Inspire. Empower. Achieve.
Extreme Preparation TM
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
Inspire.  Empower.  Achieve.

Unlock and Transform Your Potential Into Reality.

Elite 1-on-1 coaching from a serial entrepreneur, Akamai co-founder, and venture capitalist who turned 300 cold letters into a $14 billion company.

I moved to Los Angeles when I was 24 with $3,000 in the bank, was fired 5½ weeks after starting my career, and had three jobs in eight months doing something I despised. I wanted a change and create a plan to achieve my dreams – writing 300 cold letters to CEOs of major companies. Everyone told me I was completely crazy and that nobody would meet with me. I didn't listen, wrote incredible letters, and earned 80 meetings – and that persistence led me to become the Assistant to the Chairman at a Fortune 500 company which changed the trajectory of my life forever.

Three years later, I co-founded Akamai Technologies with three people at MIT. It grew to a $1 billion company less than a year and today has 10,000 employees, earns $4 billion per year, and has a $14 billion valuation.

I started my investment firm 26 years ago, and since then have made more than 100 investments, 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, and professionals from all industries who are ready to aggressively transform their potential into reality.

$14B
Company Valuation
$14B
Investments
$14B
Years Coaching
$14B
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 PreparationTM

For the past 20 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 PreparationTM.

Extreme Preparation® is not a philosophy. It's a unique, precise, replicable system that dramatically increases win rates, accelerates paths to breakthrough results, and turns what others think is impossible into reality. It works in every high-stakes arena—creating and building businesses, planning for the future, driving decisive career transformations, and making critical life decisions with clarity, confidence, and conviction.This is why clients don’t just achieve their goals—they dominate the moments that matter most, execute with precision under pressure, and sustain outsized results over time. From first-time founders to seasoned executives, Extreme Preparation® has been the secret weapon behind outcomes that redefined what was possible.

What World-Class Leaders Say

The Most Prepared Interviewer They've Ever Had
David Solomon
CEO
Goldman Sachs
Tony Robbins
Motivational Speaker
Entrepreneur
Marc 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

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

How We Work Together

I work primarily with founders, executives, business owners, ambitious professionals, and athletes to clarify priorities, raise performance, and create a concrete plan to execute on meaningful long-term personal and business objectives.

1
Submit Your Application
Share your goals and current challenges.
2
Review & Discovery Call
If there's a fit, we'll schedule a call.
3
Begin Coaching
Start your personalized transformation journey.
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In Search of Excellence Podcast

In Search of Excellence, I sit down with some of the world's most accomplished individuals for candid and inspiring conversations about what it really takes to succeed. Join me as I uncover motivating stories of grit and resilience—revealing how billionaires, icons, and industry leaders overcame significant obstacles on their paths to extraordinary success.