What the Early Days of the “PayPal Mafia” Reveal About Tough Leadership The tech company's ascent to power offers a masterclass in leading through radical honesty and fearless debate. Matt Hunter • August 12, 2025 In my last post, I talked about the importance of honest feedback and passionate debate in getting to the truth in business. I think of this style of leading as “truth-driven leadership”: building a culture where hard truths are spoken openly, and where debate and disagreement are...
11 days ago • 4 min read
Great leaders know how to get to the truth If you want to win, start by getting honest. Matt Hunter • July 29, 2025 The best leaders are hardcore truth-tellers and seekers. Telling the truth is easier said than done. While most people place a high value on truth (or at least claim to), they’re not necessarily willing to face the truth—or go through the tension and discomfort required to excavate it. As Jack Nicholson famously said in A Few Good Men: “You want the truth? You can’t handle the...
25 days ago • 5 min read
What great leaders know about themselves that most others don’t What level of intensity can you sustain without crashing? It’s time to learn your Ideal RPE: Rate of Perceived Exertion. Matt Hunter • July 15, 2025 Capitalism doesn’t care about your well-being. I’ll say that one more time: Capitalism doesn’t care about your well-being. If you don’t protect yourself, the modern world will grind you down and burn you out. It’s nothing personal; that’s just the way the system was designed. Its...
about 1 month ago • 5 min read
Embrace Your Dark Side Don’t just befriend your shadow—make it work in your favor. Matt Hunter • July 1, 2025 If you want to achieve something extraordinary, you can’t ignore the hidden forces that drive you, also known as your dark side. Carl Jung called this the ‘shadow’—the unconscious, repressed aspects of ourselves that don’t fit the curated, socially acceptable version of who we’re told to be. Things like shame, guilt, unworthiness, feelings of rejection or abandonment, rage,...
about 2 months ago • 5 min read
Let Go of the Need to Be Liked Tough leaders don’t seek approval—they seek results. Matt Hunter • June 3, 2025 We all want to be liked. You, me, and pretty much everyone else you know. To seek social approval is just about the most human thing there is—but it can get us into trouble, especially as leaders. I’m just gonna go ahead and say it: Chasing likability is a trap for leaders. And it’s one that I’ve seen too many fall right into. The problem with trying to get everyone to like you is...
3 months ago • 3 min read
Ego Isn't the Enemy Stop trying to kill your ego. If you want to be a great leader, you need a strong one. Matt Hunter • May 20, 2025 "Bring your egos in. If we’re going to win, we will need your egos. Just make sure they are all under the same umbrella." - Coach K, Legendary Duke Basketball Coach. These days, the ego gets a bad rap. We hear people say that “ego is the enemy,” that our sense of self is a barrier to our purpose and goals. We see high-performers chasing “ego death” through...
3 months ago • 3 min read
Can You 'Therapize' Your Way Out of Greatness? How to take care of your mental health without killing your ambition in the process. Matt Hunter • May 6, 2025 The best leaders have an insatiable drive—one that keeps them moving forward long after others would stop. But that kind of drive doesn’t always square with our ideas of well-being and mental health. To keep their drive alive, great leaders often go to incredible lengths to prevent the complacency that comes with success. Some get...
4 months ago • 4 min read
Pick Up the Damn Phone Evaporate drama from your life by going direct. Image by Chat GPT Imagine this scenario: You pick up your phone to find a lengthy (and frustrating) text, Slack, or email. Whatever it is, it creates a jolt in your system—the information is unexpected and unwelcome, you find it hurtful or insensitive, or maybe you just disagree and think the person is wrong. So you start crafting your own lengthy reply laying out your position. If I could pause and interject, here’s what...
4 months ago • 5 min read
When Dealing with Difficult Situations, Don’t Cancel Out Conflicting Emotions In complicated situations, it’s easy for conflicting emotions to get canceled out. But we’ve gotta make space to integrate both sides of what we’re feeling. Photo by Kyle Kesterson One of my clients had a big offsite coming up for his leadership team that he’d been planning for months. It was the year's most important event, and everyone needed to be there. Sure enough, 10 days before the offsite, one of his leaders...
4 months ago • 4 min read