From Chrome extension to $5B platform | Postman’s journey | Abhinav Asthana (Co-founder & CEO)
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:
Making the leap from India to Silicon Valley
The moment Abhinav realized Postman could win
His principles behind building for developers and non-developers alike
The early monetization experiments that led to their SaaS model
The value of progressive complexity in product design
How community building became a powerful growth lever
And much more…
References:
Abhijit Kane: https://www.linkedin.com/in/abhijitkane/
Adobe: https://www.adobe.com/
Ankit Sobti: https://www.linkedin.com/in/ankit-sobti/
Figma: https://www.figma.com/
Kong Inc.: https://konghq.com/
National University of Singapore: https://nus.edu.sg/
Postman: https://www.postman.com/
Ram Gupta: : https://www.linkedin.com/in/ram-gupta-39b9711/
Slack: https://slack.com/
Stripe: https://stripe.com/
Stewart Butterfield: https://www.linkedin.com/in/butterfield/
Yahoo: http://yahoo.com/
Where to find Abhinav:
LinkedIn: https://www.linkedin.com/in/abhinavasthana/
Twitter/X: https://x.com/a85
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:
(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
--------
1:06:20
--------
1:06:20
How Canva leveraged unconventional growth levers to grow to $42B | Cameron Adams (Co-founder & CPO)
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:
How Canva turned social media managers into early evangelists
Balancing a huge vision with scrappy execution
Hard lessons from their near-silent launch day
The two growth levers that changed everything
And much more…
References:
Adobe: https://www.adobe.com/home
Atlassian: https://www.atlassian.com/
Campaign Monitor: https://www.campaignmonitor.com/
Canva: https://www.canva.com/
Cliff Obrecht: https://www.linkedin.com/in/cliff-obrecht-79ba9920/
Dave Greiner: https://www.linkedin.com/in/davegreiner/
Lars Rasmussen: https://www.linkedin.com/in/larserasmussen/
Melanie Perkins: https://www.linkedin.com/in/melanieperkins/
Mike Cannon-Brookes: https://www.linkedin.com/in/mcannonbrookes/
New York Stock Exchange: https://www.nyse.com/
Pinterest: https://pinterest.com/
Scott Farquhar: https://www.linkedin.com/in/scottfarquhar/
Where to find Cameron:
LinkedIn: https://www.linkedin.com/in/themaninblue/
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/
X/Twitter: https://twitter.com/firstround
YouTube: https://www.youtube.com/@FirstRoundCapital
This podcast on all platforms: https://review.firstround.com/podcast
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
--------
1:04:26
--------
1:04:26
Twitter's former CEO on rebuilding the web for AI | Parag Agrawal (Co-founder and CEO of Parallel)
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:
Why Parallel designs for AI as the primary customer
Lessons from 11 years at Twitter and applying them to a startup
Potential business models to keep the web open for AI
Hiring philosophy: balancing high potential and experienced talent
The evolving role of engineers in an AI-assisted world
Why “agents” are finally becoming useful in production
And much more…
References:
Bloomberg launch coverage: https://www.bloomberg.com/news/articles/2025-08-14/twitter-ex-ceo-parag-agrawal-is-moving-past-his-elon-musk-drama
Clay: https://www.clay.com/
Index Ventures: https://www.indexventures.com/
Josh Kopelman: https://www.linkedin.com/in/jkopelman/
KLA: https://www.kla.com/
OpenAI: https://openai.com/
Parallel: https://parallel.ai/
Patrick Collison: https://www.linkedin.com/in/patrickcollison/
Stripe: https://stripe.com/
Where to find Parag:
LinkedIn: https://www.linkedin.com/in/paragagr/
X/Twitter: https://x.com/paraga
Where to find Todd:
LinkedIn: https://www.linkedin.com/in/toddj0/
X/Twitter: https://x.com/tjack
Where to find First Round Capital:
Website: https://firstround.com/
First Round Review: https://review.firstround.com/
X/Twitter: https://twitter.com/firstround
YouTube: https://www.youtube.com/@FirstRoundCapital
This podcast on all platforms: https://review.firstround.com/podcast
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
--------
1:05:35
--------
1:05:35
Ignoring Silicon Valley advice to build a $3B fintech unicorn | Immad Akhund (Co-founder and CEO of Mercury)
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:
Mercury’s unusual culture playbook – and why it works
How to hire with intention
The trap of weak product-market fit
Shipping under intense pressure during the SVB crisis
And much more…
References:
Airbnb: https://www.airbnb.com/
Andreessen Horowitz: https://a16z.com/
Apple: https://www.apple.com/
Block: https://block.xyz/
Brex: https://www.brex.com/
Chime: https://www.chime.com/
Gusto: https://gusto.com/
Mercury: https://mercury.com/
Paul Graham: https://x.com/paulg
Plaid: https://plaid.com/
Stripe: https://stripe.com/
SVB (Silicon Valley Bank): https://www.svb.com/
True Link Financial: https://www.truelinkfinancial.com/
Varo: https://www.varomoney.com/
Y Combinator: https://www.ycombinator.com/
Where to find Immad:
LinkedIn: https://www.linkedin.com/in/iakhund/
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:
(1:07) Hard-won lessons from serial entrepreneurship
(2:02) You shouldn’t copy-paste advice
(6:57) Why personality trumps culture playbooks
(8:48) How do you hire for cultural fit?
(12:38) The values that shaped Mercury’s DNA
(14:08) The drivers underpinning Mercury’s success
(15:50) The significance of product-market fit
(20:41) Don’t fall into the weak product-market fit trap
(25:49) How to evaluate startup ideas that scale
(30:14) Mercury’s unlikely origin story
(33:51) Breaking into the fintech space
(37:31) Mindset shift: From “This is hard” to long-term gains
(39:43) Building Mercury’s MVP
(44:25) Overcoming early obstacles to reach launch
(47:36) Navigating Mercury’s rapid growth phase
(51:18) Competition isn’t the reason you’re failing
(55:58) Crisis management during the SVB collapse
--------
1:01:52
--------
1:01:52
Inside the ex-YC partner’s $15B self driving car company | Qasar Younis
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.
In today’s episode, we discuss:
• The two founder traits Silicon Valley undervalues
• How to get 1–3 extra months of work done every year
• Lessons from YC on pattern matching and founder feedback
• The battle-tested startup formula Qasar used at Applied
• Why co-founder fit is make-or-break
• Applied’s playbook: vertical SaaS, product-led GTM, and leveraging VC networks
• Why Applied went multi-product in the early days
• Contrarian takes on startup culture, compensation, and cost control
• Why domain expertise is making a comeback
• And much more…
Referenced:
• Applied Intuition: https://www.appliedintuition.com
• Ansys: https://www.ansys.com
• Bilal Zuberi: https://www.linkedin.com/in/bzuberi
• Bosch: https://www.bosch.com
• Elad Gil: https://www.linkedin.com/in/eladgil
• General Motors: https://www.gm.com
• “Google’s Acquisition of TalkBin”: https://techcrunch.com/2011/04/25/google-acquires-talkbin-a-feedback-platform-for-businesses-thats-only-five-months-old/
• “High Output Management”: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884
• Kyle Vogt: https://x.com/kvogt
• Marc Andreessen: https://x.com/pmarca
• “Only the Paranoid Survive”: https://www.amazon.com/Only-Paranoid-Survive-Strategic-Inflection/dp/0385483821
• Paul Graham: https://x.com/paulg
• Peter Ludwig: https://www.linkedin.com/in/peterwludwig
• Sam Altman: https://x.com/sama
• TalkBin: https://www.crunchbase.com/organization/talkbin
• “The History of the Standard Oil Company”: https://www.amazon.com/History-Standard-Oil-Company-Volumes/dp/1519455860
• Waymo: https://waymo.com
• Y Combinator: https://www.ycombinator.com
• Zoox: https://zoox.com
Where to find Qasar:
• LinkedIn: https://www.linkedin.com/in/qasar/
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:
(01:26) Two founder traits Silicon Valley undervalues
(04:23) Gain 1-3 extra months of productivity yearly
(05:52) Why founders should read outside the startup canon
(07:27) Lessons from YC
(13:44) Why it's harder to start than to quit
(15:52) The moment you become a real founder
(20:24) How great founders master luck
(21:46) Qasar’s battle-tested startup formula
(25:37) The founding insight for Applied
(31:42) How Applied expanded beyond automotive
(38:05) Why Applied went multi-product early
(45:45) What no one says about startup secondaries
(49:02) Why being cheap is a startup superpower
(51:04) The myth of "competition doesn’t matter"
(53:50) Early scrappiness: The Sunnyvale house setup
(54:50) Why domain knowledge is making a comeback
(58:32) The mentors who shaped Qasar
Welcome to In Depth, a new podcast from First Round Review that’s dedicated to surfacing the tactical advice founders and startup leaders need to grow their teams, their companies and themselves. Hosted by Brett Berson, a partner at First Round, In Depth will cover a lot of ground and a wide range of topics, from hiring executives and becoming a better manager, to the importance of storytelling inside of your organization. But every interview will hit the level of tactical depth where the very best advice is found. We hope you’ll join us. Subscribe to “In Depth” now and learn more at firstround.com
Ireland