Off Payroll

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 others think instead of how you speak. Then you start hearing the maybes, I thinks, literallys, ums, and likes. You hear yourself mean well yet sound rude. Next, you think of the word and stop yoursel...

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 isn't, or why revenues don't add up on busy days, this episode was made for you. You'll hear my description of the tradeoffs to each current parking management solution and then I'll explain ours at L...

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 short. Why do they predict such a timeline? What happens if the gap doesn't close in five years? I had no idea where to even start to get to the bottom of this. So I asked a founder who lived through the...

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 top six business pet peeves from entrepreneurs. 1: Being secretive about business ideas. 2: Splitting attention between more than one business. 3: Saying you need outside investment to have a business. 4...

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 price, double your customers, or double how long they stay. Which do you pick? One of them I choose every time. Thanks for listening to Day 8 of Off Payroll. We’re making as many episodes as possible i...

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 profit versus customer acquisition cost. It's what makes businesses the greatest opportunities for wealth. Understand this and demystify what running a business really means. Thanks for listening to Day 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 honest and how to catch yourself rationalizing your own actions. Thanks for listening to day 6 of Off Payroll. Check back tomorrow to see where we go next.

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 recurring problems are just as difficult to deal with and can be even more so than sudden ones. Thanks for listening to day 5 of Off Payroll's October's marathon. See you tomorrow to see where I go next...

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 your own time into being early, late projects into quick deliverables, and ordinary days into great ones. Thanks for listening to day four of 30 podcasts in 30 days. Tune in to tomorrow to see where...

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 own good. A form builder that should charge way more than it does. And a co-working space with every benefit you could think of. Once you’ve recognized it, you’ll see it everywhere you look. Thanks for l...

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 holding you back, and how time is your superpower. This is day two of Off Payroll's October marathon.

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 games, and how later really means never. I hope this helps you speak so everyone understands what you're trying to say. October's vocabulary chopping block: you know what I mean basically and essentially...

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 asking if you could raise your prices. Along the way I'll tell you how I would run a septic tank business so you would be excited to get your plumbing fixed. Thanks for listening to my first ever podcast...