First Round

In Depth

A Management , Business and Entrepreneurship podcast

#55 in Management · 🇵🇰 #60 in Management · 🇳🇬

About the show

Welcome to In Depth, a podcast from The First Round Review that’s dedicated to surfacing the tactical advice founders and startup leaders need to grow their teams, their companies and themselves. Hosted by Brett Berson, a partner at First Round, In Depth will cover a lot of ground and a wide range of topics, from hiring executives and becoming a better manager, to the importance of storytelling inside of your organization. But every interview will hit the level of tactical depth where the very best advice is found. We hope you’ll join us. Subscribe to “In Depth” now and learn more at firstround.com

Newest episodes

Competing with OpenAI and Meta for your inbox | Jean-Denis Greze (Town Co-founder & CEO)

Oct 28, 2026 47 min

In this episode of In Depth, Todd sits down with Jean-Denis Greze, co-founder and CEO of Town, the AI work assistant that gives every employee their own agent. Before Town, Jean-Denis spent seven years as CTO of Plaid and led engineering teams at Dropbox, where he and Todd first worked together. In this conversation, they dive into what it takes to build in tech's hottest category while competing with Microsoft, Google and the frontier labs, why Town bet on work agents over personal agents, and how to get agents to share the right information with each other. In today's episode, we discuss: The edge that keeps Town competitive with Google and Microsoft How user feedback adjusted Town’s product Why Jean-Denis believes people will start delegating decision-making to AI What a multiplayer AI assistant world looks like Why Town started rolling back its guardrails after users approved 95% of agent actions References: Anthropic: https://www.anthropic.com/ Bret Taylor: https://www.linkedin.com/in/brettaylor/ Dropbox: https://www.dropbox.com/ Facebook: https://www.facebook.com/ Figma: https://www.figma.com/ Glean: https://www.glean.com/ Google: https://www.google.com/ HubSpot: https://www.hubspot.com/ Instinct: https://instinct.com/ Meta: https://www.meta.com/ Microsoft: https://www.microsoft.com/ OpenAI: https://openai.com/ Plaid: https://plaid.com/ Salesforce: https://www.salesforce.com/ Sierra: https://sierra.ai/ Slack: https://slack.com/ Town: https://www.town.com/ Where to find Jean-Denis: LinkedIn: https://www.linkedin.com/in/jeandenisgreze Twitter/X: https://x.com/jgreze Where to find Todd: LinkedIn: https://www.linkedin.com/in/toddj0/ Twitter/X: https://x.com/tjack Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://x.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on a...

The fastest way to learn is to run two competing bets | Jay Parikh (EVP CoreAI, Microsoft)

Aug 27, 2026 1 hr 2 min

In the latest episode of Executive Function, Brett sits down with Jay Parikh, Executive Vice President of CoreAI at Microsoft. Before joining Microsoft, Jay spent over a decade as Facebook's global head of engineering, scaling the company from a few hundred engineers to billions of users, then ran the cybersecurity company Lacework as CEO through its acquisition by Fortinet. In this conversation, he breaks down the five ingredients of great engineering leadership, discusses why he'd rather run two competing bets in parallel than forecast a winner, and explains why company culture remains more important than ever for teams to get right. In today's episode, we discuss: The five ingredients that separate excellent engineering leadership from the rest How to protect your team from large shifts in public perception The mindset shift organizations need to maintain speed at scale How every layer of the organization needs to stay connected to the customer Why Jay runs "brain trusts" of senior ICs with zero managers in the room References Akamai: https://www.akamai.com/ AWS: https://aws.amazon.com/ Facebook: https://www.facebook.com/ George Conrades: https://www.linkedin.com/in/georgeconrades/ Mark Zuckerberg: https://x.com/finkd Microsoft: https://www.microsoft.com/ Paul Sagan: https://www.linkedin.com/in/paul-sagan-59654a1/ Tom Leighton: https://www.linkedin.com/in/tleighton/ Where to find Jay LinkedIn: https://www.linkedin.com/in/jayparikh/ Twitter/X: https://x.com/jayparikh 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 00:00 Introduction 00:36 How leadership...

What startups get wrong about enterprise | Lindsey Scrase (COO, Checkr)

Jul 30, 2026 1 hr 8 min

In the latest episode of Executive Function, Brett sits down with Lindsey Scrase, COO of Checkr. Before joining Checkr as CRO and later stepping into the COO seat, Lindsey spent nearly a decade at Google Cloud as global managing director for SMB, mid-market, and startups. In this conversation, she breaks down why moving upmarket into enterprise trips up so many startups looking to scale, how Checkr rebuilt its sales compensation model to keep pace with growth, and where AI is already reshaping her operations and go-to-market teams. In today's episode, we discuss: Why operators who thrive at massive-scale companies often struggle when they join a startup The hard-won lessons from Checkr's early enterprise push that nearly failed Why Checkr’s C-suite meets every morning with no specific agenda The surprising challenges moving from CRO to COO How Checkr turned AI experiments into operating systems References Amazon: https://www.amazon.com Checkr: https://checkr.com Claude: https://claude.com Daniel Yanisse: https://www.linkedin.com/in/yanisse/ DoorDash: https://www.doordash.com Google: https://www.google.com Lovable: https://lovable.dev Microsoft: https://www.microsoft.com Where to find Lindsey LinkedIn: https://www.linkedin.com/in/lindsey-scrase-0702442/ Twitter/X: https://twitter.com/Lscrase 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 00:00 Introduction 00:06 Why big-company executives often struggle in startups 02:18 What Checkr's first CRO needed to accomplish 03:33 How to take on an entrenched category leader 06:58 Why leaders underestimate how h...

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All episodes

Competing with OpenAI and Meta for your inbox | Jean-Denis Greze (Town Co-founder & CEO)

Oct 28, 2026 47 min

The fastest way to learn is to run two competing bets | Jay Parikh (EVP CoreAI, Microsoft)

Aug 27, 2026 1 hr 2 min

What startups get wrong about enterprise | Lindsey Scrase (COO, Checkr)

Jul 30, 2026 1 hr 8 min

How Gamma pulled off their AI pivot | Jon Noronha (Co-founder and CPO of Gamma)

Jul 24, 2026 1 hr 2 min

In this episode of In Depth, Brett sits down with Jon Noronha, co-founder and CPO of Gamma, the AI-native presentation platform used by more than 100 million people. In this conversation, he walks through Gamma’s distinct eras of product-market fit: from a pre-AI struggle with a year of runway left, to an overnight AI-fueled explosion, to today’s unplanned scramble into enterprise sales. Jon also unpacks his hard-won lessons on horizontal versus vertical bets, monetizing AI products, and why nailing onboarding turned out to be the whole game. In today's episode, we discuss: Why Gamma's all-in AI launch in March 2023 saved their startup How fixing a simple onboarding problem accidentally uncovered Gamma’s entire product-market fit Why Jon bet Gamma on a horizontal product against the advice of nearly every investor How Gamma's daily signups climbed from hundreds to over 100,000 with zero paid marketing What building three pricing tiers taught Jon about monetizing AI References Canva: https://www.canva.com/ Corgi: https://www.corgi.insure/ Facebook: https://www.facebook.com/ Gamma: https://gamma.app/ Google: https://www.google.com/ Linear: https://linear.app/ Loom: https://www.loom.com/ Microsoft: https://www.microsoft.com/ Notion: https://www.notion.com/ Optimizely: https://www.optimizely.com/ Salesforce: https://www.salesforce.com/ Slack: https://slack.com/ Zoom: https://www.zoom.us/ Where to find Jon Noronha LinkedIn: https://www.linkedin.com/in/jonnoronha/ Twitter/X: https://twitter.com/thatsjonsense 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 Timestam...

Why Plaid’s COO cold-calls new hires | Eric Sager (COO of Plaid)

Jul 16, 2026 1 hr 9 min

In the latest episode of Executive Function, Brett sits down with Eric Sager, COO of Plaid, following stints as CRO of Bluevine and Head of Sales at Square. During his seven-year tenure at Plaid, Eric has helped lead the business through a pandemic, Visa's collapsed acquisition, a fintech downturn, and the AI boom. In today’s conversation, he unpacks how he kept teams focused during turbulent times, why he refuses to run at 100% capacity, and how he re-architected the go-to-market function as Plaid scaled. In today's episode, we discuss: How Plaid stayed focused after the Visa acquisition fell through and then raised at nearly 3x the price Why great COOs deliberately make themselves obsolete Why Eric treats speed, risk, and cost as a three-way trade-off, and why sometimes going slower wins How refusing to run at 100% capacity helped Plaid win OpenAI, Perplexity, and Replit Why Eric personally cold-calls brand-new employees References Bain & Company: https://www.bain.com Bluevine: https://www.bluevine.com Chase: https://www.chase.com Citibank: https://www.citi.com Eyal Lifshitz: https://www.linkedin.com/in/eyallifshitz/ Françoise Brougher: https://x.com/FrancoiseBr Gokul Rajaram: https://www.linkedin.com/in/gokulrajaram1/ Jack Dorsey: https://x.com/jack Michael Mankins: https://www.linkedin.com/in/michaelcmankins OpenAI: https://openai.com Perplexity: https://www.perplexity.ai Plaid: https://plaid.com Replit: https://replit.com Sarah Friar: https://www.linkedin.com/in/sarah-friar/ Square: https://squareup.com Visa: https://www.visa.com William Hockey: https://www.linkedin.com/in/william-hockey-04536710 Zach Perret: https://www.linkedin.com/in/zperret/ Where to find Eric Sager LinkedIn: https://www.linkedin.com/in/eric-sager-a529516 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://firstr...

How Supabase became the essential infrastructure for the AI era | Paul Copplestone (Co-founder, CEO)

Jun 25, 2026 59 min

In this episode of In Depth, Brett sits down with Paul Copplestone, co-founder and CEO of Supabase, the open-source Postgres platform now serving more than seven million developers. Before Supabase, Paul launched a Thumbtack-style marketplace in Southeast Asia and co-founded an office-management startup called Nimbus, experiences that taught him to separate fundraising from building and to find product-market fit before blitzscaling. He breaks down how a single tagline change for Supabase unlocked product-market fit, why he runs a fully distributed async team with near-zero attrition, and how he turned PLG signals into a product-led sales motion comped only on incremental uplift. In today's episode, we discuss: How changing one tagline helped Supabase go to #1 in Hacker News - an early sign of product market fit Why Paul ran Supabase like it had only $100K in the bank despite raising real money How Supabase rode three distinct AI waves, from pgvector to Bolt and Lovable, to Claude Code Why Supabase built a sales team comped only on the incremental uplift over a control group What the Toyota production system's "kaizen" taught Paul about unblocking a scaling team References: Ant Wilson: https://www.linkedin.com/in/ant-wilson-46179937 Bolt: https://bolt.new/ Claude Code: https://www.anthropic.com/claude-code Codex: https://openai.com/codex/ Entrepreneurs First: https://www.joinef.com/ Firebase: https://firebase.google.com/ Lovable: https://lovable.dev/ MongoDB: https://www.mongodb.com/ Next.js: https://nextjs.org/ PostgreSQL: https://www.postgresql.org/ Supabase: https://supabase.com/ Thumbtack: https://www.thumbtack.com/ Y Combinator: https://www.ycombinator.com/ Where to find Paul: LinkedIn: https://www.linkedin.com/in/paulcopplestone Twitter/X: https://x.com/kiwicopple Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round...

How to build a beloved tech brand | Sheila Joglekar Vashee (CMO, Figma)

Jun 4, 2026 1 hr 0 min

In today's conversation, Brett sits down with CMO of Figma, Sheila Joglekar Vashee. Previously the second marketing hire at Dropbox, where she helped scale the company past $1 billion in revenue, she now leads marketing at Figma fresh off its IPO. In an industry that has spent a decade trying to turn marketing into something closer to hedge fund trading, Sheila argues the art was always the point — we just stopped talking about it. She unpacks how to run marketing as a portfolio of moonshots, why giving teams different goals breeds dysfunction, how to scale taste across an organization, and why old playbooks are obsolete, even as the fundamentals hold. In today's episode, we discuss: How to run marketing like a portfolio of moonshots The value of disruptive energy for senior marketers Why "Ubiquity is the opposite of cool" How to actually scale taste across an organization What great marketing looks like in the AI era Referenced: Apple: https://www.apple.com/ Dennis Woodside: https://www.linkedin.com/in/dennis-woodside-341302/ Dropbox: https://www.dropbox.com/ Dylan Field: https://www.linkedin.com/in/dylanfield/ Figma: https://www.figma.com Francoise Brougher: https://www.linkedin.com/in/francoise-brougher-341a72/ Gap: https://www.gap.com/ Google Chrome: https://www.google.com/chrome/ Harley-Davidson: https://www.harley-davidson.com/ HubSpot: https://www.hubspot.com/ Notion: https://www.notion.com/ Opendoor: https://www.opendoor.com/ Pinterest: https://www.pinterest.com/ Square: https://squareup.com/ The Web Is What You Make of It (Dear Sophie): https://www.youtube.com/watch?v=pzOBOuyr-EU Urban Outfitters: https://www.urbanoutfitters.com/ Yamini Rangan: https://www.linkedin.com/in/yaminirangan/ Where to find Sheila: LinkedIn: https://www.linkedin.com/in/sheilavashee/ X: https://x.com/sheilavashee Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986644/ X: https://x.com/brettberson Where...

Why old-school sales work still wins in the AI era | Graham Moreno (Head of GTM, Parallel)

May 21, 2026 1 hr 2 min

In the latest episode of Executive Function, Brett sits down with Graham Moreno, Head of GTM at Parallel Web Systems. Before Parallel, Graham scaled Windsurf's GTM organization from three sellers to seventy-five in under a year, served as President through the Cognition acquisition, and earlier built and led enterprise sales teams at Grafana Labs and MongoDB. In this conversation, he unpacks why the AI-era backlash against structured enterprise sales misreads the data, how to design a process that raises the floor for ordinary reps without capping the ceiling for stars, and why selling to AI-native customers compresses an eight-week cycle into five business days. In today's episode, we discuss: Why in-person enterprise rollouts still beat product-led motions Building a robust sales process that still leaves room for unscripted moments Why the three highest-leverage early sales hires aren't sellers at all The case for outsized commission accelerators for star sellers — and the kind of person they attract Why most AI companies are skipping the in-person sales work that enterprise customers actually want References: Ahead: https://www.ahead.com Amazon: https://www.amazon.com Anthropic: https://www.anthropic.com Attio: https://www.attio.com Augment Code: https://www.augmentcode.com/ Cognition: https://cognition.ai Cursor: https://cursor.com Dani McCabe: https://www.linkedin.com/in/danielle-mccabe/ Datadog: https://www.datadoghq.com GitHub Copilot: https://github.com/features/copilot HubSpot: https://www.hubspot.com Jeremy Powers: https://www.linkedin.com/in/jeremypowers/ JPMorgan: https://www.jpmorgan.com Matt McClernan: https://www.linkedin.com/in/mattmcclernan/ MongoDB: https://www.mongodb.com Nicole Rettinger: https://www.linkedin.com/in/nicole-rettinger-23b20465/ Notion: https://www.notion.com OpenAI: https://openai.com Parag Agrawal: https://www.linkedin.com/in/paragagr/ Parallel: https://parallel.ai Snowflake:...

Why founders should bet on first-time executives | Praveer Melwani (CFO, Figma)

May 14, 2026 43 min

In this latest episode of Executive Function, Brett sits down with Praveer Melwani, CFO at Figma. Praveer joined Figma in 2017 as the company's first business operations and finance hire—when the team was around 30 people and not yet charging for the product—and stepped into the CFO seat in 2022, helping to lead the company’s IPO in 2025. In today’s conversation, Praveer breaks down the step functions that took him from IC to CFO, why Figma started acting like a public company three years before IPO, and how AI is rewriting capital allocation and the CFO job itself. In today's episode, we discuss: What separates a world-class finance leader from a traffic-cop CFO How Praveer went from Figma's first biz ops hire to CFO of a public company in nine years Why Figma started acting like a public company three years before its IPO What Praveer has learned working alongside Dylan Field for nine years Why Figma intentionally cut its 90% gross margin to invest in AI References: Adobe: https://www.adobe.com Brendan Mulligan: https://www.linkedin.com/in/brendanmulligan Cloudflare: https://www.cloudflare.com Dropbox: https://www.dropbox.com Dylan Field: https://www.linkedin.com/in/dylanfield/ Fidelity: https://www.fidelity.com Figma: https://www.figma.com GIC: https://www.gic.com.sg NerdWallet: https://www.nerdwallet.com Shaunt Voskanian: https://www.linkedin.com/in/shauntvoskanian/ Where to find Praveer: LinkedIn: https://www.linkedin.com/in/praveer-melwani 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: 00:00 Introduction 02:13 From banking to Dropbox to Figma...

Why great product leaders should stop obsessing over the roadmap | Diya Jolly (CPO & CTO of Xero)

Apr 30, 2026 49 min

In the latest episode of Executive Function, Brett is joined by Diya Jolly, Chief Product and Technology Officer at Xero. Before Xero, Diya was CPT at Okta and led YouTube's advertising monetization products at Google. In this conversation, she unpacks her three-bucket framework for delegating decisions, why the most important part of a CPO’s role is to drive team-wide ambition, and why the best executives need to spend half their time thinking, not doing. In today's episode, we discuss: Why a CPO's number one job is raising their team’s ambition, not shipping features How to demand the best from your team without creating a fear-based culture Why organizational politics is actually an incentives problem How Diya is “militant” with her calendar to carve out dedicated thinking time Why you should avoid chasing titles in your career - and what to chase instead References: Google: https://www.google.com Melio: https://meliopayments.com Okta: https://www.okta.com Sukhinder Singh Cassidy: https://www.linkedin.com/in/sukhinders/ Xero: https://www.xero.com Where to find Diya: LinkedIn: https://www.linkedin.com/in/diyajolly 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: 00:12 How an excellent CPO makes an impact on the business 02:01 How the CPO role shifts under founders vs hired CEOs 03:38 Influencing a founder without going deferential 07:37 How adding value to customers is always a net positive 08:45 Why roadmaps need more risk in the AI era 12:30 How to shelter innovation teams from the existing system 15:12 What's different about being a great CPO in 2026...

Inside Artemis' "AI vs AI" war | Shachar Hirshberg & Dan Shiebler (Co-founders, Artemis)

Apr 21, 2026 56 min

In this episode of In Depth, First Round Partner Josh Kopelman sits down with Shachar Hirshberg and Dan Shiebler, co-founders of Artemis, the AI-native security platform that just emerged from stealth with $70M in combined seed and Series A funding. Shachar and Dan unpack how they built a 30-person team in seven months, why AI-native companies are outperforming their AI-enabled counterparts, and why they plan to stay on a texting basis with every customer, even at scale. In today's episode, we discuss: How to interview for AI fluency when building an AI-native startup Why founder-market fit is a critical early signal for startup success The surprising lesson Dan learned from founder-led sales How Dan and Shachar are instilling customer-obsession into Artemis’ culture How the two co-founders approach conflict and decision-making References: Abnormal: https://abnormal.ai Amazon Web Services (AWS): https://aws.amazon.com Anthropic: https://www.anthropic.com Artemis: https://artemissecurity.com CrowdStrike: https://www.crowdstrike.com Demisto (now Cortex XSOAR): https://www.paloaltonetworks.com/cortex/cortex-xsoar OpenAI: https://openai.com Palo Alto Networks: https://www.paloaltonetworks.com Todd Jackson: https://www.linkedin.com/in/toddj0/ Where to find Shachar Hirshberg: LinkedIn: https://www.linkedin.com/in/shachar-hirshberg/ Where to find Dan Shiebler: LinkedIn: https://www.linkedin.com/in/dan-shiebler-10219b42/ Where to find Josh: LinkedIn: https://www.linkedin.com/in/jkopelman/ Twitter/X: https://x.com/joshk 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: 00:00 Introduction 00:06 What Artemis does and why now 02:51 Shachar’s AWS and Palo Alto playbook 05:15 Dan’s fo...

Scaling DoorDash to market dominance | Christopher Payne (Former COO, DoorDash)

Apr 17, 2026 1 hr 2 min

In this latest episode of Executive Function, Brett sits down with Christopher Payne, who spent a decade as President and COO at DoorDash, helping scale the company from roughly 70 employees to the dominant food delivery platform in the US. Before DoorDash, Christopher held senior operating roles at Amazon and eBay, where he led a sweeping overhaul of marketplace search. In this conversation, he unpacks what it actually takes to run an atoms-based business versus a software company, shares his "plate spinning" framework for allocating executive attention across a complex org, and makes the case for top-down goal setting over the bottom-up alternative. In today's episode, we discuss: How prior industry experience can be a liability when you're trying to reinvent the market How executives can practically focus their attention to stay close to product details What charisma actually looks like in executives—and why it's a staple trait to have The business case for setting ambitious goals top-down, not bottom-up References: Amazon: https://www.amazon.com/ Anthropic: https://www.anthropic.com/ Cheesecake Factory: https://www.thecheesecakefactory.com/ Cursor: https://cursor.com/ Dartmouth College: https://home.dartmouth.edu/ David Risher: https://www.linkedin.com/in/jdavidrisher DoorDash: https://www.doordash.com/ eBay: https://www.ebay.com/ Granola: https://www.granola.ai/ Hulu: https://www.hulu.com/ Jason Kilar: https://www.linkedin.com/in/jasonkilar Jeff Bezos: https://x.com/JeffBezos Lyft: https://www.lyft.com/ Microsoft: https://www.microsoft.com/ Tinder: https://tinder.com/ Tony Xu: https://www.linkedin.com/in/xutony Travis Kalanick: https://www.linkedin.com/in/traviskalanick Uber: https://www.uber.com/ University of Oregon: https://www.uoregon.edu/ Wharton School: https://www.wharton.upenn.edu/ Where to find Christopher Payne: LinkedIn: https://www.linkedin.com/in/christopherpayne Twitter/X: https://x.com/chrisp...

The most politically dangerous role in the C-suite | Katie Burke (COO, Harvey)

Apr 10, 2026 1 hr 11 min

In the latest episode of Executive Function, Brett sits down with Katie Burke, who recently became COO of Harvey after joining as Chief People Officer. Before Harvey, Katie spent 11 years in HR leadership at HubSpot, where she built one of tech's most distinctive cultures. In this conversation, she unpacks her marketing-minded approach to HR, why she hired deliberately from hospitality rather than corporate backgrounds, and why developing culture should be a strategic priority for any organization. In today's episode, we discuss: Why HR leaders should think like marketers The 2.5-year cultural hangover after a layoff The protein vs. sugar rule for employee feedback What it means to be the executive team’s own HR business partner What the Chief People Officer owes the board and what they don't References: Amazon: https://www.amazon.com Anique Drumright: https://www.linkedin.com/in/anique-drumright-53978a1a/ Brian Halligan: https://www.linkedin.com/in/brianhalligan/ Carmel Galvin: https://www.linkedin.com/in/carmelgalvin/ eBay: https://www.ebay.com Gabe Pereyra: https://www.linkedin.com/in/gabepereyra Harvey: https://www.harvey.ai HubSpot: https://www.hubspot.com Jacqui Canney: https://www.linkedin.com/in/jacquicanney Klaviyo: https://www.klaviyo.com Lorrie Norrington: https://www.linkedin.com/in/lorrienorrington/ Maggie Landers: https://www.linkedin.com/in/maggiecohenlanders/ Rippling: https://www.rippling.com ServiceNow: https://www.servicenow.com Winston Weinberg: https://www.linkedin.com/in/winston-weinberg/ Where to find Katie: LinkedIn: https://www.linkedin.com/in/katie-burke-965767a/ Twitter/X: https://x.com/katieburkie 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 Y...

What nobody tells engineers about becoming a CEO | Jay Kreps (Co-founder and CEO, Confluent)

Mar 26, 2026 1 hr 6 min

Jay Kreps is the co-founder and CEO of Confluent, the company built around Apache Kafka — the open-source data streaming platform he originally built while at LinkedIn. In this conversation, Jay shares his full journey: how Confluent grew from a scrappy group of engineers with no go-to-market experience into a publicly traded enterprise software company. He makes the case that the difference between what a company can do, and what it must do, is one of the most underrated building levers; illustrated through his years spent pushing Confluent towards a cloud product, in the face of widespread opposition. In this episode, we discuss: Why moving from software engineer to CEO requires almost an entirely new skillset The product marketing pyramid Jay built to explain Kafka to the world How Confluent bludgeoned its way to a cloud-first business when the early product was “embarrassing” The critical difference between what a company can do and what it must do What keeps scaling companies from becoming "Chipotle” References: Amazon Web Services: https://aws.amazon.com/ Apache Kafka: https://kafka.apache.org/ Benchmark: https://www.benchmark.com/ Confluent: https://www.confluent.io/ Jun Rao: https://www.linkedin.com/in/junrao LinkedIn: https://www.linkedin.com/ McKinsey & Company: https://www.mckinsey.com/ MySpace: https://www.myspace.com/ Neha Narkhede: https://www.linkedin.com/in/nehanarkhede Oracle: https://www.oracle.com/ Red Hat: https://www.redhat.com/ Snowflake: https://www.snowflake.com/ Where to find Jay: LinkedIn: https://www.linkedin.com/in/jaykreps/ Twitter/X: https://x.com/jaykreps 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/@FirstRoundCap...

The product wisdom every CPO should ignore | Jeremy Epling (CPO, Vanta)

Mar 19, 2026 1 hr 9 min

In the latest episode of Executive Function, Brett is joined by Jeremy Epling, CPO of security and compliance platform Vanta. Jeremy details his career journey, unpacking what it took to make the jump from tenured Microsoft executive to startup CPO. He also shares hard-won insights: how to maintain shipping velocity as headcount explodes, how to manage performance without the safety net of big-company process, and what it means to run a product org where the buck truly stops with you. In today's episode, we discuss: The mindset shift that made Jeremy's transition to startup CPO work Why it’s essential for the CPO to stay connected to details The rule to ensure teams ship fast while growing quickly Why rigid hierarchies derail quality decision-making How Jeremy uses open office hours for the entire company References: Christina Cacioppo: https://www.linkedin.com/in/ccacioppo/ Dropbox: https://www.dropbox.com GitHub: https://www.github.com Ironclad: https://www.ironcladapp.com Jensen Huang: https://www.linkedin.com/in/jenhsunhuang/ Lovable: https://lovable.dev Microsoft: https://www.microsoft.com Nat Friedman: https://www.linkedin.com/in/natfriedman/ NVIDIA: https://www.nvidia.com Span: https://www.span.app/ v0: https://v0.dev Vanta: https://www.vanta.com Where to find Jeremy: LinkedIn: https://www.linkedin.com/in/jeremy-epling-j40/ Twitter/X: https://x.com/jeremy_epling 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: 00:00 Introduction 00:09 Why most big-tech executives fail at startups 05:38 Great product leaders stay in the details 09:21 The...

Building Zipline: From launch disaster to drone-delivery giant | Keller Cliffton (Co-founder, CEO)

Mar 12, 2026 1 hr 10 min

Keller Cliffton is the co-founder and CEO of Zipline, the world's largest commercial autonomous delivery system, which today serves 5,000 hospitals across multiple countries and saves an estimated 17,000 lives per year. In this episode, Keller breaks down his extreme hiring philosophy that has powered Zipline for over a decade. He also walks through Zipline’s full origin story: from a near-dead home robot startup to a scrappy bet on drone blood delivery in Rwanda, to 135 million autonomous miles flown. In today's episode, we discuss: Why Zipline hires teenagers over PhDs Why the best startup employees are "heat-seeking missiles for pain" The 5 leadership attributes Zipline has never shared publicly The brutal firing advice that shaped Keller’s leadership How Rwanda’s health minister changed Zipline’s trajectory References: Airbnb: https://www.airbnb.com Alfred Lin: https://www.linkedin.com/in/linalfred/ Amazon: https://www.amazon.com Apple: https://www.apple.com Brian Chesky: https://www.linkedin.com/in/brianchesky/ Cleveland Clinic: https://my.clevelandclinic.org Netflix: https://www.netflix.com Paul Kagame: https://www.linkedin.com/in/paulkagame/ Reflect Orbital: https://www.reflectorbital.com Sequoia Capital: https://www.sequoiacapital.com SpaceX: https://www.spacex.com Sphero: https://www.sphero.com Tesla: https://www.tesla.com University of Washington: https://www.washington.edu Walmart: https://www.walmart.com Zipline: https://www.zipline.com Where to find Keller: LinkedIn: https://www.linkedin.com/in/kellerrc/ Twitter/X: https://x.com/Keller 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 pla...

Snowflake’s first sales hire on scaling from $0 to $3.5B | Chris Degnan (Former CRO, Snowflake)

Feb 26, 2026 59 min

Chris Degnan was the first sales hire at Snowflake and spent 11 years scaling the company from zero to $3.5 billion in revenue as its CRO, working alongside four different CEOs and learning from each one. In this episode, Chris breaks down what it actually takes to scale an enterprise sales organization, why MEDDIC is the methodology every founder should know, and what working under Frank Slootman taught him about firing fast, taking feedback and finding the fakers in your team. In today's episode, we discuss: What the CRO job looks like at $10M vs. $1B+ Why sales leaders must know how to sell the product themselves The MEDDIC methodology and why it's a founder's best insurance policy How to find the fakers, manage-uppers and passengers in your org What Frank Slootman got right — and wrong — about scaling Snowflake Why most AI companies will face a go-to-market reckoning References: Amazon: https://www.amazon.com/ Bob Muglia: https://www.linkedin.com/in/bob-muglia-714ba592/ Carl Eschenbach: https://www.linkedin.com/in/carl-eschenbach-980543/ Christian Kleinerman: https://www.linkedin.com/in/christian-kleinerman-a973102/ Denise Persson: https://www.linkedin.com/in/denisepersson/ Dell: https://www.dell.com/ Frank Slootman: https://www.linkedin.com/in/frankslootman/ John McMahon: https://www.linkedin.com/in/johnmcmahon1/ Michael Scarpelli: https://www.linkedin.com/in/michael-scarpelli-1b289b9/ Microsoft: https://www.microsoft.com/ Oracle: https://www.oracle.com/ Salesforce: https://www.salesforce.com/ Snowflake: https://www.snowflake.com/ Sridhar Ramaswamy: https://www.linkedin.com/in/sridhar-ramaswamy/ Stanford Graduate School of Business: https://www.gsb.stanford.edu/ Where to find Chris: LinkedIn: https://www.linkedin.com/in/chris-degnan/ 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://...

Why 90% of CROs will fall behind in the next 2 years | Stevie Case (CRO, Vanta)

Feb 19, 2026 1 hr 11 min

Stevie Case is the CRO of Vanta, the trust management platform serving everyone from founders to Fortune 100 CISOs. A former pro-video gamer who stumbled into sales through a mentor's bet, Stevie has built one of the most unconventional paths to the C-suite in tech. In this episode, she unpacks why early revenue hires fail, what separates a true CRO from a VP of Sales, and why she believes fewer than 10% of current CROs will thrive by 2028. In today's episode, we discuss: Why early revenue hires fail What a top 1% CRO actually does The scaling mistake Stevie made by copying Twilio's playbook at Vanta Why Vanta remains 100% sales-led at every segment AI vs. humans in go-to-market References: Cursor: https://cursor.sh/ Gong: https://www.gong.io/ Salesforce: https://www.salesforce.com/ Twilio: https://www.twilio.com/ Vanta: https://www.vanta.com/ Where to find Stevie: LinkedIn: https://www.linkedin.com/in/steviecase/ 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: 00:00 Why early revenue hires fail 02:23 Who to hire at $5M in revenue 04:16 Coin-operated sellers vs. long-term builders 05:57 What excellence looks like in the CRO role 07:44 Metrics, confidence, and velocity 12:04 Should CROs lead sales? 14:39 From shy seller to revenue leader 16:36 Learning to scale at Twilio 17:44 "There is no CRO playbook" 19:58 Stevie's scaling mistake at Vanta 22:16 Why Vanta stays 100% sales-led 23:16 The value of planning 24-26 months ahead 29:54 When trusting intuition was the wrong call 30:49 Do humans still have a place in the future of GTM? 33:33 Stevie's lead...

Figma is not the source of truth | Ryan Lucas (VP of Design, Rippling)

Feb 12, 2026 1 hr 6 min

In the second Executive Function episode, Brett sits down with Ryan Lucas, VP of Design at Rippling. Before Rippling, Ryan led design at Retool and co-founded multiple startups, bringing a rare founder's perspective to design leadership. A trained industrial designer, Ryan traces the roots of modern software design back 2,000 years to make the case that products must be useful, usable, and desirable - and above all, used. In today's episode, we discuss: Why design leaders who stop designing stop leading The four pillars every design manager must master How to delegate when you're a perfectionist Why leaders need strong opinions How to scale good judgment What Rippling's operating system teaches about speed and commitments References: Airbnb: https://www.airbnb.com/ Amazon: https://www.amazon.com/ Apple: https://www.apple.com/ Asana: https://www.asana.com/ Brian Chesky: https://www.linkedin.com/in/brianchesky/ CrossFit: https://www.crossfit.com/ Figma: https://www.figma.com/ Honeywell: https://www.honeywell.com/ Liz Sanders: https://www.linkedin.com/in/sandersliz/ Nest: https://store.google.com/category/google_nest Notion: https://www.notion.so/ Parker Conrad: https://www.linkedin.com/in/parkerconrad/ Patrick Collison: https://www.linkedin.com/in/patrickcollison/ Retool: https://retool.com/ Rippling: https://www.rippling.com/ Stripe: https://www.stripe.com/ Where to find Ryan: LinkedIn: https://www.linkedin.com/in/ryanwlucas/ 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: 00:00 Intro 00:08 What design actually does at a software company...

Executive Function: Building systems that can make decisions without you | Jeanne DeWitt Grosser (COO, Vercel)

Feb 5, 2026 1 hr 15 min

In the first Executive Function episode, Brett sits down with Jeanne De Witt Grosser, Chief Operating Officer at Vercel. Before Vercel, Jeanne spent nearly a decade at Stripe, where she built and scaled global revenue teams and led product partnerships. In this conversation, she unpacks what separates good executives from extraordinary ones, shares her rigorous executive hiring process, and reveals the brutally honest performance review feedback she'll never forget. In today's episode, we discuss: What it takes to operate at 30,000 feet and ground level simultaneously The leap from frontline manager to manager of managers Inside Jeanne's executive interview process The inherent value of driver trees for metrics Why context is everything References: Akamai: https://www.akamai.com Claire Johnson: https://www.linkedin.com/in/claire-hughes-johnson-7058/ Culture Amp: https://www.cultureamp.com Guillermo Rauch: https://www.linkedin.com/in/rauchg John Collison: https://www.linkedin.com/in/johnbcollison/ Next.js: https://nextjs.org Nike: https://www.nike.com OpenAI: https://www.openai.com Patrick Collison: https://www.linkedin.com/in/patrickcollison Stanford Graduate School of Business: https://www.gsb.stanford.edu Stripe: https://www.stripe.com Vercel: https://www.vercel.com Where to find Jeanne: LinkedIn: https://www.linkedin.com/in/jeannedewitt 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: (01:17) What separates good executives from extraordinary ones (02:48) How leadership changes as companies scale (04:15) What an executive is actually accountabl...

Building Meter for decades, not an exit | Anil Varanasi (Co-founder and CEO)

Dec 10, 2025 1 hr 14 min

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 Univ...

How Harness runs 16 “startups within a startup” at scale | Jyoti Bansal (Co-founder and CEO)

Nov 19, 2025 1 hr 5 min

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.cisc...

How to build a company you’ll run forever | Zack Kanter (Founder and CEO of Stedi)

Nov 6, 2025 1 hr 24 min

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.f...

Go hard early: How lessons from Verkada shaped Serval's AI agents for IT teams | Jake Stauch (Founder and CEO)

Oct 23, 2025 1 hr 23 min

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.cloud...

The pivot that paid off: How fal found explosive growth in generative media | Gorkem Yurtseven (Co-founder and CTO)

Oct 22, 2025 59 min

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/...

From dorm room to life-saving AI | Prepared’s story | Michael Chime (Co-founder & CEO of Prepared)

Oct 1, 2025 1 hr 9 min

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://thielfellows...

Saying yes to everything: How customer obsession built Samsara | Kiren Sekar (CPO)

Sep 11, 2025 1 hr 8 min

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 (20:5...

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

Sep 3, 2025 1 hr 12 min

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...

From Chrome extension to $5B platform | Postman’s journey | Abhinav Asthana (Co-founder & CEO)

Aug 28, 2025 1 hr 6 min

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:...

How Canva leveraged unconventional growth levers to grow to $42B | Cameron Adams (Co-founder & CPO)

Aug 20, 2025 1 hr 4 min

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...

Twitter's former CEO on rebuilding the web for AI | Parag Agrawal (Co-founder and CEO of Parallel)

Aug 14, 2025 1 hr 5 min

Parag Agrawal is the co-founder and CEO of Parallel, a startup building search infrastructure for the web’s second user: AIs. Before launching Parallel, Parag spent over a decade at Twitter, where he served as CTO and later CEO during a period of intense transformation, as well as public scrutiny. In this episode, Parag shares what he learned from his time at Twitter, why the web must evolve to serve AI at massive scale, how Parallel is tackling “deep research” challenges by prioritizing accuracy over speed, and the design choices that make their APIs uniquely agent-friendly. We also discuss: Why Parallel designs for AI as the primary customer Lessons from 11 years at Twitter and applying them to a startup Potential business models to keep the web open for AI Hiring philosophy: balancing high potential and experienced talent The evolving role of engineers in an AI-assisted world Why “agents” are finally becoming useful in production And much more… References: Bloomberg launch coverage: https://www.bloomberg.com/news/articles/2025-08-14/twitter-ex-ceo-parag-agrawal-is-moving-past-his-elon-musk-drama Clay: https://www.clay.com/ Index Ventures: https://www.indexventures.com/ Josh Kopelman: https://www.linkedin.com/in/jkopelman/ KLA: https://www.kla.com/ OpenAI: https://openai.com/ Parallel: https://parallel.ai/ Patrick Collison: https://www.linkedin.com/in/patrickcollison/ Stripe: https://stripe.com/ Where to find Parag: LinkedIn: https://www.linkedin.com/in/paragagr/ X/Twitter: https://x.com/paraga Where to find Todd: LinkedIn: https://www.linkedin.com/in/toddj0/ X/Twitter: https://x.com/tjack 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: (1:26) Founding Parallel wit...

Ignoring Silicon Valley advice to build a $3B fintech unicorn | Immad Akhund (Co-founder and CEO of Mercury)

Aug 6, 2025 1 hr 1 min

Immad Akhund is the CEO and co-founder of Mercury, a digital banking platform that’s become the go-to financial infrastructure for startups. Before Mercury, Immad spent nearly two decades founding companies, learning the hard way what separates a good idea from a great business. In this episode, Immad shares the hard-earned lessons from launching Mercury as his third startup. He unpacks how he recognized this was the right idea to pursue, what strong product-market fit feels like, and why trying to "iterate" your way to success often leads founders astray. In this episode, we discuss: Mercury’s unusual culture playbook – and why it works How to hire with intention The trap of weak product-market fit Shipping under intense pressure during the SVB crisis And much more… References: Airbnb: https://www.airbnb.com/ Andreessen Horowitz: https://a16z.com/ Apple: https://www.apple.com/ Block: https://block.xyz/ Brex: https://www.brex.com/ Chime: https://www.chime.com/ Gusto: https://gusto.com/ Mercury: https://mercury.com/ Paul Graham: https://x.com/paulg Plaid: https://plaid.com/ Stripe: https://stripe.com/ SVB (Silicon Valley Bank): https://www.svb.com/ True Link Financial: https://www.truelinkfinancial.com/ Varo: https://www.varomoney.com/ Y Combinator: https://www.ycombinator.com/ Where to find Immad: LinkedIn: https://www.linkedin.com/in/iakhund/ 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: (1:07) Hard-won lessons from serial entrepreneurship (2:02) You shouldn’t copy-paste advice (6:57) Why personality trumps culture playbooks (8:48...

Inside the ex-YC partner’s $15B self driving car company | Qasar Younis

Aug 1, 2025 1 hr 0 min

Qasar Younis is the co-founder and CEO of Applied Intuition, a leading vehicle intelligence platform that helps companies develop and deploy autonomous systems at scale. In June 2025, the company raised $600M at a $15B valuation. Before Applied Intuition, Qasar was the COO and a group partner at Y Combinator, and earlier founded TalkBin, which was acquired by Google. He’s also held engineering roles at General Motors and Bosch. In today’s episode, we discuss: • The two founder traits Silicon Valley undervalues • How to get 1–3 extra months of work done every year • Lessons from YC on pattern matching and founder feedback • The battle-tested startup formula Qasar used at Applied • Why co-founder fit is make-or-break • Applied’s playbook: vertical SaaS, product-led GTM, and leveraging VC networks • Why Applied went multi-product in the early days • Contrarian takes on startup culture, compensation, and cost control • Why domain expertise is making a comeback • And much more… Referenced: • Applied Intuition: https://www.appliedintuition.com • Ansys: https://www.ansys.com • Bilal Zuberi: https://www.linkedin.com/in/bzuberi • Bosch: https://www.bosch.com • Elad Gil: https://www.linkedin.com/in/eladgil • General Motors: https://www.gm.com • “Google’s Acquisition of TalkBin”: https://techcrunch.com/2011/04/25/google-acquires-talkbin-a-feedback-platform-for-businesses-thats-only-five-months-old/ • “High Output Management”: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884 • Kyle Vogt: https://x.com/kvogt • Marc Andreessen: https://x.com/pmarca • “Only the Paranoid Survive”: https://www.amazon.com/Only-Paranoid-Survive-Strategic-Inflection/dp/0385483821 • Paul Graham: https://x.com/paulg • Peter Ludwig: https://www.linkedin.com/in/peterwludwig • Sam Altman: https://x.com/sama • TalkBin: https://www.crunchbase.com/organization/talkbin • “The History of the Standard Oil Company”: https://www.amazon.com/History-Standard-Oil-Company-Volumes/dp/1519455860...

What Braintrust got right about product-market fit | Ankur Goyal (Founder and CEO)

Jul 24, 2025 1 hr 10 min

Ankur Goyal is the founder and CEO of Braintrust, an end-to-end platform for building AI apps. Before that, he founded Impira, a data management platform that was acquired by Figma, where he went on to lead the AI team. Ankur kickstarted his career when he dropped out of college to join the founding team at SingleStore (formerly MemSQL), a formative experience that shaped his views on building for high-bar users. In today’s episode, we discuss: • Ankur’s early lessons on quality from MemSQL • How frustration with evals at Figma led to Braintrust • Why they delayed go-to-market (on purpose) • How to find product-market fit in a new market • Why building great software comes from a place of “paranoia” • And much more… Referenced: • Airtable: https://www.airtable.com/ • Adam Prout: https://www.linkedin.com/in/adam-prout-0b347630/ • Braintrust: https://braintrust.dev • Brian Helmig: https://www.linkedin.com/in/bryanhelmig/ • Coda: https://coda.io/ • Databricks: https://www.databricks.com/ • David Kossnick: https://www.linkedin.com/in/davidkossnick/ • Figma: https://www.figma.com/ • Goldman Sachs: https://www.goldmansachs.com/ • Kris Rasmussen: https://www.linkedin.com/in/kristopherrasmussen/ • Manu Goyal: https://www.linkedin.com/in/mngyl/ • MemSQL: https://www.singlestore.com/ (now SingleStore) • Nikita Shamgunov: https://www.linkedin.com/in/nikitashamgunov/ • OpenAI: https://openai.com/ • Snowflake: https://www.snowflake.com/ • Zapier: https://zapier.com/ Where to find Ankur: • LinkedIn: https://www.linkedin.com/in/ankrgyl/ • Twitter/X: https://x.com/ankrgyl 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:...

How Gusto built a $9.5 billion company by identifying a burning problem

Jul 1, 2025 55 min

Tomer London is the co-founder and Chief Product Officer at Gusto, the payroll and people platform used by over 400,000 businesses. He grew up helping run his dad’s clothing store in Israel — an experience that sparked his mission to build better tools for small business owners. After moving to the US for a PhD at Stanford, he met his co-founders and started Gusto. In today’s episode, we discuss: Reinventing payroll without any prior experience Why you should hire for humility, not just talent Gusto’s scrappy customer research: cold calling from a walk-in closet Why founders should embrace customer rejection Why “emotional urgency” matters more than polite feedback The weekly co-founder ritual that built trust How Gusto expanded from payroll to a multi-product platform Building products customers actually love And so much more Referenced: ADP Eddie Kim Gusto Intuit Josh Reeves Paychex Steve Jobs’ “Secrets to Life” clip Steve Jobs’ Stanford Commencement Speech Wells Fargo Y Combinator Where to find Tomer: LinkedIn Twitter/X Where to find Brett: LinkedIn Twitter/X Where to find First Round Capital: Website First Round Review Twitter/X YouTube This podcast on all platforms Timestamps: (00:00) How a childhood around SMBs shaped Tomer’s founder mindset (03:24) The three things that led to the creation of Gusto (07:17) Hiring for humility, not just talent (09:28) The tug-of-war test for product-market fit (11:58) Why founders should actively seek rejection (15:34) Gusto’s scrappy customer research: cold calling from a walk-in closet (17:45) Betting on SMBs – and ignoring investor advice (20:44) “It’s not an MVP, it’s something that wows people” (24:09) Serving SMBs vs. startups (28:36) How to find the right co-founders (31:09) The weekly co-founder ritual that built trust (35:02) Reinventing payroll without any prior experience (38:49) Gusto’s “start small” GTM playbook (42:16) The big opportunity...

How rejecting conventional wisdom grew Sentry to a $3 billion company | David Cramer (Co-founder and CPO)

Jun 19, 2025 1 hr 41 min

David Cramer is the co-founder of Sentry, the leading open-source error monitoring tool used by over 90,000 companies. A self-taught engineer, he went from 9th grade high school dropout and Burger King manager to building one of the most widely adopted developer tools in the world — by working hard and rejecting conventional wisdom. As of 2022, Sentry is valued at over $3 billion. David now serves as Chief Product Officer, after previously holding roles as CEO and CTO. In this episode, we discuss: How David went from managing a Burger King to landing his first job as a software engineer How an code snippet grew into a ubiquitous monitoring platform Why open source is an underrated distribution hack How a ruthless competitive streak and obsession with excellence fueled Sentry’s rise And so much more… Referenced: Aaron Levie Beats by Dre Cursor Dan Levine Datadog Disqus Dropbox Heroku Max Levchin Okta Omar Johnson Oracle Sentry Satya Nadella Stripe Uber VS Code WindSurf Y Combinator Yandex Where to find David: LinkedIn Twitter/X Where to find Brett: LinkedIn Twitter/X Where to find First Round Capital: Website First Round Review Twitter/X YouTube Timestamps: (4:01) Learning to code through gaming (6:31) Dropping out of high school (9:47) Building infrastructure at Disqus (10:20) “Software is not that hard” (12:45) Early interest in open source (15:45) The birth of Sentry (23:37) Two common founder mistakes (27:13) David’s unwavering focus (28:17) Sentry’s journey to venture backing (36:43) Finding conviction in decisions (41:11) How Sentry found PMF (46:34) More confidence, less ego (48:08) Is sales valuable? (51:31) David’s personal philosophy (1:01:17) Money is not the hardest problem (1:06:27) Marketing won’t fix a bad product (1:10:34) What makes Sentry’s market unique (1:16:24) “You’re gonna mess up” (1:22:08) Why brand will always matter (1:30:51) Eliminating all competit...

Inside Linear: Why craft and focus still win in product building | Karri Saarinen (Co-founder and CEO)

Jun 10, 2025 1 hr 33 min

Karri Saarinen is the co-founder and CEO of Linear, the project management tool built for high-performance software teams. Since its founding in 2019, Linear has achieved a valuation of $1.25B as of 10th June 2025 and now counts companies like OpenAI, Ramp and Vercel as customers. Before founding Linear, Karri led design at Airbnb and Coinbase, and previously co-founded Kippt, a bookmarking tool acquired by Coinbase. In today’s episode, we discuss Karri’s childhood love for computers that shaped his career The lessons he learned from a failed first startup Linear’s founding principles The early validation strategies used to shape the product Why Karri believes in small teams And much more… Referenced Airbnb Brian Armstrong Brian Chesky Coinbase Jori Lallo Linear Tuomas Artman Y Combinator Where to find Karri LinkedIn Twitter/X Where to find Brett LinkedIn Twitter/X Where to find First Round Capital Website First Round Review Twitter/X YouTube Timestamps (1:37) Childhood roots in computers and design (6:54) Founding Kippt and lessons from a failed bookmarking startup (13:14) Lessons from a serial entrepreneur (19:32) Why teams shouldn’t grow too quickly (25: 03) Linear’s early beginnings (36:55) The unexpected power of intuition (42:41) Linear’s unusual approach to user growth (47:29) What shaped Linear’s early product roadmap (52:02) Startups shouldn’t try to boil the ocean (57:30) The power of extreme focus (59:18) Design “something for someone” (1:04:29) Flexibility vs. simplicity (1:17:27) Lead your team with strong principles (1:24:45) Design founders vs. engineering founders

How Wes Kao coaches founders to influence, lead, and get what they want | Wes Kao (Executive coach, co-founder of Maven)

May 22, 2025 1 hr 19 min

Wes Kao is an executive coach, advisor, and instructor, best known for her newsletter on high-impact communication, and for co-founding course platform Maven and the AltMBA with Seth Godin. Across her career, Wes has helped leaders communicate with clarity and conviction, whether it’s rallying a team, pitching investors, or influencing stakeholders. In this episode, Wes and Brett unpack how founders can be more persuasive, why playing to your strengths is critical, and how everyone can raise their own standards. --- In today’s episode, we discuss: Wes’ “personality-message fit” framework Why charisma is misunderstood How anyone can improve their communication What being told you need to “be more strategic” actually means and much more… --- Referenced: AltMBA: https://altmba.com/ Maven: https://maven.com/ Seth Godin: https://www.sethgodin.com/ Udemy: https://www.udemy.com/ --- Where to find Wes: LinkedIn: https://www.linkedin.com/in/weskao --- 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: (1:54) Charisma is misunderstood (4:44) What underpins authenticity? (13:53) Clarity in communication (16:02) Start with your ideal outcome (22:05) The role of power dynamics (26:39) Should you work on weaknesses? (29:02) Effective self-reflection (32:13) Role-strength fit (37:39) What do you resent? (39:17) “Be more strategic” (45:20) Stack ranking (51:45) How AltMBA started (60:04) Defining your craft

From reluctant founder to $2B valuation: The story of Persona | Rick Song (Co-founder and CEO)

May 8, 2025 1 hr 14 min

Rick Song is the co-founder and CEO of Persona, the identity verification platform used by some of the world’s largest companies. Before starting Persona, Rick worked on identity fraud and risk products at Square, which laid the groundwork for what would become Persona’s highly technical, horizontal platform. Since founding the company, Rick has scaled Persona into a category-defining leader, recently raising a $200M Series D at a $2B valuation. In today’s episode, we discuss: How Rick’s skepticism shaped Persona’s early strategy What it takes to scale a true platform company Successful execution in hypercompetitive markets What Rick’s learned from his co-founder, Charles Yeh and much more… Referenced: Accenture: accenture.com Anthropic: anthropic.com Braze: braze.com Bridgewater Associates: bridgewater.com Charles Yeh: linkedin.com/in/charlesyeh/ Christie Kim: linkedin.com/in/christiekimck/ Clay: clay.com Kareem Amin: linkedin.com/in/kareemamin/ MIT: mit.edu Newfront: newfront.com Palantir: palantir.com/ Persona: withpersona.com Rippling: rippling.com Scale AI: scale.com Snowflake: snowflake.com Square: squareup.com Y Combinator: ycombinator.com Zachary Van Zant: linkedin.com/in/zacharyv/ Where to find Rick: LinkedIn: https://www.linkedin.com/in/rick-song-25198b24/ 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: (0:05) Life before Persona (2:11) The push from Charles (3:09) Early reluctance and low expectations (9:50) Winning the first $50 customer (13:08)“Invalidating” Persona (16:43) How Persona found their edge (19:35) Transi...

How a weekend hack became a multimillion-dollar AI startup | Adit Abraham (Co-founder & CEO at Reducto)

Apr 29, 2025 1 hr 0 min

Adit Abraham is the co-founder and CEO of Reducto, which helps leading AI teams extract and structure data from complex documents and spreadsheets in their pipeline. Within 6 months of launching, Reducto went from 0→7 figures in ARR. Reducto has grown to process tens of millions of pages monthly for companies ranging from startups to Fortune 10 enterprises. They just announced a $24M Series A. Before Reducto, Adit was a Product Manager at Google, working on Ads and Search, and conducted machine learning research at MIT's Media Lab. --- In today’s episode, we discuss: How listening to customers revealed an opportunity to pivot The weekend project that became Reducto's breakthrough Landing a Fortune 10 customer A technical founder's guide to sales Key insights from Reducto's fundraising journey Advice for founders: “You’re going to fail” Much more --- Referenced: Anthropic: https://www.anthropic.com/ Chetan Puttagunta: https://www.linkedin.com/in/chetanputtagunta/ Diana Hu: https://www.linkedin.com/in/sdianahu/ Liz Wessel: https://www.linkedin.com/in/elizabethwessel/ Raunak Chowdhuri: https://www.linkedin.com/in/sauhaarda/ Reducto: https://reducto.ai/ Scale AI: https://scale.com/ Stripe: https://stripe.com/ Textract: https://aws.amazon.com/textract/ Y Combinator: https://www.ycombinator.com/ --- Where to find Adit: LinkedIn: https://www.linkedin.com/in/aditabraham/ --- 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: (00:00) Hackathons, YC, and an unexpected pivot (05:23) The weekend project that became Reducto's breakthrough (09:11)...

1Password’s growth story | How they went from bootstrapped to $6B company | Jeff Shiner (CEO)

Apr 24, 2025 1 hr 8 min

Jeff Shiner is the CEO of 1Password, the access management company used by over 100,000 businesses and millions of individuals worldwide. He joined 1Password as CEO in 2012, when the team was just under 20 people. Under Jeff’s leadership, 1Password expanded into B2B, launched a SaaS platform, and scaled from a small family-run operation into a global company. In 2019, Jeff led 1Password through its first-ever funding round – a $200M Series A from Accel – to build out its go-to-market team and accelerate product development. Before joining 1Password, Jeff held senior roles at IBM and led teams through multiple acquisitions and integrations. --- In today’s episode, we discuss: Why bootstrapping isn’t always what it’s cracked up to be The switch from a consumer product to B2B Launching before billing — and why that worked When being “too secure” nearly killed the product Becoming CEO… without telling anyone Much more --- Referenced: 1Password: https://1password.com Accel: https://www.accel.com Arun Mathew: https://www.linkedin.com/in/arun-mathew-b7186412/ David Teare: https://www.linkedin.com/in/daveteare/ Floodgate: https://floodgate.com LastPass: https://www.lastpass.com Mike Maples: https://www.linkedin.com/in/maples/ Natalia Karimov: https://1password.com/company/meet-the-team/natalia-karimov Roustem Karimov: https://www.linkedin.com/in/roustem/?originalSubdomain=ca Sara Teare: https://1password.com/company/meet-the-team/sara-teare Shopify: https://www.shopify.com Tobi Lütke: https://www.linkedin.com/in/tobiaslutke/ --- Where to find Jeff: LinkedIn: https://www.linkedin.com/in/jshiner --- 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/@Fi...

Scrappy tactics and a huge post-COVID pivot | Owner’s unconventional journey to product-market fit | Adam Guild (Co-founder and CEO of Owner)

Mar 27, 2025 1 hr 23 min

Adam Guild is the co-founder and CEO at Owner, an online food ordering system for independent restaurants. Within a year, Owner went from being about to run out of money to having hundreds of customers. Last year, they raised a $33M Series B. Adam’s entrepreneurial journey began as a teenager when he built a successful Minecraft server, which led him to drop out of high school to become a founder. His passion for helping small businesses was sparked by his mom’s struggles running a dog grooming shop, which led him to launch the early iteration of Owner. -- In today’s episode, we discuss: How working with a small business kickstarted Owner Adam’s unusual outbound strategy Why the pandemic accelerated Owner’s success How Owner’s pivot led to “hyperbolic” product-market fit The two qualities Adam looks for in new hires -- Referenced: Alex Bard: https://www.linkedin.com/in/alexbard/ Dean Bloembergen: https://www.linkedin.com/in/deanbloembergen/ Guisados: https://www.guisados.la/ HubSpot: https://www.hubspot.com/ Jack Altman: https://www.linkedin.com/in/jackealtman/ Kimbal Musk: https://www.linkedin.com/in/kimbalmusk/ Modern Restaurant Management: https://modernrestaurantmanagement.com/ Naval Ravikant: https://www.linkedin.com/in/navalr/ Neil Patel: https://www.linkedin.com/in/neilkpatel/ Peter Thiel: https://www.linkedin.com/in/peterthiel/ P.F. Chang's: https://www.pfchangs.com/ Sean Rad: https://www.linkedin.com/in/seanrad/ Thiel Fellowship: https://thielfellowship.org/ Tim Ferriss: https://www.linkedin.com/in/timferriss/ Y Combinator: https://www.ycombinator.com/ -- Where to find Adam: LinkedIn: https://www.linkedin.com/in/adamharrisonguild/ -- 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...

What makes (or breaks) executive hires | A deep dive with Eeke de Milliano (Head of Global Product at Stripe)

Mar 6, 2025 59 min

Eeke de Milliano is the Head of Global Product at Stripe, helping drive innovation and success in the company's product line. Before this role, she was Head of Product at Retool and co-founded Constellate. Eeke previously spent 6 years as Product Lead at Stripe, working with the company during their hyper-growth era. – In today’s episode, we discuss: Eeke’s wealth of experience as an executive leader The challenges companies face when hiring new executives Common hiring red flags and pitfalls Practical advice for measuring success Why learning your strengths is an underrated piece of the process – Referenced: ASML: https://www.asml.com/en Claire Hughes Johnson: https://www.linkedin.com/in/claire-hughes-johnson-7058/ Constellate: https://constellate.team/ John Collison: https://www.linkedin.com/in/johnbcollison/ Mike Maples Jr.: https://www.linkedin.com/in/maples/ Patrick Collison: https://www.linkedin.com/in/patrickcollison/ Retool: https://retool.com/ Stripe: https://stripe.com/ Will Gaybrik: https://www.linkedin.com/in/william-gaybrick-5730347/ – Where to find Eeke: LinkedIn: https://www.linkedin.com/in/eeke-de-milliano-3b05a629/ – 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: (00:00) Should you ‘buy or build’ a leader (03:45) Why do executive hires fail so often? (09:35) Why the stakes are so high for leadership hires (12:26) The hardest document Eeke ever wrote (14:06) Two red flags in a new hire (17:27) An example of an outstanding leader (21:40) What creates dysfunctional exec relationships (22:38) The three steps towards hiring successful leaders (30:30) What you s...

Inside Guideline's mission to modernize 401(k)s | Building from first principles, finding strategic edges, and rewiring retirement | Kevin Busque (Co-founder and CEO)

Feb 20, 2025 1 hr 24 min

Kevin Busque is the co-founder and CEO of Guideline, a 401(k) management company revolutionizing the retirement space for small and medium-sized businesses. Prior to Guideline, Kevin co-founded Taskrabbit, where he encountered firsthand the complexity and low participation rates of traditional 401(k) plans—largely due to confusing fee structures. After launching Guideline to address those problems head-on, the company has seen remarkable growth, hitting $120 million in ARR by June 2024. In this conversation, Kevin shares pivotal moments that shaped Guideline’s trajectory, including a strategic partnership with Gusto. He also explains how his “Do the hard thing first” mindset helped the team build an industry-leading platform and disrupt an entrenched market. – Referenced: ADP: https://www.adp.com/ Aydin Senkut: https://www.linkedin.com/in/aydins/ CalSavers: https://www.calsavers.com/ DoorDash: https://www.doordash.com/ Fidelity: https://www.fidelity.com/ Guideline: https://www.guideline.com/ Gusto: https://gusto.com/ Intuit: https://www.intuit.com/ Jeremy Caballero: https://www.linkedin.com/in/jeremycaballero/ John Zimmer: https://www.linkedin.com/in/johnzimmer11/ Josh Reeves: https://www.linkedin.com/in/joshuareeves/ Mike Nelson: https://www.linkedin.com/in/mnelsonio/ Leah Solivan: https://www.linkedin.com/in/leahsolivan/ Paychex: https://www.paychex.com/ Plaid: https://plaid.com/ Taskrabbit: https://www.taskrabbit.com/ Tomer London: https://www.linkedin.com/in/tomerlondon/ – Where to find Kevin: LinkedIn: https://www.linkedin.com/in/kevinbusque/ – 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.c...

Inside Braze’s blitz to $500M in CARR | Building broad, going global, and outfoxing the competition | Bill Magnuson (Co-founder & CEO) and Kevin Wang (CPO)

Feb 6, 2025 1 hr 23 min

Bill Magnuson is the co-founder and CEO at Braze, along with Kevin Wang, who joined as employee #8 and serves as the CPO. The two MIT graduates have built Braze into a publicly listed customer engagement platform with a $4.4B market cap. In 2023, Braze surpassed $500M in CARR, and serves over 2,200 customers worldwide. Before Braze, Bill spent time at Bridgewater Associates. Kevin’s academic background is in brain & cognitive sciences, and prior to joining Braze he worked at Accenture and Brewgene. – In today’s episode, we discuss: The Braze founders’ early insights into the mobile revolution How a TechCrunch Hackathon sparked Braze's creation The journey from 1,000 beta signups to 2,200+ paying customers Breaking traditional lean startup rules Navigating early fundraising challenges Finding product market fit by “fishing in every pond” Approaching competition strategically like a boxer Much more – Referenced: Accenture: https://www.accenture.com/ Appboy: https://www.braze.com/resources/articles/appboy-social-network-for-mobile-apps Bipul Sinha: https://www.linkedin.com/in/bipulsinha/ Braze: https://www.braze.com/ Bridgewater Associates: https://www.bridgewater.com/ Jon Hyman: https://www.linkedin.com/in/jon-hyman/ Mark Ghermezian: https://x.com/markgher MIT: https://www.mit.edu/ Rubrik: https://www.rubrik.com/ WeWork: https://www.wework.com/ – Where to find Bill: LinkedIn: https://www.linkedin.com/in/billmagnuson/ Twitter/X: https://x.com/billmag – Where to find Kevin: LinkedIn: https://www.linkedin.com/in/kevin-wang-96131916/ – 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 – T...

Inside Clay's unconventional path to $1.25B: Rethinking GTM, pricing, and enterprise sales | Varun Anand (Co-founder and Head of Operations)

Jan 23, 2025 1 hr 2 min

Varun Anand is the co-founder and Head of Operations at Clay, a GTM development environment that combines data and AI to help over 5000 companies power everything from CRM enrichment to highly targeted outreach campaigns. Clay recently announced their Series B expansion, raising $40M at a $1.25B valuation. Before Clay, Varun was the Director of Operations at Newfront and the Head of Expansion at Candid. Varun also spent four years working on Hillary Clinton’s presidential campaign. – In today’s episode, we discuss: Clay’s unconventional GTM machine 3 changes that unlocked Clay's upmarket motion Layering enterprise customers on top of PLG Scrappy sales tactics: WhatsApp groups, Reddit threads, and reverse demos Thinking long-term about brand and content Building an elite team of people who are “technical enough” Clay’s contrarian take on compensation Much more – Referenced: Anthropic: https://www.anthropic.com/ Clay: https://www.clay.com/ Clay’s Series B expansion: https://www.clay.com/blog/series-b-expansion Eric Nowoslawski: https://www.linkedin.com/in/outboundphd/ Figma: https://www.figma.com/ Jesse Ouellette: https://www.linkedin.com/in/jesseoue/ Kareem Amin: https://www.linkedin.com/in/kareemamin/ Nick Merrill: https://www.linkedin.com/in/nick-merrill-64562310/ Notion: https://www.notion.com/ Oyster: https://www.oysterhr.com/ Pave: https://www.pave.com/ Rippling: https://www.rippling.com/ Snowflake: https://www.snowflake.com/ Verkada: https://www.verkada.com/ Webflow: https://webflow.com/ Yash Tekriwal: https://www.linkedin.com/in/yashtekriwal/ – Where to find Varun: LinkedIn: https://www.linkedin.com/in/vaanand/ Twitter/X: https://x.com/vxanand – 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/firstroun...

Building a 4 billion dollar data platform: Inside dbt Labs’ unconventional path | Tristan Handy (Founder and CEO, ex-RJMetrics, Squarespace)

Dec 19, 2024 55 min

Tristan Handy is the Founder and CEO at dbt Labs, a cloud-based data management platform that has raised over $400M to date, and was last valued at $4.2B in 2022. Dbt Labs has grown from just three companies using its free tool in 2016 to an ecosystem of 30,000+ enterprise users. Before founding dbt Labs, Tristan was the VP of Marketing at RJMetrics and the Director of Operations at Squarespace. – In today’s episode, we discuss: Dbt’s explosive growth The strategic pivot from consulting to a software company Unexpected strategies for building a tech category from scratch The critical moment: Why and when dbt Labs sought venture funding How to drive commercial adoption after open-sourcing Two things every founder CEO should do Much more – Referenced: Amazon Redshift: https://aws.amazon.com/redshift/ Bob Moore: https://www.linkedin.com/in/robertjmoore/ Crossbeam: https://www.crossbeam.com/ dbt Labs: https://www.getdbt.com/ Drew Banin: https://www.linkedin.com/in/drewbanin/ Jerry Colonna: https://www.reboot.io/team/jerry-colonna/ RJMetrics: https://en.wikipedia.org/wiki/RJMetrics SeatGeek: https://seatgeek.com/ Steve Ritter: https://www.linkedin.com/in/steve-ritter-69495210/ Squarespace: https://www.squarespace.com/ – Where to find Tristan: LinkedIn: https://www.linkedin.com/in/tristanhandy/ Twitter/X: https://x.com/jthandy – 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: (00:00) Introduction (02:56) The critical oversight in data analysis (05:41) Becoming an “accidental founder” (07:04) Inside the unique decision to start a consultancy (08:17) The game-changing principl...

How Figma taps into taste, simplicity, and storytelling | Yuhki Yamashita (CPO at Figma, ex-Uber, Google, Microsoft)

Dec 5, 2024 1 hr 9 min

Yuhki Yamashita is the Chief Product Officer at Figma, leading the product and design teams. Previously, he was a product and design leader at Uber, where he orchestrated the redesign of the rider and driver apps. Yuhki was also a product manager at Google (YouTube iOS app) and Microsoft (Hotmail). Additionally, he has taught introductory computer science at Harvard University. In today’s episode, we discuss: How Figma approaches new products, prioritization, and storytelling Product culture at Uber, Microsoft, Google The difference between “good” and “extraordinary” PMs Tactical advice for storytelling The “un-learning” required in new jobs and industries – Referenced: Figjam: https://www.figma.com/figjam/ Figma: https://www.figma.com/ Figma Dev Mode: https://www.figma.com/dev-mode/ Figma Slides: https://www.figma.com/slides/ – Where to find Yuhki: LinkedIn: https://www.linkedin.com/in/yuhki/ Twitter/X: https://x.com/yuhkiyam – 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 – (00:00) Introduction (02:50) Figma's early days (09:11) Product culture across companies (13:42) Knowing when to change things (17:40) How business goals impact product expansion (21:00) Advice for going multi-product (24:30) The skills of a “0 to 1” PM (27:36) Identifying entrepreneurial talent (29:06) Why aren't there more designer founders? (35:22) How Figma launches new products (41:19) “0 to 1” versus “1 to 10” talent (46:01) The role of storytelling at Figma (49:22) How Figma prioritizes product (55:11) Advice for product storytelling (59:02) “Good” vs “extraordinary” product managers (61:21) Why product simpli...

How to find customers in the Dept of Defense: From prototype to the Pentagon | Steve Blank (Hacking for Defense)

Nov 14, 2024 34 min

Steve Blank is an Adjunct Professor at Stanford University, where he co-created the "Hacking for Defense" curriculum for the Department of Defense. As a consultant to top defense and intelligence organizations, Steve brings cutting-edge strategies to the national security sector. Before entering academia, Steve built eight different startups. He helped launch the Lean Startup movement with his May 2013 Harvard Business Review cover story. Steve also authored the acclaimed business books "The Four Steps to the Epiphany" and "The Startup Owner's Manual.” This episode’s is guest host is Meka Asonye, a Partner at First Round Capital. Before joining First Round as an investor, Meka led go-to-market teams at both Stripe and Mixpanel. – In today’s episode we discuss: Commercial versus military market strategies Finding mission solution fit The hidden challenges most startups miss Building relationships in National Security The new generation of “defense founders” Much more – Referenced: Alexander Osterwalder: https://www.linkedin.com/in/osterwalder/ Department of Defense: https://www.defense.gov/ Eric Ries: https://www.linkedin.com/in/eries/ Hacking for Defense: https://hackingfordefense-prod.stanford.edu/ How Saboteurs Threaten Innovation: https://steveblank.com/2024/07/30/why-large-organizations-struggle-with-disruption-and-what-to-do-about-it/ How to find your customer in the Dept of Defense: https://steveblank.com/2024/09/17/the-directory-of-dod-program-executive-offices-and-officers-peos/ Mission Model Canvas: https://steveblank.com/2019/09/ Pete Newell: https://www.linkedin.com/in/petenewell/ Special Operations Command: https://www.socom.mil/ The Frozen Middle: https://steveblank.com/2024/07/30/why-large-organizations-struggle-with-disruption-and-what-to-do-about-it/ The Hacking for Defense Manual: https://stanfordh4d.substack.com/p/the-hacking-for-defense-manual-a The Hacking for Defense Course: https://www.h4d.us/ The lean launchpad at Stanford...

Shifting Career Altitudes: Insights from a CPO’s Journey Leading in Nearly Every Function | Anneka Gupta (Rubrik, ex-LiveRamp)

Oct 10, 2024 1 hr 9 min

Anneka Gupta is the Chief Product Officer at Rubrik, a cloud management and data security company with a US$6B market cap. Before Rubrik, Anneka spent 11 years leading various teams at LiveRamp, including product, go-to-market, and operations. In today’s episode, we discuss: How LiveRamp went from $30M to $200M ARR in 3 years Anneka’s jack-of-all-trades career Why specialist hires can backfire When leaders should get in the weeds One area every PM can improve in Rubrik’s approach to building product Much more – Referenced: Acxiom: https://www.acxiom.com/ Acxiom’s acquisition of LiveRamp: https://tinyurl.com/2shm83de Amazon: https://www.amazon.com/ Auren Hoffman: https://www.linkedin.com/in/auren/ Dentsu: https://www.dentsu.com/ Dentsu’s acquisition of Merkle: https://tinyurl.com/yvxe6fws James Arra: https://www.linkedin.com/in/james-arra-a43a06/ LiveRamp: https://liveramp.com/ Merkle: https://www.merkle.com/ Rubrik: https://www.rubrik.com/ Slack: https://www.slack.com/ Travis May: https://www.linkedin.com/in/stmay/ – Where to find Anneka Gupta: LinkedIn: https://www.linkedin.com/in/annekagupta/ Twitter/X: https://x.com/annekagupta – Where to find Brett Berson: 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: (00:00) Introduction (02:11) Inside LiveRamp’s unique growth journey (12:18) Anneka’s first PM role (14:20) Leading LiveRamp’s marketing function (16:17) Why the best product doesn’t win (21:06) Crafting products for different personas (24:53) Transitioning Acxiom’s customers to LiveRamp (33:54) Why Acxiom chose to buy not build (36:40) Anneka's leap to GM and product leader (38:22) H...

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Competing with OpenAI and Meta for your inbox | Jean-Denis Greze (Town Co-founder & CEO)

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Podcast details

Created by: First Round
Status: Active
Latest episode: Oct 28, 2026
Episodes: 186
Release period: Every two weeks
Avg. episode length: 1 hr 4 min
Explicit: No
Language: English

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