Coaching, Leadership, And What I Learned in Prince George's (PG) County Maryland About Winning

His mom arrived in America with $4. His dad came with $10 and two shirts. Together they built a life — and passed down a philosophy that would eventually help their son lead a $1.3 billion exit.

Sujey Edward grew up first-gen in PG County, Maryland watching his father run gas stations, tobacco farms, video stores, and a Peruvian chicken restaurant — all with one belief: "The math is the math." (The kanakku is the kanakku)

Sujey took that mindset into tech, pivoted from chemistry to IT by spotting a supply-demand gap, bluffed his way into his first job, and grinded two days ahead of everyone just to keep up. He eventually became CTO of Octo, wrote a personal check to buy in, and helped grow the company from 200 to 1,500 employees before IBM acquired it for $1.3 billion cash.

In this conversation we get into:

— Growing up first-gen in PG County and what that environment builds in you
— His dad's serial entrepreneur philosophy that worked across every industry
— Pivoting from chemistry to IT by reading supply and demand
— Faking it as a test automation engineer and grinding to catch up
— Why basketball coaching made him a better executive
— His unconventional 30-minute interview method
— Betting his family savings on Octo — and winning
— Growing a company from 200 to 1,500 employees and a $1.3B exit
— Why he walked away from IBM — sprints vs. marathons
— The funeral at 16 that redefined his entire metric for success
— Why real regret comes from inaction, not failure
— A three-question stress test that reframes any problem instantly
— What AI is really going to do to the workforce in the next 10 years

Chapters:

00:00 Introduction02:08 First Generation Family from India07:15 "I Came With $10 and Two Shirts"07:36 The Tobacco Farm & "The Math Is the Math"15:07 Family Travel & Lessons from the World19:45 Why He Chose Corporate Over Entrepreneurship26:08 How Coaching Made Him a Better Business Leader29:17 His Unconventional 30-Minute Interview Method33:17 From Chemistry Major to IT Career35:58 Faking It as a Test Automation Engineer40:32 The Three-Question Stress Test46:46 Why We Regret Inaction More Than Failure50:25 Leaving Salient CRGT for Octo as CTO55:00 The $1.3 Billion IBM Acquisition57:50 Learning to Let Go and Trust Your Team1:40:05 The Funeral That Changed Everything at 161:48:14 Sprints vs. Marathons — Why He Left IBM1:52:29 Joining IDS as Chief Strategy Officer1:56:30 Why You Need Multiple Mentors1:03:09 His Relationship With Money Then vs. Now1:23:17 Where AI Takes Us in the Next 10 Years1:28:49 "The Internet Is Still the Internet"1:29:20 Final Thoughts