The Human Side Of Business With Mike Michalowicz - TWMJ #1056

Mitch Joel (0:00)

Well, hey there and welcome to episode number 1056 of Thinking With Mitch Joel. It's Sunday, October the 4th, 2026

Let's get on with the conversation.

What if AI doesn't replace us, but it exposes us? Exposes the work we never really needed to be doing. Exposes the so-called best practices everyone has been copying, and exposes the difference between being productive and actually doing something meaningful. I think this is the bigger conversation we need to have, and that's why I'm having it with my old friend Mike Michalowicz. It unexpectedly goes in a whole bunch of different directions. You might know Mike as the bestselling author of the famed book Profit First, and he's got many other books that are focused on helping entrepreneurs build healthier and more resilient businesses. His latest, The Money Habit, takes his thinking into personal finance, and Mike is basically describing his larger mission simply as the ability to eradicate entrepreneurial poverty, which I love. But our conversation is expanding well beyond this theme of his new book. We're going to look at what AI might actually do to small businesses, why greater efficiency probably won't give us much more freedom, and whether technology can actually be used instead to create more space for us to operate in what we're uniquely good at, which is what I am hoping for. And we even wrestle with books, writing, creativity, and why success is rarely the meritocracy we would like to imagine it to be. So new technology may destroy certain ways of working, but it can also become the tool that enables entirely new forms of human expression, work, and entrepreneurship. And maybe, just maybe that's the opportunity in front of us now. Enjoy the conversation.

So who are you and what do you do?

Mike Michalowicz (2:07)

I'm Mike Michalowicz. I'm the author of Profit First, along with about 10 other books, and I'm on a mission to eradicate entrepreneurial poverty.

Mitch Joel (2:15)

I love it. How are you, my friend?

Mike Michalowicz (2:17)

Good. I wish people heard the pre-recording, the lewd and lascivious commentary that was thrown back and forth. It ended with a Mike Curious, which I thought was absolutely brilliant.

Mitch Joel (2:27)

You threatened to show a nude photo of yourself, and I said, I'm Mike Curious.

Mike Michalowicz (2:31)

Yes. I printed out a photo. It's not myself nude, but it really has me inspired around AI and the future of humanity. It's a photo from way back.

Mitch Joel (2:43)

Okay. Well, we're going to get into all those topics. You got a new book out called The Money Habit. We've spent time personally hanging out, so I feel like maybe it hasn't been topless, but close.

Mike Michalowicz (2:51)

Close. While we were in Miami, we were sitting out on a massive deck at our mutual friend, Dory Clark's place.

It was unfortunate. I think you were unable to make this last trip, and you bring an intellectual stimulation to that group that is necessary. I think sometimes a contrarian intentionally to bring around, to break out of that group think, and so I missed out this go around because I noticed like, we're getting a little too complimentary of each other, too much confirmation bias, and I was like, we need a Mitch Joel in here.

Mitch Joel (3:22)

So that's interesting.

Contrarian. I don't know. Lately, I've been thinking a lot about this, and this fits in your wheelhouse as well. I love your perspective on this because I know I get that, and I get that because I think I am somewhat rigorous and thoughtful in a world where I feel like I might be being too thoughtful. In particular, I was thinking about the simulation to marketing, and maybe I just overthink things, or maybe I think them through too much, or maybe I'm too analytical, or maybe I do need to dumb it down, and then I start questioning whether I should do that versus being what I prefer to be, which is more rigorous.

Mike Michalowicz (3:57)

I think we all need others, and so I noticed in that group that my thinking was elevated specifically because you were there and because Dory was there and Jenny, and everyone, and they all came with their perspective. So Jenny Blake, for example, has this bubbly, enthusiastic personality, and it's nice to have a cheerleader sometimes around something to push me over the edge. You were the critical thinker, not saying criticism, just critical thinker and really going into the detail and exposing things. I think what happened at times was someone had an idea, and the rest of the group affirmed it, and then there was this excitement, you got to do it, and yeah, this is it, we're all in, and then you were coming about and saying, well, hold on, let me give another perspective.