In this episode of the Real Entrepreneur, Mike Michalowicz reviews a scene from the TV series Ted Lasso to extract actionable business insights. He frames the discussion with a typical YouTube call‑to‑action, then walks through a darts‑playing sequence between Ted, Rupert, and Rebecca, using it as a springboard for several lessons. First, he highlights the power of curiosity over judgment, citing Ted’s realization that his critics never asked questions. Second, he points out that being underestimated can be a strategic advantage, illustrated by both Ted’s underdog status and a story about Thomas Gorney of Nextiva. Third, he draws a parallel to poker strategy: players who appear weak but stay in the game often hold strong hands, encouraging leaders to stay humble and observant. Fourth, he emphasizes deliberate practice, noting Ted’s decades of dart‑playing practice as a model for mastery through repetition. Throughout, Mike intersperses humor, personal commentary, and repeated prompts to subscribe and engage, concluding with a reminder to keep learning and practicing.
Chapters
You know, you've seen it. You've seen that show Ted Lasso, and we're going to review it today. Here's a guy from the southeast who goes to northeast, not of the United States, but of the world, the planet ends up in the UK and is transformative and his personality and his wholesomeness and I don't know, it's amazing lessons. So here's the deal. Hit the notification bell, push the subscribe button, and let's dig into this episode. Don't forget, if you do those two things, the subscribe button, notification bell, you don't miss a single future episode. And that's where I review movies, TV shows, video clips and give you the austral insights. And Ted Lasso's packed with them. Here we go. He's a little bit of a hustler.
So, Rupert, y' all take your darts over here pretty seriously, huh? This. And what's a billiard game? You all do. That sounds like a brand of cookies.
Snooker.
That's it. That's the one, yeah. Boy, I'd love to curl up on a couch under a weighted blanket, watch you've got mail and devour a box of snookers. See, we got here. Hey, there it is.
Do like dots too.
Oh, they're okay. I'm more of a, you know, a cornhole man myself.
Yeah.
Oh, how about a game?
I'll show you Right here's asking to play a game. I'll tell you something like this. That there's an observation here is that the person who shows strength from the get go, it's often bluffing. And the person who shows weakness from the get go, if it's packed or backed with confidence or comfort, usually is strong. It's an old poker strategy. Watch the players who are kind of playing loosely or non caringly, kind of feel obligated to stay in the game. Those are usually the best players and have strong hands.
I mean, we could maybe wager, say £10,000.
Well, as my doctor told me when I got addicted to fettuccine Alfredo, that's a little rich for my blood. How about this? If you win, I'll let you pick the starting lineup of the last two games of the season. But if I win, you can't go anywhere near the owner's box. At least not while we're back at st in charge.
Ted, what the hell are you doing? Well, I believe some folks call it.
White knight, but I don't know if.
It'S full of my gut.
It's okay.
It's what do you think you're on?
Okay, double in, double out.
Whatever you say, R. Dukes. Yeah, just let me know if I'm winning or losing, all right?
Oh, I forgot I had these on me.
Oh, wait a second, I forgot I'm left handed.
So that's funny. So now we know the two champions are going to go at it foot to foot or head to head. Or head. Head to foot. Foot to head, Toe. I don't know, but they're going head to head. That's the word I was looking for. And that was the warning I shared with you. When someone comes off weak, unknowing, but stays in, has a kind of underlying sense of confidence. Be careful. But the other guy has starts with him. So let's see what happens here.
I was going to be a hoop.
William. Rupert. Get in.
Shut your stupid little twat mouth or I'll shut it for you.
Shall I be giving you the lineup card now, Ted? I shall be putting your base back on defense where he belongs.
That's exactly what I said, didn't I?
No, not all Ted's fault. My ex wife's the one who brought the hillbilly to our shores. I know she's always been a bit randy, but I never thought she would over an entire team.
Hey, better manners when I'm holding the dart, please.
I'll tell you, lasso's got some good, good onliners, mate.
What do I need to win?
Two triple twenties and a buff and sunlight.
Good luck.
You know, Rupert, guys have underestimated me my entire life. And for years I never understood why. I used to really bother.
People have underestimated him his entire life. I'll tell you, that can be your biggest advantage. I remember I had a meeting with Thomas Gorney. He's the founder of nextiva. And we were talking privately and he goes, you know, people underestimated me. He's from Eastern Europe, moved to Germany. He has a European accent, heavy. He only learned English in his late teen years. And he goes, because I have an accent and speak slowly, people think, I think slowly. And that's been my biggest advantage. I fumble intentionally, but looks like he's fumbling and slow and people disregard him. And then he comes in and dominates. He's been extremely successful. Check out nextiva and his prior companies, you'll see what I mean. Underestimating people is very dangerous. So be careful. And if you're the one who's underestimated, oh my gosh, is that an opportunity of strength?
But then one day I was driving my little Boy to school. And I saw this quote by Walt Whitman. It was painted on the wall there. It said, be curious, not judgmental. I like that. So I get back in my car and I'm driving away and all of a sudden it hits me. All them fellas that used to belittle me, not a single one of them were curious. You know, they thought they had everything all figured out and so they judged everything and they judged everyone. And I realized that they're underestimating me. Who I was had nothing to do.
With it.
Because if they were curious, they would ask questions. You know, questions like, have you played a lot of darts, Ted?
Yeah. And that speaks to the greatest opportunity you and I have is curiosity. Believing we know the answers, believing others don't, is ultimately our trap. And can we have the courage just to be curious about everyone else and learn and find our own lessons within? There's huge strength and curiosity. Great line by Ted Lasso. Let's see if he had to get two triple twenties and a bullseye. Let's see if he does it.
Which I would have answered, yes, sir. Every Sunday afternoon at a sports bar with my father from age 10 to 16 when he passed away.
Barbecue sauce.
Good game, Ruby.
Come on, let's go.
You are a very lovely consolation prize. Rebecca, Ted, enjoy your evening, mate. As always.
That felt good. It was fun.
Yeah.
Only one thing left to do now.
What's that?
Do I have to?
What a good guy. Yeah, that's fun. So I'll tell you, winning comes from practice, right? And that's the thing he talks about the very end is every Sunday from age 10 to 16, 300 plus sessions. Is it more than that? Probably. That he has practiced darts and gave him that mastery skill? I'll tell you, that's the ultimate lesson. Never see yourself as the master. Always be curious, always be learning, always be practicing over and over and over again. It's from that you become a master and maybe win the game. Thanks for watching this episode of the Real Entrepreneur. As a reminder, any questions or comments you have, go to mikemcalowitz.com question and be sure to ring the notification bell and hit that subscribe button. And I look forward to seeing you on the next episode of the Real Entrepreneur.
