Embracing Disagreeableness in Entrepreneurship

Mike Maples, Jr. is a legendary early-stage startup investor and a co-founder and partner at Floodgate. He’s made early bets on transformative companies like Twitter, Lyft, Twitch, Okta, Rappi, and Applied Intuition and is one of the pioneers of seed-stage investing as a category. He’s been on the Forbes Midas List eight times and enjoys sharing the lessons he’s learned from his years studying iconic companies. In his new book, Pattern Breakers: Why Some Start-Ups Change the Future, co-authored with Peter Ziebelman, he discusses what he’s found separates startups and founders that break through and change the world from those that don’t. After spending years reviewing the notes and decks from the thousands of startups he’s known over the past two decades, he’s uncovered three ways that breakthrough founders think and act differently. In our conversation, Mike talks about:

• The three elements of breakthrough startup ideas

• Why you need to both think and act differently

• How to avoid the “comparison trap” and “conformity trap”

• The importance of movements, storytelling, and healthy disagreeableness in startup success

• How to apply pattern-breaking principles within large companies

• Mike’s one piece of advice for founders

• Much more

Pre-order Mike’s book here and get a second signed copy for free. Limited copies are available, so order ASAP: patternbreakers.com/lenny.

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Find the transcript at: https://www.lennysnewsletter.com/p/how-to-find-a-great-startup-idea-mike-maples-jr

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Where to find Mike Maples, Jr.:

• X: https://x.com/m2jr

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

• Substack: https://greatness.substack.com/

• Website: https://www.floodgate.com/

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Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

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In this episode, we cover:

(00:00) Mike’s background

(03:10) The inspiration behind Pattern Breakers

(08:09) Uncovering startup insights

(11:37) A quick summary of Pattern Breakers

(13:52) Coming up with an idea

(15:30) Inflections

(17:09) Examples of inflections

(28:10) Insights

(36:58) The power of surprises

(47:36) Founder-future fit

(55:33) Advice for aspiring founders

(56:41) Living in the future: valid opinions

(55:34) Case study: Maddie Hall and Living Carbon

(58:40) Identifying lighthouse customers

(01:00:53) The importance of desperation in customer needs

(01:03:57) Creating movements and storytelling

(01:24:22) The role of disagreeableness in startups

(01:34:42) Applying these principles within a company

(01:40:43) Lightning round

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Referenced:

• Pattern Breakers: Why Some Start-Ups Change the Future: https://www.amazon.com/Pattern-Breakers-Start-Ups-Change-Future/dp/1541704355

• Justin.tv: https://en.wikipedia.org/wiki/Justin.tv

• Airbnb’s CEO says a $40 cereal box changed the course of the multibillion-dollar company: https://fortune.com/2023/04/19/airbnb-ceo-cereal-box-investors-changed-everything-billion-dollar-company/

• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach

• The Unconventional Exit: How Justin Kan Sold His First Startup on eBay: https://medium.datadriveninvestor.com/the-unconventional-exit-how-justin-kan-sold-his-first-startup-on-ebay-4d705afe1354

• Kyle Vogt on LinkedIn: https://www.linkedin.com/in/kylevogt/

• The State of Telehealth Before and After the COVID-19 Pandemic: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9035352/

• The Craigslist Killers: https://www.gq.com/story/craigslist-killers

• The social radar: Y Combinator’s secret weapon | Jessica Livingston (co-founder of Y Combinator, author, podcast host): https://www.lennysnewsletter.com/p/the-social-radar-jessica-livingston

• Michael Seibel on LinkedIn: https://www.linkedin.com/in/mwseibel/

• The Airbnb Story: How Three Ordinary Guys Disrupted an Industry, Made Billions ... and Created Plenty of Controversy: https://www.amazon.com/Airbnb-Story-Ordinary-Disrupted-Controversy/dp/0544952669

• Scott Cook: https://www.forbes.com/profile/scott-cook/

• Chegg: https://www.chegg.com/

• Aayush Phumbhra on LinkedIn: https://www.linkedin.com/in/aayush/

• Osman Rashid on LinkedIn: https://www.linkedin.com/in/osmanrashid/

• Okta: https://www.okta.com/

• The Man Who Makes the Future: Wired Icon Marc Andreessen: https://www.wired.com/2012/04/ff-andreessen/

• Peter Ludwig on LinkedIn: https://www.linkedin.com/in/peterwludwig/

• Qasar Younis on LinkedIn: https://www.linkedin.com/in/qasar/

• Paul Allen’s website: https://paulallen.com/

• Louis Pasteur quote: https://www.forbes.com/quotes/6145/

• What was Atrium and why did it fail? https://www.failory.com/cemetery/atrium

• Patrick Collison on LinkedIn: https://www.linkedin.com/in/patrickcollison/

• Drew Houston on LinkedIn: https://www.linkedin.com/in/drewhouston/

• William Gibson’s quote: https://www.goodreads.com/quotes/681-the-future-is-already-here-it-s-just-not-evenly

• Maddie Hall on LinkedIn: https://www.linkedin.com/in/maddie-hall-76293135/

• Living Carbon: https://www.livingcarbon.com

• Zenefits (now Trinet): https://connect.trinet.com/

• Sam Altman on X: https://x.com/sama

• Steve Wozniak on LinkedIn: https://www.linkedin.com/in/wozniaksteve/

• Horsley Bridge Partners: https://www.horsleybridge.com/

• David Swensen: https://en.wikipedia.org/wiki/David_F._Swensen

• Judith Elsea on LinkedIn: https://www.linkedin.com/in/judithelsea/

• 7 Powers: The Foundations of Business Strategy: https://www.amazon.com/7-Powers-Foundations-Business-Strategy/dp/0998116319

• Business strategy with Hamilton Helmer (author of 7 Powers): https://www.lennysnewsletter.com/p/business-strategy-with-hamilton-helmer

• Lyft’s Focus on Community and the Story Behind the Pink Mustache: https://techcrunch.com/2012/09/17/lyfts-focus-on-community-and-the-story-behind-the-pink-mustache/

• Logan Green on LinkedIn: https://www.linkedin.com/in/logangreen/

• John Zimmer on LinkedIn: https://www.linkedin.com/in/johnzimmer11/

• Storytelling with Nancy Duarte: How to craft compelling presentations and tell a story that sticks: https://www.lennysnewsletter.com/p/storytelling-with-nancy-duarte-how

• Steve Jobs Introducing the iPhone at MacWorld 2007: https://www.youtube.com/watch?v=x7qPAY9JqE4

• Jonathan Livingston Seagull: https://www.amazon.com/Jonathan-Livingston-Seagull-Richard-Bach/dp/0743278909

• The paths to power: How to grow your influence and advance your career | Jeffrey Pfeffer (author of 7 Rules of Power, professor at Stanford GSB): https://www.lennysnewsletter.com/p/the-paths-to-power-jeffrey-pfeffer

• Robin Roberts on LinkedIn: https://www.linkedin.com/in/robin-roberts-393a934b/

• Skunkworks: https://www.lockheedmartin.com/en-us/who-we-are/business-areas/aeronautics/skunkworks.html

• Vision, conviction, and hype: How to build 0 to 1 inside a company | Mihika Kapoor (Product at Figma): https://www.lennysnewsletter.com/p/vision-conviction-hype-mihika-kapoor

• Hard-won lessons building 0 to 1 inside Atlassian | Tanguy Crusson (Head of Jira Product Discovery): https://www.lennysnewsletter.com/p/building-0-to-1-inside-atlassian-tanguy-crusson

• Figma: https://www.figma.com/

• Atlassian: https://www.atlassian.com/

• Vinod Khosla: https://www.khoslaventures.com/team/vinod-khosla/

• Top Five Regrets of the Dying: A Life Transformed by the Dearly Departing: https://www.amazon.com/Top-Five-Regrets-Dying-Transformed-ebook/dp/B07KNRLY1L

• Chase, Chance, and Creativity: The Lucky Art of Novelty: https://www.amazon.com/Chase-Chance-Creativity-Lucky-Novelty/dp/0262511355

• Clay Christensen’s books: https://www.amazon.com/stores/Clayton-M.-Christensen/author/B000APPD3Y

• Resonate: Present Visual Stories That Transform: https://www.amazon.com/Resonate-Present-Stories-Transform-Audiences/dp/0470632011

• Ferrari on Prime: https://www.amazon.com/Ferrari-Adam-Driver/dp/B0CNDBN672

• Montblanc fountain pens: https://www.montblanc.com/en-us

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

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Lenny may be an investor in the companies discussed.

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