How to build a company you’ll run forever | Zack Kanter (Founder and CEO of Stedi)
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:
How 16-year-old Zack turned $2,500 into a wholesale empire
Why bootstrapping means being "constrained by capital" and how VC removes that ceiling
Why Zack rebuilt their EDI product eight times before launch
The snake swallowing a deer: what extreme product-market fit really looks like
What software companies can learn from discount retail and Toyota
Why Stedi’s new hires are told "everything’s your fault now"
And much more
Where to find Zack:
LinkedIn: https://www.linkedin.com/in/zkanter
Twitter/X: https://x.com/zackkanter
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
References:
Aetna: https://www.aetna.com/
Amazon: https://www.amazon.com/
AWS: https://aws.amazon.com/
Blue Cross Blue Shield: https://www.bcbs.com/
Change Healthcare: https://www.changehealthcare.com/
Cigna: https://www.cigna.com/
Clay: https://www.clay.com/
Costco: https://www.costco.com/
Ford Motor Company: https://www.ford.com/
GM: https://www.gm.com/
HIPAA overview (HHS): https://www.hhs.gov/hipaa/index.html
Jeff Bezos: https://x.com/JeffBezos
Kanban / TPS (Toyota): https://global.toyota/en/company/vision-and-philosophy/production-system
Microsoft Teams: https://www.microsoft.com/microsoft-teams
NetSuite: https://www.netsuite.com/
O’Reilly Auto Parts: https://www.oreillyauto.com/
Peter Thiel: https://x.com/peterthiel
Porter’s five forces: https://www.isc.hbs.edu/strategy/pages/the-five-forces.aspx
"Reality has a surprising amount of detail": https://johnsalvatier.org/blog/2017/reality-has-a-surprising-amount-of-detail
Slack: https://slack.com/
Stedi: https://www.stedi.com/
Summit Racing: https://www.summitracing.com/
Target: https://www.target.com/
Walmart: https://www.walmart.com/
Zapier: https://zapier.com/
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”
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1:24:09
Go hard early: How lessons from Verkada shaped Serval's AI agents for IT teams | Jake Stauch (Founder and CEO)
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:
Why building “in existing categories” can be more powerful than creating new ones
The lessons from Verkada that shaped Serval's platform strategy
The customer interview question that unlocked the IT buyer’s hidden pain points
How Serval's automation builder uses AI to generate code-based workflows
Redefining engineering and PM roles with forward-deployed engineers
Keeping the hiring bar high in an AI-native startup
Why there’s a “land grab” moment right now in enterprise AI
And much more...
Where to find Jake:
LinkedIn: https://www.linkedin.com/in/jakestauch/
Twitter/X: https://x.com/jakeserval
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
References:
Alex McLeod: https://www.linkedin.com/in/alexmcleodio/
Clay: https://www.clay.com
Cloudflare: https://www.cloudflare.com
Cursor: https://cursor.sh
Filip Kaliszan: https://www.linkedin.com/in/kaliszan/
Hans Robertson: https://www.linkedin.com/in/hansrobertson
Linear: https://linear.app
Okta: https://www.okta.com
Rippling: https://www.rippling.com
Serval: https://www.serval.com/
ServiceNow: https://www.servicenow.com
Verkada: https://www.verkada.com
Workday: https://www.workday.com
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
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1:23:01
The pivot that paid off: How fal found explosive growth in generative media | Gorkem Yurtseven (Co-founder and CTO)
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:
How fal pivoted from data infrastructure to generative inference
fal’s explosive year and how they scaled
Why "generative media" is a greenfield new market
fal's unique hiring philosophy and lean <50-person team
Building a brand that resonates with developers
What the world looks like in 2027 when AI-generated video becomes mainstream
And much more…
Where to find Gorkem:
LinkedIn
X / Twitter
Where to find Todd:
LinkedIn
X / Twitter
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:
Adobe: https://www.adobe.com/
Amazon: https://www.amazon.com/
Anthropic: https://www.anthropic.com/
Base10: https://base10.vc/
Black Forest Labs: https://blackforestlabs.ai/
Burkay Gur: https://www.linkedin.com/in/burkaygur/
Canva: https://www.canva.com/
Clay: https://www.clay.com/
Coinbase: https://www.coinbase.com/
Cursor: https://www.cursor.com/
DALL-E: https://openai.com/dall-e-2
Databricks: https://www.databricks.com/
Dylan Patel: https://www.linkedin.com/in/dylanpatelsa/
fal: https://fal.ai/
Google DeepMind: https://deepmind.google/
LLaMA: https://ai.meta.com/llama/
OpenAI: https://openai.com/
Oracle: https://www.oracle.com/
Perplexity: https://www.perplexity.ai/
Shopify: https://www.shopify.com/
Snowflake: https://www.snowflake.com/
Sora: https://openai.com/sora
Stable Diffusion XL (SDXL): https://stability.ai/stable-diffusion
Stability AI: https://stability.ai/
Together AI: https://www.together.ai/
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
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59:18
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
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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