In Depth

Steve Blank is an Adjunct Professor at Stanford University, where he co-created the "Hacking for Defense" curriculum for the Department of Defense. As a consultant to top defense and intelligence organizations, Steve brings cutting-edge strategies to the national security sector. Before entering academia, Steve built eight different startups. He helped launch the Lean Startup movement with his May 2013 Harvard Business Review cover story. Steve also authored the acclaimed business books "The Four Steps to the Epiphany" and "The Startup Owner's Manual.”

This episode’s is guest host is Meka Asonye, a Partner at First Round Capital. Before joining First Round as an investor, Meka led go-to-market teams at both Stripe and Mixpanel.

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In today’s episode we discuss:

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Where to find Steve:

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Where to find Meka:

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Where to find First Round Capital:

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Timestamps:

(00:00) Introduction

(02:27) Validating ideas for defense products

(03:57) Guide to military sales and procurement

(07:15) Rethinking GTM strategies

(10:13) Building a network in national security

(15:07) The dual-use debate

(18:35) Behind the rising number of “defense founders”

(22:30) “Mission solution fit”

(24:35) Breaking new ground in military tech

(26:09) Essential resources for any defense founder

(28:59) What’s missing from Silicon Valley

Anneka Gupta is the Chief Product Officer at Rubrik, a cloud management and data security company with a US$6B market cap. Before Rubrik, Anneka spent 11 years leading various teams at LiveRamp, including product, go-to-market, and operations.

In today’s episode, we discuss:

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Referenced:

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Where to find Anneka Gupta:

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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

(02:11) Inside LiveRamp’s unique growth journey

(12:18) Anneka’s first PM role

(14:20) Leading LiveRamp’s marketing function

(16:17) Why the best product doesn’t win

(21:06) Crafting products for different personas

(24:53) Transitioning Acxiom’s customers to LiveRamp

(33:54) Why Acxiom chose to buy not build

(36:40) Anneka's leap to GM and product leader

(38:22) How 17 diverse roles shaped Anneka’s CPO approach

(40:54) The hidden career growth hack

(43:15) Where domain experience is overrated

(50:33) Mastering the art of altitude shifting

(53:54) PMs should undergo the same training as sales reps

(59:37) Strategies for selling to new personas

(62:40) Lessons from Anneka’s mistake at LiveRamp

(67:56) Who had an outsized impact on Anneka

Matt Lerner is the Founder and CEO at SYSTM, a startup coaching consultancy that helps high-potential companies grow their business. Matt also authored the book “Growth Levers”, which shares his framework that's helped over 200 seed-stage startups grow as much as 100x. Previously, Matt was on the early growth team at PayPal, a partner at 500 Startups, and a guest lecturer at Stanford Business School.

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In today’s episode, we discuss:

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Referenced:

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Where to find Matt Lerner:

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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

(03:11) The hidden truth about startup success

(05:10) Popsa's journey: A case study in growth

(07:31) Breaking down the growth lever framework

(11:30) Understanding the customer's journey

(14:14) The art of customer interviews

(18:07) Unlocking growth through customer insights

(24:23) The triple threat: Founder failure modes

(27:32) The power of founder-led growth strategies

(32:42) Unlocking growth bottlenecks

(36:40) Timing and implementation of growth strategies

(39:43) Founder red flags

(41:32) Crafting effective growth experiments

(43:14) Why customer mindset is the ultimate growth driver

(46:19) The power law of business

(48:59) Why startups don’t need paid marketing

(50:47) Growth levers for sales-driven companies

(53:43) Matt's own application of growth principles

(55:39) Growth levers in B2B sales

(57:05) Finding customer "locksmith moments"

(64:08) The mentor who shaped Matt's thinking

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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Referenced:

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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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Referenced:

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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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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