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"Winning has a price. Leadership has a price." – Michael Jordan
When The Last Dance aired, it wasn't just a nostalgic trip for basketball fans. It was a masterclass in performance, leadership, culture, and grit. For founders navigating the chaotic world of startups, the documentary is rich with moments that mirror the emotional highs, political messes, and mental discipline required to build something lasting.
Below are ten founder lessons — straight from the hardwood — backed by six championships and one of the most driven athletes in history.
In The Last Dance, Jordan says, "My mentality was to go out and win at any cost. If you don't want to live that, don't be on my team." He was intense, sometimes harsh, but it came from a place of belief — that his teammates were capable of more.
🧠 Founder Lesson: Holding your team to a high standard will never make you the most popular person in the room — but it's the only way to build a winning company. Culture is shaped by what you tolerate. Set the bar.
During the 1997–98 season, the media speculated that the Bulls' dynasty was over. Internal politics, contract disputes, and aging players dominated headlines. But Jordan and Phil Jackson stayed locked in — winning the sixth title anyway.
🧠 Founder Lesson: You'll be doubted. You'll be written off. Investors will walk. Competitors will raise more money. Focus on execution. Championship companies are built with a long-term vision — not by chasing press cycles.
While Jordan was the centerpiece, The Last Dance made it clear: without Scottie Pippen, there were no six rings. Pippen was underpaid, undervalued, and at times unhappy — but his presence was irreplaceable.
🧠 Founder Lesson: You're not building this alone. Identify your Scottie. Co-founders, first hires, or early engineers — the ones who shoulder pressure, deliver results, and make the whole better than the sum of its parts. Invest in them.
Jordan's ability to turn even minor slights into motivation is legendary. One opponent simply not shaking his hand was enough for MJ to drop 40+ points the next game. Some slights were real. Some were imagined. He didn't care.
🧠 Founder Lesson: Founders need irrational fuel. Whether it's a rejection, a snub, or an underestimated product — channel it. Not out of spite, but out of drive. Use it to keep building when no one is watching.
After their third championship, Jordan left basketball to play baseball. When he returned, he had to rebuild his body, mindset, and approach — the game had changed, and so had he. He didn't shortcut the process.
🧠 Founder Lesson: Startups don't follow straight lines. You may pivot, restart, or reenter a space with new insight. That's fine. But reentry requires humility, focus, and patience. Skip steps and you'll burn out again.
One of the strongest themes in The Last Dance was the tension between the front office (specifically GM Jerry Krause) and the players. Jordan, Pippen, and Phil Jackson knew: to win, they had to insulate the locker room from dysfunction.
🧠 Founder Lesson: Internal misalignment kills startups. Founders must protect team culture — from board politics, toxic hires, or misaligned investors. Dysfunction at the top erodes everything.
Phil Jackson introduced the "Triangle Offense" — a system that prioritized spacing, trust, and decision-making. Jordan thrived within it, but so did the rest of the team. It created flow, not just control.
🧠 Founder Lesson: Founders don't just hire great people — they build systems that empower them. Decision-making frameworks, meeting rhythms, autonomy structures. Founders who micromanage talent will lose it. Build the triangle.
Jordan knew his leadership style wasn't always likable. "You can ask all my teammates. The one thing about Michael Jordan was he never asked me to do something that he didn't f**ing do."
🧠 Founder Lesson: There will be moments when being a great leader makes you unpopular. That doesn't mean you're wrong. As long as you're consistent, lead by example, and carry the load, your team will follow.
With management forcing a breakup after the 1997–98 season, Jordan and the Bulls knew: this was the end. Instead of mailing it in or fracturing, they leaned in harder. The result? A poetic sixth championship.
🧠 Founder Lesson: Sometimes, you know a team or product is nearing the end of its arc. Don't half-step. Go all in. Finish well. Whether it's an exit, a pivot, or a wind-down — make your last dance worth watching.
The final episode ends on a raw note. Jordan gets emotional reflecting on how much he demanded of himself and others. He didn't apologize for it — but he clearly carried the weight.
🧠 Founder Lesson: There is a personal cost to building something legendary. You'll sacrifice sleep, relationships, peace of mind. Just be intentional. Choose greatness consciously — and make sure it's a game you want to win.
The Last Dance isn't just about basketball. It's a founder documentary disguised as a sports story. A portrait of how to lead when the stakes are high, the critics are loud, and the team is looking to you.
As a founder, you might not be chasing six rings — but if you're chasing impact, legacy, and excellence, you're in the same arena.
And like Jordan, you don't need everyone to like you. Just the ones in the locker room.
Written by Walter P. Hassell
"Winning has a price. Leadership has a price." – Michael Jordan
When The Last Dance aired, it wasn't just a nostalgic trip for basketball fans. It was a masterclass in performance, leadership, culture, and grit. For founders navigating the chaotic world of startups, the documentary is rich with moments that mirror the emotional highs, political messes, and mental discipline required to build something lasting.
Below are ten founder lessons — straight from the hardwood — backed by six championships and one of the most driven athletes in history.
In The Last Dance, Jordan says, "My mentality was to go out and win at any cost. If you don't want to live that, don't be on my team." He was intense, sometimes harsh, but it came from a place of belief — that his teammates were capable of more.
🧠 Founder Lesson: Holding your team to a high standard will never make you the most popular person in the room — but it's the only way to build a winning company. Culture is shaped by what you tolerate. Set the bar.
During the 1997–98 season, the media speculated that the Bulls' dynasty was over. Internal politics, contract disputes, and aging players dominated headlines. But Jordan and Phil Jackson stayed locked in — winning the sixth title anyway.
🧠 Founder Lesson: You'll be doubted. You'll be written off. Investors will walk. Competitors will raise more money. Focus on execution. Championship companies are built with a long-term vision — not by chasing press cycles.
While Jordan was the centerpiece, The Last Dance made it clear: without Scottie Pippen, there were no six rings. Pippen was underpaid, undervalued, and at times unhappy — but his presence was irreplaceable.
🧠 Founder Lesson: You're not building this alone. Identify your Scottie. Co-founders, first hires, or early engineers — the ones who shoulder pressure, deliver results, and make the whole better than the sum of its parts. Invest in them.
Jordan's ability to turn even minor slights into motivation is legendary. One opponent simply not shaking his hand was enough for MJ to drop 40+ points the next game. Some slights were real. Some were imagined. He didn't care.
🧠 Founder Lesson: Founders need irrational fuel. Whether it's a rejection, a snub, or an underestimated product — channel it. Not out of spite, but out of drive. Use it to keep building when no one is watching.
After their third championship, Jordan left basketball to play baseball. When he returned, he had to rebuild his body, mindset, and approach — the game had changed, and so had he. He didn't shortcut the process.
🧠 Founder Lesson: Startups don't follow straight lines. You may pivot, restart, or reenter a space with new insight. That's fine. But reentry requires humility, focus, and patience. Skip steps and you'll burn out again.
One of the strongest themes in The Last Dance was the tension between the front office (specifically GM Jerry Krause) and the players. Jordan, Pippen, and Phil Jackson knew: to win, they had to insulate the locker room from dysfunction.
🧠 Founder Lesson: Internal misalignment kills startups. Founders must protect team culture — from board politics, toxic hires, or misaligned investors. Dysfunction at the top erodes everything.
Phil Jackson introduced the "Triangle Offense" — a system that prioritized spacing, trust, and decision-making. Jordan thrived within it, but so did the rest of the team. It created flow, not just control.
🧠 Founder Lesson: Founders don't just hire great people — they build systems that empower them. Decision-making frameworks, meeting rhythms, autonomy structures. Founders who micromanage talent will lose it. Build the triangle.
Jordan knew his leadership style wasn't always likable. "You can ask all my teammates. The one thing about Michael Jordan was he never asked me to do something that he didn't f**ing do."
🧠 Founder Lesson: There will be moments when being a great leader makes you unpopular. That doesn't mean you're wrong. As long as you're consistent, lead by example, and carry the load, your team will follow.
With management forcing a breakup after the 1997–98 season, Jordan and the Bulls knew: this was the end. Instead of mailing it in or fracturing, they leaned in harder. The result? A poetic sixth championship.
🧠 Founder Lesson: Sometimes, you know a team or product is nearing the end of its arc. Don't half-step. Go all in. Finish well. Whether it's an exit, a pivot, or a wind-down — make your last dance worth watching.
The final episode ends on a raw note. Jordan gets emotional reflecting on how much he demanded of himself and others. He didn't apologize for it — but he clearly carried the weight.
🧠 Founder Lesson: There is a personal cost to building something legendary. You'll sacrifice sleep, relationships, peace of mind. Just be intentional. Choose greatness consciously — and make sure it's a game you want to win.
The Last Dance isn't just about basketball. It's a founder documentary disguised as a sports story. A portrait of how to lead when the stakes are high, the critics are loud, and the team is looking to you.
As a founder, you might not be chasing six rings — but if you're chasing impact, legacy, and excellence, you're in the same arena.
And like Jordan, you don't need everyone to like you. Just the ones in the locker room.
Written by Walter P. Hassell
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