Launching September 2026
A field guide to leading
product strategy
by making better bets.
For product and company leaders who need to make a real strategy, and make that strategy real.
Get the launch date and a sample chapter when it ships. No spam.
The problem
Most "strategies" aren't.
They're plans, roadmaps, goals, budgets, and wishlists standing in for the real thing.
The promise
The Strategy Cycle is a hands-on field guide to actually doing strategy: using what you control to impact what you don't.
Read it on a flight, use it when you land. About a 3-hour read.
Inside the book
Craft the strategy.
Live the strategy.
Repeat.
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Living in bets
Why most "strategies" aren't, and what to do instead.
Strategy is an evolving theory of winning, expressed through a cycle of bets. If planning is painful, it's often a sign of a weak or missing strategy.
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Part OneCraft the strategyMake the actual choices a real strategy is made of and bring people along for the ride, building alignment every step of the way.
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Start with a strategy sketch
A working draft of your strategy on paper by the end of chapter one.
The two-page sketch you can come back to and sharpen with each cycle. Start rough, get something real on the page, then make it strong.
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Distill the context
What's going on?
Understand where things are, where they're going, and why. Use this to distill the beliefs at the foundation of your strategy.
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Frame the challenge
What must we solve?
Identify the real challenges, narrow to the one that matters, and write a crisp challenge statement. If you can't name it in a sentence, you have a wishlist, not a strategy.
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Define the value thesis
Why will customers choose us, and keep choosing us?
Get specific about who you're for, what they're really hiring you to do, and how you'll build durable, differentiated value. This is the core of your strategy.
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Develop the approach
How will we make this real?
Translate the value thesis into the strategic themes you'll go after. Develop the big moves, the logic that connects them, and stress-test the approach before you commit to it.
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Decide the bets
What will we do, not do, and why?
Draft a portfolio of bets to put the strategy into action, draw the line on what's in and out, and document the rationale so it can travel well.
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But what about…?
Real answers for the questions every strategy hits on contact with reality.
Edge cases and practical FAQs like:
- What about AI?
- What's the fastest version of this?
- What if there's no business strategy?
- What if we have no differentiation?
- Why is strategy so damn hard?
…and more real-world issues.
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Part TwoLive the strategyCrafting a strong strategy is maybe 40% of the work. The other 60% is deploying it, managing it, and evolving it.
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Deploy the strategy
Place your bets.
Communicate, operationalize, and verify understanding to create the conditions for highly aligned, autonomous decision making. This is where planning lives.
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Manage the strategy
Live your bets.
The ongoing, active work to keep the strategy alive and stay on course after week two of the quarter, when the shiny new things start arriving.
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Evolve the strategy
Choose again.
Run the cycle again. The first cycle is the heaviest lift: after that, most quarters are a refresh, not a restart. Use what you've learned to sharpen the bets and make the strategy stronger.
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Becoming a strategist
Be someone who leads strategy. Not someone who wrote a strategy once.
The best strategists aren't the ones who know the most frameworks. They're the ones with the judgment to know what matters, the conviction to make hard choices, and the humility to change course when reality says they should.
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Segmentation, JTBD, Differentiation, Defensibility
Deeper dives on the four components at the heart of your strategy.
Pull these in when you need them. Reference material for the moments where the main path needs more horsepower under the hood.