Not Another CEO Podcast

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 LazerowLinks: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!TChapters:00:00 Intro00:46 Podcast Journey and Growth01:41 Acknowledging Sponsors and Supporters03:56 Introducing Cass and Mike Lazaro05:33 Building Buddy Media: Key Strategies and Insights08:19 Challenges and Successes in Leadership14:09 The Importance of Transparency15:19 Husband-Wife Co-Founders: A Unique Dynamic20:09 Fundraising and Building Relationships27:46 Marketing and Branding Strategies34:09 Thought Leadership and Public Speaking36:36 Navigating Business Pivots38:25 The Birth of Buddy Media40:31 Challenges and Successes of Custom Apps45:20 Balancing Family and Business48:50 Advice for Aspiring Entrepreneurs54:58 Building a Positive Company Culture01:02:21 Q&A with the Audience01:11:11 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 TzuoLinks: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 #ZuoraChapters:00:00 Intro02:00 The Journey of Building Zuora03:59 Scaling and Team Dynamics07:43 Founder's Journey and Coaching22:12 Strategic Planning and Execution30:28 Frameworks for Strategic Alignment32:33 Self-Awareness and Leadership34:10 Execution-Oriented Teams37:03 Lessons from Salesforce38:07 The Power of Storytelling40:59 Advice on Managing Time43:33 Biggest Challenges and Overcoming Them46:24 Future Vision for Zuora48:22 Personal Journey and Motivation52:33 Advice for Aspiring Founders54:13 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 SwigartLinks: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 #PieInsuranceChapters:00:00 Intro01:42 Key Decisions and Leadership Challenges07:24 Building and Evolving Leadership Teams11:03 The Concept of Founder Mode20:58 Competing in a Highly Regulated Market31:13 Early Days and Customer Acquisition31:53 Early Days of Multi-Channel Distribution34:35 Fundraising Challenges and Successes36:59 Building an Impressive Board42:33 Navigating Business Challenges48:39 Founding a Company Later in Life53:46 Personal Growth and Mentorship57:06 Pivotal Career Moments01:00:48 Advice for Aspiring Entrepreneurs01:02:17 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 PasulkaLinks:LinkedIn: https://www.linkedin.com/in/spasulka/TikTok: https://www.tiktok.com/@sashaiscookingWays 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 #ElkaAIChapters:00:00 Intro03:07 The Aha Moment: Founding Elka AI04:30 Challenges in Marketing and AI Solutions09:42 Building the Product: Alpha and Beta Phases18:07 The Struggles of Fundraising and Leadership25:22 Navigating Luck and Timing in Entrepreneurship27:38 Key Decisions and Reflections31:56 Navigating AI Non-Determinism33:01 Support System and Key Influences36:38 Fundraising Challenges and Lessons42:40 Gender Dynamics in Fundraising48:47 Personal Journey and Reflections56:01 Advice for Future Founders01:00:05 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 transparencyQuote of the Show:" If you go with selfish reasons… people read that. Even if you don’t say it, they can feel it." - Alina VandenbergheLinks: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 #ChiliPiperChapters:00:00 Intro01:59 Early Challenges and First Customers07:28 Building and Scaling the Team12:59 Remote Work and Company Culture17:55 Decision Making and Documentation34:23 Alina's Superpower: Curiosity and Community Building35:59 The Value of Community in Business40:03 Nicholas's Superpower: Empathy and Human Insight44:34 Challenges and Triumphs in Entrepreneurship51:25 The Future of Chili Piper54:25 Personal Backgrounds and Entrepreneurial Journeys01:02:28 Balancing Family and Business01:06:18 Advice for Aspiring Entrepreneurs01:08:49 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 MasarekLinks:LinkedIn: https://www.linkedin.com/in/alan-masarek-1aa1a8a8/Twitter (X): https://twitter.com/amasarekWebsite: 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 #AvayaChapters:00:00 Intro01:43 Alan Massek's Leadership Philosophy05:45 The Importance of Communication in Leadership07:20 Transforming Avaya: A Case Study10:23 Challenges and Strategies in Business Transformation17:03 Vonage Transformation: From Residential to Business Communications28:50 Hiring and Building High-Performing Teams40:22 The Importance of CEO Succession Planning41:46 Navigating Acquisitions: Strategies and Insights48:49 The Role of Private Equity in Modern Business54:09 Life After Stepping Down as CEO56:20 Leadership and Mentorship: Keys to Success01:06:02 Work-Life Balance and Return to Office01:14:28 Advice for Young Professionals01:17:26 Outro

What does it take to build a pioneering luxury lingerie brand? In this episode, Jennifer Zuccarini, Founder and CEO of Fleur du Mal, shares her journey from launching her second company in the lingerie space to creating a brand celebrated by celebrities and top fashion publications. Jennifer opens up about key moments in her entrepreneurial path, including nurturing team culture, expanding product lines, and overcoming financial hurdles. She also discusses the importance of community-building, the challenges of retail expansion, and the creative satisfaction that drives her forward. Takeaways:Staying True to the Vision: Jennifer explains that her original idea for Fleur du Mal remains core to what the brand is today. She emphasizes the importance of holding onto that original creative inspiration while evolving with new trends and consumer expectations.Focusing on Team Culture: Jennifer underscores the importance of investing in team culture. She admits that early on, she was more focused on building the brand, but now she emphasizes team recognition. Initiatives like 'employee of the season' and regular team outings, such as Spring Equinox parties and personalized birthday celebrations, have helped create a strong, appreciative team environment.Overcoming Financial Challenges: Jennifer reveals a critical moment two years into Fleur du Mal when the company almost ran out of money. She borrowed funds from investors and had to delay payroll, which resulted in losing much of her team. Despite the setback, she managed to rebuild the company, describing it as the most challenging period in her professional life.Passion for Product and Brand: Jennifer highlights her deep passion for product design and brand building, taking personal involvement in every aspect from approving email marketing to attending every product fitting.Innovative Products and Methods: She details the challenges and strategies involved in creating and marketing new products, especially within the constraints of advertising restrictions on platforms like Google and Meta.Retail Expansion and Community Building: Jennifer discusses the strategic expansion of Fleur du Mal’s retail footprint. By leveraging data from their strong online business, they identify ideal locations for new stores to build community and enhance customer experience. Personal and Professional Growth: Reflecting on her career, Jennifer values the importance of appreciating the journey. She advises founders to find satisfaction in their daily work and to recognize that building something meaningful takes time and effort.Quote of the Show:" I think the best brands really have a very strong point of view that they stick to all the time." - Jennifer ZuccariniLinks:LinkedIn: https://www.linkedin.com/in/jenniferzuccarini/Twitter (X): https://x.com/jzuccariniWebsite: https://fleurdumal.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 #FleurduMalChapters:00:00 Intro01:33 Building a Strong Team Culture05:21 Passion for Product and Brand06:27 Challenges in Brand Building14:54 Expanding Product Lines18:27 Navigating Marketing Restrictions26:22 Engaging with the Community28:48 The Power of Authenticity in Business29:24 Expanding Retail Strategy29:41 Balancing Retail and Online Presence30:41 Challenges of Retail Expansion31:37 Future Plans and Team Building34:20 Overcoming Financial Challenges37:53 Lessons from Transparency and Team Loss42:08 Entrepreneurial Spirit and Family Influence44:48 Mentorship and Role Models46:58 Drive and Motivation51:17 Advice for Aspiring Entrepreneurs54:53 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 #DavidPolitisChapters:00:00 Intro00:42 Launch of Not Another CEO Substack03:07 Partnership Announcement: Joining Forces with Nick Freund05:31 Reflecting on Goals and Achievements09:58 Looking Ahead: Goals for Q212:26 Outro

What happens when passion, persistence, and curiosity meet the brutal realities of startup life? In this Failing Forward edition of Not Another CEO Podcast, Nick Freund sits down with Anthony Corletti, a seasoned technical founder and former CEO of Casa, to unpack his entrepreneurial journey. Anthony shares hard-won lessons from building, and ultimately shutting down, his company, discusses frameworks like the "Founder’s Care-o-Meter" and the "Personal Board of Advisors," and reflects on how founding has shaped his broader life perspective. Takeaways:The Spark for Entrepreneurship: Anthony shares how working closely with rideshare drivers during his early startup days ignited his passion for solving real-world problems through tech, and how the immediacy of feedback fueled his love for early-stage building.What Drives a Technical Founder: For Anthony, the excitement lies in scaling impact, solving one user's problem in a way that could eventually benefit thousands. His love of learning and "always day one" mindset continues to push him forward.The Lightbulb Moment for Casa: A podcast analogy about how context transforms perception inspired Anthony to rethink how engineering workspaces could better integrate product and design teams, leading to the idea behind Casa.Introducing the Founder’s Care-o-Meter: Anthony explains the framework he created to check his conviction at different stages of building Casa. He tracked whether he still felt a "hell yes" about the mission and scored his emotional connection to the problem versus the solution every six weeks.Building a Personal Board of Advisors: Anthony stresses the importance of surrounding yourself with trusted confidants, from family to expert mentors, who can offer honest feedback, accountability, and different perspectives throughout the founder journey.Knowing When to Shut Down: Anthony candidly describes how feedback from pilot customers, competitive insights, and introspection via the Care-o-Meter helped him make the difficult but clear-eyed decision to wind down Casa.Founding and Life Philosophy: Anthony reflects on how founding has shaped his view of service, resilience, and embracing life's unexpected opportunities. His future focus is simple: prioritize the people you work with and the problems you solve.Quote of the Show:" Experience is what you get when maybe you didn't get what you wanted… being able to share that with [future founders] is such a critical point, and it's super important." - Anthony CorlettiLinks:LinkedIn: https://www.linkedin.com/in/anthonycorletti/Twitter (X): https://x.com/anthonycorlettiWebsite: https://www.anthonycorletti.com/Ways to Tune In:Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261 Transistor: https://podcast.notanotherceo.com/ YouTube: https://www.youtube.com/@NotAnotherCEOPodcast #NotAnotherCEO #BusinessSuccess #CasaChapters:00:00 Intro04:14 Anthony's Journey and Early Career09:10 The Inspiration Behind Casa14:51 The Founder's Care-o-Meter19:49 Building a Personal Board of Advisors25:57 Facing Initial Challenges26:57 Pivoting and Feedback27:31 Connecting with Industry Leaders29:28 Emotional Journey of a Founder31:01 Reflecting on Key Decisions33:06 The Importance of Co-Founders33:46 Customer-Centric Product Development36:16 The Role of Luck in Success38:46 Balancing Life and Founding39:42 Founder's Philosophy and Future Plans45:55 Where To Next?48:24 Outro

How do you scale a company to $200 million+ in ARR while maintaining deep empathy for the customer? In this episode of Not Another CEO Podcast, David Politis sits down with Todd Olson, the Founder and CEO of Pendo, to find out. Todd shares the values and rituals that helped him scale Pendo into a product-led powerhouse, including his unwavering commitment to customer-centricity, his direct approach to hiring, and the operating cadence that keeps his nearly 900-person team aligned. Todd reflects on the highs, lows, and philosophies that have guided his journey. Takeaways:Customer Obsession as a Foundational Value: Todd emphasizes how being “maniacally focused on the customer” has guided every stage of Pendo’s growth. From answering support tickets himself in the early days to personally monitoring feedback as CEO, he’s created a culture where customer empathy cascades through every department.Every Hire Must Talk to Customers: Todd shares a hiring principle he’s followed since day one: only hire people you'd trust on the phone with a customer. This standard shaped Pendo’s culture, even affecting how they screen engineers, ensuring they’re willing and able to engage directly with users.Personally Interviewing Hundreds: At one point, Todd personally interviewed every employee… almost 800 people. Beyond vetting talent, it was a powerful tool for maintaining cultural consistency and calibrating hiring managers across the org. He also ran 90-day check-ins with new hires to ensure expectations matched reality.Product Leadership Rooted in Vision: Though product leadership has evolved at Pendo, Todd has remained deeply involved in product vision and strategy. He describes how he stays hands-on with design sessions, brainstorming new features, and ensuring Pendo’s tools meet the high bar of product teams building for product teams.Disciplined Operating Rhythm: Todd credits much of Pendo’s success to a consistent cadence of planning and communication. Annual and quarterly planning rituals, town halls, and regular team offsites help align the company around shared goals and keep stress in check during turbulent times.Built in Raleigh, Built to Last: Despite early pressure to move to Silicon Valley, Todd built and scaled Pendo out of Raleigh, North Carolina. He shares how the local ecosystem shaped the company and how hiring executives from outside the region helped them compete on a national scale while staying grounded in local roots.Quote of the Show:"Nearly every product is like, strongly opinionated, meaning when you use it, you feel like it has a point of view that it’s trying to impart." - Todd OlsonLinks:LinkedIn: https://www.linkedin.com/in/toddaolsonTwitter (X): https://x.com/tolsonCompany Website: https://www.pendo.io/Ways to Tune In:Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261 Transistor: https://podcast.notanotherceo.com/ YouTube: https://www.youtube.com/@NotAnotherCEOPodcast #NotAnotherCEO #BusinessSuccess #PendoChapters:00:00 Intro01:23 The Importance of Customer Obsession02:34 Early Days and Customer Engagement04:57 Hiring for Customer Focus08:39 Personal Stories and Career Reflections11:27 Interviewing Every Employee18:24 Product Evolution and Ideal Customer Profile26:19 Operating Rhythm and Business Cadence34:53 Adapting and Planning for Long-Term Success37:17 Biggest Challenges Faced at Pendo43:56 Future Vision for Pendo47:00 Early Career and Entrepreneurial Spark53:49 Building a Business in Raleigh56:59 Balancing Family and Business01:02:55 Outro