What does a great resume look like? How do you stand out? I’ve reviewed thousands of product manager resumes. Here’s the sad truth: most of them go straight to the shredder.

To write a resume that converts, it helps to understand the psychology of your audience. Their #1 concern: can you do the job well?

Every step in the hiring process is engineered to de-risk you. There are two proven ways to do this starting with your resume:

1. Show that you solved similar (enough) problems → relevant experience
2. Show that you quickly learn to solve new problems → strong track…

Why does everyone want to do strategy? What’s really behind execution problems? How is everyone so confident in this meeting? And is “finding purpose” overrated?

These were a few of the topics covered in a conversation with Shreyas, Evan and Karan. I learned a lot from them, and want to share the highlights with you. ‍

Strategy as intelligence?

How strategic are you? Most people will say they’re above average or maybe even exceptional. But, by definition, most people cannot be above average.

Part of the allure of strategy is that it’s seen as a proxy for intelligence. It’s why so many people…

There are two myths as old as time: 1) competition is healthy; 2) winning requires outdoing the competition. Both ideas take root during our formative years in school, and color our decision-making for the worse.‍

Why competition is (often) unhealthy

Schools drive and reflect our obsession with competition. We are taught to memorize textbook answers to win the prize of higher grades. The way to outdo each other is to do more of the same.

We then apply this to the real world. We watch competitors closely, analyze their playbook, and try to outdo them at their own game. If they have three cool features…

How do you raise millions of dollars, delight millions of customers only to be sold to a bootstrapped competitor for $35K?

This is the real story of two sites: Pinboard and Delicious. It first caught my attention because I love underdog stories. As I went down the rabbit hole, I realized it represents so much more, including:

• What customers want vs. what people are incentivized to build
• First big decision founders need to make — and employees should ask about
• How a flea can devour an elephant with the help of time and profitability‍‍

Winning formula: simple & reliable

Customers want simple and reliable solutions.

…

The story of the $300M button made a big splash over a decade ago when it was covered in a book called Web Form Design: Filling in the Blanks. The story was originally written by Jared Spool and sent to Brad Frost when he was writing the book. I recently stumbled upon it and was immediately captivated.

It’s a great example of how designs can impact a business, in this case to the tune of $300M. It’s also a reminder of how defaults matter, shape user behavior, and even influence power dynamics.‍

A simple button change

There were only two buttons: Login and Register…

I fell down the most productive rabbit hole: Shreyas Doshi’s tweets. Shreyas is a product leader at Stripe, but on the internet, he’s been breaking records for clarity of insight — 280 characters at a time.

Shreyas is like the Charlie Munger of product management: he tells stories that help you reinterpret your past, and make better decisions in the future.

Here are 5 big ideas I’ve learned from reading thousands of Tweets from him:

1. Become 10–30–50 to escape the career treadmill
2. Delegate with transparency
3. Bias for building is a double-edged sword
4. Focusing illusion leads you astray
5. Gifted Debaters win…

Since I quit my tech job, I’ve received a lot of questions: “Do you regret turning down your Instagram offer?”, “What are you doing now?”, “How does it feel to be free?”

A month in, I wrote an optimistic piece. Four months in, I’ve stepped out of the honeymoon and woken up to the good, bad, and ugly of being a solo entrepreneur.

Let’s cover wrong assumptions about starting a business, difference between employee vs. entrepreneur, and lessons to help you make the most of this new life of freedom.

First, why did I quit again?

There are two predictors of quitting your job:

1. How you…

When I became a lead PM, I made a near-fatal career mistake. I was used to working at a tiny startup. A startup is like a baby. It cries 24/7 and requires a team of heroes to keep alive. I liked being a hero, someone trusted to save the day.

A startup is also designed to grow fast. Unlike a real baby, it can become a teenager overnight. And a teenager doesn’t need a hero, it needs a guide.

Most of us see ourselves as the hero. We need to save our customers to win them over. …