In Depth

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:

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Where to find Bob Moore:

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Where to find Brett Berson:

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Where to find First Round Capital:

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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.

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In today’s episode, we also discuss:

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Referenced:

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Where to find Eoghan:

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Where to find Brett Berson:

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Where to find First Round Capital:

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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.

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In today’s episode, we discuss:

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Referenced:

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Where to find Krithika Muthukumar:

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Where to find Brett Berson:

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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.

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In today’s episode, we discuss:

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Where to find Sam Schillace:

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Where to find Brett Berson:

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Where to find First Round Capital:

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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

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:

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Where to find Casey Winters

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Where to find Brett Berson:

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Where to find First Round Capital:

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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

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:

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Where to find Milin Desai:

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Where to find Brett Berson:

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Where to find First Round Capital:

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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

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:

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Referenced:

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Where to find Matt MacInnis:

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Where to find Brett Berson:

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Where to find First Round Capital:

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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:

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Referenced:

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Where to find Alyssa Henry:

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Where to find Brett Berson:

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Where to find First Round Capital:

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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

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:

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Referenced:

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Where to find Adam Nash:

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Where to find Brett Berson:

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Where to find First Round Capital:

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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”

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:

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Referenced:

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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:

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Where to find First Round Capital:

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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