May Habib is the co-founder and CEO of Writer, a full-stack generative AI platform built for enterprises. The model is trained on a customer’s own data to create content that is consistent with their brand style and voice. Writer recently raised $100M at a valuation of around $500M. Prior to Writer, May co-founded Qordoba, an AI writing assistant.
— 
In today’s episode, we discuss:

Advice for AI founders in 2024

Why it’s difficult to scale AI products for enterprise

The secret to finding champions

Signs of a healthy co-founder relationship

The future of agentic AI

— 
Referenced:

Accenture: https://www.accenture.com


ChatGPT: https://chat.openai.com/


Dropbox: https://www.dropbox.com


Goldman Sachs: https://www.goldmansachs.com/


Grammarly: https://www.grammarly.com


Jill Kramer: https://www.linkedin.com/in/jill-kramer-64230840/


L’Oreal: https://www.loreal.com/


Northwestern Mutual: https://www.northwesternmutual.com/


Palmyra: https://writer.com/blog/palmyra/


Retrieved Augmented Generation: https://blogs.nvidia.com/blog/what-is-retrieval-augmented-generation/


United Healthcare: https://www.uhc.com/


Vanguard: https://global.vanguard.com/


Waseem Alshikh: https://www.linkedin.com/in/waseemalshikh/


Writer: https://writer.com/


— 
Where to find May Habib:

LinkedIn: https://www.linkedin.com/in/may-habib/


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


— 
Where to find Todd Jackson:

LinkedIn: https://www.linkedin.com/in/toddj0/


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


— 
Where to find First Round Capital:

Website: https://firstround.com/


First Round Review: https://review.firstround.com/


Twitter: https://twitter.com/firstround


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


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


— 
Timestamps:
(00:00) Introduction
(02:34) Writer’s origin story
(06:30) Building a full-stack generative AI platform for enterprise
(11:56) The #1 challenge building Writer
(15:41) Writer’s approach to finding champion customers
(20:29) How Writer is winning the enterprise space
(27:11) Signs Writer found product-market-fit
(29:26) Scaling LLMs for specific use cases
(31:53) Writer’s goals for 2024
(33:57) Advice for 0 to 1 founders
(35:53) Creating a culture of “connect, challenge, and own”

Scaling and selling AI products for enterprise | May Habib (Co-founder and CEO of Writer)

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

Business

Investing

Careers

Management & Marketing

Business News

Shopping

Management

Entrepreneurship

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

How to build and scale winning marketplaces | Casey Winters (Eventbrite, Pinterest, Grubhub)

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

Lessons from Sentry on scaling DevTools and finding product market fit (again) | Milin Desai (Sentry, VMware, Riverbed)

Matt MacInnis is the COO at Rippling, an all-in-one HR, IT, and finance platform for businesses, which last raised $500M at a $11.25B valuation. Before Rippling, Matt was the co-founder and CEO at Inkling, a mobile learning platform that was acquired in 2018. He also held several management roles at Apple.
—
In today’s episode, we discuss:

Lessons on culture, org-design, and product from Rippling

Characteristics of great CEOs

How to a better executive leader

Leading with kindness and impatience

How to fight entropy

—
Referenced:

Andy Roddick: https://www.atptour.com/en/players/andy-roddick/r485/overview


Apple: https://www.apple.com


Bain & Company: https://www.bain.com/


Bill Campbell: https://en.wikipedia.org/wiki/Bill_Campbell_(business_executive)


Conscious Business: https://www.amazon.com.au/Conscious-Business-Build-Value-Through/dp/1622032020


Google: https://www.google.com


Inkling: https://www.inkling.com/


McCaw Cellular: https://en.wikipedia.org/wiki/McCaw_Cellular_Communications


McKinsey: https://www.mckinsey.com/


Microsoft: https://www.microsoft.com


Oracle: https://www.oracle.com


Parker Conrad: https://www.linkedin.com/in/parkerconrad/


Peter Currie: https://en.wikipedia.org/wiki/Peter_Currie_(businessman)


Rippling: https://www.rippling.com


The Effective Executive: https://www.amazon.com.au/Effective-Executive-Peter-Ferdinand-Drucker/dp/0060833459


—
Where to find Matt MacInnis:

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


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


—
Where to find Brett Berson:

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


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


—
Where to find First Round Capital:

Website: https://firstround.com/


First Round Review: https://review.firstround.com/


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


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


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


—
Timestamps:
(00:00) Introduction
(02:14) Great CEOs don’t worry about their weaknesses
(06:31) The third-time founder mindset
(08:09) Why every great CEO is impatient
(11:54) How executives fight entropy
(19:11) Experience ≠ wisdom
(21:26) Managing workplace politics
(24:02) Why all businesses should dogfood
(26:20) Overseeing employee expenses
(27:43) The best CEOs don’t need coaching
(29:55) The hidden cost of advice
(40:40) Why execs are “tortured but happy”
(44:16) Clear versus first principles thinking
(51:09) Finding first principles thinkers
(53:13) Why people overcomplicate culture
(55:53) Don’t make this mistake when interviewing
(59:26) The importance of anti-patterns
(61:27) Important business values
(63:28) How Matt thinks about output
(66:33) Rippling’s key leadership principle
(71:02) Why kindness matters
(72:03) Freeing yourself from self-doubt

How to be effective up and down the org chart | Matt MacInnis (Rippling, Inkling, Apple)

Alyssa Henry is the former CEO of Square, a financial services company providing products and services used by over 4 million merchants. Formerly at Amazon, Alyssa led the development and growth of Simple Storage Service (S3) at AWS. Alyssa now serves as an Independent Director at Intel and Confluent.
— 
In today’s episode, we discuss:

Lessons from Amazon, Microsoft, and Square

“Minimum Remarkable Products” versus Minimum Viable Products

Navigating different work cultures in big tech

Insider reactions to the disruptive launch of AWS

“Pioneer” versus “fast-follower” companies

— 
Referenced:

Amazon: https://www.amazon.com


Amazon Web Services: https://aws.amazon.com


Bill Gates: https://www.linkedin.com/in/williamhgates


Block, Inc: https://block.xyz


Cash App: https://cash.app


Fast Company - Back To Square One: https://www.fastcompany.com/3033412/back-to-square-one


Gokul Rajaram: https://www.linkedin.com/in/gokulrajaram1


Jack Dorsey: https://twitter.com/Jack


James Hamilton: https://www.linkedin.com/in/jameshamilton4


Jeff Bezos: https://twitter.com/jeffbezos


Microsoft: https://www.microsoft.com


Oracle Corporation: https://www.oracle.com


Sarah Friar: https://www.linkedin.com/in/sarah-friar


Square: https://squareup.com


Tom Szkutak: https://www.linkedin.com/in/tom-szkutak-4b59817


WSJ - Mobile-Payments Startup Square Discusses Possible Sale: https://www.wsj.com/articles/SB10001424052702303825604579513882989476424


— 
Where to find Alyssa Henry:

LinkedIn: https://linkedin.com/in/alyssa-henry-0905692


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


— 
Where to find Brett Berson:

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


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


— 
Where to find First Round Capital:

Website: https://firstround.com/


First Round Review: https://review.firstround.com/


Twitter: https://twitter.com/firstround


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


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


— 
﻿Timestamps:
(00:00) Introduction
(02:20) Lessons from Microsoft and Amazon
(08:29) Noticeable consistencies in the human condition
(10:50) Differences in culture at Amazon, Microsoft and Square
(13:27) Why “customers come first,” even above employees and community
(14:01) Why fast-followers can be less customer-focused
(15:50) The challenge of commercializing research projects
(18:58) Joining Square and “building a picture” of the org
(24:55) Knowing what to replicate from past companies
(27:45) Questioning norms in new companies
(28:41) The importance of effective communication systems
(31:31) How to operationalize company values
(33:38) Why shared beliefs are crucial for good company culture
(37:05) Building Minimal Remarkable Products at Square
(38:13) How to scale an aesthetic
(42:46) Org design lessons from Square
(50:06) How to align different teams behind business priorities
(52:57) Lessons learned from fierce competition
(57:39) The “fast follower” vs “pioneer” playbook
(61:05) The original thinking behind AWS
(66:08) The unlikely origin of Amazon CloudFront and other products
(73:47) How Jeff Bezos influenced Alyssa

Timeless lessons on running software companies that endure | Alyssa Henry (Square, Amazon, Microsoft)

Adam Nash is the co-founder and CEO at Daffy, a platform that makes it easier to donate to charities and non-profits. Before Daffy, Adam was the President and CEO at Wealthfront, where he scaled the company’s assets under management from $100M to over $4B. Adam has also held leadership and technical roles at Dropbox, LinkedIn, eBay, and Apple.
—
In today’s episode, we discuss:

Why founders should build platforms, not apps

The importance of “delighting” customers

How Daffy is disrupting donor-advised-funds

Lessons on strategy from LinkedIn

How to think about leadership transitions

—
Referenced:

Andy Rachleff: https://www.linkedin.com/in/rachleff/


Bill Gates: https://www.linkedin.com/in/williamhgates/


Daffy: https://www.daffy.org/


Daffy’s 2023 Year in Review: https://www.daffy.org/resources/year-in-review-2023


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


Jeff Weiner: https://www.linkedin.com/in/jeffweiner08/


Reid Hoffman: https://www.linkedin.com/in/reidhoffman/


Robinhood: https://robinhood.com/


Ryan Roslansky: https://www.linkedin.com/in/ryanroslansky/


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


Tim Cook: https://www.apple.com/leadership/tim-cook/


Wealthfront: https://www.wealthfront.com/


—
Where to find Adam Nash:

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


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


—
Where to find Brett Berson:

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


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


—
Where to find First Round Capital:

Website: https://firstround.com/


First Round Review: https://review.firstround.com/


Twitter: https://twitter.com/firstround


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


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


—
Timestamps:
(00:00) Introduction
(02:08) Why the last 10 years have been less disruptive
(06:15) Why we think about luck wrong
(08:39) How eBay survived the dot com bubble
(14:37) The value of building platforms, not apps
(22:18) What made LinkedIn successful
(27:31) Good company strategy = good product strategy
(30:58) Setting LinkedIn’s strategy in 2009
(36:41) Why KaChing didn’t work
(40:56) Pivoting to Wealthfront
(43:23) Universal lesson on customer acquisition
(45:11) Treating growth like a product problem
(49:01) Advice on successful leadership transitions
(54:20) How to delegate moral authority
(60:24) The problem with metrics and customer requests
(66:41) Apple’s approach to “delighting” customers
(69:16) The 70/20/10 rule you’ve never heard about
(70:29) How Daffy ships “delight features”

Scaling and selling AI products for enterprise | May Habib (Co-founder and CEO of Writer)

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