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

What does it take to walk away from a big idea and start over inside the same company? In this episode of Not Another CEO Podcast, Adam Dell opens up about the journey behind Domain Money.

A serial Founder with multiple exits, Adam reflects on making hard pivots, recruiting top talent personally, navigating investor psychology, and why execution, not ego, is what earns the right to exist. He also shares how AI is transforming financial services and why the emotional highs and lows of startup life never really go away.

Takeaways:

• Recruiting Personally, Relentlessly: Adam still personally recruits on LinkedIn, often spending hours each day identifying talent, crafting outreach, and filtering for startup fit. He believes CEO-led recruiting cuts through noise and shows prospects the role's importance.
• A Pivot Before the Crash: Originally conceived as a crypto banking platform, Domain Money pivoted early. Adam made the call based on market fundamentals and moved decisively, even when his team was still optimistic about the original vision.
• Transparent, Yet Optimistic Leadership: During the pivot, Adam prioritized honesty with his team while maintaining belief in the mission. He communicated openly about uncertainty and made clear that success was entirely on them.
• Investor Support Built on Track Record and Clarity: Adam credits his investor relationships and clear, data-backed thinking for enabling a smooth pivot. Though they challenged him, his investors supported the shift and recognized the market opportunity in personal finance.
• AI as a Backbone, Not a Gimmick: AI plays a major role in Domain Money’s operations, especially in improving planning efficiency. Adam is enthusiastic about AI’s pace and scope of change, calling it central to his product vision.
• The Mental Game of Being a Founder: The pivot at Domain Money required layoffs and letting go of certainty. Adam talks candidly about staying objective under pressure, fighting through doubt, and surrounding himself with trusted mentors while still waking up every day to earn it.

Quote of the Show:

• "That uncertainty, that thing inside of you that forces you to figure it out, is very motivating to me and I quite enjoy it." - Adam Dell

Links:

• LinkedIn: https://www.linkedin.com/in/adamdell/
• Website: https://www.domainmoney.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 #DomainMoney

Chapters:

00:00 Intro

01:25 Recruiting Strategies for Startups

07:15 Fundraising Insights and Market Sentiment

11:46 The Evolution of Domain Money

16:25 Navigating Pivots and Team Buy-In

23:07 Growth Strategies and Partnerships

26:20 Acquisitions and Exits

29:23 Strategic Partnerships and Revenue Growth

30:37 The Impact of AI on Technology and Business

35:12 AI in Financial Planning and Wealth Management

39:51 Challenges and Pivots in Business

49:09 Personal Background and Entrepreneurial Journey

57:37 Advice for Aspiring Entrepreneurs

01:00:30 Outro

What’s it really like to build a billion-dollar business with your spouse, and live to tell the story? In this special live episode, David Politis sits down with Kass and Mike Lazerow, Co-Founders of Buddy Media and authors of Shoveling $H!T: A Love Story About an Entrepreneur’s Messy Path to Success..

They open up about building cult-like culture, radical transparency, co-founder dynamics, fundraising strategies, pivots, parenting, and everything in between. With humor and honesty, the Lazerows share the unvarnished truth of what it takes to build something meaningful, and survive the chaos along the way.

Takeaways:

• Building a Cult-like Culture with Intentionality: Kass shares how she focused on creating a high-trust, high-engagement company culture through rituals, transparency, shared values, and even handwritten birthday cards. The foundation was purpose-driven work, and a lot of cupcakes.
• Radical Focus as a Leadership Imperative: Mike emphasizes the importance of choosing just 3–5 core priorities each quarter and communicating them relentlessly. He admits that his natural state is distraction, and that focus, both personal and organizational, is what drives growth.
• Fundraising Is a Relationship Business: Mike describes how he built trust with investors over time by sending updates, even to people who said no, and treating everyone with respect, from analysts to GPs. He reframes fundraising as offering a great opportunity, not asking for a favor.
• The Power (and Pain) of Pivoting: The Lazerows recount the early missteps at Buddy Media, from virtual currency to raffles, before landing on a scalable SaaS product. They stress the importance of cutting old lines of business fast and committing fully to what’s next.
• Marriage and Co-Founding: They describe co-founding as an intense version of marriage, with shared values, relentless communication, and radical honesty. Kass encourages couples to embrace their lanes and support each other’s growth, both professionally and personally.
• Startups and Parenting Don’t Balance, But They Can Work: Kass shares how they intentionally deprioritized social commitments and accepted imperfection at home to build their company. She encourages other founder-parents to aim for 80%, not perfection, and to give themselves grace.

Quote of the Show:

• "Being a founder, there’s no worse way to spend your day. And it’s awesome, right?" - Mike Lazerow

Links:

• Kass’ LinkedIn: https://www.linkedin.com/in/kasslazerow/
• Mike’s LinkedIn: https://www.linkedin.com/in/lazerow/
• Get Their Book: https://shovelingshit.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 #Shoveling$H!T

Chapters:

00:00 Intro

00:46 Podcast Journey and Growth

01:41 Acknowledging Sponsors and Supporters

03:56 Introducing Cass and Mike Lazaro

05:33 Building Buddy Media: Key Strategies and Insights

08:19 Challenges and Successes in Leadership

14:09 The Importance of Transparency

15:19 Husband-Wife Co-Founders: A Unique Dynamic

20:09 Fundraising and Building Relationships

27:46 Marketing and Branding Strategies

34:09 Thought Leadership and Public Speaking

36:36 Navigating Business Pivots

38:25 The Birth of Buddy Media

40:31 Challenges and Successes of Custom Apps

45:20 Balancing Family and Business

48:50 Advice for Aspiring Entrepreneurs

54:58 Building a Positive Company Culture

01:02:21 Q&A with the Audience

01:11:11 Outro

How do you scale yourself as your company scales? Tien Tzuo, Founder and CEO of Zuora, joins David Politis to share hard-won lessons from his journey building a category-defining SaaS company.

In this candid conversation, Tien reflects on early team building, founder growth inflection points, strategic planning, and the leadership gaps many founders face as their companies mature. Drawing on his new book, Founders Keepers, he reveals why great founders often succeed in spite of themselves—and how to turn blind spots into leadership strengths.

Takeaways:

• Category Creation and Team Building: Tien reflects on the impact of coining the term “subscription economy” and credits early success to not just vision, but team-building. He shares how Zuora evolved through multiple “generations” of leadership, and how long-tenured team members were balanced with fresh perspectives as the company grew.
• Recognizing the Founder’s Growth Curve: Tien describes a critical inflection point when Zuora hit ~150 employees—a moment where personal evolution became necessary. That led him to executive coach Rich Hagberg and a deeper understanding of how personality traits drive both success and failure.
• The Three Pillars of Leadership: Through data-driven leadership profiling, Tien outlines the three dominant founder traits—vision, execution, and relationships. He shares that most founders score high on vision but often struggle with execution and people management, which can lead to common pitfalls.
• Owning Your Leadership Gaps: Tien reveals his own leadership profile—high vision, medium execution, low relationship—and how understanding that helped him improve in areas like prioritization, team-building, and relationship development. He even shared his leadership gaps openly with his company to build trust and culture.
• A Better Way to Do Strategic Planning: Borrowing a method from Brad Smith (former Intuit CEO), Tien walks through how Zuora moved from a 2-day offsite to a 6-month annual strategy cadence. It includes deep research, team ownership of ideas, board engagement, and company-wide evangelism—because a founder’s job is to repeat the story until it sticks.
• Letting Go Without Losing Drive: He emphasizes the importance of giving leaders autonomy and building space into his calendar—cancelling recurring meetings, avoiding over-scheduling, and giving energy to what matters most. He advises founders to avoid being the bottleneck and protect organizational focus by saying “no” to distractions.

Quote of the Show:

• "The same things that make up a founder, that make us do what we do, ultimately are the seeds sewn of our own destruction." - Tien Tzuo

Links:

• LinkedIn: https://www.linkedin.com/in/tientzuo/
• Website: https://www.zuora.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 #Zuora

Chapters:

00:00 Intro

02:00 The Journey of Building Zuora

03:59 Scaling and Team Dynamics

07:43 Founder's Journey and Coaching

22:12 Strategic Planning and Execution

30:28 Frameworks for Strategic Alignment

32:33 Self-Awareness and Leadership

34:10 Execution-Oriented Teams

37:03 Lessons from Salesforce

38:07 The Power of Storytelling

40:59 Advice on Managing Time

43:33 Biggest Challenges and Overcoming Them

46:24 Future Vision for Zuora

48:22 Personal Journey and Motivation

52:33 Advice for Aspiring Founders

54:13 Outro

How do you grow a startup into a transformative force in a highly regulated, slow-moving industry? John Swigart, Co-Founder and CEO of Pie Insurance, joins David Politis to discuss the importance of decisive leadership, the balance between founder intuition and executive delegation, and how execution at scale can be a long-term competitive advantage.

From assembling a thoughtful board to reorienting a business for profitability, John shares lessons from building a modern insurance company from scratch.

Takeaways:

• Decisiveness Around Leadership Transitions: John emphasizes making tough calls on leadership team members who may no longer be the right fit as a company evolves. Waiting too long creates compounding challenges and stalls progress.
• Balancing Founder Involvement with Delegation: He reflects on the “founder mode” concept, describing the need for leaders—founder or not—to stay close to the details while avoiding micromanagement. Clarity and context are key.
• The Decision-Making Matrix at Pie: John explains Pie’s internal framework for decision-making, which clearly defines who owns decisions, who contributes input, and how final calls are made—helping empower teams without chaos.
• Why Pie Competes in a Difficult Industry: Despite the dominance of legacy players in insurance, John saw a real opportunity: a fragmented market with outdated tech and poor customer experience. Pie’s modern, data-driven model aims to change that.
• Process Power as a Competitive Moat: Pie focuses on doing hundreds of small things better than the competition. John describes how consistent operational execution and better technology form a durable advantage over time.
• Adapting to a Profitability-Focused Environment: John details the major internal shift required when venture markets changed in 2022—from “grow at all costs” to sustainable, efficient operations. Layoffs and restructuring followed, but the business emerged stronger.
• Advice to His Younger Self: John would tell his younger self—and others early in their careers—to say yes to opportunities that offer growth. Don’t over-optimize for money or title; focus on learning and exposure instead.

Quote of the Show:

• "Early in your career, optimize on learning growth, exposure, opportunity, not on money or title or, or anything of that nature." - John Swigart

Links:

• LinkedIn: https://www.linkedin.com/in/johnswigart/
• Website: https://www.pieinsurance.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 #PieInsurance

Chapters:

00:00 Intro

01:42 Key Decisions and Leadership Challenges

07:24 Building and Evolving Leadership Teams

11:03 The Concept of Founder Mode

20:58 Competing in a Highly Regulated Market

31:13 Early Days and Customer Acquisition

31:53 Early Days of Multi-Channel Distribution

34:35 Fundraising Challenges and Successes

36:59 Building an Impressive Board

42:33 Navigating Business Challenges

48:39 Founding a Company Later in Life

53:46 Personal Growth and Mentorship

57:06 Pivotal Career Moments

01:00:48 Advice for Aspiring Entrepreneurs

01:02:17 Outro

What happens when a strong vision, real traction, and early funding still aren’t enough? In this Failing Forward episode of Not Another CEO Podcast, Sasha Pasulka shares the journey behind her AI startup, Elka.

Sasha opens up about the thrill of building, the challenge of fundraising, the reality of launching with imperfect tech, and the emotional toll of shutting down a business you deeply believe in. From her days as a software engineer to founding one of the most-read blogs of its era, Sasha reflects on learning to trust herself, ask for help, and move on with grace.

Takeaways:

• The AI Aha Moment: Sasha was re-energized to found again after ChatGPT launched publicly in late 2022. She saw an opportunity to solve marketing problems that hadn’t been addressable before due to the language limitations of software.
• Solving a Real Problem from Experience: The product idea came from Sasha’s time at Tableau, where hours of valuable customer video content went unused because it was too hard to search. Elka aimed to automate finding and surfacing those insights for sales teams.
• Alpha and Beta Lessons: The team built fast and launched a beta early to help with fundraising, but users got frustrated with AI inconsistencies. Sasha onboarded every beta customer herself, but admits they may have opened access too soon.
• The Limits of Non-Deterministic Tech: Building on an LLM proved unpredictable. Despite numerous safeguards, the AI struggled with tasks like basic math and clip durations—issues Sasha says may have improved if they had more time to wait out tech advances.
• The Fundraising Wall: While Sasha successfully raised an angel round, later fundraising stalled. She reflects on her discomfort with the performative aspects of pitching and how authenticity may have hurt her in a system designed for bold salesmanship.
• Support and Disappointment: From angel investors to past coworkers, Sasha describes the surprising people who showed up to help—and the ones who didn’t. She credits her team, co-founder, and a few critical mentors with getting them as far as they did.
• Learning, Letting Go, and Looking Ahead: Sasha closes with advice to bring on a co-founder who can fundraise and a reminder to stop being intimidated by others’ confidence. She shares how the journey helped her understand her strengths and what she’ll do differently next time.

Quote of the Show:

• "They may be in positions of power right now, but they're not necessarily smarter than you. They're not better than you… Don’t waste so much energy being intimidated by these people." - Sasha Pasulka

Links:

• LinkedIn: https://www.linkedin.com/in/spasulka/
• TikTok: https://www.tiktok.com/@sashaiscooking

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 #ElkaAI

Chapters:

00:00 Intro

03:07 The Aha Moment: Founding Elka AI

04:30 Challenges in Marketing and AI Solutions

09:42 Building the Product: Alpha and Beta Phases

18:07 The Struggles of Fundraising and Leadership

25:22 Navigating Luck and Timing in Entrepreneurship

27:38 Key Decisions and Reflections

31:56 Navigating AI Non-Determinism

33:01 Support System and Key Influences

36:38 Fundraising Challenges and Lessons

42:40 Gender Dynamics in Fundraising

48:47 Personal Journey and Reflections

56:01 Advice for Future Founders

01:00:05 Outro