Ep 649 | Difficult Is Good: Don Valentine’s 4 Quadrants

Thank you for joining me today. It's Brian Gubernick, and welcome to the No Days Off podcast, where we believe that every single day brings a new opportunity to get better. Don Valentine, the founder of Sequoia Capital, had one of the sharpest filters when it came to evaluating businesses, and more specifically, when it came to evaluating entrepreneurs. Sequoia Capital is, is legendary for its investment in, in various startups. It's one at a massive level. And Don Valentine, who, who founded Sequoia, he was, you know, he was quite, quite, uh, the driver of that. Don would map founders out across really kind of two axis— two axes. Uh, first he had the easy to get along with versus the hard to get along with. So when you think about a founder of a company, they were easy to get along with or hard to get along with. He chart that out, and then he would compare it against they were normal versus they were brilliant. Now you might think the dream scenario, if you picture this as 4 quadrants, you might think the dream scenario is to be working with those that fall in the brilliant and easy to work with quadrant. But Don Valentine didn't see it that way. He actually believed the best investments were often in people who were brilliant, yes, but also difficult. And that insight, I think, has huge implications for how we show up as entrepreneurs and how we operate our respective businesses. So as I mentioned, Valentine invested in brilliance, no question about it, even if it came packaged though with a really tough personality. Why did he do this? Well, he did it because brilliance without friction oftentimes did not push the boundaries far enough. Disruptive companies, which is who Sequoia is looking for, really disruptive companies that are gonna, gonna, that are gonna change business, change the world, these types of companies usually come from people who are obsessive, who are uncompromising. They're even abrasive at times. But I think here's the key. That doesn't mean that you now should try to be hard to get along with. I mean, hey, some of you probably are very hard to get along with, but it doesn't mean if you're not that guy or girl right now, it doesn't mean go try to be hard to get along with. I think the takeaway is a little bit different. It's lean into your edge. Lean into your conviction, lean into your refusal to settle, and do that while learning to manage how that intensity lands on others. So let's, let's break these 4 quadrants down a little bit deeper. So you have the normal level of intelligence, right? Normal versus brilliant. So you had normal and easy to get along with. These are very likable individuals, but they're also rather average. So they're nice to be around, but they're not game-changing. And so Sequoia and Valentine had no interest in these types of founders because the safe wasn't going to transform industries. You then have the next quadrant, which is normal in terms of intelligence and hard to get along with. So these individuals are both difficult and ordinary. It's— bottom line, it's the worst quadrant because it's all the friction and none of the upside. So in business terms, you're burning bridges without adding unique value. It goes without saying Sequoia did not mess with this quadrant. Quadrant 3 though is where you start working with the brilliant individuals. So not normal level of intelligence, but brilliant, but they're easy to get along with. Now this may sound ideal, but for Valentine, he often found these people were not, not disruptive enough or willing to be disruptive enough. So they might make for great operators, but they were not necessarily visionaries who would bend reality. Sometimes, at least from Valentine's perspective, sometimes when you're easy to get along with, it might mean you compromise too soon. And then that fourth quadrant, that's the brilliant individual who's also hard to get along with. This is the quadrant that Sequoia bet on. Brilliance paired with stubbornness, part, you know, paired with this willingness to push through resistance, this contrarianism. When you pair brilliance with those things, Valentine thought it was worth the bet. So yes, these individuals can be abrasive, but they also refuse to quit. They refuse to blend in. And that's what created category-defining companies. So how do you apply this? As a member of the No Days Off Nation, you're likely an entrepreneur. How do you apply this stuff in your world? I think first, don't stand down. Don't, you know, give in if you're convicted. If you have conviction, your job isn't to be universally liked. It's to build something extraordinary. So if your vision creates friction, that's oftentimes a sign you're onto something. Next, separate being hard from being toxic. There's a very big difference between those two. Valentine and Sequoia backed difficult people, but they weren't destructive. They were relentless about the mission. So the lesson, I think, is be firm but not cruel. Be convicted but not careless. Number 3, I think, in terms of application for entrepreneurs: channel the energy. If you're brilliant and hard to deal with, learn to direct your intensity at the problem, not the people. Your team will tolerate difficult if they believe in your mission and see your, you know, see that your sharpness makes the company better. I think about Elon when you talk around this particular application. He's brilliant. He's hard to deal with. He's intense. I think he does a good job channeling that intensity at the problem. And so, his team's willing to tolerate it. Because they believe in the mission. Lastly, build bridges around your edges. What do I mean? What I mean is some entrepreneurs need a partner or an operator who smooths out their rough spots. Steve Jobs had Wozniak. You know, Gates had Ballmer. So, recognize if maybe you need that counterweight. So, the tactical takeaways for you today. Ask yourself, am I pushing boundaries or am I defaulting to safe and likable? I think it's a really good question. And then I think you ought to really truly clarify your mission. Conviction without clarity looks, you know, can look just like arrogance. So, write down the hill you're willing to die on. And then lastly, be sure you're checking for collateral damage. What do I mean when I say that? Are you burning out talent? Are you burning out your people unnecessarily? Remember, difficult should drive progress. It should not drive destruction. And you know, since I mentioned it, one more thing for you. Maybe you need a counterbalance. If you know you're a pain in the butt, if you know you're high friction, pair with someone who balances culture and relationships. You know, I think that Don Valentine, you know, what he said, you know, here is, is he said difficult is, is a good thing. And for entrepreneur— entrepreneurs, for some of you, that should be pretty liberating. You don't have to be universally liked. You don't have to smooth off every edge. Your conviction, your intensity, that may be the very thing that changes the game. But I do want you to hear this: difficult is not a license to be toxic. It's an invitation to stand firm. It's an invitation to refuse compromise. It's an invitation to keep your brilliance sharp. The world, as we all know, does not reward good. It does not reward average. It rewards brilliance, even if it makes people uncomfortable along the way. That's all I have for you today, the No Days Off Podcast. Thank you so much for listening, and remember, every single day brings a new opportunity to get better. So let's get after it.