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My childhood was hostile. Even terrifying. Which was incredibly painful but I refused to be a victim. I had to 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. 

My saving grace was my vivid imagination. In my mind, I could 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 became a management consultant for twelve years. My brand soared along with my income. But something was missing. I certainly looked the part but on the inside, I just felt numb and very lost. 

In my early forties, I took a crash course on filmmaking. I grew up in the film business so I was curious. My godfather and namesake Bob McCrellis was a Property Master for Paramount for decades. Honestly, the whole thing was done on a whim. But 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 world of business stopped working. In truth, I don’t know that it ever worked. My deep need to make a difference was always there, expressing itself. Same with my creative side. As a Creative Director or copywriter. As an imagineer or speaker. Decades of poetry scribbled on notepads. The many young people I’ve mentored over the years

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 become.

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 to make the world a better place. A program that would massively impact the changemakers of the world. 

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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