Off Payroll

About Off Payroll

Actionable episodes on what not to do to grow your business.

Publisher

Jay Rosencranz

Category

business

Language

en

Explicit

No

First episode

15 Aug 2025

Latest episode

6 Nov 2025

Latest episodes

13 episodes in the feed.

1. 

   6 Nov 2025

   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 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 yourself before you say it out loud. Lastly, you’re back to being unaware, but now people lean in to hear what you have to say. You sound like you belong in the board room. If you turn on the jargon, you turn on the smoke machine. Pick one of these to stop saying this month. Lazy labels: Turn them into actions. "The opposite of slow is flow" Especially Very Thing Kind of Corporate Jargon Innovative Robust Seamless Impactful Cutting-edge Non-committal ly words. Probably Possibly Potentially Personally Ideally Hopefully October carry-overs: you know what I mean basically essentially I think just stuff something maybe interesting Let’s do it later Cut it if it’s vague, too polite, or too proud.Use it if it’s short, simple, and observable.

2. 

   30 Oct 2025

   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 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 LoRalot. To counteract my bias, I want to give you a framework you can use to decide if this is right for you. Any parking management solution needs each of the following three pillars. If it's missing only one, then lot sitters love you. Loud honking, customers circling, and the occasional swear word will all be the too common appearance. Here are the three pillars: You need a way to track the cars. Which means you know exactly which parking spots are occupied at any time. A way to time the cars. How long each car has been in your lot and when they overstay the time limit. And a way to alert to tow the cars.To quickly let your staff or tow partner know if needed. Track, Time, and Tow. Use this framework to make informed decision for yourself. How does how you manage your lot align with track, time, and tow? Here's how we approach managing your parking lot: Sensors are laid in the ground in each spot. They see when cars come and when they go. They update a live map. It shows grey spots open, green spots taken, red spots overstayed. If time runs out, an alert of your choice is sent. Warn, ticket, tow, or anything you'd like. No need to tow if you don't want to. Next, the sensors collect lots of data. Average stay time, total cars parked per day, peak hours, busiest spots, turnover percentage, legal hours, illegal hours, occupancy rate and more. But I truly believe that unless data is applied it’s useless. If it’s a metric that sits there and it doesn’t change behavior you don’t need it. We focus on the actions to take that make your lot so that people parking in it are happier and spend more. We avoid expensive cameras and it's privacy friendly. Plus no more running around. Run our self-enforcing solution through the track, time, and tow framework. Up to you if it checks each box. If you’re listening before we talk, it’s very nice to meet you. We start with our free 7-day No More Lot Sitters System. To see if it's a good fit for you. Looking forward to answering any questions you may have. Thanks so much for your time.

3. 

   21 Oct 2025

   Trillion Dollar Questions | Day 10

   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 internet bubble and has a company with a market capitalization of 2.27 trillion. In my mock interview with Jeff Bezos, he teaches us about the potential of an AI industrial bubble. And what it would be like to live through it. Before my interview, I knew that billions of dollars were being invested in data centers and GPUS, but I didn't realize what could go wrong. Has overexcitement led to overinvestment?Is this really the price of progress? This episode is my attempt at grasping at a simple understanding of the future of AI. Thanks for listening to day 10 of Off Payroll.

4. 

   19 Oct 2025

   Quiet Dealbreakers | Day 9

   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: That students are taught how to pitch instead of how to build. 5: Focusing on new inventions instead of proven playbooks. 6: How partnerships are formed without a good reason. The pattern between all of them is ego dressed up as strategy. I hope now you see different perspectives. Thanks for staying with me. See you tmw! We're talking about the state of AI with Jeff Bezos.

5. 

   16 Oct 2025

   The Magic Genie | Day 8

   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 in October. Check back soon to see where the intro goes next.

6. 

   15 Oct 2025

   Built to Last | Day 7

   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 of Off Payroll. Come back tomorrow to see where we go next.

7. 

   14 Oct 2025

   The Common Thread Between Criminals and Friends | Day 6

   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.

8. 

   8 Oct 2025

   The Slow Decline | Day 5

   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.

9. 

   6 Oct 2025

   Expectation Arbitrage | Day 4

   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 Off Payroll goes next.

10. 

    4 Oct 2025

    The Goodwill Margin | Day 3

    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 listening to day two of Off Payroll’s October marathon.

11. 

    3 Oct 2025

    Solve For The Decade | Day 2

    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.

12. 

    2 Oct 2025

    The 8 Words I'm Forgetting Forever | Day 1

    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 i think just stuff and something maybe interesting later Find sharran's episode here (https://sharran.com/episode260/)

13. 

    15 Aug 2025

    When “Affordable” Doesn’t Matter

    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 episode! P.S Not building business stated in pod. Lesson: work on that you'll be excited to work on for a decade.

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

Apple Podcasts (US)

5.0 / 5

2 ratings

Spotify

5.0 / 5

5 ratings