Mike Maples, Jr. (Founding Partner at Floodgate, ex-Product 07 July 2024

Pattern Breakers: How to find a breakthrough startup idea

8Frameworks

12Insights

Episode overview

Lenny Rachitsky interviews early-stage investor Mike Maples, Jr. about research into why some startup ideas break through while apparently well-run companies fail. Maples argues that breakthrough ideas combine inflections, non-consensus insights, and founder-future fit, then attract early believers through movements, storytelling, and principled disagreeableness. They ground the framework in examples including Lyft, Twitch, Airbnb, Okta, Tesla, and Applied Intuition, and discuss how autonomous teams can pursue pattern-breaking ideas inside large companies.

Key ideas

Breakthrough startup ideas tend to combine an external inflection, a non-obvious insight about harnessing it, and strong founder-future fit.
Startups beat incumbents by proposing a radically different future and forcing a choice, not by executing a slightly better version of the present.
Founders can earn secrets by working at the cutting edge, designing experiments that permit surprise, and distinguishing a wrong insight from a wrong implementation or customer.
Living in the future—or serving lighthouse customers who do—improves the odds of noticing valuable things that have not yet been built.
Early customers must be desperate for the startup's unique empowerment, because startups lack the resources to win through polished execution alone.
Movements mobilize early believers around a shared grievance and higher-purpose future; effective stories cast those believers, rather than founders, as the heroes.
Pattern-breaking founders must tolerate disagreement and nonconformity while remaining open enough to understand advice and then choose their own course.
Large companies should isolate high-upside pattern-breaking projects in autonomous teams, allow many small failures, and avoid forcing premature scale targets.

Transcript available · source text is retained privately and is not published

Frameworks in this episode

Innovation4 steps

Earn the Secret by Savoring Surprises

There's no recipe for a breakthrough — hunt surprises at the edge instead of validation

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Strategy4 steps

Force a Choice, Not a Comparison

Be the world's first banana, not a 10x better apple

Read →

Entrepreneurship4 steps

Live in the Future and Notice What's Missing

Don't try to think of a startup idea — get out of the present so ideas find you

Read →

Innovation4 steps

Pattern-Breaking Inside a Big Company

Make small bets that can fail a lot — and hide them from the mother ship

Read →

Innovation4 steps

The Inflection Stress Test

Four questions that separate a real inflection from a vague 'why now'

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Entrepreneurship4 steps

The Three Elements of a Breakthrough Idea

Grade any startup idea on inflections, insight, and founder-future fit — not the implementation

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Leadership3 steps

The Three Pattern-Breaking Actions

Movements, storytelling, and disagreeableness — how you get people to move to your future

Read →

Communication3 steps

The Three-Slide Believer Pitch

What you do, your non-obvious insight, then proof — built for believers, not objectors

Read →

People & resources mentioned

Attributed to the moment in the episode. Timestamps are approximate.

People · 25

Mike Maples Jr.MentionsMike is a legendary early stage startup investor and with his firm Floodgate
“today my guest is Mike Maples Jr”
▶ Watch at ~1:00approx.
Lenny RachitskyMentionstoday we've got another very special compilation episode something I've been pulling on more and more with the podcast and the newsletter
“today my guest is Mike Maples Jr”
▶ Watch at ~1:00approx.
Paul GrahamMentionsPaul Graham talks about this too right just like live in the future and build it
“Paul Graham and her did not like the airb be idea”
▶ Watch at ~32:00approx.
Jessica LivingstonMentionsToday my guest is Jessica Livingston. Jessica is the co-founder of Y Combinator
“I had Jessica Livingston on the podcast recently”
▶ Watch at ~32:00approx.
Michael SeibelMentionsY Combinator partner who informally advised Chesky and asked him to help future founders in return.
“Michael cyel from who was one of the co-founders of Justin TV twitch”
▶ Watch at ~32:30approx.
Brian CheskyMentionsBrian chesky at Airbnb there was a whole article where we unpacked this moment in their product development cycle
“Michael introduced me to Brian chesy before they applied to YC combinator”
▶ Watch at ~32:30approx.
Albert EinsteinCoinedThere's that great Einstein quote about insanity being repeating things that you're doing, expecting a different outcome.
“the general theory of relativity had to be discovered by Einstein”
▶ Watch at ~37:00approx.
Scott CookMentionsthere's the story about Scott Cook watching his wife balancing her checkbook at the kitchen table
“I learned this lesson from Scott Cook who was the founder of Inuit”
▶ Watch at ~38:00approx.
Marc AndreessenMentionsMark Andre had this visual on some podcasts have just imagined a 100,000 drones just coming out of China just at us.
“Mark andreson started Netscape as a programmer making minimum wage at the University of Illinois”
▶ Watch at ~47:30approx.
Todd McKinnonMentionsfrom Salesforce
“they're going to trust Todd McKinnon from Salesforce”
▶ Watch at ~50:00approx.
Louis PasteurCoinedmentioned
“Louie Pastor once said Chance favors the prepared mind”
▶ Watch at ~51:00approx.
Maddie HallMentionsstarted Living carbage
“mdy Hall who started Living carbage she was working at Zenit”
▶ Watch at ~57:00approx.
Sam AltmanMentionsthere's everybody has uh and had and continues to have like such deep trust in in Sam and Greg and our leadership team
“she decided to go follow Sam Alman for a year to be his chief of staff”
▶ Watch at ~57:30approx.
Martin Luther King Jr.Mentionsif Dr King had slides that day of the I Have a Dream speech
“social movements like civil rights movement in Martin Luther King”
▶ Watch at ~1:05:00approx.
Clarence BirdseyeCoinedmentioned
“Clarence bird's eye discovered how to flash freeze food”
▶ Watch at ~1:08:30approx.
Nancy DuarteMentionsAuthor whose work JM Nichols gives to product managers developing communication, storytelling, and presentation skills.
“NY dwarte in the podcast she's one of the most famous presentation designers”
▶ Watch at ~1:17:00approx.
Steve JobsMentionsSteve Jobs is just uh the bar he held for the company and for technical talent and for excellence was not uh wavering.
“Nancy would show me how Steve Jobs's iPhone launch speech”
▶ Watch at ~1:17:30approx.
Ev WilliamsMentionsmentioned
“when I would meet with EV Williams my whole job was to give him advice that he ignored”
▶ Watch at ~1:26:00approx.
Bill GatesMentionsI think that J Leno is a greater philanthropist than Bill Gates
“my dad worked for Bill Gates when he was at Microsoft”
▶ Watch at ~1:27:00approx.
Elon MuskMentionsWhether you like him or not, Elon, this is similar to his um if you watch him, he has sets these really ambitious goals
“people can't work for Elon Musk for very long but almost everybody I know who worked for him really respects him”
▶ Watch at ~1:27:30approx.
Jeffrey PfefferMentionsHe teaches this class at Stanford Business School about how to how to gain power in the world.
“a recent podcast episode of Jeffrey feffer which I know you listen to where he talks about the rules of power”
▶ Watch at ~1:28:00approx.
Bronnie WareCoinedshe was a hospice nurse
“top five regret of the Dying by bronny where she was a hospice nurse”
▶ Watch at ~1:40:30approx.
James H. AustinCoinedmentioned
“Chase chance and creativity by a guy named James Austin”
▶ Watch at ~1:41:00approx.
Clayton ChristensenRecommendsManagement thinker admired by Eric Ries whose endorsement of Ries's work was personally important to him.
“I've always liked all of Kay christensen's books”
▶ Watch at ~1:41:30approx.
Robert GreeneCoinedmentioned
“by Robert Green the laws of human nature”
▶ Watch at ~1:42:00approx.

Resources · 56

FloodgateMentionscompany · Mike Maples Jr.
“with his firm Floodgate which was found out over 20 years ago”
▶ Watch at ~1:00approx.
TwitterMentionswebsite · Twitter
“transformative companies like Twitter Lyft twitch OCTA rappy and applied intuition”
▶ Watch at ~1:00approx.
AmazonMentionscompany · Jeff Bezos
“twitch was acquired by Amazon for 970 million”
▶ Watch at ~3:30approx.
TwitchMentionscompany
“twitch was acquired by Amazon for 970 million”
▶ Watch at ~3:30approx.
Justin.tvMentionscompany
“I invested in a company called Justin TV that had morphed into two companies”
▶ Watch at ~4:00approx.
SocialcamMentionsproduct
“Justin TV that had morphed into two companies social Cam and twitch”
▶ Watch at ~4:00approx.
Business Model CanvasMentionstool · Alexander Osterwalder and Yves Pigneur
“I didn't see the Twitter guys doing the business model canvas”
▶ Watch at ~4:30approx.
AnvilMentionssoftware · Anvil
“Anvil their document SDK helps product teams build and launch software for documents fast”
▶ Watch at ~6:30approx.
TrainspottingMentionsfilm · Danny Boyle
“there's a movie that came out a few years ago called train spotting”
▶ Watch at ~8:00approx.
PinterestMentionscompany · Pinterest
“I have the pitch deck for Pinterest”
▶ Watch at ~9:00approx.
AirbnbMentionscompany · Brian Chesky, Joe Gebbia, and Nathan Blecharczyk
“I have the original pitch deck for what was at the time called airbed and breakfast”
▶ Watch at ~9:00approx.
UberMentionscompany · Uber
“when Lyft launched ride sharing and then Uber closely followed”
▶ Watch at ~12:30approx.
LyftMentionscompany
“when Lyft launched ride sharing and then Uber closely followed”
▶ Watch at ~12:30approx.
Pattern Breakers: Why Some Start-Ups Change the FutureCoinedbook · Mike Maples, Jr. and Peter Ziebelman
“the original notion behind pattern breaking was you want to have an idea that just radically breaks the pattern”
▶ Watch at ~13:30approx.
iPhone 4SMentionsproduct · Apple
“the inflection that enabled lift was the iPhone 4S shipped with a GPS locator chip”
▶ Watch at ~15:30approx.
InstagramMentionssoftware · Meta
“the cameras getting better on the smartphones which enabled Instagram”
▶ Watch at ~17:00approx.
DoorDashMentionscompany · DoorDash
“the locator chips and the smartphones powered other companies as well powered door Dash instacart”
▶ Watch at ~18:00approx.
InstacartMentionscompany · Apoorva Mehta, Max Mullen, and Brandon Leonardo
“the locator chips and the smartphones powered other companies as well powered door Dash instacart”
▶ Watch at ~18:00approx.
ChatGPTMentionssoftware · OpenAI
“it makes me think about chaty BT when it came out it was sitting on top of an existing model”
▶ Watch at ~19:30approx.
YouTubeMentionswebsite · Google
“they had YouTube on the cover of the magazine”
▶ Watch at ~23:00approx.
Facebook ConnectMentionssoftware · Facebook
“Facebook connect made it possible to pass people's profile information”
▶ Watch at ~24:00approx.
ZoomMentionssoftware · Zoom Video Communications
“I would say that Zoom was another example”
▶ Watch at ~27:00approx.
Y CombinatorMentionscompany · Paul Graham and co-founders
“before they applied to YC combinator”
▶ Watch at ~32:30approx.
WordPressUsessoftware · Matt Mullenweg
“they put up this WordPress site to pay for their rent”
▶ Watch at ~33:30approx.
TextbookflixUseswebsite
“they created a fake site called textbook flick”
▶ Watch at ~39:00approx.
CheggMentionscompany
“a good example would have been what the guys at CH did”
▶ Watch at ~39:00approx.
OktaMentionscompany
“OCTA at first they wanted to do Cloud systems management”
▶ Watch at ~43:00approx.
NetscapeMentionscompany · Marc Andreessen and Jim Clark
“Mark andreson started Netscape as a programmer”
▶ Watch at ~47:30approx.
SalesforceMentionscompany · Salesforce
“they're going to trust Todd McKinnon from Salesforce”
▶ Watch at ~50:00approx.
Silicon GraphicsMentionscompany
“when I was at silk and Graphics”
▶ Watch at ~53:00approx.
Industrial Light & MagicMentionscompany
“I spent time with industrial Light and Magic”
▶ Watch at ~53:00approx.
AtriumMentionscompany · Justin Kan
“Justin's second company Atrium most people thought that that made sense automating legal tasks”
▶ Watch at ~53:30approx.
WebflowMentionssoftware · Webflow
“this episode is brought to you by webflow”
▶ Watch at ~54:30approx.
Living CarbonMentionscompany
“the mdty hall example is really powerful because Maddie proactively got out of the present”
▶ Watch at ~59:00approx.
Ford F-150Mentionsproduct · Ford
“how does that compare to Ford F-150”
▶ Watch at ~1:02:30approx.
Tesla CybertruckMentionsproduct · Tesla
“nobody looks at the Tesla cyber truck and says oh yeah well how does that compare to Ford F-150”
▶ Watch at ~1:02:30approx.
TeslaMentionscompany · Tesla, Inc.
“Tesla's Mission says accelerate the world's transition to sustainable energy”
▶ Watch at ~1:09:30approx.
LinearMentionssoftware · Linear
“linear is kind of pushing this movement of craft and design and experience matters in B2B software”
▶ Watch at ~1:10:30approx.
Four Seasons Hotels and ResortsMentionscompany
“you can hang out the Four Seasons and it's going to be just like the Four Seasons everywhere else”
▶ Watch at ~1:11:00approx.
7 PowersMentionsbook · Hamilton Helmer
“counterposing from Hamilton Hamilton helmer's seven Powers book”
▶ Watch at ~1:12:00approx.
Star WarsMentionsfilm · George Lucas
“let's say Luke Skywalker on tatto weet Dusty Planet”
▶ Watch at ~1:12:30approx.
iPhoneMentionsproduct · Apple
“Nancy would show me how Steve Jobs's iPhone launch speech”
▶ Watch at ~1:17:30approx.
MicrosoftMentionscompany · Bill Gates and Paul Allen
“my dad worked for Bill Gates when he was at Microsoft”
▶ Watch at ~1:27:00approx.
Lenny's PodcastCoinedpodcast · Lenny Rachitsky
“Lenny's podcast and Lenny's blog and Lenny's newsletter”
▶ Watch at ~1:33:00approx.
Lenny's NewsletterCoinednewsletter · Lenny Rachitsky
“Lenny's podcast and Lenny's blog and Lenny's newsletter”
▶ Watch at ~1:33:00approx.
AppleMentionscompany · Steve Jobs, Steve Wozniak, and Ronald Wayne
“let's take a company like say apple when they did the iPhone”
▶ Watch at ~1:35:00approx.
Skunk WorksMentionscompany · Lockheed
“the other example I like is skunk orb with Lockheed”
▶ Watch at ~1:36:30approx.
LockheedMentionscompany
“the other example I like is skunk orb with Lockheed”
▶ Watch at ~1:36:30approx.
IBM PCMentionsproduct · IBM
“Don estrich at IBM when they did the IBM PC”
▶ Watch at ~1:37:00approx.
The Top Five Regrets of the DyingRecommendsbook · Bronnie Ware
“a book called The Five regrets of the dying”
▶ Watch at ~1:40:30approx.
ResonateRecommendsbook · Nancy Duarte
“Nancy gte's Book resonate would we talked about Nancy earlier I I like that book a lot”
▶ Watch at ~1:42:00approx.
AmazonUsescompany · Jeff Bezos
“I found it on Amazon as you're talking and I'm buying it”
▶ Watch at ~1:42:30approx.
Montblanc Meisterstück 149Recommendsproduct · Montblanc
“my favorite product of recent times is a this will go everybody will be like that sounds pretty esoteric but it's a Mont Blanc 149”
▶ Watch at ~1:43:30approx.
Pattern Breakers: Why Some Start-Ups Change the FutureRecommendsbook · Mike Maples, Jr. and Peter Ziebelman
“the book is called pattern Breakers why some startups change the future”
▶ Watch at ~1:48:30approx.
Apple PodcastsMentionssoftware · Apple Inc.
“you can subscribe to the show on Apple podcast Spotify or your favorite podcast app”
▶ Watch at ~1:48:30approx.
SpotifyMentionssoftware · Spotify
“you can subscribe to the show on Apple podcast Spotify or your favorite podcast app”
▶ Watch at ~1:48:30approx.

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Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Hot Take· 2

Hot Take12:00

Better Doesn't Matter — Be the World's First Banana

Maples argues that being 'better' is a trap for startups because better is just an extension of the present, and customers won't switch to a resource-poor startup that is merely a 10x improvement. Instead, founders should force a choice, not a comparison — offer something so different it can't be compared to incumbents. He frames it as refusing to sell a better apple and instead being the world's first banana.

'Better' assumes the future resembles the present, only slightly different
Startups win by being radically different and avoiding the comparison trap
A customer with any alternative won't be desperate enough to do business with a startup
Force a choice, not a comparison
Don't waste time on people who love apples — find the people who value bananas

“better doesn't matter when you're a startup because better is an extension of the present better is when you think the future future will resemble…”
Mike Maples Jr · 12:00

“if everybody's selling apples I can't be a 10 times better Apple I want to be the world's first banana”
Mike Maples Jr · 1:01:30

#positioning#differentiation#startup-strategy

Hot Take1:25:30

Great Founders Are the Right Kind of Disagreeable

Maples argues a startup is fundamentally a disagreeable act, and he's wary of 'coachable' founders. He recounts that with Ev Williams his whole job was to give advice that got ignored — and that was fine, because Ev listened, understood, and then believed a different truth. He points to Bill Gates and Elon Musk as hard-driving leaders whose high standards, not warmth, earned deep respect.

A startup is a fundamentally disagreeable act — disagreement with how things are done
Maples is skeptical of prizing 'coachable' founders
With Ev Williams, his job was 'to give him advice that he ignored'
The right kind of disagreeable founder listens, understands, then still backs their own truth
Bill Gates and Elon Musk earned respect through high standards, not warmth

“when I would meet with EV Williams my whole job was to give him advice that he ignored”
Mike Maples Jr · 1:25:30

“great people are inspired by hard asses as long as the hard ass like makes this you know you you meld the steel In the…”
Mike Maples Jr · 1:27:30

#disagreeableness#founders#leadership#coachability

Explainer· 2

Explainer25:00

The Three Kinds of Inflections: Tech, Regulatory, and Belief

Maples explains that an inflection is an external event that creates potential for radical change — not an improvement curve like Moore's Law. He distinguishes three types: technological (iPhone 4S GPS chip enabling Lyft), regulatory (COVID legalizing cross-state telemedicine), and belief/attitude changes (people permanently accepting telemedicine and remote work). At a macro level it collapses to two forces: technology changing enablement and people changing their behavior.

An inflection is a turning point, not a gradual improvement curve — Moore's Law is not an inflection
Technological example: iPhone 4S GPS chip made Lyft possible
Regulatory example: COVID made cross-state telemedicine legal and reimbursable
Belief example: people permanently changed their attitude toward telemedicine and remote work
Macro view: it's technology changing enablement or people changing beliefs/behavior

“an inflection is an external event that creates the potential for radical change in how people think feel and act”
Mike Maples Jr · 15:30

“in no event was that a technology change right that was a regulatory change that allowed technology to be empowering in new ways”
Mike Maples Jr · 25:30

#inflections#timing#why-now

Explainer41:00

Earned Secrets Come From Getting Your Hands Dirty in the Future

Maples rejects the idea that visionaries have special binoculars to see farther. Instead, inventions happen when people get their hands dirty at the cutting edge and notice what's missing. He invokes William Gibson — the future is already here, just unevenly distributed — and argues you earn secrets by tinkering and being awake to what most people walk right past.

Vision isn't seeing farther — it's earning secrets by getting your hands dirty
You notice what's missing in the future because you're living in it
William Gibson: the future is already here, just not evenly distributed
Great founders tune their 'noticing filter' to Volume 11
Most people pass secrets by because they're looking to validate what they already believe

“the way the way inventions happen is people get their hands dirty and they they they learn about what's missing in the future”
Mike Maples Jr · 41:30

“William Gibson was right you know when he said um the future is already here it's just not evenly distributed”
Mike Maples Jr · 56:00

#earned-secrets#vision#cutting-edge#insight

Story· 5

Story03:30

How Forgetting He Owned Twitch Sparked the Research

Mike Maples recounts that when Amazon acquired Twitch for $970M, he had forgotten he was even a shareholder because the company had morphed out of Justin TV. Reviewing a decade of investing, he realized about 80% of his exit profits came from pivots, and that his best-performing teams often ignored the standard startup best practices. This unsettling pattern became the genesis of his book research.

Twitch sold to Amazon for $970M and Floodgate made ~85x its money
Maples had forgotten he was a shareholder because Justin TV had morphed into Social Cam and Twitch
~80% of his exit profits came from pivots, not the original idea
Companies that did all the 'right things' (business model canvas, customer development) often failed
The winners were often 'crazy and wild and random'

“twitch was acquired by Amazon for 970 million and we made something like 85 times our money and normally you'd think that's a really good…”
Mike Maples Jr · 03:30

“I noticed that like 80% of my exit profits had come from pivots”
Mike Maples Jr · 04:00

#pivots#investing#twitch#startup-lessons

Story32:30

Passing on Airbnb in a Room Full of Cereal Boxes

Maples tells the story of meeting Brian Chesky before Airbnb applied to Y Combinator: a discombobulated pitch in a room full of cereal boxes, a demo that wouldn't work, and slides Chesky wouldn't show. He and his partner passed, partly spooked by 'stay in a stranger's house' fears around the Craigslist-killings era. He estimates he was offered the deal at a $1.5M valuation and would have made ~6,000x his money.

Chesky was introduced by Michael Seibel before Airbnb applied to YC
The meeting was chaotic — cereal boxes everywhere and a demo that wouldn't work
Maples and his partner thought nobody would stay in a stranger's house
He was offered a chance to invest at a ~$1.5M valuation
The pass would have been a ~6,000x miss

“the meeting was totally discombobulated right so a room full of cereal boxes I'm like what's up with this why is there cereal here”
Mike Maples Jr · 33:00

“I would have made like 6,000 times my money or something like that”
Mike Maples Jr · 36:00

#airbnb#missed-deals#pitching#investing

Story37:30

Chegg's Fake Site That Revealed Students Would Pay Double

Maples describes how Chegg's founders tested demand with a fake site, 'textbook flick,' that 404'd at checkout. Crucially, instead of only testing one price, they tested an arbitrary range up to $75. The surprise: students who they assumed would only pay $35 to rent a $100 textbook were willing to pay $75 — a finding that would have been invisible in a simple validation experiment.

They built a fake site (textbook flick) that gave a 404 error at checkout
They tested a range of prices up to $75, not just one price point
Students were willing to pay far more ($75) than the assumed $35
A validation-only experiment would have missed the real pricing power
Good experiments are designed to surprise you, not confirm your hypothesis

“textbook flick wasn't a real site so you'd get to the shopping cart it would give you a 404 error but we could tell that…”
Mike Maples Jr · 39:30

#experiments#pricing#chegg#demand-testing

Story38:00

Scott Cook's Question: What Were Your Three Biggest Surprises?

Maples shares a lesson from Intuit founder Scott Cook, who would ask people presenting a new product to name their three biggest surprises. Often they couldn't name any — a sign they were 'brain locked' on their own agenda and seeking validation rather than truth. Authentic truth-seekers treat surprise as a gift because it means they may have discovered something no one else has.

Scott Cook asked product teams to name their three biggest surprises
Inability to name surprises signals agenda-driven validation, not truth-seeking
Surprise is a gift — it may mean you've discovered something new
Design experiments so you're in a position to be surprised

“he would say what were your three biggest surprises as you were coming up with this plan and what he would find is quite often…”
Mike Maples Jr · 38:00

“when people can't name the surprises they came up with they're too brain locked on what they want”
Mike Maples Jr · 38:30

#surprises#truth-seeking#product#scott-cook

Story57:00

How Maddie Hall Moved Into the Future by Shadowing Sam Altman

Maples uses Maddie Hall, founder of Living Carbon, to show how someone without a supercomputer lab can 'get out of the present.' Her early startup ideas (laser tag, etc.) weren't good, so she spent a year as Sam Altman's chief of staff — because Altman visits the future multiple times a day. That exposure led her to marry the inflection of maturing genetic-engineering tech with the coming demand for carbon capture.

Maddie Hall's early startup ideas were weak (a laser tag idea, others)
She spent a year as Sam Altman's chief of staff to be near the future
She spotted Microsoft and others about to spend heavily on carbon capture
She married the genetic-engineering inflection with that need to found Living Carbon
You can intentionally get out of the present by sampling many futures

“she decided to go follow Sam Alman for a year to be his chief of staff and Sam Alman visits the future multiple times a…”
Mike Maples Jr · 57:30

#living-in-the-future#living-carbon#sam-altman#idea-generation

Tool· 1

Tool1:40:30

Mike Maples' Most-Recommended Books

In the lightning round, Maples names the books he recommends most. He cites 'The Top Five Regrets of the Dying' by Bronnie Ware (a hospice nurse) for reminding you what matters, and 'Chase, Chance, and Creativity' by James Austin for its idea that luck is created, not given. He also mentions Clayton Christensen's books, Robert Greene's 'The Laws of Human Nature,' and Nancy Duarte's 'Resonate.'

'The Top Five Regrets of the Dying' by Bronnie Ware — a hospice nurse's account of what people wish they'd done
'Chase, Chance, and Creativity' by James Austin — how some people attract and create luck
Anything by Clayton Christensen
'The Laws of Human Nature' by Robert Greene
'Resonate' by Nancy Duarte

“A book called The Five regrets of the dying top five regret of the Dying by bronny where she was a hospice nurse”
Mike Maples Jr · 1:40:30

“There's another book that that I really like called uh Chase chance and creativity by a guy named James Austin”
Mike Maples Jr · 1:41:00

#books#recommendations#reading-list

Takeaway· 2

Takeaway36:30

As a Founder You Only Have to Be Right Once

Maples notes that his stage of investing only requires a couple of bets to work out to win, and the same asymmetry applies to founders. You don't need to be right repeatedly — a single breakthrough is enough. This reframes the fear of failure into permission to take bold, non-consensus swings.

Early-stage investing needs only a couple of winners to succeed
The same is true for founders — you only have to be right once
This asymmetry gives permission to make bold, potentially wrong bets

“if if you do this right you only have to be right once right and so that's that's really important”
Mike Maples Jr · 36:30

#risk#founders#investing

Takeaway1:44:30

'Do Your Best' — The Life Motto From His Father

Maples shares the life motto he learned from his dad: do your best. It doesn't mean be the best — it means life is a gift, every day is the gift of your time, and the way to honor it is to do your best. He recalls slacking on a high-school English test after getting into Stanford, and his dad's disappointment teaching him that people who achieve greatness treat everything as counting.

'Do your best' means honoring the gift of your time, not being the best
You won't always be the best, but doing your best is all you can do
As a senior he blew off a test he could drop; his dad's disappointment stuck with him
People who achieve greatness think everything counts
Compare yourself to the idea of perfection, not to other people

“it sounds simple but it's kind of profound do your best”
Mike Maples Jr · 1:44:30

“the people who achieve greatness they think everything counts”
Mike Maples Jr · 1:45:30

#life-lessons#motto#mindset#personal

Key ideas

Frameworks in this episode

Earn the Secret by Savoring Surprises

Force a Choice, Not a Comparison

Live in the Future and Notice What's Missing

Pattern-Breaking Inside a Big Company

The Inflection Stress Test

The Three Elements of a Breakthrough Idea

The Three Pattern-Breaking Actions

The Three-Slide Believer Pitch

People & resources mentioned

People · 25

Resources · 56

Insights & moments

◆Hot Take· 2

Better Doesn't Matter — Be the World's First Banana

Great Founders Are the Right Kind of Disagreeable

✶Explainer· 2

The Three Kinds of Inflections: Tech, Regulatory, and Belief

Earned Secrets Come From Getting Your Hands Dirty in the Future

❝Story· 5

How Forgetting He Owned Twitch Sparked the Research

Passing on Airbnb in a Room Full of Cereal Boxes

Chegg's Fake Site That Revealed Students Would Pay Double

Scott Cook's Question: What Were Your Three Biggest Surprises?

How Maddie Hall Moved Into the Future by Shadowing Sam Altman

✦Tool· 1

Mike Maples' Most-Recommended Books

▲Takeaway· 2

As a Founder You Only Have to Be Right Once

'Do Your Best' — The Life Motto From His Father

Hot Take· 2

Explainer· 2

Story· 5

Tool· 1

Takeaway· 2