In Depth First Round
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- Business
Welcome to In Depth, a new podcast from First Round Review that’s dedicated to surfacing the tactical advice founders and startup leaders need to grow their teams, their companies and themselves. Hosted by Brett Berson, a partner at First Round, In Depth will cover a lot of ground and a wide range of topics, from hiring executives and becoming a better manager, to the importance of storytelling inside of your organization. But every interview will hit the level of tactical depth where the very best advice is found. We hope you’ll join us. Subscribe to “In Depth” now and learn more at firstround.com
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Developing technical taste: A guide for next-gen engineers | Sam Schillace (Deputy CTO at Microsoft, creator of Google Docs)
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.
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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
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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/
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Where to find Sam Schillace:
LinkedIn: https://www.linkedin.com/in/schillace/
Newsletter: https://sundaylettersfromsam.substack.com/
Twitter/X: https://twitter.com/sschillace
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Where to find Brett Berson:
LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/
Twitter/X: https://twitter.com/brettberson
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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
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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 -
How to build and scale winning marketplaces | Casey Winters (Eventbrite, Pinterest, Grubhub)
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.
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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
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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/
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Where to find Casey Winters
LinkedIn: https://www.linkedin.com/in/caseywinters/
Twitter/X: https://twitter.com/onecaseman
Website: https://caseyaccidental.com/
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Where to find Brett Berson:
LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/
Twitter/X: https://twitter.com/brettberson
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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
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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 -
Lessons from Sentry on scaling DevTools and finding product market fit (again) | Milin Desai (Sentry, VMware, Riverbed)
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.
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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
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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/
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Where to find Milin Desai:
LinkedIn: https://www.linkedin.com/in/milin-desai-464757/
Twitter/X: https://twitter.com/virtualmilin
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Where to find Brett Berson:
LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/
Twitter/X: https://twitter.com/brettberson
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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
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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 -
How to be effective up and down the org chart | Matt MacInnis (Rippling, Inkling, Apple)
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.
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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
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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
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Where to find Matt MacInnis:
LinkedIn: https://www.linkedin.com/in/macinnis/
Twitter/X: https://twitter.com/stanine
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Where to find Brett Berson:
LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/
Twitter/X: https://twitter.com/brettberson
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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
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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 -
Timeless lessons on running software companies that endure | Alyssa Henry (Square, Amazon, Microsoft)
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.
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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
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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
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Where to find Alyssa Henry:
LinkedIn: https://linkedin.com/in/alyssa-henry-0905692
Twitter/X: https://twitter.com/alyssahhenry
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Where to find Brett Berson:
LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/
Twitter/X: https://twitter.com/brettberson
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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
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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 -
Building products that delight customers | Adam Nash (Daffy, Wealthfront, LinkedIn, eBay, Apple)
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.
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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
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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/
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Where to find Adam Nash:
LinkedIn: https://www.linkedin.com/in/adamnash/
Twitter/X: https://twitter.com/adamnash
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Where to find Brett Berson:
LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/
Twitter/X: https://twitter.com/brettberson
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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
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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”