Increase Your Luck

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To increase your luck, expand your luck surface. Roll the dice more often and you will roll more sixes.

Expose yourself to new opportunities: meet new people, learn different subjects, do novel things.

The scalable way to do this is by building a brand.

Leave a good impression on people, so that they reach out to you when they spot a good opportunity.

The best things happened to me this way. For example, for my first startup, I was introduced to my amazing co-founder by a mutual friend. Our mutual friend thought highly of me and knew that I was eager to work on new projects.

I didn't even know that I wanted to do a startup! Your luck surface stretches beyond your imagination. Thus, it's good to be open minded. Do random stuff. Pursue "luck surface expansion" for its own sake, not in service of short term goals.

However, it is also useful to let people know what you're looking for. It's surprising how often you get what you ask for.

It's common for successful people to attribute their success to luck. More often than not, they engineered their life so luck would go their way. They were significantly more likely to succeed than the average person. It wasn't a passive waiting game.

Of course, one's starting point matters. Privilege greatly influences one's ability to access and pursue opportunities.

Success leads to massive luck surface increases. Momentum accumulates and many successful people go on to achieve even more successful things.

Just like individuals, a company's trajectory is influenced by luck.

A recurring startup origin story is one where the company first does something that does not work. It then pivots into turning one of their side projects into the main product. Twitter, Slack and others got started this way.

Startup valuations make more sense once you account for the value of the luck surface they cast.

Large companies have massive luck surfaces. Yet, many of them systematically fail to capitalize on this luck effectively.

Examples include Blockbuster rejecting buying Netflix for $50 mil, Yahoo rejecting buying Google for $1 mil, and HP rejecting designs for Apple I.

I've witnessed these missed opportunities first-hand on a smaller scale several times in my career.

Why? What are the failure modes?

Most opportunities are hidden, not presented openly as offers. They will not inherently call for your attention and need to be spotted.

Startups are particularly attentive to these. Their survival depends on it.

One weird trick that has worked for me, both personally as well as in companies, is setting highly ambitious goals; so ambitious, that you cannot hope to achieve them by the mere execution of an existing roadmap. This forces you to be on the lookout for new opportunities.

Ambition is easier to instill in small teams when there's urgency in the mission and everyone has skin in the game. It becomes harder as an organization grows.

Most new opportunities require taking on some risk. High ambition increases your risk appetite. If you can't achieve your goals by going down the safe path, you're forced to step outside your comfort zone.

Taking on risk requires flexibility, so put yourself in a position to take risks. Many find that they are most flexible in their early 20s. To maximize luck, it's best to be very ambitious in your early 20s and to live as flexibly as your early 20s for as long as possible.

Startups are flexible early on. Before achieving product-market fit, the limited number of users means there's less risk of upsetting them with product changes. Low stakes promote quick experimentation and exploration.

Established companies have more to lose, so they create rigid structures and longer planning horizons. Higher stakes promote risk aversion and stability.

Conversely, these structures lead to bad decision making due to internal politics, misaligned incentives, or sunk cost fallacies. Startups cannot afford this and must get good at decision making.

As a final piece of advice, cultivate the habit of researching and reflecting on things.

Notice when you're ahead of the curve. Identify bets where you win on average. Make a commitment. Do this often.

To an outside observer, it will seem like luck simply always goes your way.

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