Code and Cobblestones

codeandcobblestones

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

Episodes

  1. 2d ago ·  Video

    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 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. Sep 28 ·  Video

    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/

  3. Sep 21 ·  Video

    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/

  4. Sep 8 ·  Video

    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/

  5. Aug 30 ·  Video

    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 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. Aug 18 ·  Video

    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/

  7. Aug 9 ·  Video

    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

  8. Jul 30 ·  Video

    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/

  9. Jul 23 ·  Video

    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/

  10. Jul 16 ·  Video

    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/

  11. Jul 8 ·  Video

    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/

  12. Jun 30 ·  Video

    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/

  • 12 Episodes

About

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

Information

  • Creator
    codeandcobblestones
  • Years Active
    2026
  • Episodes
    12
  • Rating
    Explicit
  • Copyright
    © Copyright 2026 All rights reserved.
  • Show Website
    Code and Cobblestones