CEO Advisory

Big Red Car here.  The Boss advises selected CEOs — startup and small/medium business CEOs.  Let me tell you a bit about what he does and how he does it.

He is currently working with about fifteen CEOs from a broad cross section of industries, locales and countries.

The Boss

The Boss is an experienced, seasoned and salty Chief Executive Officer and President of public and private companies in a number of different highly regulated industries.

He has been a founder, entrepreneur, President, CEO and Director for over 33 years.  In that time period, you learn a bit about running a company.  Much of what a young CEO might struggle with, The Boss has done literally hundreds of times.

He has also founded and served as a President, Chairman or Director of numerous public service and charity Boards of Directors.  These have included a foundation of a public university, a State agency, a major arts organization, a major medical clinic, a substantial youth intervention undertaking and a neighborhood association.

The Boss understands the role of Directors in a public company, private company and public service environment.  He knows how to work with Boards and how Boards can work effectively with management.

The Boss is an experienced CEO and Director.  He understands business in the Internet age.

How does The Boss help a CEO?

There is no substitute for learning from experience but you don’t have to pay full tuition to acquire that education.  You can harness The Boss’s experience and expertise like a rented mule.  Haha, the Big Red Car is never really serious.  OK, tone it down, Big Red Car.

CEOs need someone who can work directly with them who does not have the conflict of being an investor or substantial shareholder.  The Boss works exclusively with the CEO and is beholden only to the CEO.  In this matter, The Boss and the CEO can work on things which a prudent CEO cannot share with his Board, Venture Capitalists or largest shareholders.  This is a hard truth and every CEO understands the importance of such an objective advisor who only has the CEO’s interests at heart.

The CEO is getting someone who has been in that seat, has wrestled with those demons and who intimately understands the powerful forces swirling around that chair.

Sometimes a CEO needs to discuss things of such a personal and intimate nature that he cannot get real world advice unless his advisor has walked in those mocassins.  That is The Boss.

Everything is completely confidential and will never be shared with anyone other than the CEO.


The Boss is going to be able to assist you with the building blocks of any startup or small/medium business — Vision, Mission, Strategy, Tactics, Objectives, Values, Culture.

Take a look at this blog post <<< link  to get a sense of how The Boss approaches such issues.

The Boss will be able to apply real world expertise, not theory that is untested.

Vision, mission, business model, planning, strategy, tactics, objectives, hiring, compensation design, benefits administration, performance appraisal, employment agreement, mentoring, coaching, talent development, training, communication, organizational development, financial planning, marketing, technology, litigation, legislation, lobbying, regulatory contact, Board relations, real estate — The Boss has done it and will help you do it but without the necessity to break a sweat or a fingernail.  In 33 years, you learn a few things and even some damn good tricks.

Take a look at this blog post to get a sense of how The Boss would approach compensation <<< link.

Take a look at this blog post to get a sense as to how The Boss would approach the basic Business Model <<< link of a company.

 These are all pragmatic and real world solutions that can be tailored to your specific situation.


Over 33 years of CEO-ing, you are going to develop and collect a long list of exemplars — documents, graphics, processes and writings which are going to cover a lot of what a new or even an experienced CEO is going to be doing.

The Boss will share these exemplars with you and help you tailor them to your personal advantage and use.

There is no reason to re-invent the wheel.

Here is an example of a graphic which outlines how a startup or growing company might consider growing into its sea legs on the issue of financial talent.  Click on the graphic to increase the size.

The Boss has hundreds of such examples.  Again, in 33 years of running businesses, you learn a few things and stop constantly re-inventing the wheel.


Typically The Boss and the CEO will lay out a methodology of communicating using email and phone and Skype.  Typically they will visit once a week on Skype, usually on a set day of the week.

There will be a set agenda — set by the CEO.  The Skype call will typically take 1-2 hours weekly (or at the frequency the CEO requires) and will only conclude when the CEO is ready to move on.

At the end of the call, The Boss will prepare a Memorandum outlining what he heard, making any suggestions as to follow up actions and identifying any parking lot issues to be re-visited.

At the next call, the CEO and The Boss will make a quick review of the Memo and then guide the conversation along the agenda set by the CEO.

It is totally informal but structured to ensure that the CEO’s time is used effectively.

This can be done early in the morning, late at night — whatever works with the CEO’s duties, energy and time zone.

It is not The Boss’s intention to be one more pain in the CEO’s butt or to assign homework.  The Boss will do a bit of work himself outside of the conference and Memo.

The Boss likes to focus on graphics that can guide the conversation — talking about hiring is best guided by looking at the organizational chart.  When a graphic does not exist, The Boss will assist in creating one.  Talking about sales — look at the sales process flow chart and pipeline.

Advisory service, mentoring, coaching

The Boss provides CEOs with advice which about every aspect of running a startup up or small/medium business.  Some folks call this “mentoring” but, in fact, mentoring implies a much broader and personalized service dealing with both business and personal interests.  The Boss can provide those kind of services but most of his advice is strictly related to business and the personal implications of being a CEO.

Coaching is the development of a specific skill or talent.  Subsumed within the nature of the advisory relationship are a myriad of opportunities to explore and develop a specific skill.

Call it what you will, The Boss will provide you with the assistance you need to awaken your inner Lion.  He’s in there, I promise.


The Boss typically is contracted by the CEO and charges $1-2,000 per month.  It is typically never more but it could be less.

When the Boss is contracted by a VC (still only offering his allegiance to the CEO), he charges $1,500-2,500 per month.  It is typically never more but it could be less.

When the Boss is contacted by a VC and serves the interest of the VC exclusively, he typically charges $250/hour.

This arrangement is not cast in stone and it may ebb and flow with the needs of the CEO.  A time may come in which a CEO has a very high short requirement and it may change over time.

The CEO and The Boss will know the right fit and when they need to revise the arrangement they will chat and make it so.

No contracts, just a handshake — a monthly invoice and a check.


Here is what clients and others have had to say:

Aaron Klein, Co-Founder and CEO of Riskalyze (27 April 2013):

“I consider Jeff to be one of the greatest CEO coaches of all time.  He will challenge you, call your bluff, and infuse your thinking with fresh ideas on the strategic and tactical.  If you have the chance to work with him, trust me — seize it immediately.”

Henry Yates, Founder and CEO of Estate Create, London, England ( 4 March 2013)

Testimonial JLM Henry Yates <<< click on link


If you need to speak with The Boss, give him a call on his cell phone:


Drop him an email at:

[email protected]

Or Skype him at: