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

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

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”

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.

—

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

—

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/

—

Where to find Eilon Reshef:

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

—

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.

—

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

—

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/

—

Where to find Dennis Pilarinos:

• LinkedIn: https://www.linkedin.com/in/dennispi
• Twitter/X: https://twitter.com/dennispilarinos

—

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.

— 

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”

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.

—

In today’s episode, we discuss:

• How AI is reshaping the software landscape
• Bridging the gap between ideas and software
• Why YC almost rejected Replit four times
• Replit’s fundraising difficulties, and how Paul Graham helped
• The secret lever Replit pulled to scale ahead of its competition
• Replit’s impressive distribution engine

—

Referenced:

• 7 Powers: https://www.amazon.com/7-Powers-Foundations-Business-Strategy/dp/0998116319/
• Codecademy: https://www.codecademy.com/
• Hacker News: https://news.ycombinator.com/
• I Am a Strange Loop: https://www.amazon.com/Am-Strange-Loop-Douglas-Hofstadter/dp/0465030793
• Mythical Man-Month: https://www.amazon.com/Mythical-Man-Month-Software-Engineering-Anniversary/dp/0201835959
• On the Naturalness of Software: https://people.inf.ethz.ch/suz/publications/natural.pdf
• OpenAI: https://openai.com/
• Paul Graham: https://twitter.com/paulg
• Python: https://www.python.org/
• Read Write Own: https://www.amazon.com/Read-Write-Own-Building-Internet/dp/0593731387/
• Replit: https://replit.com/
• Roy Bahat: https://www.linkedin.com/in/roybahat/
• Sam Altman: https://twitter.com/sama
• The Innovator’s Dilemma: https://www.amazon.com/Innovators-Dilemma-Technologies-Management-Innovation/dp/1633691780/
• The Little Schemer: https://www.amazon.com/Little-Schemer-Daniel-P-Friedman/dp/0262560992/
• Y Combinator: https://www.ycombinator.com/

—

Where to find Amjad Masad:

• LinkedIn: https://www.linkedin.com/in/amjadmasad
• Twitter/X: https://twitter.com/amasad

—

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

(02:31) 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.

—

In today’s episode, we discuss:

• Key product strategies used by Square and Gusto
• The pros and cons of building for SMBs
• How to build horizontal after creating a wedge
• The catch with building vertical SaaS
• How product teams can move faster
• Developing product sense and intuition

—

Referenced:

• Alyssa Henry: https://www.linkedin.com/in/alyssa-henry-0905692/
• Copilot: https://copilot.microsoft.com/
• Gokul Rajaram: https://www.linkedin.com/in/gokulrajaram1/
• Gusto: https://gusto.com/
• High Output Management: https://amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884
• Marty Cagan: https://www.linkedin.com/in/cagan/
• Opendoor: https://www.opendoor.com/
• Silicon Valley Product Group: https://www.svpg.com/
• Square: https://squareup.com/
• The Three Horizons Model: https://www.mckinsey.com/enduring-ideas-the-three-horizons-of-growth
• Toast: https://pos.toasttab.com/

—

Where to find Michael Cieri:

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

—

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

(02:41) 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.

—

In this episode, we discuss:

• Common customer success mistakes
• Creating a world-class customer success org
• Tactics for hiring exceptional talent
• How to structure compensation packages
• Where customer success fits into the wider org
• Key early-stage customer success metrics and rituals
• Successful strategies from Box, Medallia, and LinkedIn

—

Referenced:

• Aaron Levie: https://www.linkedin.com/in/boxaaron/
• Box: https://www.box.com/
• David Love: https://www.linkedin.com/in/david-s-love/
• Gainsight: https://www.gainsight.com/
• Jon Herstein: https://www.linkedin.com/in/jonherstein/
• Jonathan Lister: https://www.linkedin.com/in/jonathanlister/
• Ken Fine: https://www.linkedin.com/in/kmfine/
• Medallia: https://www.medallia.com/
• Nick Mehta: https://www.linkedin.com/in/nickmehta/
• Opower: https://www.oracle.com/utilities/opower-energy-efficiency/

—

Where to find Stephanie Berner:

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

—

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

(02:21) 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

Michael Lopp is an experienced engineering leader known for building products at iconic companies like Apple, Borland, Netscape, Palantir, and Slack. Since 2002, Lopp — as he’s more commonly known — has written about engineering, management, and leadership on his popular blog ‘Rands in Repose’. He is also the renowned author of three books: Being Geek, Managing Humans, and The Art of Leadership.

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In today’s episode, we discuss:

• Lopp’s “utopia” — where engineers have time to create and invent
• What makes an excellent engineering leader
• The flexibility required for managerial roles in different contexts
• Navigating internal dynamics between design, engineering, and product
• How to build and grow effective engineering orgs
• The importance of understanding individual motivations
• Key lessons from over 30 years in the industry

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Referenced:

• AOL: https://aol.com
• Apple: https://www.apple.com
• Borland: https://en.wikipedia.org/wiki/Borland
• Netscape: https://en.wikipedia.org/wiki/Netscape
• Palantir: https://www.palantir.com/
• Phillipe Kahn: https://www.linkedin.com/in/philippekahn/
• Pinterest: https://www.pinterest.com/
• Slack: https://slack.com
• Stewart Butterfield: https://www.linkedin.com/in/butterfield/
• Tom Paquin: https://www.linkedin.com/in/tom-paquin-240b4b2/

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Where to find Michael Lopp:

• Blog: https://randsinrepose.com/
• LinkedIn: https://www.linkedin.com/in/michaellopp/
• Twitter/X: https://twitter.com/rands

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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) Beginning career at Borland

(05:41) The difficulty with shipping software at scale

(07:52) Why it’s harder to ship today than ever before

(09:42) What makes a startup operationally sound

(11:23) Why engineers should have concrete time to invent

(19:42) How PMs can improve engineering culture

(21:35) An engineer’s perspective on good product management

(23:36) The role of product compared to design and engineering

(26:38) How micromanagement kills creativity

(29:35) Fostering a debate culture in an org

(31:26) Declarative versus prescriptive leadership

(36:09) 3 ideas on leadership from Lopp’s upcoming book

(38:29) Understanding employee motivation

(42:28) Advice on discovering what motivates people

(46:06) Why teams should reorg every 6 months

(48:32) One thing all successful leaders do

(52:22) Why sound judgment is crucial for decision-making

(53:45) Crystallized lessons from working at software giants

(56:19) Why Lopp is afraid of becoming irrelevant

(57:58) The number one leadership lesson from Lopp’s career

(59:32) What Lopp has changed his mind on over time

(61:12) People who had an outsized impact on Lopp

Kareem Amin is the co-founder of Clay, a lead-generation software that uses AI to scrape 50+ databases and help companies scale their outbound campaigns. Before Clay, Kareem was the VP of Product at The Wall Street Journal. Kareem also co-founded Frame (useframe.com) which was acquired by Sailthru in 2012.

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In today’s episode, we discuss:

• Creating a community of power users
• How to stay ruthlessly focused and make decisions faster
• Clay’s principles for finding product-market-fit
• Why a company is the reflection of its founder’s personality
• Aligning your own psychology with the business
• The mindset change from a first to second-time founder

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Referenced:

• Airtable: https://www.airtable.com/
• Clay: https://www.clay.com/
• Figma: https://www.figma.com/
• Internal Family Systems: https://ifs-institute.com/
• NetSuite: https://www.netsuite.com/
• Notion: https://www.notion.com
• Sailthru: https://www.sailthru.com/

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Where to find Kareem Amin:

• LinkedIn: https://www.linkedin.com/in/kareemamin/
• Twitter/X: https://twitter.com/kareemamin

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Where to find Todd Jackson:

• LinkedIn: https://www.linkedin.com/in/toddj0/
• Twitter/X: https://twitter.com/tjack

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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

(02:36) Clay’s origin story

(05:54) Building for a specific customer

(10:42) Knowing when to build for a broader customer-base

(12:46) The life spiral framework

(15:52) How founders can make better decisions

(18:57) Kareem’s principles for product-market-fit

(25:36) Clay’s customer journey

(30:04) Interesting tactic to find power users

(34:00) How to know you have product-market-fit

(37:11) The impact of founder psychology on the business

(39:41) Mastering commitment to sprints

(40:47) How Kareem’s own personality affected his company

(43:31) Actionable advice to understand founder psychology

(46:25) Why focus is misunderstood

(47:09) The mindset shift from a first to second-time founder

(50:28) What’s next for Clay

(52:14) The best piece of advice Kareem has actioned