In Depth

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 conversation, the path required a dramatic pivot. Here’s a preview of what Deepak shares: The emotional journey of how the pandemic forced them to abandon the initial idea for a personal loan product. How the team validated demand for the new idea by focusing on the launch announcement and getting all of the branding exactly right — before building anything. The launch strategy that crashed X1’s website and built up a 600K long waitlist. . Why finding product-market fit is different for consumer companies, plus advice on fundraising in tough times. Whether you’re in the early innings of starting a company, going through a tough pivot yourself, or planning out your product’s launch there are tons of helpful tactics here.You can follow Deepak on Twitter at @drao1. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @tjack.

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 catalysts don't just create change by pushing harder or exerting more energy — they remove or lower the barriers to change. (In the book Jonah offers a helpful framework about 5 specific barriers to change, called REDUCE — which stands for reactance, endowment, distance, uncertainty, and corroborating evidence.)We focus on how founders and leaders can do that in the context of building and selling products. Jonah shares his thoughts on: Whether you truly need to build a 10X better product and why a startup’s biggest competitor is actually inertia.  The role of urgency in selling or getting someone to adopt a product. How to apply the freemium approach in different contexts, like with physical products. Techniques for negotiating price, as well as the role that identity and category creation play in persuasion and product adoption. You can follow Jonah on Twitter at @j1berger. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. 

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 days. He discusses why plenty of smart folks thought the idea for Retool would fail and that the product’s developer focus would sink the company.We explore why David had such strong conviction in his target customer, even in the face of doubters, and his early lessons on finding language-market fit. David also explains how Retool nabbed its earliest customers (which includes Brex, DoorDash and a Fortune 500 BigCo) and shares his playbook for creating incredibly tight feedback cycles with these early evangelists.On the surface, Retool’s path to product-market fit seems incredibly smooth. But as David tells it, there were plenty of bumps in the road — and he’s got tons of advice for early-stage founders that are finding their footing.

Rich Rao, VP of the Small Business Group at Meta, shares insights from his extensive background at Google and Meta. He discusses how his engineering perspective shapes go-to-market strategies, highlighting structured product roadmaps and the importance of creativity in marketing. Rao reflects on the early days of Gmail at Google, detailing critical pricing lessons and the challenges of moving from free trials. He also emphasizes the value of partnerships and engaging early adopters for successful product launches.

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 like Twilio and Salesforce craft a corporate message from the ground up, and tweak it as the company grows. She also shares specific advice for marketers with sights on the CMO seat, including how to form collaborative, not combative relationships with sales counterparts.You can follow Sara on Twitter at @SaraVarniBrightYou can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

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 days, and how they navigated the journey of finding traction and scaling. As you’ll hear in the episode, the Alma team essentially had to find product-market fit twice as they went from physical, co-working office spaces pre-pandemic, to quickly building out their virtual care capabilities.Here’s a preview of what Todd and Harry cover: Approaching team building as a solo founder Refining the idea and getting more insights from your customers through structured interviews, using the technique doctors are trained on Rallying your team through a pivot Staying competitor aware — not competitor obsessed The difference between building a marketplace versus a platform. Whether you’re in the early stages of starting a company or going through a tough pivot, there are tons of helpful tactics here.You can follow Harry on Twitter at @harryritter1. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @tjack.

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 history is marked by success stories of founders who refused to quit, even when just about every signal was telling them to do so.But Annie offers a counterintuitive approach. She dives into all the misconceptions about quitting, and makes the case that it can actually be a superpower, rather than a weakness. Annie explores the psychology behind why it’s so hard to walk away, and tactically what folks can do to get a clearer picture of the decisions ahead of them, rather than being clouded by biases. She also offers specific advice for advice-givers who are trying to nudge someone to change course, with tested tips for getting your message across gently, yet firmly.And after the episode be sure to check out “Quit: The Power of Knowing When to Walk Away.”You can follow Annie on Twitter at @AnnieDuke.You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

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 writing a line of code. Their rituals for spending valuable time together as the company grows, including thought-starter questions for deep discussions and sharing an executive coach. How they run the executive team at scale and sketch out decision rights. Manu and Brian both have extremely valuable advice to other founders, either those in the early stages of looking for a co-founder, or folks who want to add a little magic to an existing co-founding relationship.You can follow Manu at @manuaero and Brian at @RiegerB on Twitter.You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

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 specific feedback.  The most impactful questions that founders and customer success managers should ask all their customers. Why everyone at the company owns the net revenue retention metric — not just the customer success function. How to make your first customer success hire, from the ideal profile to structuring the interview process and setting comp.  You can follow Sydney on Twitter at @sydneystrader. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.

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 recruiters makes Steven the perfect person to talk to about early-stage recruiting.In our conversation we focus on how to make those fourth, fifth, or tenth hires — those really early days when your startup has zero brand recognition or recruiting help. Here’s a preview of his tactical advice: A trick for sourcing second-degree network connections The power of sending a “break-up” message in your candidate outreach.  How Gem brought candidates on to work with them in very structured trial periods before making a full-time offer.  Advice for working on your recruiting pitch and nurturing passive talent The similarities between early-stage hiring and founder-led sales You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson