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Everything in Business is About Fighting Entropy — Here’s How Rippling Does It
Management

Everything in Business is About Fighting Entropy — Here’s How Rippling Does It

Matt MacInnis, COO of Rippling, shares why most companies slow down as they scale, and his advice for how startup founders and executives can prevent it.
25 Hard Questions Every Founder Should Ask Themselves
Starting Up

25 Hard Questions Every Founder Should Ask Themselves

Startup founders share their go-to questions for taking a pulse check on everything from product strategy to co-founder relationships to their own decision making.
The Uncomfortable Truth: A 3X Founder's Guide to Intellectual Honesty
Starting Up

The Uncomfortable Truth: A 3X Founder's Guide to Intellectual Honesty

Crossbeam CEO and co-founder Bob Moore shares his tools for quashing biases in pursuit of the truth at every stage of company building.
How to Build a Billion-Dollar Marketplace — Do’s and Don’ts from the Growth Expert Behind Grubhub, Pinterest, and More
Product

How to Build a Billion-Dollar Marketplace — Do’s and Don’ts from the Growth Expert Behind Grubhub, Pinterest, and More

Casey Winters, the growth expert behind Grubhub, Pinterest & Eventbrite, shares proven strategies for scaling marketplaces from 0 to $1B.
Annual Planning Sucks — A CPO, CRO, CFO, and COO Share Advice on How to Make it Better
Management

Annual Planning Sucks — A CPO, CRO, CFO, and COO Share Advice on How to Make it Better

Four top execs reveal their annual planning secrets from Notion, Stripe, Vanta, Linear, Linktree and more. From addressing AI to adjusting org charts, this COO, CFO, CPO & CRO share insights so startups at any stage can build effective, realistic plans.
Replit’s Path to Product-Market Fit — The $1 Billion Side Project
Product

Replit’s Path to Product-Market Fit — The $1 Billion Side Project

Sometimes the signals of product-market fit are so strong, they can no longer be ignored. In the latest installment of our Paths to Product-Market Fit series, Amjad Masad takes us on Replit's unconventional journey from college side project to billion-dollar AI startup.
The Saboteurs That Threaten Innovation — And How to Handle Them
Starting Up

The Saboteurs That Threaten Innovation — And How to Handle Them

Steve Blank (of Lean Startup and Four Steps to the Epiphany fame) unpacks why innovators and founders should expect fierce battles from incumbents on the path to disruption.
Passing the Button-Clicker Test, and Other 0 to 1 Lessons from Lattice’s First Marketing Hire
PR & Marketing

Passing the Button-Clicker Test, and Other 0 to 1 Lessons from Lattice’s First Marketing Hire

The behind-the-scenes story of how Lattice built its marketing strategy from the ground up, as told by its third employee and first marketing hire, Alex Kracov.
Non-Obvious Signs of Early Startup Traction — And How to Spot Them
Starting Up

Non-Obvious Signs of Early Startup Traction — And How to Spot Them

We gathered the most surprising anecdotes from seasoned founders about when things clicked into place.
Why Startup Marketers Should Be Diagnosticians — Advice from OpenAI's and Stripe's First Marketing Hire
PR & Marketing

Why Startup Marketers Should Be Diagnosticians — Advice from OpenAI's and Stripe's First Marketing Hire

Krithika Muthukumar was the very first marketer at OpenAI and Stripe. Here, she unpacks what it takes to found and scale a marketing operation to build an enduring brand.
Gong’s Path to Product-Market Fit — Why This $7B Company Still Works With Design Partners
Product

Gong’s Path to Product-Market Fit — Why This $7B Company Still Works With Design Partners

Gong co-founder and CPO Eilon Reshef sits down with First Round partner Todd Jackson to unpack how he turned an early bet on AI into a multi-billion dollar category leader in revenue intelligence.
Here’s What You Can Really Expect When Pitching Your Seed-Stage Startup at a VC Partner Meeting
Starting Up

Here’s What You Can Really Expect When Pitching Your Seed-Stage Startup at a VC Partner Meeting

There isn't much advice to guide founders on navigating their first VC partner meeting. So First Round Partner and former founder Liz Wessel shares her playbook for seed-stage startups tackling one of fundraising's most opaque processes
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For the founder's notepad:
"If you personally want to grow as fast as your company, you have to give away your job every couple months." – Molly Graham
“Asking ‘Why can't this be done sooner?’ methodically, reliably and habitually can have a profound impact on the speed of your organization.” – Dave Girouard
“End every meeting or conversation with the feeling and optimism you’d like to have at the start of your next conversation with the person.” – Chris Fralic
“Focus is doing things with a clear intention. It doesn’t mean you charge single-minded toward a goal. It means you pay rapt and incremental attention to how you need to turn the rudder on a project.” – Fidji Simo
“It’s essential to grow with the company — rather than having the company grow around you.” – Cristina Cordova 
“You have to be impatient with shipping, but patient with your career.” – James Everingham
“‘I trust you, make the call’ might be the six most powerful words you can hear from a manager.” – Sean Twersky
“Your job as a CEO is to build fire departments, not put out fires.” – Sam Corcos 
“Can you say with confidence that each report would want to be on your team again? If you aren’t sure that the answer is yes, it’s probably no — much like how if you have to ask, ‘Am I in love?’ you’re probably not.” – Julie Zhuo 
“People can get addicted to yak shaving. An effective engineering generalist knows when to move on. Pay attention to whether they used their time wisely, not just the results.” – Mike Krieger 
“It sounds so simple to say that bosses need to tell employees when they're screwing up. But it very rarely happens.” – Kim Scott
“You’ll know you understand the customer problem enough when you can predict 75% of what a customer tells you. Keep having these conversations until three-quarters of it is stuff you already know.” – Christina Cacioppo
“I have a rule: no company swag until the business has at least $250K of revenue or 250k users. Until then, you don’t get to “feel” the benefits of having started a company.” – Gagan Biyani
“The business model ends up becoming the business. It’s equally important as the market you’re going after and the product that you build.” – Jay Simons 
“If speed is the yin, the yang is prioritization. You can’t be fast if you don’t know what’s important.” – Jaleh Rezaei
“If you treat your connections as a kind of personal ATM you use for frequent withdrawals, you’ll quickly be disappointed (and overdrawn).” – Karen Wickre 
“Delighting the customer always yields better returns than countering or copying a competitor. It’s just a lot harder to do.” – Andy Rachleff 
“When you’re a founder, every moment you’re not writing code or getting users, you need to be making a conscious choice: Is whatever you’re doing worth your time?” – Alexis Ohanian
“‘Why would a customer not want this?’ is often a far more interesting question than why they would.” – Rick Song
“When you leave the planning process wondering if you put too many resources behind a single bet, that’s the bet that ends up succeeding. Bold ideas need bold resourcing.” – Lenny Rachitsky and Nels Gilbreth
“Treat customer development as a one-on-one with a direct report — you just want to ask the hard questions.” – Ryan Glasgow
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