Code and Cobblestones

About Code and Cobblestones

Code & Cobblestones tells the real stories behind Greater Boston's founders, funders, and builders. Each episode digs into how local startups got started, what almost killed them, and what's happening across the city's tech scene now. Code and Cobblestones is brought to you by MGMT Boston and Step Function VC, and produced by Obey Creative, a boutique branding and authority media consultancy in Boston. (https://obeycreative.com) https://obeycreative.com (https://obeycreative.com)

Publisher

codeandcobblestones

Category

business

Language

en

Explicit

No

First episode

30 Jun 2026

Latest episode

19 Oct 2026

Latest episodes

14 episodes in the feed.

1. 

   19 Oct 2026

   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 sales teams from single-digit millions to hundreds of millions. He's done it four times over 13 years, at companies like Redis and CockroachDB. Now he's at Resolve, which builds AI agents that take the pager and handle about 80% of production incidents. He didn't take the usual path. Jason started in finance at Gillette, thinking that was where the money was. Then a sales team invited him to President's Club, and he was hooked. His first board meeting as a sales leader changed how he thinks about revenue. He showed up ready to talk comp plans, and the CEO told him to talk about the customers. We got into: CJ Desai's move to Meta, AI-driven hacking, and why every buying decision comes down to making money, saving money, or staying secure "Growth is incremental, scale is exponential," and why being a mile wide and an inch deep won't get you far Sales process debt: the hidden tax companies pay for skipping the boring stuff Why clear expectations beat a "tough" culture, and why people follow him from company to company Hiring for curiosity, GTM engineering, and Deal Pulse, the AI agent that inspects his team's deals Why the best information comes on the walk to the elevator Founder-led sales vs. hiring a CRO, and the one question founders need to answer first: will you really let go? Rapid fire: "Don't expect what you don't inspect," why you still have to cold call, more harnesses than there are horses, and the Boston company he'd join tomorrow TIMESTAMPS: 00:00 Meet Jason Forget, CRO of Resolve.ai 00:57 What Is AI SRE? 02:57 Enterprise Sales and the AI Talent War 06:24 AI Cybersecurity: Real Risk or Hype? 08:17 Startup Strategy: Vision vs. Focus 11:33 From Finance at Gillette to Sales 13:15 Why Sales Became a Science 16:22 The Board Meeting That Changed His Career 19:23 Why He Joined Resolve.ai 22:11 How to Scale Sales at Every Stage 24:19 Sales Process Debt 24:47 Know Your Numbers (The Shark Tank Test) 25:41 Building Sales Culture With Clear Expectations 27:46 Leadership: Take All the Blame 29:25 AI Sales Tools and GTM Engineering 32:16 Faster Time to Value for Customers 33:23 Managing Distributed Sales Teams 36:36 Rapid Fire: Best Sales Advice 39:56 Founder-Led Sales vs. Hiring a CRO 43:24 Boston Tech Talent and Final Takeaways Guest: Jason Forget, President and CRO of Resolve.ai https://www.linkedin.com/in/jason-forget https://resolve.ai/ Hosts: Matt Crane, Founder of MGMT Boston https://mgmtboston.com/ https://www.linkedin.com/in/matthewhcrane/ Will Lehmann Founder of Step Function VC https://stepfunction.vc/ https://www.linkedin.com/in/wlehmann/ Watch/listen/Subscribe: Spotify: https://open.spotify.com/show/033HueFNlE1LPnEFPvVscs?si=e2351085b40b4334 Apple Podcasts: https://podcasts.apple.com/us/podcast/code-and-cobblestones/id6785977680 Youtube: https://www.youtube.com/@MGMTBoston Code and Cobblestones is a love letter to Boston tech founders. New episodes spotlight the people building the city's next generation of companies. ▶ Subscribe for the rest of the tour. New episodes spotlight the founders and builders putting Boston on the map. Produced in partnership with OBEY Creative, building podcast-driven content engines for B2B founders. One great conversation per week becomes 15-20 assets: clips, LinkedIn posts, blog content, and newsletter material. Learn more at https://obeycreative.com/

2. 

   13 Oct 2026

   Building a Cybersecurity Startup in the Age of AI | Richard Li, PolarSky, Ep. 13

   Companies 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 building an autonomous agent that protects company data in the age of AI. His one-liner is simple: "We're a data protection agent." This isn't Richard's first rodeo. He went from MIT to ArsDigita, Red Hat, Rapid7 and Duo Security (bought by Cisco), then founded Ambassador, a Kubernetes company he sold last year. When ChatGPT showed up, he didn't know what a transformer was. So he learned, built his own RAG app, and kept going until he knew he wanted to start an AI company. A conversation with former CTO Glenn Chisholm about data authorization became the idea, and about 15 CISO conversations later, it became PolarSky. We got into: Why Richard thinks AI agents aren't really "going rogue," and what's actually happening when they break through barriers Frontier models vs. open weight models, and why China's limited compute is pushing everyone toward efficiency Why AI still struggles with creativity and vision (and why that keeps humans in charge) How he knew the idea was ready: when he stopped changing the story after every CISO call Lessons from Ambassador, including waiting too long to build a sales process Why engineers are now managers of agents, and why the bottleneck is communication, not code Hiring a product manager early, something he didn't do at Ambassador until he had 50 engineers Selling to enterprise CISOs with no PLG shortcut (and more steak dinners in one year than in 10 at Ambassador) How to vet investors: talk to the founders they didn't introduce you to, especially the ones who failed An AI team in California, cloud engineering in Montreal and go-to-market in Boston Rapid fire: his favorite models, why the OpenAI breach hype is overrated, and getting mistaken for a Tinder date in a New York café TIMESTAMPS:00:00 Meet Richard Li, PolarSky Founder 00:45 Are AI Agents Going Rogue? 02:52 AI Regulation and Cybersecurity 04:01 AI Model Costs vs. Open Weight Models 05:56 What Cheaper AI Means for Enterprises 08:41 From MIT to Startup Founder 11:53 How PolarSky Started 15:03 Validating a Startup Idea with CISOs 16:30 What Is a Data Protection Agent? 17:03 First-Time Founder Lessons 20:00 Engineers Managing AI Agents 22:08 Finding a Real Customer Pain Point 23:52 Enterprise Sales for Cybersecurity 26:09 How to Choose Startup Investors 28:24 Building a Startup in Boston 32:01 Rapid Fire 37:44 Advice for Founders Guest: Richard Li, Founder and CEO of PolarSky, https://www.linkedin.com/in/richardli https://polarsky.ai/ Hosts: Matt Crane, Founder of MGMT Boston https://mgmtboston.com/ https://www.linkedin.com/in/matthewhcrane/ Will Lehmann Founder of Step Function VC https://stepfunction.vc/ https://www.linkedin.com/in/wlehmann/ Watch/listen/Subscribe: Spotify: https://open.spotify.com/show/033HueFNlE1LPnEFPvVscs?si=e2351085b40b4334 Apple Podcasts: https://podcasts.apple.com/us/podcast/code-and-cobblestones/id6785977680 Youtube: https://www.youtube.com/@MGMTBoston Code and Cobblestones is a love letter to Boston tech founders. New episodes spotlight the people building the city's next generation of companies. ▶ Subscribe for the rest of the tour. New episodes spotlight the founders and builders putting Boston on the map. Produced in partnership with OBEY Creative, building podcast-driven content engines for B2B founders. One great conversation per week becomes 15-20 assets: clips, LinkedIn posts, blog content, and newslett

3. 

   5 Oct 2026

   Vardera, the Boston Startup Grading Collectibles With AI | Derek Bugley, Vardera, Ep. 12

   Every 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 needs the front and back of a card. From that it can identify the card, grade it, price it and flag whether it's fake, all in about 300 milliseconds. The idea started at home. Derek and his co-founders, Michael and Ben, lost family members around the same time and ended up handling estates full of collectibles. (His dad collected sports memorabilia.) They watched appraisers walk through, take photos and get the values wildly wrong. Then they started talking to the biggest marketplaces in the world. What looked like a personal problem turned out to be a multi-billion-dollar one. We got into: Why Vardera tested frontier models first, spent a lot of money on mixed results, and now builds everything from scratch The last-mile problem: delivering 99.5% accuracy and getting asked for more Why half the business is data labeling, and why "the data sucks" at companies that claim to have the best data Skipping the consumer app ("the startup graveyard") to sell to marketplaces, plus an open API built for AI agents A blind head-to-head against human graders, where Vardera scored in the high 90s and caught cards that had already been slabbed with the wrong grade Grading backlogs of 20 to 30 million cards, and why nobody's training to be a numismatist anymore Live commerce, Whatnot, and a fisherman in Seattle selling same-day salmon on a livestream Collectibles as an asset class, and why Derek wants Vardera to be the Stripe of this market Why the next generation of heirs will sell the art and buy cards, sneakers and sealed Nintendo games Rapid fire: an $80 Castle Grayskull vs. one that sold for $240K, NFTs "valuable or BS?" (his answer: "Yes"), and why Boston doesn't need an 11th steakhouse in the Seaport Mentioned in this episode: Vardera's breakdown of how its grading model compares to frontier AI models: https://www.vardera.com/blog/we-built-the-best-trading-card-identification-and-grading-model-in-the-world.-here-are-the-numbers TIMESTAMPS: 00:00 Meet Vardera CEO Derek Bugley 00:31 AI for Collectible Authentication 01:35 OpenAI Buys Glass Imaging 04:43 Meta Glasses and Computer Vision 06:56 Collectibles API for AI Agents 10:03 Custom AI vs Frontier Models 14:05 Vardera's Founding Story 16:16 Card Grading Backlogs at Scale 19:03 Choosing Collectible Categories 24:09 AI Grading vs Human Graders 26:21 Fraud in the Collectibles Market 27:04 Working With Auction Houses 28:21 Why Human Experts Don't Scale 31:23 How Vardera's AI Works 34:23 Live Commerce and Whatnot 37:31 The Stripe of Collectibles 41:34 Building a Boston AI Startup 43:35 Rapid Fire 49:25 Advice for Founders Guest: Derek Bugley, Co-Founder and CEO of Vardera https://www.linkedin.com/in/derekbugley/ https://www.vardera.com/ Hosts: Matt Crane, Founder of MGMT Boston https://mgmtboston.com/ https://www.linkedin.com/in/matthewhcrane/ Will Lehmann Founder of Step Function VC https://stepfunction.vc/ https://www.linkedin.com/in/wlehmann/ Watch/listen/Subscribe: Spotify: https://open.spotify.com/show/033HueFNlE1LPnEFPvVscs?si=e2351085b40b4334 Apple Podcasts: https://podcasts.apple.com/us/podcast/code-and-cobblestones/id6785977680 Youtube: https://www.youtube.com/@MGMTBoston Code and Cobblestones is a love letter to Boston tech founders. New episodes spotlight the people building the city's next generation of companies. ▶ Subscribe for the rest of the tour. New episodes spotlight the founders

4. 

   28 Sept 2026

   Why Onboarding Decides Renewals and How AI Agents Are Scaling It | Paul Holder, OnRamp, Ep. 11

   Most 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 walks. He learned that the hard way. Leading onboarding at VTS, back when the answer to scale was just hiring more people. Running post-sales at Troops and seeing the same frustrated customers. Then a question for his co-founder, Ross: are we just bad at our jobs, or is everyone feeling this? Turns out everyone was. They started OnRamp in the middle of COVID, fully remote, and missed the 2021 valuation frenzy entirely. He's grateful for that now. We got into: Why Paul thinks autonomous AI agents can finally take real action in B2B, and why that answer wasn't true six months ago PLG vs. enterprise onboarding, and what happened when Slack tried to roll out to IBM (he had a word for it we can't print here) "Making progress between the calls," and why most onboardings stall waiting for the next meeting Rebuilding a SaaS company as AI native without throwing out the foundation. No AI for the sake of AI. New pricing coming soon (breaking news, live on the show), and the catch-22 of charging for every AI action Why Onramp stopped selling to 30-person startups, and how cutting onboarding drop-off by 10% turns into a $3M problem for one customer Raising $27M with a 20, 30, 40-year view, and why a sexy headline valuation was never the goal His advice after a Series A: don't hire ahead of growth. Wait until the team is bursting at the seams. Two CEO careers, two young kids, and a paper calendar in the kitchen that beats most of the tech TIMESTAMPS:00:00 Intro: Paul Holder, OnRamp CEO 00:41 AI Personal Assistants: Hype Check 01:34 AI Adoption in B2B 02:47 Autonomous AI Agents in B2B 04:28 Dreamforce and AI Interfaces 06:58 PLG vs Enterprise Onboarding 09:45 When AI Agents Onboard AI Agents 10:49 Onboarding Beyond Spreadsheets 11:39 Onramp Origin Story 15:51 From SaaS to AI Native 19:00 How to Price AI Features 20:49 Finding Your ICP 23:57 Who Onramp Is Built For 24:46 Should AI Companies Sell Services? 25:12 From Product to Platform 27:19 Customer Obsession Culture 29:26 High Standards, No Gimmicks 31:02 Fundraising and Cap Table Strategy 33:35 Founder Lesson: Trust Your Gut 34:58 Balancing Family and CEO Life 37:04 How a CEO Spends the Week 38:22 Rapid Fire: Mentors and Series A Hiring 42:49 Tools for Busy Founder Parents 45:23 Why Now Is the Time to Build Guest: Paul Holder, Co-founder & CEO of OnRamp https://www.linkedin.com/in/paulcholder/ https://onramp.us/ Hosts: Matt Crane, Founder of MGMT Boston https://mgmtboston.com/ https://www.linkedin.com/in/matthewhcrane/ Will Lehmann Founder of Step Function VC https://stepfunction.vc/ https://www.linkedin.com/in/wlehmann/ Watch/listen/Subscribe: Spotify: https://open.spotify.com/show/033HueFNlE1LPnEFPvVscs?si=e2351085b40b4334 Apple Podcasts: https://podcasts.apple.com/us/podcast/code-and-cobblestones/id6785977680 Youtube: https://www.youtube.com/@MGMTBoston Code and Cobblestones is a love letter to Boston tech founders. New episodes spotlight the people building the city's next generation of companies. ▶ Subscribe for the rest of the tour. New episodes spotlight the founders and builders putting Boston on the map. Produced in partnership with OBEY Creative, building podcast-driven content engines for B2B founders. One great conversation per week becomes 15-20 assets: clips, LinkedIn posts, blog content, and newsletter material. Learn more at https://obeycreative.com/

5. 

   21 Sept 2026

   What It Takes to Get Funded at Inception Stage | Ellen Chisa, Boldstart Ventures, Ep. 10

   Most 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 doing it for six years. She didn't take a straight line to venture capital. She dropped out of college for a year to start a company with five friends. She built the first versions of Office Mobile at Microsoft, then worked at Kickstarter and at Lola. After that she co-founded Dark, a programming language company, with Paul Biggar, who started CircleCI before that. Dark didn't end the way either of them planned. She walked away, and Boldstart brought her in instead. What we talked about: Why Ellen doesn't need a pitch deck, and what she actually asks for instead: a ten-year vision you can defend, and a plan for next week The "AB flip-flop," the pattern she watches kill startups: go end-user first, flip to enterprise, flip back, never actually commit to a lane Why she thinks every founder has a hard ceiling of 50, maybe 70, good years in them, and what that means for knowing when to walk away from something that isn't working Anthropic's new 25,000-square-foot office in Kendall Square, and why she thinks the real draw isn't PR, it's the talent pool at MIT and Harvard Bending Spoons buying Miro, and what she says it actually reveals about which startups have the growth to back up their old valuations, and which don't Why she thinks embodied AI is still underrated next to software agents, twelve months out (her prediction, not ours) TIMESTAMPS:00:00 Ellen Chisa Joins the Show 01:07 AI Safety Debate and P(doom) 05:02 Anthropic Opens a Boston Office 07:25 Miro Sold, SaaS Valuations Reset 08:40 Ellen Chisa's Path to Boldstart 12:57 Building Dark: A Founder's Story 15:50 Why Ellen Walked Away From Dark 17:48 Becoming a VC at Boldstart 20:54 How Founders Should Use VCs 22:48 Ellen's Next Big Bet 25:05 Inception Stage Investing Explained 27:23 Boston Startups: Rapid Fire 32:00 Advice for First-Time Founders 33:48 Where to Find Ellen Chisa Guest: Ellen Chisa, Partner at Boldstart Ventures https://www.linkedin.com/in/ellenchisa/ Hosts: Matt Crane, Founder of MGMT Boston https://mgmtboston.com/ https://www.linkedin.com/in/matthewhcrane/ Will Lehmann Founder of Step Function VC https://stepfunction.vc/ https://www.linkedin.com/in/wlehmann/ Watch/listen/Subscribe: Spotify: https://open.spotify.com/show/033HueFNlE1LPnEFPvVscs?si=e2351085b40b4334 Apple Podcasts: https://podcasts.apple.com/us/podcast/code-and-cobblestones/id6785977680 Youtube: https://www.youtube.com/@MGMTBoston Code and Cobblestones is a love letter to Boston tech founders. New episodes spotlight the people building the city's next generation of companies. ▶ Subscribe for the rest of the tour. New episodes spotlight the founders and builders putting Boston on the map. Produced in partnership with OBEY Creative, building podcast-driven content engines for B2B founders. One great conversation per week becomes 15-20 assets: clips, LinkedIn posts, blog content, and newsletter material. Learn more at https://obeycreative.com/

6. 

   8 Sept 2026

   How AI Is Changing Cybersecurity | Lior Div, 7AI

   Hackers 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 from a typical tech background. Unit 8200 at 18. Years with the Mossad that don't show up on LinkedIn. Then Cybereason, one of the first EDR companies, built over 12 years. Now 7AI, built with the same co-founder, Yonatan, after a conversation with OpenAI's former head of product convinced him the ground was shifting under the entire industry. We got into: Why Lior thinks we're racing toward a moment when AI can plan, execute, and repeat cyberattacks entirely on its own, and why he still believes defenders can win that race Open weight AI models, which he called a gift with sharp edges, and why he thinks the US should lean into them instead of running from them Autonomous code generation, and why that ship has sailed whether security teams are ready or not (his words, not ours) What 7AI actually does day to day, and why Lior says "AI SOC" is already commodity. Too little, maybe too late, if that's still your whole pitch. The three-star Michelin culture 7AI is building internally, and why some of their strongest hires never worked in tech a day in their life before joining How 7AI runs as a flat, fast organization with almost no recurring meetings, and why Lior says that only works because of how they hire TIMESTAMPS:00:00 Lior Div, 7AI CEO 01:34 AI M&A: Stripe and NVIDIA 03:47 AI Cyberattacks Are Rising 06:09 Open Weight Models Debate 08:27 Risks of AI Code Generation 10:35 Lior's Path: Unit 8200 to Mossad 13:29 Why He Founded 7AI 15:34 What 7AI Actually Does 17:02 Beyond AI SOC 19:38 Building an AI-Native Company 24:10 Hiring for a Builder Culture 28:35 The Michelin Hiring Approach 32:46 Raising Capital for 7AI 35:00 Why Build in Boston 37:10 Rapid Fire Guest: Lior Div,  Co-founder and CEO of 7AI https://7ai.com/ https://www.linkedin.com/in/liordiv/ Hosts: Matt Crane, Founder of MGMT Boston https://mgmtboston.com/ https://www.linkedin.com/in/matthewhcrane/ Will Lehmann Founder of Step Function VC https://stepfunction.vc/ https://www.linkedin.com/in/wlehmann/ Watch/listen/Subscribe: Spotify: https://open.spotify.com/show/033HueFNlE1LPnEFPvVscs?si=e2351085b40b4334 Apple Podcasts: https://podcasts.apple.com/us/podcast/code-and-cobblestones/id6785977680 Youtube: https://www.youtube.com/@MGMTBoston Code and Cobblestones is a love letter to Boston tech founders. New episodes spotlight the people building the city's next generation of companies. ▶ Subscribe for the rest of the tour. New episodes spotlight the founders and builders putting Boston on the map. Produced in partnership with OBEY Creative, building podcast-driven content engines for B2B founders. One great conversation per week becomes 15-20 assets: clips, LinkedIn posts, blog content, and newsletter material. Learn more at https://obeycreative.com/

7. 

   30 Aug 2026

   The Half of Manufacturing Physical AI Ignores | Annie Lu, Laminar

   Every 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 with Laminar. In episode 8 of Code and Cobblestones, Annie joins us, Matt Crane and Will Lehmann, to walk through what physical AI looks like when it's not a robotics story. No sensing the room, deciding, moving an arm. Here the thing being sensed is a chemical reaction, not a room, so Laminar had to build its own version of that camera and lidar from scratch: proprietary sensors first, then closed foundation models trained on the chemistry data, then a direct line into the factory's own control systems. They didn't start with the biggest possible use case. They started with cleaning. Every plant has to shut down between batches and wash everything out, so one product doesn't contaminate the next. Right now, almost every factory in the world runs that cleaning on a fixed schedule that never adjusts, and burns water, energy, chemicals, and downtime doing it. Laminar figured out how to make that process dynamic instead of fixed, and calls it the wedge that earns them the right to expand into everything else: fermentation, filtration, distillation, and beyond. It's why they're now running across six continents, inside seven of the top ten food and beverage companies in the world. What you'll learn: Why Annie treats robotics as the wrong template for physical AI. Chemistry intelligence, not spatial intelligence, is the actual gap How Laminar's stack works end to end: sensors on the equipment, foundation models reading the chemistry, automation acting on it, with zero human in the loop Why clean-in-place became the wedge instead of something bigger or flashier, and how one use case earns the right to expand across a whole plant The real reason legacy manufacturing tech hasn't changed in 60 years, per Annie. It's not that factories resist AI. Nobody built the camera and lidar for chemistry What happened when a competitor told a room of plant managers their model was a black box they couldn't explain, and watched the room turn Her advice for founders on choosing investors: find the ones who already match your DNA, before you ever pitch them Why she thinks Boston's biggest advantage is culture, not capital, and what that means for a physical AI company scaling globally TIMESTAMPS: 00:00 Welcome 01:05 Why Physical AI Now 03:38 Laminar and Process Manufacturing 06:24 The Chemistry Intelligence Stack 09:51 Laminar's Origin Story 12:32 First Principles on the Shop Floor 17:40 Co-Founding With Her Brother 20:32 Winning Trust From Manufacturers 26:57 The Clean-in-Place Wedge 31:57 Advice for Physical AI Founders 35:24 Fundraising and Investor Fit 38:46 Rapid Fire With Annie Lu 40:07 Boston's Manufacturing Culture 42:17 How to Work With Laminar Guest: Annie Lu, Co-founder, CEO at Laminar Hosts: Matt Crane, Founder of MGMT Boston https://mgmtboston.com/ https://www.linkedin.com/in/matthewhcrane/ Will Lehmann Founder of Step Function VC https://stepfunction.vc/ https://www.linkedin.com/in/wlehmann/ Watch/listen/Subscribe: Spotify: https://open.spotify.com/show/033HueFNlE1LPnEFPvVscs?si=e2351085b40b4334 Apple Podcasts: https://podcasts.apple.com/us/podcast/code-and-cobblestones/id6785977680 Code and Cobblestones is a love letter to Boston tech founders. New episodes spotlight the people building the city's next generation of companies. ▶ Subscribe for the rest of the tour. New episodes spotlight the founders and builders putting Bosto

8. 

   18 Aug 2026

   Building AI Tools for the 90% of Businesses Tech Forgot | Shannon Kay, Topline Pro

   Shannon 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 a desk, and don't have time to learn point-and-click software. The conversation runs from a stat that reframes the whole AI conversation (of the 2.6 million home service businesses in the US, only the top 10% have anything resembling a tech stack) to why "trust but verify" matters more than ever after watching an AI-driven hedge fund implode, to the customer who found out their AI assistant was quietly qualifying leads for them while they were out to dinner. What you'll learn: Why Shannon built Topline Pro's Sidekick around "get work, win work, get paid" instead of the usual SaaS feature list How a COVID-era side project called Dwelling turned into ProFo, then Topline Pro, after one wrong pivot pointed her toward the right one Why she'd rather a customer never open the app at all, and what "done for you" means when your users are on a ladder, not at a desk The real risk with AI inside a company, per Shannon: not inaccuracy, but rewarding the wrong behavior, and how Topline Pro's "AI-native employee of the month" tries to fix that What Airtable's $1.2B exit, an AI hedge fund's collapse, and the Agency AI–Klaviyo deal have in common as lessons for founders right now Her advice for founders building in "unsexy" markets: find the investors who already get it before you ever pitch them Why incrementalism earns trust with some customers, and showing the whole platform earns it faster with others TIMESTAMPS 00:00 Shannon Kay, Topline Pro Co-Founder Joins the Show 02:19 Airtable's $1.2B Acquisition Explained 05:07 AI Hedge Fund Collapse: Startup Risk Lessons 08:57 Klaviyo Buys Agency AI: Founder Obligations 12:45 Shannon Kay's Career Path: Clemson to Harvard 15:46 Founding Topline Pro: From Dwelling to AI Startup 20:03 Inside Sidekick: AI for Home Service Businesses 22:17 Designing AI Products for Non-Tech Small Businesses 26:40 Building Customer Trust Without Lock-In Contracts 28:54 Raising a $27M Series B: Fundraising Advice 34:01 Rapid Fire: AI Hiring and Boston Startups 39:51 Final Takeaway and Episode Wrap-Up Guest: Shannon Kay, Co-founder, COO at Topline Pro https://www.toplinepro.com/ https://www.linkedin.com/in/shannonekay/ Hosts: Matt Crane, Founder of MGMT Boston https://mgmtboston.com/ https://www.linkedin.com/in/matthewhcrane/ and Will Lehmann Founder of Step Function VC https://stepfunction.vc/ https://www.linkedin.com/in/wlehmann/ Watch/listen/Subscribe: Spotify: https://open.spotify.com/show/033HueFNlE1LPnEFPvVscs?si=e2351085b40b4334 Apple Podcasts: https://podcasts.apple.com/us/podcast/code-and-cobblestones/id6785977680 Produced in partnership with OBEY Creative, building podcast-driven authority content engines for B2B founders. Learn more at https://obeycreative.com Code and Cobblestones is a love letter to Boston tech founders. New episodes spotlight the people building the city's next generation of companies. ▶ Subscribe for the rest of the tour. New episodes spotlight the founders and builders putting Boston on the map. Produced in partnership with OBEY Creative, building podcast-driven content engines for B2B founders. One great conversation per week becomes 15-20 assets: clips, LinkedIn posts, blog content, and newsletter material. Learn more at https://obeycreative.com/

9. 

   9 Aug 2026

   Agent Abundance: Jack O'Brien on AI's Real Bottleneck | Ep. 6

   Subconscious 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 customer: 95% compressed away, agents never noticed) The case for American open weights, and why Jack calls the closed-model argument self-serving Why Boston's talent density and the Mass AI Coalition make it a real place to build deep tech Chapters 00:00  Intro: the mattress company and a $300K run rate 02:00  OpenScout, OnePager, and the power law of fundraising 03:20  Open weights vs closed, and American AI leadership 05:17  Will open models catch the frontier? 07:03  Cybersecurity, jailbreaks, and the Hugging Face incident 09:41  Cephable and the push to on-device AI 10:21  Edge models: why reasoning compresses well 13:02  Career arc: IBM blockchain, Google Search, the founder bug 16:00  The Subconscious origin story (and a Guinness at Shy Bird) 17:50  Building inference for agents, not chatbots 20:12  Why the inference runtime is the right layer to own 22:51  Inside the tech: context compression and caching 25:42  Tim Run and the Tim models 26:15  The path to billions of agents 28:51  Why Boston: talent density and the Mass AI Coalition 31:45  Biggest lessons: nothing goes according to plan 33:30  Ruthless posting and the war on AI slop 36:29  Message to builders in the agent era 37:18  Rapid fire 39:46  The stat that stopped the room: 95% compression 40:52  Boston's under-the-radar company: Alpaca 42:15  The Avengers scenario: Suno and the Wei song 43:15  How Boston can help Subconscious 44:37  One big takeaway: agent abundance GUESTS AND HOSTS: Guest: Jack O'Brien, co-founder & CEO, Subconscious. https://www.subconscious.dev/ https://www.linkedin.com/in/thejackobrien/ Hosts: Matt Crane, MGMT Boston https://mgmtboston.com/ https://www.linkedin.com/in/matthewhcrane/ Will Lehmann, Step Function Investments. https://stepfunction.vc/ https://www.linkedin.com/in/wlehmann/ Watch/listen/Subscribe: Spotify: https://open.spotify.com/show/033HueFNlE1LPnEFPvVscs?si=e2351085b40b4334 Apple Podcasts: https://podcasts.apple.com/us/podcast/code-and-cobblestones/id6785977680 Produced in partnership with OBEY Creative, building podcast-driven authority content engines for B2B founders. Learn more at https://obeycreative.com

10. 

    30 Jul 2026

    How AI Agents Are Transforming Engineering Teams | Ep. 5 with Jellyfish CEO Andrew Lau

    Andrew 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. The conversation runs from a stat that should worry every engineering leader (top companies went from 7% to nearly 50% of PRs handled by Claude in under a year) to what it even means for a model to be "Chinese" or "American" anymore, to the side project that quietly became Jellyfish's whole business. What you'll learn: Why Andrew says every engineer is now "a manager of agents, not humans," and what that does to team structure How the ADLC (agentic development lifecycle) is replacing the SDLC, and what that shift actually looks like day to day The real story behind Jellyfish's pivot, from a side project called Copilot Impact to the company's main business by the end of 2025 Why open weight models are everywhere in conversation but barely showing up in production Andrew's bet on how AI model regulation actually plays out, and why brand trust matters more than model transparency The honest tradeoffs of building in Boston instead of the Bay Area, including why he's still on a plane every three weeks Lessons from mentors Steve Papa and Keith Johnson, and why customer development matters more now, not less Timestamps:00:00 Andrew Lau Introduction 01:14 Building Real Relationships in Tech 02:05 Podcast Format and Hot Takes 02:34 Open Weight AI Models Explained 07:12 Why AI Cost Is Slowing Adoption 08:51 AI Policy and Data Sovereignty 11:17 Boston Startups and Physical AI 15:13 Mega Seed Rounds Explained 19:26 Andrew Lau Career Story 23:51 Why Jellyfish Was Founded 28:06 The Truth About AI Refounding 28:27 Copilot Impact Origin Story 30:17 From Side Project to Core Business 31:56 Every Engineer Is Now a Manager 34:43 Boston vs Silicon Valley 38:36 Startup Mentors and Focus 40:42 Why Customer Development Still Matters 42:55 AI Code Metrics Explained 45:38 Claude Writes 50% of Pull Requests 47:27 Final Thoughts on AI Transformation Guest: Andrew Lau, Co-Founder and CEO of Jellyfish. Previously at Nanigans, and LoopIt. Resources: Jellyfish Engineering Trends Report, July 2026 Jellyfish website: https://jellyfish.co/ Follow Andrew on LinkedIn: https://www.linkedin.com/in/amlau/ Hosts: Matt Crane, Founder of MGMT Boston and Will Lehmann Founder of Step Function Code and Cobblestones is a love letter to Boston tech founders. New episodes spotlight the people building the city's next generation of companies. ▶ Subscribe for the rest of the tour. New episodes spotlight the founders and builders putting Boston on the map. Produced in partnership with OBEY Creative, building podcast-driven content engines for B2B founders. One great conversation per week becomes 15-20 assets: clips, LinkedIn posts, blog content, and newsletter material. They close the Authority Gap: the distance between your expertise and the market's awareness of it. Learn more at https://obeycreative.com/

11. 

    23 Jul 2026

    Inside Nebulock's $25M Series A | Ep. 4 with Damien Lewke

    Damien 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 runs from the open-source AI models rewriting the threat model, to the $40 he put in a bank account to start the company, to what a professional football career taught him about hiring. What you'll learn Why open-weight models like GLM 5.2 shift the advantage toward attackers, and what founders should do about it What a "hunt-first" security platform actually does, explained plainly The origin of Nebulock: 90 customers in 90 days, a 30-page manifesto, and a $40 bank account How Damien hires, and the most underrated seed-stage hire right now The real advantages of building a cybersecurity company in Boston Three lessons from pro football that carry into founding a company Chapters 00:00 Episode 4, and our guest Damien Lewke 01:46 Headlines: Mythos, Fable 5, and the open-source moment 06:09 Two Boston raises: Nebulock and Scaled Cognition 07:22 Inside the $25M Series A with FirstMark 11:15 A World Cup detour: football lessons for founders 15:32 From Northrop Grumman to early CrowdStrike 20:02 Palo Alto, Australia, and back to MIT 22:51 What a hunt-first security platform actually is 24:06 The spark: a manifesto and a $40 bank account 28:57 Three lessons: 90 customers, a high bar, get on a plane 33:55 Why build in Boston? 37:08 Rapid fire 40:09 One message to cyber builders Guest: Damien Lewke, Founder and CEO of Nebulock. Previously at Arctic Wolf, Palo Alto Networks, CrowdStrike, and Northrop Grumman. Graduate research at MIT CSAIL. Hosts: Matt Crane, Founder of MGMT Boston and Will Lehmann Founer of Step Function VC Mentioned: Nebulock, FirstMark, Step Function, CrowdStrike, Palo Alto Networks, Arctic Wolf, Northrop Grumman, MIT CSAIL, UCLA, Cribl, Bain Capital, Scaled Cognition, RSA, Veracode, Rapid7, Jellyfish, and Boston's security community. Code and Cobblestones is a love letter to Boston tech founders. New episodes spotlight the people building the city's next generation of companies. ▶ Subscribe for the rest of the tour. New episodes spotlight the founders and builders putting Boston on the map. Produced in partnership with OBEY Creative, a boutique authority media firm in the heart of Boston. We specialize in building Authority Capital for founder-led brands through podcasts and content engines that transform visionary builders into the primary voice of their industry. Learn more at https://obeycreative.com/

12. 

    16 Jul 2026

    Why Boston Is Where You Build Hard Things | Ellen Rubin

    Ellen 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 Boston Public Schools' new AI literacy requirement matters, and how BostonPublic.ai (with Kayak's Paul English) is getting there first How the "crossing the chasm" playbook broke, and what replaced it in the AI era What makes a customer worth chasing, and how to measure real urgency instead of polite excitement Why AI has to run through every part of a company, not just the product The most underrated seed-stage hire right now The real advantages of building in Boston (and the honest disadvantages) What changes when you leave the operator seat for the other side of the table Chapters 00:00 A first guest, and why this one 00:56 Boston's new AI literacy requirement, and BostonPublic.ai 06:12 Three seed rounds: Enlay, Flux, and Pillar 10:01 What the Tartan Army taught Matt about B2B sales 14:34 The accidental entrepreneur: Booz Allen to Netezza 19:20 Founding CloudSwitch and ClearSky Data 23:07 Choosing your customer, and the chasm collapsing 28:43 The real advantages of building in Boston 31:27 Leaving the operator seat for Glasswing 34:18 Building an AI-native team in the age of agents 38:52 Rapid fire 42:50 Stop talking about what Boston doesn't have Guest: Ellen Rubin, Operating Partner at Glasswing Ventures. Founder of CloudSwitch (acquired by Verizon) and ClearSky Data (acquired by AWS); early executive at Netezza through its IPO. Hosts: Matt Crane and Will Lehmann. Mentioned in this episode: Glasswing Ventures, BostonPublic.ai, Paul English (Kayak), the Mass AI Coalition, Enlay, Flux, Pillar, Allure Security, Realm Security, Whoop, and Boston Public Schools. Code and Cobblestones is a love letter to Boston tech founders. New episodes spotlight the people building the city's next generation of companies. ▶ Subscribe for the rest of the tour. New episodes spotlight the founders and builders putting Boston on the map. Produced in partnership with OBEY Creative, a boutique authority media firm in the heart of Boston. We specialize in building Authority Capital for founder-led brands through podcasts and content engines that transform visionary builders into the primary voice of their industry. Learn more at https://obeycreative.com/

13. 

    8 Jul 2026

    What a Startup Will Actually Look Like in 12 Months | Building in the AI Era in Boston

    Matt 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 with AI How Lovable opened software building from 25 million developers to nearly everyone, with a go-to-market team growing fast in Boston Why Whoop's focus is its advantage in physical AI at a $10B-plus valuation A hedge fund rule from Adage Capital that applies to building any company: take risk only where you have an edge Why the new "haves" in a K-shaped economy are defined by skill, not capital Timestamps: 00:00 Cold open: the phone screen that went sideways 02:59 Quick hits: Fable, Mythos, and the kill switch 07:09 Lovable, vibe coding, and opening the aperture 12:06 Whoop, focus, and physical AI 15:41 The main topic: what a company looks like in 12 months 17:42 Org charts, design, and enterprise sales in the AI era 29:34 Closing takeaways and how to plug into Boston tech Subscribe for the rest of the tour. New episodes spotlight the founders and builders putting Boston on the map. Produced in partnership with OBEY Creative. OBEY is a boutique branding and authority media consultancy based in Boston. We build Authority Capital for founder-led brands in finance, tech, and professional services. Learn more at https://obeycreative.com/

14. 

    30 Jun 2026

    The $1.4B Code Company and the AI Music Lab Hiding in Boston

    Matt 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 every founder is wrestling with right now How AI-native seed startups and big public companies are adopting AI at completely different speeds The Boston companies raising mega-rounds: Suno, Blitzy, Whoop, Lila Sciences, and more Why loyalty and patient, durable company-building define the Boston founder How Laminar uses AI to make food and beverage plants run more efficiently Chapters:00:00 Welcome to Code and Cobblestones 01:05 What "code and cobblestones" means 02:01 Will Lehmann and Step Function 03:51 Matt Crane and MGMT Boston 04:59 Boston Tech Week recap 08:26 The Mass AI Coalition and Klaviyo kickoff 10:31 How AI is changing company building: tokens vs. talent 17:12 Where the dollars are moving: mega-rounds 19:43 Life sciences, Lila, Blitzy, and Suno 23:59 Is Boston underrated, rated, or overrated? 30:31 Loyalty, "next man up," and second-order AI builders 34:05 Laminar, Lovable, and the security speakeasies 39:13 Closing thoughts and what's next Subscribe for the rest of the tour. New episodes spotlight the founders and builders putting Boston on the map. Produced in partnership with OBEY Creative. OBEY is a boutique branding and authority media consultancy based in Boston. We build Authority Capital for founder-led brands in finance, tech, and professional services. Learn more at https://obeycreative.com/

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