Executive Coaching Built on Extreme Preparation™

As an executive coach, Randall Kaplan works one-on-one with founders, executives, business owners, and ambitious professionals using his Extreme Preparation™ methodology - the same approach he used to help take Akamai Technologies public and to make more than 100 investments through JUMP Investors. The premise is simple: the people who win the moments that matter are the ones who prepare more deeply than everyone else. Extreme Preparation is a system for doing exactly that - sharpening your strategy, your communication, your decision-making, and your execution when the stakes are highest.

For the past 25 years, I've advised more than 60 companies and coached entrepreneurs, founders, CEOs, executives, business owners, investors, and ambitious professionals.

Things I advise on:
✔️Pursuing the idea that’s been in your head for years
✔️ Starting a company
✔️ Getting your first customers
✔️Growing your business
✔️Creating meaningful relationships
✔️Meeting anybody at any level in any industry
✔️Getting any job even if companies aren’t hiring
✔️Creating the best pitch deck
✔️Raising money
✔️Fixing your startup bottlenecks
✔️Being the most prepared person in the room
✔️Learning the intangibles (which are often more important than the tangibles)
✔️ Recruiting experienced employees, advisors, and board members
✔️Quitting your job
✔️Taking calculated risks
✔️Chasing and pursuing your dreams
✔️Investing
✔️& more

I have a crazy story about overcoming significant obstacles, overcoming failure, staying the course, and pursuing my dreams until I achieved them.

I moved to Los Angeles when I was 24 after graduating from law school with $3,000 in the bank and knowing almost nobody. I lost my first job five and a half weeks later, took another job that required a minimum three-hour commute six days a week, was told I had to leave six months later, and ultimately found my third job in eight months.

At the time, I was miserable. I hated practicing law, desperately wanted a change, and finally decided it was time to pursue my lifelong dream of starting my own company and achieving financial independence.

I wrote 300 cold letters to CEOs, landed 80 meetings, became Assistant to the Chairman of a Fortune 500 company, and then co-founded Akamai Technologies with three people at MIT. Today, Akamai has 11,000+ employees, $4.2 billion in 2025 revenue, and an approximately $16 billion market cap.

My philosophy has always been simple: Anything Is Possible.

Randall coaches a limited number of clients at a time. If you want a partner to help you prepare relentlessly and perform when it counts, reach out through randallkaplan.com or send the word COACHING to @randallkaplan on Instagram to start a conversation about working together.