Founder & Imagineering Director
Bob Olmstead

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My childhood was hostile. Even terrifying. Which was incredibly painful but I refused to be a victim. I would beat the odds. The chaos had to end. So at the tender age of sixteen, I went out on my own. It’s a miracle I survived but I did survive. 

My saving grace was my vivid imagination. In my mind, I could become anyone. Do anything. The road to success was tough but I persisted. By my early thirties, I was a six-figure executive without a degree. But was that success? Time would tell. 

In the years that followed, I managed two ad agencies, one of which I owned. I did management consulting for twelve years. My income and brand soared. But something was missing. I certainly looked the part but on the inside, I just felt numb and lost. 

In my early forties, I took a crash course on filmmaking. I grew up in The Business so I was curious. My godfather and namesake Bob McCrellis was a Property Master for Paramount for decades. Honestly, the crash course was done on a whim. Why not? My heritage was knocking on the door.

Two shorts films and one play later, the arts had me. Not as an actor but as a Director/Producer. Which included five years of improvisational studies and performing on stage. I was home. Truly home.

The business world stopped working. In truth, I don’t know that it ever worked. My creative passion was always there, expressing itself. As a Creative Director or copywriter. As an imagineer or speaker. Decades of poetry scribbled on notepads. The fantasy saga I’ve been working on for decades. Something. Anything!

When I bumped into the arts in 2006, it spoke to me on a fundamental level. Everything changed. I finally had a voice and platform. Everything felt vibrant and alive. My core DNA was set on fire. 

So, I walked away from the only career I had ever known. It was late 2014 and I was fifty-one years old. Not long after, in a sketchbook, I wrote three words … “The Maestro Experience”. I then circled those three words.

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In “Mozart In The Jungle”, Rodrigo, an orchestra conductor, collaborates with a choreographer and four ballet performers. The choreographer begins with a few personal questions. When Rodrigo responds, the dancers spring to life.

Briefly. Powerfully. Just enough to grab an emotional snapshot. 

Not long after, no music … no words … Rodrigo conducts the four ballet performers. In their raw, primal response, his story. All he had been. All he could ever be

A vibrant mosaic of art, life, and movement. Visceral and pure. No audience. Nothing to prove. All that mattered was the truth that was already there. Rodrigo had everything that he needed. 

In a later episode, he retires his orchestral baton. He finds his own music which kidnaps his body. He begins to dance alone in Central Park, to music only he can hear. The choreographer/Obi-Wan Kenobi, sitting on a bicycle, nods to the moment then rides away. 

Maestro had to become that kind of experience. My life as a survivor. My life as a branding guru. My life as an artist. All my best stuff in a single program. A program that would massively impact creatives, their craft and their lives. 

Maestro is the sacred walk we take together. The truths that already exist. The music that only you can hear. A very human you with a very human me. 

And then it happens. The armor comes down. Progress is made. And with each courageous step, your voice, the things you have to say to the world, begin to rise. 

I look forward to our first chat,
Bob Olmstead


Photographer: Brio Photograhpy

Photographer: Steve Rogers Photograph


  • 650+ Brand Strategy Retreats
  • 20,000+ Consulting/Coaching Hours
  • 7,500+ Professional Writing Hours
  • 700+ Speaking Gigs
  • 25 Years As A Creative Director
  • 20+ Years As A Business Owner
  • 12 Years As A Management Consultant
  • Extensive Experience In Multiple Industries
  • 575+ Hours Of Training In The Performing Arts
  • Director/Producer Of (2) Short Films & (1) Play
  • Graduate Of Two Improvisational Schools
  • Graduate Of Multiple Improvisational Intensives
  • Graduate Of Multiple Filmmaking Intensives
  • 50+ Live Performances As An Improvisational Actor
  • Writer, Blogger, Podcaster, & Vlogger Of (20) Years
  • Producer: Radio, Broadcast, Print, & Online
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I have known Bob professionally for almost (20) years now and I can personally attest to the powerful impact of his teaching and mentoring. His amazing skills in assessment established a personal level of responsibility for leadership, and a reality check for the progress we were achieving. Bob’s message is powerful and direct, compassionate and laser beam accurate.

Mark Becker
The City Of Fort Wayne
(2) Time Deputy Mayor

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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 

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