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/

#NotAnotherCEO #BusinessSuccess #Causely

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

What happens when you try to fund and scale a legal tech company in one of the most rigidly regulated industries in the country? In this episode, Todd Richheimer shares how he grew Lawfty into a tech-powered personal injury platform that has generated over 55,000 cases and nearly a billion dollars in recoveries.

From taking his first client calls on his cell phone to surviving a last-minute funding failure, Todd speaks openly about scaling, leadership evolution, and what the legal world looks like as regulation and AI collide.

Takeaways:

• Finding the Right Co-Founder in the Hamptons: Todd met his Co-Founder, a former MIT engineer, in the Hamptons. They spent a year working on ideas every Saturday before launching Lawfty, combining Todd’s legal background with Mike’s technical skills.
• Building with Complementary Strengths: Todd surrounded himself with people who could help him see around corners. He emphasizes that knowing your weaknesses and recruiting to fill them is the most impactful thing he's done as a Founder.
• The Power of Shameless Outreach: Todd started the company by emailing every contact in his Gmail account. With no product and no revenue, he relied on personal relationships and a willingness to ask for help to land early clients and supporters.
• Leading with Empathy and Integrity: Todd acknowledges his struggle with letting underperforming team members go, especially when they're good people. Instead of defaulting to layoffs, he focuses on reshuffling and preserving relationships where possible.
• From Answering Phones to Scaling Teams: For over a year, Todd personally fielded every intake call. That hands-on experience shaped how he hires and builds processes today, and made him intimately familiar with every part of the business.
• Navigating Capital Constraints Without Venture Money: Due to legal restrictions, Lawfty couldn’t raise institutional equity. Todd had to get creative with structured finance, high-interest loans from individuals, and careful debt planning to scale the company.
• Legal Tech’s Big Bang Moment: Todd sees the convergence of AI and regulatory change as a generational opportunity for the legal industry. With non-lawyers now allowed to own law firms in more jurisdictions, he believes the space is finally ripe for innovation and scale.

Quote of the Show:

• "Standing up for individuals always felt right to me… so I didn’t necessarily care about the personal view that people had." - Todd Richheimer

Links:

• LinkedIn: https://www.linkedin.com/in/todd-richheimer-esq/
• Website: https://www.lawfty.com/

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/

#NotAnotherCEO #BusinessSuccess #Lawfty

Chapters:

00:00 Intro

01:41 The Importance of Complementary Skill Sets

02:41 Finding a Co-Founder in an Unlikely Place

03:44 Building Lawfty: From Idea to Execution

06:19 Challenges and Strategies in Team Building

09:29 Navigating the Interview Process

12:47 Understanding Lawfty’s Business Model

16:26 Early Customer Acquisition Tactics

20:57 Fundraising Journey and Lessons Learned

26:38 Scaling as a CEO

29:31 The Legal Tech Revolution

32:09 Challenges in Legal Services

34:52 Building a Tech-Enabled Law Firm

37:14 Overcoming Industry Stigma

42:35 Fundraising Challenges and Solutions

47:01 Personal Journey and Entrepreneurial Drive

54:12 Advice for Aspiring Entrepreneurs

56:48 Outro