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

How do you build a global tech company from scratch—and stay married while doing it? Nicolas and Alina Vandenberghe, Co-Founders and Co-CEOs of Chili Piper, join David Politis for an in-depth conversation on bootstrapping, hiring globally, handling layoffs, and building community with intention.

From convincing early customers to prepay for a non-existent product to implementing a decision-making framework that replaces most meetings, they reveal what it really takes to grow a successful, remote-first company together.

Takeaways:

• Buy-In Without a Product: By focusing on real, unsolved pain points and validating ideas through milestone-based contracts, they built confidence and traction before writing a single line of code.
• Hiring Across Borders for Talent, Not Cost: Nicolas explains how they built Chili Piper by hiring globally from day one, prioritizing talent regardless of geography. They developed a compensation framework by region and job level to ensure fairness while scaling a fully remote team.
• Building Culture Through Annual Global Gatherings: The company brings its global team together once a year for a shared in-person experience—despite the cost. The cultural exchange deepens trust and unity across a fully distributed team, making it one of the most valuable investments they make each year.
• Scaling with Asynchronous Decision Memos: To cut down on meetings, Chili Piper developed a company-wide decision memo process. Each decision includes context, options, and a designated “consensus caller.” This system supports clarity, inclusion, and transparency without constant live discussions.
• Overcoming Financial Stress in a Bootstrapped Journey: Nicolas recounts moments when they had no cash in the bank—offering equity in lieu of salaries to early employees. Those shares later became life-changing, and the experience shaped their resilient, scrappy mindset.
• Community as a Founder Superpower: Alina reflects on how building community—without tracking pipeline or ROI—has been vital to learning and joy. By showing up with genuine curiosity, she’s gained clarity on what customers really care about and how to serve them authentically.
• Leading with Empathy, Curiosity, and Drive: In describing each other’s superpowers, Alina credits Nicolas for his deep empathy and organizational clarity, while Nicolas points to Alina’s intense curiosity and willingness to experiment. Together, they’ve created a leadership model rooted in trust and transparency

Quote of the Show:

• " If you go with selfish reasons… people read that. Even if you don’t say it, they can feel it." - Alina Vandenberghe

Links:

• Alina’ LinkedIn: https://www.linkedin.com/in/alinav/
• Nicolas’ LinkedIn: https://www.linkedin.com/in/nvandenberghe/
• Website: https://www.chilipiper.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 #ChiliPiper

Chapters:

00:00 Intro

01:59 Early Challenges and First Customers

07:28 Building and Scaling the Team

12:59 Remote Work and Company Culture

17:55 Decision Making and Documentation

34:23 Alina's Superpower: Curiosity and Community Building

35:59 The Value of Community in Business

40:03 Nicholas's Superpower: Empathy and Human Insight

44:34 Challenges and Triumphs in Entrepreneurship

51:25 The Future of Chili Piper

54:25 Personal Backgrounds and Entrepreneurial Journeys

01:02:28 Balancing Family and Business

01:06:18 Advice for Aspiring Entrepreneurs

01:08:49 Outro

What does it take to lead lasting change in an organization? Alan Masarek, a multi-time CEO with a track record of company turnarounds, shares the lessons he’s learned from transforming brands like Vonage and Avaya.

In this in-depth conversation, Alan talks about building high-performing teams, the power of clear communication, succession planning, and how to lead authentically across companies of every size.

Takeaways:

• There’s No “One Thing” — But Culture Comes Close: Alan explains that success doesn’t come from a single action but a combination of choices: pursuing winnable markets, building strong teams, and creating cultures rooted in openness, honesty, and transparency.
• Clear, Simple, & Repetitive Communication: He emphasizes the necessity of repetitive messaging to reinforce confidence and direction within an organization. Regardless of the company size, developing the habit of effective communication early is crucial for long-term success.
• Transforming Vonage Meant Facing Reality: At Vonage, Alan led a shift from residential telephony to business communications. He dismantled internal divisions, repositioned the company, and made hard but necessary cultural changes by being direct about who was driving growth and who wasn’t.
• People Follow Leaders, Not Titles: Alan emphasizes hiring smart, high-integrity people and focusing on the top two layers of the organization. He looks for utility players with CEO potential, not just narrow specialists.
• Avoiding the Trap of Over-Reporting: When he arrived at Avaya, a 77-slide weekly report deck had become the norm. Alan reduced this dramatically, advocating for consistent, actionable metrics that focus on real business health rather than satisfying a process.
• Private Equity Dynamics Can Clash with Strategy: Alan reflects on the challenges of navigating fund timelines and liquidity needs, especially in private equity-backed companies. He notes that these dynamics can often push leaders toward short-term decisions at odds with long-term business goals.
• Leadership Isn’t About Work-Life Balance — It’s About Fulfillment: Alan shares his view that if you love what you do, work-life balance becomes irrelevant. He encourages young professionals to build wide foundations early in their careers by learning as much as they can, as fast as they can.

Quote of the Show:

• " Our job as leaders is to lay that picture out clearly... 'cause all too often we ask people to achieve what they can't imagine." - Alan Masarek

Links:

• LinkedIn: https://www.linkedin.com/in/alan-masarek-1aa1a8a8/
• Twitter (X): https://twitter.com/amasarek
• Website: https://www.avaya.com/en/
  
  

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 #Avaya

Chapters:

00:00 Intro

01:43 Alan Massek's Leadership Philosophy

05:45 The Importance of Communication in Leadership

07:20 Transforming Avaya: A Case Study

10:23 Challenges and Strategies in Business Transformation

17:03 Vonage Transformation: From Residential to Business Communications

28:50 Hiring and Building High-Performing Teams

40:22 The Importance of CEO Succession Planning

41:46 Navigating Acquisitions: Strategies and Insights

48:49 The Role of Private Equity in Modern Business

54:09 Life After Stepping Down as CEO

56:20 Leadership and Mentorship: Keys to Success

01:06:02 Work-Life Balance and Return to Office

01:14:28 Advice for Young Professionals

01:17:26 Outro

How do you grow a podcast into a true platform for founders and CEOs? In this solo episode of Not Another CEO Podcast, David Politis reflects on Q1 2025 and shares a behind-the-scenes look at what's next for the show.

From launching a Substack and partnering with Nick Freund to rethinking content distribution and recording locations, David breaks down what's working, what he’s learning, and the goals for the next quarter.

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 #DavidPolitis

Chapters:

00:00 Intro

00:42 Launch of Not Another CEO Substack

03:07 Partnership Announcement: Joining Forces with Nick Freund

05:31 Reflecting on Goals and Achievements

09:58 Looking Ahead: Goals for Q2

12:26 Outro