In this YouTube monologue, Ryan Deiss answers a viewer’s question about the three things that keep small business owners awake at night. He outlines the primary anxieties: (1) unpaid invoices and the need to get paid first, emphasizing that businesses can structure payment terms to avoid this issue; (2) cash‑flow pressures, especially making payroll at month‑end, and the tension between maximizing expenses for tax reduction versus preserving cash; (3) maintaining a steady flow of work, which he ties to building subscription‑based recurring revenue (MRR). He also expands beyond the three items, noting employee‑related risks such as lawsuits, hacking, and data loss, and reflects on how the nature of problems evolves as a company grows—from product‑market fit concerns to operational and existential questions about purpose. Throughout, his tone is candid, conversational, and occasionally self‑critical, offering both practical advice and philosophical insight into the entrepreneur’s mindset.
Chapters
Careless Echidna 357 asks, as a small business owner, what are 3 things that keep you up at night? I'm thinking about starting my own business and keen to understand what it's like in these challenging times. This is going to be good. Unpaid invoices. The way that you avoid unpaid invoices is you get paid first, and people who say that you can't do this in your business, yeah, you can. We've pivoted plenty of companies. Making payroll at the end of the month. Maximizing my expenses to pay less taxes. If you're worried about making payroll at the end of the month, stop trying to maximize your expenses to pay 'Pay less taxes, dummy.' The voices, that's so good, the voices in my head. Amen to that one. 'Keeping a steady flow of work.' Yeah, this is why building in some subscription MRR is always a good idea. 'That my employees are doing something that'll get me sued, getting hacked or losing access to our data.' 'Just 3, there's more.' That's exactly the point. I think the idea here is that as business owners, we are problem-seeking missiles. What you want to see as your business is growing and scaling is the quality of your problems getting better. So in the early days, you're worried about cash flow and making sales, and that is a problem. But then at some point, you're going to worry about fulfilling all these pesky people that you have, and then you're going to worry about employee issues and things like that. But guess what? That means that you have employees, and if you have employees, that means you sold some stuff. So, I mean, for me in the early days, problem that kept me up at night is, does anybody actually want this thing that I've created? I would definitely lose sleep over employees that weren't working out and having to have difficult, you know, and challenging conversations, lose sleep about cash flow and making payroll at the end of the month. I think any business owner is going to have that as well. And then you get to a point where you just start worrying about what's it all for. So in all these cases, there's always problems. It's just, do the problems get better or do the problems get worse?
