A-mazing or AI-mazing

This isn't any sort of obsequious hype stuff. But if you are an entrepreneur over 50, you are amazing. Creating order out of chaos, generating value, organizing a team, keeping the books, trying to live a life, all of that stuff requires at least a little bit of superhuman ability.

There are people who were cut out for entrepreneurship and people who aren't. That's not a judgment. That's just an observation from somebody who has been 100% entrepreneurial for 20 out of the last 25 years (there were about 5 years interspersed in there where I worked for other people).

But entrepreneurship requires a different mindset, and we've covered it in all sorts of places throughout our discussions. So please, just accept the fact that you're amazing.

The advent of artificial intelligence a few years ago really upended lots of professional work in my field of marketing. We're seeing it harder and harder for early-stage employees to find those roles that used to just get filled by somebody who could be broken down and then built up (sort of like boot camp) so they could survive the rigors of agency life. But so much of that early-stage work was cut-and-paste and run this formula and follow that SOP, and a lot of that is now more easily done through AI.

I'm not exactly sure what's going to happen to the early-stage employee over the next several years. Those roles are definitely going to have to change. But what about you? The older, wiser, more experienced, more capable, more insightful, and more perspicacious entrepreneur on the north side of 50? You might feel like AI is stealing your lunch. I know that in some of the agencies that I work with, the things that I used to tell them are now finding a very similar process inside of ChatGPT or Claude, and they are able to build out some things that I might have worked with them on for a while.

I was actually really frustrated by that, largely because I didn't think that what the AI produced was exactly right for my clients, and it wasn't as personal and as connected. But I kind of got over that because pushing the idea of better quality against the concept of fast, free, and really good was something of a losing battle.

Over time, with enough context, AI actually might do a better job in that early-stage marketing agency (adjust this, change that, here's how your report ought to look, kind of structural development). So, how does an old dog like me evolve?

Founders spend too much time drafting the same kinds of messages. Wispr Flow turns spoken thinking into final-draft writing so you can record investor updates, product briefs, and run-of-the-mill status notes by voice. Use saved snippets for recurring intros, insert calendar links by voice, and keep comms consistent across the team. It preserves your tone, fixes punctuation, and formats lists so you send confident messages fast. Works on Mac, Windows, and iPhone. Try Wispr Flow for founders.

Start flowing free

When I felt the tug to fight against AI disrupting a little bit of my value proposition, I started thinking, "What can I do with AI that I couldn't do before?" It really sort of made me rethink the actual value of what I do. And it made me focus more on how I could use AI to adjust what I do so that it has more impact, more appeal, and is pretty bulletproof.

Do you remember the movie War Games? (OMG, I loved that movie - I thought it made me want to be a computer prodigy - upon reflection, I think it made me want Ally Sheedy to fall in love with me, but we can talk about that some other time…) If you don't remember, there was this AI-powered machine called WOPR that predicted the outcome of nuclear attacks. Everybody's favorite teenager Matthew Broderick hacked into this giant Department of Defense machine, was playing games with WOPR and suddenly it became real. That was AI gone haywire and out of control. I know that many people are afraid of that, but let's just think about you and your entrepreneurial journey for a minute.

You ought to think about AI as an opportunity rather than a threat. AI is sort of like your own personal anti-missile defense system. At this point, AI is mostly clever and not smart - so you have the opportunity to imbue your expertise with AI-powered defenses.

This IS an extraordinary time to be an older, perhaps slightly wrinkled, perhaps a little more forgetful, but hugely high-impact entrepreneur.

This guide from Deel breaks down how to build one global hiring system. You’ll learn about assessment frameworks that scale, how to do headcount planning across regions, and even intake processes that work everywhere. As HR pros know, hiring in one country is hard enough. So let this free global hiring guide give you the tools you need to avoid global hiring headaches.

Download the free guide today

A lot of what I do with my whippersnapper entrepreneurs is teach them about selling. Because sales actually is really hard. One of the things that they really don't do is focus on what happens before a sale? What do you need to know about your potential prospect? What do you need to know about their business? How it connects to your service so that you can have a really super duper amazing discussion with someone? The other thing that they don't do is they don't really review how those discussions went. I've found that it's largely "that was a good discussion", "that was a bad discussion".

There's a bunch of learning that happens when you review your discussions. For a long time, my clients would send me their sales calls. I would review them by listening to them or reading the transcript and giving them feedback about things that could happen better or give them ideas about how to follow up. On the whole, they found it really, really useful. But one of the things that didn't happen very often is that they didn't track it over time.

They didn't adjust their pre-call research in order to ask the best questions which turned out to create the best calls. I wanted to get this in the hands of more people and it was super-duper frustrating to me that it was too expensive for a lot of the folks that needed it the most. They would have to be in a coaching program with me or a consultation with me that cost thousands dollars.

I was using AI to review my own sales calls. I started seeing patterns that I never noticed. I started finding ways to get better - but only because I was able to tell AI about all of the stuff that I know about sales and selling.

After a few months of this, I thought: "Wow! I am using AI to coach myself. Why don't I take that and start coaching people who just couldn't afford my services?"

I just asked AI: "How would I turn this into a product? How would I turn this into something that makes sense to buy?"

I built something called SalesOS Call Lab (and it’s more detailed, paid for cousin, Call Lab Pro). I don’t know anything about building an application, but AI gave me the opportunity to BUILD SOMETHING THAT I AM PROUD OF and adds real value. I liked that so much that I built Discovery Lab and Discovery Lab Pro, too.

Check out Call Lab report examples & Discovery Lab report examples - these are all built by someone who’s most advanced programming skill was building some ASCII art in 11th grade computer lab in 1984.

you know stuff that is amazing. You understand how to think about problems in a very sophisticated way. You understand what kind of information the people who have the problems that you can think about need.

Trust me, if I can create something that I am astounded that I built, I 1000% know that you can do something AI-MAZING, too.

chapter neXt is a newsletter/community/guide for entrepreneurial folks in their 50s and beyond. It is published by Julia Kelahan (check her out on LinkedIn, her amazing strength-based learning center & her ADHD & Executive Function coaching business) and Tim Kilroy (check him out on LinkedIn & his agency growth business & his agency-focused newsletter). They are the proud parents to 5 kids & live near Boston.