All of our First-time founders articles

Starting Up

An Exact Breakdown of How One CEO Spent His First Two Years of Company-Building

Sam Corcos, co-founder & CEO of Levels, tracked exactly how he spent the two years since founding the company for a rare inside look at being a startup leader.

A look at one repeat founder’s frameworks for validating ideas — Pilot’s Waseem Daher

https://waseem.substack.com/ [email protected] twitter.com/firstround twitter.com/brettberson Waseem Daher: I like to ask three questions about a business that I'm evaluating, or an opportunity I'm evaluating, and this is principally geared towards like a business to business product, but I

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.

The story behind Slack’s marketing and the leap from marketer to CEO — Abstract’s Kelly Watkins

[email protected] twitter.com/firstround twitter.com/brettberson https://medium.com/hackernoon/how-to-hire-your-first-head-of-marketing-67c43dd2cd73 https://review.firstround.com/build-products-that-solve-real-problems-with-this-lightweight-jtbd-framework KELLY WATKINS Brett Berson: Well, thank you for joining us Kelly. Kelly Watkins: Thanks so much for having me, Brett. I'm stoked to be here. Brett Berson: So the

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

How Thumbtack CEO Marco Zappacosta Parses Through Mountains of Advice as a First-Time Founder

Today’s episode is with Marco Zappacosta, co-founder and CEO of Thumbtack. He’s spent the last 13 years building the company into a billion-dollar business  — and it’s his first and only job after graduating college.

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.

CEO Jeff Lawson Reflects on the Peaks and Valleys of Twilio’s Growth Story

Today’s episode is with Jeff Lawson, co-founder and CEO of Twilio. He’s spent the last 13 years building and running the company, including leading through a successful IPO in 2016.

Upstart just went public — CEO Dave Girouard shares why it isn’t a typical success story

Today’s episode is with Dave Girouard, the CEO and co-founder of Upstart, an AI-powered lending platform that recently went public. Before founding Upstart, Dave was President of Google Enterprise, and spent 8 years building Google's billion dollar cloud apps business.

Start with the story — Drift’s David Cancel on lessons he’s learned as a 5X founder

Today’s episode is with David Cancel. David has been a CEO and founder of multiple different companies throughout his career. He’s also been a software engineer, a serial CTO, and the Chief Product Officer at Hubspot, giving him a unique lens into company building and leadership at different levels.

Lessons from a first-time CEO — Steve El-Hage on learning everything the hard way

Given the high-stakes nature of every hire, interviewing chops are always in need of sharpening. We’ve spent the past few months reaching out to some of the most thoughtful company builders in our network to pose a simple question: What’s your favorite interview question to ask and why?

Design

The Ultimate Guide to the Founding Designer Role

We summarized the most tactical, honest pieces of advice from a group of design experts on what it really takes to be a startup's first design hire — from choosing the right startup to join to excelling in the role and growing your team.