Ep 218 - The Road Less Stupid

Flip and Danny discuss Keith J. Cunningham's book on intentional thinking time for business owners. The core idea: schedule daily time to think deeply, because better ideas emerge after sustained questioning. They share how the book pushes past shortcuts and faulty assumptions to shift from operator to owner mindset.
Hey, everybody.
Flip and Danny here, founders of the Freedom Real Estate Group, family of companies. And welcome to another episode of our.
Podcast called Freedom through Passive Income.
That's right. And welcome to another episode. And this is a fun episode. This one is. We're going to talk about a book that you got.
Yes.
And this one, the. The title of this is called the Road Stupid.
Yes. I love this book. And so for those of you who are watching and not listening, you can see the book right here. So if you want to buy a copy after listening to this podcast, you can. I really feel like this was recommended to me by Steven Libman and he. It really changed his business after going through it. And at the top of the book, it says, avoiding the dumb mistakes that sabotage growth, profits and business success. And Flippo will read the inside panel because I think it's super powerful, but it really makes you stop. For those of us who just kind of go fast and furious because we have so many ideas and so many things that we want to do and we're fast at decision making, sometimes it's a slowing down that really finds the gold. Right. I don't know that Steven is necessarily like that. He goes super, super fast all the time, and that's why he found it powerful. I'm sure. You know, he had. He has a totally different set of circumstances of why it was so great for him. But I do remember him saying, just being intentional about every single morning, sitting down and having this thinking time. And that's what they talk about in this. So I'll let you read the. This panel right here and then I'll talk a little bit about a couple things that I found super, super interesting about this book and why I love it so much.
Well, and just to let you know though, if you are listening and not watching, it's the Road Less stupid Advice from the Chairman of the Board by Keith J. Cunningham.
Yes.
So that way, if you want to go out and book it, book it, book it. If you want to buy it, buy the book. But the. The insert right inside the front cover, it says, smart people do dumb things. Here's the proof. How much money would you have right now if I gave you the ability to unwind any financial decision you have ever made? It turns out that the key to getting rich and staying that way is, is to avoid doing stupid things. The vast majority of dumb tacts in both our lives as a direct result of three things. Number one, generalizations which kill clarity. Number two, obsessing about Oz instead of the yellow Brick road. And lastly, number three, faulty assumptions, ignoring risk. So here it is in a bummer sticker. Operators react and sweat. Owners think and plan. Yes, it all hinges on thinking time.
That's what I said. That's right. I want to be in the owner's box, right? Not the operator's box. And we have been in the operator's box for a very, very long time. And I really want to start.
There's another box.
Yes. I really want to start getting wiser about everything that we do. And far more intentional than just going fast. And we've found great success in going fast and keeping things simple. And we're good at the decisions we make. They're not all perfect, but the good ones far outweigh the bad ones. And we've been very fortunate to be surrounded by some really incredible people that have joined this team, that are helping lead this team now. And we're just blessed. But, you know, we always need to pursue excellence, right? Greatness and wisdom and things like that. So always constantly trying to get better. And this book has just been really impactful. And it's gonna be something that, especially as we move to Florida, I'm gonna have a room where this is going to be my thinking time room. And every single morning, I'm gonna be very intentionally using this time to. To ask the question. So he goes, I'm reading in the book right now, but thinking time, the process. I found something very interesting. So we have the physical book. We also have it on audible. Because when I'm walking on the treadmill, then I like to listen to books. And the one thing, the key takeaway for me when he was talking about this, he said, I put aside 60 minutes to go there, and I have some questions written down already. And he always puts a dot. So if he'll have a question that he's asking himself, and then he will put, like, a little bullet point, and he'll answer and then put another bullet point right away, because it's telling his mind there's another bullet point there. You have to think of another idea. And then. And so it's immediate after I. Yeah. And you have to just keep on doing it. And that's how he prompts his head to always be looking for another solution. And he says, in this hour, there's some jokes in there. I'm not going to even lie. I'm just now laughing when I heard him say how he preps for this hour. But the thing I wanted to share here with you was the third. Third. So I'LL read this. He said, remarkably, I found my better ideas tend to emerge during a pattern known as the third third. The first third of my ideas on any given day are typically the obvious ones. The second third are variations on the first third, but the last third tends to be the more robust and frequently are where the juice is found. So he's really kind of sharing the story of, hey, your first ideas, those of us who are fast decision makers, they're the obvious ones. Just go, yes. Yeah. But the really, really good ones, the ones with gold, are the ones where you sit there and you ask yourself a question and you create that dot and you answer, answer, answer, and your answers start getting better. And the third third for him is frequently where he finds a goal. And I thought, wow, that's really powerful. And that makes such sense because you require your mind to really marinate and answer something, and you've also required it to go somewhere it doesn't usually go because you're going so fast.
That's funny you said marinate, because that's exactly what I was thinking, too.
Yeah. So then the other thing I was gonna share real quick is I just pulled up a chapter. This one's called, mmm, Kool Aid. And in every chapter, he talks about a story, and then he loves these bumper sticker ideas, which reminds me of Matthew McConaughey. Bumper sticker or the book?
Well, that's the book. Matthew McConaughey's book. But the name of the book.
No, no, no. I was just. It's Green Lights or something.
Yeah, Green Lights.
Yeah.
But every so often in that book, if you listen to the aud.
Awesome.
Because Matthew McConaughey reads it, he'll just go, bumper sticker.
So this gentleman does the same thing. And it's really kind of funny. But I just wanted to read you on this Kool Aid chapter, some of the things, because at the end of every chapter, he will give you the questions to ask. Right. So you don't even have to come up with questions, because we all know the quality of the question is directly related to the quality of the solution that you find you have to be asking the right question. In fact, he talks about that. He says, sometimes I start my questions with phrasing it this way, and then I'll phrase it a different way to see if I come up with different ideas or answers or if that takes me down the path closer to where I'm trying to go. So he'll just change his questions. And it's really interesting. So here, real Quick, because I know we're running out of time thinking time. At the end of this one, he says, where are we compromising by looking for the door marked wow? What shortcuts are we attempting to take that are not really shortcuts, but rather mirages of greed, laziness, or impatience? I was like, oh, that's a good question. What skills do I need to master to attain the success I want? I thought, this is a good question for you guys, because I'm thinking of you guys whenever we do scripts. I'm like, how does this relate to those who are trying to achieve passive income? And I thought that was a good one. What skills do I need to master to attain the success I want? And that's really evaluating opportunities, right? And trusting the team. Realistically, how much additional time and practice are required for me to attain my outcomes? Who can I hire as a coach or a mentor to help guide me and hold me accountable? Where do I need to practice to improve my game and thus deserve the success I want? And where do we need to pick up the level of intensity in how we are playing this game? So I always call this the game of money, right? And so those are just questions. And I just love that because I'd be walking the treadmill and he'd be talking about something in business and, like, he has a chapter about CEOs and what they should never delegate. And I was listening to it and listening to it, I was like, oh, those would have been good questions to ask myself a year ago. So it's just a really powerful book. And I think whenever you have these moments where you say, this one's going to change my life, you have an obligation to share it with others. So I said, let's do a podcast about this one, because this one is going to change the game for us. And it's already forcing me to slow down and really, really think about the right solutions and answers to questions.
And again, it's called the Road. Less Stupid. Advice from the chairman of the board from Keith J. Cunningham.
Yes.
Well, we hope that you enjoyed this episode. Make sure you're heading on over to our website, freedomcapitalinvestments.com and join our investor club. And we also have the swag on there, but we're also on Facebook and LinkedIn and all the social media, so let us know how we're doing. But we like to end all our episodes with Invest Smart, Live Happy. Bye, everybody. Nothing on this show should be considered specific personal or professional advice. Please consult an appropriate tax legal, real estate, financial or business professional for individualized advice. Opinions and information on this show are not guaranteed. All investment strategies have the potential for profit or loss.
Sam.
More from Dani

Physicians and High Earners — What Real Estate Can and Can't Do for Your Taxes









