From dorm room to life-saving AI | Prepared’s story | Michael Chime (Co-founder & CEO of Prepared)
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.
In this conversation, Michael joins Meka to share the inside story of building in a tough market, the counterintuitive strategies used to crack government procurement, and why their mission is a competitive moat.
In today’s episode, we discuss:
Why school shootings were the catalyst for building safety software
Navigating the most challenging customer base: government and public safety agencies
Why Prepared gave away its first product for free — for years
Lessons from evolving a wedge product into an AI-driven suite
How Michael balanced conviction with customer feedback
Building long-term investor relationships
Staying true to the mission through headwinds and tailwinds
And much more…
Where to find Michael:
LinkedIn: https://www.linkedin.com/in/michaelchime/
Where to find Meka:
LinkedIn: https://www.linkedin.com/in/mekaasonye/
Twitter/X: https://x.com/bigmekastyle
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
References:
Axon: https://www.axon.com/
Dylan Gleicher: https://www.linkedin.com/in/dylan-gleicher/
March for Our Lives: https://marchforourlives.org/
Neal Soni: https://www.linkedin.com/in/neal-soni/
OpenAI: https://openai.com/
Peter Thiel Fellowship: https://thielfellowship.org/
Prepared: https://www.prepared911.com/
Sam Altman: https://x.com/sama
Slack: https://slack.com/
Uber Eats: https://www.ubereats.com/
Yale University: https://www.yale.edu/
Timestamps:
(3:03) Staying mission-oriented under pressure
(3:54) Negotiating an acquisition from a hospital bed
(06:25) How Sandy Hook shaped the Prepared story
(09:15) From school safety app to 911 platform
(10:02) Why are 911 systems so outdated?
(13:02) Prepared’s first product iteration
(16:04) Why attempt to tackle the govtech market?
(18:36) Mission as fuel: staying resilient through endless rejections
(20:03) Should young people drop out of college?
(23:10) How Michael nurtured a learner’s mindset
(25:23) Forging unwavering founder conviction
(31:41) Landing Prepared’s first user
(32:39) “I want to be terrible at sales”
(34:35) Expanding to a premium product line
(36:55) Leveraging AI to expand the product surface area
(41:49) How much should you listen to customers?
(45:35) Building in headwinds vs. tailwinds
(47:18) Navigating partnerships and competition
(54:52) Michael’s unconventional approach to fundraising
(1:02:54) Has Prepared found product-market fit?
(1:04:00) Reflecting on the founder journey
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1:09:07
Saying yes to everything: How customer obsession built Samsara | Kiren Sekar (CPO)
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:
Lessons from Meraki’s acquisition by Cisco
How Kiren hires for intrinsic motivation
Why Samsara was built for operations industries
The early hardware prototype and the Cowgirl Creamery insight
Building broad vs. niche from day one
The shift from founder-selling to a scalable sales motion
Organizing product teams around revenue vs. experience
How Samsara uses LLMs and AI today
What Kiren learned from longtime co-founder Sanjit Biswas
Where to find Kiren:
LinkedIn: https://www.linkedin.com/in/kirensekar/
Where to find Brett:
LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/
Twitter/X: https://twitter.com/brettberson
References:
Cisco: https://www.cisco.com/
Clay: https://www.clay.com/
Cowgirl Creamery: https://cowgirlcreamery.com/
IBM: https://www.ibm.com/
Meraki: https://meraki.cisco.com/
Microsoft: https://www.microsoft.com/
Salesforce: https://www.salesforce.com/
Samsara: https://www.samsara.com/
Sanjit Biswas: https://www.linkedin.com/in/sanjitbiswas/
Uber: https://www.uber.com/
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
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1:08:57
Starting an education giant in a “bad market” | ClassDojo’s story | Sam Chaudhary (Co-founder and CEO)
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:
Why ClassDojo was built for consumers (teachers, students and parents) instead of schools
How ClassDojo grew entirely by word-of-mouth
Sam’s unusual approach to building multiple new businesses
The founder mindset required to build an industry leader
Why relentless resourcefulness is an underrated skill
And much more…
References:
Accel: https://www.accel.com/
Airbnb: https://www.airbnb.com/
Bill Gates: https://www.linkedin.com/in/williamhgates/
Brendan Kereiakes: https://www.linkedin.com/in/product/
ClassDojo: https://www.classdojo.com/
Dominick Bellizzi: https://www.linkedin.com/in/dominickbellizzi/
Geoff Ralston: https://www.linkedin.com/in/geoffralston/
Gonzalo Aguilar Málaga: https://www.linkedin.com/in/gonzalodecheck/
Hamilton Helmer: https://www.linkedin.com/in/hamilton-helmer-42983/
Imagine K12: https://www.imaginek12.com//
Khan Academy: https://www.khanacademy.org/
Liam Don: https://www.linkedin.com/in/liamdon/
McKinsey: https://www.mckinsey.com/
Paul Graham: https://x.com/paulg
Plaid: https://plaid.com/
Reid Hoffman: https://www.linkedin.com/in/reidhoffman/
Roblox: https://www.roblox.com/
Sal Khan: https://www.linkedin.com/in/khanacademy/
Superhuman: https://superhuman.com/
Tim Brady: https://www.linkedin.com/in/tim-brady-7a632510/
Y Combinator: https://www.ycombinator.com/
Where to find Sam:
LinkedIn: https://www.linkedin.com/in/samchaudhary/
Twitter/X: https://x.com/samchaudhary
Where to find Brett:
LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/
Twitter/X: https://twitter.com/brettberson
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
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1:12:29
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
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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
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
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