Act III

WMMM #001 - Act III

Cardinal Initiatives Newsletter January 28, 2023 3 min read


Shakespearean plays are known to follow a five-act structure:

Prologue, Conflict, Rising Action, Falling Action, and Denouement or Resolution.

And while I have faith that He has a plan for me, it feels like I am beginning Act III of my career and life.

I now see Act I was growing up in the Midwest (Peoria. IL), the move to Dallas, Texas, and Early Career character development. The critical conflict was transitioning from a technical role to a sales role. Learning to sell was a significant obstacle.

Ironically, one of the best sales systems I experienced uses this saying in their training:

“…enterprise sales is like a Broadway play put on by psychologists.”

It is fitting to express my journey now using theatre terms.

Marriage and the birth of our first two children also played a significant role in my development during this period. Adding the roles of husband and father is life-changing for sure.


Act II, Middle Career, is where I transitioned from individual contributor to sales management and leadership.

But first, I tasted success as a salesperson; lighthouse wins, and Club trips.

It was soon followed by failure as I went from selling in defined markets to early-stage startup software players.

Our third and fourth children were born, and then the 19-year run with Oracle likely made this the defining period of my life.

Leaving Oracle would have made for the perfect Final Scene of Act II. But life is messy, and so is the ending of Act II.

Nineteen years had allowed our two oldest to graduate college and begin lives on their own. We still had our two youngest at university, and I still had startups in my blood. I tried another that lasted almost three years and infamously tanked after reaching unicorn status.

I decided to go out on my own as an entrepreneur offering sales performance consulting. I had picked up a couple of clients when Google called with an offer “I couldn’t refuse.” For sure, I could have refused, but I didn’t.

Google is a wonderful company, but it was not mature enough in the enterprise sales game – it was not ready to have done what it had hired me to do for them. Three years later, we parted ways.

I would not trade these seven post-Oracle years for anything. I learned so much and upgraded my skillset. With all four children now out on their own, the stars are aligned for my next Act.


Act III is supposed to be the turning point of the play, characterized by Rising Action and ending with The Climax before the third Intermission. We will see; it is undoubtedly starting that way.

My Act III is transitioning from the corporate world to Entrepreneur.

I began by awakening my network with some blogging and phone calls. I revived my sales performance consulting company and began advising an investor in my network and a cybersecurity startup.

Leadership roles with well-funded startups have caught my eye a couple of times. I confess that I paused to speak with them, justifying to myself that I was only doing this as business development for my consulting business.

But I found a new world and am convinced I need to immerse myself in it as part of my business: the online audience and digital products made from my IP.

Cardinal Initiatives now has three initiatives: Advisory, Coaching, and Digital.

I now see why this is the perfect fit for me.

When I think about what I want, here is where I’ve landed:

- meet and help as many people as possible in the time I have left in my life

- spend my time how I choose, when, and with whom I choose to do so.

Building a digital business compliments the other two and expands my reach beyond the people I’ve met and the relationships I’ve made.

Acts I and II contain an enormous amount of IP that others find helpful. And I am learning so much, and with such a large population attempting to create different lives for themselves, sharing my journey in Act III, in real-time, as I experience it, will only add to the value received.

Tips, techniques, best practices, or hacks, call them what you want; I will share them weekly in this Newsletter.

Thanks for reading.


Whenever you are ready, there are 3 ways I can help you:

- Advisory: my time helps Early-Stage technology companies with sales performance

- Coaching: my time helps salespeople perform their best

- Digital: my online content helps business owners and sales professionals.

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