In Depth

Our guest today is Daniel Debow, a VP of Product for Demand at Shopify.  Daniel is a three-time founder and a seasoned M&A pro. Daniel oversaw the process of all three of his companies’ acquisitions and has helped continue to grow them at scale inside larger corporations. His most recent startup, Helpful, was acquired by Shopify in 2019. Before that, he co-founded Rypple which was acquired by Sale...

Our guest is Anna Binder, Head of People at Asana. We go back to the earliest days when Anna first took on the role, starting with how she prioritized the initial things to tackle as a new People exec and combing through a slew of opinions that bubbled up from other folks at the company.  Next, she shares her tactical playbook for creating a culture of feedback for not just low-performers, but hig...

For our first episode of 2023, our guest is Mike Boufford, CTO of Greenhouse, an applicant tracking system and recruiting platform.  Mike has a unique career as an engineering leader. He wrote the first line of code at Greenhouse in May 2012, and he’s still there — over a decade later. This isn’t the typical path of non-co-founding engineers, who usually get layered or leave to start their own ven...

Our guest is Peter Kazanjy, co-founder of Atrium and author of “Founding Sales: The Early Stage Go-to-Market Handbook.” As an early-stage founder, there’s something comforting about the build stage. You’re tinkering with the nascent product, honing your MVP and dreaming up the possibilities of how much folks are going to love what you create. But once you get out of that comfort zone of quietly bu...

Todd Jackson is back on the mic to guest host another product-market fit focused episode this week. He chats with Deepak Rao, co-founder and CEO of X1, a consumer fintech startup that’s building a credit card for a new generation.  Just last week, X1 announced a $15 million funding round. But we’re here to rewind the clock and unpack how the startup got to this point. As you’ll hear in today’s con...

Our guest today is Jonah Berger, a marketing professor at the Wharton School at the University of Pennsylvania and the bestselling author of “Contagious” and “Invisible Influence.”  Today we’re chatting about his follow-up book, “The Catalyst: How to Change Anyone’s Mind.” Founders start companies to change industries and behaviors, but change is hard. Going back to chemistry, Jonah notes that cat...

Todd Jackson is back on the mic to guest host another product-focused episode this week. He chats with David Hsu, founder and CEO of Retool, a low-code platform for developers building custom internal tools. Today, Retool is valued at over $3 billion and has some of the biggest companies in the world building apps on its platform. But in this conversation, David rewinds the clock to Retool’s early...

Our guest is Rich Rao, the VP of the Small Business Group at Meta, where he manages the global revenue and operations for properties including Facebook, Instagram and WhatsApp. He also spent 10 years at Google, where he held a bunch of different go-to-market roles at the company, eventually becoming the GM for the Devices and Education verticals. In today’s conversation, Rich shares how his engine...

Our guest is Sara Varni, CMO of Attentive, a conversational commerce platform. Before joining Attentive, Sara was Twilio’s CMO and spent 10 years as a senior marketing leader at Salesforce. In today’s conversation, we talk about what startups can learn from enterprise marketing playbooks, particularly around creating and honing a corporate message. Sara takes us behind the scenes at how companies...

Todd Jackson’s back on the mic this week. (As a reminder, he’s guest hosting a few product-focused episodes this season — all about finding product-market fit.) Today, Todd chats with Harry Ritter, founder of Alma, a membership-based network that helps independent mental health care providers accept insurance and build thriving private practices. In our conversation, we go deep into Alma’s early d...

Our guest is Annie Duke, a retired pro poker player and First Round’s Special Partner focused on Decision Science. She’s also the author of the bestselling book, “Thinking in Bets.” In today’s conversation, we’re talking about her follow-up to that book, titled “Quit: The Power of Knowing When to Walk Away,” which was just released this week. Quitting is not a popular topic in startup circles and...

Our guests are Manu Sharma and Brian Rieger, co-founders of Labelbox. In this interview, we take a microscope to their co-founder DNA, exploring the ins and outs of how they’ve made the relationship work over the years. We discuss: How Manu and Brian came together as co-founders and landed on the idea for Labelbox. How they intentionally aligned their skillsets, values and responsibilities before...

Today’s episode is with Sydney Strader, VP of Customer Success at Catalyst. Prior to joining Catalyst, Sydney was the VP of Customer Success at InVision. In our conversation we focus on founder-led customer success, an area of early company building that’s often overlooked. Here’s a preview of her tactical advice: How to structure early customer check-ins, plus a framework to help surface more spe...

Today’s episode is with Steven Bartel, co-founder and CEO of Gem. Before building the talent acquisition platform, Steven was an early engineer at Dropbox, where he spent 5 years working on analytics, Dropbox Paper, and hiring as the company grew from 25 to 1500 people. This experience from Dropbox, combined with his lessons from building out Gem’s own team and talking to his customer base of recr...

Today’s episode is with Snir Kodesh, Head of Engineering at Retool, which is a development platform for building custom business tools. Before joining Retool, Snir spent six years as a Senior Director of Engineering at Lyft. In our conversation, we cover some of the biggest differences between leading engineering teams for a consumer product versus an enterprise platform — and the things that are...

Today’s episode is with Claire Butler, Senior Director of Marketing at Figma, and one of the company’s first 10 employees. In today’s conversation, she sketches out Figma’s five phases of community-led growth — and shares tons of advice along the way for startups who also are looking to build an organic growth engine. In the first phase, Claire covers the biggest lessons from Figma’s years of stea...

Todd Jackson’s filling in as host again this week. (As a reminder, he’s hosting a few product-focused episodes this season — all about finding product-market fit.) Today, Todd chats with Andrew Ofstad, co-founder of Airtable. In our conversation, we go deep into Airtable’s early days, and how they navigated the journey of finding traction and scaling. Here’s a preview of what Todd and Andrew cover...

Today’s episode is with Ian Wong, co-founder and CTO of Opendoor. Before founding Opendoor, Ian was Square’s first data scientist, where he developed machine learning models and infrastructure for fraud detection. In today’s conversation, we cover his essential advice for how to integrate data science into your startup. As Ian puts it, in the early innings it might make sense for your startup to b...

Today’s episode is with Sidharth Kakkar, founder and CEO of Subscript, a subscription intelligence platform that empowers B2B SaaS leaders to better understand their revenue. (Read more about the company in this Techcrunch article.) Previously, he was the founder, CEO of Freckle, an education platform that grew to serve 10 million students and was acquired by Renaissance Learning in 2019. As a rep...

Our guest is Sara Clemens, most recently COO of Twitch and former COO of Pandora. In this interview, we explore the nuances of the COO role, which can vary drastically across different companies. We cover: The three main COO archetypes and which sorts of folks are best suited for those roles. The tactical elements of being a COO, including Sara’s advice for what good strategy actually looks like,...

For our 60th episode, we’re doing things a little bit differently — with a new guest host! Welcome to Todd Jackson, who’s filling in for Brett Berson this week. Todd is also a Partner at First Round, and the episodes he hosts will mostly focus on product, given his previous product roles, from the VP of Product & Design at Dropbox and Director of Product Management at Twitter, to being a PM at Fac...

Today’s episode is with Russ Laraway, a seasoned leader who's been at Google, Twitter, Candor Inc, Qualtrics, and is now the Chief People Officer for Goodwater Capital Since we last had Russ on the show, he’s written a new book, titled: “When They Win, You Win.” On today’s episode, we dive deep into the management frameworks and original research that Russ discusses in his book. He starts by point...

Today’s episode is with Nate Stewart, CPO of Cockroach Labs, the creator of database product CockroachDB. In today’s conversation, we cover his essential advice for building a highly-technical product. He sketches out how the Cockroach team decided on the specific use case for its database product. Nate explains the steps the team took to reach conviction on their go-forward plan — which meant say...

Today’s episode is with Phaedra Ellis-Lamkins, co-founder and CEO of Promise, a modern government payment solution. In today’s conversation, Phaedra explores the ins and outs of selling a product into government. Phaedra pulls back the curtain of how she and the Promise team tackle the extra-long sales cycles, navigate layers of subcontractors, and convince risk-averse decision-makers to take a ch...

Today’s episode is with Gagan Biyani, co-founder and CEO of Maven, a company that empowers the world’s experts to offer cohort-based courses directly to their audience. After being early at 3 startups that achieved over $1 million in run-rate in their first six months of going live, Gagan has learned some valuable lessons and seen a wide range of outcomes — from Udemy going on to IPO in 2021, to S...