The War on Mediocre Business

I read a book. I had what I call an entrepreneurial seizure. And then I spent nine months forcing a broken sales strategy on my team and calling it conviction.Here's the real story, and the leadership lesson I didn't expect to learn from it.In this episode of From the Trenches, Scott Monday walks through one of his most expensive leadership mistakes: a new sales model he built from scratch, rolled out top-down, defended for three quarters, and finally had to reverse in front of the people who had been telling him it wasn't working.The lesson isn't "listen to your team before you make decisions." That's a cliché. The real lesson is what you do after you've already made the wrong call, and why reversing a public mistake is one of the strongest moves a leader can make.If you've ever held the line on a bad decision longer than you should have, this one is for you.🔔 Subscribe for new episodes every other week.📬 The War on Mediocre Business: operator stories and business tools, every Saturday: https://scottmonday.substack.com0:00 - Arrogance Kills a Business0:20 - The Context: Two Companies, One New Product0:40 - The Mistake: Bold Declaration, No Discussion2:16 - The Moment: Jake Comes to Me3:05 - What It Cost3:26 - The Real Lesson: What Do You Do After the Wrong Call?4:26 - Bold Leadership vs. Stubbornness5:03 - Authenticity Is the Foundation5:22 - How I'm Rebuilding It Right This Time5:42 - The Question for You This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit scottmonday.substack.com

Toys R Us once sold one in five toys in the United States. Then it was completely gone. Here's what actually killed them, and why the same mistake is happening in businesses right now.In this episode of Whatever Happened To, Scott Monday unpacks the rise and fall of the world's largest toy retailer. From Charles Lazarus's category-killer strategy in 1957 to the leveraged buyout that buried Toys R Us in $400 million in annual interest payments, the collapse has a lesson that goes far beyond debt and Amazon.The real culprit: the messy middle. Trying to win on price, quality, and experience, and ending up winning at none of them.If you're running a business in the $2M to $20M range, this one hits close to home.📬 The Scott Monday Newsletter — business stories and operator tools, every Saturday: https://scottmonday.substack.com0:00 - The Memory Hook0:47 - Quick Intro1:03 - The Rise of Toys R Us3:11 - The Crack and the Fall6:18 - The Operator's Take: The Messy Middle8:40 - What This Means for Your Business This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit scottmonday.substack.com

In January 2023, I launched my third business with a color-coded, detailed proforma. By the end of 2024, I had lost nearly half a million dollars.This is the TBS story — and the four lessons I learned the hard way.I'm Scott Monday. I run two businesses in California's Central Valley. Trinity Builder Solutions (TBS) was my attempt to move into the commercial stone market after years of running kitchen & bath CRATE. It was a new industry, a new model, and a fresh start at 43 years old.It did not go the way I planned.0:00 — Lost nearly $500K on my third business0:22 — Who I am and what TBS is0:44 — The TBS story: January 20231:06 — First gut punch: key team member resigns mid-20231:46 — Proforma off by 2x + COVID/interest rate headwinds2:09 — End of 2023: $289K revenue, $239K loss2:38 — 2024: lost even more — the decision to keep going3:00 — Mid-2025: a hard call on a key employee3:19 — End of 2025: things start to turn3:42 — Lesson 1: Forecasting a new business is mostly fiction4:00 — Lesson 2: External forces will happen — pivot quickly4:17 — Lesson 3: Starting over at 43 is nothing like starting at 284:41 — The hunger gap: dumber but driven vs. smarter but comfortable5:03 — Lesson 4: Relationships matter in B2B just as much as B2C5:22 — How we changed our approach in mid-20245:40 — Where TBS stands today5:58 — My question for you + CTATBS is not a success story yet. But it's not a cautionary tale either. I'd do all of it again. The 39 months of having my face rubbed into the ground made me a better leader and a better business owner.If you've ever built something on assumptions that turned out to be completely wrong — I want to hear your story in the comments.Subscribe for a new episode every two weeks. Real lessons from real businesses, no fluff.I write about this every week in The Scott Monday Newsletter: https://scottmonday.substack.com This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit scottmonday.substack.com

MySpace had 100 million users and more web traffic than Google. Then they made one decision that started a five-year collapse — and a decade later, ChatGPT might be making the same mistake.In this episode of Whatever Happened To, I break down how MySpace went from the most visited site on the internet to a $35 million fire sale — in five years. The short answer: they stopped doing what made them great and started chasing ad revenue instead.I'm Scott Monday. I run two businesses in California's Central Valley and I'm morbidly curious about what makes businesses succeed and fail — especially the ones we all grew up with.0:00 — MySpace had more traffic than Google0:23 — What this series is about0:39 — My personal connection to MySpace1:19 — How MySpace was built (2003 to 2004)2:17 — 25 million users and Rupert Murdoch's $580M buyout3:02 — News Corp sees "eyeball inventory"3:26 — The $900M Google ad deal3:46 — Why it was a trap4:25 — Facebook rises while MySpace falls5:52 — The core lesson: optimized for the contract, not the customer6:11 — Is ChatGPT making the same mistake?7:50 — What this means for your business9:25 — The question every business owner needs to ask10:05 — Subscribe and final thoughtThe lesson isn't just about MySpace. It's about the small decisions you and I make every day that slowly erode the thing our customers love. MySpace wasn't run by idiots. They were run by smart people who made a series of bad decisions — each one looking reasonable in isolation.Don't make the same trade.Subscribe for a new episode every two weeks. No fluff, no motivation talk — just real lessons from real businesses you actually remember.I write about this stuff every week in The Scott Monday Newsletter: https://scottmonday.substack.com This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit scottmonday.substack.com