In this advisory video, Ryan Deiss (Speaker A) evaluates the most critical competencies for CEOs and founders of companies generating $20 million or more in annual revenue. He assigns each skill a priority rating (S, A, B, C) and explains why the rating matters at this growth stage. The core messages are: the founder must become the chief storyteller and public spokesperson; delegation should evolve into building a team of leaders rather than merely assigning tasks; sales should be handed off to dedicated professionals; decision‑making requires robust frameworks to avoid catastrophic errors; negotiation becomes a high‑frequency, high‑stakes activity; copywriting, while valuable, should be outsourced to specialists; recruiting transforms into a talent‑acquisition engine that the CEO must champion; financial literacy and solid accounting systems are non‑negotiable; and public speaking is essential for brand representation. Throughout, Deiss stresses that neglecting any of these high‑priority areas can jeopardize the business’s continued scaling.
Chapters
Founder skills at $20 million. Storytelling. S. At $20 million, you are the primary spokesperson for your company. If you have not figured out how to tell your company's story effectively yet, that is a problem and you're probably gonna lose your job. Delegation. I'm gonna say C, just because you should have already figured out the basic aspects of delegation, and at this stage, it's no longer about delegation. It's about building a true team of leaders that can just take stuff over, that you're not delegating tasks. Sales. B, it's important but you shouldn't be doing it. You should have people that are doing it. Decision-making. S. Businesses scale at the rate of good decision-making and if you don't have solid frameworks for decision-making at this point, you run the risk of making a catastrophic decision that can upend your business completely. The stakes are just too high. Negotiation. A, you're going to be doing a lot of negotiating at this point and so understanding how to do it in a way where you don't come in, you know, looking like a jerk or you don't have somebody run roughshod over you, it is a skill and now's the time to build it. Copywriting. C. And I'm not saying that copywriting isn't valuable because it is. I think it's one of the single most valuable skills that you can have. You should just have copywriters on your team that can do that for you. You need to be thinking, how do I take the copy they've written and tell a story about it? Recruiting. S. At $20 million, the business becomes a recruiting agency, and so you should have recruiters. But also a big aspect of your job is figuring out how you can help streamline that process and also do the networking to get the really important people because if somebody's going to come work for you at that level, they're going to want to talk to the CEO. Financial literacy. I'm going to say A, it's important but gosh, I really hope you figured out some of these things by $20 million. If you haven't though, it's an S. It's terrifying and I have known people who are running $20 million plus businesses still on like spreadsheets. They don't even have a basic accounting system so we can't get that but I'm gonna say A only because you should have already had some of that by now and you should have good finance people around you. Public speaking. A, you are your company spokesperson. You need to have the skill, the ability to go and do that, whether it's on a stage or whether it's on different social channels.
