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:

Qasar Younis is the co-founder and CEO of Applied Intuition, a leading vehicle intelligence platform that helps companies develop and deploy autonomous systems at scale. In June 2025, the company raised $600M at a $15B valuation. Before Applied Intuition, Qasar was the COO and a group partner at Y Combinator, and earlier founded TalkBin, which was acquired by Google. He’s also held engineering roles at General Motors and Bosch.

Ankur Goyal is the founder and CEO of Braintrust, an end-to-end platform for building AI apps. Before that, he founded Impira, a data management platform that was acquired by Figma, where he went on to lead the AI team. Ankur kickstarted his career when he dropped out of college to join the founding team at SingleStore (formerly MemSQL), a formative experience that shaped his views on building for high-bar users.

In today’s episode, we discuss:

• Ankur’s early lessons on quality from MemSQL

• How frustration with evals at Figma led to Braintrust

• Why they delayed go-to-market (on purpose)

• How to find product-market fit in a new market

• Why building great software comes from a place of “paranoia”

• And much more…

Referenced:

• Airtable: https://www.airtable.com/

• Adam Prout: https://www.linkedin.com/in/adam-prout-0b347630/

• Braintrust: https://braintrust.dev

• Brian Helmig: https://www.linkedin.com/in/bryanhelmig/

• Coda: https://coda.io/

• Databricks: https://www.databricks.com/

• David Kossnick: https://www.linkedin.com/in/davidkossnick/

• Figma: https://www.figma.com/

• Goldman Sachs: https://www.goldmansachs.com/

• Kris Rasmussen: https://www.linkedin.com/in/kristopherrasmussen/

• Manu Goyal: https://www.linkedin.com/in/mngyl/

• MemSQL: https://www.singlestore.com/ (now SingleStore)

• Nikita Shamgunov: https://www.linkedin.com/in/nikitashamgunov/

• OpenAI: https://openai.com/

• Snowflake: https://www.snowflake.com/

• Zapier: https://zapier.com/

Where to find Ankur:

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

• Twitter/X: https://x.com/ankrgyl

Where to find Brett:

• 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

(02:02) Dropping out of college to join MemSQL

(02:24) Key lessons from MemSQL

(05:54) How to build quality software

(08:51) The trick to recruiting well

(12:03) Founding Impira and selling to Figma

(19:45) How Braintrust was born

(25:33) Why good founders are paranoid

(28:08) How to recognize a real market opportunity

(33:37) The biggest mistake at Impira

(35:15) Inside Braintrust’s first six months

(40:57) How AI is reshaping Braintrust’s future

(42:32) The evolution of their prompt playground

(46:53) Fighting to stay mission-driven

(52:45) Make big bets, with extreme clarity

(57:00) The cultural choices that shaped Braintrust

(58:49) Hiring mistakes they won’t repeat

(1:03:07) What PMF really looks like

Tomer London is the co-founder and Chief Product Officer at Gusto, the payroll and people platform used by over 400,000 businesses. He grew up helping run his dad’s clothing store in Israel — an experience that sparked his mission to build better tools for small business owners. After moving to the US for a PhD at Stanford, he met his co-founders and started Gusto.

In today’s episode, we discuss:

Referenced:

Where to find Tomer:

Where to find Brett:

Where to find First Round Capital:

Timestamps:

(00:00) How a childhood around SMBs shaped Tomer’s founder mindset

(03:24) The three things that led to the creation of Gusto

(07:17) Hiring for humility, not just talent

(09:28) The tug-of-war test for product-market fit

(11:58) Why founders should actively seek rejection

(15:34) Gusto’s scrappy customer research: cold calling from a walk-in closet

(17:45) Betting on SMBs – and ignoring investor advice

(20:44) “It’s not an MVP, it’s something that wows people”

(24:09) Serving SMBs vs. startups

(28:36) How to find the right co-founders

(31:09) The weekly co-founder ritual that built trust

(35:02) Reinventing payroll without any prior experience

(38:49) Gusto’s “start small” GTM playbook

(42:16) The big opportunity Gusto wishes they tackled sooner

(43:58) How switching costs became Gusto’s moat

(47:25) The two lucky breaks that gave Gusto an edge

(51:56) What Tomer learned about customers from his dad’s clothing store

David Cramer is the co-founder of Sentry, the leading open-source error monitoring tool used by over 90,000 companies. A self-taught engineer, he went from 9th grade high school dropout and Burger King manager to building one of the most widely adopted developer tools in the world — by working hard and rejecting conventional wisdom. As of 2022, Sentry is valued at over $3 billion. David now serves as Chief Product Officer, after previously holding roles as CEO and CTO.

In this episode, we discuss:

Referenced:

Where to find David:

Where to find Brett:

Where to find First Round Capital:

Timestamps:

(4:01) Learning to code through gaming

(6:31) Dropping out of high school

(9:47) Building infrastructure at Disqus

(10:20) “Software is not that hard”

(12:45) Early interest in open source

(15:45) The birth of Sentry

(23:37) Two common founder mistakes

(27:13) David’s unwavering focus

(28:17) Sentry’s journey to venture backing

(36:43) Finding conviction in decisions

(41:11) How Sentry found PMF

(46:34) More confidence, less ego

(48:08) Is sales valuable?

(51:31) David’s personal philosophy

(1:01:17) Money is not the hardest problem

(1:06:27) Marketing won’t fix a bad product

(1:10:34) What makes Sentry’s market unique

(1:16:24) “You’re gonna mess up”

(1:22:08) Why brand will always matter

(1:30:51) Eliminating all competition