CEO Support Service

Your "Wingman" - Exclusively for CEOs
Make An AppointmentAbout Me

The CEO Support Service:

The “CEO support service” is by and for CEOs only. It’s not for the Board or Shareholders (although they may benefit). It’s a confidential support service to help support you – the CEO (and no one else).

The service is aimed at a handful of CEOs who want to go to the next level, who understand that having a support person to talk to, brainstorm with, and who is “their person” is essential. A person who they can have the hard discussions with, who is only on their “side” and is their go-to sounding board. Someone who you can say the “scary things too” without judgment or fear of reprisal and someone who has your best interest at heart.

I am that person. I have been through the fire, fallen down the holes, and got back up to fight another day – I can help guide you in the dark times and keep your feet on the ground in the great times. I am your consigliere.

About You

In our regular sessions, we will focus on you and your challenges and opportunities. Together we will work to avoid failure modes, to optimize your personal impact on the business, and do that while helping you lead a balanced and healthy life. My job is to listen, to guide as needed and to be a support person to assist you on your journey – reducing your stress, helping with focus and providing a confidential “sounding board”.

Every CEO can get lonely and will face tough choices – you don’t have to make these in isolation, I can help. I know how you feel, I know about the highs and lows, I have made the hard choices and I have had the dark thoughts. I have seen it all and you can use that experience to avoid problems and to do better!











The above are areas we can work on helping you develop personally and in your business. Together we will discuss every aspect of your work and career, to maximize your impact while ensuring you are happy, healthy and hopefully wealthy!

Topics for discussion












The above topics are examples of areas where I have 35 years of experience in various startups, in my teaching practice and with coaching in the world’s top business schools.

Hiring great people and keeping them for years, raising millions of dollars, weathering the competition, building great products, managing investors, and firing the bad actors. Sales, marketing, operations, product and project management, engineering, new product development, pitching, finance, IP , M&A and legal. If you need it in a startup, I have done it, and yes I have started in my garage!

You name it, I have done it and I am here for you and your questions. We can do this together, better.

About Jon Gillespie-Brown

CEO Coach

Jon works with a maximum of ten CEOs at a time to help them develop, grow and be successful.

Author, Angel, CEO and Professor at CU-Boulder: Leeds School of Business. 35 years in Tech. 20 years as Prof, Mentor, and Startup Coach (CU Boulder, Stanford, UC Berkeley & London Business School).

 Jon is not one of those advisors who are out of date, he still works every day in his own Companies as well as helping others – He also teaches the cutting edge techniques used by the best startups in the world – at the best Entrepreneurship programs and accelerators on the Planet.

Jon has extensive leadership experience in the information technology, communications, and social web with 30+ years in the IT business. Working across many sectors (B2C, B2B & Enterprise for Software, Services, and Hardware) he has a deep understanding of every Ecosystem, having built both Consumer, Enterprise, and SaaS Software businesses.

For the last 20 years, he has been a Start-up founder and CEO.  Jon works in and with Startups as an adviser and investor.


Personal details about Jon

Jon is not just all “business” he believes in developing both the right and left parts of his brain. He has lived all over the World, has learned 5 languages, and written 5 books. He went to military school and studied on several continents.  He has several patents, loves cars, and is also a beekeeper. He has collected over 1000 books and loves to fly fish. Jon has studied at the Le Cordon Cookery School in London as well as at over a dozen other cooking schools, loves wine and entertaining. He has made some money, and lost more!

He has lived in London, and the Bay Area for over 20 years before moving to Boulder, Colorado. Jon has been married for over 20 years and has two grown sons.

So what’s the point? If you want someone to help you as a CEO, pick someone who has a broad set of experiences and skills, someone who can handle the good times and bad. Someone who is “bulletproof” and can help you when the going get’s tough. Someone who is well-rounded and has enough experience to help but who is not so old they don’t relate to you.

People & Institutions I’ve Worked With for 20 Years

“…there’s no better or more insightful mentor/teacher than Jon. He’s been a superb sounding board over the years for London Business School start-ups
John Mullins, Associate Professor of Management Practice, London Business School

…he is one of the sharpest thinkers and more importantly execution driven leaders I know”
Yossi Feinberg, The Adams Distinguished Professor of Management and Economics, Stanford Business School

“…I would highly recommend Jon …as a great mentor for entrepreneurs, and as a solid business reference source for insights in the world of innovation and entrepreneurship
Dr. Ron Lesniak, Teaching Fellow UC Berkeley

Jon mentored our team as part of the “Evaluating Entrepreneurial Opportunities” class at Stanford’s Graduate School of Business. His guidance and advice were invaluable as we went through the process of validating our ideas. Jon’s ability to step back from problems and point out key learnings was particularly helpful. This was most evident when we were faced with the decision to pivot from one idea to another.

I learned a lot from Jon and really appreciated his honest feedback and enthusiasm for entrepreneurship.

Tim Holley

VP of Product, Etsy

Jon’s enthusiasm for entrepreneurship is infectious. Our team of undergrads not only benefited from his energy, but also from his practical, structured approach to all phases of the entrepreneurial process (whether it be the ideation stage or construction of a pitch to VCs) as well as his candid feedback. We learned to look for an Advil not a vitamin, to commit to the research process, and to place high value on customer development and iteration. Of course, these are just a few of the many nuggets of wisdom offered up by Jon during the mentorship process. He was a great sensei – it was a pleasure to learn from (and work with) him

Greg Justice

VP, Content, Calm

Jon’s hard-learned lessons as an entrepreneur and his ability to provide honest and sincere feedback have been extremely valuable assets to my Entrepreneurship team at Haas and my learning experience as an Entrepreneur in training.

Jon has enabled our team to approach entrepreneurship as it should: a tough battle in which only the smart and well-prepared succeed and enthusiasm for entrepreneurship.

Abhi Sawant

SVP Engineering, Okta

Jon’s success as a serial entrepreneur has been an inspiration to many of us who have had the chance to know and work with him. His work with business students at Stanford University and The London Business School has been an inspiration to several young entrepreneurs on both sides of the Atlantic. Over the past decade, Jon has provided me with very insightful help in both my personal and professional life – and in particular – with insights into starting and managing high-growth, entrepreneurial software companies. His ideas and objective advice are of value to anyone working in similar environments.

Mike Cottle

VP, Partnerships, Telenav

FAQs about my services?

What is the CEO Support Service?

The CEO Support service is a 1:1 session with me, your support person. The idea is simple; I have been doing startups for 35+ years – if there’s a mistake to be made I likely made it. If there’s been a tough situation to be endured, I have been through it. With teaching and mentoring, as well as being a CEO for 20 years, I feel I can offer expert advice and support to anyone on a similar journey.

How Do I Know if The Service Is Right for Me?

Great question, an initial discussion is the best way to check me out and to see if I can help you. I am direct and simple in my dealings. If I feel there’s a fit, I will let you know. You will also be able to get a feel for my style and if you believe I can help support you and be your “wing-person” on your own unique journey.

Do You Only Work With Established Companies?

No, I work with Startup CEOs of all types that can afford my fees and where I feel I can add real tangible value. In general, that will be with fully funded Startups where paying someone to help the CEO makes the most sense both financially and due to the huge pressures placed on high-growth businesses.

Do You Offer Other Consulting Services?

I will help my CEOs with other services, but this is very limited. If there is a challenge that needs more than my skills and I feel I can help, I will build a team to help – or on some occasions, there are non-CEO services needed where I can help, I will consider those as they present themselves.

Do You Invest In Startup Companies?

Yes, I often invest in Startups, especially those that I know well. I will also help my CEOs with fundraising and any related challenges.

How do you charge?

I have a very simple charging structure. I only work with a maximum of ten CEOs at a time and they all pay the same rate for my support.

I charge a retainer fee of $2500 per month for two one-hour meetings – with extra time on an “as needed” basis. This isn’t an hourly gig. If you need me and I can help, I am “on-call” to assist you in your hour of need, but the usual cadence will be a bi-weekly meeting to discuss your challenges and needs.

The service is highly limited and, based on trust, there are no long-term lock-ins for either side. If it’s helping we carry on, if it’s not, we part as friends.

What don't you do?

My role is to support and service you the CEO. I don’t do your work or the work of others. I listen, discuss and give feedback. I don’t write reports, or edit documents, or build out spreadsheets – that’s not a good use of our time together. I am happy to guide and support – not do operational work.

CEO mental health

While I am not a trained psychologist, I am a very seasoned CEO of Startups. I have to be honest and say there have been many very challenging times in my career where I have had genuine issues with stress, disillusionment, and anxiety. I have had to work through these tough times and have tools and techniques to help you with these issues. Most CEOs have to tend to their mental as well as physical health to be on top of their game.

What is the ROI on the CEO support service?

Every CEO should know the ROI, right? In the case of this service, I suggest that the small financial and time commitment to being at your best as CEO is an “instant” ROI! In almost any startup that succeeds the outcome is in millions of dollars of value (often 100-millions) but getting to the endgame is a very tough road – what’s it worth to you and your team for you to make it? Not only do you need to win, but to do so while preserving your health and wellness. Having a trusted “wing-person” can be the difference between success and failure..

How do I get started?

First, let’s get to know each other. Please hit the appointment button at the top of the page or go here: Once we have had a brief introduction, we can decide if we want to meet up for a more detailed discussion and a plan for a relationship. If that all works out, and Jon has enough bandwidth, a plan can be formulated for regular meetings and to handle any immediate needs or concerns, etc. Having good chemistry is the first step to a mutually beneficial relationship.