Codeandcobblestones - Podcast Details

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Code and Cobblestones AI Is Making Cybercrime Cheap and Easy | Dave Gerry (Bugcrowd) & Antonio Bovoso (Consiro)A few years ago, launching a serious cyberattack took years of experience. Now it takes bad intentions and a prepackaged AI tool from a criminal forum. Finding vulnerabilities is the easy part, and AI can write working exploits in record time. The next target could be the AI agent reading your email instead of you. So how do defenders keep up when they’ve always been outgunned, and now they’re getting outgunned faster? That’s what this episode is about. In episode 15 of Code and Cobblestones, Dave Gerry, CEO of Bugcrowd, and Antonio Bovoso, founder...

2026-10-2651 min

Code and Cobblestones How a 4x CRO Builds Sales Teams That Scale in the AI Era | Jason Forget, Resolve.ai, Ep. 14 Engineers spend about 70% of their time on production issues instead of writing code. Sales teams have a similar problem: reps dig through Salesforce, leaders run pipeline reviews nobody enjoys, and the process falls apart as soon as the company starts growing fast. AI is changing both. So what does a revenue playbook look like when half of it didn't exist a year ago? That's what this episode is about. In episode 14 of Code and Cobblestones, Jason Forget, President and CRO of Resolve.ai, joins us, Matt Crane and Will Lehmann, to talk about scaling s...

2026-10-1942 min

Code and Cobblestones Building a Cybersecurity Startup in the Age of AI | Richard Li, PolarSky, Ep. 13Companies want to plug Claude and ChatGPT into everything they own. SharePoint, Google Drive, years of internal files. The problem is that most of that data is over-permissioned, and the people in charge of security know it. Meanwhile, the headlines say AI agents are going rogue and trying to hack their way into systems. So how worried should companies actually be, and what can they control? That's what this episode is about. In episode 13 of Code and Cobblestones, Richard Li, founder and CEO of PolarSky, joins us, (Matt Crane and Will Lehmann) to talk about b...

2026-10-1337 min

Code and Cobblestones Vardera, the Boston Startup Grading Collectibles With AI | Derek Bugley, Vardera, Ep. 12Every day, thousands of trading cards, coins and sneakers get listed online by people guessing what they're worth. Some are mislabeled and some are fake. The experts who could tell the difference are backed up by millions of cards, and grading one can take nine months and $50. So why can't the biggest AI models fix this? That's what this episode is about. In episode 12 of Code and Cobblestones, Derek Bugley, CEO of Vardera, joins us, Matt Crane and Will Lehmann, to talk about building what he calls the intelligence layer for collectible commerce. Vardera only...

2026-10-0549 min

Code and Cobblestones Why Onboarding Decides Renewals and How AI Agents Are Scaling It | Paul Holder, OnRamp, Ep. 11Most companies think they lose customers at renewal. They actually lose them long before that, during onboarding. So why do so many still run it on spreadsheets and email threads? And what changes when AI agents start doing the work? That's what this episode is about. In episode 11 of Code and Cobblestones, Paul Holder, co-founder and CEO of OnRamp, joins us, Matt Crane and Will Lehmann, to talk about the part of the customer journey he calls the most important one. By his count, 90% of the time onboarding is the reason a customer renews or w...

2026-09-2845 min

Code and Cobblestones What It Takes to Get Funded at Inception Stage | Ellen Chisa, Boldstart Ventures, Ep. 10Most founders think a killer pitch deck is what gets them funded. It isn't. The best early-stage investors are writing checks before there's a product, before there's revenue, sometimes before there's even a company name. So what actually convinces them? That's what this episode is about. In episode 10 of Code and Cobblestones, Ellen Chisa joins us, Matt Crane and Will Lehmann, to walk through what it takes to get funded at the earliest stage there is: inception. She's a partner at Boldstart Ventures, where they only write checks before a product exists, and she's been...

2026-09-2133 min

Code and Cobblestones How AI Is Changing Cybersecurity | Lior Div, 7AIHackers already have AI. So do the people trying to stop them. Who wins that race? And how fast is it actually moving? That's what this episode is about. In episode 9 of Code and Cobblestones, Lior joins us, Matt Crane and Will Lehmann, to walk through what it looks like to build the defender side of an arms race most people don't know is already happening. Hackers already have AI writing and running their attacks. Almost nobody has AI running the defense with the same speed. He didn't come at this fr...

2026-09-0840 min

Code and Cobblestones The Half of Manufacturing Physical AI Ignores | Annie Lu, LaminarEvery self-driving car has cameras or a lidar system. It knows what's around it before it decides where to go. Now picture a factory built the same way, except nobody ever built the camera or the lidar. That's process manufacturing today: the reactors, pipes, and stainless steel equipment behind your protein bar, your prescription, the chips in your laptop. Half of everything the world manufactures runs through equipment like this, and almost nobody measures what's actually happening inside it in real time. That's the gap Annie Lu and her brother David set out to close w...

2026-08-3043 min

Code and Cobblestones Building AI Tools for the 90% of Businesses Tech Forgot | Shannon Kay, Topline ProShannon Kay studied industrial engineering at Clemson, spent a summer taste-testing soup at Campbell's, cut her teeth at Deloitte, ran supply chain analytics at Wayfair, and left Harvard Business School with an "incomplete" on her LinkedIn to chase an idea that wasn't even the right idea yet. She co-founded Topline Pro anyway, and now runs it as COO. In episode 7 of Code and Cobblestones, Shannon joins hosts Matt Crane and Will Lehmann to talk about what it takes to build AI for the 90% of small businesses that don't have a tech team, don't sit at...

2026-08-1840 min

Code and Cobblestones Agent Abundance: Jack O'Brien on AI's Real Bottleneck | Ep. 6Subconscious co-founder and CEO Jack O'Brien makes the case that the ceiling on AI isn't capability, it's cost, and that the next wave belongs to agents that run for hours, not chatbots that answer in seconds. Matt Crane (MGMT Boston) and Will Lehmann (Step Function) get into open weights, edge inference, and why Jack is betting on Boston to build it. What you'll learn Why cost, not capability, is the real ceiling on AI agents What "agent abundance" means and why teams get hooked once they have it How Subconscious compresses agent context on the GPU (one cu...

2026-08-0946 min

Code and Cobblestones How AI Agents Are Transforming Engineering Teams | Ep. 5 with Jellyfish CEO Andrew LauAndrew Lau grew up in the Bay Area, cut his teeth as an engineer at IBM and Microsoft, spent a decade at Endeca helping it grow from 7 people to 550 before Oracle bought it for over a billion dollars, and later ran strategy at Nanigans. He built Jellyfish in Boston anyway. In episode 5 of Code and Cobblestones, Andrew joins hosts Matt Crane and Will Lehmann to talk about what happens when half your pull requests get opened and closed by an AI agent, and why he thinks the software development lifecycle as we knew it is already gone.

2026-07-3048 min

Code and Cobblestones Inside Nebulock's $25M Series A | Ep. 4 with Damien LewkeDamien Lewke could build his company anywhere. He grew up in the Bay Area, threat-hunted on a nuclear weapon system at Northrop Grumman, helped define the EDR category at early CrowdStrike, closed nine-figure deals at Palo Alto Networks, and did his graduate research at MIT's CSAIL. He chose Boston. In episode 4 of Code and Cobblestones, Damien joins hosts Matt Crane and Will Lehmann to talk about founding Nebulock, a hunt-first security operations platform that just closed a $25 million Series A led by FirstMark, and why the next generation of cybersecurity gets built here. The conversation r...

2026-07-2338 min

Code and Cobblestones Why Boston Is Where You Build Hard Things | Ellen RubinEllen Rubin has founded three companies, taken Netezza through its IPO, and sold startups to both Verizon and AWS. Now an operating partner at Glasswing Ventures, she sits down with Matt Crane and Will Lehmann to talk about why the hard, unglamorous parts of the stack are the ones worth building, and why Boston is the place to build them. From a citywide push to teach every high school student AI, to what a soccer crowd taught her about B2B sales, this one runs from the classroom to the cap table. What you'll learn Why...

2026-07-1643 min

Code and Cobblestones What a Startup Will Actually Look Like in 12 Months | Building in the AI Era in BostonMatt Crane (MGMT Boston) and Will Lehmann (Step Function) break down what company building looks like in the next twelve months, why the government pulling Fable was a turning point for AI strategy, and what Boston's fastest-growing tech companies are actually doing differently. What you'll learn: Why "optionality" is now the most important word in your AI stack, and what the Fable shutdown taught enterprise leaders What a startup org chart looks like 12 months out, and why design now comes in at hire one through ten Why the best AI companies (Blitzy, Suno) almost never started...

2026-07-0834 min

Code and Cobblestones The $1.4B Code Company and the AI Music Lab Hiding in BostonMatt Crane (⁠MGMT Boston⁠) and Will Lehmann (⁠Step Function⁠) launch Code and Cobblestones, a show about what's being built in Boston tech right now, told by the people building it. In episode one they break down Boston Tech Week, how AI is changing the way companies get built, where venture dollars are moving, and whether Boston is underrated, properly rated, or overrated as a startup city. What you'll learn: Why Boston sits at number three in US venture and what that "medal" actually means The "tokens vs. talent" tension ever...

2026-06-3037 min