Not Another CEO Podcast

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

What happens when you combine relentless focus with long-term trust and bootstrapped grit? In this episode of Not Another CEO Podcast, David Politis chats with Sean Griffey, the co-founder and former CEO of Industry Dive, a digital media company that went from humble beginnings to a $500M+ acquisition.Sean dives into how simplicity became his core operating principle, the creative strategies behind building a strong team, and why bootstrapping gave him the ultimate freedom. He also opens up about co-founder dynamics, the emotional challenges of scaling leadership, and finding clarity after stepping down. Takeaways:Start with Simplicity, Scale with Clarity: Sean shares how simplicity became a guiding principle across operations, sales, and product. By constantly asking “How can we make this easier?”, Industry Dive streamlined execution and scaled effectively across 30 different markets.The Coffee Challenge That Built Culture: To foster cross-team collaboration, new hires were given a $50 coffee stipend and a list of quirky and strategic questions to ask people outside their department. This initiative not only built early camaraderie but also helped break down silos before they could form.Bootstrapping with Intent (and $400K): While Industry Dive raised a small angel round, Sean considered the business bootstrapped and didn’t pay himself for 18 months. He talks about resisting early VC offers in favor of building profitably and why media businesses need time, not acceleration.Strategic Exit Through Private Equity: Sean shares how the PE partnership offered strategic guidance, operating support, and true alignment on growth goals.The Leadership Challenges No One Talks About: Sean reflects on the difficulty of maintaining culture and connection at scale, especially through the pandemic. He emphasizes the importance of transparency, weekly all-hands, and honest company-wide Q&As—even when the questions were tough.Letting Go and What Comes Next: After stepping down as CEO, Sean is still adjusting. He shares how he's staying engaged and how he’s giving himself space to figure out what’s next with no pressure.Quote of the Show:“There’s an incredible amount of time to be successful… you can enjoy it along the way too.” - Sean GriffeyLinks:LinkedIn: https://www.linkedin.com/in/seangriffey/Twitter (X): http://twitter.com/seangriffeyCompany Website: https://www.industrydive.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 #IndustryDiveChapters:00:00 Intro01:27 Key Strategies for Success at Industry Dive02:31 The Coffee Challenge: Building Cross-Departmental Relationships07:15 Maintaining Simplicity in Business Operations10:19 Co-Founder Dynamics and Roles16:34 Bootstrapping and Fundraising Journey26:09 Private Equity Partnership Experience29:00 Private Equity's Role in Scaling30:57 Navigating the Pandemic with Private Equity33:03 Alignment and Exit Strategy with Private Equity37:51 Challenges and Team Alignment47:42 CEO's Reflections and Future Plans51:03 Advice for Aspiring Entrepreneurs58:29 Outro

What happens when a cybersecurity expert pioneers a new approach to phishing defense? Join us as we delve into the journey of Rohyt Belani, Co-Founder and Former CEO of PhishMe, who turned a simple idea into a $400 million exit to BlackRock. Rohyt discusses his unique business strategies, the importance of an employee-first culture, navigating massive challenges, and raising capital efficiently. Watch now to gain invaluable entrepreneurial insights from one of the leading minds in cybersecurity. Takeaways:Bootstrapping to Success: Rohyt discusses how he and his co-founder bootstrapped the company to $2.5 million in ARR before accepting any external funding. They leveraged their prior industry experience and personal networks to secure their first enterprise customers.Implementing Employee-Friendly Policies: The adoption of policies such as half-day Fridays significantly boosted morale and productivity among staff. Rohyt emphasizes the importance of putting employees first and how this principle was pivotal in creating a positive company culture. Transitioning From Services to Product: Rohyt talks about the challenges and learning curve associated with moving from a consulting company to a scalable product business. He highlights the necessity of balancing growth with capital efficiency and the mindset shift required to achieve this.Acquiring Enterprise Customers: The PhishMe team focused on a hands-on approach to customer acquisition, including attending numerous industry events and leveraging their expertise in cybersecurity to build trust. Expansion into new markets was approached cautiously and strategically, ensuring that initial customer wins provided a foundation for further growth.Investigated by the U.S. government: Rohyt recounts the hardships faced during a CFIUS investigation into a Russian investor associated with their private equity backer. Despite an onslaught of negative publicity and customer attrition, the PhishMe team managed to steer the company through this crisis while maintaining their integrity and focus on growth.Fundraising and Investor Relations: Initially, raising capital was a grueling process involving over 100 investor meetings to secure their first funding. However, as PhishMe demonstrated significant growth, subsequent funding rounds saw increased interest, culminating in multiple competing term sheets and better negotiation leverage.Balancing Innovation and Customer Needs: The importance of listening to customer feedback and anticipating future needs led to the development of complementary products, which significantly boosted the company's market standing and revenue. This approach ensured that PhishMe stayed relevant and valuable to its customers.Quote of the Show:“ There's probably a hundred good ideas for any given product, and you have to be able to whittle it down to say, what are the three things we're doing over the next three to six months?” - Rohyt BelaniLinks:LinkedIn: https://www.linkedin.com/in/rohytbelani/Twitter (X): https://x.com/rohytbelaniCompany Website: https://cofense.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 #PhishMeChapters:00:00 Intro01:17 What You'd Do Again as CEO04:20 Challenges and Insights on Work Culture07:16 Early Customer Acquisition16:06 Fundraising Journey23:26 Product Evolution and Expansion30:15 Navigating Customer Feedback and Innovation32:40 Defining and Evolving the Ideal Customer Profile (ICP)33:45 Transitioning from Consulting to Product Company36:09 Challenges and Strategies in Scaling a Product Company41:40 Overcoming a Major Crisis: The CFIUS Investigation47:01 Life After Stepping Down: Advising and Mentoring48:55 Reflections on Entrepreneurship and Mentorship57:31 Outro

In this discussion, Itamar Friedman, Co-Founder and CEO of Qodo, shares his journey from AI researcher to entrepreneur. He highlights how AI can transform software development by enhancing code integrity and automating testing processes. Itamar delves into the unique challenges of building reliable AI tools for developers. He also touches on the importance of company culture in fostering innovation and reflects on transitioning from CTO to CEO, emphasizing the need for a well-rounded leadership approach in the tech industry.

How do you build a brand that resonates deeply with millions of customers? In this episode of Not Another CEO Podcast, David Politis sits down with Nadia Boujarwah, Co-Founder and Former CEO of Dia&Co, to discuss her journey in revolutionizing plus-size fashion. Nadia shares the challenges of building an inclusive brand, navigating venture funding, and leading a mission-driven company through rapid growth and industry shifts. She also reflects on the power of community, hiring the right team, and the lessons she learned stepping down as CEO after a decade at the helm. Takeaways:The Power of a Co-Founder Relationship: Nadia emphasizes that choosing the right Co-Founder is one of the most critical decisions in a startup journey. She shares how this played a pivotal role in shaping Dia&Co and why equal economics from day one helped maintain a strong partnership.Building a Business from the Ground Up: Before developing a scalable platform, Nadia and her Co-Founder personally shopped for thousands of customers to deeply understand their needs. She explains why doing things manually in the early days was key to creating a product-market fit.Fundraising Challenges & Breakthroughs: Raising Dia&Co’s first million dollars took nearly a year, yet within 18 months, they secured over $100 million in funding. Nadia shares insights on what changed, how she navigated investor skepticism, and why the right investors can make all the difference.Scaling from Startup to Major Brand: At its peak, Dia&Co hired 600 people in a single year. Nadia discusses the challenges of leading a fast-growing organization, maintaining company culture, and evolving her leadership style to keep up with the business’s rapid expansion.The Role of Community in Brand Building: The Dia&Co customer base formed organic Facebook groups that grew into a passionate and engaged community. Nadia shares how customers turned into brand ambassadors, planned meetups, and even got tattoos to represent the brand’s impact.Navigating Major Business Shifts & the Pandemic: From industry-wide changes to the unpredictability of COVID-19, Nadia reflects on leading through uncertainty, making tough calls, and staying resilient in the face of evolving challenges.Stepping Down as CEO & What’s Next: After a decade of building Dia&Co, Nadia made the difficult decision to transition out of the CEO role. She opens up about that process, how she adjusted to life post-CEO, and what she’s exploring next.Quote of the Show:“ There's a fundamental attribute of being an immigrant that you think that the locus of control in your life is inside of you” - Nadia BoujarwahLinks:LinkedIn: https://www.linkedin.com/in/nadiaboujarwah/Company Website: https://www.dia.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 #Dia&CoChapters:00:00 Intro01:40 What You’d Do Again As CEO08:06 Starting Dia&Co: From Idea to Execution14:38 Building a Community and Raising Funds22:52 Navigating Investor Relationships27:45 Transitioning Leadership at Dia&Co33:29 Biggest Challenge Faced at Dia&Co36:53 Growing Up in an Immigrant Family41:02 The Value of an MBA49:33 Future of AI in Apparel52:07 Advice to Younger Self55:47 Outro

Daniel Chait, Co-founder and CEO of Greenhouse, shares his journey from software engineer to leading a top hiring platform. He emphasizes the importance of structured hiring and defining a clear mission to drive success. Chait details the challenges of fundraising, revealing the persistence needed to attract investors. He also discusses the evolution of leadership in rapidly growing companies, stressing effective communication and cultural alignment. Additionally, he reflects on balancing entrepreneurship with family life, drawing from personal experiences.

Kyle Porter, the founder and former CEO of SalesLoft, shares his incredible journey of scaling the company to a $2 billion exit. He reveals how leading with love shaped the company culture and attracted top talent. The conversation dives into creative marketing strategies, like the daring Dreamforce stunt with a lookalike of Salesforce's CEO. Kyle also reflects on navigating competition, the role of impactful investors, and the importance of balancing career ambitions with family life. A heartfelt exploration of values-driven leadership!

What does it take to build and scale a successful company? In this episode of Not Another CEO Podcast, David Politis sits down with Zac Smith, Co-Founder and Former CEO of Packet. Zac discusses the importance of structured execution, hiring for passion, and balancing long-term vision with short-term execution. Whether you're a founder, leader, or aspiring entrepreneur, this conversation is packed with valuable insights on leadership, company building, and decision-making. Takeaways:The Power of a 10-Year Vision: Zac believes that thinking long-term is critical for building meaningful businesses. He explains how setting a bold 10-year goal helps guide decision-making and prioritization in the short term.Entrepreneurial Operating System (EOS) for Success: One of Zac’s most impactful lessons was implementing EOS to create structure and accountability within his companies. He shares how this system helped him move from gut-driven decisions to a scalable business framework.Execution is the Differentiator: Most companies operate at a 3 or 4 out of 10 in execution. Zac explains how simply executing at a 7 or 8 puts businesses ahead of the competition and increases the likelihood of success.Hiring for Passion & Curiosity: Beyond skills, Zac prioritizes candidates who show genuine interest and curiosity. He shares how small actions, like trying a product before an interview, can reveal whether someone is truly invested in a company’s mission.Lessons from Leading Through Crisis: From navigating financial challenges to making tough leadership decisions, Zac reflects on some of the hardest moments of his career, including when he and his co-founder decided to replace themselves as leaders to save the company.Building a Personal Brand in B2B Sales: In enterprise sales, people buy from people, not just companies. Zac shares how investing in personal brand-building—through speaking, blogging, and community engagement—was key to winning customers at Packet.Quote of the Show:“ I don’t need to run a 10 out of 10 for a company. Most companies are operating at a 3 or a 4. I just want to be a 7 or an 8.” - Zac SmithLinks:LinkedIn: https://www.linkedin.com/in/zsmithWays 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 #PacketChapters:0:00 Intro1:25 What You’d Do Again As CEO3:18 Deep Dive into EOS and Its Benefits7:41 Building a Passionate and Accountable Team9:50 The Importance of Vision and Long-Term Goals13:20 Effective Interview Techniques and Identifying Passion19:57 Communicating Vision and Values29:33 Go-to-Market Strategies and Early Customer Acquisition34:38 Early Users and Initial Challenges39:22 New York Tech Scene Evolution45:25 Biggest Challenge Faced51:41 Rich’s Background1:05:49 Advice to Younger Self1:02:21 Outro

How do you build an organization that truly fights poverty at scale? In this episode of Not Another CEO Podcast, David Politis sits down with Rich Buery, CEO of the Robin Hood Foundation, to discuss his leadership journey, his experience shaping policies like Universal Pre-K in NYC, and how Robin Hood is evolving to meet modern challenges.Rich shares insights on hiring with purpose, managing multiple stakeholders, and why philanthropy needs both measurable outcomes and deep human connection to drive real change. Takeaways:Weekly CEO Emails for Transparency: Rich started sending a weekly email to Robin Hood staff every Monday morning, sharing updates on his week, priorities, and even personal reflections. This practice fosters alignment, strengthens internal communication, and helps employees feel more connected to leadership.The Power of Celebration in Workplace Culture: Robin Hood embraces celebrations, from birthdays to cultural events, to strengthen relationships among employees. Rich emphasizes the importance of fostering a connected workplace, especially in a hybrid work environment.Hiring for Passion, Not Just Skills: When interviewing candidates, Rich prioritizes one key question: "Why Robin Hood? Why now?" He looks for candidates who have a deep, personal connection to the organization's mission, believing that true passion is the most valuable trait an employee can bring.Balancing Five Key Stakeholders: Robin Hood serves five different groups: donors, nonprofit partners, policymakers, internal teams, and the communities they support. Rich discusses how managing these relationships requires tailored communication and a clear focus on measurable impact.Data-Driven Philanthropy: Robin Hood employs a rigorous evidence-based approach to funding, using data to quantify the financial impact of its programs, to ensure donor funds are invested in initiatives that create measurable and lasting change for those living in poverty.The Role of AI in Social Impact: Rich explores how Robin Hood is working to ensure that nonprofit organizations—and the communities they serve—are equipped to navigate the technological changes from AI.Quote of the Show:“ What is it about your life, your work, your vision of the world that draws you to this mission? It’s the one thing that you can’t necessarily teach or train… for any job.” - Richard BueryLinks:LinkedIn: https://www.linkedin.com/in/richardbuery/Twitter: https://x.com/RichardBueryWebsite: https://robinhood.org/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 #RobinHoodChapters:0:00 Intro1:37 What You’d Do Again As CEO6:05 Building a Collaborative Executive Team8:56 Hiring for Passion and Mission Alignment14:31 The Importance of Storytelling and Public Speaking3:24 Navigating Multiple Constituencies34:03 Analog Solutions in a Digital World38:43 Challenges of Leading Robin Hood39:41 Fundraising and Donor Engagement43:36 Impact of AI and Technology46:09 Rich’s Background1:00:01 Advice to Younger Self1:02:21 Outro