Coach and Advisor to Enterprise Owners/CEOs


All companies go through lifecycle stages from startup to growth to maturity to decline to death.

I help owners/CEOs get their companies to the high point of value and put them on the path or realizing that value at the time of an exit.

Company building involves many things but at the top of the list is knowing what key issues need addressing and having a process to get answers.

All successful people have relationships with someone to help them explore answers to important questions or to be a sounding board; someone to talk to. That is where I come in. I am the coach and M&A advisor that specializes in helping CEOs and company owners build the value of their companies on that long and tricky road to a maximally valued exit. I am also an angel investor in some select early stage companies and startups.

I am good at what I do because I have been through the company building and exit process dozens of times. For three decades I was a venture capitalist that financed dozens of companies the majority of which had successful exits. I've been a CEO nine times and have managed six companies through periods of disruption to successful exits. I have proven my ability to transfer what I learned over 5 decades to others as a coach and I am a published author on the topic of company financing and exit planning

You are unlikely to find someone more qualified than I am to help you build the company you dream yours can be. If you are the head of a US based startup to medium sized company with a B-to-B business model we would love to get to know you with the goal of seeing if and how we can help you grow your company.

A free Zoom session to see if and how I can be of help and if I am the right person to provide that help. I guarantee that this call will produce at least one idea for growing your company.

Coaching has high ROI

According to the American Management Association, organizations that use coaching reported stronger market performance. A global survey of coaching clients by PriceWaterhouseCoopers and the Association Resource Center concluded that the mean ROI for companies investing in coaching was seven times that of the initial investment. A quarter of the companies in the survey reported an ROI of 10 to 49 times investment.

I can cite elements of my track record that increase cited ROI by orders of magnitude.

“Exits are great but it’s better to do it as a choice, not a consequence of bad moda operandi.”

― Richie Norton

We have seen too many founders wait until it was time for an exit before thinking about how to maximize value at the exit. That cost them a lot. I do not mean getting 20% less for the company, I mean getting 200% more if they had prepared in advance. 

My Experience-Based Approach

“The only source of knowledge is experience.”
– Albert Einstein

I will say it again.

I am good at what I do because I have been through the company building and exit process dozens of times. For three decades I was a venture capitalist that financed dozens of companies the majority of which had successful exits. I've been a CEO nine times and have managed six companies through periods of disruption to successful exits. I have proven my ability to transfer what I learned over 5 decades to others as a coach. And, yes, I have started four companies, the latest of which was formed mid 2022.


Daniel Patrick Forrester

Founder, Chief Executive at Avizhen LLC

John Grillos is the "exit whisperer." From reading his wonderful book, to seeking his wise counsel, he has helped me and my partner to think into all the dimensions of our future and the partners we want in it. He is patient and thought provoking. He helps you take the long view. His feedback on the future and what is possible -- will make you and your company better today.

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Greg Wientjes

CEO and Founder at SUpost, Stanford University

The words that come immediately to my mind when I think of John Grillos are inspiring, generous with his extraordinary wisdom, and caring.

John Grillos is lion-hearted -- a fierce advocate for what he believes is right and good for the world and the people he cares about. I first met John while I was a participant, and he was a teacher at, Draper University in 2013. Since then, he has been my mentor, friend and a lighthouse in the sometimes dark and uncertain world of entrepreneurship.

John has served in the US Marine Corps; and he has managed four venture capital firms (founding two of them) with combined capital under management exceeding $500 million. His clear thinking is striking -- able to receive information and distill the essential components to focus in on. He is caring and kind, and truly the type of person you would want as a friend, mentor and coach. Extremely talented and accomplished in business, he has been a director of 26 for-profit (private and public) and nonprofit organizations.

I am deeply grateful for how receptive and caring he is in nurturing entrepreneurs.


Victor Cocchia

CEO at Vysk Communications

This may be one of the easiest recommendations I have ever made. Since the first day I encountered John he has been an incredible mentor, source of inspiration and educator for me. He has generously shared with me his experiences hinted over decades in the VC and technology world. He never misses an opportunity to help me, whether it be through lessons he has learned or through advice he has openly offered.

Time after time he’s been proven to be correct with the recommendations he has made to me, even when they have gone against what I wanted to do. I’ve learned to trust his judgement, his business acumen, his experience and his instinct, which time and time again proves to be entirely accurate and on point.

I would highly recommend John, as he’s been an invaluable resource for me.


Barbara "Bobbi" Kurshan

Board Member at American Public Education, Inc. (APEI)

I have worked with John as a mentor, partner and consultant. He brings deep knowledge of the investment space, technology in learning and global education.

He is an excellent leader and mentor and explores innovative approaches and ideas easily and with an understanding of how Innovation impacts change and success. John provides a reality check with empathy to early stage entrepreneurs. He is able to provide advice to CEO's not just as an investor but one who has been in the CEO seat. Working with John is always interesting, fun and a valuable experience.


Howard Block, PhD

CFO at Congregation Rodef Sholom

John and I worked together on private education investments at Robertson Stephens and Company. In 2009 we bought NTT Inc, a leading provider of skilled trades instructor led training. We were a good team. John was strong in the skills needed by a CEO in planning and performance, which built upon my skills in sector analysis and strategy development. Our partnership resulted in a very successful sale of NTT in 2012.


Nino Marakovic

CEO & Partner at Sapphire Ventures

John is simply outstanding - someone you want on your side of the table when negotiating or making tough decisions. I have had the fortune to be mentored by John for many years and can't recommend him more highly!


Heather Gallien

Principal | Chief Marketing Strategist at creo marketing

John is a true leader who has a clear vision for every venture, along with the tenacity required to build a team and make it happen. His expertise in business start-up, turnaround management and growth strategy is as wide as his focus is deep. When on a mission, he is unwavering, and he inspires others to bring their A-game. Although he’s set on what he wants to achieve, he empowers people to lead in their domains. Additionally, his experience is priceless for any emerging company exploring how advanced technologies can improve education and training.


Dror Ben-Naim

Founder & CEO at Smart Sparrow (acq. Pearson)

When I need to lift my game, I always get helpful, supportive, and learned advice from John that is immediately actionable and that makes me a grow as a leader.


John Gumas

CEO at Gumas Advertising

I’ve worked with John for years. He’s one of the most astute and knowledgeable professionals I know. He really knows how to get the job done.


Kristine Hanna

Director, Web Archiving Programs and Services at Internet Archive

John has that illusive mix you want in an investor - he is very supportive, but he also challenges you to do better, be better, and to keep trying. John was genuinely there for us, in the good times and the bad and he truly understands what it takes to start, build and grow a company.

Peter D

Peter D.

Professional CEO, Professor, Author | San Francisco

The best exits start years in advance.

This book is for business owners with no prior exit experience. There is nothing like learning on the job but the risk and cost are high. Why would you do that? Instead, study John's book which speaks from exit experience across time, industries, business models, capital structures, and stages of venture maturity. He presents a road map and inventory of what you need to know to orchestrate an exit that achieves maximum value. Two key points are that a well run exit starts years ahead of time and there is no substitute for having someone on your team who has "been there and done that" to lean on and guide you. Good luck with yours!

Amazon Customer

5.0 out of 5 stars: Solid advice for raising the value of your business.

If you own your own business, read this book now. It will help you make decisions and focus on outcomes that will someday take you to a profitable exit. The author is not an academic; he is a practitioner who has done everything he talks about. When you buy this book, start with his chapter on War Stories to get an idea of the great breadth of the author’s experience and expertise. It’s a fast, engaging read.

Amazon Customer

5.0 out of 5 stars: Great outline for companies looking to achieve maximum value.

I enjoyed reading your book and learning of your experiences with so many different types of companies. The shift we are seeing (Due to covid) of shortened lifecycles of companies across the board makes your book a timely release to the marketplace. I found it very interesting how you broke down the importance of various financial measurements for a company’s financial health based on the desired outcome; whether that was going public, merging or selling. I would imagine several companies will find your process for building a path to the exit an excellent source to driving value.

Amazon Customer

5.0 out of 5 stars: Thoughtful book, lays out some interesting concepts

I've been working with some early stage companies lately, and I bought this to get into the headspace of early stage founders. I appreciated that the author clearly had lived through these experiences, and his advice was interesting and thoughtful. There's clearly an art to the timing....

Amazon Customer

5.0 out of 5 stars: practical advice if you may want to sell your business someday

Grillos has written a readable and very practical book for any business owner who thinks he might want to sell it someday. I say someday because you want to read this book long before you are actually ready to sell.
Yes, Grillos does cover the steps in a sale process, such as selecting advisors and bankers. But i think the most valuable chapter is Chapter 4, in which he gives a very tangible method for assessing where you business is now and what you need to do to make it ready for a sale when the time comes.

Bernie Cowsert III

5.0 out of 5 stars on Amazon

Great ideas for anyone selling, merging or starting an IPO for your business.

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