What are you becoming?
Sep 29, 2025 12:40 PM
If someone watched you for a week, would they believe you are serious about your goals?
Aug 10, 2025 6:41 PM
What do you want to be doing in the last decade of your life?
Peter Attia
Jul 8, 2025 7:48 AM
What increases in value as wealth approaches infinity?
May 22, 2025 12:03 AM
What increases in value as information approaches infinity?
May 5, 2025 8:48 PM
Are your best days ahead of you, or behind you?
Apr 16, 2025 7:05 PM
Are you treating life like the dress rehearsal or the show?
Mar 26, 2025 1:41 AM
Where is it wise to compress complexity?
Mar 18, 2025 7:01 PM
What is the most obvious thing to do right now?
Mar 18, 2025 1:31 PM
What experiences would I need to have to believe what you believe?
Mar 17, 2025 11:28 AM
What would you do if you could hire a tireless genius for $20 per month?
Feb 28, 2025 6:49 PM
What would you do if you had 10x the agency you have?
Jan 30, 2025 6:42 PM
What’s the best way to think about being helpful to you?
Nov 20, 2024 3:19 AM
How can I serve you well?
Nov 20, 2024 3:19 AM
What have you recently subtracted from your life?
Jun 20, 2024 3:52 PM
Why did we mock religion, only to mimic it?
Freya India
Jun 6, 2024 4:04 PM
What knowledge work can be converted into tokens?
May 15, 2024 10:31 AM
What led you to take this meeting?
Jesse Pujji
May 6, 2024 12:27 PM
Take a few minutes and think about something you are an expert in…then explain it to me.
Apr 28, 2024 11:48 AM
When you’re told that something is impossible, is that the end of the conversation, or does that start a second dialogue in your mind?
Eric Weinstein
Jan 29, 2024 1:43 PM
If you could have the answer to any one question, what question would you want the answer to?
Max Grev
Dec 14, 2023 3:03 AM
If you could take a year off to work on something that probably wouldn't be important but would be really interesting, what would it be?
Max Grev
Dec 14, 2023 3:03 AM
What's the last thing you crossed off your bucket list?
Max Grev
Dec 14, 2023 3:02 AM
What have you been thinking about lately?
Daniel Rhodes
Dec 14, 2023 3:01 AM
Did anything happen last week that you're still thinking about?
Varadh Jain
Dec 14, 2023 3:00 AM
What are you getting most excited about right now?
Sahil Bloom
Dec 14, 2023 3:00 AM
What gifts will I leave for unborn generations to come?
Patrick O’Shaughnessy
x.com
Dec 3, 2023 3:13 PM
What do you consider to be your finest hour?
Oct 31, 2023 12:10 AM
It’s impossible to please everyone. The question is: are you disappointing the right people?
Adam Grant
Oct 16, 2023 9:01 PM
Who has deceived thee so oft as thyself?
Oct 2, 2023 2:46 PM
If someone talked to you the way you talk to yourself, would you be friends with them?
Sep 10, 2023 2:44 AM
What do you spend an unreasonable amount of time doing?
David Perell
twitter.com
Aug 12, 2023 2:35 PM
Who is good at <skill> despite being poorly built for it?
Aug 11, 2023 6:16 PM
If you were required to dispose of all but one asset, what would you keep?
Aug 11, 2023 5:45 PM
For someone who is outside your field, what would they find most surprising about your field?
Jul 29, 2023 3:22 PM
How have you evolved? Show me.
Sam Hinkie
Jul 20, 2023 3:19 PM
Regardless of what they do or produce, who do you know that has the highest quality bar?
Patrick O’Shaugnessy
Jul 20, 2023 2:33 PM
What is the return on time for <item>?
Jul 19, 2023 6:17 PM
What is the outlook AND what is the predictability of the outlook?
Jul 19, 2023 6:15 PM
What has surprised you about <topic>?
Peter Kaufman
Jul 19, 2023 6:15 PM
How do you measure yourself?
Jul 19, 2023 6:15 PM
What is most alive in you right now?
Jul 19, 2023 6:15 PM
What is calling you right now?
Jul 19, 2023 6:14 PM
DO NOT ask “what do you do?” INSTEAD ask “what are you working on?”
Jul 19, 2023 6:13 PM
Who / what are you becoming?
Mark Canlis
Jul 13, 2023 10:20 PM
What course could you teach?
Jun 23, 2023 9:24 PM
If you had to give a TED talk on something that isn’t your profession, what would it be about?
Tim Ferris
Apr 29, 2023 2:35 AM
What do you know more about than most people?
Kevin Kelly
Apr 29, 2023 2:34 AM
Would I think about the world like you do if I experienced what you have?
Apr 27, 2023 1:25 AM
What have you experienced that I haven’t that makes you believe what you do?
Apr 27, 2023 1:24 AM
Who has influenced you the most?
Feb 21, 2023 1:32 PM
Are you a lucky person?
Feb 21, 2023 1:32 PM
Have I earned my gift?
Ric Elias
overcast.fm
Feb 14, 2023 3:21 AM
What does it mean to be healthily adapted to the Internet?
thekcpgroup.com
Jan 4, 2023 9:44 PM
What have you had to unlearn? What have you unlearned recently?
Nov 4, 2022 1:31 AM
If the world were ending in 12 months, how would you spend your remaining time?
Nov 4, 2022 1:30 AM
How am I complicit in creating the conditions I say I don’t want?
Jerry Colonna
Oct 4, 2022 1:59 AM
How was your time in the desert? (as a metaphor: eg time of silence and solitude as precursors to wisdom; time of uncertainty, confusion, doubt, and loss as precursors to success)
Sep 30, 2022 3:50 PM
How do you identify quality before there is a track record?
Sep 15, 2022 2:01 PM
Ideas are networks…novel configurations of nodes in your brain. How do you get your brain into environments where new networks are more likely to form?
www.ted.com
Sep 14, 2022 8:24 PM
If you were CEO of _ tomorrow, what is the first thing you would change?
Sep 12, 2022 8:04 PM
Where are time horizons expanding?
Paul Higgins
Sep 7, 2022 6:19 PM
What needs to be done to become a wonderful ancestor?
Mike Podolsky
Sep 6, 2022 9:11 PM
What’s the view from your favorite window?
Aug 22, 2022 4:38 PM
How can I be your best customer?
Aug 12, 2022 6:46 PM
What is the hardest problem you are working on right now?
Jul 25, 2022 7:25 PM
If I don’t choose you, who would you go with?
Jul 10, 2022 1:11 PM
Favorite Manager questions from First Round (follow link)
review.firstround.com
Jun 9, 2022 12:14 AM
What are you willing to struggle for?
Mar 16, 2022 12:20 AM
What pain do you want in your life?
Mar 16, 2022 12:20 AM
What makes your best employee stand out?
Mar 6, 2022 6:01 PM
Can you be rational when you’re wrong?
Jan 31, 2022 1:28 PM
What do you wish you had told your younger self — that your younger self would have actually listened to?
Dec 31, 2021 4:38 PM
If I could somehow communicate with my future self, what would I want to know now to make the right decision today?
Nov 15, 2021 7:06 PM
What areas are under-invested due to incongruity between market size vs. the number of entrepreneurs that have experienced the problem? (Eg fewer entrepreneurs have kids vs education TAM)
Nov 14, 2021 10:43 PM
What problem would you pay the most to solve?
Nov 13, 2021 11:36 PM
What are the ingredients in having new ideas?
paulgraham.com
Nov 10, 2021 7:38 PM
If a friend came to me with the exact problems I'm facing now, what advice would I give them?
Oct 14, 2021 3:06 PM
What is one of your favorite books that has only ever been recommended by one person?
Oct 5, 2021 12:12 AM
What have you experienced that I haven't that would make me believe what you do?
Sep 25, 2021 9:52 PM
What do you know that most people (or competitors) haven't figured out, yet?
Sep 24, 2021 2:16 AM
Why won't capitalist forces erode your margins?
Aug 17, 2021 8:59 PM
Who do you want your customers to become?
Jul 22, 2021 2:47 PM
What important thing have you put in the "too hard" pile?
Apr 8, 2021 6:35 PM
What important thing have you recently struggled to understand?
Apr 8, 2021 6:34 PM
What do you love to spend time on?
Mar 20, 2021 10:31 PM
What do you love to spend money on?
Mar 20, 2021 10:30 PM
What strongly held belief do you have that most people disagree with?
Mar 18, 2021 1:39 PM
What do you know that most people do not? (often about something uncommon or unusual)
Feb 28, 2021 1:26 PM
What question would you ask to understand how someone thinks?
twitter.com
Dec 2, 2020 12:41 AM
Inspiration from Patrick Collison (follow link)
patrickcollison.com
Nov 21, 2020 1:29 PM
What is the return by security type/area? Are higher returns found in specific types of companies or situations?
Nov 21, 2020 12:40 PM
Does trading in/out of the same positions add to or subtract from returns (after-tax) over time?
Nov 21, 2020 12:36 PM
What is the return by position size? Did larger positions produce higher returns (i.e. does high conviction pay?)
Nov 21, 2020 12:34 PM
What proportion of returns are attributable to management of gross and net exposure?
Nov 21, 2020 12:25 PM
Favorite interview questions from First Round (follow link)
firstround.com
Nov 16, 2020 5:13 PM
What have you had to un-learn? What made you do it? How did you do it?
Nov 16, 2020 4:57 PM
What feedback have colleagues given about you? Do you agree/disagree? Why?
Nov 16, 2020 4:55 PM
What is the best customer service experience you've ever had?
Nov 16, 2020 4:54 PM
What do you worry about?
Nov 16, 2020 4:54 PM
What are you doing right now whose benefits will only be seen years/decades from now?
Nov 16, 2020 4:53 PM
What is your most strongly held belief?
Nov 16, 2020 4:52 PM
What hypotheses are you testing right now?
Nov 16, 2020 4:52 PM
Give me an example of a time you failed.
Nov 16, 2020 4:52 PM
What is the worst thing that has happened in your career?
Nov 16, 2020 4:52 PM
What things do you think are important to do every day?
Nov 16, 2020 4:51 PM
What feedback have clients given you about your work? Do you agree/disagree? Why?
Nov 16, 2020 4:51 PM
What are you most proud of?
Nov 16, 2020 4:44 PM