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  • 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

  • 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

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  • 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) Transitioning from MVP to platform

    (24:18) Turning down a $5K deal on principle

    (26:47) Generalizing bespoke solutions

    (28:28) Finding product-market fit

    (33:51) Founder-led sales and consultative approach

    (39:30) Building a culture of reactivity

    (45:47) Landing the first enterprise customers

    (51:34) Silicon Valley’s obsession with frameworks

    (58:17) Developing first principles thinking

    (1:00:24) Stay competitor-informed

  • 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) How customer signal led to PDF processing

    (14:46) Landing a Fortune 10 customer

    (22:42) Building “transferable features”

    (25:58) How caring beats sales skills in startup growth

    (30:28) The strategy behind Reducto's horizontal expansion

    (36:18) Hire slow, go-to-market fast

    (41:45) A technical founder's guide to sales

    (43:45) “You’re going to fail”

    (46:27) Why startups win

    (48:30) Key insights from Reducto's fundraising journey

    (51:43) Less structure, more impact

    (55:00) How frustrations shaped Reducto’s culture

    (57:35) The question you should always ask in meetings

  • 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/@FirstRoundCapital

    This podcast on all platforms: https://review.firstround.com/podcast


    ---

    Timestamps:
    0:03 – How Jeff got involved with 1Password
    2:01 – How 1Password was initially set up
    10:41 – The secret CEO
    13:44 – What Jeff’s first six months encompassed
    16:13 – The lightbulb moment that caused a pivot
    17:50 – 1Password’s unusual company journey
    22:08 – Creating an aligned product roadmap
    29:19 – Retaining a customer-centric focus at scale
    30:40 – Why 1Password’s first B2B product failed
    39:43 – How Jeff thinks about competitors
    46:44 – Building different go-to-market functions
    52:45 – Staying bootstrapped for 15 years
    57:17 – Jeff’s one regret
    1:02:00 – 1Password’s most pivotal moments

  • 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://www.youtube.com/@FirstRoundCapital


    This podcast on all platforms: https://review.firstround.com/podcast


    --
    Timestamps:
    (00:00) Intro
    (01:29) Adam’s first business
    (04:15) The transition from Minecraft to Owner
    (05:58) The dark side of the gaming industry
    (14:20 Adam’s scrappy strategy to landing his first customers
    (16:52) The COVID pivot
    (21:31) The quest to find product-market fit
    (30:53) What actually worked to get new customers
    (36:03) Inside Owner’s explosive growth
    (46:41) How Owner secured its crucial first round of funding
    (53:34) The bet on going multi-product
    (64:28) What Adam wishes he knew at 17
    (76:22) Sales-led vs. product-led growth

  • 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 should know about outside hires
    (33:12) Eeke’s advice for easing leadership transitions
    (42:06) How to notice success patterns
    (47:21) Why high-functioning executive teams are like parents
    (52:02) The most surprising lesson from Eeke’s first stint at Stripe
    (55:11) The leadership data Eeke wishes we had

  • 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.com/podcast



    Timestamps:
    (00:00) Teaser: “I don’t believe in stealth mode”
    (02:51) Inspiration behind Guideline
    (07:56) Lessons from a year’s research before Guideline
    (10:44) Identifying market pull for Guideline
    (14:28) What Kevin learnt before shipping their first product
    (19:10) How Guideline set their fees up
    (27:51) The surprising range of Guideline’s early customers
    (31:48) Kevin’s insights from the Gusto integration
    (39:48) Guideline’s first year
    (44:44) Working with Plaid as Guideline’s first customer
    (53:28) Guideline’s auto-enrollment feature
    (57:53) Lucky 8: Kevin’s unexpected pricing strategy
    (62:04) Franchise opportunities
    (64:49) Kevin’s reflections on Taskrabbit
    (71:36) Will Guideline ever go multi-product?
    (72:37) Kevin’s take on product-market fit
    (73:30) Guideline’s compounding advantage
    (78:51) The challenges faced by introverted leaders

  • 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



    Timestamps:
    (00:00) Teaser: Finding “terminal value” product market fit
    (00:24) Introduction
    (02:34) Bill's insights into the mobile revolution
    (04:43) Lessons from Bridgewater Associates
    (09:12) First principles thinking in action at Braze
    (14:14) Meeting co-founders at an NYC Hackathon
    (24:35) Braze’s scrappy scaling
    (33:37) Early product development
    (39:37) From 1,000 beta signups to 2,200+ paying customers
    (43:51) Braze’s fundraising struggles
    (47:01) Breaking the rules of a lean startup
    (53:02) Riding the mobile wave to success
    (60:02) Building a global customer base
    (64:04) The never-ending quest for PMF
    (70:29) 3 things every founder needs to know
    (73:56) Navigating competition like a boxer
    (79:03) When scale helps or hurts
    (80:32) 1 thing they’ve learned from each other

  • 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/firstround


    YouTube: https://www.youtube.com/@FirstRoundCapital


    This podcast on all platforms: https://review.firstround.com/podcast



    Timestamps:
    (00:00) Teaser + Introduction
    (03:13) Turning traditional GTM on its head
    (05:37) How Clay hustled for its first customers: Reddit threads & WhatsApp groups
    (08:53) Unpacking Clay's credit-based pricing
    (14:29) Building Clay's self-serve engine
    (16:54) Why Clay rejected the usage-based model
    (19:04) Clay’s big bet on content
    (23:59) How "reverse demos" win enterprise deals
    (27:49) 3 changes that unlocked Clay's upmarket motion
    (36:59) How to build trust with enterprise buyers
    (38:49) Applying the land and expand model
    (40:40) Hiring people who are “technical enough”
    (46:33) Inside Clay’s hands-on interviewing process
    (48:15) Why Clay invested in brand from day-one
    (50:21) Clay’s contrarian take on compensation
    (58:35) The person who shaped Varun’s career

  • 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 principle behind dbt Labs’ rapid growth
    (11:20) Finding dbt Labs’ first customers
    (15:52) Consulting's hidden scalability
    (17:25) How dbt Labs created a new category
    (21:03) The anti-demo strategy
    (23:59) Community hacking: the Slack group that changed everything
    (26:00) The open source philosophy
    (27:39) When growth went exponential
    (28:49) How consulting engagements shaped the roadmap
    (30:02) Fundraising only when “things started to break”
    (32:40) Consultancy superpowers: the hidden advantages
    (34:04) Pivoting from consulting to software
    (40:00) Key monetization strategies
    (48:56) Why “begrudging” CEOs can be successful
    (51:02) Advice for finding PMF: “It’s not a playbook”
    (51:59) Lowering your standards is a hack
    (53:30) Navigating emotional overwhelm
    (54:25) Every CEO needs a coach

  • 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 simplicity matters
    (63:52) The importance of taste in product and design
    (67:56) The biggest influence on Yuhki’s product thinking

  • 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: https://steveblank.com/2011/05/10/the-lean-launchpad-at-stanford-–-the-final-presentations/


    The Secret History of Silicon Valley: https://steveblank.com/secret-history/



    Where to find Steve:

    LinkedIn: https://www.linkedin.com/in/steveblank/


    Twitter/X: https://twitter.com/sgblank


    Website: https://steveblank.com/



    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



    Timestamps:
    (00:00) Introduction
    (02:27) Validating ideas for defense products
    (03:57) Guide to military sales and procurement
    (07:15) Rethinking GTM strategies
    (10:13) Building a network in national security
    (15:07) The dual-use debate
    (18:35) Behind the rising number of “defense founders”
    (22:30) “Mission solution fit”
    (24:35) Breaking new ground in military tech
    (26:09) Essential resources for any defense founder
    (28:59) What’s missing from Silicon Valley

  • 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) How 17 diverse roles shaped Anneka’s CPO approach
    (40:54) The hidden career growth hack
    (43:15) Where domain experience is overrated
    (50:33) Mastering the art of altitude shifting
    (53:54) PMs should undergo the same training as sales reps
    (59:37) Strategies for selling to new personas
    (62:40) Lessons from Anneka’s mistake at LiveRamp
    (67:56) Who had an outsized impact on Anneka

  • Matt Lerner is the Founder and CEO at SYSTM, a startup coaching consultancy that helps high-potential companies grow their business. Matt also authored the book “Growth Levers”, which shares his framework that's helped over 200 seed-stage startups grow as much as 100x. Previously, Matt was on the early growth team at PayPal, a partner at 500 Startups, and a guest lecturer at Stanford Business School.
    -
    In today’s episode, we discuss:

    Understanding the key drivers of startup success

    Applying the Growth Lever framework

    Several case studies

    Customer-centric growth tactics

    Adapting growth levers for different business models

    -
    Referenced:

    Airbnb: https://www.airbnb.com/


    Bold Commerce: https://boldcommerce.com/


    Calm: https://www.calm.com/


    Caribou: https://www.usecaribou.com/


    eBay: https://www.ebay.com/


    FATMAP: https://fatmap.com/


    Growth Levers and How to Find Them: https://www.systm.co/growth-levers-matt-lerner-book


    PayPal: https://www.paypal.com/


    Peter Karpas: https://www.linkedin.com/in/peterkarpas/


    Popsa: https://popsa.com/


    Shopify: https://www.shopify.com/


    Sonic Jobs: https://www.sonicjobs.com/


    SYSTM: https://www.systm.co/


    -
    Where to find Matt Lerner:

    LinkedIn: https://www.linkedin.com/in/matthewlerner/


    Twitter/X: https://x.com/matthlerner


    -
    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) Intro
    (03:11) The hidden truth about startup success
    (05:10) Popsa's journey: A case study in growth
    (07:31) Breaking down the growth lever framework
    (11:30) Understanding the customer's journey
    (14:14) The art of customer interviews
    (18:07) Unlocking growth through customer insights
    (24:23) The triple threat: Founder failure modes
    (27:32) The power of founder-led growth strategies
    (32:42) Unlocking growth bottlenecks
    (36:40) Timing and implementation of growth strategies
    (39:43) Founder red flags
    (41:32) Crafting effective growth experiments
    (43:14) Why customer mindset is the ultimate growth driver
    (46:19) The power law of business
    (48:59) Why startups don’t need paid marketing
    (50:47) Growth levers for sales-driven companies
    (53:43) Matt's own application of growth principles
    (55:39) Growth levers in B2B sales
    (57:05) Finding customer "locksmith moments"
    (64:08) The mentor who shaped Matt's thinking

  • Bob Moore is the co-founder and CEO at Crossbeam, a “LinkedIn for data” platform that helps companies find overlapping opportunities with their partners. Crossbeam has raised US$117M to date and recently acquired Reveal in 2024. Bob previously cofounded RJMetrics (now part of Adobe Commerce Cloud) and Stitch Data (acquired by Talend). He is also the author of Ecosystem-Led Growth.
    In today’s episode, we discuss:

    The unique way he evaluated and validated startup ideas

    Lessons learned from falling in and out of product-market fit

    How to recognize and act on market shifts that impact your business

    Specific tactics for distribution and building with conviction vs. consensus

    Creating scalable and durable startups

    Unlocking network effects in software

    Getting mergers right


    Referenced:

    Adobe’s acquisition of Magento: https://techcrunch.com/2018/05/21/adobe-to-acquire-magento-for-1-6-b/


    Amazon Redshift: https://aws.amazon.com/redshift/


    Chris Merrick: https://www.linkedin.com/in/merrickchristopher/


    Crossbeam: https://www.crossbeam.com/


    Crossbeam/Reveal merger: https://www.crossbeam.com/crossbeam-and-reveal-merger-announcement/


    Ecosystem-Led Growth: https://www.robertjmoore.com/book


    Jake Stein: https://www.linkedin.com/in/jakestein/


    Nick Mehta: https://www.linkedin.com/in/nickmehta/


    Reveal: https://reveal.co/


    Rick Nucci: https://www.linkedin.com/in/ricknucci/


    RJMetrics: https://en.wikipedia.org/wiki/RJMetrics


    Simon Bouchez: https://www.linkedin.com/in/simonbouchez/


    Stitch Data: https://www.stitchdata.com/


    Talend’s acquisition of Stitch Data: https://www.businessinsider.com/talend-acquires-stitch-2018-11


    The 4 Levels of PMF: https://pmf.firstround.com/levels



    Where to find Bob Moore:

    LinkedIn: https://www.linkedin.com/in/robertjmoore/


    Twitter/X: https://x.com/robertjmoore



    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) Intro
    (02:44) Tactics for finding founder-market fit
    (06:17) Speaking to founders about startup ideas
    (11:16) Why founders loved Crossbeam
    (19:34) How RJMetrics found market fit then lost it
    (29:46) Lessons from RJMetrics’ exit
    (38:06) The importance of intellectual honesty
    (39:33) Building with conviction versus consensus
    (42:41) Lessons from a three-time founder
    (50:26) Building and distributing Crossbeam
    (57:58) The “joint jam” sales tactic
    (60:35) Unlocking network effects in a software business
    (63:27) Why Crossbeam merged with its competitor
    (72:51) Who had an outsized impact on Bob

  • Eoghan McCabe is the CEO and cofounder at Intercom, an AI customer service platform. Intercom has raised over $240M, and was last valued at $1.3B in 2018. After spending 9 years building the company, Eoghan left Intercom in 2020, but he’s since returned, reshaping Intercom and pioneering its pivot to an AI-first service. This episode highlights his unabashed takes on leaning into your intuition as a founder, and his perspectives on the critical junctures in company building.

    In today’s episode, we also discuss:

    Eoghan's reflections since leaving Intercom

    The value of intuition and first-principles thinking

    The changes Eoghan made upon returning to Intercom

    How Eoghan increased Intercom's productivity by 41%

    Tactical advice on hiring top talent

    Why you can't make small improvements in big categories

    Crafting a culture of ruthless honesty and transparency

    Why software branding is in crisis


    Referenced:

    37signals: https://37signals.com


    Basecamp: https://basecamp.com


    Brian Halligan (HubSpot): https://www.linkedin.com/in/brianhalligan


    David Heinemeier Hansson (37signals, Basecamp): https://www.linkedin.com/in/david-heinemeier-hansson-374b18221


    Intercom: https://www.intercom.com


    Jason Fried (37signals, Basecamp): https://www.linkedin.com/in/jason-fried


    Salesforce: https://www.salesforce.com


    Marc Benioff (Salesforce): https://www.linkedin.com/in/marcbenioff


    Zendesk: https://www.zendesk.com



    Where to find Eoghan:

    LinkedIn: https://www.linkedin.com/in/eoghanmccabe/


    Twitter/X: https://x.com/eoghan



    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
    0:00:00 - Founder intuition vs. standard practice
    0:25:00 - Silicon Valley knowledge loops
    0:28:13 - Building an executive team
    0:36:38 - Eoghan’s return to Intercom
    0:42:02 - Transparent and honest leadership
    0:46:42 - Changing Intercom’s strategy
    0:54:22 - AI and category disruption
    1:03:17 - How Intercom thinks about brand
    1:10:40 - Eoghan’s inspirations

  • Krithika Muthukumar is a marketing veteran. She is currently the VP of Marketing at OpenAI where she was the first marketing hire. Before that, she was Head of Marketing at Retool. Her longest tenure was at Stripe where she was hired as the first marketer and scaled with the company over nine years, from a 60-person team to 7500+. She began her career in Product Marketing at Google and Dropbox.

    In today’s episode, we discuss:

    Marketing lessons from OpenAI, Stripe, and Retool

    The 3 pillars of Stripe’s approach to brand

    How to manage resource allocation as a marketer

    Adapting marketing strategy to different business models

    Advice for early marketing hires


    Referenced:

    Coca-Cola AI-generated wish card campaign: https://theprint.in/ani-press-releases/coca-cola-ignites-diwali-celebrations-with-unique-personalized-ai-generated-wish-cards/1840093/


    Cristina Cordova: https://www.linkedin.com/in/cristinajcordova/


    Gong: https://www.gong.io/


    Greg Brockman: https://www.linkedin.com/in/thegdb/


    Kenzo Fong: https://www.linkedin.com/in/kenzofong/


    Retool: https://retool.com/


    Stripe’s “Capture the Flag” campaign: https://techcrunch.com/2012/08/22/stripes-capture-the-flag-2-0-a-hands-on-contest-for-app-developers-to-test-their-security-know-how/


    Stripe Press: https://press.stripe.com/


    Stripe Sigma: https://stripe.com/us/sigma


    Tanya Khakbaz: https://www.linkedin.com/in/tanya-khakbaz-a725732/



    Where to find Krithika Muthukumar:

    LinkedIn: https://www.linkedin.com/in/krithix/


    Twitter/X: https://x.com/krithix



    Where to find Brett Berson:

    LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/


    Twitter/X: https://twitter.com/brettberson



    Timestamps:
    (00:00) Intro
    (02:43) Getting involved in Stripe
    (05:37) Evaluating success in product marketing
    (06:35) The 3 pillars of Stripe's approach to brand
    (12:10) Managing resource allocation as Stripe grew
    (17:22) How Stripe scaled taste
    (21:30) Were Stripe reviews micromanaging?
    (24:16) Marketing under founders with strong marketing skills
    (26:44) Advice for early marketing hires
    (31:52) Marketing at Retool vs Stripe
    (33:59) Marketing to mid-market vs SMB vs enterprise
    (37:02) Marketing programs that had an outsized impact
    (39:59) Marketing horizontal vs vertical products
    (43:20) Lessons from OpenAI
    (52:22) Inside OpenAI’s recent website relaunch
    (55:57) How OpenAI’s marketers use OpenAI tooling
    (59:53) When to start hiring marketers
    (61:34) How to screen early marketing hires
    (66:39) The biggest influences on Krithika's career
    (67:52) Outro

  • Sam Schillace is the CVP and Deputy CTO at Microsoft. Before Microsoft, Sam held prominent engineering roles at Google and Box. He has also founded six startups, including Writely, which was acquired by Google and became Google Docs.

    In today’s episode, we discuss:

    Sam’s advice for future engineers

    What’s next for AI

    How to develop technical taste

    The importance of asking “what if” questions

    Lessons on market timing

    Scaling a software company in 2024


    Referenced:

    Amazon: https://amazon.com


    Box: https://www.box.com/


    Elon Musk: https://twitter.com/elonmusk


    Google Docs: https://docs.google.com


    Itzhak Perlman: https://itzhakperlman.com/


    Microsoft: https://www.microsoft.com


    Netflix: https://www.netflix.com


    Tesla: https://www.tesla.com/


    The Innovator’s Dilemma: https://www.amazon.com.au/Innovators-Dilemma-Clayton-M-Christensen/dp/0062060244


    TurboTax: https://turbotax.intuit.com/


    Uber: https://www.uber.com/


    Walmart: https://www.walmart.com/


    Workday: https://www.workday.com/


    Writely: https://techcrunch.com/2005/08/31/writely-process-words-with-your-browser/



    Where to find Sam Schillace:

    LinkedIn: https://www.linkedin.com/in/schillace/


    Newsletter: https://sundaylettersfromsam.substack.com/


    Twitter/X: https://twitter.com/sschillace



    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
    (02:54) Lessons on market timing
    (07:30) Developing technical taste
    (09:51) Asking “what if” questions
    (14:03) Building Google Docs
    (19:32) The decline of Google apps
    (20:57) The Innovator’s Dilemma facing Microsoft
    (22:53) The differences between Google and Microsoft
    (24:42) How to build a winning product
    (27:46) Becoming an optimist
    (29:12) Why engineering teams aren’t smaller
    (32:00) Sam’s prediction about AI
    (34:11) Capturing the value of AI
    (37:43) How you should think about AI
    (45:33) Advice for future engineers
    (48:18) What makes a great engineer
    (49:45) One thing the best engineers do
    (51:37) Microsoft’s new leverage
    (56:01) Scaling software in 2024
    (59:50) The future of AI across several sectors
    (64:28) What Sam and a violinist have in common

  • Casey Winters is a legendary advisor on scaling, product and growth. He’s worked with companies like Airbnb, Faire, Canva, Whatnot, Thumbtack, Tinder, and Reddit. Until recently, Casey was the Chief Product Officer at Eventbrite, and has also led growth and product teams at Pinterest and Grubhub.

    In today’s episode, we discuss:

    What every marketplace founder should think about

    Why marketplaces are different

    Finding product market fit

    Key ingredients to scaling a marketplace

    Strategies for acquiring demand and supply


    Referenced:

    Airbnb: https://airbnb.com/


    Bill Gurley: https://www.linkedin.com/in/billgurley/


    Blue Apron: https://www.blueapron.com/



    Booking.com: https://www.booking.com/


    DoorDash: https://www.doordash.com/


    eBay: https://ebay.com/


    Eventbrite: https://www.eventbrite.com/


    Expedia: https://www.expedia.com/


    Faire: https://www.faire.com/


    Fermat Commerce: https://www.fermatcommerce.com/


    Grubhub: https://www.grubhub.com/


    Lyft: https://www.lyft.com/


    Pinterest: https://www.pinterest.com/


    Postmates: https://postmates.com/


    Shopify: https://www.shopify.com/


    Simon Rothman: https://www.linkedin.com/in/simonrothman/


    Square: https://squareup.com/


    Tony Xu: https://www.linkedin.com/in/xutony/


    Turo: https://turo.com/


    Uber: https://www.uber.com/


    Zillow: https://www.zillow.com/



    Where to find Casey Winters

    LinkedIn: https://www.linkedin.com/in/caseywinters/


    Twitter/X: https://twitter.com/onecaseman


    Website: https://caseyaccidental.com/



    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
    (02:30) Ingredients for a successful marketplace
    (05:34) Creating scalable growth loops
    (08:42) Emerging marketplaces in 2024
    (10:56) 2 ways to acquire supply and demand
    (15:39) What’s unique about building a marketplace
    (18:27) When to focus on the demand side
    (23:10) Who to hire
    (26:22) Finding sticky customers
    (26:27) What Grubhub should’ve done
    (30:19) Uber versus Lyft
    (34:23) One thing all marketplace founders should know
    (34:45) Finding product market fit
    (40:45) Single versus multi-category marketplaces
    (43:02) When to expand
    (44:22) The best low-frequency marketplace
    (46:00) The product is supply, not software
    (50:48) No value in car-sharing
    (56:11) Improving supply and demand over time
    (61:04) The “setup, aha, and habit” framework
    (66:27) Avoid these marketplace mistakes
    (71:16) 2 people who influenced Casey’s thinking