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

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

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

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:

Timestamps:

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:

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/

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

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/

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

Chapters 

00:00 A first guest, and why this one

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/

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:

Timestamps: 

00:00 Cold open: the phone screen that went sideways

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/

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:

Chapters:

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/