In Depth

Adam Guild is the co-founder and CEO at Owner, an online food ordering system for independent restaurants. Within a year, Owner went from being about to run out of money to having hundreds of customers. Last year, they raised a $33M Series B.

Adam’s entrepreneurial journey began as a teenager when he built a successful Minecraft server, which led him to drop out of high school to become a founder. His passion for helping small businesses was sparked by his mom’s struggles running a dog grooming shop, which led him to launch the early iteration of Owner.

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In today’s episode, we discuss:

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Referenced:

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Where to find Adam:

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

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Where to find Brett:

Where to find First Round Capital:

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Timestamps:

(00:00) Intro

(01:29) Adam’s first business

(04:15) The transition from Minecraft to Owner

(05:58) The dark side of the gaming industry

(14:20 Adam’s scrappy strategy to landing his first customers

(16:52) The COVID pivot

(21:31) The quest to find product-market fit

(30:53) What actually worked to get new customers

(36:03) Inside Owner’s explosive growth

(46:41) How Owner secured its crucial first round of funding

(53:34) The bet on going multi-product

(64:28) What Adam wishes he knew at 17

(76:22) Sales-led vs. product-led growth

Eeke de Milliano is the Head of Global Product at Stripe, helping drive innovation and success in the company's product line. Before this role, she was Head of Product at Retool and co-founded Constellate. Eeke previously spent 6 years as Product Lead at Stripe, working with the company during their hyper-growth era.

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In today’s episode, we discuss:

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Referenced:

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Where to find Eeke:

• LinkedIn: https://www.linkedin.com/in/eeke-de-milliano-3b05a629/

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Where to find Brett:

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Where to find First Round Capital:

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Timestamps:

(00:00) Should you ‘buy or build’ a leader

(03:45) Why do executive hires fail so often?

(09:35) Why the stakes are so high for leadership hires

(12:26) The hardest document Eeke ever wrote

(14:06) Two red flags in a new hire

(17:27) An example of an outstanding leader

(21:40) What creates dysfunctional exec relationships

(22:38) The three steps towards hiring successful leaders

(30:30) What you should know about outside hires

(33:12) Eeke’s advice for easing leadership transitions

(42:06) How to notice success patterns

(47:21) Why high-functioning executive teams are like parents

(52:02) The most surprising lesson from Eeke’s first stint at Stripe

(55:11) The leadership data Eeke wishes we had

Kevin Busque is the co-founder and CEO of Guideline, a 401(k) management company revolutionizing the retirement space for small and medium-sized businesses. Prior to Guideline, Kevin co-founded Taskrabbit, where he encountered firsthand the complexity and low participation rates of traditional 401(k) plans—largely due to confusing fee structures.

After launching Guideline to address those problems head-on, the company has seen remarkable growth, hitting $120 million in ARR by June 2024. In this conversation, Kevin shares pivotal moments that shaped Guideline’s trajectory, including a strategic partnership with Gusto. He also explains how his “Do the hard thing first” mindset helped the team build an industry-leading platform and disrupt an entrenched market.

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Referenced:

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Where to find Kevin:

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

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Where to find Brett:

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Where to find First Round Capital:

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Timestamps:

(00:00) Teaser: “I don’t believe in stealth mode”

(02:51) Inspiration behind Guideline

(07:56) Lessons from a year’s research before Guideline

(10:44) Identifying market pull for Guideline

(14:28) What Kevin learnt before shipping their first product

(19:10) How Guideline set their fees up

(27:51) The surprising range of Guideline’s early customers

(31:48) Kevin’s insights from the Gusto integration

(39:48) Guideline’s first year

(44:44) Working with Plaid as Guideline’s first customer

(53:28) Guideline’s auto-enrollment feature

(57:53) Lucky 8: Kevin’s unexpected pricing strategy

(62:04) Franchise opportunities

(64:49) Kevin’s reflections on Taskrabbit

(71:36) Will Guideline ever go multi-product?

(72:37) Kevin’s take on product-market fit

(73:30) Guideline’s compounding advantage

(78:51) The challenges faced by introverted leaders

Bill Magnuson is the co-founder and CEO at Braze, along with Kevin Wang, who joined as employee #8 and serves as the CPO. The two MIT graduates have built Braze into a publicly listed customer engagement platform with a $4.4B market cap. In 2023, Braze surpassed $500M in CARR, and serves over 2,200 customers worldwide. Before Braze, Bill spent time at Bridgewater Associates. Kevin’s academic background is in brain & cognitive sciences, and prior to joining Braze he worked at Accenture and Brewgene.

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In today’s episode, we discuss:

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Referenced:

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Where to find Bill:

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Where to find Kevin:

• LinkedIn: https://www.linkedin.com/in/kevin-wang-96131916/

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Where to find Brett:

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Where to find First Round Capital:

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Timestamps:

(00:00) Teaser: Finding “terminal value” product market fit

(00:24) Introduction

(02:34) Bill's insights into the mobile revolution

(04:43) Lessons from Bridgewater Associates

(09:12) First principles thinking in action at Braze

(14:14) Meeting co-founders at an NYC Hackathon

(24:35) Braze’s scrappy scaling

(33:37) Early product development

(39:37) From 1,000 beta signups to 2,200+ paying customers

(43:51) Braze’s fundraising struggles

(47:01) Breaking the rules of a lean startup

(53:02) Riding the mobile wave to success

(60:02) Building a global customer base

(64:04) The never-ending quest for PMF

(70:29) 3 things every founder needs to know

(73:56) Navigating competition like a boxer

(79:03) When scale helps or hurts

(80:32) 1 thing they’ve learned from each other

Varun Anand is the co-founder and Head of Operations at Clay, a GTM development environment that combines data and AI to help over 5000 companies power everything from CRM enrichment to highly targeted outreach campaigns. Clay recently announced their Series B expansion, raising $40M at a $1.25B valuation. Before Clay, Varun was the Director of Operations at Newfront and the Head of Expansion at Candid. Varun also spent four years working on Hillary Clinton’s presidential campaign.

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In today’s episode, we discuss:

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Referenced:

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Where to find Varun:

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Where to find Brett:

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Where to find First Round Capital:

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Timestamps:

(00:00) Teaser + Introduction

(03:13) Turning traditional GTM on its head

(05:37) How Clay hustled for its first customers: Reddit threads & WhatsApp groups

(08:53) Unpacking Clay's credit-based pricing

(14:29) Building Clay's self-serve engine

(16:54) Why Clay rejected the usage-based model

(19:04) Clay’s big bet on content

(23:59) How "reverse demos" win enterprise deals

(27:49) 3 changes that unlocked Clay's upmarket motion

(36:59) How to build trust with enterprise buyers

(38:49) Applying the land and expand model

(40:40) Hiring people who are “technical enough”

(46:33) Inside Clay’s hands-on interviewing process

(48:15) Why Clay invested in brand from day-one

(50:21) Clay’s contrarian take on compensation

(58:35) The person who shaped Varun’s career

Tristan Handy is the Founder and CEO at dbt Labs, a cloud-based data management platform that has raised over $400M to date, and was last valued at $4.2B in 2022. Dbt Labs has grown from just three companies using its free tool in 2016 to an ecosystem of 30,000+ enterprise users. Before founding dbt Labs, Tristan was the VP of Marketing at RJMetrics and the Director of Operations at Squarespace.

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In today’s episode, we discuss:

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Where to find Tristan:

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Where to find Brett:

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Where to find First Round Capital:

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Timestamps:

(00:00) Introduction

(02:56) The critical oversight in data analysis

(05:41) Becoming an “accidental founder”

(07:04) Inside the unique decision to start a consultancy

(08:17) The game-changing principle behind dbt Labs’ rapid growth

(11:20) Finding dbt Labs’ first customers

(15:52) Consulting's hidden scalability

(17:25) How dbt Labs created a new category

(21:03) The anti-demo strategy

(23:59) Community hacking: the Slack group that changed everything

(26:00) The open source philosophy

(27:39) When growth went exponential

(28:49) How consulting engagements shaped the roadmap

(30:02) Fundraising only when “things started to break”

(32:40) Consultancy superpowers: the hidden advantages

(34:04) Pivoting from consulting to software

(40:00) Key monetization strategies

(48:56) Why “begrudging” CEOs can be successful

(51:02) Advice for finding PMF: “It’s not a playbook”

(51:59) Lowering your standards is a hack

(53:30) Navigating emotional overwhelm

(54:25) Every CEO needs a coach

Yuhki Yamashita is the Chief Product Officer at Figma, leading the product and design teams. Previously, he was a product and design leader at Uber, where he orchestrated the redesign of the rider and driver apps. Yuhki was also a product manager at Google (YouTube iOS app) and Microsoft (Hotmail). Additionally, he has taught introductory computer science at Harvard University.

In today’s episode, we discuss:

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Referenced:

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Where to find Yuhki:

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Where to find Brett:

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Where to find First Round Capital:

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(00:00) Introduction

(02:50) Figma's early days

(09:11) Product culture across companies

(13:42) Knowing when to change things

(17:40) How business goals impact product expansion

(21:00) Advice for going multi-product

(24:30) The skills of a “0 to 1” PM

(27:36) Identifying entrepreneurial talent

(29:06) Why aren't there more designer founders?

(35:22) How Figma launches new products

(41:19) “0 to 1” versus “1 to 10” talent

(46:01) The role of storytelling at Figma

(49:22) How Figma prioritizes product

(55:11) Advice for product storytelling

(59:02) “Good” vs “extraordinary” product managers

(61:21) Why product simplicity matters

(63:52) The importance of taste in product and design

(67:56) The biggest influence on Yuhki’s product thinking

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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Referenced:

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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