Code and Cobblestones

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/

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

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/

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/

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/

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/
 

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/