An Entrepreneur’s Hustle, Humor, and Poorly Timed Brilliance
By: Stephen H. Watkins
Language: en
Categories: Business, Entrepreneurship
A Memoir of Hustle, Humor, and Poorly Timed Brilliance Stephen Watkins did not follow a roadmap. He made one. From mowing lawns to stumbling through cabling contracts, Lotus Notes, and union battles, he managed to disrupt Wall Street with a novel security structure and invent TIGRcubs® along the way. Funny, candid, and full of grit, this memoir rewrites the American Dream. Success is not about avoiding mistakes; it is about surviving them. With Midwest charm and Wall Street savvy, Watkins shows that perseverance and caffeine can make half-baked ideas work. Perfect for anyone who has bootstrapped through chaos and lived t...
Episodes
2025-12-12 Watkins @ NTRX Minute
Dec 15, 20252025-12-05_NTRX_Minute
Dec 08, 20252025-12-05_NTRX_Minute
Duration: 00:01:362025-11-21_Watkins @ Entrex Podcast
Nov 26, 20252025-11-21_Watkins @ Entrex Podcast
Duration: 00:01:302025-11-14_Watkins_At_Entrex_Podcast
Nov 14, 20252025-11-14_Watkins_At_Entrex_Podcast
Duration: 00:01:332025-11-07_Watkins_At_Entrex_Minute
Nov 10, 20252025-11-07_Watkins_At_Entrex_Minute
Duration: 00:01:232024-10-31 Watkins at Entrex Podcast
Oct 31, 2025This weeks update
Duration: 00:01:24NTRX - 2025-10-27 Podcast
Oct 27, 2025NTRX - 2025-10-01 Podcast
Oct 02, 2025This is the official NTRX Podcast for 2025-10-01
Duration: 00:04:01Chapter 12 – From Boats to Bonds
Sep 13, 2025TIGRcubs gained traction. We merged into a public shell right as COVID hit. Plans delayed, capital frozen—but the appetite for yield securities was clear.
Duration: 00:02:26Chapter 11 – So Naturally… I Met a Guy
Sep 13, 2025Chapter 11 – So Naturally… I Met a Guy
Birth of TIGRcubs®. From Frankenstein spreadsheets to streamlined revenue-sharing securities. Partnerships, lawsuits, and even a blockchain debut with Overstock. “Meet a guy” became my business model.
Duration: 00:13:25Chapter 10 – Regulators & Financiers
Sep 13, 2025Pitching regulators, charming NASDAQ, and hitting walls of bureaucracy. Then came Arthur Lipper and the spark of revenue-based finance. Add in a White House invite—surreal doesn’t cover it.
Duration: 00:08:39Chapter 9 – Between Ventures
Sep 13, 2025Chapter 9 – Between Ventures
Post-crash purgatory. MIT taught me one line that changed everything: “Own the operating environment.” Led to Entrex—the entrepreneurial exchange for 28 million forgotten private companies.
Duration: 00:06:49Chapter 8 – The Internet, Starts & Stumbles Dot-com boom.
Sep 13, 2025Dot-com boom. Built 3Clix: city-based online delivery years before DoorDash. Investors loved it—until greed, betrayal, and the crash wiped it all out. Cue: lessons in trust and timing.
Duration: 00:07:30Chapter 7 – Babies, Boats & Windows
Sep 13, 2025Chapter 7 – Babies, Boats & Windows
Living on a trawler with a toddler, we partnered with Mike Rothman to scale SMS/Assist. From thermal faxes to a $950M exit, exception management became a business model.
Duration: 00:07:10Chapter 6 – Networking, Cables & Unions
Sep 13, 2025Chapter 6 – Networking, Cables & Unions
Built a cabling company with Shelly, fought unions, and scaled chaos with Lotus Notes. Martini boat tours and 25,000 projects later, I learned: if it’s not in Notes, it doesn’t exist.
Duration: 00:12:54Chapter 5 – Steffey, Sales & Beige
Sep 13, 2025Crash course in sales at Steffey Marketing. Learned that everything has to be sold—and that beige offices can hide life-changing encounters (including meeting Shelly).
Duration: 00:07:35Chapter 4 – The Teak Desk
Sep 12, 2025Fresh out of college, I blew a seed round on speakers and a giant teak desk. Lesson learned: desks don’t make revenue, pivots do.
Duration: 00:06:13Chapter 3 – The College Detour
Sep 09, 2025College internship at Anixter. Enter Frank Mitchell, logistics wizard. Corporate bureaucracy tried to kill his chaos, but a clunky IBM PC and exception management saved the day.
Duration: 00:07:13Chapter 2 – Golden Child’s Shadow
Sep 09, 2025The evolution of Harkins Enterprises: teenage TaskRabbit before apps existed. Fence-staining disasters, billing “adjustments,” and the painful art of apologizing creatively.
Duration: 00:13:25Chapter 1 – Teenage Hustle
Sep 09, 2025High-school trauma, garage-door mishaps, and a teenage lawn-care empire. Outsourcing badly taught me more about business than Algebra ever did.
Duration: 00:05:21