Description

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.

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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.

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