‍TL;DR – How to Guess Right Often

1. ‍✅ Use Mental Models to simplify decisions
2. ✅ Curate Key Data and ignore noise
3. ✅ Find Reference Points from past successes and failures
4. ✅ Prototype Before Committing to big bets
5. ✅ Ask for Advice from the right people
6. ✅ Work With People Who Have Done It Before to shortcut learning

During my brief time at Amazon, I had the opportunity to witness firsthand how one of the world’s most successful companies makes decisions at scale. One lesson that stood out to me was the principle of "Guess Right Often." Jeff Bezos emphasized that success is not about being right all the time—it’s about increasing the probability of making the right decisions more often than not.

At Amazon, decisions were not made based on gut feelings or pure intuition. Instead, they were structured, data-backed, and iterative, allowing the company to move fast while minimizing costly mistakes. I quickly realized that this approach wasn’t just useful for billion-dollar corporations—it’s a game-changer for entrepreneurs, executives, and anyone navigating complex decisions.

Why "Guessing Right Often" Matters

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In business and life, every decision carries a cost—time, money, reputation, or opportunity. The difference between successful people and those who struggle is not intelligence or hard work alone; it’s the ability to make better decisions more consistently.

• If you can guess right 60-70% of the time instead of 50%, you create a massive advantage.
• You avoid wasting years chasing the wrong opportunities.
• You increase your speed to market with fewer pivots and wasted resources.
• You develop confidence and clarity instead of constant second-guessing.

The good news? Guessing right often is a skill. It’s something you can train and improve. Here’s how you can start improving your decision-making today.

6 Practical Ways to "Guess Right Often"

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1. Build Mental Models – Think Smarter, Not Harder

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‍Amazon executives didn’t make random decisions—they used mental models to simplify complex problems. A mental model is a framework that helps you see patterns and avoid blind spots. Some of the best ones include:

• Second-Order Thinking – Don't just think about the immediate result; consider long-term effects.
• Inversion – Instead of asking, "How can I succeed?" ask, "How can I fail?" and avoid those mistakes.
• Regret Minimization – Bezos often asked, "Will I regret not doing this when I’m 80?" If the answer was yes, he went for it.

Action Tip: Take a current decision and apply Second-Order Thinking: What happens if it succeeds? What if it fails? What’s the ripple effect in six months?

‍2. Curate Data, Not Just Collect It

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‍At Amazon, data-driven decision-making was a fundamental principle. But more data doesn’t mean better decisions—it often leads to paralysis. The key is to curate the right data:

• Find Contradictions – If experts disagree, dig deeper. The truth is often in the middle.
• Prioritize Real-World Data – The best data comes from actual behavior, not opinions. Look at what people do, not what they say.
• Ignore Noise – Not all data is useful. Learn to filter out irrelevant or outdated information.

Action Tip: Before making a big decision, write down the 3 most important data points that should guide you. If you can’t identify them, you don’t have enough clarity yet.

‍3. Find Reference Points Before Making Big Bets

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‍Every problem you face has likely been solved in some way before. Instead of reinventing the wheel, look for reference points:

• Industry Case Studies – How did others solve a similar problem?
• Benchmarks – What are the standard success metrics for what you’re doing?
• Personal Experience – Have you faced a similar situation before? What worked?

Action Tip: Before launching a new initiative, find three similar cases where others have succeeded or failed. What patterns do you notice?

‍4. Prototype Before You Commit

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‍Amazon constantly runs small experiments before committing to big changes. Instead of making massive bets, create a low-risk test:

• Launching a product? Sell a basic version to a small group first.
• Hiring a new role? Start with a part-time or freelance engagement.
• Expanding into a new market? Run a pilot campaign before a full-scale launch.

Prototyping lets you test assumptions in the real world before committing too many resources.

‍Action Tip: Ask yourself: What’s the smallest possible test I can run to learn if this idea will work?

‍5. Ask for Advice (But Filter It Carefully)

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‍The best decision-makers ask for advice strategically—not from everyone, but from the right people.

• Talk to Practitioners – People who have actually done what you’re trying to do, not just theorists.
• Find Contrasting Views – If two smart people give opposite advice, there’s nuance you need to understand.
• Ignore Outdated Advice – The world changes fast; what worked 10 years ago may not apply today.

Action Tip: Before making a major decision, find one person who has already done it successfully and ask them what they wish they knew before they started.

‍6. Work with People Who Have Done It Before

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‍Experience shortcuts your learning curve. The fastest way to "guess right" more often is to surround yourself with people who already have a track record in what you're trying to do.

• If you’re entering a new market, partner with someone local.
• If you're launching a new product, work with someone who has done it before.
• If you’re hiring for a new skill, bring in an expert to help define what great looks like.

Action Tip: For your next big project, identify one experienced person you can collaborate with to reduce blind spots.

‍Final Thoughts

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‍The secret to "Guessing Right Often" isn’t luck—it’s a system. By applying mental models, curating data, finding reference points, prototyping, seeking advice, and working with experienced people, you dramatically increase the probability of making better, faster, and more impactful decisions. Instead of asking, "Will this decision work?"Start asking, "How can I structure this decision so that I guess right more often?"

‍That shift in thinking can change everything.

This article is part of the "Intellectual Capital Building" series.

Read more about FISH Capital here.