♖ Strategy Masterclass: OKC's Sam Presti

Hi Friends,

Could you recall the happiest day of your childhood?

Mine was June 22, 1994.

The Houston Rockets had just won their first NBA championship, beating the New York Knicks in Game 7.

I was 8, watching our entire city explode with joy. My family was jumping and screaming. Neighbors were honking their horns in the street.

It was pure magic.

I bought this commemorative watch to always bring me back to that special memory.

30 years later, the Houston Rockets are now back as one of the hottest teams in the NBA, building something special again.

They stole their playbook from a small-market team in Oklahoma City.

This year, the Oklahoma City (OKC) Thunder won their first NBA championship with one of the youngest, cheapest rosters in the league.

The secret? Sam Presti’s (OKC’s General Manager) long-term, disciplined strategy that most leaders are too impatient to attempt.

The Strategic Pivot

July 2019. Presti just traded away Westbrook and Paul George, their two superstars.

Fans furious. Season ticket holders demanding answers. Media calling it malpractice.

Instead of hiding, Presti did something unprecedented: he laid out his entire long-term strategy in a public letter in the local newspaper.

The Proof: 6 Years of Strategic Execution

OKC's transformation:

• 2017-2019: Competitive but stuck with aging stars.

• 2019: The Letter + teardown begins.

• 2020-2022: Strategic suffering (22, 24, 40 wins).

• 2023-2025: Methodical climb to the championship.

Most organizations stay trapped in the mediocre middle. Good enough to survive, not bold enough to dominate. Presti chose the valley to reach the peak. That's the difference between a good strategy and no strategy.

Why This Strategy Actually Worked

Teams say they're "rebuilding" all the time. Presti documented it. Then executed it. He did three unique things.

1. He chose time over optics

Most executives optimize for quarterly results. Presti optimized for long-term results. When everyone else was making moves to look good in year one, he was making moves that would pay off in year five.

The brutal truth: Real competitive advantage takes longer to build than anyone wants to admit. But that's exactly why it's an advantage.

2. He went all-in on talent development, his superpower

This separates Presti from every other GM. His eye for talent is supernatural.

Key picks: Durant, Westbrook, Harden, Ibaka, Shai, Chet.

But here's what's missed: Presti built a machine for finding overlooked talent. While other teams fought over obvious stars, OKC was identifying diamonds in the rough. They turned draft picks into currency, creating more opportunities to be right.

The compound effect: One great pick gives you trade leverage. Multiple great picks give you a dynasty.

3. He embraced their weaknesses

Most small-market teams pretend they can compete like the big guys. Presti told the truth:

Instead of chasing expensive free agents who didn't want OKC anyway, he flipped it. Can't buy stars? Build them.

This wasn't acceptance. It was strategic clarity. When you stop pretending you have advantages you don't have, you can focus all energy on the advantages you do have.

What You Can Steal From Presti

You don't need to run an NBA team to follow his playbook:

1. Choose long-term discipline over short-term convenience
Every quarter, you'll face it: comfort now or greatness later. Markets want quick wins. Investors want instant results. Choose the path that generates long-term sustainability. Compound progress beats quick fixes.

2. Be brutally honest about your weaknesses
Most leaders pretend they can compete like the big players. Presti didn't. He admitted OKC was small, couldn't attract stars, had disadvantages. That brutal honesty became his strategy. Stop pretending. Your limitations, embraced, become your direction.

3. Communicate transparently when everyone expects silence
Your darkest moments aren't when you hide, they're when you double down. Write the letter your team needs. Tell them why the pain's worth it. Most leaders disappear when it gets hard. Be the one who shows up.

The Lesson That Lives Rent-Free in My Head

For those curious, Sam Presti's full letter from The Oklahoman, July 25, 2019 below (3 pages).

Highly recommend reading it even if you don’t care about basketball. Great reminder why great vision / strategy communication works well in a narrative format (not decks).

There is a section in the letter Presti used the city's own history as his North Star.

He referenced Oklahoma City's MAPS program, a tax initiative in the 1990s that rebuilt downtown OKC. It took years to show results. Critics called it a waste.

But the people stuck with the plan. Today, downtown OKC thrives.

Presti essentially said: "You've done this before. We will do it again."

I really enjoyed that strategic storytelling.

Final Thought

Sam Presti executed a masterclass in strategic thinking & execution.

He embraced constraints, doubled down on unique strengths, and maintained discipline through years of criticism.

Championship won. Strategic conviction rewarded.

See you next week,
—Ali

P.S. What challenge are you dealing with that you wish I had researched and written about? Let me know. Respond to this email. I read every response.

About Me: I’m Ali, a former tech exec who now advises growth-stage B2B companies on strategy & GTM execution. And I am calling it now, the Houston Rockets will beat the OKC Thunder and go on and be the 2026 NBA Champions.