What can you learn from someone who built and sold multiple enterprise startups, led teams through acquisitions, and now mentors the next generation of Founders? In this episode, Ellen Rubin shares lessons from her journey as a serial Founder and now Operating Partner at Glasswing Ventures.

She talks about building strong cultures, nurturing early career talent, supporting women in tech, and helping startups avoid hype in favor of real-world value. From lunch-and-learns to boardroom decisions, Ellen reflects on what it takes to grow people and companies with clarity and purpose.

Takeaways:

• How to Spot Future Founders Inside Your Company: By encouraging curiosity and inviting team members into strategic conversations, Ellen helped cultivate talent that would eventually become leaders. She looked for people who asked questions, engaged outside their lane, and showed deep interest in how the business works.
• Practical Support for Women in Tech: Ellen shares her multi-layered approach to supporting women in technology. She has a personal policy of responding to every outreach from a woman Founder or aspiring leader, offering both encouragement and actionable help.
• Building Strong Local Ecosystems: As a passionate advocate for Boston’s tech scene, Ellen emphasizes the importance of keeping post-exit Founders and big companies engaged with the next generation. She believes physical proximity and local mentorship still matter, even in a hybrid work world.
• The Value of Regular All-Hands and Real Transparency: At her startups, Ellen hosted weekly all-hands to build alignment and trust. She prioritized consistent updates, company-wide visibility into fundraising stages, and direct Q&A with leadership to keep teams connected and focused.
• Lessons from Amazon and the PR/FAQ Method: Ellen talks about her time at Amazon and how the press release and FAQ approach to product planning shaped her thinking. She encourages Founders to use writing and storytelling as a way to clarify product vision before building anything.
• AI That Solves Real Problems: Now an Operating Partner at Glasswing Ventures, Ellen focuses on “intelligent verticals” that use AI to automate industry-specific workflows. She emphasizes the importance of AI being integral to the product, not just a wrapper for marketing.

Quote of the Show:

• "Why wouldn't you wanna be the Founder CEO? That's like the coolest thing in the whole world." - Ellen Rubin

Links:

• LinkedIn: https://www.linkedin.com/in/ellenrubin/
• Website: https://glasswing.vc/

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast
• Transistor: https://podcast.notanotherceo.com/

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Chapters:

00:00 Intro

01:45 Key to Startup Success: Building the Right Team

03:08 Exposing Team Members to the Bigger Picture

06:08 Encouraging Curiosity and Engagement

09:45 Supporting Women in Technology

15:03 Challenges in the Tech Industry

17:50 The Boston Tech Ecosystem

21:37 Importance of Local Community in Remote Work Era

27:08 Customer Engagement and Feedback

30:07 Effective Operating Rhythms

35:23 Lessons from Amazon

37:50 Navigating the M&A Process

38:31 Deciding the Right Time to Sell

40:59 Taking Calls from Corporate Development

44:30 The AI Revolution: A 70-Year Overnight Sensation

46:00 The Role of AI in Modern Enterprises

01:01:58 The Importance of Mentorship

01:06:25 Balancing Entrepreneurship and Family

01:09:13 Advice for Aspiring Entrepreneurs

1:10:27 Outro