Launching Cook's Playbooks
LEARN IT! DO IT! COACH IT!
“Welcome to my weekly newsletter where I share three decades of start-up wisdom and personal “Best Of” lessons learned from scaling several iconic Silicon Valley companies including Intuit, Netflix, and Mozilla Firefox. My career has been profoundly influenced by some legendary coaches, mentors, and other executive team members and it is now time to pay it forward and to create a shared learning community for the next generation of startup leaders.”
Read It; See It; Do It; Teach It
Launching just a few days after Father’s Day, this new website and Cook’s PlayBooks newsletter is dedicated to my own father, Dr. Bill Cook (1939-2024) who passed away a few short months ago after 84 years of teaching me so much with his own words and actions.Read It; See It; Do It; Teach It is the playbook for all medical school students dating back hundreds of years. I know this because I was taught it by both my grandfather and my father. I am descended from 5 generations of medical doctors dating back to the Civil War - a tradition that ended when my brother and I chose to pursue careers in business. I distinctly remember both my grandfather and my father teaching me the “med school playbook”. I carried their lessons forward into my own business career in Silicon Valley.
Pictured below are my great, great grandfather’s civil war and my grandfather’s medical bag with original medical tools.
Requirements for an M.D.
1st year = Read It. Students memorize tons of medical books and spend their year being incessantly tested to make sure they have learned critical topics and techniques.
2nd year = See It. Students shadow doctors during their patient rounds in hospitals and surgerical procedures.
3rd and 4th years = Do It. Students begin performing patient checkups and are allowed to make initial surgery cuts and to close up incisions.
Teach It: 3-7 more years of “Residency”. During these years, students continue to Do It but more importantly they begin to Teach It - passing on their knowledge to younger, entry level students.
Finally, after 7-10 years (depending on specialty) of medical school, students finally earn a diploma and a license to practice as an M.D. (Doctor of Medicine); Medicinae Doctorum.
Pictured below are Diplomas of my grandfather (M.D. 1933) and my Great Great Grandfather (circa 1850). Both and several others have always hung prominently in my house growing up and are still proudly on display today.
Fast Forward to Silicon Valley: 1991 - 2024 (Today)
After my first 15 yrs of learning, doing, and advising others, I think I received my “MS” (Masters of Silicon Valley) around 2005. I’ve subsequently personalized the med school mantra to a simpler “Learn It, Do It, Coach It”.
I “Learned It” and continue to learn everyday in the startup operating rooms of Silicon Valley. Along the way, I was “coached” by some of the best at Intuit, ISN, Netflix, Wineshopper, and Mozilla including great VCs, and operating groups like the Alliance of CEOs and the Operators Guild.
I spent over 25 years “Doing It” as a full time CFO for the last 25 years and I began “Coaching It” on a regular basis with clients about 5 yrs ago. Today I am a full time Coach and Strategic Advisor to several 1:1 clients, teams, and companies.
Introducing Cook’s PlayBooks
“Jim, do you have a playbook for this?”
“Jim, do you have one of your ‘Best Ofs’ for onboarding a CEO?”
“Jim, do you have a great framework on who, how, and when to hire a CFO and/or scale my finance team?”
I’ve been asked several forms of such questions and dozens more over the past 25+ years. My close network and friends know me as an avid researcher, collector and curator of what I call “Best Ofs.” I’ve always been curious and passionate about financial and operational leadership since my very first Silicon Valley Senior Management role at Intuit as one of their first 100 employees where our only product was Quicken.
By curating, I literally mean saving articles, executive trainings, articles, spreadsheet templates, videos, and anything I considered “great” along my career journey. I like to learn things quickly and I definitely don’t like making the same mistake more than a few times. So, whenever I discover a new “Best Of” on a leadership topic, I store it. First on 3.5” discs, then Zip drives, then CD’s, DVD’s, and now my collection lives in the Cloud. I’ve now categorized, indexed, and created easily accessible links to my “Best Of” Library which I use daily in my coaching practice.
In sports, the best players in the world have a coach. I believe Business is a sport and all great leaders should have a coach. While, I had been coaching and advising on the side for several years, when Covid hit on March 13, 2020, not only did the whole world change but my coaching world changed. Shortly thereafter, my email and phone exploded seeking “Help!”
“Jim, will you be my mentor or coach?”
“Jim, other people told me to call/contact you, I’m looking for a CFO Coach.”
What began as CFO coaching has now expanded into a select group of high-profile CEOs, COOs, CFO’s and VP’s of Finance - a small community of clients that come together on Slack or various online and in person events. As I coach, I also continue to learn. The flywheel of “learning it”; “doing it; and “coaching it” is very powerful. I am now a full-time executive coach.
I also believe there is no such thing as a standard one-size-fits-all framework or playbook from me or anyone else relating to life, sports, or business. Any framework, playbook, or template must be customized for your own situation. When you customize anything, it forces you to not only learn it, but to also “do it”, and eventually to teach and coach others from your own point of view.
Over the last few years, I’ve been sharing several of my “Best Of” frameworks, playbooks and templates in various webinars, podcasts, and as featured speaker at VC or network events. The feedback has been positive and I’ve been asked to do more. Several sources of feedback said I should write a book. Maybe someday, but for now I’ll be starting to share back weekly with this newsletter.
I recently created the Venn Diagram (below) to capture my thoughts on what I believe makes a great coach based not only on my personal experience but also the experiences of others with coaches.
BOTTOM LINE: You have to “Want” to do this type of work. You must have credible “Operating Experience,” and you have to be great at “Communicating and Teaching.” All three components are necessary which is why great coaches are hard to find.
I'm excited to launch this new weekly newsletter and to continue to pay it forward by posting much more frequently on LinkedIn, Twitter/X, Instagram, and my new YouTube Channel - all branded as “Cook’s PlayBooks”. My next post is already que’d up and will diving deeper into my customized top level Coaching Framework used with all my clients.
My Mission is simple:
Pay It Forward: To share back my own personal “Best Of” lessons learned to the next generation of financial and operational leaders at venture-backed startups.
10x Leverage: To coach others in one year what it took me 10+ years to learn while scaling companies from Series A all the way through IPO.
Modern Day Coach (ode to Bill Campbell): I worked directly with Bill for several years and also hung out with Bill’s crew at the Old Pro on game day Saturdays for several years. Bill was known to connect deeply with people through his authenticity, directness, and his extremely humble wisdom. He coached Steve Jobs, Jeff Bezos, Larry Page and Sergey Brin, and so many others during the last stage of his career. We need more Coaches like Bill in this world.
Community: Create a knowledge sharing community “Best Ofs” where we can all Learn, Do, and Coach each other and continue to pay it forward to the next generation.
Building a Community: The Plan
Each week, this Substack Newsletter will bring you a “Best Of” headline and detailed content focused on key frameworks and playbooks from my Best Of Library. I’ll also be posting my point of view on current events and timely issues such as 2023’s Silicon Valley Bank crisis and the State of AI - a presentation I did with the Alliance of CEO’s almost a year ago.
I’m not designing this as a one-way download. My goal is to add my voice to help build a vibrant community of financial and operational leaders. This Substack platform is a “best of” place to crowd-source best practices, to exchange ideas, and to create an environment of learning from each other.
As @Casey Woo (co-founder of the Operators Guild) legendarily just memorialized in the annual Operators Guild Summit (May 2024), we are the “Special Ops” and we are here to UnF**k Sh*t!.
So BOOKMARK this blog, SUBSCRIBE to get posts straight to your inbox and Comment to share your own experiences.
Let’s create this “Best Of Community” together.
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Disclaimer: I am not your accountant, tax advisor, lawyer, CFO, or any other role for you, my reader. My role for this content is simply someone who is personally sharing what I’ve learned in the hopes you can take it and make it better. Everything I publish represents my opinions only, not advice. Being an executive of your company requires you to gather resources like this but for you to make any final actions and decisions with input from your own officers, directors, and legal advisors.
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A quick shout out and thank you to so many others who are on a similar mission of sharing back and communicating their own “Best Ofs”. I’ve been inspired and continue to learn from so many others including these great influencers.
Marc Randolph - and of course That Will Never Work
Reid Hoffman and his - Master of Scale
Founders Circle Capital and their CFO Circle
and many, many other sources
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