Founder & Creative Coach
Bob Olmstead

My childhood was hostile. Terrifying. But I refused to be a victim. I had to beat the odds no matter the price. The chaos had to end. At the tender age of sixteen, I was 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 doable. By my early thirties, I was a six-figure executive without a degree.

In the years that followed, I managed two ad agencies, one of which I owned. After 9-11 crushed my firm, I launched a management consulting practice. My income doubled. My personal brand soared. But something was missing.

I had no Ikigai. No rooted sense of purpose or passion. I looked successful but on the inside, I felt dead. On a whim, I took a crash course on filmmaking. The draw was Bob McCrellis, my godfather. He passed when I was young but “The Business” engulfed me as a child. My heritage was knocking on the door. 

Two shorts films and one play later, the arts had me. All of 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 a strategist or speaker. Decades of poetry scribbled on notepads.

I was always creating. Something. Anything!

When I jumped into the arts in 2006, it spoke to me. Deeply. Fundamentally. Everything changed. Everything seemed to come to life. 

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.

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. And in their raw, primal responses, 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 surrenders his orchestral baton. He finds his own music, which kidnaps his body. He begins to dance. Alone. In Central Park. To music that only he can hear. The choreographer, on a bicycle, notes 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 manifesting 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 find. 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, begins to rise. 

I look forward to our first chat,
Bob Olmstead

Photographer: Brio Photograhpy

Photographer: Steve Rogers Photography


  • 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
Mark Becker Fort Wayne

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

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 

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