Stephen H. Watkins
An Entrepreneur’s Hustle, Humor, and Poorly Timed Brilliance
A Memoir of Hustle, Humor, and Poorly Timed BrillianceStephen 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 bootstrappe...
Author
Stephen H. Watkins
Category
Podcast website
Latest episode
Feb 2, 2026
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Episodes
2025-12-05_NTRX_Minute 08.12.2025 1:36
2025-12-05_NTRX_Minute
2025-11-21_Watkins @ Entrex Podcast 26.11.2025 1:30
2025-11-21_Watkins @ Entrex Podcast
2025-11-14_Watkins_At_Entrex_Podcast 14.11.2025 1:33
2025-11-14_Watkins_At_Entrex_Podcast
2025-11-07_Watkins_At_Entrex_Minute 10.11.2025 1:23
2025-11-07_Watkins_At_Entrex_Minute
2024-10-31 Watkins at Entrex Podcast 31.10.2025 1:24
This weeks update
NTRX - 2025-10-01 Podcast 02.10.2025 4:01
This is the official NTRX Podcast for 2025-10-01
Chapter 12 – From Boats to Bonds 13.09.2025 2:26
TIGRcubs gained traction. We merged into a public shell right as COVID hit. Plans delayed, capital frozen—but the appetite for yield securities was clear.
Chapter 11 – So Naturally… I Met a Guy 13.09.2025 13:25
Chapter 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.
Chapter 10 – Regulators & Financiers 13.09.2025 8:39
Pitching 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.
Chapter 9 – Between Ventures 13.09.2025 6:49
Chapter 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.
Chapter 8 – The Internet, Starts & Stumbles Dot-com boom. 13.09.2025 7:30
Dot-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.
Chapter 7 – Babies, Boats & Windows 13.09.2025 7:10
Chapter 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.
Chapter 6 – Networking, Cables & Unions 13.09.2025 12:54
Chapter 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.
Chapter 5 – Steffey, Sales & Beige 13.09.2025 7:35
Crash 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).
Chapter 4 – The Teak Desk 12.09.2025 6:13
Fresh out of college, I blew a seed round on speakers and a giant teak desk. Lesson learned: desks don’t make revenue, pivots do.
Chapter 3 – The College Detour 09.09.2025 7:13
College 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.
Chapter 2 – Golden Child’s Shadow 09.09.2025 13:25
The evolution of Harkins Enterprises: teenage TaskRabbit before apps existed. Fence-staining disasters, billing “adjustments,” and the painful art of apologizing creatively.
Chapter 1 – Teenage Hustle 09.09.2025 5:21
High-school trauma, garage-door mishaps, and a teenage lawn-care empire. Outsourcing badly taught me more about business than Algebra ever did.
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