logo
episode-header-image
May 2024
1h 21m

This will make you a better decision-mak...

Lenny Rachitsky
About this episode

Annie Duke is a former professional poker player, a decision-making expert, and a special partner at First Round Capital. She is the author of Thinking in Bets (a national bestseller) and Quit: The Power of Knowing When to Walk Away and the co-founder of the Alliance for Decision Education, a nonprofit whose mission is to improve lives by empowering students through decision skills education. In our conversation, we cover:

• What Annie learned from the late Daniel Kahneman

• The power of pre-mortems and “kill criteria”

• The relationship between money and happiness

• The power of “mental time travel”

• The nominal group technique for better decision quality

• How First Round Capital improved their decision-making process

• Many tactical decision-making frameworks

Brought to you by:

Vanta—Automate compliance. Simplify security.

UserTesting—Human understanding. Human experiences.

LinkedIn Ads—Reach professionals and drive results for your business

Find the transcript at: https://www.lennysnewsletter.com/p/making-better-decisions-annie-duke

Where to find Annie Duke:

• X: https://twitter.com/AnnieDuke

• LinkedIn: https://www.linkedin.com/in/annie-duke/

• Website: https://www.annieduke.com/

• Substack: https://www.annieduke.com/substack/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Annie’s background

(03:53) Lessons from Daniel Kahneman: humility, curiosity, and open-mindedness

(09:15) The importance of unconditional love in parenting

(15:15) Mental time travel and “nevertheless”

(20:06) The extent of improvement possible in decision-making 

(24:54) Independent brainstorming for better decisions

(35:36) Making sure people feel heard

(42:41) The “3Ds” framework to make better decisions

(44:49) Decision quality

(55:46) Improving decision-making at First Round Capital

(01:05:05) Using pre-mortems and kill criteria

(01:10:15) Making explicit what’s implicit

(01:10:55) The challenges of quitting and knowing when to walk away

(01:19:23) Where to find Annie

Referenced:

• Daniel Kahneman, Who Plumbed the Psychology of Economics, Dies at 90: https://www.nytimes.com/2024/03/27/business/daniel-kahneman-dead.html

• Adversarial collaboration: https://en.wikipedia.org/wiki/Adversarial_collaboration

• Does more money correlate with greater happiness?: https://penntoday.upenn.edu/news/does-more-money-correlate-greater-happiness-Penn-Princeton-research#

• Income and emotional well-being: A conflict resolved: https://pubmed.ncbi.nlm.nih.gov/36857342/

• Strategic decisions: When can you trust your gut?: https://www.mckinsey.com/capabilities/strategy-and-corporate-finance/our-insights/strategic-decisions-when-can-you-trust-your-gut

• Cass Sunstein on X: https://twitter.com/CassSunstein

• Dr. Becky on Instagram: https://www.instagram.com/drbeckyatgoodinside

• A framework for finding product-market fit | Todd Jackson (First Round Capital): https://www.lennysnewsletter.com/p/a-framework-for-finding-product-market

• First Round Capital: https://firstround.com/

• Brett Berson on X: https://twitter.com/brettberson

• Renegade Partners: https://www.renegadepartners.com/

• Renata Quintini on X: https://twitter.com/rquintini

• Roseanne Wincek on X: https://twitter.com/imthemusic

• Josh Kopelman on X: https://twitter.com/joshk

• Bill Trenchard on X: https://twitter.com/btrenchard

• Linnea Gandhi on X: https://twitter.com/linneagandhi

• Maurice Schweitzer on X: https://twitter.com/me_schweitzer

• Problems with premortems: https://sjdm.org/presentations/2021-Poster-Gandhi-Linnea-debiasing-premortem-selfserving~.pdf

• Create a Solid Plan on How to Fail Big This Year: https://www.forbes.com/sites/forbesfinancecouncil/2020/02/07/create-a-solid-plan-on-how-to-fail-big-this-year/

Quit: The Power of Knowing When to Walk Away: https://www.amazon.com/Quit-Power-Knowing-When-Walk/dp/0593422996/

• Richard Thaler on X: https://twitter.com/R_Thaler

• Stewart Butterfield on X: https://twitter.com/stewart

• Glitch: https://en.wikipedia.org/wiki/Glitch_(video_game)

• How the Founder of Slack & Flickr Turned Colossal Failures into Billion-Dollar Companies: https://medium.com/swlh/how-the-founder-of-slack-flickr-turned-failures-into-million-and-billion-dollar-companies-7bcaf0d35d66

• The Most Fascinating Profile You’ll Ever Read About a Guy and His Boring Startup: https://www.wired.com/2014/08/the-most-fascinating-profile-youll-ever-read-about-a-guy-and-his-boring-startup/

• The Alliance for Decision Education: https://alliancefordecisioneducation.org/

• Make Better Decisions course on Maven: https://maven.com/annie-duke/make-better-decisions

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
Up next
Nov 23
A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett
<p><strong>Rachel Lockett</strong> is a sought-after executive coach and former HR leader at Stripe and Pinterest who now works with CEOs, founders, and tech leaders on emotional intelligence, resilience, and leadership skills. In this episode, Rachel shares powerful frameworks f ... Show More
1h 45m
Nov 20
Slack founder: Mental models for building products people love ft. Stewart Butterfield
<p><strong>Stewart Butterfield</strong> is the co-founder of Slack and Flickr, two of the most influential products in internet history. After selling Slack to Salesforce in one of tech’s biggest acquisitions, he’s been focused on family, philanthropy, and creative projects. In t ... Show More
1h 30m
Nov 16
The Godmother of AI on jobs, robots & why world models are next | Dr. Fei-Fei Li
<p><strong>Dr. Fei-Fei Li </strong>is<strong> </strong>known as the “godmother of AI.” She’s been at the center of AI’s biggest breakthroughs for over two decades. She spearheaded ImageNet, the dataset that sparked the deep-learning revolution we’re living right now, served as Go ... Show More
1h 19m
Recommended Episodes
Oct 2020
#233 - Annie Duke - How To Make Better Decisions
Annie Duke is a professional poker player and an author. The quality of our life depends upon the quality of our decisions. As a poker player who has competed at the biggest tournaments in the world, Annie understands the value of making good decisions under pressure. Expect to l ... Show More
1h 30m
Mar 2018
Thinking in Bets with Annie Duke
Daily life requires numerous decisions. Some easy, some difficult. And some that have to be made without knowing a lot of pertinent information. And what we think is the best decision in the moment, doesn’t necessarily yield the best outcome. No one knows this better than our gu ... Show More
31m 7s
Aug 2022
How to Make Better Decisions
<p>Can you get better at decision-making with practice? Many founders, investors, and builders must make many critical decisions, big and small, every day, and improving the quality of your decision-making process can become a big competitive advantage. </p><p>In this episode fro ... Show More
45m 11s
Apr 2024
TIP623: The Art Of Decision Making w/ Annie Duke
Kyle Grieve chats with Annie Duke about her own story of quitting and how it helped sparked the idea for one of her books, the importance of base rates in helping us make better decisions, how to improve our investing processes when we have long feedback loops, the importance of ... Show More
1h 10m
Jan 2023
75. Love & Money: How to Talk About Big Decisions Together
<p>Do love and money mix? Labor economist and Stanford Graduate School of Business professor emerita <a href="https://www.fastersmarter.io/guests/myra-strober/">Myra Strober</a> says absolutely. </p><p>“Separating money and love is not a good idea. I have had 40 years to think ab ... Show More
25m 47s
May 2021
How to Think Like a Breadwinner and Transform Your Money| Jennifer Barrett
Are the choices you’re making with your money bringing you closer to the future you want or further away? We’ll uncover how to think like a breadwinner and transform your money in this episode with author, journalist, and financial expert, Jennifer Barrett. Jennifer Barrett is th ... Show More
47m 50s
Apr 2022
How To Invest Like An Optimist With Morgan Housel
<p>Morgan Housel (<a href="https://twitter.com/morganhousel">@morganhouse</a>l) sits down with host Sahil Bloom for a deep dive on money and success. Morgan shares the powerful story of how he went from a 20-year-old with an 8th-grade education to a distinguished writer and partn ... Show More
1h 5m
Jan 2023
An Intelligent Roadmap for Life's Biggest Decisions | Abby Davisson
In today’s episode, we cover money and love with Abby Davisson. Abby is a social innovation leader and career development expert, was the president of the Gap Foundation at Gap Inc and a senior leader on the Environmental, Social & Governance team, and is the co-author of Money a ... Show More
1h 5m
Feb 2024
Jay Z's Autobiography
What I learned from reading Decoded by Jay Z.  ---- Get access to the World’s Most Valuable Notebook for Founders at Founders Notes ---- (1:39) I would practice from the time I woke in the morning until I went to sleep (2:10) Even back then I though I was the best. (2:57) Bourdai ... Show More
2h 7m
Oct 2023
118. Overcoming Financial Anxiety with Farnoosh Torabi
Are financial fears holding you back? Have you ever felt anxious about money or career choices? In this episode of Financial Feminist, Tori engages in a candid money conversation with Farnoosh Torabi, a renowned financial expert, author, and host of the "So Money" podcast. Farnoo ... Show More
1 h