Maestro Founder & Trail Guide
Bob Olmstead

My childhood was hostile. Chaotic. Even terrifying. But I refused to become a statistic so, at age sixteen, I was out on my own. Looking back, it’s a miracle I survived.

In the adult world, I became an overachiever because it opened doors. In my 20’s, that happened in sales & marketing. In my 30’s, senior management. In my 40’s, management consulting.

It took me (15) years to go from troubled teen to earning six-figures without a degree.

Apparently, anything was possible!

In Episode 3, Season 4 of, “Mozart In The Jungle”– Rodrigo, an orchestra conductor, collaborates with a choreographer and four ballet performers. It’s an experiment of sorts. 

The choreographer asks a few personal questions of Rodrigo. The ballet dancers then responded to his answers– briefly, organically, physically. That was rehearsal. Nothing more.  

Using only his orchestral hand movements, the personal stories he had shared, no music … Rodrigo conducts the ballet performers. 

It was breathtaking.

The perfect blend of art with life with movement. And it was so visceral and pure. No audience. Nothing to prove. All that mattered was the truth that was already there.

I was spellbound. 

Every nuance. Every detail. Every beat. I experience life in moments. I still do. It’s how I process the world. And that’s when it hit me. 

Maestros master the moments. 

Maestros of fine dinning. Maestros of performance and art direction. Maestros of paint and the written word. Maestros of social justice and activist retail brands. So many others. 

It all came down mastering the moments. Once that hit me in 2015, I had to teach these concepts. But I wanted to do that in a way that was, in and of itself, an incredible experience. 

When I first started creating Maestro in 2015, the idea was simple. I wanted to help everyday visionaries give birth to their best, most daring life and work. That was it. But how? It had to be magical.

Three years later, Maestro as a wild ride creative sabbatical was born. A program that easily fits into people’s lives without sacrificing it’s impact. Unconventional. Life changing. 

Ultimately, Maestro is the sacred walk we take together. The things we explore. The things you make your own. The truth you find and speak. The talent you claim. The fears we face together.

But still, it’s about the walk. That’s where the magic happens for you and for me. On the path. Exploring. Testing out ideas. Stretching your comfort zones. Having a safe place to land.  

The truth is, we’re all explorers and we’re all scribes. 

I look forward to talking soon,
Bob Olmstead


  • 655 Brand Strategy Retreats
  • 18,577 Hours As A Consultant/Coach
  • 2,776 Hours As A Copywriter
  • 720 Speaking Gigs
  • 20 Years As A Business Owner
  • 25 Years As A Creative Director
  • Producer In Radio, Broadcast, Print, & Online
  • 581 Hours Of Training In The Performing Arts
  • Director/Producer Of (2) Short Films & One Play
  • Graduate Of Two Improvisational Schools
  • Graduate Of Multiple Improvisational Intensives
  • Niche Focus In Experimental Film & Theater
  • 52 Live Performances As An Improvisational Actor
  • Writer, Blogger, Podcaster, & Vlogger Of (10) Years

The Well Runs Deep For Authors, Artists, & Creatives

Your backstory. The truths that inform your life and work. Your greatest passions. The things that bring energy and meaning to your life.

You are the well. The things I just listed– the water within. So taste the water!

Your deepest needs, your greatest talents, will NEVER be found in a mastermind program. And this goes WAY BEYOND some simplistic view of purpose. There is far more to you than meets the eye. Maestro dares to explore that truth. 

When push comes to shove, who are you? What are you about? What defines you personally and professionally? What makes you feel like a rock start? Important questions that most people never ask. 

Bold is not something you invent. And it has nothing to do with being an introvert or an extrovert. It’s simply going to the beat of your own drum. That’s it. To hell with convention, you’re cool being you. Bold is being comfortable in your own skin.

And that is what Maestro is all about. But how was Maestro born?

In 2015, I was a high profile six-figure management consultant with a reputation for getting results. My Secret Sauce was caring with candor. I was the hard ass big brother that always had your back. 

I’ve worked with small businesses, cities and counties, law firms, wholesalers, retailers, PR firms, and many others. Unfortunately, I was slowly dying inside. After (25) years of being a road warrior, I was done. 

While sitting on an airplane in 2015, snow falling on the wings, tears crept down my cheeks. I hit a wall. I just couldn’t be the elite triage guy anymore. The party was over. 

Emotionally dehydrated, I craved meaning and connection. It was time to make some very big changes in my life. In 2015, I begin testing business models, A LOT of business models, around the Maestro concept.

In the fall of 2017, I launched an Aplha version with my hard launch happening in January 2018. The rest is history. I am head over heels in love with this program! Why? Because I get to watch people grow far beyond what they ever thought possible. 

Thanks for visiting my Website,

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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