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Speak Like A CEO | November Ep 13
Lazy language is the fast food of the 21st century.There's four steps to remove lazy language, each matched to levels of awareness.At first you wonder why people don’t understand you. You blame how…
No More Lot Sitters | Ep 12
This episode introduces LoRalot.The parking system that enforces itself.If you own a grocery store, a bank, a mall, a restaurant, or a parking lot, and wonder why your lot is full but your building…
Trillion Dollar Questions | Ep 11
Two trillion. That's the amount that one of the big three consultant firms thinks AI models needs to generate in annual revenue by 2030.Today? AI makes 50 billion dollars per year.1.95 trillion…
Quiet Dealbreakers | Ep 10
These six things that entrepreneurs do drive me crazy. I hear these online, at fireside talks, and I hear these all the time at entrepreneur clubs and incubators at UC San Diego. Listen to hear my…
The Magic Genie | Ep 9
It’s your lucky day. A magic business genie grants you a wish. But you only have three options. Are you ready? You only get one shot at this.Nothing else will change and you can either: double your…
Built to Last | Ep 8
How do you build a profitable business that lasts, not just looks busy?From sunset army crawls to storefront math, today is about the one ratio that all of business boils down to.Lifetime gross…
The Common Thread Between Criminals and Friends | Ep 7
What makes it more likely to cheat, lie, and steal?This is what criminals, your friends, and even yourself all have in common.You'll learn how to control environments to make people more or less…
The Slow Decline | Ep 6
I talk about the trap that keeps us stuck in old habits. It’s what happens when you get comfortable with a slow decline. The same reason why a leaky sink goes weeks without getting fixed. How small…
Expectation Arbitrage | Ep 5
I share the story of how I found the superpower that everyone has but no one uses. I discovered it when I needed it the most and I call it expectation arbitrage.You'll learn how to turn showing up on…
The Goodwill Margin | Ep 4
In this episode, I share how free picnics taught me what I call the goodwill margin. The gap between what you pay and what you get. You’ll see it show up in a running app that’s too useful for its…
Solve For The Decade | Ep 3
After years of false starts and new beginnings, I finally learned the rule that changes everything.In this episode, I share the failures that burned this into my brain, why chasing quick wins is…
The 8 Words I'm Forgetting Forever | Ep 2
These eight words make you sound lazy, vague, or like you don’t care. I share the story of how I embarrassed myself in front of 200 classmates, why it's important to get specific to win volleyball…
S1E1 When “Affordable” Doesn’t Matter | Ep 1
What does a septic backup have to do with your business? A lot. I break down the four unsexy and unheard of way to make your business stand out. The story start with a plumbing diaster and ends by…
Frequently Asked Questions
Off Payroll has published 13 episodes since August 2025, covering topics in Business, Entrepreneurship.
Off Payroll is currently dormant with new episodes weekly. Average episode length is 14m.
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