We Built It Because We Had To

S1 E36 | Everyone Ignored In-House Legal. He Built Its Operating System. | Evan Wong, Checkbox

Evan Wong built Checkbox to automate legal intake and workflow for enterprise in-house legal teams.

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S1 E35 | Nobody Wanted His Sales Playbooks. They Wanted the Recorder. | Gerald Zankl, Kickscale

Gerald Zankl built Kickscale to help European B2B sales teams capture customer conversations and stop wasting time on non-selling work.

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Why AppSec Tools Catch 15% of Defects (And How to Prioritize What Matters)

Dr. Chris Near explains why application security tools catch only 15% of defects and how to prioritize vulnerabilities by financial risk.

Why Salesforce Implementations Fail (And How AI Changes Consulting) | Stephanie Taylor

Stephanie Taylor explains why enterprise software implementations fail and how AI is transforming consulting and process design.

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Circular Commerce: How Enterprise Retailers Turn Returns into Profit

Ricardo Morgado of Getloopos discusses building LoopOS to transform returns into profit centers for enterprise retail.

S1 E30 | Does Your AI Assistant Have a Personality? | Daniele Bernardi, Toolhouse

Daniele Bernardi founded Toolhouse to create cost-effective AI workers for repetitive tasks across communication platforms.

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How Enterprise Brands Automate Social Media Comments with AI (Without Sounding Fake)

Hank Leber discusses how his AI platform Stanify automates social media engagement to respond to the 97% of unanswered comments on business pages.

Why Doctors Get Diagnosis Wrong — And How AI Is Fixing It | Dr. Steven Charlap, Medome

Dr. Steven Charlap discusses his AI-first primary care platform Medome built to reduce medical misdiagnosis.

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The Reality of AI Cybersecurity: Deepfakes, Zero-Days & AI Governance

Robert Wood, founder of Sidekick Security, discusses AI governance, cybersecurity challenges, and building a services firm on referrals.

Chaos Engineering to Reliability: Why the Fortune 100 Hated Our Pitch | Kolton Andrus (Gremlin)

Kolton Andrus built Gremlin by rebranding failure-testing from chaos engineering to reliability to sell to Fortune 100 executives.

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S1 E26 | His Data Found Carbon Monoxide Poisoning That Two Top Hospitals Missed | John Kelley

John Kelley discusses how his CereHealth predictive analytics platform uses AI to diagnose brain health conditions that traditional medicine misses.

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S1 E25 | He Sold Persistent Chat to Microsoft Before Slack Existed | Nick Fera

Nick Fera, CEO of enosix, discusses virtualizing SAP processes to streamline enterprise workflows through modern platforms.

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S1 E24 | The MSP Channel Is Being Robbed — And AI Is the Slingshot to Fight Back | Callen Sapien

Callen Sapien discusses building Synthreo, an AI governance platform for SMBs and MSPs.

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S1 E23 | He Lost $3M on a Failed Pivot — Here's What CloudTask Does Differently | Amir Reiter

Amir Reiter discusses building CloudTask, an AI-powered talent marketplace connecting US companies with Latin American GTM operators.

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S1 E21 | From Landing Page to $12M Series A With PayPal Ventures | Geus Walder

Geus Walder built Klearly from a gamified waitlist to a 12M Series A by focusing on hospitality payments instead of generalist soft-POS.

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S1 E20 | The Customer Success Branding Gap Most SaaS Companies Miss | Arne Hurty

Arne Hurty of BayCreative discusses building a deliberately small strategy firm serving Silicon Valley tech companies for three decades.

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S1 E22 | He Fired His Freelancers and Built a 500-Person Dev Shop to Replace Them | Furqan Aziz

Furqan Aziz founded InvoZone to connect Pakistani engineers with cash-strapped Silicon Valley startups through offshore development.

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S1 E19 | 2M Autonomous Fixes Inside PayPal | Suresh Mathew, Sedai

Suresh Mathew built an autonomous remediation system at PayPal that Sedai now uses to handle production operations without humans.

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S1 E18 | Why AI Data Centers Could Break the U.S. Power Grid | Michael Parrella

Michael Parrella discusses how AI data centers strain electricity grids and how ennrgy pivoted its product to help energy operators manage demand.

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S1 E17 | Inside the 64 Billion Identity Breach Data Lake | Andres Andreu

Constella Intelligence CEO Andres Andreu discusses his 64 billion identity breach data lake and pivot to OEM sales model.

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S1 E16 | Paying Customers Before Series A | Karen Nguyen, OFFENSAI CEO

Karen Nguyen bootstraps OFFENSAI, an autonomous cybersecurity platform validating real attack chains without inflated Series A funding.

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S1 E15 | The 272-Day B2B Sales Cycle | Nick Turner, CEO of Dreamdata

Nick Turner, CEO of Dreamdata, discusses how B2B sales cycles have stretched to 272 days and shares strategies for closing a $55M Series B.

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S1 E14 | $1.2M in 90 Days: The Claims Providers Wrote Off | Michael Riley

Michael Riley's Gabio.ai uses AI agents to recover hospital write-offs instead of chasing claim denials like competitors.

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S1 E13 | AGE: The 4th Axis the AGI Conversation Is Missing | Rana Gujral

Rana Gujral discusses Artificial General Experience as missing from AGI conversation and Behavioral Signals' deepfake audio detection technology.

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S1 E12 | 50 Customers, 1 US Patent, AI That Plays Nice | Stephen Franklin

Stephen Franklin discusses how Netwatch.AI integrates existing cybersecurity tools instead of replacing them.

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S1 E11 | Laid Off by the DoE — Then He Built an AI Startup | David Blumenthal

David Blumenthal built Eddy, an AI tool using peer-reviewed research to help teachers cut through jargon and distrust of both academia and AI.

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S1 E10 | Fighting Financial Aid Fraud With Agentic AI | Preeti Tanwar

Preeti Tanwar built AI tools to fight financial aid fraud and help college students while bootstrapping her education tech firm.

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S1 E9 | Don't Hire That Full-Time CMO Yet — Here's Why | Eyal Dror

Eyal Dror shares his 18-month fractional CMO playbook for B2B startups, emphasizing messaging over ad optimization.

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S1 E8 | Nick Mehta on Why AI Customer Success Is Failing | Inbound vs Outbound

Nick Mehta discusses creating the customer success category, scaling Gainsight to $235M, and why AI excels at inbound support but struggles with outbound CS.

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S1 E7 | The Fintech CEO Taking on Bloomberg TOMS | Ashok Mittal

Ashok Mittal, CEO of FinTech Global Center, discusses building trading systems over 30 years and competing with Bloomberg in fixed-income markets.

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S1 E6 | Your Water Plant Is Running 30-Year-Old SCADA | Patrick Miller

Patrick Miller discusses OT cybersecurity threats and building Ampyx Cyber as a lean bootstrapped firm.

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S1 E5 | The 3am LinkedIn Slip That Started Metadata.io | Gil Allouche

Gil Allouche discusses building Metadata.io from a side project into a successful revenue marketing platform using classical ML and AI agents.

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S1 E4 | The 4-Time Exited Founder Going for the Fifth | Peter Pezaris

Peter Pezaris discusses his startup experience and Vortex Software, a plugin optimizing team-invite conversion for freemium products.

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S1 E3 | Replacing the $30K Legal Marketing Agency With AI | John Fly

John Fly discusses how FirmPilot uses AI to automate law firm marketing at a fraction of traditional agency costs.

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S1 E2 | Why Every AI Agent Needs a Kill Switch | Rohan Pinto

Rohan Pinto discusses 1Kosmos' evolution from identity management to biometric authentication and AI agent security.

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S1 E1 | From Coca-Cola & Unilever to AI Startup at 60 | Stan Sthanunathan

Stan Sthanunathan left his 30-year career at Unilever and Coca-Cola to launch his AI startup i-Genie.ai.

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