Creative Business Coach
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 learned being an overachiever opened doors. In my 20’s, that happened in sales. In my 30’s, senior management. It took me about (15) years to go from troubled teen to earning six-figures as a senior manager. And I did that without a degree.

Apparently, anything is possible!

In Episode 3, Season 4 of, “Mozart In The Jungle”– there is this scene that set my brain on fire. In it, Rodrigo, an orchestra conductor, collaborates with a choreographer and four ballet performers.

The scene peaks when Rodrigo starts conducting the ballet performers using only his orchestral hand movements. No music.

Informing their improvised choreography, the personal stories Rodrigo had shared prior to their rehearsal. 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 see the DNA of moments. I still do. It’s how I process the world.

Maestros master the moments. 

Moments found in dining and food. Moments found in performance and captured on film. Moments captured in the written word. Many others. 

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

Then it hit me … a part-time creative sabbatical. A program where everyday people with ideas and ambition could awaken their deepest needs and their greatest talents.

When I first started creating Maestro in 2015, I had one idea in mind. I wanted to help everyday creatives and visionaries give birth to their best, most daring life and work. That was it.

In many ways, Maestro is the sacred walk we take together. You have things to explore and make your own. You have truths that need to be told. You have talent beyond what you realize.

You have fears to overcome. But still, it’s about the walk we take together. That’s where the magic happens for both of us. On the path. Walking the walk. 

We’re all explorers and 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 origin story. Your talent. The truths that inform your life and work. The passions that you go all in on. The things that bring energy and meaning to your life.

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

Plug into your inner world on a far deeper level than values and mission statements. The hidden gold within will NEVER be found in a mastermind program.

When push comes to shove, who are you? What are you truly about? No walls. No armor. No B.S. What defines and drives you personally and professionally? Important questions.

The big takeaway? Live your truth without hesitation or apology.

Bold is not something you invent. It has nothing to do with being an introvert or an extrovert. It’s simply going to the beat of your own drum wherever that takes you.

Which is why the most challenging expedition in Maestro is the first one, Live Your Truth. It’s a DEEP DIVE into who you really are and what you’re really about. The stuff that TRULY defines and moves you as a human being.

It is not easy work but that’s ok, it’s life changing, deeply satisfying work.

But how did all this come to pass? How was Maestro born?

In 2015, I was a high profile six-figure management consultant with a reputation for being a hard ass. I would go toe-to-toe with just about anyone. Which worked out well. My clients respected my candor because it got results.

I’ve turned many 500–700K firms into 3–5M firms over the years. My clientele has included small businesses, cities and counties, law firms, wholesalers, many others. And slowly, as the big checks got cashed, I was dying inside.

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

Emotionally dehydrated, I craved meaning and connection. Everything had to change! And so my journey began. A very tough journey with many highs and lows. The first result was Maestro, alpha launched in the fall of 2017. 

My greatest hope for you, whether that be through Maestro or another program, is that you, too- would find the well that runs deep. And in a moment of courage, you too, might taste the water and be set free.

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

© All Rights Reserved – Robert Olmstead Enterprises, INC.

Close Menu