Inspire. Empower. Achieve.
Extreme Preparation
Work with Randall Kaplan
Serial Entrepreneur and Co-Founder of Akamai Technologies
with Investments in Google, Seagate and Lyft
and over Eight Billion-Dollar Exits.

RANDALL KAPLAN

Extreme Preparation
Business Consulting
1-on-1 Coaching
Podcasting and Media
Startup Advising
Extreme Preparation
Venture Capital
Corporate Speaking
Podcasting and Media
Startup Advising

Strategic Executive Coaching with Impact

One-On-One Executive Coaching

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AS MENTIONED IN

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Unlock and Transform Your Potential Into Reality.

Elite one-on-one coaching from a serial entrepreneur, co-founder of Akamai Technologies, and venture capitalist
who turned 300 cold letters into 80 CEO meetings - and used Extreme Preparation™ to transform the trajectory of his career.

I moved to Los Angeles when I was 24 with $3,000 in the bank, was fired five and a half weeks after starting my career, and went through three jobs in eight months doing something I despised. I desperately wanted a change, so I created a plan to pursue my dreams: I wrote 300 cold letters to CEOs of major companies. Everyone told me I was crazy and that nobody would meet with me. I didn't listen. Those letters generated 80 meetings and ultimately led me to become Assistant to the Chairman of a Fortune 500 company, changing the trajectory of my life forever.

Three years later, I co-founded Akamai Technologies with three people at MIT. Akamai became one of the fastest-growing technology companies of its era and today has more than 11,000 employees, generates approximately $4.2 billion in annual revenue, and has a market capitalization of approximately $16 billion.

I founded JUMP Investors in 1999, and since then we have invested in more than 100 early-to-late-stage companies, including Google, Seagate, and Lyft. I've spent a lifetime betting on potential - and now I'm in the business of maximizing it. I exclusively coach driven founders, executives, business owners, investors, and ambitious professionals who are ready to transform their potential into meaningful results.

~$16B
Akamai Market Capitalization
100+
Early-to-Late-Stage Investments
25+
Years Advising & Coaching
60+
Advisor Positions

What I Can Help You Achieve

25 years of experience distilled into actionable coaching for
entrepreneurs, executives, and high-performers.

Pursuing Your Big Idea

Turn the idea that's been in your head for years into reality with a proven framework.

Starting & Scaling

Launch your company and navigate the critical early stages that determine success.

Getting First Customers

Master the art of acquiring customers even when you have no track record.

Raising Capital

Create compelling pitch decks and learn what VCs actually look for.

Extreme Preparation

Become the most prepared person in every room - my trademark methodology.

Career Transformation

Get any job even when companies aren't hiring. Navigate major career pivots.

Business Growth

Fix bottlenecks, recruit A-players, and build systems that scale.

The Intangibles

Master the soft skills that often matter more than technical expertise.

A Different Kind of Coaching

Built on Extreme Preparation

For the past 25 years, I've coached hundreds of entrepreneurs, business owners, CEOs, executives, professionals, venture capitalists, investors, and athletes in the NBA, NFL, and NHL - equipping them to achieve victories they didn't think were within reach. What separates my coaching from everyone else is a methodology I invented, refined, and trademarked: Extreme Preparation.

Extreme Preparation™ is not simply a philosophy. It is a precise, repeatable system designed to increase the odds of success, accelerate breakthrough results, and help people perform at their best when the stakes are highest. I use it across entrepreneurship, career transitions, fundraising, leadership, communication, major decisions, and other critical moments where deeper preparation creates a meaningful advantage. My clients don't simply prepare for what is likely to happen. They prepare for the outcome they actually want. From first-time founders to seasoned executives, the goal is the same: prepare more deeply, execute more effectively, and create outcomes others may have thought were impossible.

What World-Class Leaders Say

The Most Prepared Interviewer They've Ever Had
David Solomon
CEO
Goldman Sachs
Tony Robbins
Motivational Speaker
Entrepreneur
Mark Cuban
Entrepreneur
Dallas Mavericks
Jimmy Pitaro
Chairperson
ESPN
David Solomon
CEO
Goldman Sachs

Case Study - Extreme Preparation in Action

How My Coaching Helped a Client Go From $0 to $50 Million in 4 Years

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From $0 to $10M in one year and fast approaching $50M by year four

A high-income professional with zero net worth didn’t want “a little more.” He wanted to build real wealth - multiple businesses, a clear strategy, and a path to eight- and nine-figure outcomes.

$10M
Net worth (Year 1)
$50M
Net worth (Year 4)
5
Operating businesses
Decision-making
Core lever
Highlights
  • Avoided a high-risk partnership using a simple litmus test.
  • Built a detailed plan for financing, lease terms, location, and cash flow.
  • Prioritized opportunities by upside, execution complexity, and passion.
  • Grew from one practice to a diversified portfolio across multiple sectors.

Net worth trajectory

📈 Milestones
$50M $0 Start Year 1 Year 4
Start $0
Year 1 $10M
Year 4 $50M
The Portfolio Today
A simple visual stack to answer the skeptic’s question: “How did this happen?”
🦷
Pediatric Dental Practices
🏥
Surgical center
💻
SaaS Technology
⚖️
Legal Services Software
🤝
Consulting & Recruitment
TEDx Talk

How to Get Your Dream Job Through

Extreme Preparation