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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Referenced:

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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

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:

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Referenced:

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Where to find Dennis Pilarinos:

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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

(02:18) 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:

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Referenced:

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Where to find May Habib:

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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

(02:34) 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”

Amjad Masad is the co-founder and CEO of Replit, an online platform designed for collaborative coding in multiple programming languages. Replit boasts over 30m users, has secured $200M in venture funding, and was recently valued at $1.2B. Before Replit, Amjad was a Software Engineer at Facebook, and a Founding Engineer at Codecademy.

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In today’s episode, we discuss:

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Referenced:

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Where to find Amjad Masad:

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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

(02:31) Replit’s origin story

(08:24) Starting Facebook’s JavaScript infrastructure team

(10:36) Amjad’s unique path to entrepreneurship

(16:04) How Replit got its early users

(17:00) Replit’s fundraising difficulties

(17:54) Why YC almost rejected Replit four times

(20:23) Building Replit’s distribution engine

(22:08) Drivers of Replit’s growth

(27:41) What Silicon Valley gets wrong

(30:09) Replit’s monetization strategy

(32:29) Integrating AI into the platform

(36:18) The impact of AI on software engineering

(39:40) Defining the new “software creator” role

(41:43) How to keep up with developments in AI

(46:24) Replit’s goals for 2024

(48:11) Advice for founders: defy conventional wisdom

(51:12) Amjad’s 4 favorite books

Michael Cieri is the Chief Product Officer at Gusto, an HR and payroll platform used by more than 300,000 businesses. With a decade of experience, he has led successful SMB product development and scaled high-performing orgs. Before Gusto, Michael was also the Head of Product at Square, where he led a team of 15+ PMs responsible for $600m in annual revenue. Michael was also the VP of Product Management at Opendoor.

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In today’s episode, we discuss:

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Referenced:

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Where to find Michael Cieri:

• LinkedIn: https://www.linkedin.com/in/michaelcieri/

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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

(02:41) Why SMBs require unique software solutions

(05:58) The level of specificity required when building for SMBs

(08:47) Finding Square’s form-fitting solution

(11:48) Building vertical versus horizontal SaaS

(14:34) Inside Square and Gusto’s decision making framework

(16:15) How to build horizontally from a wedge product

(23:00) Using the Three Horizons Model

(25:29) How to craft a compelling vision for products

(28:51) How to assess Horizon 3 bets

(32:08) How to give employees the freedom to try things

(34:24) Creating a risk-taking culture

(37:27) Essential advice for new PMs

(40:27) Common thread with bad product pitches

(42:29) Applying the Horizon framework at Gusto

(44:46) Developing good product sense

(47:43) 5 signs of great product sense

(49:03) Why product sense is like athletic ability

(51:43) How to ship faster without increasing headcount

(56:10) People who had an outsized impact on Michael

Stephanie Berner is a Customer Success Executive at LinkedIn. Since 2018, Stephanie has spearheaded all post-sales functions at LinkedIn Sales Solutions through its period of rapid growth. With a background in building and scaling customer success teams at Box, Medallia, and Opower, Stephanie has extensive experience in delivering exceptional customer experiences across various company stages.

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In this episode, we discuss:

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Referenced:

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Where to find Stephanie Berner:

• LinkedIn: https://www.linkedin.com/in/stephanieberner/

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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

(02:21) Formalizing customer success at a startup

(05:01) Hiring ICs before CSMs

(06:22) Tactics for hiring standout talent

(11:39) 3 questions to ask candidates

(15:38) Fail-case patterns among customer success hires

(17:49) Considering candidates with non-traditional backgrounds

(21:21) Indexing toward a bias for action

(24:17) What v1 of customer success looks like

(26:03) Key early-stage customer success metrics

(28:21) Whether customer success or sales should own renewals

(30:40) Where customer success fits into the org

(32:14) Why customer success doesn’t report to an executive

(33:48) Distinguishing a product problem from a customer success one

(35:18) Simple way to deal with customer churn

(39:21) Tactics to get customers to give honest feedback

(40:58) What happens when customer success and product teams collaborate

(44:14) Rituals for zero-to-one customer success

(48:23) How to structure an early customer success team

(52:01) Structuring compensation packages

(54:35) Aligning customer success with the business model

(60:14) The role of customer success in B2B software

(62:17) Common customer success mistakes

(67:44) People who had an outsized impact on Stephanie