Matt MacInnis is the COO at Rippling, an all-in-one HR, IT, and finance platform for businesses, which last raised $500M at a $11.25B valuation. Before Rippling, Matt was the co-founder and CEO at Inkling, a mobile learning platform that was acquired in 2018. He also held several management roles at Apple. — In today’s episode, we discuss: Lessons on culture, org-design, and product from Rippling Characteristics of great CEOs How to a better executive leader Leading with kindness and impatience How to fight entropy — Referenced: Andy Roddick: https://www.atptour.com/en/players/andy-roddick/r485/overview Apple: https://www.apple.com Bain & Company: https://www.bain.com/ Bill Campbell: https://en.wikipedia.org/wiki/Bill_Campbell_(business_executive) Conscious Business: https://www.amazon.com.au/Conscious-Business-Build-Value-Through/dp/1622032020 Google: https://www.google.com Inkling: https://www.inkling.com/ McCaw Cellular: https://en.wikipedia.org/wiki/McCaw_Cellular_Communications McKinsey: https://www.mckinsey.com/ Microsoft: https://www.microsoft.com Oracle: https://www.oracle.com Parker Conrad: https://www.linkedin.com/in/parkerconrad/ Peter Currie: https://en.wikipedia.org/wiki/Peter_Currie_(businessman) Rippling: https://www.rippling.com The Effective Executive: https://www.amazon.com.au/Effective-Executive-Peter-Ferdinand-Drucker/dp/0060833459 — Where to find Matt MacInnis: LinkedIn: https://www.linkedin.com/in/macinnis/ Twitter/X: https://twitter.com/stanine — 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 (02:14) Great CEOs don’t worry about their weaknesses (06:31) The third-time founder mindset (08:09) Why every great CEO is impatient (11:54) How executives fight entropy (19:11) Experience ≠ wisdom (21:26) Managing workplace politics (24:02) Why all businesses should dogfood (26:20) Overseeing employee expenses (27:43) The best CEOs don’t need coaching (29:55) The hidden cost of advice (40:40) Why execs are “tortured but happy” (44:16) Clear versus first principles thinking (51:09) Finding first principles thinkers (53:13) Why people overcomplicate culture (55:53) Don’t make this mistake when interviewing (59:26) The importance of anti-patterns (61:27) Important business values (63:28) How Matt thinks about output (66:33) Rippling’s key leadership principle (71:02) Why kindness matters (72:03) Freeing yourself from self-doubt

Alyssa Henry is the former CEO of Square, a financial services company providing products and services used by over 4 million merchants. Formerly at Amazon, Alyssa led the development and growth of Simple Storage Service (S3) at AWS. Alyssa now serves as an Independent Director at Intel and Confluent. —  In today’s episode, we discuss: Lessons from Amazon, Microsoft, and Square “Minimum Remarkable Products” versus Minimum Viable Products Navigating different work cultures in big tech Insider reactions to the disruptive launch of AWS “Pioneer” versus “fast-follower” companies —  Referenced: Amazon: https://www.amazon.com Amazon Web Services: https://aws.amazon.com Bill Gates: https://www.linkedin.com/in/williamhgates Block, Inc: https://block.xyz Cash App: https://cash.app Fast Company - Back To Square One: https://www.fastcompany.com/3033412/back-to-square-one Gokul Rajaram: https://www.linkedin.com/in/gokulrajaram1 Jack Dorsey: https://twitter.com/Jack James Hamilton: https://www.linkedin.com/in/jameshamilton4 Jeff Bezos: https://twitter.com/jeffbezos Microsoft: https://www.microsoft.com Oracle Corporation: https://www.oracle.com Sarah Friar: https://www.linkedin.com/in/sarah-friar Square: https://squareup.com Tom Szkutak: https://www.linkedin.com/in/tom-szkutak-4b59817 WSJ - Mobile-Payments Startup Square Discusses Possible Sale: https://www.wsj.com/articles/SB10001424052702303825604579513882989476424 —  Where to find Alyssa Henry: LinkedIn: https://linkedin.com/in/alyssa-henry-0905692 Twitter/X: https://twitter.com/alyssahhenry —  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: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast —  Timestamps: (00:00) Introduction (02:20) Lessons from Microsoft and Amazon (08:29) Noticeable consistencies in the human condition (10:50) Differences in culture at Amazon, Microsoft and Square (13:27) Why “customers come first,” even above employees and community (14:01) Why fast-followers can be less customer-focused (15:50) The challenge of commercializing research projects (18:58) Joining Square and “building a picture” of the org (24:55) Knowing what to replicate from past companies (27:45) Questioning norms in new companies (28:41) The importance of effective communication systems (31:31) How to operationalize company values (33:38) Why shared beliefs are crucial for good company culture (37:05) Building Minimal Remarkable Products at Square (38:13) How to scale an aesthetic (42:46) Org design lessons from Square (50:06) How to align different teams behind business priorities (52:57) Lessons learned from fierce competition (57:39) The “fast follower” vs “pioneer” playbook (61:05) The original thinking behind AWS (66:08) The unlikely origin of Amazon CloudFront and other products (73:47) How Jeff Bezos influenced Alyssa

Adam Nash is the co-founder and CEO at Daffy, a platform that makes it easier to donate to charities and non-profits. Before Daffy, Adam was the President and CEO at Wealthfront, where he scaled the company’s assets under management from $100M to over $4B. Adam has also held leadership and technical roles at Dropbox, LinkedIn, eBay, and Apple. — In today’s episode, we discuss: Why founders should build platforms, not apps The importance of “delighting” customers How Daffy is disrupting donor-advised-funds Lessons on strategy from LinkedIn How to think about leadership transitions — Referenced: Andy Rachleff: https://www.linkedin.com/in/rachleff/ Bill Gates: https://www.linkedin.com/in/williamhgates/ Daffy: https://www.daffy.org/ Daffy’s 2023 Year in Review: https://www.daffy.org/resources/year-in-review-2023 eBay: https://www.ebay.com/ Jeff Weiner: https://www.linkedin.com/in/jeffweiner08/ Reid Hoffman: https://www.linkedin.com/in/reidhoffman/ Robinhood: https://robinhood.com/ Ryan Roslansky: https://www.linkedin.com/in/ryanroslansky/ The Innovator’s Dilemma: https://www.amazon.com/Innovators-Dilemma-Clayton-M-Christensen/dp/0062060244 Tim Cook: https://www.apple.com/leadership/tim-cook/ Wealthfront: https://www.wealthfront.com/ — Where to find Adam Nash: LinkedIn: https://www.linkedin.com/in/adamnash/ Twitter/X: https://twitter.com/adamnash — 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: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:08) Why the last 10 years have been less disruptive (06:15) Why we think about luck wrong (08:39) How eBay survived the dot com bubble (14:37) The value of building platforms, not apps (22:18) What made LinkedIn successful (27:31) Good company strategy = good product strategy (30:58) Setting LinkedIn’s strategy in 2009 (36:41) Why KaChing didn’t work (40:56) Pivoting to Wealthfront (43:23) Universal lesson on customer acquisition (45:11) Treating growth like a product problem (49:01) Advice on successful leadership transitions (54:20) How to delegate moral authority (60:24) The problem with metrics and customer requests (66:41) Apple’s approach to “delighting” customers (69:16) The 70/20/10 rule you’ve never heard about (70:29) How Daffy ships “delight features”

Eilon Reshef is the co-founder and CPO at Gong, an AI-powered platform that tracks, records, and analyzes sales calls to drive revenue growth. In 2021, Gong raised $250M at a $7.25B valuation. Gong was one of the fastest SaaS companies to hit $100m ARR, and now has over 4000 customers. Before Gong, Eilon sold his previous e-commerce startup, Webcollage. — In today’s episode, we discuss: Why Eilon was so bullish on recording sales calls How Gong knew they had product market fit The importance of design partners Expanding into multi-product offerings Lessons from riding the AI wave since 2015 The future of AI in B2B sales efficiency — Referenced: Act-On Software: https://act-on.com/ Amit Bendov: https://www.linkedin.com/in/amitbendov/ BlueJeans: https://www.bluejeans.com/ Crossing the Chasm: https://www.amazon.com/Crossing-Chasm-3rd-Geoffrey-Moore/dp/0062292986 Gong: https://www.gong.io/ Mistral: https://mistral.ai/ OpenAI: https://openai.com/ Salesforce: https://salesforce.com/ Webcollage: https://www.crunchbase.com/organization/webcollage Webex: https://www.webex.com/ Zoom: https://zoom.us/ — Where to find Eilon Reshef: LinkedIn: https://www.linkedin.com/in/eilonreshef/ — Where to find Todd Jackson: LinkedIn: https://www.linkedin.com/in/toddj0/ Twitter/X: https://twitter.com/tjack — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:32) Eilon’s unwavering conviction in Gong (09:34) Initial reactions to Gong’s demo (13:48) Keeping the beta lean (15:33) Gong’s monetization strategy (16:38) Early signs of product market fit (18:14) The importance of design partners to Gong’s growth (21:52) Why VCs were afraid to invest (23:43) Reaching 100 customers (26:10) Eilon’s unique product roadmap framework (28:22) Going from $2M to $9M ARR in one year (29:02) The journey to multi-product (30:52) How Gong measures success (34:07) Lessons from building AI products for sales (37:45) Predicting the future of B2B sales (38:48) The concept of “raving fans” (39:31) Why it’s “easier” for second-time founders (42:00) Eilon’s favorite books (42:45) Gong in 2024

Dennis Pilarinos is the founder and CEO at Unblocked, a developer tool that lets you talk to your codebase. In 2018, Dennis’ first company, Buddybuild, was acquired by Apple, and he was subsequently appointed Director of Development Technologies. Before that, Dennis was a Senior Director at AWS and a Director at Microsoft. — In today’s episode, we discuss: Lessons on culture and product from Amazon, Apple, and Microsoft Building and scaling DevTools Finding product market fit and monetizing it Why AI is complicating product market fit How Dennis prioritizes mental health as a founder The common mistake people make when hiring — Referenced: Apple’s acquisition of Buddybuild: https://www.cnbc.com/2018/01/02/apple-agrees-to-buy-buddybuild.html AWS: https://aws.amazon.com Bitbucket: https://bitbucket.org Confluence: https://www.atlassian.com/software/confluence GitHub: https://github.com GitLab: https://gitlab.com Looker: https://looker.com Microsoft Azure: https://azure.microsoft.com Stewart Butterfield: https://www.linkedin.com/in/butterfield/ Stripe: https://stripe.com Twilio: https://twilio.com Unblocked: https://getunblocked.com/ — Where to find Dennis Pilarinos: LinkedIn: https://www.linkedin.com/in/dennispi Twitter/X: https://twitter.com/dennispilarinos — 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: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:18) Why building for developers is different (07:28) Buddybuild’s origin story (10:40) Early signs of product market fit (12:22) Managing mental health as a second-time founder (21:09) Building and scaling Unblocked (29:52) Dennis’ cautious take on AI (34:20) Being customer-obsessed (35:25) Unblocked’s decision-making process (38:31) Don’t over-index on competency when hiring (43:36) Why great product is everything (45:41) Monetizing product market fit (48:21) The power of positioning (51:48) Why Dennis doesn’t do demos (54:45) How to deal with customer feedback (57:29) Stewart Butterfield’s impact on Dennis

May Habib is the co-founder and CEO of Writer, a full-stack generative AI platform built for enterprises. The model is trained on a customer’s own data to create content that is consistent with their brand style and voice. Writer recently raised $100M at a valuation of around $500M. Prior to Writer, May co-founded Qordoba, an AI writing assistant. —  In today’s episode, we discuss: Advice for AI founders in 2024 Why it’s difficult to scale AI products for enterprise The secret to finding champions Signs of a healthy co-founder relationship The future of agentic AI —  Referenced: Accenture: https://www.accenture.com ChatGPT: https://chat.openai.com/ Dropbox: https://www.dropbox.com Goldman Sachs: https://www.goldmansachs.com/ Grammarly: https://www.grammarly.com Jill Kramer: https://www.linkedin.com/in/jill-kramer-64230840/ L’Oreal: https://www.loreal.com/ Northwestern Mutual: https://www.northwesternmutual.com/ Palmyra: https://writer.com/blog/palmyra/ Retrieved Augmented Generation: https://blogs.nvidia.com/blog/what-is-retrieval-augmented-generation/ United Healthcare: https://www.uhc.com/ Vanguard: https://global.vanguard.com/ Waseem Alshikh: https://www.linkedin.com/in/waseemalshikh/ Writer: https://writer.com/ —  Where to find May Habib: LinkedIn: https://www.linkedin.com/in/may-habib/ Twitter/X: https://twitter.com/may_habib —  Where to find Todd Jackson: LinkedIn: https://www.linkedin.com/in/toddj0/ Twitter/X: https://twitter.com/tjack —  Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast —  Timestamps: (00:00) Introduction (02:34) Writer’s origin story (06:30) Building a full-stack generative AI platform for enterprise (11:56) The #1 challenge building Writer (15:41) Writer’s approach to finding champion customers (20:29) How Writer is winning the enterprise space (27:11) Signs Writer found product-market-fit (29:26) Scaling LLMs for specific use cases (31:53) Writer’s goals for 2024 (33:57) Advice for 0 to 1 founders (35:53) Creating a culture of “connect, challenge, and own”

Amjad Masad is the co-founder and CEO of Replit, an online platform designed for collaborative coding in multiple programming languages. Replit boasts over 30m users, has secured $200M in venture funding, and was recently valued at $1.2B. Before Replit, Amjad was a Software Engineer at Facebook, and a Founding Engineer at Codecademy. — In today’s episode, we discuss: How AI is reshaping the software landscape Bridging the gap between ideas and software Why YC almost rejected Replit four times Replit’s fundraising difficulties, and how Paul Graham helped The secret lever Replit pulled to scale ahead of its competition Replit’s impressive distribution engine — Referenced: 7 Powers: https://www.amazon.com/7-Powers-Foundations-Business-Strategy/dp/0998116319/ Codecademy: https://www.codecademy.com/ Hacker News: https://news.ycombinator.com/ I Am a Strange Loop: https://www.amazon.com/Am-Strange-Loop-Douglas-Hofstadter/dp/0465030793 Mythical Man-Month: https://www.amazon.com/Mythical-Man-Month-Software-Engineering-Anniversary/dp/0201835959 On the Naturalness of Software: https://people.inf.ethz.ch/suz/publications/natural.pdf OpenAI: https://openai.com/ Paul Graham: https://twitter.com/paulg Python: https://www.python.org/ Read Write Own: https://www.amazon.com/Read-Write-Own-Building-Internet/dp/0593731387/ Replit: https://replit.com/ Roy Bahat: https://www.linkedin.com/in/roybahat/ Sam Altman: https://twitter.com/sama The Innovator’s Dilemma: https://www.amazon.com/Innovators-Dilemma-Technologies-Management-Innovation/dp/1633691780/ The Little Schemer: https://www.amazon.com/Little-Schemer-Daniel-P-Friedman/dp/0262560992/ Y Combinator: https://www.ycombinator.com/ — Where to find Amjad Masad: LinkedIn: https://www.linkedin.com/in/amjadmasad Twitter/X: https://twitter.com/amasad — Where to find Todd Jackson: LinkedIn: https://www.linkedin.com/in/toddj0/ Twitter/X: https://twitter.com/tjack — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:31) Replit’s origin story (08:24) Starting Facebook’s JavaScript infrastructure team (10:36) Amjad’s unique path to entrepreneurship (16:04) How Replit got its early users (17:00) Replit’s fundraising difficulties (17:54) Why YC almost rejected Replit four times (20:23) Building Replit’s distribution engine (22:08) Drivers of Replit’s growth (27:41) What Silicon Valley gets wrong (30:09) Replit’s monetization strategy (32:29) Integrating AI into the platform (36:18) The impact of AI on software engineering (39:40) Defining the new “software creator” role (41:43) How to keep up with developments in AI (46:24) Replit’s goals for 2024 (48:11) Advice for founders: defy conventional wisdom (51:12) Amjad’s 4 favorite books

Michael Cieri is the Chief Product Officer at Gusto, an HR and payroll platform used by more than 300,000 businesses. With a decade of experience, he has led successful SMB product development and scaled high-performing orgs. Before Gusto, Michael was also the Head of Product at Square, where he led a team of 15+ PMs responsible for $600m in annual revenue. Michael was also the VP of Product Management at Opendoor. — In today’s episode, we discuss: Key product strategies used by Square and Gusto The pros and cons of building for SMBs How to build horizontal after creating a wedge The catch with building vertical SaaS How product teams can move faster Developing product sense and intuition — Referenced: Alyssa Henry: https://www.linkedin.com/in/alyssa-henry-0905692/ Copilot: https://copilot.microsoft.com/ Gokul Rajaram: https://www.linkedin.com/in/gokulrajaram1/ Gusto: https://gusto.com/ High Output Management: https://amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884 Marty Cagan: https://www.linkedin.com/in/cagan/ Opendoor: https://www.opendoor.com/ Silicon Valley Product Group: https://www.svpg.com/ Square: https://squareup.com/ The Three Horizons Model: https://www.mckinsey.com/enduring-ideas-the-three-horizons-of-growth Toast: https://pos.toasttab.com/ — Where to find Michael Cieri: LinkedIn: https://www.linkedin.com/in/michaelcieri/ — 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: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:41) Why SMBs require unique software solutions (05:58) The level of specificity required when building for SMBs (08:47) Finding Square’s form-fitting solution (11:48) Building vertical versus horizontal SaaS (14:34) Inside Square and Gusto’s decision making framework (16:15) How to build horizontally from a wedge product (23:00) Using the Three Horizons Model (25:29) How to craft a compelling vision for products (28:51) How to assess Horizon 3 bets (32:08) How to give employees the freedom to try things (34:24) Creating a risk-taking culture (37:27) Essential advice for new PMs (40:27) Common thread with bad product pitches (42:29) Applying the Horizon framework at Gusto (44:46) Developing good product sense (47:43) 5 signs of great product sense (49:03) Why product sense is like athletic ability (51:43) How to ship faster without increasing headcount (56:10) People who had an outsized impact on Michael

Stephanie Berner is a Customer Success Executive at LinkedIn. Since 2018, Stephanie has spearheaded all post-sales functions at LinkedIn Sales Solutions through its period of rapid growth. With a background in building and scaling customer success teams at Box, Medallia, and Opower, Stephanie has extensive experience in delivering exceptional customer experiences across various company stages. — In this episode, we discuss: Common customer success mistakes Creating a world-class customer success org Tactics for hiring exceptional talent How to structure compensation packages Where customer success fits into the wider org Key early-stage customer success metrics and rituals Successful strategies from Box, Medallia, and LinkedIn — Referenced: Aaron Levie: https://www.linkedin.com/in/boxaaron/ Box: https://www.box.com/ David Love: https://www.linkedin.com/in/david-s-love/ Gainsight: https://www.gainsight.com/ Jon Herstein: https://www.linkedin.com/in/jonherstein/ Jonathan Lister: https://www.linkedin.com/in/jonathanlister/ Ken Fine: https://www.linkedin.com/in/kmfine/ Medallia: https://www.medallia.com/ Nick Mehta: https://www.linkedin.com/in/nickmehta/ Opower: https://www.oracle.com/utilities/opower-energy-efficiency/ — Where to find Stephanie Berner: LinkedIn: https://www.linkedin.com/in/stephanieberner/ — 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: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:21) Formalizing customer success at a startup (05:01) Hiring ICs before CSMs (06:22) Tactics for hiring standout talent (11:39) 3 questions to ask candidates (15:38) Fail-case patterns among customer success hires (17:49) Considering candidates with non-traditional backgrounds (21:21) Indexing toward a bias for action (24:17) What v1 of customer success looks like (26:03) Key early-stage customer success metrics (28:21) Whether customer success or sales should own renewals (30:40) Where customer success fits into the org (32:14) Why customer success doesn’t report to an executive (33:48) Distinguishing a product problem from a customer success one (35:18) Simple way to deal with customer churn (39:21) Tactics to get customers to give honest feedback (40:58) What happens when customer success and product teams collaborate (44:14) Rituals for zero-to-one customer success (48:23) How to structure an early customer success team (52:01) Structuring compensation packages (54:35) Aligning customer success with the business model (60:14) The role of customer success in B2B software (62:17) Common customer success mistakes (67:44) People who had an outsized impact on Stephanie

Michael Lopp is an experienced engineering leader known for building products at iconic companies like Apple, Borland, Netscape, Palantir, and Slack. Since 2002, Lopp — as he’s more commonly known — has written about engineering, management, and leadership on his popular blog ‘Rands in Repose’. He is also the renowned author of three books: Being Geek, Managing Humans, and The Art of Leadership. — In today’s episode, we discuss: Lopp’s “utopia” — where engineers have time to create and invent What makes an excellent engineering leader The flexibility required for managerial roles in different contexts Navigating internal dynamics between design, engineering, and product How to build and grow effective engineering orgs The importance of understanding individual motivations Key lessons from over 30 years in the industry — Referenced: AOL: https://aol.com Apple: https://www.apple.com Borland: https://en.wikipedia.org/wiki/Borland Netscape: https://en.wikipedia.org/wiki/Netscape Palantir: https://www.palantir.com/ Phillipe Kahn: https://www.linkedin.com/in/philippekahn/ Pinterest: https://www.pinterest.com/ Slack: https://slack.com Stewart Butterfield: https://www.linkedin.com/in/butterfield/ Tom Paquin: https://www.linkedin.com/in/tom-paquin-240b4b2/ — Where to find Michael Lopp: Blog: https://randsinrepose.com/ LinkedIn: https://www.linkedin.com/in/michaellopp/ Twitter/X: https://twitter.com/rands — 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: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:20) Beginning career at Borland (05:41) The difficulty with shipping software at scale (07:52) Why it’s harder to ship today than ever before (09:42) What makes a startup operationally sound (11:23) Why engineers should have concrete time to invent (19:42) How PMs can improve engineering culture (21:35) An engineer’s perspective on good product management (23:36) The role of product compared to design and engineering (26:38) How micromanagement kills creativity (29:35) Fostering a debate culture in an org (31:26) Declarative versus prescriptive leadership (36:09) 3 ideas on leadership from Lopp’s upcoming book (38:29) Understanding employee motivation (42:28) Advice on discovering what motivates people (46:06) Why teams should reorg every 6 months (48:32) One thing all successful leaders do (52:22) Why sound judgment is crucial for decision-making (53:45) Crystallized lessons from working at software giants (56:19) Why Lopp is afraid of becoming irrelevant (57:58) The number one leadership lesson from Lopp’s career (59:32) What Lopp has changed his mind on over time (61:12) People who had an outsized impact on Lopp

Kareem Amin is the co-founder of Clay, a lead-generation software that uses AI to scrape 50+ databases and help companies scale their outbound campaigns. Before Clay, Kareem was the VP of Product at The Wall Street Journal. Kareem also co-founded Frame (useframe.com) which was acquired by Sailthru in 2012. — In today’s episode, we discuss: Creating a community of power users How to stay ruthlessly focused and make decisions faster Clay’s principles for finding product-market-fit Why a company is the reflection of its founder’s personality Aligning your own psychology with the business The mindset change from a first to second-time founder — Referenced: Airtable: https://www.airtable.com/ Clay: https://www.clay.com/ Figma: https://www.figma.com/ Internal Family Systems: https://ifs-institute.com/ NetSuite: https://www.netsuite.com/ Notion: https://www.notion.com Sailthru: https://www.sailthru.com/ — Where to find Kareem Amin: LinkedIn: https://www.linkedin.com/in/kareemamin/ Twitter/X: https://twitter.com/kareemamin — Where to find Todd Jackson: LinkedIn: https://www.linkedin.com/in/toddj0/ Twitter/X: https://twitter.com/tjack — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:36) Clay’s origin story (05:54) Building for a specific customer (10:42) Knowing when to build for a broader customer-base (12:46) The life spiral framework (15:52) How founders can make better decisions (18:57) Kareem’s principles for product-market-fit (25:36) Clay’s customer journey (30:04) Interesting tactic to find power users (34:00) How to know you have product-market-fit (37:11) The impact of founder psychology on the business (39:41) Mastering commitment to sprints (40:47) How Kareem’s own personality affected his company (43:31) Actionable advice to understand founder psychology (46:25) Why focus is misunderstood (47:09) The mindset shift from a first to second-time founder (50:28) What’s next for Clay (52:14) The best piece of advice Kareem has actioned

Kyle Parrish, Figma’s first sales hire, built the company’s zero-to-one sales engine from scratch. Figma now has more than 3 million monthly users. Prior to Figma, Kyle spent 5 years at Dropbox in various sales roles. At Dropbox, Kyle successfully launched and scaled the Austin office to 100+ people, and then led the enterprise sales function in San Francisco and New York. — In today’s episode, we discuss: The right time to build a sales function Hiring and scaling a successful sales org Building a unique sales culture Career advice for ambitious salespeople Figma’s early sales motion How to integrate your first sales hire Navigating the founder/Head of Sales relationship — Referenced: Amanda Kleha: https://www.linkedin.com/in/amanda-kleha-015599/ Asana: https://asana.com/ Atlassian: https://www.atlassian.com/ Claire Butler: https://www.linkedin.com/in/clairetbutler/ Dropbox: https://www.dropbox.com/ Dylan Field: https://www.linkedin.com/in/dylanfield/ FigJam: https://www.figma.com/figjam/ Figma: https://www.figma.com/ Kevin Egan: https://www.linkedin.com/in/kevin-egan-59719/ Oliver Jay: https://www.linkedin.com/in/oliverjayleadership/ Praveer Melwani: https://www.linkedin.com/in/praveer-melwani/ Salesforce: https://www.salesforce.com/ Slack: https://www.slack.com/ — Where to find Kyle Parrish: LinkedIn: https://www.linkedin.com/in/kparrish8/ Twitter/X: https://twitter.com/KyleHParrish — 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: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:10) What founders need to figure out before hiring salespeople (03:48) Who to hire as your first salesperson (05:34) Transitioning away from founder-led sales (07:07) Tactics for hiring great salespeople (12:50) The ideal experience sales candidates should have (13:49) Common traits of successful salespeople (18:45) What it was like being Figma’s first sales hire (19:59) Interesting tactic to integrate the first sales hire (21:16) How Figma executed its early sales motion (32:27) Why Figma changed its customer narrative (34:03) Building outbound sales strategy at Figma (36:17) Segmented pricing and no discounts (41:55) Kyle’s transition from Dropbox to Figma (47:25) Creating a world-class sales culture (51:46) How Figma does sales differently (54:02) Building the initial sales team around a passion for the product (57:12) Figma’s unique hiring process for salespeople (60:40) Advice for founders hiring their first salesperson (63:18) The secret to Dylan Field’s success (64:33) How to scale yourself as an early hire (66:25) Oliver Jay’s impact on Kyle

Oliver Jay is a sales and expansion specialist. Oliver was Chief Revenue Officer at Asana and led the company’s global expansion. He grew the team from 20 to 450 people and increased international income to 40% of Asana’s total revenue. Prior to this, Oliver built the first business sales team at Dropbox, and led the company’s expansion into the Asia-Pacific region while tripling ARR. Oliver is now an advisor and leadership coach focused on assisting founders and executives in scaling their businesses. — In today’s episode, we discuss: Common mistakes PLG companies make The “PLG trap” and how to avoid it The playbook for transitioning into enterprise How and when to build an enterprise sales team How PLG companies can break $10 billion market cap Why it’s difficult to emulate Atlassian, Slack or Salesforce — Referenced: Airtable: https://www.airtable.com/ Asana: https://asana.com/ Atlassian: https://www.atlassian.com/ Bitbucket: https://bitbucket.org/product/ Confluent: https://www.confluent.io/ Daniel Shapero: https://www.linkedin.com/in/dshapero/ Datadog: https://www.datadoghq.com/ Dennis Woodside: https://www.linkedin.com/in/dennis-woodside-341302/ Dropbox: https://www.dropbox.com/ Dustin Moskovitz: https://www.linkedin.com/in/dmoskov/ Jay Simons: https://www.linkedin.com/in/jaysimons/ Jira: https://www.atlassian.com/software/jira Justin Rosenstein: https://www.linkedin.com/in/justinrosenstein/ Kim Scott: https://www.linkedin.com/in/kimm4/ Salesforce: https://www.salesforce.com/ Slack: https://slack.com/ The PLG Trap: https://www.linkedin.com/pulse/plg-trap-oliver-jay/ The seed, land, and expand framework: https://www.endgame.io/blog/seed-land-expand-framework Zendesk: https://www.zendesk.com/ — Where to find Oliver Jay: LinkedIn: https://www.linkedin.com/in/oliverjayleadership/ Website: https://www.oliverjayleadership.com/ — Where to find Brett Berson: Twitter/X: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094 — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:23) Differences between PLG and enterprise companies (05:56) Avoiding the “PLG trap” (07:39) Transitioning to enterprise feels like building two companies (10:57) Thinking about user value versus company value (13:58) The relationship between OKRs and executive champions (14:59) Dropbox had almost no company value (15:33) The strategy PLG companies should avoid (18:30) Why Dropbox is worth $10b, not $50b (19:41) The story of Asana’s expansion (21:16) Asana’s unique customer success team (23:27) How product strategy relates to finding champions (25:03) How Asana structured its GTM org (27:11) What Oliver would have done differently with Asana’s GTM (29:45) Getting executive-level buy-in (31:49) Asana’s concept of “selling clarity” (33:18) An inside look at Asana’s transition into enterprise (37:59) The champion tree framework (40:43) Structuring Asana’s early enterprise sales team (44:27) The impact of company size on GTM (47:20) Common sales mistake (48:29) The seed, land, and expand framework (51:43) Oliver’s advice to founders (54:13) Why building horizontally may be a mistake (55:32) Common challenges faced by PLG companies (58:30) How PLG companies can break the $10b market cap (60:17) Why emulating Atlassian’s playbook is difficult (63:21) People who had an outsized impact on Oliver

Steve Blank, an Adjunct Professor at Stanford University, is widely regarded as the father of modern entrepreneurship. Prior to academia, Steve’s career spanned eight different startups. Credited with launching the Lean Startup movement with his May 2013 Harvard Business Review cover story, Steve has changed how startups are built, and how entrepreneurship is taught. Steve is also the renowned author of The Four Steps to the Epiphany and The Startup Owner’s Manual. — In today’s episode, we discuss: Why there aren’t more successful startups How to improve entrepreneurship in the USA Misunderstood aspects of the Lean Startup methodology Common traits shared by outlier founders Why successful entrepreneurs are irrational (and need to be) How founders can transition to CEOs Why some second-time founders fail Building in existing versus new markets The Four Steps to the Epiphany in 2023 — Referenced: Alexander Osterwalder: https://www.linkedin.com/in/osterwalder Allen Michels: https://en.wikipedia.org/wiki/Allen_Michels Ben Wegbreit, Co-founder of E.piphany: https://www.linkedin.com/in/ben-wegbreit-22192/ Convergent Technologies: https://en.wikipedia.org/wiki/Convergent_Technologies Eric Ries: https://www.linkedin.com/in/eries/ Gordon Bell: https://www.linkedin.com/in/gordon-bell-3035b43/ JB Straubel: https://www.linkedin.com/in/jb-straubel-b694981/ Kathy Eisenhardt: https://www.linkedin.com/in/kathleen-eisenhardt-5642247/ Roger Siboni, former CEO of E.piphany: https://theorg.com/org/coupa-software/org-chart/roger-siboni Satya Nadella: https://www.linkedin.com/in/satyanadella/ Steve Ballmer: https://www.linkedin.com/in/steve-ballmer-7087a8157/ The lean launchpad at Stanford: https://steveblank.com/2011/05/10/the-lean-launchpad-at-stanford-–-the-final-presentations/ The semiconductor industry - explained: https://steveblank.com/2022/01/25/the-semiconductor-ecosystem/ The three pillars of world class corporate innovation: https://steveblank.com/2022/11/11/the-three-pillars-of-world-class-corporate-innovation/ Tina Seelig: https://www.linkedin.com/in/tinaseelig/ Tom Mueller, Ex-SpaceX Propulsion CTO: https://www.linkedin.com/in/thomas-mueller-2094513b/ Why corporate entrepreneurs are extraordinary: https://steveblank.com/2015/08/25/why-corporate-entrepreneurs-are-extraordinary-the-rebel-alliance/ Why entrepreneurs start companies rather than join them: https://steveblank.com/2018/04/11/why-entrepreneurs-start-companies-rather-than-join-them/ — Where to find Steve: LinkedIn: https://www.linkedin.com/in/steveblank/ Twitter/X: https://twitter.com/sgblank Website: https://steveblank.com/ — 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: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:20) Why there aren’t more successful startups (06:07) Outlier founders have similar childhoods (10:34) How to be a successful founder CEO (12:00) Why entrepreneurship should be taught in schools (16:39) The importance of curiosity (19:57) The role of instincts in entrepreneurship (22:31) Having profound beliefs in a vision (24:17) Building in existing versus new markets (29:09) What second-time founders can get wrong (33:49) Why founders need to be irrational (39:28) Common traits shared by outlier founders (45:05) Evaluating what makes a startup successful (49:44) Steve’s assessment of Satya Nadella at Microsoft (52:26) What it takes to build an incredible company (60:45) The Four Steps to the Epiphany in 2023 (64:36) The origins of The Four Steps to the Epiphany

Neha Narkhede is a co-founder at Confluent, a data streaming software that raised at a $9.1b valuation in 2021. Neha later co-founded Oscilar, a no-code platform that helps companies detect and manage fraud. Before building these two companies, Neha was a Principal Software Engineer at LinkedIn where she co-created Apache Kafka. Neha is ranked #50 on Forbes’ list of “America’s Richest Self-Made Women 2023” with an estimated net worth of $520m. — In today’s episode we discuss: The origins of Confluent, Kafka, and Oscilar How to become a successful second-time founder Advice for monetizing open source product Neha’s unique GTM strategies How Confluent ran two businesses within one company Neha’s path to founder market fit — Referenced: Apache Kafka: https://kafka.apache.org/ Confluent: https://www.confluent.io/ Confluent Cloud: https://www.confluent.io/confluent-cloud/ Jay Kreps, co-founder at Confluent: https://www.linkedin.com/in/jaykreps/ Jun Rao, co-founder at Confluent: https://www.linkedin.com/in/junrao/ MongoDB: https://www.mongodb.com/ Oscilar: https://oscilar.com/ — Where to find Neha: LinkedIn: https://www.linkedin.com/in/nehanarkhede/ Twitter/X: https://twitter.com/nehanarkhede Website: https://www.nehanarkhede.com/ — 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: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:14)The origin story of Kafka (05:24) Co-creating Kafka at LinkedIn (07:31) Why open sourcing Kafka was a masterstroke (11:04) The unique nature of Confluent's Zero to One phase (16:35) Building for a specific customer early on (18:42) Inside Confluent’s successful launch (20:12) Establishing Confluent as an enterprise company (22:00) The role of developer evangelism in Confluent’s success (23:49) Using developer evangelism in category creation (26:41) Navigating early co-founder dynamics (30:06) Leveraging complementary founder skills (31:56) Advice for future founders (32:45) Building Confluent with monetization in mind (34:38) Monetizing open source products (36:05) GTM for subscription Saas versus consumption SaaS (39:48) The importance of founder-led GTM sales (40:58) Neha’s order of operations for GTM sales (42:33) When to build out outbound sales (45:28) Adding SaaS to a software business (49:48) Choosing what to license and what to open source (53:32) How Confluent’s co-founders decided on SaaS offering (57:58) Neha’s journey as a second-time founder (59:48) Building Oscilar differently to Confluent (64:15) Going from speculation to product realization (70:00) Solving problems people are willing to pay for (72:07) Neha’s “proactive research sprint” tactic (73:48) How Neha has applied this tactic

Jack Krawczyk is a Senior Director of Product at Google, building Bard. Bard is Google’s collaborative, conversational, and experimental AI tool that’s bridging the gap between humans and bots, while addressing ethical considerations around AI. After joining the project in 2020, Jack helped ship Bard in less than four years. Bard sources information directly from the web, and now enables users to inquire about and summarize YouTube videos. — In today’s episode, we discuss: Key lessons from Bard’s development process Ethics in AI How Bard shipped fast What separates Bard from competitors The future of LLM, Generative AI, and AGI Advice for aspiring AI developers — Referenced: Bard: https://bard.google.com/ ChatGPT: https://chat.openai.com/ Duet AI: https://cloud.google.com/duet-ai Free courses on machine learning by Andrew Ng: https://www.andrewng.org/courses/ Google Assistant: https://assistant.google.com/ Introducing Google Assistant to Bard: https://blog.google/products/assistant/google-assistant-bard-generative-ai/ Large Language Model (LLM): https://en.wikipedia.org/wiki/Large_language_model Meena: https://blog.research.google/2020/01/towards-conversational-agent-that-can.html Sissie Hsiao (GM at Bard): https://www.linkedin.com/in/sissie-hsiao-b24243/ Steve Stoute: https://www.linkedin.com/in/stevestoute/ UnitedMasters: https://unitedmasters.com/ — Where to find Jack Krawczyk: Twitter/X: https://twitter.com/JackK LinkedIn: https://www.linkedin.com/in/jack--k — Where to find Brett Berson: Twitter/X: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:17) Bard’s origin story (03:54) Deciding on the application of Bard (05:59) The ethical considerations around building Bard (10:19) Why Bard launched to the public so early (13:30) Risk-taking at big companies versus smaller ones (16:20) Bard’s early user research (21:21) Bard versus ChatGPT (25:01) The cultural and product principles behind Bard (30:56) Insight into Bard’s impressive development speed (35:17) Deciding when to ship Bard (41:41) Why Bard is different from other products Jack has built (46:30) Evaluating Bard’s original spec (48:02) Insight into Bard's product roadmap (56:00) The toughest challenges Bard has faced (57:50) What’s special about team-building at Bard (62:54) Addressing Bard’s negative press (67:49) Advice for aspiring LLM companies (69:15) Advice for non-LLM companies (71:05) The biggest barriers to advancing AI (75:45) How product people can use or build with AI (77:24) How AI is changing product leadership (79:20) People who had an outsized impact on Jack

Will Larson is the CTO at Carta, an ownership and equity management platform that raised at a $7.4b valuation in 2021. Prior to joining Carta, Will was CTO at Calm, founded Stripe's Foundation Engineering org, and led Uber’s Platform Engineering people and strategy. Will also writes extensively about engineering leadership, and has authored two books in this area: Staff Engineer, and An Elegant Puzzle. — In today’s episode we discuss: How to form an engineering strategy Common engineering management mistakes, and how to avoid them Advice for explaining, measuring, and optimizing engineering velocity Will’s nuanced approach to organizational policies Why it’s sometimes counterproductive to tell someone not to micromanage — Referenced: Accelerate (book): https://www.amazon.com/Accelerate-Software-Performing-Technology-Organizations/dp/1942788339 Calm: https://www.calm.com/ Carta: https://www.carta.com/ DORA: https://dora.dev/ Good Strategy, Bad Strategy (book): https://www.amazon.com/Good-Strategy-Bad-Difference-Matters/dp/0307886239 JavaScript: https://www.javascript.com/ KAFKA: https://kafka.apache.org/ Minto Pyramid (framework): https://untools.co/minto-pyramid Ruby on Rails: https://rubyonrails.org/ SPACE (framework): https://queue.acm.org/detail.cfm Stripe: https://www.stripe.com/ — Where to find Brett Berson: Twitter/X: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ — Where to find Will Larson: Twitter/X: https://twitter.com/lethain LinkedIn: https://www.linkedin.com/in/will-larson-a44b543/ Personal website/blog: https://lethain.com/ An Elegant Puzzle (book): https://www.amazon.com/Elegant-Puzzle-Systems-Engineering-Management/dp/1732265186 Staff Engineer (book): https://staffeng.com/book — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (03:03) The nuances of taking lessons from old companies (14:28) The value of writing down engineering principles (17:03) How to structure a strategy document (18:48) The 2 parts of any engineering strategy (21:08) Advice for turning strategy into action (23:44) Carta's unique "navigator" model (24:50) The Hidden Variable Problem (29:59) Explaining, measuring, and optimizing velocity (35:28) Useful metrics for engineering orgs (39:08) The balance between micromanagement and understanding details (43:03) Management anti-patterns (45:49) How to execute policies whilst managing their exceptions (47:56) What an excellent engineering executive looks like (53:53) How Will has evolved as an engineering executive (56:56) How to communicate with executives (63:18) Things that derail meetings (66:10) How to approach presentation feedback (67:30) A bad sign when working with direct reports (69:13) Advice for growing as an early-career engineer (71:11) Will's model for developing engineering teams (74:33) Sources of inspiration for Will's views on engineering management

Anastasis Germanidis is the Co-Founder & CTO at Runway, an applied AI research company shaping the next era of art, entertainment, and human creativity. Runway has raised $237m and was one of Time Magazine’s “100 most influential companies” in 2023. Runway has been a persistent viral sensation in recent years, and is behind many of the most famous AI demos online. — In today’s episode we discuss: The origins of Runway The limitations of being “customer-driven” when building in AI How Runway balances research development with product development How goal-setting and planning is different for AI products Advice for early-stage AI founders — Referenced: Containerization: https://aws.amazon.com/what-is/containerization/ Docker: https://www.docker.com/ Green screen tool by Runway: https://runwayml.com/green-screen/ Hugging Face: https://huggingface.co/ Hugging Face Spaces: https://huggingface.co/spaces Hugging Face Model Hub: https://huggingface.co/docs/hub/models-the-hub Replicate: https://replicate.com/ Runway Gen-1: https://research.runwayml.com/gen1 Runway Gen-2: https://research.runwayml.com/gen2 Runway’s 30 AI Magic Tools: https://runwayml.com/ai-magic-tools/ — Where to find Anastasis Germanidis: Twitter/X: https://twitter.com/agermanidis LinkedIn: https://www.linkedin.com/in/agermanidis Personal website: https://agermanidis.com/ Personal blog: https://blog.agermanidis.com/ — Where to find Todd Jackson: Twitter/X: https://twitter.com/tjack LinkedIn: https://www.linkedin.com/in/toddj0 — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (03:23) The unique story of how Runway's co-founders met (08:27) The origins of Runway (09:28) Forming the initial product (13:55) Turning Runway into a company (14:41)Approach to initial market segments (18:53) Early-adopters (21:20) The limitations of being “customer-driven” (25:54) Forming a vocal community (27:08) Fostering community (29:05) The progression of Runway's tech and use-cases (33:08) How they picked users for early release (34:00) Expanding past the first 100 users of Gen-2 (35:33) Runway’s approach to safety and content moderation (36:44) Balancing product development and research development (43:51) Runway's org structure (45:08) Goal-setting amidst constant change in AI (46:50) Why Runway doesn't plan very far ahead (50:26) Advice to early-stage AI founders (53:11) Will AI replace video editors? (55:04) When Runway had the most momentum (56:49) Anastasis' #1 piece of advice

Guillermo Rauch is the CEO of Vercel, a frontend-as-a-service product that was valued at $2.5b in 2021. Vercel serves customers like Uber, Notion and Zapier, and their React framework - Next.js - is used by over 500,000 developers and designers worldwide. Guillermo started his first company at age 11 in Buenos Aires and moved to San Francisco at age 18. In 2013, he sold his company Cloudup to Automattic (the company behind WordPress), and in 2015 he founded Vercel. — In today’s episode we discuss: Guillermo’s fascinating path into tech Learnings from building Cloudup and selling the company to Automattic (the company behind WordPress) Vercel’s origin story and path to product market fit How to make an open source business successful Vercel’s unique philosophy on developer experience Insights and predictions on the future of AI — Referenced: Algolia: https://www.algolia.com/ Apache Zookeeper: https://zookeeper.apache.org/ Apache Kafka: https://kafka.apache.org/ AWS: https://www.aws.training/ C++: https://www.techtarget.com/searchdatamanagement/definition/C Clerk: https://clerk-tech.com/ Cloudup: https://cloudup.com/ Commerce Cloud: https://www.salesforce.com/products/commerce/ Contentful: https://www.contentful.com/ Debian: https://www.debian.org/ Fintool: https://www.fintool.com/ Figma: https://www.figma.com/ GitLab: https://about.gitlab.com/ IRC: https://en.wikipedia.org/wiki/Internet_Relay_Chat KDE: https://kde.org/ Linux: https://en.wikipedia.org/wiki/Linux Mozilla: https://www.mozilla.org MooTools (UI library): https://mootools.net/ Next.js: https://nextjs.org/ React Native: https://reactnative.dev/ Red Hat: https://www.redhat.com/ Redpanda: https://redpanda.com/ Resend: https://resend.com/ Rust: https://www.rust-lang.org/ Salesforce: https://www.salesforce.com Servo: https://servo.org/ Shopify: https://www.shopify.com/ Socket.io: https://socket.io/ Symphony: https://symphony.com/ Trilio: https://trilio.io/ Twilio: https://www.twilio.com Vercel: https://vercel.com/ V0.dev: https://v0.dev/ — Where to find Guillermo: Twitter/x: https://twitter.com/rauchg LinkedIn: https://www.linkedin.com/in/rauchg/ Personal website: https://rauchg.com/ — Where to find Todd Jackson: Twitter: https://twitter.com/tjack LinkedIn: https://www.linkedin.com/in/toddj0 — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (02:35) Becoming an “internet celebrity” at age 11 (08:30) Guillermo's first company: Cloudup (11:09) Biggest learnings from Cloudup and WordPress (15:06) The insights behind starting Vercel (17:11) Sources of validation for Vercel (20:29) How Vercel formed its V1 product (23:25) Navigating the early reactions from competitors and users (25:58) The paradox of developers and how it impacted Next.js (31:20) Advice on finding product market fit (34:48) The forces behind a trend towards "Front-end Cloud” (38:35) Why people now pay so much attention to the front-end (40:06) How to make an open source business successful (44:54) Insights on product positioning and category creation (48:52) Vercel's journey through becoming multi-product (51:44) Guillermo's take on the future of AI (53:43) Heuristics for building better product experiences (55:49) AI insights from Vercel’s customers (57:37) How AI might change engineering in the next 10-20 years (62:43) Guillermo's favorite advice (65:45) Guillermo's advice to himself of 10 years ago

Ashley Kramer is the CMO and CSO at GitLab, a publicly listed DevSecOps platform. Ashley took a unique path into her CMO role. She started out in software engineering before becoming a product leader, and eventually, a marketer. Most recently, Ashley was the CPO and CMO at Sisense, a data analytics company last valued at over $1b. — In today’s episode we discuss: How GitLab layered a commercial model on top of open source roots GitLab’s main marketing metrics Examples, benefits, and downsides of a transparent company culture How GitLab serves enterprise customers, and a passionate developer community Unique marketing lessons from working in an open core company An example of a recent marketing campaign — Where to find Brett Berson: Twitter: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ — Where to find Ashley Kramer: Twitter/x: https://twitter.com/ashleyekramer LinkedIn: https://www.linkedin.com/in/ashleyekramer/ — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Referenced: CISO: https://www.cisco.com/c/en/us/products/security/what-is-ciso.html DevSecOps: https://about.gitlab.com/topics/devsecops/ E-Group: https://about.gitlab.com/company/team/e-group/ GitLab: https://gitlab.com GitLab legal team’s SAFE framework: https://about.gitlab.com/handbook/legal/safe-framework/ GitLab’s open core business model: https://handbook.gitlab.com/handbook/company/stewardship/ GitLab’s open source employee handbook: https://handbook.gitlab.com/handbook/people-group/ GitLab’s open source marketing handbook: https://about.gitlab.com/handbook/marketing/ GitLab’s open source remote handbook: https://handbook.gitlab.com/handbook/company/culture/all-remote/guide/ Sid Sijbrandij, CEO of GitLab: https://www.linkedin.com/in/sijbrandij/ Tableau: https://www.tableau.com/ — Timestamps: (00:00) Intro (02:34) Marketing in closed vs open source companies (07:40) The role of marketing at GitLab (09:23) The tensions of being a commercial, open source company (12:36) Advice for nurturing community and dealing with disagreements (15:02) GitLab's main marketing metrics (20:26) The thinking behind GitLab’s org structure, in and around marketing (28:19) Selling to enterprise as an open core company (29:53) The difference between open core and open source (30:39) Serving many different customer segments (35:10) GitLab's planning process (39:22) An example of GitLab’s marketing in practice (42:12) How marketing collaborates with product (45:55) Marketing lessons from working in an open core company (49:46) Examples of GitLab's focus on transparency (52:22) Why GitLab is transparent about their marketing (54:59) 2 examples of GitLab's uniquely transparent culture (58:35) The downsides of being a transparent company (60:13) GitLab's meeting structure and cadence (62:04) Benefits of having an engineering and product background as CMO (71:09) People who made an outsized impact on Ashley's career