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Starting a Company in a Space You’re Not an Expert in — This Founder Shares 6 Lessons
Starting Up

Starting a Company in a Space You’re Not an Expert in — This Founder Shares 6 Lessons

From the importance of founder naivety, to seeking out the doubters, to rigorously assessing founder/market fit, Irving Fain shares his lessons from building a company in a space he wasn't an expert in, as well as other takeaways from the earliest days at his startup, Bowery Farming.

Ask Why It Won’t Work, And Other Lessons This Founder Relies on While Building From 0 to 1
Starting Up

Ask Why It Won’t Work, And Other Lessons This Founder Relies on While Building From 0 to 1

From all the ways a candidate might fail, to how a commonly-used framework might not be a good fit, to where a go-to-market strategy might fall apart, Rick Song shares the pre-mortem technique he relies on, as well as other company building lessons from Square and his startup, Persona.

Hiring a VP of Engineering? Use This Framework from Shopify’s VPE to Get it Right
Engineering

Hiring a VP of Engineering? Use This Framework from Shopify’s VPE to Get it Right

After more than 20 years in tech, eight companies, and thousands of hires, Shopify's Farhan Thawar shares his go-to-framework for snagging a VP of Engineering. From the skills that are most important to the questions to ask and red flags to watch out for, his advice will help founders dive several l

Counterintuitive Lessons on How to Get Better as You Scale, From Twilio’s Jeff Lawson
Starting Up

Counterintuitive Lessons on How to Get Better as You Scale, From Twilio’s Jeff Lawson

13 years after Twilio first launched, CEO and co-founder Jeff Lawson opens up about the peaks and valleys to share a set of unconventional company building lessons on how to get better as you scale — from introducing new products and refining go-to-market strategies to focusing annual planning.

Between Sales and Product: Building Out Self-Serve and Customer Experience at Notion & Dropbox
Sales

Between Sales and Product: Building Out Self-Serve and Customer Experience at Notion & Dropbox

Kate Taylor spent 8 years at Dropbox leading their SMB revenue and scaled sales operation) and is now the Head of Customer Experience at Notion.

3 Rules for Building a More Caring Culture — This Chief People Officer Shares Lessons from Lambda School & InVision
People & Culture

3 Rules for Building a More Caring Culture — This Chief People Officer Shares Lessons from Lambda School & InVision

Mark Frein has served as Chief People Officer at Return Path, InVision, and now Lambda School. Here, he shares his approach to spinning up the people function, as well as tactical tips for creating a great employee experience, enabling a workforce that feels seen and heard, and making an environment

Joining a Startup for the First Time? 30 Actionable Tips From Folks Who've Been There
People & Culture

Joining a Startup for the First Time? 30 Actionable Tips From Folks Who've Been There

Top startup leaders and operators share their best tips for new startup employees, including hitting the ground running, how to prioritize what to work on, and growing your career.

Following “Radical Candor,” Kim Scott is Back with Another Incredible Framework for “Just Work”
Management

Following “Radical Candor,” Kim Scott is Back with Another Incredible Framework for “Just Work”

"Radical Candor" bestselling author Kim Scott's superpower is outlining simple tactics and straightforward frameworks to put big amorphous ideas into practice. In her latest book, "Just Work," she applies that tactical lens to workplace injustice.

The Engineering Leader’s Guide to Crafting a Personal Brand that Stands Out From the Crowd
Engineering

The Engineering Leader’s Guide to Crafting a Personal Brand that Stands Out From the Crowd

As an Engineering Leader at Help Scout, Anjuan Simmons has carved out a robust side hustle as a public speaker and blogger. Here, he shares his playbook for engineers to get started with personal branding and stand out from the crowd.

This GTM-Leader-Turned-Investor Crowdsources Early Lessons From Stripe, Figma & More
Sales

This GTM-Leader-Turned-Investor Crowdsources Early Lessons From Stripe, Figma & More

As he makes the transition from operator to investor, Meka Asonye looks back on his career as a sales leader at Stripe and Mixpanel to offer tactical takeaways and go-to-market lessons — crowdsourcing additional advice from the top revenue leaders in his network.

Focus on Your First 10 Systems, Not Just Your First 10 Hires — This Chief of Staff Shares His Playbook
Management

Focus on Your First 10 Systems, Not Just Your First 10 Hires — This Chief of Staff Shares His Playbook

As Chief of Staff at HashiCorp, Kevin Fishner focuses on treating the company like a product. Here, he unpacks why the systems side of company building doesn’t get as much attention and digs into the nitty-gritty details of how they set and track progress toward goals.

Making Self-Care Tactical — Why You Should Focus on Boundaries, Not Just Bubble Baths
Management

Making Self-Care Tactical — Why You Should Focus on Boundaries, Not Just Bubble Baths

Therapist Jessmina Archbold (publicly known as Minaa B.) shares her detailed guide to deeper self-care work, pushing back against common myths, offering up tactical advice and making the case for focusing on boundaries.

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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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