We Built It Because We Had To - Tech Founder Backstories

Jonathan W. Buckley of The Artesian Network

We Built It Because We Had To is a founder-interview podcast from The Artesian Network, hosted by Jonathan Buckley. Each episode digs into the real founder journey behind B2B SaaS and tech startups — the backstories, the drama, the lessons, go-to-market, product-market fit, fundraising, enterprise sales, scaling, and how agentic AI is reshaping the bet.

  1. 3h ago

    The AI Worker With Her Own LinkedIn Page (Daniele Bernardi)

    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 Toolhouse's entire go-to-market. The big AI labs want six figures of annual spend before a business gets real support, which leaves small and mid-market companies rebuilding everything themselves and quietly giving up on AI when the bill arrives. Toolhouse fills that gap by building narrow, single-purpose "AI workers" instead of generalist agents, so they do not drift and do not need a growing pile of context to stay useful. Daniele walks through the two-person wine club in San Diego that fired its marketing agency and now runs its whole weekly campaign through one worker, how Toolhouse earns access to systems like Gmail and Salesforce by sandboxing every decision before it touches a live account, and what it took to automate a European Central Bank stress test where the output has to match human work exactly across fifty consecutive runs. Watch the full episode on YouTube: https://www.youtube.com/watch?v=1Ye-s3Fe73Q CHAPTERS 01:12 What Toolhouse actually does: turning one-off chats into repeatable AI workers02:02 Where the 90 percent cost saving comes from04:15 Why they are called workers, not agents06:16 Compliance and guardrails, from GDPR basics to enterprise policy07:40 From engineer to solutions engineer at Meta09:54 How Meta segments advertisers, and the gap that taught him everything12:27 Why the big AI labs cannot afford to serve you14:22 Finished work, not drafts, not notifications17:29 The San Diego wine club that fired its marketing agency20:41 When founders want AI to cut payroll instead of raise output24:26 Drift, and why you still need someone who knows good output from bad26:20 Flipping the paradigm: evals first, technology second29:09 Hiring engineering in India to serve a market the big labs skip31:27 The executive assistant that improvised its own personality32:39 Meet Sol, the AI worker with her own LinkedIn page35:12 Earning access to Gmail and Salesforce through sandboxing37:40 Automating the European Central Bank stress test39:46 Where the AI tooling market consolidates in three years42:04 The case for a European sovereign AI stack47:10 Close ABOUT THE GUEST Daniele Bernardi is the founder of Toolhouse, a platform that converts AI chat prompting into reusable, specialized AI workers that run over email, Slack, Teams, WhatsApp, and phone. He was previously a solutions engineer at Meta, where he worked with advertisers including Amazon and American Express, and later at Twitter. Connect with Daniele: https://www.linkedin.com/in/iamdaniele/Toolhouse: https://toolhouse.ai ABOUT THE SHOW We Built It Because We Had To is hosted by Jonathan W. Buckley of The Artesian Network, where he has helped more than 60 early stage technology companies launch and scale. Subscribe on YouTube, Spotify, Apple Podcasts, or wherever you listen. For more on scaling an early stage technology company, visit https://www.artesiannetwork.com/?utm_source=podcast&utm_medium=referral&utm_campaign=ep30&utm_content=shownotes

    The AI Worker With Her Own LinkedIn Page (Daniele Bernardi)
  2. Aug 6

    He Lost His Brother To A Misdiagnosis. Then He Built Medome (Dr. Steven Charlap)

    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 life. That loss, followed by a second misdiagnosis that took his wife's best friend and a third that nearly took his own life, sent him back to school for five and a half years at Stanford and Harvard to understand why doctors get it wrong so often. Misdiagnosis kills roughly 400,000 people a year in the US and permanently disables another 400,000, and the Institute of Medicine predicts nearly everyone will experience one in their lifetime. Steven explains why Medome approaches diagnosis by elimination rather than pattern matching, how it's built on Google's MedGemma model fine-tuned with over 100 million proprietary data points, and the surprisingly tricky engineering problem of stripping personal health information before anything touches a language model, including diseases that are literally named after people. He also shares the hardest lesson from selling into medical institutions first: doctors told him directly that extra patient information was unwelcome because they aren't paid to process it and could be held liable for missing something in it. We close on why he ignored classic startup advice to niche down, why he put his own phone number on Medome's website, and what he'd tell any founder about selling into an industry that actively resists changing how it works. Watch the full episode on YouTube: https://www.youtube.com/watch?v=5wdcYHpPOoY About the guest:Dr. Steven Charlap, MD, MBA is a serial medical entrepreneur — NYU-trained physician, Harvard MBA, and Stanford Distinguished Careers Institute fellow — and the founder of Medome. Connect with Dr. Steven Charlap:https://www.linkedin.com/in/steven-charlap-md-mba-8911906/ Learn more about Medome:https://medome.ai Subscribe to We Built It Because We Had To wherever you listen, and learn more about how The Artesian Network helps early-stage tech companies get to market and scale at https://www.artesiannetwork.com/?utm_source=podcast&utm_medium=referral&utm_campaign=ep29&utm_content=shownotes

    He Lost His Brother To A Misdiagnosis. Then He Built Medome (Dr. Steven Charlap)
  3. Jul 30

    From Government CISO to AI-Native Security Founder (Robert Wood)

    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 several tech companies before becoming the enterprise CISO at the Centers for Medicare and Medicaid Services, leading a team of nearly 500 across five divisions. That job exposed the problem that eventually pushed him to found Sidekick: specialist security teams that all report to the same leader still can't speak the same language, so he built an internal Snowflake-based "security data lake" to force the data together. They talk about why AI governance has become Sidekick's fastest-growing line of work as boards push AI adoption faster than security teams can keep up, how deepfakes and voice cloning are making old-school phishing dramatically more effective, and zerodayclock.com, the site Robert points to that tracks how the time between a vulnerability being discovered and weaponized has shrunk from years to minutes. Robert also breaks down why Sidekick made a hard pivot away from generic federal cyber contracting, how they built the business almost entirely on trust-based referrals instead of a sales team, and VSEC, their virtual CISO offering that blends senior human judgment with AI tooling they originally built just for themselves. He closes with advice for founders three months into building a services firm: don't rush to extract yourself from the work, and be ready to sit in the uncomfortable middle for longer than social media tells you to. Connect with Robert Wood: https://www.linkedin.com/in/holycyberbatman/Zero Day Clock (mentioned in the episode): https://zerodayclock.com Enjoying the show? Follow We Built It Because We Had To wherever you listen and leave a rating — it helps other founders find these stories. For more on how The Artesian Network helps early-stage tech companies get to market and scale, visit https://www.artesiannetwork.com/?utm_source=podcast&utm_medium=referral&utm_campaign=ep28&utm_content=shownotes

    From Government CISO to AI-Native Security Founder (Robert Wood)
  4. Jul 23

    Selling "Chaos" to the Fortune 100 Almost Killed His Company (Kolton Andrus)

    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 Gremlin — the company that carried chaos engineering out of Amazon and Netflix and into the Fortune 100, then repositioned it as reliability engineering to win the enterprise. Kolton shares how a brand-new Gremlin landed Twilio and Expedia as its first customers, what a six-to-nine-month MSA negotiation taught him about enterprise sales, and why the COVID quarters were among the hardest of his life — a stretch in which he hired an outside CEO, rebuilt the product around standardization and reliability scores, and later stepped back into the CEO seat himself. He breaks down the real math behind the nines of uptime (and why five nines means things simply cannot fail), explains why reliability is a change-management and accountability problem more than a software problem, and tells the story of the customer Gremlin lost to an outage and won back. The conversation closes with his take on agentic AI: "10x the code means 10x the problems" — and why reliability guardrails matter more now than ever. About the guest: Kolton Andrus is the founder, chairman, and CEO of Gremlin, backed by Amplify Partners, Index Ventures, and Redpoint. Before founding Gremlin in 2016, he built failure-injection systems at Amazon and Netflix, where his team helped take Netflix from three nines to four nines of uptime. Connect with Kolton Andrus: https://www.linkedin.com/in/kolton-andrus-77315a2/Learn more about Gremlin: https://www.gremlin.com Enjoying the show? Follow We Built It Because We Had To wherever you listen and leave a rating — it helps other founders find these stories. For more on how The Artesian Network helps early-stage tech companies get to market and scale, visit https://www.artesiannetwork.com/?utm_source=podcast&utm_medium=referral&utm_campaign=ep27&utm_content=shownotes

    Selling "Chaos" to the Fortune 100 Almost Killed His Company (Kolton Andrus)
  5. Jul 16

    His Data Found Carbon Monoxide Poisoning That Two Top Hospitals Missed (John Kelley)

    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 organization. John explains why a Vietnam-era draftee watching friends come home with Agent Orange exposure, PTSD, and misdiagnoses decided in 2009 that the same data informatics Google and Amazon used to predict purchases could predict what was actually wrong inside a person's brain. He walks through the "patients like me" cohort model built on roughly 4,800 referred patients, why traumatic brain injury became the company's specialty, and how carbon monoxide binds to the iron in the basal ganglia and starves it of dopamine - the mechanism two of America's best hospitals missed. The harder story is the go-to-market one. Pharma, insurance, and health systems - the three constituencies John assumed would embrace better diagnostics - all resisted, for rational reasons he lays out plainly. The VA, which should have been the natural ally, never engaged. Osteopathic physicians became the earliest adopters over MDs because they were trained to look at the whole system rather than the symptom. The company cleared the FDA in 120 days under the 21st Century Cures Act, immediately in Theranos's wake, got in front of four national carriers and Medicare, and then COVID arrived in March 2020 and took the momentum with it. Today the business has pivoted away from clinical services entirely, licensing its analytics engine as $2-4M enterprise contracts. John closes with the part most guests won't say out loud: after seven acquisitions across ten boards, he's not sure he was the right investor for this one - because he underestimated the resistance, and that's a due-diligence lesson, not a bad-luck story. Chapters00:00 The show, and how Jonathan and John met at McData01:56 Data informatics, Agent Orange, and the 2009 thesis03:24 "Patients like me" - the core idea04:32 Brought in as investor and chair, and the loss that changed the role06:58 4,800 patients, cohorts, and why TBI became the specialty08:46 Why pharma, insurance, and health systems all resisted11:10 The VA that should have been an ally12:33 Who said yes first: the non-siloed clinicians16:03 Why DOs became early adopters over MDs19:14 A Mission Viejo teenager, Cedars-Sinai, and Mayo21:45 Carbon monoxide, the basal ganglia, and a furnace flue24:18 Cash-pay reality, pro bono work, and suicide ideation26:13 FDA clearance in 120 days, right after Theranos28:12 Four carriers, Medicare, then COVID30:59 The pivot to iLLUME Ai and $2-4M licensing contracts33:18 Micro-targeting DOs and riding thought-leader credibility36:39 What he'd tell you about investing outside your specialty Guest: John Kelley, Chairman, CereHealth Corp. Previously CEO and Chairman of McData Corp, a NASDAQ 100 company. He has served on ten public and private-equity/venture-backed boards, seven of which reached acquisition. Watch the full episode on YouTube: https://www.youtube.com/watch?v=EnElZDxyGow Connect with John Kelley: https://www.linkedin.com/in/johnkelley3/CereHealth: https://www.linkedin.com/company/cerehealthiLLUME Ai: https://illumeai.com Subscribe on YouTube, Spotify, or Apple Podcasts for new conversations with early-stage tech founders and CEOs. See how The Artesian Network helps founders get established and reach scale: https://www.artesiannetwork.com/?utm_source=podcast&utm_medium=referral&utm_campaign=ep26&utm_content=shownotes

    His Data Found Carbon Monoxide Poisoning That Two Top Hospitals Missed (John Kelley)
  6. Jul 9

    He Sold Persistent Chat to Microsoft Before Slack Existed (Nick Fera)

    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 configuration, pricing, and order creation, and makes them usable inside modern front ends like Salesforce and Microsoft Copilot. Nick explains how his team compressed a 10-hour customer quoting process down to 10 minutes, why enosix sells to the business side instead of IT, and how emotional storytelling, not feature lists, wins enterprise deals. He also gets candid about surviving a CFO who killed a deal at the last minute while Nick was on a bass fishing boat, and the one hard lesson about selling a product you don't use yourself. If you build, buy, or sell enterprise software, this conversation reframes how you think about integration, value, and the buyer who won't admit they have a problem. Guest: Nick Fera, CEO of enosixConnect with Nick: https://www.linkedin.com/in/nickfera/Learn more about enosix: https://enosix.com Watch on YouTube: https://www.youtube.com/watch?v=QZlKiCR9AwA Subscribe for new conversations with early-stage tech founders, and see how The Artesian Network helps founders scale: https://www.artesiannetwork.com/?utm_source=podcast&utm_medium=referral&utm_campaign=ep25&utm_content=shownotes

    He Sold Persistent Chat to Microsoft Before Slack Existed (Nick Fera)

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We Built It Because We Had To is a founder-interview podcast from The Artesian Network, hosted by Jonathan Buckley. Each episode digs into the real founder journey behind B2B SaaS and tech startups — the backstories, the drama, the lessons, go-to-market, product-market fit, fundraising, enterprise sales, scaling, and how agentic AI is reshaping the bet.