The Maestro Experience™

Seriously ...

Creative Coach Life Coach Bob Olmstead Austin TX


Life is short. Cherish the moments. 

Like the time I was in a high rise office building looking down at the city below. My client, a law firm with (25+) lawyers, had the top three floors. And there I was, a management consultant without a degree, doing my thing. 

It was long ways from being on my own at age sixteen. 

Tears welled up. I have long refused to become a statistic, but to be standing there, face-to-face with that level of success? It was a moment beyond words. 

And so I have a soft spot for underdogs. I take little for granted. And I get people’s pain. Their struggles. I’ve been there many times. 


  • 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
  • 581 Hours Of Training In The Performing Arts
  • Director/Producer Of (2) Short Films & One Play
  • Graduate Of Two Improvisational Schools
  • Niche Focus In Experimental Film & Theater
  • 52 Live Performances As An Improvisational Actor

It’s all about Connecting & Creating. 

I was directing a rehearsal for Breaking Beckett when a member of our production team got triggered. Nothing dramatic. It just was a very human, very real moment. In an instant, the cast gently pulled him onto the stage and we showered him with support and love.

Moments. Really good, totally bad ass moments.

Whether I’m teaching a workshop or working  one-on-one with someone, there is this shift that occurs. Walls start collapsing. The real stuff bubbles up to the surface. Dreams. Fears. Insecurities. The desire to create. The desire for meaning. 

And so there we are, imperfect beings, imperfectly walking the path together. The path of life. The path of discovery. The path of letting go. 

It’s a humbling experience but it’s also a massive high for me. I’m in the zone. I’m doing what I do best; helping creatives break free from the BS and soar.

It’s called coaching, personal branding, or some other label. But really, those labels don’t even come close. The experience is far more sacred and powerful than that. It seeing in others what they don’t (yet) see in themselves.

Until one day, they do. And I get to be there when that happens.

That’s the payoff for me. That’s why I do what I do. 






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

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