Not Another CEO Podcast

Do you know the key factors for successful leadership in high growth tech companies? In this episode, CEO of commercetools Andrew Burton shares his extensive experience in building and scaling tech companies. With over 25 years in the industry, Burton details his approach to leadership since becoming CEO of commercetools in 2024. He emphasizes the paramount importance of maintaining customer focus, building strong team culture, and aligning company goals.  Takeaways:Understanding Customer Needs: Andrew highlights the importance of stepping into customers' shoes to understand their challenges and measure success through their lens. He emphasizes starting conversations by asking customers about their challenges and how they define success.Aligning Around an Ideal Customer Profile: A crucial step Andrew implemented at commercetools was refining their Ideal Customer Profile (ICP). He stresses the necessity of focusing on where the company can deliver the most significant value and understanding why they're uniquely positioned to serve that particular segment.The Role of Leadership in Team Development: Andrew believes in playing as one team and ensuring a unified direction across the organization. He discusses the importance of testing for cultural and operational inconsistencies as a new CEO and aligning the team around shared objectives and metrics. Strategic Planning and Adapting to Change: Andrew shares insights into effective strategic planning by decoupling it from the stress of annual closing and starting a new fiscal year.Curiosity as a Driver for Success: Andrew describes how a curious approach to understanding problems and developing solutions leads to personal and organizational growth, making it a critical quality he looks for when hiring team members.Balancing Passion and Work-Life Integration: Andrew touches on the concept of work-life balance, suggesting that it is deeply connected to one's passion and motivation. He encourages individuals to be mindful of what genuinely drives them and to regularly assess whether their professional and personal lives are aligned with these motivations.Mentorship and Learning from Diverse Experiences: Andrew reflects on his journey and the importance of mentorship, emphasizing that learning from a variety of experiences and colleagues, regardless of hierarchy, contributes to a well-rounded leadership style.Quote of the Show:"Anybody that's really, I would argue successful… in their space, is going to know or have an appreciation for, at the core, the customer." - Andrew BurtonLinks:LinkedIn: https://www.linkedin.com/in/burtonandrew/Website: https://commercetools.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 #commercetoolsChapters:00:00 Intro01:58 The Importance of Customer-Centric Leadership04:21 Engaging with Customers: Strategies and Insights09:36 Aligning Company Mission and Team Goals13:10 Defining the Ideal Customer Profile (ICP)17:50 Building Trust and Credibility as a New CEO23:15 Strategic Planning and Measuring Success31:50 Monthly Cadence and Operational Efficiency33:05 Reflections on Planning and Offsite Meetings34:50 Journey to Becoming a CEO35:58 Curiosity and Leadership43:44 Mentorship and Influences46:24 Hiring and Growth Mindset51:43 Future of Commerce Tools53:36 Personal Background and Motivation56:59 Work-Life Balance and Career Advice01:01:48 Outro

What happens when you commit to shipping a podcast episode every week for an entire year? In this solo episode, David Politis reflects on 12 months of building Not Another CEO Podcast, from humble beginnings to an ever-growing audience of Founders, CEOs, and leaders. David shares 10 of his favorite highlights from the journey so far, covering everything from guest stories and personal milestones to the behind-the-scenes evolution of the show. This episode is a heartfelt thank-you to the community that has grown around the podcast and a look ahead at what’s next. 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 #Podcast #1YearReflection

What does it take to transform a scrappy logistics startup into a leading supply chain platform trusted by Fortune 500 brands? In this episode, Sean Henry shares the story of founding Stord, dropping out of college to build it, and scaling a distributed logistics network from zero to national reach. He opens up about fundraising setbacks, building conviction in tough moments, keeping customer experience front and center, and navigating the pressure of rapid growth while staying anchored in purpose. Takeaways:Dropping Out to Go All-In: Sean left college to pursue Stord full time, driven by a conviction that there was a better way to manage logistics in a fragmented industry. That early decision required grit and belief before traction or investor backing.Turning Cold Outreach Into Capital: Sean shares how his early fundraising relied on writing 150 cold emails a day. Persistence and storytelling helped him break through, eventually leading to key early checks that helped kickstart Stord’s growth.The Importance of Mission and Mindset: Through tough moments and early challenges, Sean and his Co-Founder stayed grounded in their mission. He talks about the psychological weight of leadership and the discipline required to keep moving forward.From Scrappy Marketplace to Full Stack Platform: Stord started as a logistics marketplace but pivoted into a fully integrated supply chain solution. Sean explains how that shift allowed them to deliver better customer experience, tighter control, and long-term defensibility.Customer Experience Is the Product: Even as a logistics company, Sean believes customer experience is the most important differentiator. He shares how Stord built systems and culture that put CX at the center of every part of the business.Navigating the Growth Curve Without Losing Focus: Sean discusses what it’s like to scale quickly while holding on to high standards. He shares lessons around team building, leadership habits, and making time for clarity amid the noise.Believe, But Be Realistic: Sean reflects on the importance of conviction, but also warns Founders to avoid believing their own hype. He recommends surrounding yourself with people who keep you honest and grounded as you grow.Quote of the Show:"If we don't have a customer, we don't have employees. If we have a vision but have no customers, that vision means nothing." - Sean HenryLinks:LinkedIn: https://www.linkedin.com/in/shenry96/Website: https://www.stord.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 #StordChapters:00:00 Intro01:49 The Importance of Customer Obsession05:44 Hiring for Customer Obsession10:19 Scaling and Company Culture21:30 Early Challenges and Pivots39:26 The Rise and Fall of the Trucking Network40:23 Navigating Hard Decisions and Growth42:50 Investor Relations and Fundraising Journey44:11 Mentorship and Early Influences45:33 Strategic Partnerships and Business Alignment51:23 Overcoming Challenges and Turning Points56:10 Future Vision and Expansion Plans01:03:51 Personal Background and Entrepreneurial Spirit01:13:14 Advice to His Younger Self1:14:40 Outro

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 RubinLinks: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 #CauselyChapters:00:00 Intro01:45 Key to Startup Success: Building the Right Team03:08 Exposing Team Members to the Bigger Picture06:08 Encouraging Curiosity and Engagement09:45 Supporting Women in Technology15:03 Challenges in the Tech Industry17:50 The Boston Tech Ecosystem21:37 Importance of Local Community in Remote Work Era27:08 Customer Engagement and Feedback30:07 Effective Operating Rhythms35:23 Lessons from Amazon37:50 Navigating the M&A Process38:31 Deciding the Right Time to Sell40:59 Taking Calls from Corporate Development44:30 The AI Revolution: A 70-Year Overnight Sensation46:00 The Role of AI in Modern Enterprises01:01:58 The Importance of Mentorship01:06:25 Balancing Entrepreneurship and Family01:09:13 Advice for Aspiring Entrepreneurs1:10:27 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 RichheimerLinks: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 #LawftyChapters:00:00 Intro01:41 The Importance of Complementary Skill Sets02:41 Finding a Co-Founder in an Unlikely Place03:44 Building Lawfty: From Idea to Execution06:19 Challenges and Strategies in Team Building09:29 Navigating the Interview Process12:47 Understanding Lawfty’s Business Model16:26 Early Customer Acquisition Tactics20:57 Fundraising Journey and Lessons Learned26:38 Scaling as a CEO29:31 The Legal Tech Revolution32:09 Challenges in Legal Services34:52 Building a Tech-Enabled Law Firm37:14 Overcoming Industry Stigma42:35 Fundraising Challenges and Solutions47:01 Personal Journey and Entrepreneurial Drive54:12 Advice for Aspiring Entrepreneurs56:48 Outro

What does it take to lead a global humanitarian organization through a pandemic and beyond? In this episode, Michael Nyenhuis shares how he has led UNICEF USA since March 2020, starting his role just two weeks after COVID shutdowns began. Michael talks about building strong boards and leadership teams, the balance between confidence and humility, and how to create connection in a hybrid work world. With decades of experience in humanitarian leadership, he reflects on his journey from journalist to President & CEO, and how staying close to mission and people shapes lasting impact.Find Michael's Newsletter here: https://www.linkedin.com/newsletters/relentless-6990692731056488449/ Takeaways:Rebuilding the Board and Leadership Team: Michael explains how reshaping governance and leadership early in his tenure has been crucial to the success of every organization he has led. He emphasizes getting the right people in place who share the mission and bring diverse skills and chemistry to the table.Evolution Over Revolution: Describing his leadership approach, Michael shares his belief in "relentless incrementalism." He believes consistent, thoughtful progress is more sustainable than sweeping change and that small steps taken regularly are key to building lasting impact.Starting a CEO Role in a Global Pandemic: Michael began his job just as COVID shut the world down. He relied on daily video updates, creative communication, and a golden retriever named Izzy to build relationships remotely. He reflects on the benefits and drawbacks of trying to lead without in-person interaction.Creating Culture in a Hybrid Workplace: UNICEF USA has embraced hybrid work, but Michael is intentional about maintaining connection. From monthly staff engagement days to leadership meetings and all-staff retreats, he builds structured moments for human interaction and relationship-building.Honest Career Advice for Aspiring Humanitarians: Michael stresses that global development is a profession, not just a passion. He shares how expertise, formal experience, and training are key to entering the nonprofit space and why it is important to respect the rigor of humanitarian work.CEO Roundtables and Mentorship by Listening: Michael hosts monthly roundtables with staff based on anniversary dates, offering space for Q&A and storytelling. He also invited youth leaders to mentor him, flipping the script to show respect and learn from the next generation of changemakers.Balancing Confidence and Humility: Michael reflects on the need to balance strong leadership with the humility to listen. Early in his career, he sometimes over-relied on consensus. Today, he sees the value in trusting instincts while remaining open.Quote of the Show:"When you find what you're supposed to do, doors start opening." - Michael NyenhuisLinks:LinkedIn: https://www.linkedin.com/in/michaelnyenhuis/Website: https://www.unicefusa.org/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 #UNICEFUSAChapters:00:00 Intro01:28 Key Achievements at UNICEF USA03:18 Building Effective Leadership Teams14:13 Navigating Challenges During the Pandemic20:14 Remote and Hybrid Work Dynamics29:31 CEO Round Table and Onboarding30:48 Operating Rhythm and Annual Planning32:18 Monthly Staff Meetings and Engagement36:22 Public Speaking and Media Training39:55 Managing Diverse Constituents42:36 Biggest Challenge: Leading Through COVID-1945:16 Career Journey and Journalism Background51:47 Mentorship and Youth Engagement54:32 Balancing Confidence and Humility in Leadership58:03 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 DellLinks: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 #DomainMoneyChapters:00:00 Intro01:25 Recruiting Strategies for Startups07:15 Fundraising Insights and Market Sentiment11:46 The Evolution of Domain Money16:25 Navigating Pivots and Team Buy-In23:07 Growth Strategies and Partnerships26:20 Acquisitions and Exits29:23 Strategic Partnerships and Revenue Growth30:37 The Impact of AI on Technology and Business35:12 AI in Financial Planning and Wealth Management39:51 Challenges and Pivots in Business49:09 Personal Background and Entrepreneurial Journey57:37 Advice for Aspiring Entrepreneurs01:00:30 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 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