Code and Cobblestones

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/