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20 Lessons From 20 Different Paths to Product-Market Fit — Advice for Founders, From Founders
Product

20 Lessons From 20 Different Paths to Product-Market Fit — Advice for Founders, From Founders

After more than a year of showcasing dozens of founders in our Paths to PMF series, we pulled together a list of the biggest lessons that stuck with us from these winding startup journeys.
How Notion Does Marketing: A Deep-Dive Into its Community, Influencers & Growth Playbooks
PR & Marketing

How Notion Does Marketing: A Deep-Dive Into its Community, Influencers & Growth Playbooks

We peel back the layers of Notion’s multifaceted marketing strategy, diving deep into three distinct channels that have helped power its meteoric rise: community, influencer marketing, and growth and analytics.
Take Two: Eight Hard-Earned Lessons from Repeat Founders on Starting Over Again
Must-reads

Take Two: Eight Hard-Earned Lessons from Repeat Founders on Starting Over Again

There's plenty of advice for first-time founders, but fewer resources for those embarking on their second or subsequent venture. To help navigate these, we gathered insights from experienced serial founders, distilling eight tactical lessons they applied differently the second time around.
The Not So Cookie-Cutter Approach to Company Building — 8 Lessons from Zapier
Starting Up

The Not So Cookie-Cutter Approach to Company Building — 8 Lessons from Zapier

Wade Foster, founder and CEO of Zapier, shares his contrarian takes on building a billion-dollar company — from fundraising advice, go-to-market strategy, and hiring mistakes.
Build Your Culture Like a Product — Lessons from Asana’s Head of People
People & Culture

Build Your Culture Like a Product — Lessons from Asana’s Head of People

Anna Binder, Asana's Head of People and the company's first HR hire, shares her step-by-step approach to intentionally building the company culture.
Navigating the Legal Maze: A Founder’s Guide to Hiring Lawyers at Every Stage of Your Startup
Starting Up

Navigating the Legal Maze: A Founder’s Guide to Hiring Lawyers at Every Stage of Your Startup

Veteran legal executive Irene Liu provides a comprehensive guide on the startup legal roadmap and how to engage lawyers as you scale. She offers insider advice on hiring outside and in-house counsel and building strong founder-lawyer partnerships.
Navigating New Waters: 10 Tips for First-Time Founder Success
Must-reads

Navigating New Waters: 10 Tips for First-Time Founder Success

Tactical advice from seasoned founders like Thumbtack’s Marco Zappacosta and Dropbox’s Drew Houston about the biggest mistakes to avoid as a first-time startup founder.
How to Know if Your Idea’s the Right One — A Founder’s Guide for Successful Early-Stage Customer Discovery
Starting Up

How to Know if Your Idea’s the Right One — A Founder’s Guide for Successful Early-Stage Customer Discovery

Jeanette Mellinger, BetterUp's Head of UXR and former Head of UXR for Uber Eats, unpacks her approachable three-step playbook for early-stage customer discovery so founders can build something users really want.
GOAT’s Path to Product-Market Fit — How a Fake Sneaker Sparked a $4B Idea
Product

GOAT’s Path to Product-Market Fit — How a Fake Sneaker Sparked a $4B Idea

GOAT co-founder and CEO Eddy Lu sits down with First Round Partner Todd Jackson to tell the story of how a decade of middling entrepreneurial ideas finally culminated in the $4B idea for a sneaker marketplace.
From Flagship Back to Fledgling: Lessons on Going Multi-Product From an Early Stripe PM
Product

From Flagship Back to Fledgling: Lessons on Going Multi-Product From an Early Stripe PM

In this exclusive interview, Tara Seshan shares nine lessons from her playbooks for going multi-product, drawing on examples from both Stripe and Watershed.
Add More Rigor to Your Reference Calls With These 25 Questions
Management

Add More Rigor to Your Reference Calls With These 25 Questions

When approached with craft and care, reference calls can be a massively influential piece of the hiring decision.
Vercel’s Path to Product-Market Fit — From Open-Source Project to Billion-Dollar Business
Product

Vercel’s Path to Product-Market Fit — From Open-Source Project to Billion-Dollar Business

Guillermo Rauch, raised in Buenos Aires and fascinated by computers since age 7, taught himself to code and moved to San Francisco at 18. His company, Vercel — the frontend cloud service behind open-source development framework Next.js — was recently valued at $2.5 billion.
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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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