Ray Green answers a thought-provoking question from a friend: Is there a real difference between "play to win" and "play to not lose" people, and can you build an entire team of aggressive risk-takers? In this episode, Ray breaks down why he believes there are two distinct types of "play to not lose" people - Type 1 who are well-intentioned and think through proper risk mitigation, and Type 2 who operate from fear and lack of confidence. He explains why Type 1 people are actually assets who balance out aggressive play-to-win leaders, while Type 2 people are toxic liabilities that drain your organization. Ray shares a personal story from his first CEO role about constantly fighting with his co-founder, who drove him crazy but ultimately made him a better leader by having the confidence to speak truth to power. This is about understanding the balance you need on your team, knowing the difference between healthy defensive thinking and toxic negativity, and why you don't want a team of only one type of person.

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Welcome to Repeatable Revenue, hosted by strategic growth advisor , Ray J. Green.

About Ray:

→ Former Managing Director of National Small & Midsize Business at the U.S. Chamber of Commerce, where he doubled revenue per sale in fundraising, led the first increase in SMB membership, co-built a national Mid-Market sales channel, and more.

→ Former CEO operator for several investor groups where he led turnarounds of recently acquired small businesses.

→ Current founder of MSP Sales Partners, where we currently help IT companies scale sales: www.MSPSalesPartners.com

→ Current Sales & Sales Management Expert in Residence at the world’s largest IT business mastermind.

→ Current Managing Partner of Repeatable Revenue Ventures, where we scale B2B companies we have equity in: www.RayJGreen.com

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A friend of mine asked me a really good question yesterday that I wanted to share with you, and I gave it some thought and this is basically my answer. It is, do you think that there's a difference between play to win people and play to not lose people? Do you think you can have an entire team that is comprised of play to win people?

The context he was asking it in was he said, you know, because we do some work together, so I see you make moves in your business even when things are okay or like even when things are good, you will place some bets, whether it's with personnel, strategic decisions, like with, you know, offers and things that you're doing. Other people that he works with, he said, I feel like it's got to be on fire, like burning down for them to make any moves. And they don't take any risks. It feels overly defensive. That's where the question was coming from.

And I gave it thought. I said, you know, I do think that there is a difference in mindsets and, you know, probably personalities of play to win and play to not lose. And so the way that I will define it is like play to win, you've got people who are probably more aggressive, higher tolerance for risk, higher propensity for speed and velocity in an organization. And, you know, they're the ones that are like go, go, go, go. Like they are on the football field in the football world. They are the head coach in the NFL that says, go for it on fourth and one. Like you just know they're going to go for it. Doesn't matter where they're at in the field, doesn't matter how they've been playing like this before. I don't know analytics. Like you don't know they're the coaches that are going to go. Like there's no question they're going to stay on the field.

And then you have coaches that would say no. Like they're going to always take the guaranteed three and they're going to always play the field position game. And that's, you know, that's more of like the play to not lose. So like play to not lose, and this is the important distinction. I think there's two types.

Type one. You have a play to not lose person that is still aligned with the same goal, still well-intentioned. They understand the risk. Like they think about it through the risk lens. They're just like, hey, let's make some calculated decisions. Fourth and one, okay, maybe go for it, but why don't we look at this? Like, what does the analytics say? What does the field position look like? How have we been playing today? Like let's be, you know, a little bit more like not just go for it. Like let's roll. They're well-intentioned play to not lose mentality is born from proper, maybe slightly more defensive, but like proper risk mitigation. And they speak up about it out of confidence.

Type two people are people who just like that's just who they are, right? Like they are just the person that's always saying, I can't do that. Like they're just the first thing that like it's born out of self-esteem, right? It's born out of a lack of confidence in themselves. And when they tell you we can't do that, it's not because they firmly believe that we should still accomplish the goal, but there's a better, less risky way of achieving it. It's because they're just that person. Like they don't have enough confidence in themselves to do it. They don't have enough confidence in themselves to recover if they do and it doesn't work. And so they just like kind of like Eeyore. No, we can't do that. And they aren't speaking up about it because they're confident and willing to like speak truth to power with like leadership. They're speaking about it because they're just like toxic, like Negative Nancy. Like, okay, thanks. Like always play it safe.

So I do think that there's a difference. So which ties in like the second part of the question, which is do you think you can stack the deck only with play to win people? And what I would say is I think really early on, like as a startup, there's probably some benefit to it, right? Like if you just have if the handful of you getting going are all just like hard charging, have a high tolerance for risk, willing to push, make those bets that others wouldn't make, probably going to be an advantage.

As time goes on, but if you don't balance that at some point, I believe what happens is you end up culturally developing something that becomes more toxic in its own way. Right? Like think like to me this is like Uber, you know, as an organization when they had the cultural shift or companies like that. I feel like those are organizations that didn't have the proper balance. They didn't temper the strength that is play to win with a type one play to not lose person.

And I personally, like as a CEO, you know, my first CEO role, I hired my colleague who was my friend. We managed to remain friends, but I swear to God, we fought like cats and dogs. Like we fought all the time. Like it was, my wife always laughs about it now because there are parts of our arguments that are like been embedded in me. She'd be like, hey, we need a process, right? Like, I understand you want to move this really, really quickly. We've got to put a process in place. And I'd be like, fuck that, man. Like, we got to go. We got to go right now. Like this. I want to run. I want to sprint.

But it enabled me to be a stronger play to win person. Like I could push. Like I could lean in to my core. Right? Like that's what I wanted to do because I trusted my COO to be well-intentioned. Right? I never thought he was like, oh, dude, you're stuck. Don't be scared. Don't be a pansy. Like, come on, man. Like I was never that. It was always like I understood that his thought process was just different. And I trusted his intentions. And I knew that if I could push harder, that he would, he had the confidence to speak up and speak truth to power and tell me what he thought and put the brakes on things that needed to have the brakes put on them.

So we were like a great team. And the organization benefited as a result of that relationship that we had, even though at the time it annoyed the living shit out of me because I was like, I hired him for a reason, and he was really fucking good at his job. And which is funny now because there are things that I say about like processes and shit that I'm like, man, and that his name was Ray too. I was like, this is what Ray would talk about.

So I do think there's balance, but you don't want like they are assets, type one play to not lose are assets in your organization. Absolutely. But play to not lose type two people are huge liabilities to me. You don't want them in your organization at any level. And they may fly under the radar for a period of time. Or you may know that they exist and they're just not like on the radar just yet.

But you think about like they're the ones that are, because they're not the ones that are still aligned with the mission necessarily. They aren't the ones that are pushing, you know, just in a different way. Like they're being aggressive, but just in their own way. Their thought process is just different. Like they're just, they don't, like they don't have the confidence. They don't have the self-esteem. They don't invest in themselves. They don't, it's not a decision making process to them. It's just who they are. And it's born out of fear.

And it's not even always what they do, even though when they speak up, it's like more toxicity, right? It's like bitching and complaining for bitching and complaining sake. And it's habitual and it's just a knee jerk reaction. It's just like they're the, if they won the lottery, they'd bitch about paying taxes. Like that person, right? Born out of fear and out of everything else. Like they're not investing in themselves. They're not bought into the organization and doing the stuff that needs to get done behind the scenes.

And I think the opportunity cost of having people like that in the organization is huge. And then just the cultural effect of having that level of like negativity for negativity sake is not good.

So that's how I would categorize that. But it was an interesting thought experiment. So this is me freestyling in front of the gym on this like very quickly. So I would love your feedback. I know this is not the definitive definition of what these are. If you have some feedback, I'd love to hear it. If you have any questions, drop them in the comments below. If this has been helpful, go ahead and subscribe to the channel. Appreciate it. We've got email links and everything below if you want to join the newsletter, but see you in the next video. Adios.