How to Close Clients as the Underdog w/ Chris Do | Ep 439

Summary

Podcast Summary: The Futur with Chris Do

Episode 439: How to Close Clients as the Underdog w/ Chris Do
Date: June 24, 2026

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Episode Overview

Chris Do dissects a pivotal negotiation scene from the film Air—which dramatizes Nike's legendary signing of Michael Jordan—to extract lessons for closing deals as the underdog. Drawing parallels to design, business pitches, and his own real-world experiences, Chris reveals how leveraging an opponent’s perceived strengths against them, planting seeds of doubt, and knowing your unique value can turn the tables, even when the odds seem stacked. The episode spotlights negotiation psychology, story-driven persuasion, and how innovation often comes from fresh perspectives.

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Key Discussion Points & Insights

1. The Underdog’s Playbook: Flipping the Script

• Context: Nike, in 1984, was an underdog brand trying to sign a relatively unknown rookie, Michael Jordan, against giants like Adidas and Converse (00:00).
• Strategic Move: The Nike talent scout (played by Matt Damon in Air) gets Michael Jordan’s mom to ask their competitors tough, revealing questions to expose their weaknesses rather than focus on their strengths.
  • Quote:
    “The best thing you can do is think about their greatest weakness and exploit that and have your potential client focus all their energies on your competitors weaknesses rather than their strengths.”
    —Narrator (00:44)
• Psychological Warfare: Seed doubt by predicting competitors’ pitches and encouraging the client to scrutinize the sameness or lack of vision in those offers (01:10–01:50).

2. Tactics from the Nike–Jordan Negotiation

• Converse Pitch Weakness

  • Scripted, cliche pitch: Predictable, formulaic (describes their attire and approach).
  • Unique Value Prompt:
    “How's Michael going to stand out from these other players? How's he going to be different?”
    —Matt Damon, as Talent Scout (01:50)
  • Narrative Impact: Making Jordan’s mom feel her son would just be “number four” at Converse, not a true star (03:05).
    • Quote:
      “The best Michael will ever be with you is number four.”
      —Michael Jordan’s Mom (03:05)

• Adidas Pitch Weakness

  • Cool factor, but lack of unified leadership; family business controlled by multiple heads.
  • Targeted Question:
    “Who’s running your company?”
    —Matt Damon, as Talent Scout (04:09)

• Nike’s Differentiating Approach

  • Anticipating the need to answer tough questions themselves.
    • Quote:
      “Ask me why I'm in Wilmington, North Carolina.”
      —Matt Damon, as Talent Scout (06:32)
  • Heartfelt Response:
    “Because I believe in your son. I believe he's different, and I believe you might be the only person on earth who knows it.”
    —Matt Damon, as Talent Scout (07:06)

• Insight:
  Pay special attention to who actually makes decisions (the “real” decision maker is not always obvious—here, it’s Jordan’s mother).

3. Real-World Application

• Chris Do’s Story:
  Chris recounts coaching a friend (Carrie) who kept losing deals to a cheaper competitor. He advised her to ask the client to challenge the competitor with harder, more specific project questions and to explain upfront why her prices are higher.
  • Memorable Point:
    “Ask them to show you examples and for you to feel confident that they can do this work for you... She did exactly this... They signed for the amount that was twice as much as what the other person was offering because that person could not answer those basic questions.”
    —Chris Do (09:30)
• Lesson:
  Frame the conversation so that price is not a surprise, anchor expectations, and force competitors to prove real capability.

4. Game-Changing Negotiation: The Royalty Clause

• Turning Point:
  Jordan’s mother negotiates a revenue share for each shoe sold with Michael’s name—a massive industry innovation (10:59).

• Notable Quotes:

  • “Michael will get a percentage of the revenue of the sale of each shoe that is sold... just the ones with his name on them.”
    —Michael Jordan’s Mom (10:59)
  • “That would disrupt the industry... There’s a whole other set of economics around this.”
    —Matt Damon, as Talent Scout (11:12)
  • “It’s unfair to people like you. But every once in a while, someone comes along that’s so extraordinary... they understand what they are worth.”
    —Michael Jordan’s Mom (12:07)

• Innovation Insight:
  Outsiders and industry newcomers drive innovation because they aren’t “bought into the doctrine or dogma of how things are done” (12:54).

5. The Power of Focus and Betting Big

• Nike’s Risk:
  Gave the entire annual basketball endorsement budget to Michael Jordan alone—a high-risk, high-reward move.
  • Stats: $2.5M contract (5 years at $500K/year), 5% royalty, more than 3x what had ever been paid (13:25).
  • Outcome: $100M+ in sales in year one, $1.3B+ total for Jordan over decades.
  • Quote:
    “By agreeing to do this one deal, they also pay Michael Jordan, first time ever it’s happened, 5% royalty in stocks and commissions on his shoes... To this day...sells four times more in terms of revenue in shoes than LeBron James.”
    —Chris Do (14:15)

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Notable Quotes & Memorable Moments

• “So if you take that half a million dollars and you give 50,000 here and there, you can have 10 athletes that are all going to be mediocre. But there’s only one Michael Jordan.” —Chris Do (13:40)
• “Innovation comes from someone fairly new in an industry...with the boldness to think differently. Not because she’s a bold person per se, but because she doesn’t know how things are done.” —Chris Do (12:54)
• “You eat, we eat. That’s all he’s asking.” —Michael Jordan’s Mom (12:07)

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Important Timestamps

• 00:00–01:10: Introduction to the underdog negotiation concept (Michael Jordan–Nike story setup)
• 01:10–03:21: Breaking down the negotiation with Converse; using questions to expose flaws
• 04:00–06:05: Handling Adidas, pointing out leadership confusion
• 06:30–07:21: Preparing for and answering the “why should we pick you?” question
• 09:10–10:59: Chris Do’s real-life client pitch story
• 10:59–12:54: The revolutionary royalty clause negotiation with Michael Jordan’s mother
• 13:25–14:15: The business impact—biggest endorsement deal, singular focus, staggering results

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Takeaways for Listeners

• Pitch as the underdog by strategically prompting clients to see competitors’ weaknesses.
• Plant questions that disrupt your competitor’s narrative, and prepare your own slam-dunk answers.
• Anchor value by being transparent about costs and what makes your offer unique.
• Identify and focus on the true decision maker in any negotiation.
• Innovation often comes from those unafraid to challenge conventions.
• Sometimes, betting all-in on the right opportunity multiplies results exponentially.

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This episode is a masterclass in negotiation strategy, using pop culture storytelling and real business experience to arm listeners with practical, psychological tools for winning against the odds.

Transcript

[Narrator]

Have you ever found yourself in a pitch situation where you're the underdog, where you don't think you have any chance of winning it? Well, you need to watch this clip because I'm going to break down air the untold Michael Jordan story about how Nike got Michael Jordan to sign and become the biggest athlete of all time. The lessons that you can learn from watching these clips. But stick around to the very end because there's a clip that most people miss that's even more revolutionary, more profound than the first one. For context, the year is 1984. Michael Jordan is still a relatively unknown person. He's still rookie, hasn't played in the NBA. And Matt Damon's character is a talent scout working for Phil Knight of the legendary Nike. And he wants to bet the entire fortune of the company on signing Michael Jordan as a featured athlete. He has to negotiate with Michael Jordan's mom. If you find yourself in a position where you're going to go up against bigger players, people who have bigger team, more experience, better quality of work, you don't really stand much of a chance unless you can cast some doubt, drop from the client side and the best thing you can do is think about their greatest weakness and exploit that and have your potential client focus all their energies on your competitors weaknesses rather than their strengths. Watch how he flips it around.

[Michael Jordan's Mom]

Come on back, take a seat, Mr. Vaccaro. Now you do understand that Michael's intention is to sign with Adidas with convers as a second option?

[Matt Damon (Talent Scout)]

I do. And with respect, I think that's a mistake. I, I'll make a bet with you. I, I'll tell you exactly how those meetings are going to go. If I'm wrong, then then don't take a meeting with Nike. But if I'm right, please consider that, that you and Michael come out.

[Narrator]

He's offering non deal, right? If you think about it, they're not even interested in taking a meeting with Nike at this point. You don't need to meet with us if everyone else is cool. Only meet with us if they both suck. And so this is the beginning of the psychological operation. He's doing a psyop.

[Matt Damon (Talent Scout)]

This is converse, by the way. John o' Neill will have his hair gelled up. A bunch of them will be wearing red ties for the Bulls. John will have a Rolex for sure. Now I've seen a lot of basketball, but the feeling that I get when I see Michael, there's only a few other players who gave me that feeling. Now when he's done I'd love it if you would ask him a question. How's Michael going to stand out from these other players? How's he going to be different?

[Narrator]

So here he's going for a low blow. He tells them how they're going to dress, and it's almost predictable and laughable. And if this were to play out to be true, it almost seems like they're very cookie cutter and formulaic. And the last thing a mom wants for her son is to feel as if she's just part of an assembly line.

[Matt Damon (Talent Scout)]

The feeling I get when I see Michael play. There are only a few other players that gave me that feeling. And those players are here at Converse. It is that simple. Michael, we're going to treat you like our superstars before you even set foot on an NBA court. We're looking for a shoe that holds appeal beyond the basketball court. Well, what could hold more appeal than the shoe worn by the best players in the game? Tradition and history are paramount.

[Michael Jordan's Mom]

At Commerce, you have an impressive roster. Best three players in the league in Magic Johnson, Larry Bird, Julius Irving. But another way of looking at this is that the best Michael will ever be with you is number four.

[Matt Damon (Talent Scout)]

Frankly, ma', am, we're, we're talking about Magic Johnson and, and Larry Bird here. He's gonna play like them. He's gonna be mentioned in the same sentence with them.

[Narrator]

What can be better than that? And they know they have the biggest athletes, the three biggest basketball players of the time, and they think that's a strength. And so he uses the strength against them and teaches her how to ask the question. So he tells her to ask them, how is Michael going to stand out? And it's going to catch them flat footed. They're not going to expect that. So they won't know how to respond. It's going to make them look embarrassed. And so he's helping to create a friction point here that he's just one of many.

[Michael Jordan's Mom]

What about Michael's meeting with Adidas? Michael's top choice is Adidas.

[Narrator]

Hello, Mrs. Jordan.

[Michael Jordan's Mom]

Welcome.

[Narrator]

You could just tell me.

[Michael Jordan's Mom]

Okay, sorry.

[Matt Damon (Talent Scout)]

Here's what they'll say. We have the best shoes, plain and simple. All leather. All the kids want to wear them. They're not wrong. I get why Michael wants to go there. Here's what you should ask them. Who's running your company? I think four different people in that room are going to give you four different answers. And that's the problem at Adidas right now. And it's going to be a real headache for you. For the next few years.

[Narrator]

So now he has to take on the Big Dog. Which is Michael's favorite is Adidas, which is hip with the kids, I think mostly due to run DMC and hip hop culture, embracing Adidas as a cool brand. So of course Michael wants to be cool. He wants to be of the culture. There aren't many areas in which they're weak. They have the cool factor and they make all leather shoes, so they'll have superior shoe craftsmanship. The two things you can point out are the cultural difference between a German company. You're an American, I'm an American. These are Germans. Maybe they don't understand us the way we understand each other. So there's that cultural divide that they might experience there and the fact that they're run by a board. There's four people who have a stake in the game. Four opinions. They don't agree. Four heads are not greater than one. So his question for us to ask them. So who's really running this? And this will exploit their weaknesses to

[Matt Damon (Talent Scout)]

welcome you in Germany and also thank you for making the excruciatingly long journey to come and see us.

[Michael Jordan's Mom]

Yes, thank you.

[Matt Damon (Talent Scout)]

Michael, you're the next generation. You don't want to be grouped in with Magic and Bird. You belong in our stable of athletes.

[Narrator]

And I know this is a family

[Michael Jordan's Mom]

business, but who makes the final decision?

[Matt Damon (Talent Scout)]

Well, unfortunately, the family has suffered a tremendous loss. Keita is calling the shots now.

[Michael Jordan's Mom]

Yes, that's right.

[Matt Damon (Talent Scout)]

It is collaborative.

[Michael Jordan's Mom]

So. Decision.

[Narrator]

Okay, so you can see there. So that when she's there, she's going to be extremely sensitive and observant to the fact the four of them are not always speaking the same language. And he's saying, it's going to be a headache for you. So now he's done everything he needs to do to create enough friction and. And pause reservation as to why these two frontliners are no longer the choice. So he has to be ready for the next part, which is this.

[Michael Jordan's Mom]

What should I ask you?

[Matt Damon (Talent Scout)]

Ask me why I'm in Wilmington, North Carolina.

[Narrator]

I gotta pause here. So then she's like, okay, you're so smart, Matt Damon. What question should I ask you? And then, of course, he's ready to answer this question. Because if he sets up this thing where he's a asked the two companies this question, naturally, he better figure out what question she's going to ask him and be able to respond. And the way he teaches her to ask this question is quite brilliant because he's setting himself up to do A slam dunk.

[Michael Jordan's Mom]

Why are you in Wilmington, North Carolina?

[Matt Damon (Talent Scout)]

Because I believe in your son. I believe he's different, and I believe you might be the only person on earth who knows it. That's why I'm in Wilmington, North Carolina.

[Narrator]

Naturally, if you're going to create a lot of doubt and give your prospective client questions to ask each competitor, you have to be prepared that they're going to ask you, well, why? What should I be asking you? How are you weak? When she asked that question, she's fallen squarely into his trap because he set it up for this. So in a weird way, he's paying homage to the mom, which is very important because he's identified her as a decision maker. Notice the father's not in the story at all. It's all about the mom. And so when you're in a room full of decision makers, try to isolate who really has the power. And you need to make sure not only do you hear everybody, but you pay careful attention to the one that's going to make the decision. So he plays right into her. And it's like, I believe you can see things that no one else can see, but I also see that as well.

[Michael Jordan's Mom]

Right? Pastor Picaro, thank you for coming.

[Matt Damon (Talent Scout)]

Thank you.

[Narrator]

And that's how you win over somebody when you're the underdog. I'll tell you a real story. There's a friend of mine, her name is Carrie, and she called me one day, frustrated with life. I said, hey, what's wrong? She goes, you know what? I am tired of losing pitches to this girl. There's a girl who does what I do, says what I say, and she's doing it for less than half of what I'm charging. So every time I get on a call with a client, I'll mention my price, and, like, it's too much, and I just lose the client. Time and time again, I say, well, Carrie, this happens to you once, that's. That sucks. But if it happens you more than once from the same person, whose fault is it really? You've not adequately addressed what's happening. So I said, here's what you want to do. And I asked her some questions. Does this person deliver on the work that you can do? She goes, no, she doesn't. She uses the language so it can fool clients. I said, well, what kind of questions would you ask the client to prove to them that you know what you're talking about versus them? Okay, so she didn't have an answer to this. So here's the exact thing I Told her, as best as my memory can recall, you can start the conversation like this. Well, out of curiosity, I know you have lots of options to consider. What call am I for you today in terms of who you're considering? And if I'm not the last person, I would prefer to be last. And the reason why I say this is because I'm going to give you a price. It's going to be twice as much as somebody else is going to say. And I don't want to start there, but I would love for you to ask whoever you're talking to this one question. When they tell you they can do branding, design and strategy, ask them to show you examples and for you to feel confident that they can do this work for you. Because lots of people say things, but they can't back them up. And so she did exactly this. A couple days later, Care calls me back. He goes, kris, I said everything you told me to say. And guess what? They called me back. They signed for the amount that was twice as much as what the other person was offering because that person could not answer those basic questions. So this is a real life example that very closely mirrors what you're seeing in Air, in that she's giving them tough questions to ask of her competitors. And if they can't sufficiently answer it, she says, call me last, but don't call me if you get a good answer, because you don't need to. Why? Because that'll be twice as much. So we're doing a lot of things here. We're casting doubt legitimately. So, by the way, it's not just throwing shade because people say things that they can't back up with real evidence. But number two, she's planting the seed that she's going to be twice as much so that when she says the price this time, they have no excuse to say, wow, Carrie, that was a lot of money. Because she could say, I told you it was a lot of money. This is a great way to prime your prospective buyer so that they don't see price as a barrier anymore and they see it as just a cost of doing business. All right, promise you at the beginning, you need to stick around for the second clip because I think this is master for negotiations that has changed the game moving forward for everyone in the sports market. All right, let's check it out.

[Michael Jordan's Mom]

Michael will get a percentage of the revenue of the sale of each shoe that is sold. I'm sorry, not all Nike shoes, just the ones with this name on them.

[Matt Damon (Talent Scout)]

Oh, Mrs. Jordan.

[Narrator]

So that's not how the business works at all.

[Matt Damon (Talent Scout)]

I mean, I. I understand the assumption, but that would disrupt the industry and they wouldn't pay. There's a. There's a whole other set of economics around this. It's very complicated here.

[Michael Jordan's Mom]

Well, that's not his concern. His concern is that in order for the shoe to be meaningful, in order for young people, many not have real means to want to go out and spend the money that they've worked all week, two weeks at the mall for. Then Michael has to create demeaning in that shoe. His name is on that shoe.

[Matt Damon (Talent Scout)]

Yeah, so actually, we think that's a benefit to him because his likeness gets marketed by Nike.

[Michael Jordan's Mom]

No, his likeness, his name is not in any way meaningful to Nike unless he scores 40 points a night, every night, beats Akeem as rookie of the year, makes all star and all NBA team.

[Matt Damon (Talent Scout)]

You know, it is the NBA. So these are the best of the best.

[Michael Jordan's Mom]

Well, he has to be better.

[Matt Damon (Talent Scout)]

You don't get to be Magic and Michael Cooper.

[Narrator]

It's basketball.

[Michael Jordan's Mom]

But if he does it, he deserves to be compensated. You eat, we eat. That's all he's asking. It's unfair to my son. It's unfair to people like you. But every once in a while, someone comes along that's so extraordinary that it forces those reluctant to part with some of that wealth to do so. Not out of charity, but out of greed. Because they are so very special. And even more rare. That person demands to be treated according to their worth because they understand what they are worth. Is it me who believes in Michael his name? Or am I just a healthy reflection of who he is and what he believes about himself? Hmm? Isn't that why he came to my home?

[Narrator]

I love this stuff so much. I. I think we'd all be blessed if we had a tough black mom who negotiated on our behalf, who believed 100% in US and was taking no guff from any person. This is where most innovations come from. Somebody who is fairly new in an industry, who isn't bought into the doctrine or dogma of how things are done, or someone who's completely an amateur and knows nothing about this. That's where the innovation comes from. Because she has the boldness to think differently. Not because she's a bold person per se, but because she doesn't know how things are done. Ultimately, he relents because she's persistent and she's not taking no for an answer, which is beautiful. It's the richest deal that any sports company's ever made. And at the Same time, it's the cheapest deal they've ever made in terms of what they've gotten. So let me give you some stats. I look this up. So they agreed to a deal that would pay Michael Jordan $500,000 a year for five years. So that's $2.5 million contract. It's more than what they paid any other athlete from any other company. By 3x, they took their entire marketing budget for all basketball athlete endorsements and just gave it all to Michael. That's also a pretty revolutionary idea. I love this strategy so much because a lot of us commit this mistake rather than concentrating our effort into one thing. One niche, one offer, one problem we solve, one promotion. We have so many different offers to so many different avatars that we dilute our power, right? So if you take that half a million dollars and you give 50,000 here and there, you can have 10 athletes that are all going to be mediocre. But there's only one Michael Jordan. By agreeing to do this one deal, they also pay Michael Jordan, first time ever it's happened, 5% royalty in stocks and commissions on his shoes. And she clearly states in the video, it's not for all of Nike. It's just for the ones with my son's name on it, the Jordans. And they had anticipated in the first year they would sell 3 million shoes. And in fact, they sold over $100 million worth of shoes. So if he makes 5% of that, that's a big number. So not only is he paid the most and he's taken up the entire Nike budget for basketball, he's also got a piece of the business. And to date, Forbes magazine has estimated Michael Jordan's endorsement deal with Nike has garnered him over $1.3 billion. And he changed the game forever. To this day, having retired from basketball, sells four times more in terms of revenue in shoes than LeBron James does. That's staggering to me. As great as King James is, he's doing one quarter of the sales in terms of revenue than Michael Jordan is. Let me know in the comments who you believe is the greatest basketball player of all time. Is it Michael Jordan or LeBron James? If you enjoyed this series and you want us to do more like this, I enjoy making them. Let us know what show, season and episode that you think is quite brilliant. Because quite honestly, we have limited resources. We can't go through every show. And it's really down to the minute. If you say this clip, in fact, send us the clip. We'll watch it.

[Matt Damon (Talent Scout)]

Thanks.

[Narrator]

Very much, everybody. See you next time.