Starting an education giant in a “bad market” | ClassDojo’s story | Sam Chaudhary (Co-founder and CEO)

Anil Varanasi is the co-founder and CEO of Meter, which provides full-stack networking infrastructure as a service for businesses. Since founding Meter with his brother Sunil in 2015, Anil has been playing a distinctly long game in one of the most entrenched markets in technology, betting on vertical integration, business model innovation, and a multi-decade time horizon. In this conversation, he unpacks Meter’s origin story, from four-plus years of heads-down R&D, and shares how his unconventional approach to planning, management, and pace keeps him excited to run the company for decades. In today’s episode, we discuss: Why Anil thinks in 25-year horizons How operating in a monopolistic market shaped Meter’s approach Why Meter scrapped a year of OS work during the R&D phase How Meter is rethinking networking’s business model Surviving COVID, Apple’s M1 transition, and “a thousand bad days” Anil’s contrarian views on planning, OKRs, and management How founders can build companies they’ll want to run for decades Where to find Anil: LinkedIn: https://www.linkedin.com/in/anilcv/ Twitter/X: https://x.com/acv Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast References: ADT: ⁠https://www.adt.com⁠ Alex Honnold: ⁠https://www.alexhonnold.com⁠ Alex Tabarrok: ⁠https://x.com/ATabarrok⁠ ⁠alarm.com⁠: ⁠https://www.alarm.com⁠ Andreessen Horowitz (a16z): ⁠https://a16z.com⁠ Apple: ⁠https://www.apple.com⁠ Bloomberg: ⁠https://www.bloomberg.com⁠ Bryan Caplan: ⁠http://www.bcaplan.com/⁠ Cisco: ⁠https://www.cisco.com⁠ Coca-Cola: ⁠https://www.coca-colacompany.com⁠ George Mason University (GMU): ⁠https://www.gmu.edu⁠ Intel: ⁠https://www.intel.com⁠ Julia Galef: ⁠https://x.com/juliagalef⁠ Martin Casado: ⁠https://www.linkedin.com/in/martincasado/⁠ Meraki: ⁠https://meraki.cisco.com⁠ Meter: ⁠https://www.meter.com⁠ Michela Giorcelli: ⁠https://x.com/M_Giorcelli⁠ Nicholas Bloom: ⁠https://www.linkedin.com/in/nick-bloom-stanford/⁠ Raffaella Sadun: ⁠https://www.linkedin.com/in/raffaella-sadun-3a182225/⁠ Sanjit Biswas: ⁠https://www.linkedin.com/in/sanjitbiswas/⁠ Sunil Varanasi: ⁠https://www.linkedin.com/in/sunil-varanasi-662a01253/⁠ Tyler Cowen: ⁠https://www.linkedin.com/in/tyler-cowen-166718/⁠ Twitch: ⁠https://www.twitch.tv⁠ Timestamps: (01:27) Meter’s unusual timeframes (04:06) “We don’t do OKRs” (06:32) How to plan without planning (08:31) Track your unhappy customers (11:43) How Meter’s journey began (15:02) Dissecting the 2010s SaaS boom (17:06) The networking industry trap (21:44) Meter’s first roadblock (22:07) Why Shenzhen accelerated Meter’s progress (26:29) The process to get a sales-ready product (31:02) Why you should own the full stack (32:45) The surprising thing you should innovate (35:03) Avoiding the one-trick pony trap (37:39) The secret to finding an excellent market (43:48) How COVID’s constraints propelled growth (48:25) Why founders need to know their customers (49:34) Why Meter didn’t sell via traditional channels (51:44) You need “seller-market fit” (54:51) The danger of meta-work (56:25) Decoupling management from authority (1:02:17) When the person is the problem (1:05:05) The inherent value of going slowly (1:09:41) Running a company for as long as possible

Jyoti Bansal is the co-founder and CEO of Harness, the software delivery platform used by thousands of engineering teams, and previously founded AppDynamics, which he led from inception to a multibillion-dollar acquisition by Cisco. In this episode, Jyoti unpacks what it really takes to move from mid-market to enterprise, why he thinks in terms of “product-market-sales fit,” and how he structures Harness as a collection of “startups within a startup” to launch multiple “best-of-breed” products. In today’s episode, we discuss: Why companies get stuck in the mid-market and struggle to move up into enterprise Why Jyoti deliberately lost Netflix as their customer The difference between product-market-sales fit, and product-market-fit How to build a scalable, capacity-driven go-to-market machine (instead of chasing deals) Diagnosing whether you have a product problem or a distribution problem How to hire and evaluate your first head of sales and top sales leaders Why Jyoti sold AppDynamics three days before IPO The “binary differentiator” rule for launching new products into crowded markets Why Harness runs 16 product lines under one roof Where to find Jyoti: LinkedIn: https://www.linkedin.com/in/jyotibansal/ Twitter/X: https://x.com/jyotibansalsf Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast References: Amazon: https://www.amazon.com/ AppDynamics: https://www.appdynamics.com/ Barclays: https://home.barclays/ BIG Labs: https://www.biglabs.com/ Carlos Delatorre: https://www.linkedin.com/in/cadelatorre/ Charles Schwab: https://www.schwab.com/ Cisco: https://www.cisco.com/ Citi: https://www.citi.com/ Cloudability: https://www.apptio.com/products/cloudability/ Datadog: https://www.datadoghq.com/ Dynatrace: https://www.dynatrace.com/ Harness: https://www.harness.io/ Jeff Bezos: https://x.com/JeffBezos Microsoft: https://www.microsoft.com/ Nasdaq: https://www.nasdaq.com/ Netflix: https://www.netflix.com/ New Relic: https://newrelic.com/ Salesforce: https://www.salesforce.com/ Splunk: https://www.splunk.com/ Traceable: https://www.traceable.ai/ Unusual Ventures: https://www.unusual.vc/ VMware: https://www.vmware.com/ Timestamps: (01:48) Why do companies get stuck in the mid-market? (05:09) Designing a product for enterprise and mid-market (07:19) Why Jyoti lost Netflix as a customer - on purpose (10:18) Becoming a scalable GTM organization (12:32) The real signs of product-market fit (14:04) Have you delivered the value? (15:46) How to hire your first sales team (19:59) The four signs of excellent sales leaders (23:16) How to interview a sales leader (27:51) Where Jyoti developed his commercial taste (29:37) Why early founders need to learn sales (32:02) How AppDynamics began (36:36) Why Jyoti sold three days pre-IPO (41:55) What does a healthy board look like? (44:23) How Jyoti perceives competition (46:18) Why you need a binary differentiator (49:53) How to launch multiple products (52:00) “We need to be best of breed” (57:38) Why PMs are like mini-entrepreneurs (1:00:20) The startup within a startup (1:02:45) A culture of continuous improvement

Zack Kanter is the founder and CEO of Stedi, an API-first healthcare clearinghouse. After bootstrapping a wildly profitable auto-parts business, he sold it to tackle "the most complicated problem" he'd ever encountered: business-to-business transaction exchange. He spent years building EDI infrastructure, threw away the entire codebase eight times, and found extraordinary traction in healthcare. Stedi recently raised a $70M Series B co-led by Stripe and Addition. In this conversation, Brett and Zack discuss why venture capital means "going pro," why execution is never actually a moat, and how "eating glass" became Stedi's competitive advantage. In today’s episode, we discuss: How 16-year-old Zack turned $2,500 into a wholesale empire Why bootstrapping means being "constrained by capital" and how VC removes that ceiling Why Zack rebuilt their EDI product eight times before launch The snake swallowing a deer: what extreme product-market fit really looks like What software companies can learn from discount retail and Toyota Why Stedi’s new hires are told "everything’s your fault now" And much more Where to find Zack: LinkedIn: https://www.linkedin.com/in/zkanter Twitter/X: https://x.com/zackkanter Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast References: Aetna: https://www.aetna.com/ Amazon: https://www.amazon.com/ AWS: https://aws.amazon.com/ Blue Cross Blue Shield: https://www.bcbs.com/ Change Healthcare: https://www.changehealthcare.com/ Cigna: https://www.cigna.com/ Clay: https://www.clay.com/ Costco: https://www.costco.com/ Ford Motor Company: https://www.ford.com/ GM: https://www.gm.com/ HIPAA overview (HHS): https://www.hhs.gov/hipaa/index.html Jeff Bezos: https://x.com/JeffBezos Kanban / TPS (Toyota): https://global.toyota/en/company/vision-and-philosophy/production-system Microsoft Teams: https://www.microsoft.com/microsoft-teams NetSuite: https://www.netsuite.com/ O’Reilly Auto Parts: https://www.oreillyauto.com/ Peter Thiel: https://x.com/peterthiel Porter’s five forces: https://www.isc.hbs.edu/strategy/pages/the-five-forces.aspx "Reality has a surprising amount of detail": https://johnsalvatier.org/blog/2017/reality-has-a-surprising-amount-of-detail Slack: https://slack.com/ Stedi: https://www.stedi.com/ Summit Racing: https://www.summitracing.com/ Target: https://www.target.com/ Walmart: https://www.walmart.com/ Zapier: https://zapier.com/ Timestamps: (01:24) Zack’s first business (08:54) Why the first customer is tricky (10:12) The downside of bootstrapping (11:42) Why venture capital is like “going pro” (14:20) The confusion between ownership vs. control (16:08) Building a company you don’t want to leave (20:46) Do things better than other people (24:49) Stedi’s early years (31:43) Physical vs. digital product-market fit (34:41) How Stedi scaled decision-making (40:08) Stedi’s journey to product-market fit (45:22) Finding founder-approach fit (50:42) “All software is a cascade of miracles” (52:52) The surprising lessons from discount retail (57:50) How the Toyota production system influences software (1:01:31) What it means to be a high-agency person (1:03:09) The core trait Zack looks for when hiring (1:02:57) Maintaining conviction in unconventional practice (1:14:19) When should you start to hire managers? (1:17:42) “Reality has a surprising amount of detail”

Jake is the founder and CEO of Serval, an AI-driven IT automation and service management platform that just raised $47M in Series A funding this week. Before founding Serval, Jake spent over five years at Verkada, where he led multiple products from 0-1 and helped scale the company across hardware and software. His years at Verkada taught him that winning in enterprise means delivering consumer-quality experiences to business buyers — a lesson that shapes how Serval turns complex IT automation into something that feels magical. In this episode, Jake and Brett dive into the lessons from Verkada that inspired Serval's founding, what it takes to disrupt entrenched enterprise categories, and practical tips for getting deeply embedded with customers and hiring high-quality candidates. In today’s episode, we discuss: Why building “in existing categories” can be more powerful than creating new ones The lessons from Verkada that shaped Serval's platform strategy The customer interview question that unlocked the IT buyer’s hidden pain points How Serval's automation builder uses AI to generate code-based workflows Redefining engineering and PM roles with forward-deployed engineers Keeping the hiring bar high in an AI-native startup Why there’s a “land grab” moment right now in enterprise AI And much more... Where to find Jake: LinkedIn: https://www.linkedin.com/in/jakestauch/ Twitter/X: https://x.com/jakeserval Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast References: Alex McLeod: https://www.linkedin.com/in/alexmcleodio/ Clay: https://www.clay.com Cloudflare: https://www.cloudflare.com Cursor: https://cursor.sh Filip Kaliszan: https://www.linkedin.com/in/kaliszan/ Hans Robertson: https://www.linkedin.com/in/hansrobertson Linear: https://linear.app Okta: https://www.okta.com Rippling: https://www.rippling.com Serval: https://www.serval.com/ ServiceNow: https://www.servicenow.com Verkada: https://www.verkada.com Workday: https://www.workday.com Timestamps: (02:25) Lessons from holding different product roles (07:29) Turning “hard mode” into a moat (10:49) The early days of Serval (12:59) Scratching the founder itch (14:57) Unconventional interview techniques (17:47) Solving core interview challenges (21:10) Planning the early product roadmap (23:03) The surprising power of patience (26:12) Serval’s impressive technical advantage (27:35) Disrupting legacy incumbents (31:13) Building for mid-market and enterprise (33:35) Serval’s enduring roadmap (36:08) How to sell to an existing market (39:16) The evolving role software plays (43:55) Building for AI that didn’t exist yet (49:49) Serval’s forward-deployed engineers (58:31) The hybrid PM-GM (1:00:27) “You can over-prioritize” (1:02:48) The unexpected value of panic buttons (1:04:50) What Serval looks for in new talent (1:07:01) The ultimate hiring litmus test (1:13:59) Building out Serval’s go-to-market function (1:16:31) The evolving IT market in 2025

Gorkem Yurtseven is the co-founder and CTO of fal, the generative media platform powering the next wave of image, video, and audio applications. In less than two years, fal has scaled from $2M to over $100M in ARR, serving over 2 million developers and more than 300 enterprises, including Adobe, Canva, and Shopify. In this conversation, Gorkem shares the inside story of fal's pivot into explosive growth, the technical and cultural philosophies driving its success, and his predictions for the future of AI-generated media. In today's episode, we discuss: How fal pivoted from data infrastructure to generative inference fal’s explosive year and how they scaled Why "generative media" is a greenfield new market fal's unique hiring philosophy and lean <50-person team Building a brand that resonates with developers What the world looks like in 2027 when AI-generated video becomes mainstream And much more… Where to find Gorkem: LinkedIn X / Twitter Where to find Todd: LinkedIn X / Twitter Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast References: Adobe: https://www.adobe.com/ Amazon: https://www.amazon.com/ Anthropic: https://www.anthropic.com/ Base10: https://base10.vc/ Black Forest Labs: https://blackforestlabs.ai/ Burkay Gur: https://www.linkedin.com/in/burkaygur/ Canva: https://www.canva.com/ Clay: https://www.clay.com/ Coinbase: https://www.coinbase.com/ Cursor: https://www.cursor.com/ DALL-E: https://openai.com/dall-e-2 Databricks: https://www.databricks.com/ Dylan Patel: https://www.linkedin.com/in/dylanpatelsa/ fal: https://fal.ai/ Google DeepMind: https://deepmind.google/ LLaMA: https://ai.meta.com/llama/ OpenAI: https://openai.com/ Oracle: https://www.oracle.com/ Perplexity: https://www.perplexity.ai/ Shopify: https://www.shopify.com/ Snowflake: https://www.snowflake.com/ Sora: https://openai.com/sora Stable Diffusion XL (SDXL): https://stability.ai/stable-diffusion Stability AI: https://stability.ai/ Together AI: https://www.together.ai/ All images and videos generated using models run on fal.ai Timestamps: (01:43) The generative media industry (02:29) From $2M to $100M ARR: fal's explosive year (04:06) How Gorkem met co-founder Burkay Gur (05:38) The hardest decision that saved the company (09:52) Spotting the opportunity in generative media (13:28) Turning Todd into George Clooney (15:29) The early adopters of the first fal product (17:54) The transition from toy to tool (19:27) Why 2025 is the year of AI-generated video (21:44) Staying nimble as a 45-person company (24:42) Predicting AI-generated film in 2027 (27:24) Why generative media is a greenfield market (30:33) fal’s greatest optimization wins (34:42) Why fal has 500 Slack channels (36:02) Competing in a fast-moving, fragmented market (42:06) How to build a world-class team (47:24) Learning sales as a technical founder (50:55) How fal built a brand without a marketer (53:21) The story behind "GPU Rich / GPU Poor" (54:22) Inside fal’s rule-breaking playbook (56:09) The hardest part of scaling fal

Michael is the co-founder and CEO of Prepared, the AI assistant for 911 calls that helps dispatchers capture information faster, translate emergency calls in real time, and deliver lifesaving context to first responders. Founded out of Yale in 2019, Prepared grew from a school safety app into a critical platform for emergency communications, disrupting a notoriously tough market. This mission-driven journey just reached a major milestone: Prepared was acquired by Axon, the global public safety technology company. In this conversation, Michael joins Meka to share the inside story of building in a tough market, the counterintuitive strategies used to crack government procurement, and why their mission is a competitive moat. In today’s episode, we discuss: Why school shootings were the catalyst for building safety software Navigating the most challenging customer base: government and public safety agencies Why Prepared gave away its first product for free — for years Lessons from evolving a wedge product into an AI-driven suite How Michael balanced conviction with customer feedback Building long-term investor relationships Staying true to the mission through headwinds and tailwinds And much more… Where to find Michael: LinkedIn: https://www.linkedin.com/in/michaelchime/ Where to find Meka: LinkedIn: https://www.linkedin.com/in/mekaasonye/ Twitter/X: https://x.com/bigmekastyle Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast References: Axon: https://www.axon.com/ Dylan Gleicher: https://www.linkedin.com/in/dylan-gleicher/ March for Our Lives: https://marchforourlives.org/ Neal Soni: https://www.linkedin.com/in/neal-soni/ OpenAI: https://openai.com/ Peter Thiel Fellowship: https://thielfellowship.org/ Prepared: https://www.prepared911.com/ Sam Altman: https://x.com/sama Slack: https://slack.com/ Uber Eats: https://www.ubereats.com/ Yale University: https://www.yale.edu/ Timestamps: (3:03) Staying mission-oriented under pressure (3:54) Negotiating an acquisition from a hospital bed (06:25) How Sandy Hook shaped the Prepared story (09:15) From school safety app to 911 platform (10:02) Why are 911 systems so outdated? (13:02) Prepared’s first product iteration (16:04) Why attempt to tackle the govtech market? (18:36) Mission as fuel: staying resilient through endless rejections (20:03) Should young people drop out of college? (23:10) How Michael nurtured a learner’s mindset (25:23) Forging unwavering founder conviction (31:41) Landing Prepared’s first user (32:39) “I want to be terrible at sales” (34:35) Expanding to a premium product line (36:55) Leveraging AI to expand the product surface area (41:49) How much should you listen to customers? (45:35) Building in headwinds vs. tailwinds (47:18) Navigating partnerships and competition (54:52) Michael’s unconventional approach to fundraising (1:02:54) Has Prepared found product-market fit? (1:04:00) Reflecting on the founder journey

Kiren Sekar is the CPO of Samsara, a company that brings real-time visibility, analytics, and AI to physical operations. Before Samsara, Kiren was an early leader at Meraki, which was acquired by Cisco for $1.2B. In this episode, he walks us through Samsara’s origin story: from hardware hacking in a basement to scaling a cross-industry IoT platform. He shares how early customer feedback loops led to the company’s first product, why starting with the mid-market was a deliberate choice, and how Samsara kept a startup mindset even as it scaled. In this episode, we discuss: Lessons from Meraki’s acquisition by Cisco How Kiren hires for intrinsic motivation Why Samsara was built for operations industries The early hardware prototype and the Cowgirl Creamery insight Building broad vs. niche from day one The shift from founder-selling to a scalable sales motion Organizing product teams around revenue vs. experience How Samsara uses LLMs and AI today What Kiren learned from longtime co-founder Sanjit Biswas Where to find Kiren: LinkedIn: https://www.linkedin.com/in/kirensekar/ Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson References: Cisco: https://www.cisco.com/ Clay: https://www.clay.com/ Cowgirl Creamery: https://cowgirlcreamery.com/ IBM: https://www.ibm.com/ Meraki: https://meraki.cisco.com/ Microsoft: https://www.microsoft.com/ Salesforce: https://www.salesforce.com/ Samsara: https://www.samsara.com/ Sanjit Biswas: https://www.linkedin.com/in/sanjitbiswas/ Uber: https://www.uber.com/ Timestamps: (01:27) Meraki’s growth and acquisition by Cisco (03:25) The "evaporating" exit strategy from Meraki (04:42) Identifying the IoT market gaps (07:38) The early keys to success at Samsara (09:39) What does quality mean to Kiren? (10:54) Building a customer-centric roadmap (17:34) Early customer research and the failed fridge monitoring idea (20:57) How a cheese producer helped create Samsara’s first prototype (28:06) Balancing depth and breadth in customer profiles (33:45) Developing customer trust to build feedback loops (40:27) How “ease of use” became a growth secret (44:23) Pricing strategies and market positioning (51:51) How Meraki influenced Samsara’s GTM strategy (57:19) Helping customers navigate change management (1:00:48) How Samsara’s team evolved during rapid growth (1:04:03) What AI means for an IoT giant

Sam Chaudhary is the co-founder and CEO of ClassDojo, a multi-product education platform used in 95% of U.S. schools and over 180 countries globally to connect teachers, students, and families. In this episode, Sam shares the full arc of building ClassDojo, from early skepticism about education and a failed group-making tool, to creating a communication platform loved by millions. In this episode, we discuss: Why ClassDojo was built for consumers (teachers, students and parents) instead of schools How ClassDojo grew entirely by word-of-mouth Sam’s unusual approach to building multiple new businesses The founder mindset required to build an industry leader Why relentless resourcefulness is an underrated skill And much more… References: Accel: https://www.accel.com/ Airbnb: https://www.airbnb.com/ Bill Gates: https://www.linkedin.com/in/williamhgates/ Brendan Kereiakes: https://www.linkedin.com/in/product/ ClassDojo: https://www.classdojo.com/ Dominick Bellizzi: https://www.linkedin.com/in/dominickbellizzi/ Geoff Ralston: https://www.linkedin.com/in/geoffralston/ Gonzalo Aguilar Málaga: https://www.linkedin.com/in/gonzalodecheck/ Hamilton Helmer: https://www.linkedin.com/in/hamilton-helmer-42983/ Imagine K12: https://www.imaginek12.com// Khan Academy: https://www.khanacademy.org/ Liam Don: https://www.linkedin.com/in/liamdon/ McKinsey: https://www.mckinsey.com/ Paul Graham: https://x.com/paulg Plaid: https://plaid.com/ Reid Hoffman: https://www.linkedin.com/in/reidhoffman/ Roblox: https://www.roblox.com/ Sal Khan: https://www.linkedin.com/in/khanacademy/ Superhuman: https://superhuman.com/ Tim Brady: https://www.linkedin.com/in/tim-brady-7a632510/ Y Combinator: https://www.ycombinator.com/ Where to find Sam: LinkedIn: https://www.linkedin.com/in/samchaudhary/ Twitter/X: https://x.com/samchaudhary Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Timestamps: (01:36) Why education is a “bad market” (02:52) Why enterprise education is broken (03:35) Building for families, not schools (06:53) Early challenges and insights (09:45) Sam’s unusual background (11:42) Meeting co-founder Liam at a hackathon (13:22) Getting into Imagine K12 with a group-making tool (19:47) The conversation with Reid Hoffman that changed everything (21:52) Building a network to reach more families (23:30) Scaling by building a community (33:18) Designing for delight and word-of-mouth growth (40:09) Launching the first monetization feature after 7 years (41:35) How to pick markets and when to go broad (46:04) The explosive expansion into the tutoring industry (55:11) Creating safe online spaces for kids (58:01) Harnessing AI in education (59:52) Lessons from ClassDojo’s playbook

Abhinav Asthana is the co-founder and CEO of Postman, the world's leading API collaboration platform used by millions of developers and thousands of companies. What began as a personal itch, a simple Chrome extension Abhinav built to make his own API work easier, became a global phenomenon within weeks. In this episode, we discuss: Making the leap from India to Silicon Valley The moment Abhinav realized Postman could win His principles behind building for developers and non-developers alike The early monetization experiments that led to their SaaS model The value of progressive complexity in product design How community building became a powerful growth lever And much more… References: Abhijit Kane: https://www.linkedin.com/in/abhijitkane/ Adobe: https://www.adobe.com/ Ankit Sobti: https://www.linkedin.com/in/ankit-sobti/ Figma: https://www.figma.com/ Kong Inc.: https://konghq.com/ National University of Singapore: https://nus.edu.sg/ Postman: https://www.postman.com/ Ram Gupta: : https://www.linkedin.com/in/ram-gupta-39b9711/ Slack: https://slack.com/ Stripe: https://stripe.com/ Stewart Butterfield: https://www.linkedin.com/in/butterfield/ Yahoo: http://yahoo.com/ Where to find Abhinav: LinkedIn: https://www.linkedin.com/in/abhinavasthana/ Twitter/X: https://x.com/a85 Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps: (01:18) Why early computer access changed everything (03:39) The first taste of the entrepreneurial bug (09:58) Building BITS360 in college (11:14) Curating entrepreneurial taste (15:49) The ventures that didn’t make it (20:53) The problems that preceded Postman (29:56) How Postman’s team was formed (34:01) Why clear roles prevent chaos (34:50) Scrappy startup life in the early days (36:26) Postman’s path to monetization (39:59) Building a truly collaborative platform (43:00) Navigating market and customer needs (46:02) Cracking the go-to-market code (49:39) Bridging the developer-enterprise divide (54:43) The open-source dilemma

Cameron Adams is the co-founder and Chief Product Officer at Canva, the design platform valued at $42B as of July 2025, used by over 230 million people every month. Before starting Canva, Cameron was a designer and engineer at Google and co-founded Fluent, an email startup. In this episode, Cameron walks through Canva’s earliest days — from the remarkably fast courtship with co-founders Melanie Perkins and Cliff Obrecht, to the counterintuitive product decisions that helped Canva instantly resonate with users who thought they would never design anything. In this episode, we cover: How Canva turned social media managers into early evangelists Balancing a huge vision with scrappy execution Hard lessons from their near-silent launch day The two growth levers that changed everything And much more… References: Adobe: https://www.adobe.com/home Atlassian: https://www.atlassian.com/ Campaign Monitor: https://www.campaignmonitor.com/ Canva: https://www.canva.com/ Cliff Obrecht: https://www.linkedin.com/in/cliff-obrecht-79ba9920/ Dave Greiner: https://www.linkedin.com/in/davegreiner/ Lars Rasmussen: https://www.linkedin.com/in/larserasmussen/ Melanie Perkins: https://www.linkedin.com/in/melanieperkins/ Mike Cannon-Brookes: https://www.linkedin.com/in/mcannonbrookes/ New York Stock Exchange: https://www.nyse.com/ Pinterest: https://pinterest.com/ Scott Farquhar: https://www.linkedin.com/in/scottfarquhar/ Where to find Cameron: LinkedIn: https://www.linkedin.com/in/themaninblue/ Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ X/Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps: (01:24) The birth of Canva (04:32) Meeting Canva’s co-founders (11:22) Building the first iteration of Canva (15:26) The discovery that changed prototyping (20:48) Why onboarding was the unlock for retention (27:36) The anticlimactic launch day (32:43) How word-of-mouth spurred early retention (36:33) Targeting different user personas (41:02) Building a community on social media (43:38) Two impactful growth levers (47:14) Why Canva should have gone mobile sooner (48:12) What underpins Canva’s dominance today (53:37) Rebuilding for enterprise (58:38) Lessons from Canva’s tough times