SAGEGREEN

It all started on a business trip, mid-flight.

The very first time I seriously thought about breaking up with my business partner was on our way to a major overseas project. The whole drama went down right there on the plane.

We flew out of Tokyo for a destination somewhere in Asia, about a three-hour flight. For the first two hours, I just slept and read some books and downloaded documents on my phone. But with about an hour left, we were both losing our minds out of sheer boredom. There was no in-flight Wi-Fi, so any work that required an internet connection was out of the question.

That’s when he turned to me and said, "Man, I'm bored. Let’s play 20 Questions." Who would’ve thought that a simple childhood game would almost wreck our entire partnership?

The "20 Questions Incident" That Sparked a Business Crisis.

The game started an hour before landing and lasted until we touched down. Now, you might wonder how a game could trigger a partnership crisis. First of all, his entire strategy was incredibly petty and toxic.

Quick context:20 Questions is a game where one person thinks of a secret word (a noun), and the other person tries to guess it by asking up to 20 "Yes" or "No" questions.

To be fair, playing to win isn’t the issue. The world is full of overly competitive people; I’ve dealt with plenty of them.

But to me, a game like this isn't about winning or losing. It's a casual conversation. It’s about enjoying each other’s thought process and vibe. It’s supposed to be lighthearted fun, where you go, "Oh, wow, I can't believe you thought of that!" or "That was a clever angle." It's entertainment. So, I genuinely don’t get people who try so hard to trap the other person. To me, trying to flex and assert dominance during a casual game to pass the time is just cringe. We’re adults here, entertain me with some smart banter, not some cheap, petty traps.

So, whenever I run into people like that, I always think, “Wow, how incredibly immature and uncharming.” But when someone brings that kind of aggressive energy, I have no choice but to push back a little, even though it completely ruins the vibe and turns into a miserable match.

And that’s exactly how a game between two male business partners on a plane slowly dissolved into a messy mudslinging match.

About 15 minutes in (which already felt like forever), we were both running out of ideas. When it was his turn to lead, he picked this incredibly obscure, hyper-technical jargon that no amount of questions could ever lead to. When I finally gave up and asked, "Alright, what was it?" he said something like, "Oh, it’s a super minor technical standard from the 1950s used exclusively in X industry."

The first time, whatever. But by the second and third time he pulled this "hyper-obscure knowledge you couldn’t possibly know" routine, my inner voice, which is usually pretty composed, literally screamed, “Are you freaking kidding me right now?!”

So I finally said it out loud: "Dude, come on, I don’t know that. Is it even legal to use such a niche, context-dependent word? There’s no way anyone could guess that in 20 questions."

He just replied, "Hey, the rule says any noun goes. You literally did the same thing to me earlier."

True, a few rounds back, I had used the word "Waves." Waves is an audio software company that mostly makes plug-in effects. But I chose that specifically because he used to work in the audio industry. I picked it based on the premise of, “He’s got the background, he’ll definitely get a kick out of this.”

And he actually knew it! He told me, "Wow, I can't believe you know Waves!" and I said, "Yeah, I did some market research for that industry back in the day." It was great banter, the exact way the game is supposed to be played.

And this guy thought that and his petty moves were the same thing?

We were miles up in the air with zero internet access, meaning I couldn't even Google it to verify if his words actually existed. And in that exact scenario, he decides to pull out some hyper-niche concept I couldn't possibly know?

Does that standard even exist?

Is he just making this up?

Distrust was seriously building up.

Even if it didn't exist and he was just fabricating words on the spot, he could easily get away with it in that environment.

Honestly, in a situation like that, pushing the line right to where the other person might just know it, that’s what shows good character and a big heart. Especially since we’re business partners, shouldn’t there be a baseline level of respect for each other's context? I do it for him, I thought, as resentment started to brew inside me.

Still, it was just a game. No money was on the line, and it wasn’t worth throwing a tantrum over.

So even when he threw out those weird technical terms, I’d just say, "Oh, huh, alright," take note of it, and move on to the next round. Meanwhile, I made sure to stay away from obscure words myself. Choosing a word where the other person can't even tell if it's real or fake just kills the fun of the game. I physically couldn’t bring myself to do that.

Fast forward about 45 minutes. The plane was starting its descent, and in response to one of my questions, he smirked and said, "Just give up already. You lose."

I could literally feel the cortisol, the stress hormone, flooding my system. It felt like a straight-up jet blast.

At that point, it wasn't even about winning or losing anymore. I was completely overwhelmed by this suffocating realization: “I absolutely despise how this guy operates... As a business partner, I cannot stand someone who does things this way.”

So I told him straight up, "Yeah... look, playing games with you just brings out the absolute worst parts of your personality. I don’t want to play anymore. It’s just ugly."

But even then, he still tried to force a conclusion, saying, "Wait, why? Alright, then you forfeit, so it’s my win."

"Look," I said, "it’s not that I mind losing. But your strategy is so dirty that it doesn’t even feel like a real loss. You're just throwing out random technical jargon. If you want a proper win, you should play in a way where the other person can actually accept the defeat. Everything you've been saying makes zero sense to me. I don’t even know if these words are real. Doing this over and over... honestly, it makes me question your character."

He shot back, "Why are you being like this? Just admit you lost. I just have better information processing skills and a wider vocabulary than you."

I felt dizzy wondering what his definition of "skills" even was. But expanding the argument to "what vocabulary and data processing actually mean in business" would have been total chaos. Arguing that level of philosophy with someone who defines knowledge as a tool for a power trip is completely pointless and a waste of time. So I let that slide.

But even putting that aside, that single comment had so many red flags.

I told him, "Look, I tell you all the time: you cannot say things that put people down like that. That kind of talk destroys teams. We're about to run a massive project, and if you talk like that to clients or subordinates, you will lose their trust instantly. I’ve told you to watch it if you want to be a leader. Even if you are more knowledgeable than me, what is the point of going out of your way to flex that on me?"

He just shrugged and said, "Why are you so mad? It’s just a joke."

"A joke is only a joke if the other person laughs," I replied. "Otherwise, it fails as a joke. That wasn't funny."

He doubled down: "You just hate losing to me."

"I have never once measured our relationship in terms of winning or losing," I said. "I couldn't care less who is 'above' or 'below.' Even if there are areas where I excel more than you, have I ever thrown that in your face? Have I ever said 'I'm on top, you're on the bottom'? No, because I think it’s completely irrelevant."

If I ever care about rankings or winning against my partner (or anyone else, for that matter), it’s only when there are incentives or a competitive pitch on the line, situations where if we don’t get #1, we lose the contract.

I have zero interest in winning just for the sake of pride when winning gets you nothing and losing costs you nothing. If there’s nothing to gain and no harm done, I truly don't care either way. Competing within the company or the team doesn’t get anyone a prize, so I’ve never viewed him as a rival. Aren't we supposed to be a team? Co-founders?

Aren't we supposed to lend each other our strengths, borrow where we’re lacking, and support each other to make this business thrive?

"If this were a networking event and you were just some guy sitting next to me," I told him,

"I would’ve just said, 'Wow, you got me, you're good,' quickly changed seats, and never sat near you again. Or I would’ve just left. Losing a game or having someone think I lost means nothing to me. But I would think, 'Wow, what a jerk, what a toxic personality, I want nothing to do with him, that is incredibly cringe,' and I’d walk away. I would never work with someone like that."

Hearing that, he was completely speechless.

I hammered it home: "I never want to play 20 Questions with you again for the rest of my life because it brings out nothing but your worst traits. It's not about winning or losing. When you play like that, it's boring, and it makes me dislike you. Even if someone is trying to beat me, there are people who can make it a creative, fun game for both sides. But not you. I am never playing a game with you again. If this is what it’s going to be like, I’d rather just dissolve our business partnership."

The Othello Crisis: A Decade Later

It’s been 10 years since then.

After that trip, we kept our hands off games and strictly focused on business, so games never threatened our partnership again. That is, until recently, when an Othello board was brought into the office for staff breaks. It triggered that exact same feeling of disgust and contempt from all those years ago.

I told him straight up, "I am not playing Othello with you. It makes me want to dissolve our partnership."

He laughed, "Why? Just because I'm good? You're way too competitive."

"It’s not about being competitive!" I snapped.

"I don’t mind losing at all. But playing against you is zero fun. Othello is a game where you're supposed to enjoy the suspense of not knowing who’s going to win. But you play with the entire game mapped out in your head from the start, smirking and going, 'Oh, man, lol,' 'Yikes,' 'Why would you place it there? lol.' Playing while having the 'guaranteed loss' stamp pressed onto my forehead is not fun. And saying things like, 'I'm just letting you play for now so I can sweep the board later, lol' is so freaking cringe. It is so cringe. I don’t think you’re smart; I just think you’re incredibly gross. It’s not that I hate losing, it’s that games, in general, are only fun when you play against someone at your own skill level. I have zero motivation to play a miserable game. That’s all it is, and seeing you desperately try to crush me for no reason makes you look so cringe I honestly want to quit being your partner. I'd love to play Othello with the interns or my friends, but you? Your playstyle is just too toxic. I can't do it."

The World is Full of Dealbreakers.

The truth is, there are plenty of triggers that could end a relationship.

Even though we are business partners who generally get along great, we definitely have our mismatches. There are plenty of compatibility issues that could act as a trigger to dissolve our duo. 20 Questions and Othello are just examples. As much as I respect him as a professional, there are just as many things about him that I dislike, or find completely unbearable and cringe.

To give you a pretty fatal example: our casual, day-to-day conversation is completely incompatible. No matter the topic, whenever he responds, I always end up thinking, “Wow, this guy’s mindset is so low-tier... His understanding of this issue is so superficial it's hopeless... Wow, his take on this is so petty and trashy.” Because of that, I take meticulous care to make sure we never get into deep personal conversations. He is quite literally the last person on earth I would ever go to for personal advice.

But that’s exactly why I realized something.

Even if you don’t match well in many areas, you can get along perfectly fine as long as you don't force yourselves to share those unaligned spaces. If you don't try to do absolutely everything with your business partner, if you don't look to them to fulfill your entire life and emotional needs, you can build a relationship that bypasses those triggers completely, keeping them from ever becoming a problem.

Outside of core business operations, there really isn't much you have to share with your partner. If your compatibility is terrible in a certain area, you can always look to other people, friends, family, or other acquaintances, to fulfill that specific need.

I don’t love everything about my partner. In fact, I dislike a lot of things about him.

But if avoiding those traits simply means never doing certain activities together again, then the solution is easy: just don't do them. What a long-term business life requires isn't patience, compromise, or just drifting along on inertia; it's this kind of conscious boundary-setting and traffic control.

My stance is basically: "Look, I hate this specific side of you. So let's never do this together again. It's too cringe for me to handle, and if I get exposed to too much of it, it makes me want to quit this partnership."

We don’t even need to fully understand each other. Honestly, if we sat down and faced each other raw, there are more parts of us that clash than align.

But regardless of whether we vibe on a personal level, he possesses an overwhelming drive and charisma that blows business wide open. And that is why, for 10 years straight, I have continuously chosen to climb to the top with this man.

The Next Day: "Hey, Play 20 Questions with Me!"

Now, that mid-flight incident actually has a sequel.

On our second night after arriving at our destination, out of nowhere, he invited me to play 20 Questions again. He literally came up to me all excited, shouting, "Let’s play one more time!"

Naturally, I shut him down: "No way! I told you I am never playing a game with you again for the rest of my life. It brings out nothing but your worst traits."

But he wouldn't let it go, begging me: "Come on, please! Don't be like that! This time will be fine, I swear! I’ll only pick categories you definitely know! I won’t say anything mean! Please, just give me one more chance!"

I was wondering what kind of grown-man begging routine I was witnessing, but I reluctantly gave in. And true to his word, he didn't throw out any weird, hyper-niche jargon, nor did he let his toxic side show. Instead, he chose these perfectly hilarious words and gave clues in a way that completely overwrote that miserable flight experience. His communication made me think, “Yeah, this is why I partnered up with this guy after all.” He completely redeemed himself. I don't remember the exact words he used (because let’s face it, our brains are wired to remember the bad stuff vivid clear!), but it worked.

That said, that game was a massive effort on his part to reach out and close the gap. Letting our guard down and playing games casually is still way too risky, so ever since that trip, games between the two of us have been permanently banned.

Even two people who respect each other enough to build a business together won't have perfect compatibility across the board. There will always be just as many, if not more, areas where you completely clash.

Life is all about the right person in the right place. Instead of blindly trying to share everything just because "we're partners," intentionally choosing what not to do together to "keep the team at its absolute strongest" is a necessary part of healthy business operations. And honestly, I think that represents a deeply powerful level of trust and respect.

—

The beat below was inspired by this exact experience. I’d love for you to give it a listen.

SAGEGREEN - Mash Melon

https://open.spotify.com/track/1TxQjCe14aGieP2xretcUs?si=jw4QqfC5RiOq86zNREEpkA

My new beat tape out now! And the vlog.

SAGEGREEN - Wipeout Beat Tape

https://open.spotify.com/album/3yvUIlUA6JMvEEyZtSxbf3?si=gbeu-2SlTm-e2Mq5PS1VMw

Hope y’all enjoy it. Have a nice one!

—