Zack Kanter is the founder and CEO of Stedi, an API-first healthcare clearinghouse. After bootstrapping a wildly profitable auto-parts business, he sold it to tackle "the most complicated problem" he'd ever encountered: business-to-business transaction exchange. He spent years building EDI infrastructure, threw away the entire codebase eight times, and found extraordinary traction in healthcare. Stedi recently raised a $70M Series B co-led by Stripe and Addition. In this conversation, Brett and Zack discuss why venture capital means "going pro," why execution is never actually a moat, and how "eating glass" became Stedi's competitive advantage.

In today’s episode, we discuss:

Where to find Zack:

Where to find Brett:

Where to find First Round Capital:

References:

Timestamps:

(01:24) Zack’s first business

(08:54) Why the first customer is tricky

(10:12) The downside of bootstrapping

(11:42) Why venture capital is like “going pro”

(14:20) The confusion between ownership vs. control

(16:08) Building a company you don’t want to leave

(20:46) Do things better than other people

(24:49) Stedi’s early years

(31:43) Physical vs. digital product-market fit

(34:41) How Stedi scaled decision-making

(40:08) Stedi’s journey to product-market fit

(45:22) Finding founder-approach fit

(50:42) “All software is a cascade of miracles”

(52:52) The surprising lessons from discount retail

(57:50) How the Toyota production system influences software

(1:01:31) What it means to be a high-agency person

(1:03:09) The core trait Zack looks for when hiring

(1:02:57) Maintaining conviction in unconventional practice

(1:14:19) When should you start to hire managers?

(1:17:42) “Reality has a surprising amount of detail”

Jake is the founder and CEO of Serval, an AI-driven IT automation and service management platform that just raised $47M in Series A funding this week. Before founding Serval, Jake spent over five years at Verkada, where he led multiple products from 0-1 and helped scale the company across hardware and software. His years at Verkada taught him that winning in enterprise means delivering consumer-quality experiences to business buyers — a lesson that shapes how Serval turns complex IT automation into something that feels magical.

In this episode, Jake and Brett dive into the lessons from Verkada that inspired Serval's founding, what it takes to disrupt entrenched enterprise categories, and practical tips for getting deeply embedded with customers and hiring high-quality candidates.

In today’s episode, we discuss:

Where to find Jake:

Where to find Brett:

Where to find First Round Capital:

References:

Timestamps:

(02:25) Lessons from holding different product roles

(07:29) Turning “hard mode” into a moat

(10:49) The early days of Serval

(12:59) Scratching the founder itch

(14:57) Unconventional interview techniques

(17:47) Solving core interview challenges

(21:10) Planning the early product roadmap

(23:03) The surprising power of patience

(26:12) Serval’s impressive technical advantage

(27:35) Disrupting legacy incumbents

(31:13) Building for mid-market and enterprise

(33:35) Serval’s enduring roadmap

(36:08) How to sell to an existing market

(39:16) The evolving role software plays

(43:55) Building for AI that didn’t exist yet

(49:49) Serval’s forward-deployed engineers

(58:31) The hybrid PM-GM

(1:00:27) “You can over-prioritize”

(1:02:48) The unexpected value of panic buttons

(1:04:50) What Serval looks for in new talent

(1:07:01) The ultimate hiring litmus test

(1:13:59) Building out Serval’s go-to-market function

(1:16:31) The evolving IT market in 2025

Gorkem Yurtseven is the co-founder and CTO of fal, the generative media platform powering the next wave of image, video, and audio applications. In less than two years, fal has scaled from $2M to over $100M in ARR, serving over 2 million developers and more than 300 enterprises, including Adobe, Canva, and Shopify. In this conversation, Gorkem shares the inside story of fal's pivot into explosive growth, the technical and cultural philosophies driving its success, and his predictions for the future of AI-generated media.

In today's episode, we discuss:

Where to find Gorkem:

Where to find Todd:

Where to find First Round Capital:

References:

All images and videos generated using models run on fal.ai

Timestamps:

(01:43) The generative media industry

(02:29) From $2M to $100M ARR: fal's explosive year

(04:06) How Gorkem met co-founder Burkay Gur

(05:38) The hardest decision that saved the company

(09:52) Spotting the opportunity in generative media

(13:28) Turning Todd into George Clooney

(15:29) The early adopters of the first fal product

(17:54) The transition from toy to tool

(19:27) Why 2025 is the year of AI-generated video

(21:44) Staying nimble as a 45-person company

(24:42) Predicting AI-generated film in 2027

(27:24) Why generative media is a greenfield market

(30:33) fal’s greatest optimization wins

(34:42) Why fal has 500 Slack channels

(36:02) Competing in a fast-moving, fragmented market

(42:06) How to build a world-class team

(47:24) Learning sales as a technical founder

(50:55) How fal built a brand without a marketer

(53:21) The story behind "GPU Rich / GPU Poor"

(54:22) Inside fal’s rule-breaking playbook

(56:09) The hardest part of scaling fal

Michael is the co-founder and CEO of Prepared, the AI assistant for 911 calls that helps dispatchers capture information faster, translate emergency calls in real time, and deliver lifesaving context to first responders. Founded out of Yale in 2019, Prepared grew from a school safety app into a critical platform for emergency communications, disrupting a notoriously tough market. This mission-driven journey just reached a major milestone: Prepared was acquired by Axon, the global public safety technology company.

Where to find Michael:

Where to find Meka:

Where to find First Round Capital:

References:

Timestamps:

(3:03) Staying mission-oriented under pressure

Kiren Sekar is the CPO of Samsara, a company that brings real-time visibility, analytics, and AI to physical operations. Before Samsara, Kiren was an early leader at Meraki, which was acquired by Cisco for $1.2B.

In this episode, he walks us through Samsara’s origin story: from hardware hacking in a basement to scaling a cross-industry IoT platform. He shares how early customer feedback loops led to the company’s first product, why starting with the mid-market was a deliberate choice, and how Samsara kept a startup mindset even as it scaled.

In this episode, we discuss:

Where to find Kiren:

Where to find Brett:

References:

Timestamps:

(01:27) Meraki’s growth and acquisition by Cisco

(03:25) The "evaporating" exit strategy from Meraki

(04:42) Identifying the IoT market gaps

(07:38) The early keys to success at Samsara

(09:39) What does quality mean to Kiren?

(10:54) Building a customer-centric roadmap

(17:34) Early customer research and the failed fridge monitoring idea

(20:57) How a cheese producer helped create Samsara’s first prototype

(28:06) Balancing depth and breadth in customer profiles

(33:45) Developing customer trust to build feedback loops

(40:27) How “ease of use” became a growth secret

(44:23) Pricing strategies and market positioning

(51:51) How Meraki influenced Samsara’s GTM strategy

(57:19) Helping customers navigate change management

(1:00:48) How Samsara’s team evolved during rapid growth

(1:04:03) What AI means for an IoT giant

Sam Chaudhary is the co-founder and CEO of ClassDojo, a multi-product education platform used in 95% of U.S. schools and over 180 countries globally to connect teachers, students, and families. In this episode, Sam shares the full arc of building ClassDojo, from early skepticism about education and a failed group-making tool, to creating a communication platform loved by millions.

In this episode, we discuss:

References:

Where to find Sam:

Where to find Brett:

Timestamps:

(01:36) Why education is a “bad market”

(02:52) Why enterprise education is broken

(03:35) Building for families, not schools

(06:53) Early challenges and insights

(09:45) Sam’s unusual background

(11:42) Meeting co-founder Liam at a hackathon

(13:22) Getting into Imagine K12 with a group-making tool

(19:47) The conversation with Reid Hoffman that changed everything

(21:52) Building a network to reach more families

(23:30) Scaling by building a community

(33:18) Designing for delight and word-of-mouth growth

(40:09) Launching the first monetization feature after 7 years

(41:35) How to pick markets and when to go broad

(46:04) The explosive expansion into the tutoring industry

(55:11) Creating safe online spaces for kids

(58:01) Harnessing AI in education

(59:52) Lessons from ClassDojo’s playbook

Abhinav Asthana is the co-founder and CEO of Postman, the world's leading API collaboration platform used by millions of developers and thousands of companies. What began as a personal itch, a simple Chrome extension Abhinav built to make his own API work easier, became a global phenomenon within weeks.

In this episode, we discuss:

References:

Where to find Abhinav:

Where to find Brett:

Where to find First Round Capital:

Timestamps:

(01:18) Why early computer access changed everything

(03:39) The first taste of the entrepreneurial bug

(09:58) Building BITS360 in college

(11:14) Curating entrepreneurial taste

(15:49) The ventures that didn’t make it

(20:53) The problems that preceded Postman

(29:56) How Postman’s team was formed

(34:01) Why clear roles prevent chaos

(34:50) Scrappy startup life in the early days

(36:26) Postman’s path to monetization

(39:59) Building a truly collaborative platform

(43:00) Navigating market and customer needs

(46:02) Cracking the go-to-market code

(49:39) Bridging the developer-enterprise divide

(54:43) The open-source dilemma

Cameron Adams is the co-founder and Chief Product Officer at Canva, the design platform valued at $42B as of July 2025, used by over 230 million people every month.

Before starting Canva, Cameron was a designer and engineer at Google and co-founded Fluent, an email startup. In this episode, Cameron walks through Canva’s earliest days — from the remarkably fast courtship with co-founders Melanie Perkins and Cliff Obrecht, to the counterintuitive product decisions that helped Canva instantly resonate with users who thought they would never design anything.

In this episode, we cover:

References:

Where to find Cameron:

Where to find Brett:

Where to find First Round Capital:

Timestamps:

(01:24) The birth of Canva

(04:32) Meeting Canva’s co-founders

(11:22) Building the first iteration of Canva

(15:26) The discovery that changed prototyping

(20:48) Why onboarding was the unlock for retention

(27:36) The anticlimactic launch day

(32:43) How word-of-mouth spurred early retention

(36:33) Targeting different user personas

(41:02) Building a community on social media

(43:38) Two impactful growth levers

(47:14) Why Canva should have gone mobile sooner

(48:12) What underpins Canva’s dominance today

(53:37) Rebuilding for enterprise

(58:38) Lessons from Canva’s tough times

Parag Agrawal is the co-founder and CEO of Parallel, a startup building search infrastructure for the web’s second user: AIs. Before launching Parallel, Parag spent over a decade at Twitter, where he served as CTO and later CEO during a period of intense transformation, as well as public scrutiny.

In this episode, Parag shares what he learned from his time at Twitter, why the web must evolve to serve AI at massive scale, how Parallel is tackling “deep research” challenges by prioritizing accuracy over speed, and the design choices that make their APIs uniquely agent-friendly.

We also discuss:

References:

Where to find Parag:

Where to find Todd:

Where to find First Round Capital:

Timestamps:

(1:26) Founding Parallel with an AI-first mission

(3:23) From Twitter CTO/CEO to startup founder

(6:20) What the AI era spells for companies

(7:58) The CEO to founder pipeline

(11:18) Reflections on Twitter’s transformation

(17:48) How Parallel was born

(22:31) Early use cases for Parallel

(31:42) How has Parallel’s ICP changed?

(34:37) AI’s impact on competitor dynamics

(36:06) When should founders launch?

(37:43) Parag’s fundraising framework

(40:14) Building a high-impact engineering team

(44:49) Counterproductive uses of AI

(47:35) How will the software engineer role evolve?

(49:10) How are Parallel’s customers using AI?

(53:27) Defining agents in 2025

(55:02) Parallel’s long-term vision

(1:03:43) Parag’s growth as a founder

Immad Akhund is the CEO and co-founder of Mercury, a digital banking platform that’s become the go-to financial infrastructure for startups. Before Mercury, Immad spent nearly two decades founding companies, learning the hard way what separates a good idea from a great business.

In this episode, Immad shares the hard-earned lessons from launching Mercury as his third startup. He unpacks how he recognized this was the right idea to pursue, what strong product-market fit feels like, and why trying to "iterate" your way to success often leads founders astray.

In this episode, we discuss:

References:

Where to find Immad:

Where to find Brett:

Where to find First Round Capital:

Timestamps: