An Entrepreneur’s Hustle, Humor, and Poorly Timed Brilliance
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 to tell the tale.
Episodes

Oct 2, 2025

Sep 13, 2025
Sep 13, 2025
2 min
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.

Sep 13, 2025
Sep 13, 2025
13 min
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.

Sep 13, 2025
Sep 13, 2025
8 min
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.

Sep 13, 2025
Sep 13, 2025
6 min
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.

Sep 13, 2025
Sep 13, 2025
7 min
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.

Sep 13, 2025
Sep 13, 2025
7 min
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.

Sep 13, 2025
Sep 13, 2025
12 min
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.

Sep 13, 2025
Sep 13, 2025
7 min
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).

Sep 12, 2025
Sep 12, 2025
6 min
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.



