Inside the Mind of Paul Graham

Calin Drimbau

Oct 9, 2022

This post is part of our 'Entrepreneurial toolkit' series. In this series, we put together a curated list of resources on a topic that is top of mind for entrepreneurs.

We'll share some key insights from the selected clips, but we highly encourage you to listen to the clips on broadn so that you can hear the experts themselves sharing ideas, opinions, and advice.

Introduction: Paul Graham

It is hard to define who Paul Graham is. He is best known for co-founding the most successful Silicon Valley startup factory Y Combinator; before that, he was also known for inventing the programming language Lisp and his previous startup Viaweb which was acquired by Yahoo. He is at the same time a teacher and an author, with his essays on his personal website touching on a wide variety of topics from self-improvement, and startups, to Web3. 

There is no doubt that thousands of aspiring entrepreneurs want to learn from Paul Graham his wisdom. This article purports to list a variety of sources where Paul Graham’s thoughts are discussed, and provide a concise insight into the mind of Paul Graham. 

Paul Graham on How to Think For Yourself

For many people, Paul’s exceptional knowledge across different fields is the most impressive thing about him. In one of his more recent essays published on his website, Paul Graham attributed this ability to his independent-mindedness. “There are some work that you can’t do well without thinking differently from your peers”, and sometimes you have to be more than correct to stand out in your field: you have to be correct and simultaneously novel, and unique. 

While Paul Graham admits that independent-mindedness is largely inborn, there are surely ways to magnify it. He notes that who you surround yourself with will shape your thinking in the long run: some friends tend to restrain your thinking by discouraging you from trying out new things; other friends tend to be open about your explorations and even prompt you to try more. Staying away from conventional-minded people is a great start for anyone desiring to cultivate this mindset.

Paul also suggests another method: to actively form skepticism about the world around you. Taking up an attitude of constantly asking “Is that true?” can be helpful for persons who are aspiring to stand out. By adopting this stance, you essentially stand back at a sufficient distance and re-examine the fashionable ideas, to find out the flaws behind their superficial attractiveness.

Paul Graham on Maker’s Schedule, Manager’s Schedule 

When it comes to the most beloved and popular essays of Paul Graham, ‘Maker’s Schedule, Manager’s Schedule’ must be on the list. The essay has attracted a good amount of discussion over the years and has been highly praised by a variety of business professionals. 

Paul describes people on the Manager’s Schedule as planning their activity by every hour (imagine C-Suite executives booking various events throughout the day), while people on the maker’s schedule plan their activity in bigger chunks of time so that they can finish up tasks (imagine programmers who spend an afternoon fixing up bugs).

Most people are on the Maker’s Schedule: this is probably just the nature of most entry-level positions. However, when running this type of schedule you risk alienating your colleagues who may need your assistance or maybe fulfill responsibilities better when cooperating with you.

Paul argues that most powerful people adopt the Manger’s Schedule: this time planning is more flexible, allows you to pay more attention to people around you, and helps you avoid deficiency. He says that while running the Y Combinator he has helped a lot of startup founders who run the Maker’s Schedule to transform into a Manger’s Schedule, and this is where he thinks success lies.   

Paul Graham on Startup Ideas

Paul Graham gave his tip for generating startup ideas in the famous “How to Start a Startup” course series: don’t try to think of ideas consciously. The best ideas, he argued, are ones that are found unconsciously by trained minds. He said the most successful companies like Google and Airbnb always started as side-projects because they originated from unconscious sparks in founders’ brains, yet later they grow into household names. 

To do this, it is best to take your brain off autopilot. Like Alex Liberman framed it in his Founder’s Journal podcast: destroy the everyday filter we use to make us think about the world around us easily. For example, when brewing your coffee in the morning, you should question why your machine takes so long; when you put on your newly-purchased jacket, you should wonder whether it can fit more perfectly. Keep asking how things should be improved, and internalize this spirit until you find yourself generating ideas unconsciously.

Paul Graham on the Essential Elements of Startup Success

Being the co-founder of one of the most successful startup accelerators on the planet, Paul Graham must have some unique insights into which startups have bright futures. While most founders focus on selling their business models and product features, Paul Grahams tends to think that founders themselves are the most critical elements. 

Hosts of the Moonshot podcast discussed this point in one of their listeners’ favorite episodes. In the early stages where startups don’t yet have a comprehensive product performance, Paul Graham says founders are almost always more important. On the application form of Y Combinator, there are really few questions about startup ideas and products, but a lot more space is devoted to knowing about the characters and the backgrounds of the founders. 

This is a good lesson for entrepreneurs looking to raise early rounds: having a good founding team is probably the best advantage you can have.

Paul Graham on the Trade-offs of Starting a Startup 

When reflecting on his own starting path and the experiences he had at Y Combinator, Paul Graham warns people who are looking to start a startup that it may not be for everyone.

This point is also discussed on the Moonshot Podcast. The hosts of the podcast mentioned that most aspiring entrepreneurs are youngsters, and they might risk losing a precious amount of time in their life devoted to building something that will eventually lead to nothing. If your passion is not strong enough in the business you are building, or you do not have a good founding team to help you through the way, you should probably think twice before becoming a full-time entrepreneur.

Paul Graham on the Preparations Before Starting a Startup

In a classic episode, the hosts of the podcast If I was Starting Today react to several opinions from Paul Graham about what counts as good preparation for startups. 

Paul Graham himself thinks education is largely useless for starting a startup. He makes this argument by noting that you have to find the right founding team by exploring the field you are interested in, and eventually you will meet with people with similar passions, regardless of your educational background.

However, podcast hosts also mentioned that educational background can still be useful if your academic history supports the technical skills required in your business, or if your alumni circle offers great opportunities to raise money.

Paul Graham on His Own Startup Journey

If you want to revisit the journey of Paul Graham from starting Viaweb to getting acquired by Yahoo, to finally getting tired of corporate life and starting the legendary Y Combinator, definitely check out Y Combinator Startup School Radio. In Episode 35 where Paul Graham was interviewed by the podcast team, he mentioned that his greatest motivation to start the entrepreneurial journey is, in his words, ‘poverty’. Simply in the mind to get rich, Paul rode the wave of the dot com era, and finally came to be the startup master as we know it today.


Paul Graham explored various fields before his greatest success at Y Combinator, which in turn helped him accumulate so much wisdom over the years, recorded in his lectures, essays, and interviews. 

We hope the resources compiled above are helpful to get you started on getting your startup on track for product-market fit. To listen to the clips and the full episodes, sign up to broadn.