In Depth First Round

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

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


— 
Where to find First Round Capital:

Website: https://firstround.com/


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


Twitter: https://twitter.com/firstround


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


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


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

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


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

Eilon Reshef is the co-founder and CPO at Gong, an AI-powered platform that tracks, records, and analyzes sales calls to drive revenue growth. In 2021, Gong raised $250M at a $7.25B valuation. Gong was one of the fastest SaaS companies to hit $100m ARR, and now has over 4000 customers. Before Gong, Eilon sold his previous e-commerce startup, Webcollage.
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In today’s episode, we discuss:

Why Eilon was so bullish on recording sales calls

How Gong knew they had product market fit

The importance of design partners

Expanding into multi-product offerings

Lessons from riding the AI wave since 2015

The future of AI in B2B sales efficiency

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Referenced:

Act-On Software: https://act-on.com/


Amit Bendov: https://www.linkedin.com/in/amitbendov/


BlueJeans: https://www.bluejeans.com/


Crossing the Chasm: https://www.amazon.com/Crossing-Chasm-3rd-Geoffrey-Moore/dp/0062292986


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


Mistral: https://mistral.ai/


OpenAI: https://openai.com/


Salesforce: https://salesforce.com/


Webcollage: https://www.crunchbase.com/organization/webcollage


Webex: https://www.webex.com/


Zoom: https://zoom.us/


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Where to find Eilon Reshef:
LinkedIn: https://www.linkedin.com/in/eilonreshef/

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Where to find Todd Jackson:

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


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


—
Where to find First Round Capital:

Website: https://firstround.com/


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


Twitter: https://twitter.com/firstround


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


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


—
Timestamps:
(00:00) Introduction
(02:32) Eilon’s unwavering conviction in Gong
(09:34) Initial reactions to Gong’s demo
(13:48) Keeping the beta lean
(15:33) Gong’s monetization strategy
(16:38) Early signs of product market fit
(18:14) The importance of design partners to Gong’s growth
(21:52) Why VCs were afraid to invest
(23:43) Reaching 100 customers
(26:10) Eilon’s unique product roadmap framework
(28:22) Going from $2M to $9M ARR in one year
(29:02) The journey to multi-product
(30:52) How Gong measures success
(34:07) Lessons from building AI products for sales
(37:45) Predicting the future of B2B sales
(38:48) The concept of “raving fans”
(39:31) Why it’s “easier” for second-time founders
(42:00) Eilon’s favorite books
(42:45) Gong in 2024

Dennis Pilarinos is the founder and CEO at Unblocked, a developer tool that lets you talk to your codebase. In 2018, Dennis’ first company, Buddybuild, was acquired by Apple, and he was subsequently appointed Director of Development Technologies. Before that, Dennis was a Senior Director at AWS and a Director at Microsoft.
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In today’s episode, we discuss:

Lessons on culture and product from Amazon, Apple, and Microsoft

Building and scaling DevTools

Finding product market fit and monetizing it

Why AI is complicating product market fit

How Dennis prioritizes mental health as a founder

The common mistake people make when hiring

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Referenced:

Apple’s acquisition of Buddybuild: https://www.cnbc.com/2018/01/02/apple-agrees-to-buy-buddybuild.html


AWS: https://aws.amazon.com


Bitbucket: https://bitbucket.org


Confluence: https://www.atlassian.com/software/confluence


GitHub: https://github.com


GitLab: https://gitlab.com


Looker: https://looker.com


Microsoft Azure: https://azure.microsoft.com


Stewart Butterfield: https://www.linkedin.com/in/butterfield/


Stripe: https://stripe.com


Twilio: https://twilio.com


Unblocked: https://getunblocked.com/


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Where to find Dennis Pilarinos:

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


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


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Where to find Brett Berson:

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


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


—
Where to find First Round Capital:

Website: https://firstround.com/


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


Twitter: https://twitter.com/firstround


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


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


—
Timestamps:
(00:00) Introduction
(02:18) Why building for developers is different
(07:28) Buddybuild’s origin story
(10:40) Early signs of product market fit
(12:22) Managing mental health as a second-time founder
(21:09) Building and scaling Unblocked
(29:52) Dennis’ cautious take on AI
(34:20) Being customer-obsessed
(35:25) Unblocked’s decision-making process
(38:31) Don’t over-index on competency when hiring
(43:36) Why great product is everything
(45:41) Monetizing product market fit
(48:21) The power of positioning
(51:48) Why Dennis doesn’t do demos
(54:45) How to deal with customer feedback
(57:29) Stewart Butterfield’s impact on Dennis

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

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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”