We Built It Because We Had To - Tech Founder Backstories

Ashok Rajan ran 75 demos in two months and closed nothing. Then he took every recording, fed it to AI, and rebuilt his company around what customers actually said. In this episode of We Built It Because We Had To, host Jonathan Buckley is joined by Ashok Rajan, founder of Pristine Data AI, an AI sales intelligence and outbound platform that handles prospect search, enrichment, research, playbooks,...

Every major AI training operation is quietly running into the same wall: the speed at which silicon can move data between chips. Every new GPU cluster a hyperscaler adds makes the problem more expensive. In this episode of We Built It Because We Had To, host Jonathan W. Buckley is joined by Vivek Raghunathan of Xscape Photonics — the deep-tech company spun out of Columbia University research to at...

In this episode of We Built It Because We Had To, host Jonathan W. Buckley is joined by Daniel Rosenrauch of Viirtue, a white-label VoIP and unified communications platform built for MSPs, ISPs, and resellers who want to sell voice services under their own brand without running the infrastructure themselves. Viirtue was founded by people who had been resellers themselves, and it positions itself a...

Enterprise legal teams are overwhelmed by inbound work they can't see or control — and it slows down the whole business. Most AI companies chase sales and customer support. Evan Wong went after the function they all ignore. In this episode of We Built It Because We Had To, host Jonathan W. Buckley is joined by Evan Wong, founder of Checkbox — the AI Legal Front Door and Operating System built for...

Gerald Zankl and his co-founders spent three years selling sales playbooks. The playbooks were good. Almost nobody bought them. So they built a recorder to prove to sales reps that they needed the playbooks, and the customers told them to keep the recorder and throw the playbooks away. In this episode of We Built It Because We Had To, host Jonathan W. Buckley is joined by Gerald Zankl, founder of...

The application security industry spent years believing its tools found roughly 95 percent of the defects in code. Chris Near studied 34 million findings across 57 tools and put the real number closer to 15 or 20 percent. In this episode of We Built It Because We Had To, host Jonathan W. Buckley is joined by Chris Near, founder of CyberSagacity, the company he built to sit on top of application se...

Stephanie Taylor's diagnosis of her own industry is blunt. With the rise of SaaS, consulting got diluted by product specialists. Companies thought they were hiring consultants to implement new technology, and what they really hired were order takers. In this episode of We Built It Because We Had To, host Jonathan W. Buckley is joined by Stephanie Taylor, CEO and founder of VFP Consulting, the firm...

Most companies still treat returns as a cost center — and Ricardo Morgado makes the case that this framing is itself the problem. In this episode of We Built It Because We Had To, host Jonathan W. Buckley is joined by Ricardo Morgado of Getloopos, the company building LoopOS — an operations layer for circular commerce inside enterprise retail. They get into what Ricardo actually saw inside enterpr...

One of Toolhouse's AI workers named itself, chose its own pronouns, and now runs a LinkedIn page its founder does not control. That was not in the prompt. Daniele Bernardi spent his early career as an engineer at Meta and later at Twitter, where he picked up the definition of trust he still runs the company on: consistency over time. In this episode he explains how that single idea shaped Toolhous...

When a brand's comment section blows up, someone has to answer — at a scale no social team can staff. In this episode of We Built It Because We Had To, host Jonathan W. Buckley sits down with Hank Leber, co-founder of Stanify, the company building AI that answers a brand's social comments in the brand's own voice — "listening with humanity." Hank explains why enterprise buyers hesitate before hand...

Misdiagnosis kills roughly 400,000 people a year in the US — and when Dr. Steven Charlap tried to fix it, doctors told him they'd rather not know. In this episode, Jonathan W. Buckley is joined by Dr. Steven Charlap, MD, MBA and founder of Medome, an AI-first primary care platform. Steven had already sold one company and retired when his older brother, a cardiologist, was misdiagnosed and lost his...

His hardest problem wasn't hackers — it was a 500-person security organization whose specialist teams couldn't speak the same language. In this episode of We Built It Because We Had To, host Jonathan W. Buckley sits down with Robert Wood, founder and CEO of Sidekick Security, an AI-native cybersecurity consulting firm. Robert started out doing offensive red team work, then ran security programs at...

His pitch — "let us break your systems on purpose" — thrilled engineers and terrified the Fortune 100 executives who signed the checks. So Kolton Andrus did something few founders have the nerve to do: he stopped using the very term his company was built on. In this episode of We Built It Because We Had To, host Jonathan W. Buckley sits down with Kolton Andrus, founder, chairman, and CEO of Gremli...

A teenager was diagnosed as paranoid schizophrenic by Cedars-Sinai, then again by Mayo Clinic. His furnace was poisoning him. It took John Kelley's data about 20 minutes to find it. In this episode, Jonathan W. Buckley sits down with John Kelley, Chairman of CereHealth Corp and the iLLUME Ai platform - and, twenty years ago, the CEO and Chairman of McData Corp when Jonathan worked in its marketing...

Before Slack existed, Nick Fera built and sold persistent chat to Microsoft. Today he's taking on a problem most enterprise software companies won't say out loud: the systems that run the world's biggest manufacturers are nearly impossible to reach. In this episode, Jonathan W. Buckley sits down with Nick Fera, CEO of enosix, the company that virtualizes SAP's most complex processes, product confi...

In this episode, I'm joined by Callen Sapien, CEO and Co-Founder of Synthreo. We talk about how he and his co-founders built a multi-tenant, model-agnostic AI governance and consumption platform specifically for SMBs and the managed service providers that serve them — the 48% of the global economy that every enterprise AI company walks right past. Callen shares the origin story behind Synthreo: a...

He put nearly $3 million of his own money into a SaaS pivot that failed — because he tried to sell customers the help they needed instead of the help they wanted. In this episode of We Built It Because We Had To, host Jonathan W. Buckley sits down with Amir Reiter, Founder & CEO of CloudTask, the global talent marketplace connecting US companies with GTM operators across Latin America and the...

Most founders spend year one chasing product-market fit. Furqan Aziz spent his chasing something harder to build than any product: trust. In this episode of We Built It Because We Had To, host Jonathan W. Buckley sits down with Furqan Aziz, CEO and Founder of InvoZone. As a CTO in San Francisco, Furqan was burned by unreliable freelance developers who ghosted mid-project and missed deadlines on ti...

What if going narrower is what makes you fundable? Geus Walder co-founded Klearly as a generalist soft-POS app — download an app, turn any phone into a payment terminal, no hardware required. It gained traction across taxis, retail, and more. But a year of staying close to customers kept pointing to one place: hospitality had the deepest payment pain and the worst-fitting tools. So Klearly cut eve...

Most SaaS companies spend heavily to win the deal — then go silent the moment the contract is signed. Arne Hurty has spent three decades watching that gap widen, and building a firm to help close it. In this episode, I'm joined by Arne Hurty, founder of BayCreative, a strategic branding and marketing firm that has supported Silicon Valley tech companies since 1997. Arne walks me through three deca...

What happens when cloud deployment outpaces the humans managing it? At PayPal, Suresh Mathew's team built the answer — an autonomous system that ran 2 million production remediations before he spun it out as Sedai. In this episode, I'm joined by Suresh Mathew, founder and CEO of Sedai. We talk about the problem DevOps created: developers deploying directly to production faster than any SRE team co...

AI data centers are hitting the U.S. power grid like five-gigawatt toasters — and unlike Bitcoin, that demand can never be switched off. In this episode, I sit down with Michael Parrella, CEO of ennrgy.com, about an existential moment most founders recognize but few talk about honestly: learning your largest customer is walking out the door. Michael returned as CEO of ennrgy in late 2024, and with...

Andres Andreu sits on one of the richest datasets in cybersecurity — nearly 64 billion breached identities — and for years growth still stalled. The problem was never the data. It was who Constella was selling it to. In this episode of We Built It Because We Had To, Andres Andreu, CEO of Constella Intelligence, walks through the breach-data lake his company has amassed over 16-plus years and how i...

Most companies build their front door out of glass — and the guard dog is asleep all day. That's how Karen Nguyen describes the security gap her company exists to close. In this episode, Karen — co-founder and CEO of OFFENSAI — joins Jonathan Buckley on the morning she launched v2 of her autonomous cybersecurity platform. We get into what "exploitation validation" actually means and why it's not j...

The B2B sales cycle just hit 272 days. That is not friction. That is a buying committee with a new veto holder back at the table. In this episode of We Built It Because We Had To , I sit down with Nick Turner, CEO of Dreamdata, the Copenhagen-founded B2B revenue attribution platform that closed a $55M Series B in October. Nick spent twenty years in MarTech sales before joining Dreamdata as CRO to...