up getting so much from each expedition that whatever it takes it takes and they are ok with that process.

Do I have to sign any contracts?

Yes, I have a standard Letter Of Agreement that is required to join the program. 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 beyond that amount of prepaid amount of time. 

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 Maestro and our personalities are a good fit. Personality issues popping up after joining the program are extremely rare.

© All Rights Reserved – Robert Olmstead Enterprises, INC.

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