[trylfthsk]

I can understand his distaste for the indefinite, but does he actually make a strong case for the opposite?

To me this reads as claiming "making fragile choices is good", which outside of very niche situations I'd say is bad advice: like telling a college basketball player to not waste time outside of practice and later watching him go undrafted in the pros.

[dagw]

You also have to look at who is giving the advice. For him it is great if more people take huge risks and burn their youth on moon shot start-ups since, as a VC, he makes all his money off of those people. A world where everybody is a well rounded liberal arts graduate, working a steady job, with comfortable middle class lifestyle and great work life balance would be terrible for him. If you ruin your life following this advice it has zero impact on his life.

He's giving this advice to make his life better, not necessarily to make your life better.

[sitkack]

Hail marry risk is always better externalized.

[bko]

You should read his book. Here is a brief excerpt from the chapter "you are not a lottery ticket"

> THE MOST CONTENTIOUS question in business is whether success comes from luck or skill. What do successful people say? Malcolm Gladwell, a successful author who writes about successful people, declares in Outliers that success results from a “patchwork of lucky breaks and arbitrary advantages.” Warren Buffett famously considers himself a “member of the lucky sperm club” and a winner of the “ovarian lottery.” Jeff Bezos attributes Amazon’s success to an “incredible planetary alignment” and jokes that it was “half luck, half good timing, and the rest brains.” Bill Gates even goes so far as to claim that he “was lucky to be born with certain skills,” though it’s not clear whether that’s actually possible.

> Perhaps these guys are being strategically humble. However, the phenomenon of serial entrepreneurship would seem to call into question our tendency to explain success as the product of chance. Hundreds of people have started multiple multimillion-dollar businesses. A few, like Steve Jobs, Jack Dorsey, and Elon Musk, have created several multibillion-dollar companies. If success were mostly a matter of luck, these kinds of serial entrepreneurs probably wouldn’t exist.

> In January 2013, Jack Dorsey, founder of Twitter and Square, tweeted to his 2 million followers: “Success is never accidental.”

>Most of the replies were unambiguously negative. Referencing the tweet in The Atlantic, reporter Alexis Madrigal wrote that his instinct was to reply: “ ‘Success is never accidental,’ said all multimillionaire white men.” It’s true that already successful people have an easier time doing new things, whether due to their networks, wealth, or experience. But perhaps we’ve become too quick to dismiss anyone who claims to have succeeded according to plan.

> Is there a way to settle this debate objectively? Unfortunately not, because companies are not experiments. To get a scientific answer about Facebook, for example, we’d have to rewind to 2004, create 1,000 copies of the world, and start Facebook in each copy to see how many times it would succeed. But that experiment is impossible. Every company starts in unique circumstances, and every company starts only once. Statistics doesn’t work when the sample size is one.

> From the Renaissance and the Enlightenment to the mid-20th century, luck was something to be mastered, dominated, and controlled; everyone agreed that you should do what you could, not focus on what you couldn’t. Ralph Waldo Emerson captured this ethos when he wrote: “Shallow men believe in luck, believe in circumstances.… Strong men believe in cause and effect.” In 1912, after he became the first explorer to reach the South Pole, Roald Amundsen wrote: “Victory awaits him who has everything in order—luck, people call it.” No one pretended that misfortune didn’t exist, but prior generations believed in making their own luck by working hard.

> If you believe your life is mainly a matter of chance, why read this book? Learning about startups is worthless if you’re just reading stories about people who won the lottery. Slot Machines for Dummies can purport to tell you which kind of rabbit’s foot to rub or how to tell which machines are “hot,” but it can’t tell you how to win.

> Did Bill Gates simply win the intelligence lottery? Was Sheryl Sandberg born with a silver spoon, or did she “lean in”? When we debate historical questions like these, luck is in the past tense. Far more important are questions about the future: is it a matter of chance or design?