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

Milin Desai is the CEO at Sentry, an application monitoring tool for developers. Sentry has recently passed two key milestones: 100K customers and over $100M in ARR. Before Sentry, Milin was a GM at VMware and scaled their cloud networking into a billion-dollar business. Prior to stepping into leadership roles, Milin was a PM at Riverbed and a software engineer at Veritas.

—

In today’s episode, we discuss:

• The key ingredients of Sentry’s success
• Sentry’s developer-centric approach
• Lessons on pricing, packaging, and product from VMware
• Being an external CEO at a startup
• Forging successful relationships with founders

—

Referenced:

• Building for the Fortune 500,000: https://blog.sentry.io/building-for-the-fortune-500-000/
• Carl Eschenbach: https://www.linkedin.com/in/carl-eschenbach-980543/
• Chris Jennings: https://www.linkedin.com/in/chriskjennings/
• David Cramer: https://www.linkedin.com/in/dmcramer/
• FRC’s product market fit framework: https://pmf.firstround.com/
• Martin Casado: https://www.linkedin.com/in/martincasado/
• Pat Gelsinger: https://www.linkedin.com/in/patgelsinger/
• Raghu Raghuram: https://www.linkedin.com/in/raghuraghuram/
• Riverbed: https://www.riverbed.com/
• Sentry: https://sentry.io/
• Todd Bazakas: https://www.linkedin.com/in/todd-bazakas-b5a2533/
• Veritas: https://www.veritas.com/
• VMware: https://www.vmware.com/

—

Where to find Milin Desai:

• LinkedIn: https://www.linkedin.com/in/milin-desai-464757/
• Twitter/X: https://twitter.com/virtualmilin

—

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

(03:03) Joining Sentry as an external CEO

(06:27) The CEO/founder relationship

(09:37) Lessons from VMware

(13:04) What PMs did differently at VMware

(18:04) Becoming the need, not the want

(20:53) Scaling Sentry

(23:07) Building for the “Fortune 500,000”

(27:02) Open versus closed source product

(30:43) The key ingredients to Sentry’s success

(36:21) How Milin updated his playbook at Sentry

(38:49) Focus on packaging, not pricing

(40:29) “Build for the many, not the few”

(41:53) Sentry’s B2D model

(45:10) The second product mindset

(51:03) Contrarian take on building for enterprise

(52:50) Several people who influenced Milin